MersV1, Pmc, Corpus, bibRecord, 000984

Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)

Identifieur interne : 000984 ( Pmc/Corpus ); précédent : 000983; suivant : 000985

Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)

Auteurs : Mohammed A. E. Shaibah ; Belakavadi K. Sagar ; Hemmige S. Yathirajan ; David B. Cordes ; Alexandra M. Z. Slawin ; William T. A. Harrison

Source :

Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2019.

RBID : PMC:6362640

Abstract

The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C₁₁H₁₉N₂S⁺) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH⁺=C—NH₂ fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N⁺H₂ resonance form to the structure.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6362640

DOI: 10.1107/S2056989018018224
PubMed: 30800445
PubMed Central: 6362640

Links to Exploration step

PMC:6362640

Le document en format XML

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(8) supramolecular motif (even when disordered)</title>
<author><name sortKey="Shaibah, Mohammed A E" sort="Shaibah, Mohammed A E" uniqKey="Shaibah M" first="Mohammed A. E." last="Shaibah">Mohammed A. E. Shaibah</name>
<affiliation><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Sagar, Belakavadi K" sort="Sagar, Belakavadi K" uniqKey="Sagar B" first="Belakavadi K." last="Sagar">Belakavadi K. Sagar</name>
<affiliation><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Yathirajan, Hemmige S" sort="Yathirajan, Hemmige S" uniqKey="Yathirajan H" first="Hemmige S." last="Yathirajan">Hemmige S. Yathirajan</name>
<affiliation><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B." last="Cordes">David B. Cordes</name>
<affiliation><nlm:aff id="b">School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Slawin, Alexandra M Z" sort="Slawin, Alexandra M Z" uniqKey="Slawin A" first="Alexandra M. Z." last="Slawin">Alexandra M. Z. Slawin</name>
<affiliation><nlm:aff id="b">School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T. A." last="Harrison">William T. A. Harrison</name>
<affiliation><nlm:aff id="c">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country>
</nlm:aff>
</affiliation>
</author>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust <inline-formula><inline-graphic xlink:href="e-75-00167-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
(8) supramolecular motif (even when disordered)</title>
<author><name sortKey="Shaibah, Mohammed A E" sort="Shaibah, Mohammed A E" uniqKey="Shaibah M" first="Mohammed A. E." last="Shaibah">Mohammed A. E. Shaibah</name>
<affiliation><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Sagar, Belakavadi K" sort="Sagar, Belakavadi K" uniqKey="Sagar B" first="Belakavadi K." last="Sagar">Belakavadi K. Sagar</name>
<affiliation><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Yathirajan, Hemmige S" sort="Yathirajan, Hemmige S" uniqKey="Yathirajan H" first="Hemmige S." last="Yathirajan">Hemmige S. Yathirajan</name>
<affiliation><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B." last="Cordes">David B. Cordes</name>
<affiliation><nlm:aff id="b">School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Slawin, Alexandra M Z" sort="Slawin, Alexandra M Z" uniqKey="Slawin A" first="Alexandra M. Z." last="Slawin">Alexandra M. Z. Slawin</name>
<affiliation><nlm:aff id="b">School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T. A." last="Harrison">William T. A. Harrison</name>
<affiliation><nlm:aff id="c">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title>
<idno type="eISSN">2056-9890</idno>
<imprint><date when="2019">2019</date>
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<front><div type="abstract" xml:lang="en"><p>The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH<sup>+</sup>
=C—NH<sub>2</sub>
 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N<sup>+</sup>
H<sub>2</sub>
 resonance form to the structure.</p>
</div>
</front>
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<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
  <front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr E Crystallogr Commun</journal-id>
<journal-id journal-id-type="iso-abbrev">Acta Crystallogr E Crystallogr Commun</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Crystallographic Communications</journal-title>
</journal-title-group>
<issn pub-type="epub">2056-9890</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">30800445</article-id>
<article-id pub-id-type="pmc">6362640</article-id>
<article-id pub-id-type="publisher-id">mw2140</article-id>
<article-id pub-id-type="doi">10.1107/S2056989018018224</article-id>
<article-id pub-id-type="coden">ACSECI</article-id>
<article-id pub-id-type="pii">S2056989018018224</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject>
</subj-group>
</article-categories>
<title-group><article-title>Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust <inline-formula><inline-graphic xlink:href="e-75-00167-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
(8) supramolecular motif (even when disordered)</article-title>
<alt-title><italic>five molecular salts</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Shaibah</surname>
<given-names>Mohammed A. E.</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Sagar</surname>
<given-names>Belakavadi K.</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0001-9039-0273</contrib-id>
<name><surname>Yathirajan</surname>
<given-names>Hemmige S.</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-5366-9168</contrib-id>
<name><surname>Cordes</surname>
<given-names>David B.</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Slawin</surname>
<given-names>Alexandra M. Z.</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0003-2253-4866</contrib-id>
<name><surname>Harrison</surname>
<given-names>William T. A.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<aff id="a"><label>a</label>
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country>
</aff>
<aff id="b"><label>b</label>
School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country>
</aff>
<aff id="c"><label>c</label>
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>w.harrison@abdn.ac.uk</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>2</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="epub"><day>08</day>
<month>1</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>08</day>
<month>1</month>
<year>2019</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the . </pmc-comment>
      <volume>75</volume>
<issue>Pt 2</issue>
<issue-id pub-id-type="publisher-id">e190200</issue-id>
<fpage>167</fpage>
<lpage>174</lpage>
<history><date date-type="received"><day>10</day>
<month>12</month>
<year>2018</year>
</date>
<date date-type="accepted"><day>21</day>
<month>12</month>
<year>2018</year>
</date>
</history>
<permissions><copyright-statement>© Shaibah et al. 2019</copyright-statement>
<copyright-year>2019</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/4.0/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted
use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
<ali:license_ref>http://creativecommons.org/licenses/by/4.0/</ali:license_ref>
</license>
</permissions>
<self-uri xlink:href="https://doi.org/10.1107/S2056989018018224">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract abstract-type="toc"><p>The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH<sup>+</sup>
=C—NH<sub>2</sub>
 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N<sup>+</sup>
H<sub>2</sub>
 resonance form to the structure.</p>
</abstract>
<abstract><p>The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-methylbenzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>−</sup>
, (I), 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-bromobenzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>−</sup>
, (II), 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 3,5-dinitrobenzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>−</sup>
, (III), bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) fumarate, 2C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2−</sup>
,(IV), and the 1:1 co-crystal of bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) succinate and 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine, 1.5C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·0.5C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2−</sup>
·0.5C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>−</sup>
. 0.5C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S, (V). In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH<sup>+</sup>
=C—NH<sub>2</sub>
 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N<sup>+</sup>
H<sub>2</sub>
 resonance form to the structure. The packing for (I)–(V) features a robust local <italic>R</italic>
<sub>2</sub>
<sup>2</sup>
(8) loop motif in which the cation forms two near-linear N—H⋯O hydrogen bonds from the N<sup>+</sup>
—H group and <italic>syn</italic>
 H atom of the amine group to the carboxylate group of an adjacent anion [(V) shows disorder of one of these bonds over N—H⋯O and N⋯H—O contributors but the same <italic>R</italic>
<sub>2</sub>
<sup>2</sup>
(8) loop results for both disorder components]. The <italic>anti</italic>
 H atom of the –NH<sub>2</sub>
 group also forms an N—H⋯O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetramers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.</p>
</abstract>
<kwd-group><kwd>benzothiazole</kwd>
<kwd>hydrogen bond</kwd>
<kwd>molecular salt</kwd>
<kwd>crystal structure</kwd>
</kwd-group>
<funding-group><award-group><funding-source>University Grants Commission</funding-source>
<award-id>UGC-BSR Faculty Fellowship</award-id>
<award-id>Rajeev Gandhi fellowship</award-id>
<principal-award-recipient>H. S. Yathirajan</principal-award-recipient>
<principal-award-recipient>B. K. Sagar</principal-award-recipient>
</award-group>
<funding-statement>This work was funded by <funding-source>University Grants Commission</funding-source>
 grants <award-id>UGC-BSR Faculty Fellowship</award-id>
 and <award-id>Rajeev Gandhi fellowship</award-id>
. </funding-statement>
</funding-group>
<counts><page-count count="8"></page-count>
</counts>
</article-meta>
</front>
<body><sec id="sec1"><title>Chemical context   </title>
<p>Some 2-aminobenzothiazole derivatives display important biological properties: riluzole [2-amino-6-(trifluoromethoxy)benzothiazole] is used in the palliative treatment of amyotrophic lateral sclerosis (Sweeney <italic>et al.</italic>
, 2018<xref ref-type="bibr" rid="bb20"> ▸</xref>
) and pramipexole dihydrochloride [(<italic>S</italic>
)-<italic>N</italic>
6-propyl-4,5,6,7-tetrahydrobenzo[<italic>d</italic>
]thiazole-2,6-diamine dihydrochloride] is used to combat Parkinson’s disease (Roy <italic>et al.</italic>
, 2018<xref ref-type="bibr" rid="bb15"> ▸</xref>
). We note that the six-membered ring in the latter compound is reduced by the addition of four H atoms. In coordination chemistry, 2-aminobenzothiazole has been shown to ligate to various metal ions, for example copper(II) (Kuwar <italic>et al.</italic>
, 2018<xref ref-type="bibr" rid="bb9"> ▸</xref>
), cadmium(II) (Ma <italic>et al.</italic>
, 2012<xref ref-type="bibr" rid="bb10"> ▸</xref>
) and palladium(II) (Gao <italic>et al.</italic>
, 2011<xref ref-type="bibr" rid="bb6"> ▸</xref>
). The utility of 2-aminobenzothiazole in organic synthesis has recently been reviewed (Dadmal <italic>et al.</italic>
, 2018<xref ref-type="bibr" rid="bb3"> ▸</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-75-00167-scheme1.jpg" position="float" orientation="portrait"></graphic>
</chem-struct>
</p>
<p>As part of our ongoing studies in this area (Sagar <italic>et al.</italic>
, 2017<xref ref-type="bibr" rid="bb16"> ▸</xref>
), we now describe the syntheses and crystal structures of five molecular salts of 4,4,7,7-tetramethyl-3a,4,5,6,7,7a-hexahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S) with different carboxylic acids, viz. 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-methylbenzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>−</sup>
, (I)<xref ref-type="chem" rid="scheme1"></xref>
; 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-bromobenzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>−</sup>
, (II)<xref ref-type="chem" rid="scheme1"></xref>
; 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 3,5-dinitrobenzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>−</sup>
, (III)<xref ref-type="chem" rid="scheme1"></xref>
; bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) fumarate, (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
)<sub>2</sub>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2−</sup>
,(IV); 1:1 co-crystal of bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) succinate and (2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) hydrogen succinate 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine, (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
)<sub>1.5</sub>
·(C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2−</sup>
)<sub>0.5</sub>
·(C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>−</sup>
)<sub>0.5</sub>
·(C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S)<sub>0.5</sub>
, (V)<xref ref-type="chem" rid="scheme1"></xref>
.</p>
</sec>
<sec id="sec2"><title>Structural commentary   </title>
<p>The asymmetric units of (I)<xref ref-type="chem" rid="scheme1"></xref>
, (II)<xref ref-type="chem" rid="scheme1"></xref>
 and (III)<xref ref-type="chem" rid="scheme1"></xref>
 are illustrated in Figs. 1<xref ref-type="fig" rid="fig1"> ▸</xref>
, 2<xref ref-type="fig" rid="fig2"> ▸</xref>
 and 3<xref ref-type="fig" rid="fig3"> ▸</xref>
, respectively. Each one features a 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) cation protonated at the thiazole-ring nitrogen atom N1 accompanied by a substituted benzoate anion. The C7—N1 and C7—N2 bond lengths in the cations in (I)<xref ref-type="chem" rid="scheme1"></xref>
 [1.325 (3) and 1.322 (4) Å, respectively], (II)<xref ref-type="chem" rid="scheme1"></xref>
 [1.327 (5) and 1.316 (5) Å, respectively] and (III)<xref ref-type="chem" rid="scheme1"></xref>
 [1.3267 (19) and 1.322 (2) Å, respectively] are almost identical, presumably indicating a significant contribution of the amidinium cation [—N1H—C7=N2<sup>+</sup>
H<sub>2</sub>
] resonance form to the overall structure [compare ions <italic>A</italic>
 and <italic>B</italic>
 in the chemical scheme of Sagar <italic>et al.</italic>
 (2017<xref ref-type="bibr" rid="bb16"> ▸</xref>
)]. The C1—S1—C7 bond angles [(I) = 90.27 (13); (II)<xref ref-type="chem" rid="scheme1"></xref>
 = 90.29 (18); (III)<xref ref-type="chem" rid="scheme1"></xref>
 = 90.40 (7)°] are almost identical in the three salts. The conformation of the reduced (hydrogenated/methylated) six-membered ring of the benzothiazole moiety can be described as a half-chair in each case; in (I)<xref ref-type="chem" rid="scheme1"></xref>
, the deviating methylene groups (C3 and C4) are disordered over two sets of sites in a 0.602 (10):0.398 (10) ratio. For (II)<xref ref-type="chem" rid="scheme1"></xref>
, atoms C3 and C4 deviate from the plane defined by C1/C2/C5/C6 by −0.388 (13) and 0.130 (11) Å, respectively; comparable data for (III)<xref ref-type="chem" rid="scheme1"></xref>
 are −0.276 (3) and 0.432 (3) Å, respectively. The dihedral angles between the C1/C2/C5/C6 moiety and the C1/C6/C7/N1/S1 thiazole ring for (I)<xref ref-type="chem" rid="scheme1"></xref>
 [1.3 (2)°], (II)<xref ref-type="chem" rid="scheme1"></xref>
 [1.2 (3)°] and (III)<xref ref-type="chem" rid="scheme1"></xref>
 [2.84 (13)°] indicate a slight, but statistically significant, puckering in each case.</p>
<p>In the substituted benzoate anion in (I)<xref ref-type="chem" rid="scheme1"></xref>
, the C18—O1 [1.252 (3) Å] and C18—O2 [1.267 (3) Å] distances indicate substantial electronic delocalization within the carboxylate group; the dihedral angle between the C12–C17 benzene ring and C18/O1/O2 is 7.0 (6)°. The equivalent data for (II)<xref ref-type="chem" rid="scheme1"></xref>
 are C18—O1 = 1.260 (5), C18—O2 = 1.263 (5) Å and C12–C17 + C18/O1/O2 dihedral angle = 6.2 (8)°. The data for (III)<xref ref-type="chem" rid="scheme1"></xref>
 are C18—O1 = 1.2475 (19), C18—O2 = 1.2506 (19) Å and dihedral angle = 4.9 (4)°. Additionally, the dihedral angles between the benzene ring and the N3 and N4 nitro groups in (III)<xref ref-type="chem" rid="scheme1"></xref>
 are 16.0 (3) and 11.9 (3)°, respectively.</p>
<p>The asymmetric unit of (IV)<xref ref-type="chem" rid="scheme1"></xref>
 (Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>
) features two C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
 cations and one dianion, which of course ensures charge balance. The structural features of the cations in (IV)<xref ref-type="chem" rid="scheme1"></xref>
 are very similar to those of the equivalent species in (I)–(III): the C7—N1 and C7—N2 bond lengths of the S1 cation are 1.325 (6) and 1.318 (6) Å, respectively and the C18—N3 and C18—N4 bond lengths of the S2 cation are 1.320 (6) and 1.319 (7) Å, respectively and the same conclusion regarding delocalization of the [—N<sup>+</sup>
1H=C7—N2H<sub>2</sub>
] moiety as was noted for (I)–(III) can be drawn. The conformations of the six-membered rings are half-chairs in each case; in the N1 cation, the deviating methylene groups (C3 and C4) are disordered over two sets of sites in a 0.78 (2):0.22 (2) ratio but these species are ordered in the N3 cation [deviations of C14 and C15 from the C12/C13/C16/C17 plane = 0.408 (11) and −0.309 (11) Å, respectively]. The fused rings are slightly puckered [dihedral angles (as defined above) = 0.7 (5) and 6.0 (3)° for the N1 and N3 cations, respectively]. In the fumarate anion in (IV)<xref ref-type="chem" rid="scheme1"></xref>
, the carboxylate bond lengths are C23—O1 = 1.251 (6), C23—O2 = 1.258 (6), C26—O3 = 1.267 (6) and C26—O4 = 1.232 (6) Å.</p>
<p>The asymmetric unit of (V)<xref ref-type="chem" rid="scheme1"></xref>
 (Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>
) is more complex due to disorder of one of the transferable protons and can be envisaged as a 1:1 co-crystal of (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
)<sub>2</sub>
·(C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2−</sup>
) <italic>(i.e.</italic>
 proton transfer from both carboxylate groups of the anion) and (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
)·(C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>−</sup>
)(C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S) (<italic>i.e.</italic>
: proton transfer from one of carboxylate groups of the anion). This is further discussed below under supramolecular features. Despite this disorder, the situation for the N1 and N3 cations in (V)<xref ref-type="chem" rid="scheme1"></xref>
 is very similar to that in (IV)<xref ref-type="chem" rid="scheme1"></xref>
: C7—N1 = 1.325 (3); C7—N2 = 1.317 (4); C18—N3 = 1.322 (3); C18—N4 = 1.336 (4) Å. The C1–C6 ring is disordered over two half-chair conformations in a 0.596 (11):0.404 (11) ratio but the C12–C17 ring is ordered with C14 and C15 deviating from the other atoms by 0.424 (6) and −0.313 (6) Å, respectively. The inter-ring dihedral angles are 0.6 (3) (N1 cation) and 1.3 (3)° (N3 cation). Key bond-length data for the succinate anion in (V)<xref ref-type="chem" rid="scheme1"></xref>
 are C23—O1 = 1.254 (4), C23—O2 = 1.249 (4), C26—O3 = 1.284 (4) and C26—O4 = 1.229 (4) Å. These data indicate that the C—O single and double bonds within the C26/O3/O4 moiety are more localized than in the other structures reported here, which correlates with the proton disorder model associated with O3.</p>
<p>The ‘anomalous’ situation of incomplete proton transfer for (V)<xref ref-type="chem" rid="scheme1"></xref>
 might be correlated with p<italic>K</italic>
<sub>a</sub>
 values for the acids involved: 4-methylbenzoic acid (p<italic>K</italic>
<sub>a</sub>
 = 4.25), 4-bromobenzoic acid (3.99), 3,5-dinitrobenzoic acid (2.77), fumaric acid (p<italic>K</italic>
<sub>a1</sub>
 = 3.03, p<italic>K</italic>
<sub>a2</sub>
 = 4.54) and succinic acid (4.21, 5.64). These data apply to the acids dissolved in water (Jover <italic>et al.</italic>
, 2008<xref ref-type="bibr" rid="bb8"> ▸</xref>
), but we might guess that a similar trend applies in the crystals and the p<italic>K</italic>
<sub>a2</sub>
 value for succinic acid is clearly larger than the others. Incomplete (or partial) proton transfer processes have been observed in other crystals (<italic>e.g.</italic>
 Biliškov <italic>et al.</italic>
, 2011<xref ref-type="bibr" rid="bb1"> ▸</xref>
) and can lead to interesting physical properties (<italic>e.g.</italic>
 Noohinejad <italic>et al.</italic>
, 2015<xref ref-type="bibr" rid="bb12"> ▸</xref>
).</p>
</sec>
<sec id="sec3"><title>Supramolecular features   </title>
<p>The most notable supramolecular feature (which occur within the asymmetric units as defined here) of (I)–(V) is an <inline-formula><inline-graphic xlink:href="e-75-00167-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
(8) loop in which the protonated N1<sup>+</sup>
—H1 moiety of the thiazole ring and the <italic>syn</italic>
 H atom of the –N2H<sub>2</sub>
 amine group both form near-linear N—H⋯O hydrogen bonds to the O atoms of the carboxylate group of an adjacent anion [Tables 1<xref ref-type="table" rid="table1"> ▸</xref>
–5<xref ref-type="table" rid="table2"> ▸</xref>
<xref ref-type="table" rid="table3"> ▸</xref>
<xref ref-type="table" rid="table4"> ▸</xref>
<xref ref-type="table" rid="table5"> ▸</xref>
 for compounds (I)–(V), respectively]. In (V)<xref ref-type="chem" rid="scheme1"></xref>
, the proton disorder associated with N3 and O3 leads to the same motif for both disorder components (two N—H⋯O bonds or one N—H⋯O and one N⋯H—O bond). Despite the presumed electronic delocalization of the cation noted above, it may be seen that for (I)–(III), the H⋯O distance for the charge-assisted hydrogen bond arising from N1 is notably shorter than the bond arising from N2. The situation for (IV)<xref ref-type="chem" rid="scheme1"></xref>
 and (V)<xref ref-type="chem" rid="scheme1"></xref>
 is less clear-cut: the H⋯O separations for the N1 and N2 (and equivalent N3 and N4) hydrogen bonds tend to be closer in magnitude and indeed the N2 bond in (IV)<xref ref-type="chem" rid="scheme1"></xref>
 is marginally shorter than the N1 bond. The intermolecular dihedral angles between the thiazole and benzoate rings are 17.13 (14), 16.42 (19) and 20.15 (8)° for (I)<xref ref-type="chem" rid="scheme1"></xref>
, (II)<xref ref-type="chem" rid="scheme1"></xref>
 and (III)<xref ref-type="chem" rid="scheme1"></xref>
, respectively, suggesting that the pairwise hydrogen bonds tend to align the aromatic rings of the cation and the anion in roughly the same plane.</p>
<p>In every case, the amine N2–H3<italic>N</italic>
 group <italic>anti</italic>
 to the N<sup>+</sup>
H group of the thiazole ring also forms an N—H⋯O hydrogen bond, but the different anions lead to different overall structures. Salts (I)<xref ref-type="chem" rid="scheme1"></xref>
 and (II)<xref ref-type="chem" rid="scheme1"></xref>
 are isostructural (<italic>i.e</italic>
. the same space group and packing with slight differences in the unit-cell parameters to accommodate the different para-substituents of the benzoate anion), with the N2—H3<italic>N</italic>
 group linking the ion pairs into [001] chains (Fig. 6<xref ref-type="fig" rid="fig6"> ▸</xref>
), with adjacent molecules related by <italic>c</italic>
-glide symmetry. It may be noted that O2 accepts both hydrogen bonds from the amide H atoms and O1 accepts the charge-assisted bond from the thiazole ring.</p>
<p>The situation for (III)<xref ref-type="chem" rid="scheme1"></xref>
 is quite different, with isolated centrosymmetric tetramers (two cations and two anions) arising (Fig. 7<xref ref-type="fig" rid="fig7"> ▸</xref>
) in which pairs of <inline-formula><inline-graphic xlink:href="e-75-00167-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
(8) loops linking one cation to two anions are apparent as well as the cation-to-anion <inline-formula><inline-graphic xlink:href="e-75-00167-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
(8) loops already mentioned. A weak C—H⋯O interaction (Table 3<xref ref-type="table" rid="table3"> ▸</xref>
) arising from a methyl group occurs between tetramers.</p>
<p>Crystals (IV)<xref ref-type="chem" rid="scheme1"></xref>
 and (V)<xref ref-type="chem" rid="scheme1"></xref>
 are isostructural and feature [100] chains in each case (Fig. 8<xref ref-type="fig" rid="fig8"> ▸</xref>
). It may be seen that locally the cation has the same hydrogen-bonding pattern to the anion as in (I)<xref ref-type="chem" rid="scheme1"></xref>
 and (II)<xref ref-type="chem" rid="scheme1"></xref>
 but because the dianions accept hydrogen bonds at ‘both ends’, a different overall structure arises, which features the same <inline-formula><inline-graphic xlink:href="e-75-00167-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
(8) loop seen in (III)<xref ref-type="chem" rid="scheme1"></xref>
, but is not generated by a crystallographic centre of symmetry.</p>
</sec>
<sec id="sec4"><title>Hirshfeld surface analyses   </title>
<p>The Hirshfeld surfaces of the C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
 cations in (I)–(V) were calculated using <italic>CrystalExplorer</italic>
 (Turner <italic>et al.</italic>
, 2017<xref ref-type="bibr" rid="bb21"> ▸</xref>
) and fingerprint plots (McKinnon <italic>et al.</italic>
, 2007<xref ref-type="bibr" rid="bb11"> ▸</xref>
) were also generated. An example fingerprint plot for (I)<xref ref-type="chem" rid="scheme1"></xref>
 is shown in Fig. 9<xref ref-type="fig" rid="fig9"> ▸</xref>
; plots for (II)–(V) are available in the <ext-link ext-link-type="uri" xlink:href="#suppinfoanchor">supporting information</ext-link>
. The prominent ‘spike’ feature terminating at (<italic>d</italic>
<sub>i</sub>
, <italic>d</italic>
<sub>e</sub>
 = ∼0.62, 0.98) corresponds to the N—H⋯O hydrogen bonds. Less prominent spikes at (1.30, 2.05) and (2.05, 1.30) correspond to H⋯S and S⋯H contacts, respectively: if these are indicative of attractive directional interactions, they must be very weak at best, as the shortest H⋯S/S⋯H contact is 3.31 Å, compared to the van der Waals separation of 3.0 Å for these atoms.</p>
<p>The percentage surface contact data (Table 6<xref ref-type="table" rid="table6"> ▸</xref>
) for the C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
 species in the five structures reveal a number of similarities but also some differences: H⋯H contacts dominate the packing in each case, although the percentage for (III)<xref ref-type="chem" rid="scheme1"></xref>
 is significantly less that for the others. The H⋯O contacts associated with the hydrogen bonds are very consistent for (I)<xref ref-type="chem" rid="scheme1"></xref>
, (II)<xref ref-type="chem" rid="scheme1"></xref>
, (IV)<xref ref-type="chem" rid="scheme1"></xref>
 and (V)<xref ref-type="chem" rid="scheme1"></xref>
, but those for (II)<xref ref-type="chem" rid="scheme1"></xref>
 are much higher and presumably reflect the presence of the ‘extra’ O atoms of the nitro substituents of the anion, although no significant directional interactions could be identified for these O atoms apart from one weak C—H⋯O bond. The C⋯all, N⋯all and S⋯all contact percentages are almost identical for the five structures.</p>
</sec>
<sec id="sec5"><title>Database survey   </title>
<p>So far as we are aware, the only reported crystal structures to contain the 4,4,7,7-tetramethyl-3a,4,5,6,7,7a-hexahydrobenzothiazol-2-ylamine cation are those described recently by Sagar <italic>et al.</italic>
 (2017<xref ref-type="bibr" rid="bb16"> ▸</xref>
) (refcodes NEFTIE and NEFTOK), where it was crystallized with benzoate and picrate anions, respectively. The benzoate structure contains essentially the same hydrogen-bonded chains of cations and anions generated by <italic>c</italic>
-glide symmetry as in (I)<xref ref-type="chem" rid="scheme1"></xref>
 and (II)<xref ref-type="chem" rid="scheme1"></xref>
 although it is not isostructural (space group <italic>Cc</italic>
 rather than <italic>Pc</italic>
). The centrosymmetric, hydrogen-bonded tetramers in the picrate structure bear a resemblance to those in (III)<xref ref-type="chem" rid="scheme1"></xref>
 but in the picrate anion, the acceptor oxygen atoms are the deprotonated phenol –OH group and adjacent nitro-group O atoms rather than carboxylate O atoms.</p>
<p>A search of the Cambridge Structural Database (Groom <italic>et al.</italic>
, 2016<xref ref-type="bibr" rid="bb7"> ▸</xref>
, updated to August 2018) for 2-aminobenzothiazole with any substituents (including protonation) revealed 189 matches, but this number dropped to just five for a hydrogenated/methylated six-membered ring, viz. (−)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole (<sc>l</sc>
)-(+)-tartrate trihydrate (refcode FECZES; Schneider & Mierau, 1987<xref ref-type="bibr" rid="bb17"> ▸</xref>
); <italic>rac</italic>
-4,5,5a,6,7,8-hexahydro-6-<italic>n</italic>
-propylthiazolo(4,5-<italic>f</italic>
)quinolin-2-amine methanol solvate (SONZIE; Caprathe <italic>et al.</italic>
, 1991<xref ref-type="bibr" rid="bb2"> ▸</xref>
); 2-amino-5,6-dihydro-1,3-benzothiazol-7(4<italic>H</italic>
)-one (TESGUV; Zhu <italic>et al.</italic>
, 2012<xref ref-type="bibr" rid="bb23"> ▸</xref>
), as well as NEFTIE and NEFTOK referred to in the previous paragraph.</p>
</sec>
<sec id="sec6"><title>Synthesis and crystallization   </title>
<p>4,4,7,7-Tetramethyl-3a,4,5,6,7,7a-tetrahydrobenzothiazol-2-ylamine (200 mg. 0.94 mmol) and the equivalent amount of the respective acids, <italic>i.e.</italic>
 4-methylbenzoic acid (135 mg, 0.94 mmol) for (I)<xref ref-type="chem" rid="scheme1"></xref>
, 4-bromobenzoic acid (200 mg, 0.94 mmol) for (II)<xref ref-type="chem" rid="scheme1"></xref>
, 3,5-dinitrobenzoic acid (208 mg, 0.94 mmol) for (III)<xref ref-type="chem" rid="scheme1"></xref>
, fumaric acid (112 mg, 0.94 mmol) for (IV)<xref ref-type="chem" rid="scheme1"></xref>
 and succinic acid (115 mg, 0.94 mmol) for (V)<xref ref-type="chem" rid="scheme1"></xref>
, were dissolved in hot methanol and stirred over a heating magnetic stirrer for few minutes. The solution was allowed to cool slowly at room temperature and the resulting solids were recovered by filtration and drying in air. These were recrystallized at room temperature using a 1:1 solvent mixture of DMF and DMSO: crystals of (I)<xref ref-type="chem" rid="scheme1"></xref>
 (m.p. 441–443 K), (II)<xref ref-type="chem" rid="scheme1"></xref>
 (m.p. 473 K), (III)<xref ref-type="chem" rid="scheme1"></xref>
 (m.p. 453–456 K), (IV)<xref ref-type="chem" rid="scheme1"></xref>
 (m.p. 446–450 K) and (V)<xref ref-type="chem" rid="scheme1"></xref>
 (m.p. 393–396 K) appeared after a week.</p>
</sec>
<sec id="sec7"><title>Refinement   </title>
<p>Crystal data, data collection and structure refinement details are summarized in Table 7<xref ref-type="table" rid="table7"> ▸</xref>
. The methylene groups in (I)<xref ref-type="chem" rid="scheme1"></xref>
, (IV)<xref ref-type="chem" rid="scheme1"></xref>
 and (V)<xref ref-type="chem" rid="scheme1"></xref>
 were modelled as being disordered over two sets of sites and the C atoms were refined with isotropic displacement parameters. The N-bound H atoms were located in difference-Fourier maps and their positions were freely refined without difficulty in every case except for the proton associated with atoms N3 and O3 in compound (V). Careful scrutiny of difference maps indicated two electron density maxima in the vicinity of these two atoms, one in a reasonable location for an N3—H⋯O3 hydrogen bond (<italic>i.e</italic>
. proton transferred) and the other corresponding to an N3⋯H—O3 hydrogen bond (<italic>i.e.</italic>
 proton not transferred): for a detailed discussion of proton location in potentially disordered hydrogen bonds, see Fábry (2018<xref ref-type="bibr" rid="bb4"> ▸</xref>
). Despite their feeble scattering power, when included in the atomic model these refined well as disordered H atoms: their occupancy sum was constrained to unity and revealed equal occupancies [0.50 (5):0.50 (5)] for the two sites. H atoms for all structures were placed geometrically (C—H = 0.95–0.99 Å) and refined as riding atoms. The methyl groups were allowed to rotate, but not to tip, to best fit the electron density. In every case, the constraint <italic>U</italic>
<sub>iso</sub>
(H) = 1.2<italic>U</italic>
<sub>eq</sub>
(carrier) or 1.5<italic>U</italic>
<sub>eq</sub>
(methyl carrier) was applied. The absolute structures of (I)<xref ref-type="chem" rid="scheme1"></xref>
, (II)<xref ref-type="chem" rid="scheme1"></xref>
, (IV)<xref ref-type="chem" rid="scheme1"></xref>
 and (V)<xref ref-type="chem" rid="scheme1"></xref>
 were established by refinement of the Flack absolute structure parameter (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb13"> ▸</xref>
). It may be noted that despite being isostrutural, the crystal of (IV)<xref ref-type="chem" rid="scheme1"></xref>
 chosen for data collection was found to be an inversion twin, whereas the chosen crystal of (V)<xref ref-type="chem" rid="scheme1"></xref>
 has a well-defined absolute structure (despite disorder).</p>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) I, II, III, IV, V, global. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140sup1.cif">10.1107/S2056989018018224/mw2140sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-75-00167-sup1.cif" orientation="portrait" id="d35e159" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140Isup2.hkl">10.1107/S2056989018018224/mw2140Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-75-00167-Isup2.hkl" orientation="portrait" id="d35e166" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) II. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140IIsup3.hkl">10.1107/S2056989018018224/mw2140IIsup3.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-75-00167-IIsup3.hkl" orientation="portrait" id="d35e173" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) III. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140IIIsup4.hkl">10.1107/S2056989018018224/mw2140IIIsup4.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-75-00167-IIIsup4.hkl" orientation="portrait" id="d35e180" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) IV. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140IVsup5.hkl">10.1107/S2056989018018224/mw2140IVsup5.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-75-00167-IVsup5.hkl" orientation="portrait" id="d35e187" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) V. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140Vsup6.hkl">10.1107/S2056989018018224/mw2140Vsup6.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-75-00167-Vsup6.hkl" orientation="portrait" id="d35e194" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-75-00167-Isup7.cml"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140Isup7.cml">10.1107/S2056989018018224/mw2140Isup7.cml</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-75-00167-IIsup8.cml"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140IIsup8.cml">10.1107/S2056989018018224/mw2140IIsup8.cml</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-75-00167-IIIsup9.cml"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140IIIsup9.cml">10.1107/S2056989018018224/mw2140IIIsup9.cml</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-75-00167-IVsup10.cml"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018018224/mw2140IVsup10.cml">10.1107/S2056989018018224/mw2140IVsup10.cml</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><p>CCDC references: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1886885">1886885</ext-link>
, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1886884">1886884</ext-link>
, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1886883">1886883</ext-link>
, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1886882">1886882</ext-link>
, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1886881">1886881</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?mw2140&file=mw2140sup0.html&mime=text/html"> crystallographic information</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?mw2140sup1&Qmime=cif">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?mw2140&checkcif=yes">checkCIF report</ext-link>
</p>
</supplementary-material>
</sec>
</body>
<back><ack><p>MAES thanks the University of Mysore for provision of research facilities.</p>
</ack>
<app-group><app><title>supplementary crystallographic information</title>
<sec id="d1e159" sec-type="tablewrapcrystaldatalong"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e168"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>−</sup>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 372</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 346.48</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.208 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 10.1879 (5) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 5914 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 11.6149 (5) Å</td>
<td rowspan="1" colspan="1">θ = 2.2–28.1°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 8.7790 (4) Å</td>
<td rowspan="1" colspan="1">µ = 0.18 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 113.480 (6)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 173 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 952.82 (9) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">Plate, colourless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 2</td>
<td rowspan="1" colspan="1">0.24 × 0.11 × 0.02 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e294" sec-type="tablewrapdatacollectionlong"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e303"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Rigaku XtaLAB P200 HPC diffractometer</td>
<td rowspan="1" colspan="1">4056 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: rotating anode, Rigaku FR-X</td>
<td rowspan="1" colspan="1">3440 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Rigaku Osmic Confocal Optical System monochromator</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.029</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 29.0°, θ<sub>min</sub>
 = 1.8°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −13→12</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.793, <italic>T</italic>
<sub>max</sub>
 = 1.000</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −15→15</td>
</tr>
<tr><td rowspan="1" colspan="1">12189 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −11→11</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e405" sec-type="tablewraprefinementdatalong"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e414"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Hydrogen site location: mixed</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.038</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0463<italic>P</italic>
)<sup>2</sup>
 + 0.0807<italic>P</italic>
] where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.089</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 < 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.03</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.20 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">4056 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.17 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">230 parameters</td>
<td rowspan="1" colspan="1">Absolute structure: Flack <italic>x</italic> determined using 1371 quotients
[(<italic>I</italic>
<sup>+</sup>
)-(<italic>I</italic>
<sup>-</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>-</sup>)]
(Parsons <italic>et al.</italic>
, 2013).</td>
</tr>
<tr><td rowspan="1" colspan="1">2 restraints</td>
<td rowspan="1" colspan="1">Absolute structure parameter: 0.03 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e592" sec-type="specialdetails"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e602"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e611" sec-type="tablewrapcoords"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e623"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1">Occ. (<1)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.3617 (3)</td>
<td rowspan="1" colspan="1">0.6584 (2)</td>
<td rowspan="1" colspan="1">0.8458 (3)</td>
<td rowspan="1" colspan="1">0.0363 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.2322 (3)</td>
<td rowspan="1" colspan="1">0.6675 (3)</td>
<td rowspan="1" colspan="1">0.8865 (4)</td>
<td rowspan="1" colspan="1">0.0466 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3A</td>
<td rowspan="1" colspan="1">0.1685 (10)</td>
<td rowspan="1" colspan="1">0.7939 (8)</td>
<td rowspan="1" colspan="1">0.8152 (12)</td>
<td rowspan="1" colspan="1">0.058 (3)*</td>
<td rowspan="1" colspan="1">0.398 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A1</td>
<td rowspan="1" colspan="1">0.0740</td>
<td rowspan="1" colspan="1">0.8028</td>
<td rowspan="1" colspan="1">0.8210</td>
<td rowspan="1" colspan="1">0.069*</td>
<td rowspan="1" colspan="1">0.398 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A2</td>
<td rowspan="1" colspan="1">0.2329</td>
<td rowspan="1" colspan="1">0.8534</td>
<td rowspan="1" colspan="1">0.8878</td>
<td rowspan="1" colspan="1">0.069*</td>
<td rowspan="1" colspan="1">0.398 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A</td>
<td rowspan="1" colspan="1">0.1525 (10)</td>
<td rowspan="1" colspan="1">0.8143 (9)</td>
<td rowspan="1" colspan="1">0.6457 (13)</td>
<td rowspan="1" colspan="1">0.048 (2)*</td>
<td rowspan="1" colspan="1">0.398 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A1</td>
<td rowspan="1" colspan="1">0.1003</td>
<td rowspan="1" colspan="1">0.8874</td>
<td rowspan="1" colspan="1">0.6050</td>
<td rowspan="1" colspan="1">0.058*</td>
<td rowspan="1" colspan="1">0.398 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A2</td>
<td rowspan="1" colspan="1">0.0957</td>
<td rowspan="1" colspan="1">0.7512</td>
<td rowspan="1" colspan="1">0.5735</td>
<td rowspan="1" colspan="1">0.058*</td>
<td rowspan="1" colspan="1">0.398 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B</td>
<td rowspan="1" colspan="1">0.1217 (6)</td>
<td rowspan="1" colspan="1">0.7333 (5)</td>
<td rowspan="1" colspan="1">0.7440 (7)</td>
<td rowspan="1" colspan="1">0.0467 (18)*</td>
<td rowspan="1" colspan="1">0.602 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B1</td>
<td rowspan="1" colspan="1">0.0401</td>
<td rowspan="1" colspan="1">0.7535</td>
<td rowspan="1" colspan="1">0.7730</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1">0.602 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B2</td>
<td rowspan="1" colspan="1">0.0852</td>
<td rowspan="1" colspan="1">0.6836</td>
<td rowspan="1" colspan="1">0.6441</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1">0.602 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B</td>
<td rowspan="1" colspan="1">0.1860 (7)</td>
<td rowspan="1" colspan="1">0.8447 (6)</td>
<td rowspan="1" colspan="1">0.7047 (9)</td>
<td rowspan="1" colspan="1">0.0468 (15)*</td>
<td rowspan="1" colspan="1">0.602 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B1</td>
<td rowspan="1" colspan="1">0.1081</td>
<td rowspan="1" colspan="1">0.8907</td>
<td rowspan="1" colspan="1">0.6225</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1">0.602 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B2</td>
<td rowspan="1" colspan="1">0.2291</td>
<td rowspan="1" colspan="1">0.8911</td>
<td rowspan="1" colspan="1">0.8074</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1">0.602 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.3013 (3)</td>
<td rowspan="1" colspan="1">0.8207 (2)</td>
<td rowspan="1" colspan="1">0.6356 (4)</td>
<td rowspan="1" colspan="1">0.0412 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.3917 (3)</td>
<td rowspan="1" colspan="1">0.7225 (2)</td>
<td rowspan="1" colspan="1">0.7371 (3)</td>
<td rowspan="1" colspan="1">0.0342 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.5894 (3)</td>
<td rowspan="1" colspan="1">0.6071 (2)</td>
<td rowspan="1" colspan="1">0.8256 (3)</td>
<td rowspan="1" colspan="1">0.0341 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.1541 (6)</td>
<td rowspan="1" colspan="1">0.5542 (4)</td>
<td rowspan="1" colspan="1">0.8622 (7)</td>
<td rowspan="1" colspan="1">0.111 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.0673</td>
<td rowspan="1" colspan="1">0.5643</td>
<td rowspan="1" colspan="1">0.8833</td>
<td rowspan="1" colspan="1">0.167*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">0.2164</td>
<td rowspan="1" colspan="1">0.4971</td>
<td rowspan="1" colspan="1">0.9397</td>
<td rowspan="1" colspan="1">0.167*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8C</td>
<td rowspan="1" colspan="1">0.1280</td>
<td rowspan="1" colspan="1">0.5275</td>
<td rowspan="1" colspan="1">0.7480</td>
<td rowspan="1" colspan="1">0.167*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.2747 (4)</td>
<td rowspan="1" colspan="1">0.7056 (4)</td>
<td rowspan="1" colspan="1">1.0652 (5)</td>
<td rowspan="1" colspan="1">0.0783 (12)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">0.1884</td>
<td rowspan="1" colspan="1">0.7226</td>
<td rowspan="1" colspan="1">1.0847</td>
<td rowspan="1" colspan="1">0.117*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9B</td>
<td rowspan="1" colspan="1">0.3342</td>
<td rowspan="1" colspan="1">0.7749</td>
<td rowspan="1" colspan="1">1.0862</td>
<td rowspan="1" colspan="1">0.117*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9C</td>
<td rowspan="1" colspan="1">0.3288</td>
<td rowspan="1" colspan="1">0.6440</td>
<td rowspan="1" colspan="1">1.1401</td>
<td rowspan="1" colspan="1">0.117*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.2527 (4)</td>
<td rowspan="1" colspan="1">0.7945 (3)</td>
<td rowspan="1" colspan="1">0.4504 (4)</td>
<td rowspan="1" colspan="1">0.0648 (10)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.1905</td>
<td rowspan="1" colspan="1">0.8566</td>
<td rowspan="1" colspan="1">0.3853</td>
<td rowspan="1" colspan="1">0.097*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">0.2000</td>
<td rowspan="1" colspan="1">0.7216</td>
<td rowspan="1" colspan="1">0.4246</td>
<td rowspan="1" colspan="1">0.097*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10C</td>
<td rowspan="1" colspan="1">0.3366</td>
<td rowspan="1" colspan="1">0.7886</td>
<td rowspan="1" colspan="1">0.4227</td>
<td rowspan="1" colspan="1">0.097*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.3888 (4)</td>
<td rowspan="1" colspan="1">0.9315 (3)</td>
<td rowspan="1" colspan="1">0.6748 (5)</td>
<td rowspan="1" colspan="1">0.0622 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.4216</td>
<td rowspan="1" colspan="1">0.9487</td>
<td rowspan="1" colspan="1">0.7935</td>
<td rowspan="1" colspan="1">0.093*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.3293</td>
<td rowspan="1" colspan="1">0.9950</td>
<td rowspan="1" colspan="1">0.6100</td>
<td rowspan="1" colspan="1">0.093*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11C</td>
<td rowspan="1" colspan="1">0.4718</td>
<td rowspan="1" colspan="1">0.9220</td>
<td rowspan="1" colspan="1">0.6461</td>
<td rowspan="1" colspan="1">0.093*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.5199 (2)</td>
<td rowspan="1" colspan="1">0.69242 (19)</td>
<td rowspan="1" colspan="1">0.7257 (3)</td>
<td rowspan="1" colspan="1">0.0352 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1N</td>
<td rowspan="1" colspan="1">0.559 (3)</td>
<td rowspan="1" colspan="1">0.719 (3)</td>
<td rowspan="1" colspan="1">0.660 (4)</td>
<td rowspan="1" colspan="1">0.042*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.7129 (3)</td>
<td rowspan="1" colspan="1">0.5644 (2)</td>
<td rowspan="1" colspan="1">0.8356 (3)</td>
<td rowspan="1" colspan="1">0.0406 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2N</td>
<td rowspan="1" colspan="1">0.738 (3)</td>
<td rowspan="1" colspan="1">0.583 (3)</td>
<td rowspan="1" colspan="1">0.759 (4)</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3N</td>
<td rowspan="1" colspan="1">0.742 (3)</td>
<td rowspan="1" colspan="1">0.502 (3)</td>
<td rowspan="1" colspan="1">0.900 (4)</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.49793 (8)</td>
<td rowspan="1" colspan="1">0.55753 (6)</td>
<td rowspan="1" colspan="1">0.94144 (8)</td>
<td rowspan="1" colspan="1">0.04197 (19)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.7414 (3)</td>
<td rowspan="1" colspan="1">0.7561 (2)</td>
<td rowspan="1" colspan="1">0.3383 (3)</td>
<td rowspan="1" colspan="1">0.0353 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.8440 (3)</td>
<td rowspan="1" colspan="1">0.6995 (3)</td>
<td rowspan="1" colspan="1">0.2992 (3)</td>
<td rowspan="1" colspan="1">0.0393 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H13</td>
<td rowspan="1" colspan="1">0.8915</td>
<td rowspan="1" colspan="1">0.6339</td>
<td rowspan="1" colspan="1">0.3613</td>
<td rowspan="1" colspan="1">0.047*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.8774 (3)</td>
<td rowspan="1" colspan="1">0.7387 (3)</td>
<td rowspan="1" colspan="1">0.1694 (3)</td>
<td rowspan="1" colspan="1">0.0428 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14</td>
<td rowspan="1" colspan="1">0.9470</td>
<td rowspan="1" colspan="1">0.6986</td>
<td rowspan="1" colspan="1">0.1432</td>
<td rowspan="1" colspan="1">0.051*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.8121 (3)</td>
<td rowspan="1" colspan="1">0.8343 (3)</td>
<td rowspan="1" colspan="1">0.0779 (4)</td>
<td rowspan="1" colspan="1">0.0457 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.7089 (4)</td>
<td rowspan="1" colspan="1">0.8898 (3)</td>
<td rowspan="1" colspan="1">0.1168 (4)</td>
<td rowspan="1" colspan="1">0.0533 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16</td>
<td rowspan="1" colspan="1">0.6618</td>
<td rowspan="1" colspan="1">0.9556</td>
<td rowspan="1" colspan="1">0.0547</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.6734 (3)</td>
<td rowspan="1" colspan="1">0.8509 (3)</td>
<td rowspan="1" colspan="1">0.2443 (4)</td>
<td rowspan="1" colspan="1">0.0474 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H17</td>
<td rowspan="1" colspan="1">0.6015</td>
<td rowspan="1" colspan="1">0.8898</td>
<td rowspan="1" colspan="1">0.2678</td>
<td rowspan="1" colspan="1">0.057*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.7053 (3)</td>
<td rowspan="1" colspan="1">0.7165 (2)</td>
<td rowspan="1" colspan="1">0.4803 (3)</td>
<td rowspan="1" colspan="1">0.0382 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.8510 (4)</td>
<td rowspan="1" colspan="1">0.8777 (4)</td>
<td rowspan="1" colspan="1">−0.0609 (4)</td>
<td rowspan="1" colspan="1">0.0688 (10)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19A</td>
<td rowspan="1" colspan="1">0.8263</td>
<td rowspan="1" colspan="1">0.9595</td>
<td rowspan="1" colspan="1">−0.0806</td>
<td rowspan="1" colspan="1">0.103*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19B</td>
<td rowspan="1" colspan="1">0.7981</td>
<td rowspan="1" colspan="1">0.8339</td>
<td rowspan="1" colspan="1">−0.1624</td>
<td rowspan="1" colspan="1">0.103*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19C</td>
<td rowspan="1" colspan="1">0.9541</td>
<td rowspan="1" colspan="1">0.8680</td>
<td rowspan="1" colspan="1">−0.0298</td>
<td rowspan="1" colspan="1">0.103*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.6233 (2)</td>
<td rowspan="1" colspan="1">0.77900 (19)</td>
<td rowspan="1" colspan="1">0.5192 (3)</td>
<td rowspan="1" colspan="1">0.0518 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.7604 (2)</td>
<td rowspan="1" colspan="1">0.62322 (16)</td>
<td rowspan="1" colspan="1">0.5523 (2)</td>
<td rowspan="1" colspan="1">0.0428 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e1345" sec-type="tablewrapadps"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e1357"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0372 (15)</td>
<td rowspan="1" colspan="1">0.0423 (14)</td>
<td rowspan="1" colspan="1">0.0285 (13)</td>
<td rowspan="1" colspan="1">−0.0010 (12)</td>
<td rowspan="1" colspan="1">0.0124 (11)</td>
<td rowspan="1" colspan="1">−0.0022 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0447 (17)</td>
<td rowspan="1" colspan="1">0.0600 (18)</td>
<td rowspan="1" colspan="1">0.0416 (16)</td>
<td rowspan="1" colspan="1">0.0010 (14)</td>
<td rowspan="1" colspan="1">0.0240 (14)</td>
<td rowspan="1" colspan="1">0.0026 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0452 (17)</td>
<td rowspan="1" colspan="1">0.0385 (14)</td>
<td rowspan="1" colspan="1">0.0416 (15)</td>
<td rowspan="1" colspan="1">0.0057 (13)</td>
<td rowspan="1" colspan="1">0.0193 (13)</td>
<td rowspan="1" colspan="1">0.0040 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0349 (14)</td>
<td rowspan="1" colspan="1">0.0371 (14)</td>
<td rowspan="1" colspan="1">0.0302 (13)</td>
<td rowspan="1" colspan="1">−0.0036 (11)</td>
<td rowspan="1" colspan="1">0.0125 (11)</td>
<td rowspan="1" colspan="1">−0.0062 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0367 (15)</td>
<td rowspan="1" colspan="1">0.0371 (14)</td>
<td rowspan="1" colspan="1">0.0297 (12)</td>
<td rowspan="1" colspan="1">−0.0024 (12)</td>
<td rowspan="1" colspan="1">0.0145 (11)</td>
<td rowspan="1" colspan="1">−0.0032 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.093 (3)</td>
<td rowspan="1" colspan="1">0.120 (4)</td>
<td rowspan="1" colspan="1">0.166 (5)</td>
<td rowspan="1" colspan="1">−0.062 (3)</td>
<td rowspan="1" colspan="1">0.099 (4)</td>
<td rowspan="1" colspan="1">−0.071 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.071 (3)</td>
<td rowspan="1" colspan="1">0.121 (3)</td>
<td rowspan="1" colspan="1">0.061 (2)</td>
<td rowspan="1" colspan="1">−0.016 (2)</td>
<td rowspan="1" colspan="1">0.046 (2)</td>
<td rowspan="1" colspan="1">−0.024 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.067 (2)</td>
<td rowspan="1" colspan="1">0.070 (2)</td>
<td rowspan="1" colspan="1">0.0382 (17)</td>
<td rowspan="1" colspan="1">0.0162 (19)</td>
<td rowspan="1" colspan="1">−0.0001 (16)</td>
<td rowspan="1" colspan="1">0.0003 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.078 (3)</td>
<td rowspan="1" colspan="1">0.0420 (18)</td>
<td rowspan="1" colspan="1">0.060 (2)</td>
<td rowspan="1" colspan="1">−0.0011 (17)</td>
<td rowspan="1" colspan="1">0.0206 (19)</td>
<td rowspan="1" colspan="1">0.0045 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0393 (13)</td>
<td rowspan="1" colspan="1">0.0379 (12)</td>
<td rowspan="1" colspan="1">0.0330 (11)</td>
<td rowspan="1" colspan="1">−0.0016 (10)</td>
<td rowspan="1" colspan="1">0.0193 (10)</td>
<td rowspan="1" colspan="1">0.0002 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.0422 (15)</td>
<td rowspan="1" colspan="1">0.0462 (14)</td>
<td rowspan="1" colspan="1">0.0355 (13)</td>
<td rowspan="1" colspan="1">0.0056 (12)</td>
<td rowspan="1" colspan="1">0.0176 (11)</td>
<td rowspan="1" colspan="1">0.0022 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0427 (4)</td>
<td rowspan="1" colspan="1">0.0504 (4)</td>
<td rowspan="1" colspan="1">0.0366 (3)</td>
<td rowspan="1" colspan="1">0.0040 (4)</td>
<td rowspan="1" colspan="1">0.0197 (3)</td>
<td rowspan="1" colspan="1">0.0082 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.0346 (14)</td>
<td rowspan="1" colspan="1">0.0440 (15)</td>
<td rowspan="1" colspan="1">0.0286 (12)</td>
<td rowspan="1" colspan="1">−0.0072 (12)</td>
<td rowspan="1" colspan="1">0.0138 (11)</td>
<td rowspan="1" colspan="1">−0.0075 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.0291 (14)</td>
<td rowspan="1" colspan="1">0.0486 (16)</td>
<td rowspan="1" colspan="1">0.0385 (15)</td>
<td rowspan="1" colspan="1">−0.0007 (12)</td>
<td rowspan="1" colspan="1">0.0116 (12)</td>
<td rowspan="1" colspan="1">−0.0027 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.0293 (15)</td>
<td rowspan="1" colspan="1">0.0632 (19)</td>
<td rowspan="1" colspan="1">0.0391 (15)</td>
<td rowspan="1" colspan="1">−0.0007 (14)</td>
<td rowspan="1" colspan="1">0.0171 (13)</td>
<td rowspan="1" colspan="1">−0.0070 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0437 (17)</td>
<td rowspan="1" colspan="1">0.0619 (19)</td>
<td rowspan="1" colspan="1">0.0347 (14)</td>
<td rowspan="1" colspan="1">−0.0018 (15)</td>
<td rowspan="1" colspan="1">0.0190 (13)</td>
<td rowspan="1" colspan="1">−0.0020 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.065 (2)</td>
<td rowspan="1" colspan="1">0.0589 (19)</td>
<td rowspan="1" colspan="1">0.0413 (17)</td>
<td rowspan="1" colspan="1">0.0144 (17)</td>
<td rowspan="1" colspan="1">0.0273 (16)</td>
<td rowspan="1" colspan="1">0.0111 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.0539 (19)</td>
<td rowspan="1" colspan="1">0.0529 (18)</td>
<td rowspan="1" colspan="1">0.0432 (17)</td>
<td rowspan="1" colspan="1">0.0113 (15)</td>
<td rowspan="1" colspan="1">0.0276 (15)</td>
<td rowspan="1" colspan="1">0.0007 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.0381 (15)</td>
<td rowspan="1" colspan="1">0.0422 (15)</td>
<td rowspan="1" colspan="1">0.0364 (14)</td>
<td rowspan="1" colspan="1">−0.0066 (13)</td>
<td rowspan="1" colspan="1">0.0173 (12)</td>
<td rowspan="1" colspan="1">−0.0057 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.075 (2)</td>
<td rowspan="1" colspan="1">0.095 (3)</td>
<td rowspan="1" colspan="1">0.0514 (19)</td>
<td rowspan="1" colspan="1">0.017 (2)</td>
<td rowspan="1" colspan="1">0.0410 (18)</td>
<td rowspan="1" colspan="1">0.0169 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0653 (14)</td>
<td rowspan="1" colspan="1">0.0525 (12)</td>
<td rowspan="1" colspan="1">0.0554 (13)</td>
<td rowspan="1" colspan="1">0.0081 (10)</td>
<td rowspan="1" colspan="1">0.0429 (11)</td>
<td rowspan="1" colspan="1">0.0050 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0452 (11)</td>
<td rowspan="1" colspan="1">0.0479 (11)</td>
<td rowspan="1" colspan="1">0.0386 (10)</td>
<td rowspan="1" colspan="1">−0.0012 (9)</td>
<td rowspan="1" colspan="1">0.0203 (9)</td>
<td rowspan="1" colspan="1">0.0012 (9)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e1771" sec-type="tablewrapgeomlong"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e1781"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.338 (4)</td>
<td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.502 (4)</td>
<td rowspan="1" colspan="1">C9—H9B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—S1</td>
<td rowspan="1" colspan="1">1.753 (3)</td>
<td rowspan="1" colspan="1">C9—H9C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8</td>
<td rowspan="1" colspan="1">1.509 (5)</td>
<td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B</td>
<td rowspan="1" colspan="1">1.514 (6)</td>
<td rowspan="1" colspan="1">C10—H10B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9</td>
<td rowspan="1" colspan="1">1.518 (5)</td>
<td rowspan="1" colspan="1">C10—H10C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A</td>
<td rowspan="1" colspan="1">1.626 (9)</td>
<td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A</td>
<td rowspan="1" colspan="1">1.451 (14)</td>
<td rowspan="1" colspan="1">C11—H11B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—H3A1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C11—H11C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—H3A2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">N1—H1N</td>
<td rowspan="1" colspan="1">0.88 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5</td>
<td rowspan="1" colspan="1">1.555 (9)</td>
<td rowspan="1" colspan="1">N2—H2N</td>
<td rowspan="1" colspan="1">0.83 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H4A1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">N2—H3N</td>
<td rowspan="1" colspan="1">0.89 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H4A2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C12—C17</td>
<td rowspan="1" colspan="1">1.385 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B</td>
<td rowspan="1" colspan="1">1.551 (9)</td>
<td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.389 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—H3B1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C12—C18</td>
<td rowspan="1" colspan="1">1.506 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—H3B2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.389 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5</td>
<td rowspan="1" colspan="1">1.547 (6)</td>
<td rowspan="1" colspan="1">C13—H13</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H4B1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.377 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H4B2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C14—H14</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.514 (4)</td>
<td rowspan="1" colspan="1">C15—C16</td>
<td rowspan="1" colspan="1">1.386 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11</td>
<td rowspan="1" colspan="1">1.524 (4)</td>
<td rowspan="1" colspan="1">C15—C19</td>
<td rowspan="1" colspan="1">1.510 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10</td>
<td rowspan="1" colspan="1">1.529 (4)</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.383 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1</td>
<td rowspan="1" colspan="1">1.394 (4)</td>
<td rowspan="1" colspan="1">C16—H16</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2</td>
<td rowspan="1" colspan="1">1.322 (4)</td>
<td rowspan="1" colspan="1">C17—H17</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1</td>
<td rowspan="1" colspan="1">1.325 (3)</td>
<td rowspan="1" colspan="1">C18—O1</td>
<td rowspan="1" colspan="1">1.252 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—S1</td>
<td rowspan="1" colspan="1">1.729 (3)</td>
<td rowspan="1" colspan="1">C18—O2</td>
<td rowspan="1" colspan="1">1.267 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C19—H19A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C19—H19B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C19—H19C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2</td>
<td rowspan="1" colspan="1">127.0 (3)</td>
<td rowspan="1" colspan="1">H8A—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—S1</td>
<td rowspan="1" colspan="1">110.6 (2)</td>
<td rowspan="1" colspan="1">H8B—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—S1</td>
<td rowspan="1" colspan="1">122.4 (2)</td>
<td rowspan="1" colspan="1">C2—C9—H9A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C8</td>
<td rowspan="1" colspan="1">111.6 (3)</td>
<td rowspan="1" colspan="1">C2—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3B</td>
<td rowspan="1" colspan="1">105.9 (3)</td>
<td rowspan="1" colspan="1">H9A—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3B</td>
<td rowspan="1" colspan="1">98.4 (4)</td>
<td rowspan="1" colspan="1">C2—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C9</td>
<td rowspan="1" colspan="1">110.6 (3)</td>
<td rowspan="1" colspan="1">H9A—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C9</td>
<td rowspan="1" colspan="1">108.5 (3)</td>
<td rowspan="1" colspan="1">H9B—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C2—C9</td>
<td rowspan="1" colspan="1">121.2 (4)</td>
<td rowspan="1" colspan="1">C5—C10—H10A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3A</td>
<td rowspan="1" colspan="1">103.1 (4)</td>
<td rowspan="1" colspan="1">C5—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3A</td>
<td rowspan="1" colspan="1">128.8 (5)</td>
<td rowspan="1" colspan="1">H10A—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3A</td>
<td rowspan="1" colspan="1">92.3 (4)</td>
<td rowspan="1" colspan="1">C5—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—C2</td>
<td rowspan="1" colspan="1">114.0 (8)</td>
<td rowspan="1" colspan="1">H10A—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—H3A1</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">H10B—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—H3A1</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C5—C11—H11A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—H3A2</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C5—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—H3A2</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">H11A—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A1—C3A—H3A2</td>
<td rowspan="1" colspan="1">107.7</td>
<td rowspan="1" colspan="1">C5—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5</td>
<td rowspan="1" colspan="1">110.6 (8)</td>
<td rowspan="1" colspan="1">H11A—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—H4A1</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H11B—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4A—H4A1</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C7—N1—C6</td>
<td rowspan="1" colspan="1">114.1 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—H4A2</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C7—N1—H1N</td>
<td rowspan="1" colspan="1">116 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4A—H4A2</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C6—N1—H1N</td>
<td rowspan="1" colspan="1">130.1 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A1—C4A—H4A2</td>
<td rowspan="1" colspan="1">108.1</td>
<td rowspan="1" colspan="1">C7—N2—H2N</td>
<td rowspan="1" colspan="1">116 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—C4B</td>
<td rowspan="1" colspan="1">111.3 (5)</td>
<td rowspan="1" colspan="1">C7—N2—H3N</td>
<td rowspan="1" colspan="1">115 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—H3B1</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">H2N—N2—H3N</td>
<td rowspan="1" colspan="1">126 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—H3B1</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C7—S1—C1</td>
<td rowspan="1" colspan="1">90.27 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—H3B2</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C17—C12—C13</td>
<td rowspan="1" colspan="1">118.4 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—H3B2</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C17—C12—C18</td>
<td rowspan="1" colspan="1">120.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B1—C3B—H3B2</td>
<td rowspan="1" colspan="1">108.0</td>
<td rowspan="1" colspan="1">C13—C12—C18</td>
<td rowspan="1" colspan="1">121.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—C3B</td>
<td rowspan="1" colspan="1">113.0 (5)</td>
<td rowspan="1" colspan="1">C14—C13—C12</td>
<td rowspan="1" colspan="1">120.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—H4B1</td>
<td rowspan="1" colspan="1">109.0</td>
<td rowspan="1" colspan="1">C14—C13—H13</td>
<td rowspan="1" colspan="1">119.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—H4B1</td>
<td rowspan="1" colspan="1">109.0</td>
<td rowspan="1" colspan="1">C12—C13—H13</td>
<td rowspan="1" colspan="1">119.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—H4B2</td>
<td rowspan="1" colspan="1">109.0</td>
<td rowspan="1" colspan="1">C15—C14—C13</td>
<td rowspan="1" colspan="1">121.6 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—H4B2</td>
<td rowspan="1" colspan="1">109.0</td>
<td rowspan="1" colspan="1">C15—C14—H14</td>
<td rowspan="1" colspan="1">119.2</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B1—C4B—H4B2</td>
<td rowspan="1" colspan="1">107.8</td>
<td rowspan="1" colspan="1">C13—C14—H14</td>
<td rowspan="1" colspan="1">119.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C11</td>
<td rowspan="1" colspan="1">109.8 (2)</td>
<td rowspan="1" colspan="1">C14—C15—C16</td>
<td rowspan="1" colspan="1">117.9 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C10</td>
<td rowspan="1" colspan="1">109.8 (2)</td>
<td rowspan="1" colspan="1">C14—C15—C19</td>
<td rowspan="1" colspan="1">121.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C10</td>
<td rowspan="1" colspan="1">108.7 (3)</td>
<td rowspan="1" colspan="1">C16—C15—C19</td>
<td rowspan="1" colspan="1">120.8 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4B</td>
<td rowspan="1" colspan="1">106.5 (3)</td>
<td rowspan="1" colspan="1">C17—C16—C15</td>
<td rowspan="1" colspan="1">121.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C4B</td>
<td rowspan="1" colspan="1">103.1 (4)</td>
<td rowspan="1" colspan="1">C17—C16—H16</td>
<td rowspan="1" colspan="1">119.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C4B</td>
<td rowspan="1" colspan="1">118.6 (4)</td>
<td rowspan="1" colspan="1">C15—C16—H16</td>
<td rowspan="1" colspan="1">119.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4A</td>
<td rowspan="1" colspan="1">107.9 (4)</td>
<td rowspan="1" colspan="1">C16—C17—C12</td>
<td rowspan="1" colspan="1">120.8 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C4A</td>
<td rowspan="1" colspan="1">121.6 (5)</td>
<td rowspan="1" colspan="1">C16—C17—H17</td>
<td rowspan="1" colspan="1">119.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C4A</td>
<td rowspan="1" colspan="1">98.1 (5)</td>
<td rowspan="1" colspan="1">C12—C17—H17</td>
<td rowspan="1" colspan="1">119.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1</td>
<td rowspan="1" colspan="1">113.5 (2)</td>
<td rowspan="1" colspan="1">O1—C18—O2</td>
<td rowspan="1" colspan="1">124.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—C5</td>
<td rowspan="1" colspan="1">125.6 (3)</td>
<td rowspan="1" colspan="1">O1—C18—C12</td>
<td rowspan="1" colspan="1">117.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C6—C5</td>
<td rowspan="1" colspan="1">121.0 (2)</td>
<td rowspan="1" colspan="1">O2—C18—C12</td>
<td rowspan="1" colspan="1">117.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1</td>
<td rowspan="1" colspan="1">124.6 (2)</td>
<td rowspan="1" colspan="1">C15—C19—H19A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1</td>
<td rowspan="1" colspan="1">123.9 (2)</td>
<td rowspan="1" colspan="1">C15—C19—H19B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C7—S1</td>
<td rowspan="1" colspan="1">111.6 (2)</td>
<td rowspan="1" colspan="1">H19A—C19—H19B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C15—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H19A—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H19B—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2554" sec-type="tablewraphbondslong"><label>2-Amino-4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-3-ium
4-methylbenzoate (I) </label>
<title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e2563"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H</td>
<td rowspan="1" colspan="1">H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1<italic>N</italic>
···O1</td>
<td rowspan="1" colspan="1">0.88 (3)</td>
<td rowspan="1" colspan="1">1.76 (3)</td>
<td rowspan="1" colspan="1">2.632 (3)</td>
<td rowspan="1" colspan="1">175 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2<italic>N</italic>
···O2</td>
<td rowspan="1" colspan="1">0.83 (3)</td>
<td rowspan="1" colspan="1">1.98 (4)</td>
<td rowspan="1" colspan="1">2.801 (3)</td>
<td rowspan="1" colspan="1">170 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3<italic>N</italic>
···O2<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.89 (3)</td>
<td rowspan="1" colspan="1">1.93 (3)</td>
<td rowspan="1" colspan="1">2.805 (3)</td>
<td rowspan="1" colspan="1">164 (3)</td>
</tr>
</table>
</table-wrap>
<p>Symmetry code: (i) <italic>x</italic>
, −<italic>y</italic>
+1, <italic>z</italic>
+1/2.</p>
</sec>
<sec id="d1e2670" sec-type="tablewrapcrystaldatalong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e2679"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>−</sup>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 424</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 411.35</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.424 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 10.2506 (5) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 6835 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 11.5855 (4) Å</td>
<td rowspan="1" colspan="1">θ = 2.2–28.2°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 8.8269 (4) Å</td>
<td rowspan="1" colspan="1">µ = 2.26 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 113.807 (6)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 173 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 959.07 (8) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">Plate, colourless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 2</td>
<td rowspan="1" colspan="1">0.12 × 0.08 × 0.02 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2805" sec-type="tablewrapdatacollectionlong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e2814"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Rigaku XtaLAB P200 HPC diffractometer</td>
<td rowspan="1" colspan="1">3993 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: rotating anode, Rigaku FR-X</td>
<td rowspan="1" colspan="1">3311 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Rigaku Osmic Confocal Optical System monochromator</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.026</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 29.1°, θ<sub>min</sub>
 = 2.2°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −13→13</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.761, <italic>T</italic>
<sub>max</sub>
 = 1.000</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −15→15</td>
</tr>
<tr><td rowspan="1" colspan="1">12220 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −10→11</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2916" sec-type="tablewraprefinementdatalong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e2925"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Hydrogen site location: mixed</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.032</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0407<italic>P</italic>
)<sup>2</sup>
 + 0.0111<italic>P</italic>
] where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.083</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 = 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.06</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.62 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">3993 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.38 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">230 parameters</td>
<td rowspan="1" colspan="1">Absolute structure: Flack <italic>x</italic> determined using 1344 quotients
[(<italic>I</italic>
<sup>+</sup>
)-(<italic>I</italic>
<sup>-</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>-</sup>)]
(Parsons <italic>et al.</italic>
, 2013).</td>
</tr>
<tr><td rowspan="1" colspan="1">2 restraints</td>
<td rowspan="1" colspan="1">Absolute structure parameter: 0.005 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e3103" sec-type="specialdetails"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e3113"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e3122" sec-type="tablewrapcoords"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e3134"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.6357 (4)</td>
<td rowspan="1" colspan="1">0.6587 (3)</td>
<td rowspan="1" colspan="1">0.1418 (5)</td>
<td rowspan="1" colspan="1">0.0359 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.7655 (5)</td>
<td rowspan="1" colspan="1">0.6679 (4)</td>
<td rowspan="1" colspan="1">0.1027 (5)</td>
<td rowspan="1" colspan="1">0.0446 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.8711 (8)</td>
<td rowspan="1" colspan="1">0.7399 (8)</td>
<td rowspan="1" colspan="1">0.2385 (10)</td>
<td rowspan="1" colspan="1">0.113 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3A</td>
<td rowspan="1" colspan="1">0.9213</td>
<td rowspan="1" colspan="1">0.6883</td>
<td rowspan="1" colspan="1">0.3338</td>
<td rowspan="1" colspan="1">0.136*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3B</td>
<td rowspan="1" colspan="1">0.9431</td>
<td rowspan="1" colspan="1">0.7681</td>
<td rowspan="1" colspan="1">0.1991</td>
<td rowspan="1" colspan="1">0.136*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.8218 (6)</td>
<td rowspan="1" colspan="1">0.8359 (5)</td>
<td rowspan="1" colspan="1">0.2982 (9)</td>
<td rowspan="1" colspan="1">0.0780 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4A</td>
<td rowspan="1" colspan="1">0.7931</td>
<td rowspan="1" colspan="1">0.8956</td>
<td rowspan="1" colspan="1">0.2105</td>
<td rowspan="1" colspan="1">0.094*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4B</td>
<td rowspan="1" colspan="1">0.9040</td>
<td rowspan="1" colspan="1">0.8673</td>
<td rowspan="1" colspan="1">0.3937</td>
<td rowspan="1" colspan="1">0.094*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.6976 (4)</td>
<td rowspan="1" colspan="1">0.8213 (3)</td>
<td rowspan="1" colspan="1">0.3532 (5)</td>
<td rowspan="1" colspan="1">0.0403 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.6067 (4)</td>
<td rowspan="1" colspan="1">0.7238 (3)</td>
<td rowspan="1" colspan="1">0.2502 (5)</td>
<td rowspan="1" colspan="1">0.0339 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.4084 (4)</td>
<td rowspan="1" colspan="1">0.6086 (3)</td>
<td rowspan="1" colspan="1">0.1598 (5)</td>
<td rowspan="1" colspan="1">0.0345 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.8389 (8)</td>
<td rowspan="1" colspan="1">0.5492 (7)</td>
<td rowspan="1" colspan="1">0.1190 (12)</td>
<td rowspan="1" colspan="1">0.110 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.9299</td>
<td rowspan="1" colspan="1">0.5590</td>
<td rowspan="1" colspan="1">0.1087</td>
<td rowspan="1" colspan="1">0.164*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">0.7771</td>
<td rowspan="1" colspan="1">0.4976</td>
<td rowspan="1" colspan="1">0.0314</td>
<td rowspan="1" colspan="1">0.164*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8C</td>
<td rowspan="1" colspan="1">0.8561</td>
<td rowspan="1" colspan="1">0.5156</td>
<td rowspan="1" colspan="1">0.2274</td>
<td rowspan="1" colspan="1">0.164*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.7278 (7)</td>
<td rowspan="1" colspan="1">0.7092 (6)</td>
<td rowspan="1" colspan="1">−0.0719 (7)</td>
<td rowspan="1" colspan="1">0.0772 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">0.8147</td>
<td rowspan="1" colspan="1">0.7152</td>
<td rowspan="1" colspan="1">−0.0923</td>
<td rowspan="1" colspan="1">0.116*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9B</td>
<td rowspan="1" colspan="1">0.6820</td>
<td rowspan="1" colspan="1">0.7850</td>
<td rowspan="1" colspan="1">−0.0868</td>
<td rowspan="1" colspan="1">0.116*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9C</td>
<td rowspan="1" colspan="1">0.6622</td>
<td rowspan="1" colspan="1">0.6541</td>
<td rowspan="1" colspan="1">−0.1501</td>
<td rowspan="1" colspan="1">0.116*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.7484 (6)</td>
<td rowspan="1" colspan="1">0.7930 (5)</td>
<td rowspan="1" colspan="1">0.5371 (6)</td>
<td rowspan="1" colspan="1">0.0664 (14)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.8122</td>
<td rowspan="1" colspan="1">0.8542</td>
<td rowspan="1" colspan="1">0.6028</td>
<td rowspan="1" colspan="1">0.100*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">0.7995</td>
<td rowspan="1" colspan="1">0.7193</td>
<td rowspan="1" colspan="1">0.5604</td>
<td rowspan="1" colspan="1">0.100*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10C</td>
<td rowspan="1" colspan="1">0.6659</td>
<td rowspan="1" colspan="1">0.7875</td>
<td rowspan="1" colspan="1">0.5663</td>
<td rowspan="1" colspan="1">0.100*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.6095 (6)</td>
<td rowspan="1" colspan="1">0.9320 (4)</td>
<td rowspan="1" colspan="1">0.3150 (6)</td>
<td rowspan="1" colspan="1">0.0578 (12)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.5714</td>
<td rowspan="1" colspan="1">0.9473</td>
<td rowspan="1" colspan="1">0.1957</td>
<td rowspan="1" colspan="1">0.087*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.6699</td>
<td rowspan="1" colspan="1">0.9966</td>
<td rowspan="1" colspan="1">0.3751</td>
<td rowspan="1" colspan="1">0.087*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11C</td>
<td rowspan="1" colspan="1">0.5304</td>
<td rowspan="1" colspan="1">0.9231</td>
<td rowspan="1" colspan="1">0.3496</td>
<td rowspan="1" colspan="1">0.087*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.4781 (3)</td>
<td rowspan="1" colspan="1">0.6939 (3)</td>
<td rowspan="1" colspan="1">0.2604 (4)</td>
<td rowspan="1" colspan="1">0.0348 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1N</td>
<td rowspan="1" colspan="1">0.441 (5)</td>
<td rowspan="1" colspan="1">0.732 (4)</td>
<td rowspan="1" colspan="1">0.339 (5)</td>
<td rowspan="1" colspan="1">0.042*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.2855 (4)</td>
<td rowspan="1" colspan="1">0.5667 (3)</td>
<td rowspan="1" colspan="1">0.1482 (5)</td>
<td rowspan="1" colspan="1">0.0408 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2N</td>
<td rowspan="1" colspan="1">0.257 (6)</td>
<td rowspan="1" colspan="1">0.582 (4)</td>
<td rowspan="1" colspan="1">0.208 (6)</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3N</td>
<td rowspan="1" colspan="1">0.264 (5)</td>
<td rowspan="1" colspan="1">0.505 (4)</td>
<td rowspan="1" colspan="1">0.086 (6)</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.49893 (11)</td>
<td rowspan="1" colspan="1">0.55873 (9)</td>
<td rowspan="1" colspan="1">0.04481 (11)</td>
<td rowspan="1" colspan="1">0.0398 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.2601 (4)</td>
<td rowspan="1" colspan="1">0.7536 (3)</td>
<td rowspan="1" colspan="1">0.6483 (4)</td>
<td rowspan="1" colspan="1">0.0352 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.1566 (4)</td>
<td rowspan="1" colspan="1">0.6980 (3)</td>
<td rowspan="1" colspan="1">0.6846 (5)</td>
<td rowspan="1" colspan="1">0.0369 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H13</td>
<td rowspan="1" colspan="1">0.1094</td>
<td rowspan="1" colspan="1">0.6326</td>
<td rowspan="1" colspan="1">0.6213</td>
<td rowspan="1" colspan="1">0.044*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.1208 (4)</td>
<td rowspan="1" colspan="1">0.7360 (4)</td>
<td rowspan="1" colspan="1">0.8116 (5)</td>
<td rowspan="1" colspan="1">0.0422 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14</td>
<td rowspan="1" colspan="1">0.0501</td>
<td rowspan="1" colspan="1">0.6970</td>
<td rowspan="1" colspan="1">0.8361</td>
<td rowspan="1" colspan="1">0.051*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.1893 (4)</td>
<td rowspan="1" colspan="1">0.8310 (4)</td>
<td rowspan="1" colspan="1">0.9017 (5)</td>
<td rowspan="1" colspan="1">0.0402 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.2946 (5)</td>
<td rowspan="1" colspan="1">0.8860 (3)</td>
<td rowspan="1" colspan="1">0.8709 (6)</td>
<td rowspan="1" colspan="1">0.0490 (11)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16</td>
<td rowspan="1" colspan="1">0.3434</td>
<td rowspan="1" colspan="1">0.9499</td>
<td rowspan="1" colspan="1">0.9369</td>
<td rowspan="1" colspan="1">0.059*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.3291 (5)</td>
<td rowspan="1" colspan="1">0.8481 (4)</td>
<td rowspan="1" colspan="1">0.7443 (5)</td>
<td rowspan="1" colspan="1">0.0466 (10)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H17</td>
<td rowspan="1" colspan="1">0.4009</td>
<td rowspan="1" colspan="1">0.8871</td>
<td rowspan="1" colspan="1">0.7220</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.2979 (4)</td>
<td rowspan="1" colspan="1">0.7141 (3)</td>
<td rowspan="1" colspan="1">0.5095 (5)</td>
<td rowspan="1" colspan="1">0.0370 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.3836 (4)</td>
<td rowspan="1" colspan="1">0.7755 (3)</td>
<td rowspan="1" colspan="1">0.4748 (4)</td>
<td rowspan="1" colspan="1">0.0505 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.2410 (3)</td>
<td rowspan="1" colspan="1">0.6225 (2)</td>
<td rowspan="1" colspan="1">0.4343 (4)</td>
<td rowspan="1" colspan="1">0.0419 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">Br1</td>
<td rowspan="1" colspan="1">0.13945 (5)</td>
<td rowspan="1" colspan="1">0.88476 (4)</td>
<td rowspan="1" colspan="1">1.07398 (5)</td>
<td rowspan="1" colspan="1">0.0676 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e3734" sec-type="tablewrapadps"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e3746"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">0.0392 (18)</td>
<td rowspan="1" colspan="1">0.0320 (18)</td>
<td rowspan="1" colspan="1">0.0012 (17)</td>
<td rowspan="1" colspan="1">0.0138 (17)</td>
<td rowspan="1" colspan="1">0.0030 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.043 (2)</td>
<td rowspan="1" colspan="1">0.057 (2)</td>
<td rowspan="1" colspan="1">0.040 (2)</td>
<td rowspan="1" colspan="1">−0.004 (2)</td>
<td rowspan="1" colspan="1">0.0238 (19)</td>
<td rowspan="1" colspan="1">−0.0023 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.087 (5)</td>
<td rowspan="1" colspan="1">0.160 (7)</td>
<td rowspan="1" colspan="1">0.120 (6)</td>
<td rowspan="1" colspan="1">−0.057 (5)</td>
<td rowspan="1" colspan="1">0.071 (5)</td>
<td rowspan="1" colspan="1">−0.073 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.061 (3)</td>
<td rowspan="1" colspan="1">0.080 (3)</td>
<td rowspan="1" colspan="1">0.109 (5)</td>
<td rowspan="1" colspan="1">−0.032 (3)</td>
<td rowspan="1" colspan="1">0.050 (3)</td>
<td rowspan="1" colspan="1">−0.039 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">0.0370 (19)</td>
<td rowspan="1" colspan="1">0.043 (2)</td>
<td rowspan="1" colspan="1">−0.0060 (17)</td>
<td rowspan="1" colspan="1">0.0129 (17)</td>
<td rowspan="1" colspan="1">−0.0009 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.036 (2)</td>
<td rowspan="1" colspan="1">0.0329 (18)</td>
<td rowspan="1" colspan="1">0.0323 (18)</td>
<td rowspan="1" colspan="1">0.0019 (16)</td>
<td rowspan="1" colspan="1">0.0131 (16)</td>
<td rowspan="1" colspan="1">0.0038 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">0.0365 (19)</td>
<td rowspan="1" colspan="1">0.0293 (18)</td>
<td rowspan="1" colspan="1">0.0022 (17)</td>
<td rowspan="1" colspan="1">0.0123 (16)</td>
<td rowspan="1" colspan="1">0.0043 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.091 (5)</td>
<td rowspan="1" colspan="1">0.109 (5)</td>
<td rowspan="1" colspan="1">0.167 (8)</td>
<td rowspan="1" colspan="1">0.055 (5)</td>
<td rowspan="1" colspan="1">0.092 (6)</td>
<td rowspan="1" colspan="1">0.064 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.074 (4)</td>
<td rowspan="1" colspan="1">0.113 (4)</td>
<td rowspan="1" colspan="1">0.058 (3)</td>
<td rowspan="1" colspan="1">0.020 (3)</td>
<td rowspan="1" colspan="1">0.040 (3)</td>
<td rowspan="1" colspan="1">0.028 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.071 (3)</td>
<td rowspan="1" colspan="1">0.066 (3)</td>
<td rowspan="1" colspan="1">0.039 (2)</td>
<td rowspan="1" colspan="1">−0.016 (3)</td>
<td rowspan="1" colspan="1">−0.002 (2)</td>
<td rowspan="1" colspan="1">−0.001 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.072 (3)</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">0.059 (3)</td>
<td rowspan="1" colspan="1">0.003 (2)</td>
<td rowspan="1" colspan="1">0.022 (3)</td>
<td rowspan="1" colspan="1">−0.001 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0359 (18)</td>
<td rowspan="1" colspan="1">0.0375 (16)</td>
<td rowspan="1" colspan="1">0.0333 (17)</td>
<td rowspan="1" colspan="1">0.0013 (14)</td>
<td rowspan="1" colspan="1">0.0163 (14)</td>
<td rowspan="1" colspan="1">−0.0001 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.042 (2)</td>
<td rowspan="1" colspan="1">0.0461 (19)</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">−0.0047 (17)</td>
<td rowspan="1" colspan="1">0.0190 (16)</td>
<td rowspan="1" colspan="1">−0.0057 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0407 (5)</td>
<td rowspan="1" colspan="1">0.0451 (5)</td>
<td rowspan="1" colspan="1">0.0352 (5)</td>
<td rowspan="1" colspan="1">−0.0029 (5)</td>
<td rowspan="1" colspan="1">0.0168 (4)</td>
<td rowspan="1" colspan="1">−0.0061 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.034 (2)</td>
<td rowspan="1" colspan="1">0.0390 (19)</td>
<td rowspan="1" colspan="1">0.0305 (19)</td>
<td rowspan="1" colspan="1">0.0064 (16)</td>
<td rowspan="1" colspan="1">0.0109 (16)</td>
<td rowspan="1" colspan="1">0.0081 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.030 (2)</td>
<td rowspan="1" colspan="1">0.0416 (19)</td>
<td rowspan="1" colspan="1">0.036 (2)</td>
<td rowspan="1" colspan="1">−0.0015 (16)</td>
<td rowspan="1" colspan="1">0.0102 (16)</td>
<td rowspan="1" colspan="1">−0.0011 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.030 (2)</td>
<td rowspan="1" colspan="1">0.056 (2)</td>
<td rowspan="1" colspan="1">0.041 (2)</td>
<td rowspan="1" colspan="1">0.0004 (19)</td>
<td rowspan="1" colspan="1">0.0153 (18)</td>
<td rowspan="1" colspan="1">0.0030 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.042 (2)</td>
<td rowspan="1" colspan="1">0.050 (2)</td>
<td rowspan="1" colspan="1">0.0308 (19)</td>
<td rowspan="1" colspan="1">0.0041 (19)</td>
<td rowspan="1" colspan="1">0.0170 (18)</td>
<td rowspan="1" colspan="1">0.0051 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.060 (3)</td>
<td rowspan="1" colspan="1">0.050 (2)</td>
<td rowspan="1" colspan="1">0.039 (2)</td>
<td rowspan="1" colspan="1">−0.012 (2)</td>
<td rowspan="1" colspan="1">0.023 (2)</td>
<td rowspan="1" colspan="1">−0.0053 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.055 (3)</td>
<td rowspan="1" colspan="1">0.049 (2)</td>
<td rowspan="1" colspan="1">0.042 (2)</td>
<td rowspan="1" colspan="1">−0.010 (2)</td>
<td rowspan="1" colspan="1">0.026 (2)</td>
<td rowspan="1" colspan="1">0.0014 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.036 (2)</td>
<td rowspan="1" colspan="1">0.040 (2)</td>
<td rowspan="1" colspan="1">0.035 (2)</td>
<td rowspan="1" colspan="1">0.0061 (18)</td>
<td rowspan="1" colspan="1">0.0153 (17)</td>
<td rowspan="1" colspan="1">0.0025 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.060 (2)</td>
<td rowspan="1" colspan="1">0.0519 (16)</td>
<td rowspan="1" colspan="1">0.0526 (18)</td>
<td rowspan="1" colspan="1">−0.0091 (15)</td>
<td rowspan="1" colspan="1">0.0365 (16)</td>
<td rowspan="1" colspan="1">−0.0072 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0422 (16)</td>
<td rowspan="1" colspan="1">0.0477 (16)</td>
<td rowspan="1" colspan="1">0.0367 (15)</td>
<td rowspan="1" colspan="1">0.0025 (13)</td>
<td rowspan="1" colspan="1">0.0168 (12)</td>
<td rowspan="1" colspan="1">−0.0012 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">Br1</td>
<td rowspan="1" colspan="1">0.0863 (4)</td>
<td rowspan="1" colspan="1">0.0796 (3)</td>
<td rowspan="1" colspan="1">0.0542 (3)</td>
<td rowspan="1" colspan="1">−0.0123 (3)</td>
<td rowspan="1" colspan="1">0.0462 (3)</td>
<td rowspan="1" colspan="1">−0.0134 (3)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e4196" sec-type="tablewrapgeomlong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e4206"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.342 (5)</td>
<td rowspan="1" colspan="1">C9—H9C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.508 (6)</td>
<td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—S1</td>
<td rowspan="1" colspan="1">1.752 (4)</td>
<td rowspan="1" colspan="1">C10—H10B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.503 (8)</td>
<td rowspan="1" colspan="1">C10—H10C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9</td>
<td rowspan="1" colspan="1">1.507 (7)</td>
<td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8</td>
<td rowspan="1" colspan="1">1.546 (8)</td>
<td rowspan="1" colspan="1">C11—H11B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.408 (10)</td>
<td rowspan="1" colspan="1">C11—H11C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3A</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">N1—H1N</td>
<td rowspan="1" colspan="1">1.01 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3B</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">N2—H2N</td>
<td rowspan="1" colspan="1">0.72 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.544 (7)</td>
<td rowspan="1" colspan="1">N2—H3N</td>
<td rowspan="1" colspan="1">0.88 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4A</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.385 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4B</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C12—C17</td>
<td rowspan="1" colspan="1">1.391 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.513 (6)</td>
<td rowspan="1" colspan="1">C12—C18</td>
<td rowspan="1" colspan="1">1.498 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11</td>
<td rowspan="1" colspan="1">1.526 (6)</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.385 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10</td>
<td rowspan="1" colspan="1">1.528 (6)</td>
<td rowspan="1" colspan="1">C13—H13</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1</td>
<td rowspan="1" colspan="1">1.400 (5)</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.374 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2</td>
<td rowspan="1" colspan="1">1.316 (5)</td>
<td rowspan="1" colspan="1">C14—H14</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1</td>
<td rowspan="1" colspan="1">1.327 (5)</td>
<td rowspan="1" colspan="1">C15—C16</td>
<td rowspan="1" colspan="1">1.371 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—S1</td>
<td rowspan="1" colspan="1">1.728 (4)</td>
<td rowspan="1" colspan="1">C15—Br1</td>
<td rowspan="1" colspan="1">1.895 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.373 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C16—H16</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C17—H17</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C18—O1</td>
<td rowspan="1" colspan="1">1.260 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C18—O2</td>
<td rowspan="1" colspan="1">1.263 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2</td>
<td rowspan="1" colspan="1">126.4 (4)</td>
<td rowspan="1" colspan="1">H9A—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—S1</td>
<td rowspan="1" colspan="1">110.8 (3)</td>
<td rowspan="1" colspan="1">H9B—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—S1</td>
<td rowspan="1" colspan="1">122.7 (3)</td>
<td rowspan="1" colspan="1">C5—C10—H10A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—C9</td>
<td rowspan="1" colspan="1">116.4 (5)</td>
<td rowspan="1" colspan="1">C5—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—C1</td>
<td rowspan="1" colspan="1">105.9 (4)</td>
<td rowspan="1" colspan="1">H10A—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C1</td>
<td rowspan="1" colspan="1">111.8 (4)</td>
<td rowspan="1" colspan="1">C5—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—C8</td>
<td rowspan="1" colspan="1">104.7 (6)</td>
<td rowspan="1" colspan="1">H10A—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C8</td>
<td rowspan="1" colspan="1">107.0 (5)</td>
<td rowspan="1" colspan="1">H10B—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C8</td>
<td rowspan="1" colspan="1">110.9 (4)</td>
<td rowspan="1" colspan="1">C5—C11—H11A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—C2</td>
<td rowspan="1" colspan="1">119.0 (6)</td>
<td rowspan="1" colspan="1">C5—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3A</td>
<td rowspan="1" colspan="1">107.6</td>
<td rowspan="1" colspan="1">H11A—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3A</td>
<td rowspan="1" colspan="1">107.6</td>
<td rowspan="1" colspan="1">C5—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3B</td>
<td rowspan="1" colspan="1">107.6</td>
<td rowspan="1" colspan="1">H11A—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3B</td>
<td rowspan="1" colspan="1">107.6</td>
<td rowspan="1" colspan="1">H11B—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A—C3—H3B</td>
<td rowspan="1" colspan="1">107.0</td>
<td rowspan="1" colspan="1">C7—N1—C6</td>
<td rowspan="1" colspan="1">114.0 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5</td>
<td rowspan="1" colspan="1">119.8 (5)</td>
<td rowspan="1" colspan="1">C7—N1—H1N</td>
<td rowspan="1" colspan="1">122 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4A</td>
<td rowspan="1" colspan="1">107.4</td>
<td rowspan="1" colspan="1">C6—N1—H1N</td>
<td rowspan="1" colspan="1">124 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—H4A</td>
<td rowspan="1" colspan="1">107.4</td>
<td rowspan="1" colspan="1">C7—N2—H2N</td>
<td rowspan="1" colspan="1">121 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4B</td>
<td rowspan="1" colspan="1">107.4</td>
<td rowspan="1" colspan="1">C7—N2—H3N</td>
<td rowspan="1" colspan="1">110 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—H4B</td>
<td rowspan="1" colspan="1">107.4</td>
<td rowspan="1" colspan="1">H2N—N2—H3N</td>
<td rowspan="1" colspan="1">126 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A—C4—H4B</td>
<td rowspan="1" colspan="1">106.9</td>
<td rowspan="1" colspan="1">C7—S1—C1</td>
<td rowspan="1" colspan="1">90.29 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C11</td>
<td rowspan="1" colspan="1">109.2 (3)</td>
<td rowspan="1" colspan="1">C13—C12—C17</td>
<td rowspan="1" colspan="1">118.3 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C10</td>
<td rowspan="1" colspan="1">110.0 (3)</td>
<td rowspan="1" colspan="1">C13—C12—C18</td>
<td rowspan="1" colspan="1">121.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C10</td>
<td rowspan="1" colspan="1">109.4 (4)</td>
<td rowspan="1" colspan="1">C17—C12—C18</td>
<td rowspan="1" colspan="1">120.2 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4</td>
<td rowspan="1" colspan="1">106.2 (4)</td>
<td rowspan="1" colspan="1">C14—C13—C12</td>
<td rowspan="1" colspan="1">121.2 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C4</td>
<td rowspan="1" colspan="1">109.2 (4)</td>
<td rowspan="1" colspan="1">C14—C13—H13</td>
<td rowspan="1" colspan="1">119.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C4</td>
<td rowspan="1" colspan="1">112.8 (5)</td>
<td rowspan="1" colspan="1">C12—C13—H13</td>
<td rowspan="1" colspan="1">119.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1</td>
<td rowspan="1" colspan="1">113.1 (3)</td>
<td rowspan="1" colspan="1">C15—C14—C13</td>
<td rowspan="1" colspan="1">118.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—C5</td>
<td rowspan="1" colspan="1">126.0 (3)</td>
<td rowspan="1" colspan="1">C15—C14—H14</td>
<td rowspan="1" colspan="1">120.6</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C6—C5</td>
<td rowspan="1" colspan="1">120.9 (3)</td>
<td rowspan="1" colspan="1">C13—C14—H14</td>
<td rowspan="1" colspan="1">120.6</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1</td>
<td rowspan="1" colspan="1">124.5 (4)</td>
<td rowspan="1" colspan="1">C16—C15—C14</td>
<td rowspan="1" colspan="1">121.2 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1</td>
<td rowspan="1" colspan="1">123.7 (3)</td>
<td rowspan="1" colspan="1">C16—C15—Br1</td>
<td rowspan="1" colspan="1">119.7 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C7—S1</td>
<td rowspan="1" colspan="1">111.7 (3)</td>
<td rowspan="1" colspan="1">C14—C15—Br1</td>
<td rowspan="1" colspan="1">119.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C15—C16—C17</td>
<td rowspan="1" colspan="1">119.6 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C15—C16—H16</td>
<td rowspan="1" colspan="1">120.2</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C17—C16—H16</td>
<td rowspan="1" colspan="1">120.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C17—C12</td>
<td rowspan="1" colspan="1">120.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C17—H17</td>
<td rowspan="1" colspan="1">119.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8B—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C12—C17—H17</td>
<td rowspan="1" colspan="1">119.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O1—C18—O2</td>
<td rowspan="1" colspan="1">124.5 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O1—C18—C12</td>
<td rowspan="1" colspan="1">117.5 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O2—C18—C12</td>
<td rowspan="1" colspan="1">118.0 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e4825" sec-type="tablewraphbondslong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
4-bromobenzoate (II) </label>
<title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e4834"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H</td>
<td rowspan="1" colspan="1">H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1<italic>N</italic>
···O1</td>
<td rowspan="1" colspan="1">1.01 (5)</td>
<td rowspan="1" colspan="1">1.62 (5)</td>
<td rowspan="1" colspan="1">2.626 (4)</td>
<td rowspan="1" colspan="1">172 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2<italic>N</italic>
···O2</td>
<td rowspan="1" colspan="1">0.72 (5)</td>
<td rowspan="1" colspan="1">2.12 (5)</td>
<td rowspan="1" colspan="1">2.816 (5)</td>
<td rowspan="1" colspan="1">162 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3<italic>N</italic>
···O2<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.88 (5)</td>
<td rowspan="1" colspan="1">1.94 (5)</td>
<td rowspan="1" colspan="1">2.808 (5)</td>
<td rowspan="1" colspan="1">170 (4)</td>
</tr>
</table>
</table-wrap>
<p>Symmetry code: (i) <italic>x</italic>
, −<italic>y</italic>
+1, <italic>z</italic>
−1/2.</p>
</sec>
<sec id="d1e4943" sec-type="tablewrapcrystaldatalong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e4952"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>−</sup>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 888</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 422.45</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.398 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>n</italic>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 17.3232 (6) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 10667 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 5.84087 (17) Å</td>
<td rowspan="1" colspan="1">θ = 2.0–27.8°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 21.0876 (8) Å</td>
<td rowspan="1" colspan="1">µ = 0.21 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 109.875 (4)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 173 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 2006.60 (12) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">Plate, colourless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 4</td>
<td rowspan="1" colspan="1">0.27 × 0.10 × 0.03 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e5085" sec-type="tablewrapdatacollectionlong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e5094"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Rigaku XtaLAB P200 HPC diffractometer</td>
<td rowspan="1" colspan="1">4698 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: rotating anode, Rigaku FR-X</td>
<td rowspan="1" colspan="1">3712 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Rigaku Osmic Confocal Optical System monochromator</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.056</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 29.2°, θ<sub>min</sub>
 = 1.9°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −21→23</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.566, <italic>T</italic>
<sub>max</sub>
 = 1.000</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −7→7</td>
</tr>
<tr><td rowspan="1" colspan="1">25034 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −26→26</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e5196" sec-type="tablewraprefinementdatalong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e5205"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">Hydrogen site location: mixed</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.042</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.116</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0567<italic>P</italic>
)<sup>2</sup>
 + 0.5151<italic>P</italic>
] where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.05</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 < 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1">4698 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.49 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">275 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.25 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">0 restraints</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e5351" sec-type="specialdetails"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e5361"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e5370" sec-type="tablewrapcoords"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e5382"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.26545 (9)</td>
<td rowspan="1" colspan="1">0.4584 (3)</td>
<td rowspan="1" colspan="1">0.49126 (7)</td>
<td rowspan="1" colspan="1">0.0264 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.19150 (9)</td>
<td rowspan="1" colspan="1">0.3629 (3)</td>
<td rowspan="1" colspan="1">0.50428 (8)</td>
<td rowspan="1" colspan="1">0.0298 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.13800 (10)</td>
<td rowspan="1" colspan="1">0.2456 (3)</td>
<td rowspan="1" colspan="1">0.43879 (9)</td>
<td rowspan="1" colspan="1">0.0419 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3A</td>
<td rowspan="1" colspan="1">0.0996</td>
<td rowspan="1" colspan="1">0.1392</td>
<td rowspan="1" colspan="1">0.4494</td>
<td rowspan="1" colspan="1">0.050*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3B</td>
<td rowspan="1" colspan="1">0.1048</td>
<td rowspan="1" colspan="1">0.3636</td>
<td rowspan="1" colspan="1">0.4077</td>
<td rowspan="1" colspan="1">0.050*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.18675 (11)</td>
<td rowspan="1" colspan="1">0.1131 (3)</td>
<td rowspan="1" colspan="1">0.40303 (9)</td>
<td rowspan="1" colspan="1">0.0397 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4A</td>
<td rowspan="1" colspan="1">0.1479</td>
<td rowspan="1" colspan="1">0.0344</td>
<td rowspan="1" colspan="1">0.3634</td>
<td rowspan="1" colspan="1">0.048*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4B</td>
<td rowspan="1" colspan="1">0.2196</td>
<td rowspan="1" colspan="1">−0.0059</td>
<td rowspan="1" colspan="1">0.4340</td>
<td rowspan="1" colspan="1">0.048*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.24503 (10)</td>
<td rowspan="1" colspan="1">0.2636 (3)</td>
<td rowspan="1" colspan="1">0.37920 (8)</td>
<td rowspan="1" colspan="1">0.0319 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.28907 (9)</td>
<td rowspan="1" colspan="1">0.4173 (3)</td>
<td rowspan="1" colspan="1">0.43809 (7)</td>
<td rowspan="1" colspan="1">0.0260 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.39559 (9)</td>
<td rowspan="1" colspan="1">0.6469 (3)</td>
<td rowspan="1" colspan="1">0.49858 (7)</td>
<td rowspan="1" colspan="1">0.0266 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.21999 (11)</td>
<td rowspan="1" colspan="1">0.1932 (3)</td>
<td rowspan="1" colspan="1">0.56307 (9)</td>
<td rowspan="1" colspan="1">0.0388 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.1720</td>
<td rowspan="1" colspan="1">0.1286</td>
<td rowspan="1" colspan="1">0.5713</td>
<td rowspan="1" colspan="1">0.058*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">0.2547</td>
<td rowspan="1" colspan="1">0.2727</td>
<td rowspan="1" colspan="1">0.6037</td>
<td rowspan="1" colspan="1">0.058*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8C</td>
<td rowspan="1" colspan="1">0.2514</td>
<td rowspan="1" colspan="1">0.0697</td>
<td rowspan="1" colspan="1">0.5518</td>
<td rowspan="1" colspan="1">0.058*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.14165 (11)</td>
<td rowspan="1" colspan="1">0.5539 (3)</td>
<td rowspan="1" colspan="1">0.52232 (10)</td>
<td rowspan="1" colspan="1">0.0427 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">0.0925</td>
<td rowspan="1" colspan="1">0.4881</td>
<td rowspan="1" colspan="1">0.5283</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9B</td>
<td rowspan="1" colspan="1">0.1253</td>
<td rowspan="1" colspan="1">0.6672</td>
<td rowspan="1" colspan="1">0.4859</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9C</td>
<td rowspan="1" colspan="1">0.1753</td>
<td rowspan="1" colspan="1">0.6282</td>
<td rowspan="1" colspan="1">0.5643</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.30657 (12)</td>
<td rowspan="1" colspan="1">0.1076 (3)</td>
<td rowspan="1" colspan="1">0.36271 (10)</td>
<td rowspan="1" colspan="1">0.0442 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.2769</td>
<td rowspan="1" colspan="1">−0.0070</td>
<td rowspan="1" colspan="1">0.3294</td>
<td rowspan="1" colspan="1">0.066*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">0.3410</td>
<td rowspan="1" colspan="1">0.0304</td>
<td rowspan="1" colspan="1">0.4039</td>
<td rowspan="1" colspan="1">0.066*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10C</td>
<td rowspan="1" colspan="1">0.3413</td>
<td rowspan="1" colspan="1">0.1996</td>
<td rowspan="1" colspan="1">0.3443</td>
<td rowspan="1" colspan="1">0.066*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.19849 (13)</td>
<td rowspan="1" colspan="1">0.4072 (4)</td>
<td rowspan="1" colspan="1">0.31745 (9)</td>
<td rowspan="1" colspan="1">0.0516 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.1707</td>
<td rowspan="1" colspan="1">0.3058</td>
<td rowspan="1" colspan="1">0.2795</td>
<td rowspan="1" colspan="1">0.077*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.2372</td>
<td rowspan="1" colspan="1">0.5057</td>
<td rowspan="1" colspan="1">0.3054</td>
<td rowspan="1" colspan="1">0.077*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11C</td>
<td rowspan="1" colspan="1">0.1577</td>
<td rowspan="1" colspan="1">0.5024</td>
<td rowspan="1" colspan="1">0.3278</td>
<td rowspan="1" colspan="1">0.077*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.36224 (8)</td>
<td rowspan="1" colspan="1">0.5279 (2)</td>
<td rowspan="1" colspan="1">0.44229 (6)</td>
<td rowspan="1" colspan="1">0.0271 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1N</td>
<td rowspan="1" colspan="1">0.3856 (11)</td>
<td rowspan="1" colspan="1">0.524 (3)</td>
<td rowspan="1" colspan="1">0.4110 (9)</td>
<td rowspan="1" colspan="1">0.033*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.46553 (9)</td>
<td rowspan="1" colspan="1">0.7605 (3)</td>
<td rowspan="1" colspan="1">0.51363 (7)</td>
<td rowspan="1" colspan="1">0.0337 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2N</td>
<td rowspan="1" colspan="1">0.4887 (12)</td>
<td rowspan="1" colspan="1">0.780 (3)</td>
<td rowspan="1" colspan="1">0.4812 (10)</td>
<td rowspan="1" colspan="1">0.040*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3N</td>
<td rowspan="1" colspan="1">0.4791 (12)</td>
<td rowspan="1" colspan="1">0.857 (3)</td>
<td rowspan="1" colspan="1">0.5486 (10)</td>
<td rowspan="1" colspan="1">0.040*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.33701 (2)</td>
<td rowspan="1" colspan="1">0.63371 (7)</td>
<td rowspan="1" colspan="1">0.55004 (2)</td>
<td rowspan="1" colspan="1">0.02882 (12)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.53091 (9)</td>
<td rowspan="1" colspan="1">0.7205 (3)</td>
<td rowspan="1" colspan="1">0.30278 (7)</td>
<td rowspan="1" colspan="1">0.0283 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.58549 (9)</td>
<td rowspan="1" colspan="1">0.8968 (3)</td>
<td rowspan="1" colspan="1">0.30559 (8)</td>
<td rowspan="1" colspan="1">0.0304 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H13</td>
<td rowspan="1" colspan="1">0.5992</td>
<td rowspan="1" colspan="1">1.0042</td>
<td rowspan="1" colspan="1">0.3416</td>
<td rowspan="1" colspan="1">0.037*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.61975 (9)</td>
<td rowspan="1" colspan="1">0.9144 (3)</td>
<td rowspan="1" colspan="1">0.25552 (8)</td>
<td rowspan="1" colspan="1">0.0313 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.60233 (9)</td>
<td rowspan="1" colspan="1">0.7633 (3)</td>
<td rowspan="1" colspan="1">0.20218 (8)</td>
<td rowspan="1" colspan="1">0.0327 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15</td>
<td rowspan="1" colspan="1">0.6256</td>
<td rowspan="1" colspan="1">0.7796</td>
<td rowspan="1" colspan="1">0.1676</td>
<td rowspan="1" colspan="1">0.039*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.54918 (9)</td>
<td rowspan="1" colspan="1">0.5872 (3)</td>
<td rowspan="1" colspan="1">0.20198 (8)</td>
<td rowspan="1" colspan="1">0.0306 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.51322 (9)</td>
<td rowspan="1" colspan="1">0.5616 (3)</td>
<td rowspan="1" colspan="1">0.25084 (7)</td>
<td rowspan="1" colspan="1">0.0294 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H17</td>
<td rowspan="1" colspan="1">0.4770</td>
<td rowspan="1" colspan="1">0.4375</td>
<td rowspan="1" colspan="1">0.2489</td>
<td rowspan="1" colspan="1">0.035*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.49110 (10)</td>
<td rowspan="1" colspan="1">0.7013 (3)</td>
<td rowspan="1" colspan="1">0.35667 (8)</td>
<td rowspan="1" colspan="1">0.0312 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.67709 (8)</td>
<td rowspan="1" colspan="1">1.1050 (3)</td>
<td rowspan="1" colspan="1">0.25924 (7)</td>
<td rowspan="1" colspan="1">0.0380 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.52907 (8)</td>
<td rowspan="1" colspan="1">0.4200 (3)</td>
<td rowspan="1" colspan="1">0.14618 (7)</td>
<td rowspan="1" colspan="1">0.0386 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.43858 (8)</td>
<td rowspan="1" colspan="1">0.5479 (2)</td>
<td rowspan="1" colspan="1">0.34910 (6)</td>
<td rowspan="1" colspan="1">0.0427 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.51480 (8)</td>
<td rowspan="1" colspan="1">0.8407 (2)</td>
<td rowspan="1" colspan="1">0.40440 (6)</td>
<td rowspan="1" colspan="1">0.0410 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.69300 (8)</td>
<td rowspan="1" colspan="1">1.1515 (2)</td>
<td rowspan="1" colspan="1">0.20855 (7)</td>
<td rowspan="1" colspan="1">0.0500 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.70535 (9)</td>
<td rowspan="1" colspan="1">1.2066 (3)</td>
<td rowspan="1" colspan="1">0.31259 (7)</td>
<td rowspan="1" colspan="1">0.0596 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O5</td>
<td rowspan="1" colspan="1">0.49224 (9)</td>
<td rowspan="1" colspan="1">0.2464 (3)</td>
<td rowspan="1" colspan="1">0.15173 (7)</td>
<td rowspan="1" colspan="1">0.0508 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O6</td>
<td rowspan="1" colspan="1">0.54967 (8)</td>
<td rowspan="1" colspan="1">0.4645 (3)</td>
<td rowspan="1" colspan="1">0.09754 (6)</td>
<td rowspan="1" colspan="1">0.0522 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e6026" sec-type="tablewrapadps"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e6038"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0251 (7)</td>
<td rowspan="1" colspan="1">0.0287 (8)</td>
<td rowspan="1" colspan="1">0.0255 (8)</td>
<td rowspan="1" colspan="1">−0.0025 (6)</td>
<td rowspan="1" colspan="1">0.0086 (6)</td>
<td rowspan="1" colspan="1">−0.0005 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0252 (8)</td>
<td rowspan="1" colspan="1">0.0364 (8)</td>
<td rowspan="1" colspan="1">0.0307 (8)</td>
<td rowspan="1" colspan="1">−0.0032 (6)</td>
<td rowspan="1" colspan="1">0.0130 (6)</td>
<td rowspan="1" colspan="1">0.0006 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0301 (9)</td>
<td rowspan="1" colspan="1">0.0543 (11)</td>
<td rowspan="1" colspan="1">0.0417 (10)</td>
<td rowspan="1" colspan="1">−0.0134 (8)</td>
<td rowspan="1" colspan="1">0.0129 (7)</td>
<td rowspan="1" colspan="1">−0.0047 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0385 (10)</td>
<td rowspan="1" colspan="1">0.0457 (10)</td>
<td rowspan="1" colspan="1">0.0350 (9)</td>
<td rowspan="1" colspan="1">−0.0158 (8)</td>
<td rowspan="1" colspan="1">0.0126 (7)</td>
<td rowspan="1" colspan="1">−0.0077 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0335 (8)</td>
<td rowspan="1" colspan="1">0.0374 (9)</td>
<td rowspan="1" colspan="1">0.0250 (8)</td>
<td rowspan="1" colspan="1">−0.0096 (7)</td>
<td rowspan="1" colspan="1">0.0103 (6)</td>
<td rowspan="1" colspan="1">−0.0039 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0252 (7)</td>
<td rowspan="1" colspan="1">0.0286 (8)</td>
<td rowspan="1" colspan="1">0.0248 (7)</td>
<td rowspan="1" colspan="1">−0.0034 (6)</td>
<td rowspan="1" colspan="1">0.0094 (6)</td>
<td rowspan="1" colspan="1">0.0005 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0290 (8)</td>
<td rowspan="1" colspan="1">0.0282 (8)</td>
<td rowspan="1" colspan="1">0.0250 (8)</td>
<td rowspan="1" colspan="1">−0.0031 (6)</td>
<td rowspan="1" colspan="1">0.0123 (6)</td>
<td rowspan="1" colspan="1">−0.0006 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0378 (9)</td>
<td rowspan="1" colspan="1">0.0441 (10)</td>
<td rowspan="1" colspan="1">0.0412 (10)</td>
<td rowspan="1" colspan="1">−0.0014 (8)</td>
<td rowspan="1" colspan="1">0.0222 (8)</td>
<td rowspan="1" colspan="1">0.0061 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0329 (9)</td>
<td rowspan="1" colspan="1">0.0470 (10)</td>
<td rowspan="1" colspan="1">0.0535 (11)</td>
<td rowspan="1" colspan="1">0.0034 (8)</td>
<td rowspan="1" colspan="1">0.0215 (8)</td>
<td rowspan="1" colspan="1">0.0005 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0509 (11)</td>
<td rowspan="1" colspan="1">0.0441 (10)</td>
<td rowspan="1" colspan="1">0.0437 (10)</td>
<td rowspan="1" colspan="1">−0.0122 (8)</td>
<td rowspan="1" colspan="1">0.0239 (9)</td>
<td rowspan="1" colspan="1">−0.0160 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.0576 (12)</td>
<td rowspan="1" colspan="1">0.0607 (13)</td>
<td rowspan="1" colspan="1">0.0276 (9)</td>
<td rowspan="1" colspan="1">−0.0091 (10)</td>
<td rowspan="1" colspan="1">0.0029 (8)</td>
<td rowspan="1" colspan="1">0.0015 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0296 (7)</td>
<td rowspan="1" colspan="1">0.0320 (7)</td>
<td rowspan="1" colspan="1">0.0236 (6)</td>
<td rowspan="1" colspan="1">−0.0064 (5)</td>
<td rowspan="1" colspan="1">0.0140 (5)</td>
<td rowspan="1" colspan="1">−0.0029 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.0352 (8)</td>
<td rowspan="1" colspan="1">0.0398 (8)</td>
<td rowspan="1" colspan="1">0.0304 (7)</td>
<td rowspan="1" colspan="1">−0.0140 (6)</td>
<td rowspan="1" colspan="1">0.0168 (6)</td>
<td rowspan="1" colspan="1">−0.0085 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0292 (2)</td>
<td rowspan="1" colspan="1">0.0350 (2)</td>
<td rowspan="1" colspan="1">0.0259 (2)</td>
<td rowspan="1" colspan="1">−0.00573 (16)</td>
<td rowspan="1" colspan="1">0.01407 (16)</td>
<td rowspan="1" colspan="1">−0.00554 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.0239 (7)</td>
<td rowspan="1" colspan="1">0.0392 (9)</td>
<td rowspan="1" colspan="1">0.0224 (7)</td>
<td rowspan="1" colspan="1">0.0017 (6)</td>
<td rowspan="1" colspan="1">0.0088 (6)</td>
<td rowspan="1" colspan="1">0.0036 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.0273 (8)</td>
<td rowspan="1" colspan="1">0.0396 (9)</td>
<td rowspan="1" colspan="1">0.0254 (8)</td>
<td rowspan="1" colspan="1">−0.0003 (7)</td>
<td rowspan="1" colspan="1">0.0103 (6)</td>
<td rowspan="1" colspan="1">0.0020 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.0230 (8)</td>
<td rowspan="1" colspan="1">0.0425 (9)</td>
<td rowspan="1" colspan="1">0.0291 (8)</td>
<td rowspan="1" colspan="1">0.0021 (7)</td>
<td rowspan="1" colspan="1">0.0099 (6)</td>
<td rowspan="1" colspan="1">0.0083 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0236 (8)</td>
<td rowspan="1" colspan="1">0.0520 (10)</td>
<td rowspan="1" colspan="1">0.0243 (8)</td>
<td rowspan="1" colspan="1">0.0090 (7)</td>
<td rowspan="1" colspan="1">0.0106 (6)</td>
<td rowspan="1" colspan="1">0.0086 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.0230 (7)</td>
<td rowspan="1" colspan="1">0.0451 (9)</td>
<td rowspan="1" colspan="1">0.0220 (7)</td>
<td rowspan="1" colspan="1">0.0085 (7)</td>
<td rowspan="1" colspan="1">0.0056 (6)</td>
<td rowspan="1" colspan="1">0.0002 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.0221 (7)</td>
<td rowspan="1" colspan="1">0.0390 (8)</td>
<td rowspan="1" colspan="1">0.0257 (8)</td>
<td rowspan="1" colspan="1">0.0006 (6)</td>
<td rowspan="1" colspan="1">0.0063 (6)</td>
<td rowspan="1" colspan="1">0.0015 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.0300 (8)</td>
<td rowspan="1" colspan="1">0.0392 (9)</td>
<td rowspan="1" colspan="1">0.0271 (8)</td>
<td rowspan="1" colspan="1">−0.0042 (7)</td>
<td rowspan="1" colspan="1">0.0133 (6)</td>
<td rowspan="1" colspan="1">−0.0005 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.0305 (7)</td>
<td rowspan="1" colspan="1">0.0491 (9)</td>
<td rowspan="1" colspan="1">0.0396 (8)</td>
<td rowspan="1" colspan="1">−0.0014 (6)</td>
<td rowspan="1" colspan="1">0.0184 (6)</td>
<td rowspan="1" colspan="1">0.0090 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.0273 (7)</td>
<td rowspan="1" colspan="1">0.0557 (10)</td>
<td rowspan="1" colspan="1">0.0313 (8)</td>
<td rowspan="1" colspan="1">0.0099 (7)</td>
<td rowspan="1" colspan="1">0.0081 (6)</td>
<td rowspan="1" colspan="1">−0.0056 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0462 (7)</td>
<td rowspan="1" colspan="1">0.0556 (8)</td>
<td rowspan="1" colspan="1">0.0347 (7)</td>
<td rowspan="1" colspan="1">−0.0218 (6)</td>
<td rowspan="1" colspan="1">0.0244 (6)</td>
<td rowspan="1" colspan="1">−0.0106 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0512 (8)</td>
<td rowspan="1" colspan="1">0.0453 (7)</td>
<td rowspan="1" colspan="1">0.0363 (7)</td>
<td rowspan="1" colspan="1">−0.0158 (6)</td>
<td rowspan="1" colspan="1">0.0275 (6)</td>
<td rowspan="1" colspan="1">−0.0114 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.0466 (8)</td>
<td rowspan="1" colspan="1">0.0666 (9)</td>
<td rowspan="1" colspan="1">0.0461 (8)</td>
<td rowspan="1" colspan="1">−0.0058 (6)</td>
<td rowspan="1" colspan="1">0.0280 (6)</td>
<td rowspan="1" colspan="1">0.0147 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.0662 (10)</td>
<td rowspan="1" colspan="1">0.0704 (10)</td>
<td rowspan="1" colspan="1">0.0507 (9)</td>
<td rowspan="1" colspan="1">−0.0328 (8)</td>
<td rowspan="1" colspan="1">0.0311 (7)</td>
<td rowspan="1" colspan="1">−0.0119 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">O5</td>
<td rowspan="1" colspan="1">0.0504 (8)</td>
<td rowspan="1" colspan="1">0.0563 (9)</td>
<td rowspan="1" colspan="1">0.0448 (8)</td>
<td rowspan="1" colspan="1">−0.0036 (7)</td>
<td rowspan="1" colspan="1">0.0149 (6)</td>
<td rowspan="1" colspan="1">−0.0156 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">O6</td>
<td rowspan="1" colspan="1">0.0452 (8)</td>
<td rowspan="1" colspan="1">0.0852 (10)</td>
<td rowspan="1" colspan="1">0.0316 (7)</td>
<td rowspan="1" colspan="1">0.0108 (7)</td>
<td rowspan="1" colspan="1">0.0199 (6)</td>
<td rowspan="1" colspan="1">−0.0082 (7)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e6583" sec-type="tablewrapgeomlong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e6593"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.340 (2)</td>
<td rowspan="1" colspan="1">C10—H10B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.506 (2)</td>
<td rowspan="1" colspan="1">C10—H10C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—S1</td>
<td rowspan="1" colspan="1">1.7540 (15)</td>
<td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8</td>
<td rowspan="1" colspan="1">1.532 (2)</td>
<td rowspan="1" colspan="1">C11—H11B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9</td>
<td rowspan="1" colspan="1">1.535 (2)</td>
<td rowspan="1" colspan="1">C11—H11C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.538 (2)</td>
<td rowspan="1" colspan="1">N1—H1N</td>
<td rowspan="1" colspan="1">0.885 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.521 (3)</td>
<td rowspan="1" colspan="1">N2—H2N</td>
<td rowspan="1" colspan="1">0.91 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3A</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">N2—H3N</td>
<td rowspan="1" colspan="1">0.90 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3B</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.385 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.546 (2)</td>
<td rowspan="1" colspan="1">C12—C17</td>
<td rowspan="1" colspan="1">1.388 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4A</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C12—C18</td>
<td rowspan="1" colspan="1">1.521 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4B</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.380 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.512 (2)</td>
<td rowspan="1" colspan="1">C13—H13</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11</td>
<td rowspan="1" colspan="1">1.528 (2)</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.380 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10</td>
<td rowspan="1" colspan="1">1.529 (2)</td>
<td rowspan="1" colspan="1">C14—N3</td>
<td rowspan="1" colspan="1">1.476 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1</td>
<td rowspan="1" colspan="1">1.3981 (19)</td>
<td rowspan="1" colspan="1">C15—C16</td>
<td rowspan="1" colspan="1">1.380 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2</td>
<td rowspan="1" colspan="1">1.322 (2)</td>
<td rowspan="1" colspan="1">C15—H15</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1</td>
<td rowspan="1" colspan="1">1.3267 (19)</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.381 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—S1</td>
<td rowspan="1" colspan="1">1.7211 (15)</td>
<td rowspan="1" colspan="1">C16—N4</td>
<td rowspan="1" colspan="1">1.477 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C17—H17</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C18—O1</td>
<td rowspan="1" colspan="1">1.2475 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C18—O2</td>
<td rowspan="1" colspan="1">1.2506 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N3—O4</td>
<td rowspan="1" colspan="1">1.2178 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N3—O3</td>
<td rowspan="1" colspan="1">1.2218 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N4—O6</td>
<td rowspan="1" colspan="1">1.2231 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N4—O5</td>
<td rowspan="1" colspan="1">1.224 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2</td>
<td rowspan="1" colspan="1">127.39 (14)</td>
<td rowspan="1" colspan="1">C5—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—S1</td>
<td rowspan="1" colspan="1">110.64 (11)</td>
<td rowspan="1" colspan="1">H10A—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—S1</td>
<td rowspan="1" colspan="1">121.88 (11)</td>
<td rowspan="1" colspan="1">C5—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C8</td>
<td rowspan="1" colspan="1">109.11 (13)</td>
<td rowspan="1" colspan="1">H10A—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C9</td>
<td rowspan="1" colspan="1">111.17 (13)</td>
<td rowspan="1" colspan="1">H10B—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C9</td>
<td rowspan="1" colspan="1">108.85 (13)</td>
<td rowspan="1" colspan="1">C5—C11—H11A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3</td>
<td rowspan="1" colspan="1">106.95 (12)</td>
<td rowspan="1" colspan="1">C5—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3</td>
<td rowspan="1" colspan="1">111.61 (14)</td>
<td rowspan="1" colspan="1">H11A—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3</td>
<td rowspan="1" colspan="1">109.15 (14)</td>
<td rowspan="1" colspan="1">C5—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—C2</td>
<td rowspan="1" colspan="1">113.90 (14)</td>
<td rowspan="1" colspan="1">H11A—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3A</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">H11B—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3A</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C7—N1—C6</td>
<td rowspan="1" colspan="1">114.09 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3B</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C7—N1—H1N</td>
<td rowspan="1" colspan="1">120.8 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3B</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C6—N1—H1N</td>
<td rowspan="1" colspan="1">125.1 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A—C3—H3B</td>
<td rowspan="1" colspan="1">107.7</td>
<td rowspan="1" colspan="1">C7—N2—H2N</td>
<td rowspan="1" colspan="1">119.0 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5</td>
<td rowspan="1" colspan="1">113.96 (15)</td>
<td rowspan="1" colspan="1">C7—N2—H3N</td>
<td rowspan="1" colspan="1">118.5 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4A</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">H2N—N2—H3N</td>
<td rowspan="1" colspan="1">118.8 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—H4A</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C7—S1—C1</td>
<td rowspan="1" colspan="1">90.40 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4B</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C13—C12—C17</td>
<td rowspan="1" colspan="1">119.67 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—H4B</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C13—C12—C18</td>
<td rowspan="1" colspan="1">119.95 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A—C4—H4B</td>
<td rowspan="1" colspan="1">107.7</td>
<td rowspan="1" colspan="1">C17—C12—C18</td>
<td rowspan="1" colspan="1">120.38 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C11</td>
<td rowspan="1" colspan="1">110.26 (14)</td>
<td rowspan="1" colspan="1">C14—C13—C12</td>
<td rowspan="1" colspan="1">119.18 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C10</td>
<td rowspan="1" colspan="1">110.14 (13)</td>
<td rowspan="1" colspan="1">C14—C13—H13</td>
<td rowspan="1" colspan="1">120.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C10</td>
<td rowspan="1" colspan="1">109.86 (15)</td>
<td rowspan="1" colspan="1">C12—C13—H13</td>
<td rowspan="1" colspan="1">120.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4</td>
<td rowspan="1" colspan="1">105.88 (12)</td>
<td rowspan="1" colspan="1">C13—C14—C15</td>
<td rowspan="1" colspan="1">122.97 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C4</td>
<td rowspan="1" colspan="1">112.06 (15)</td>
<td rowspan="1" colspan="1">C13—C14—N3</td>
<td rowspan="1" colspan="1">118.18 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C4</td>
<td rowspan="1" colspan="1">108.56 (14)</td>
<td rowspan="1" colspan="1">C15—C14—N3</td>
<td rowspan="1" colspan="1">118.85 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1</td>
<td rowspan="1" colspan="1">113.12 (13)</td>
<td rowspan="1" colspan="1">C16—C15—C14</td>
<td rowspan="1" colspan="1">116.12 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—C5</td>
<td rowspan="1" colspan="1">125.55 (13)</td>
<td rowspan="1" colspan="1">C16—C15—H15</td>
<td rowspan="1" colspan="1">121.9</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C6—C5</td>
<td rowspan="1" colspan="1">121.31 (12)</td>
<td rowspan="1" colspan="1">C14—C15—H15</td>
<td rowspan="1" colspan="1">121.9</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1</td>
<td rowspan="1" colspan="1">124.23 (14)</td>
<td rowspan="1" colspan="1">C15—C16—C17</td>
<td rowspan="1" colspan="1">123.23 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1</td>
<td rowspan="1" colspan="1">124.04 (12)</td>
<td rowspan="1" colspan="1">C15—C16—N4</td>
<td rowspan="1" colspan="1">118.16 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C7—S1</td>
<td rowspan="1" colspan="1">111.72 (11)</td>
<td rowspan="1" colspan="1">C17—C16—N4</td>
<td rowspan="1" colspan="1">118.60 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C17—C12</td>
<td rowspan="1" colspan="1">118.79 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C17—H17</td>
<td rowspan="1" colspan="1">120.6</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C12—C17—H17</td>
<td rowspan="1" colspan="1">120.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O1—C18—O2</td>
<td rowspan="1" colspan="1">126.60 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O1—C18—C12</td>
<td rowspan="1" colspan="1">116.98 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">H8B—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O2—C18—C12</td>
<td rowspan="1" colspan="1">116.42 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O4—N3—O3</td>
<td rowspan="1" colspan="1">124.09 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O4—N3—C14</td>
<td rowspan="1" colspan="1">117.95 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O3—N3—C14</td>
<td rowspan="1" colspan="1">117.96 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O6—N4—O5</td>
<td rowspan="1" colspan="1">124.50 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O6—N4—C16</td>
<td rowspan="1" colspan="1">118.07 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9B—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O5—N4—C16</td>
<td rowspan="1" colspan="1">117.43 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C8</td>
<td rowspan="1" colspan="1">109.98 (18)</td>
<td rowspan="1" colspan="1">N1—C7—S1—C1</td>
<td rowspan="1" colspan="1">0.11 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C8</td>
<td rowspan="1" colspan="1">−66.27 (17)</td>
<td rowspan="1" colspan="1">C6—C1—S1—C7</td>
<td rowspan="1" colspan="1">0.86 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C9</td>
<td rowspan="1" colspan="1">−129.96 (17)</td>
<td rowspan="1" colspan="1">C2—C1—S1—C7</td>
<td rowspan="1" colspan="1">177.68 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C9</td>
<td rowspan="1" colspan="1">53.79 (18)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C14</td>
<td rowspan="1" colspan="1">1.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td>
<td rowspan="1" colspan="1">−10.9 (2)</td>
<td rowspan="1" colspan="1">C18—C12—C13—C14</td>
<td rowspan="1" colspan="1">−178.67 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C3</td>
<td rowspan="1" colspan="1">172.86 (12)</td>
<td rowspan="1" colspan="1">C12—C13—C14—C15</td>
<td rowspan="1" colspan="1">−0.1 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td>
<td rowspan="1" colspan="1">40.0 (2)</td>
<td rowspan="1" colspan="1">C12—C13—C14—N3</td>
<td rowspan="1" colspan="1">179.39 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3—C4</td>
<td rowspan="1" colspan="1">−79.31 (18)</td>
<td rowspan="1" colspan="1">C13—C14—C15—C16</td>
<td rowspan="1" colspan="1">−1.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3—C4</td>
<td rowspan="1" colspan="1">160.33 (15)</td>
<td rowspan="1" colspan="1">N3—C14—C15—C16</td>
<td rowspan="1" colspan="1">179.18 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td>
<td rowspan="1" colspan="1">−62.4 (2)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C17</td>
<td rowspan="1" colspan="1">1.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td>
<td rowspan="1" colspan="1">46.04 (19)</td>
<td rowspan="1" colspan="1">C14—C15—C16—N4</td>
<td rowspan="1" colspan="1">−179.58 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5—C11</td>
<td rowspan="1" colspan="1">−74.21 (19)</td>
<td rowspan="1" colspan="1">C15—C16—C17—C12</td>
<td rowspan="1" colspan="1">0.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5—C10</td>
<td rowspan="1" colspan="1">164.27 (15)</td>
<td rowspan="1" colspan="1">N4—C16—C17—C12</td>
<td rowspan="1" colspan="1">−178.97 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—N1</td>
<td rowspan="1" colspan="1">−178.20 (14)</td>
<td rowspan="1" colspan="1">C13—C12—C17—C16</td>
<td rowspan="1" colspan="1">−1.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C6—N1</td>
<td rowspan="1" colspan="1">−1.60 (17)</td>
<td rowspan="1" colspan="1">C18—C12—C17—C16</td>
<td rowspan="1" colspan="1">178.65 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td>
<td rowspan="1" colspan="1">0.1 (3)</td>
<td rowspan="1" colspan="1">C13—C12—C18—O1</td>
<td rowspan="1" colspan="1">175.54 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C6—C5</td>
<td rowspan="1" colspan="1">176.71 (13)</td>
<td rowspan="1" colspan="1">C17—C12—C18—O1</td>
<td rowspan="1" colspan="1">−4.8 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C6—C1</td>
<td rowspan="1" colspan="1">104.46 (19)</td>
<td rowspan="1" colspan="1">C13—C12—C18—O2</td>
<td rowspan="1" colspan="1">−4.8 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C6—C1</td>
<td rowspan="1" colspan="1">−134.13 (17)</td>
<td rowspan="1" colspan="1">C17—C12—C18—O2</td>
<td rowspan="1" colspan="1">174.86 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td>
<td rowspan="1" colspan="1">−16.9 (2)</td>
<td rowspan="1" colspan="1">C13—C14—N3—O4</td>
<td rowspan="1" colspan="1">15.8 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C6—N1</td>
<td rowspan="1" colspan="1">−77.36 (19)</td>
<td rowspan="1" colspan="1">C15—C14—N3—O4</td>
<td rowspan="1" colspan="1">−164.70 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C6—N1</td>
<td rowspan="1" colspan="1">44.0 (2)</td>
<td rowspan="1" colspan="1">C13—C14—N3—O3</td>
<td rowspan="1" colspan="1">−164.01 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6—N1</td>
<td rowspan="1" colspan="1">161.23 (14)</td>
<td rowspan="1" colspan="1">C15—C14—N3—O3</td>
<td rowspan="1" colspan="1">15.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1—C6</td>
<td rowspan="1" colspan="1">178.54 (15)</td>
<td rowspan="1" colspan="1">C15—C16—N4—O6</td>
<td rowspan="1" colspan="1">−11.4 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C7—N1—C6</td>
<td rowspan="1" colspan="1">−1.05 (17)</td>
<td rowspan="1" colspan="1">C17—C16—N4—O6</td>
<td rowspan="1" colspan="1">167.84 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1—C7</td>
<td rowspan="1" colspan="1">1.76 (19)</td>
<td rowspan="1" colspan="1">C15—C16—N4—O5</td>
<td rowspan="1" colspan="1">169.17 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—N1—C7</td>
<td rowspan="1" colspan="1">−176.63 (14)</td>
<td rowspan="1" colspan="1">C17—C16—N4—O5</td>
<td rowspan="1" colspan="1">−11.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1—C1</td>
<td rowspan="1" colspan="1">−179.48 (15)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e7567" sec-type="tablewraphbondslong"><label>2-Amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium
3,5-dinitrobenzoate (III) </label>
<title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e7576"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H</td>
<td rowspan="1" colspan="1">H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1<italic>N</italic>
···O1</td>
<td rowspan="1" colspan="1">0.885 (19)</td>
<td rowspan="1" colspan="1">1.838 (19)</td>
<td rowspan="1" colspan="1">2.7187 (17)</td>
<td rowspan="1" colspan="1">173.4 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3<italic>N</italic>
···O2<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.90 (2)</td>
<td rowspan="1" colspan="1">2.01 (2)</td>
<td rowspan="1" colspan="1">2.8509 (19)</td>
<td rowspan="1" colspan="1">156.3 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2<italic>N</italic>
···O2</td>
<td rowspan="1" colspan="1">0.91 (2)</td>
<td rowspan="1" colspan="1">1.86 (2)</td>
<td rowspan="1" colspan="1">2.7551 (18)</td>
<td rowspan="1" colspan="1">168.3 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8<italic>A</italic>
···O6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.98</td>
<td rowspan="1" colspan="1">2.43</td>
<td rowspan="1" colspan="1">3.397 (2)</td>
<td rowspan="1" colspan="1">170</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) −<italic>x</italic>
+1, −<italic>y</italic>
+2, −<italic>z</italic>
+1; (ii) <italic>x</italic>
−1/2, −<italic>y</italic>
+1/2, <italic>z</italic>
+1/2.</p>
</sec>
<sec id="d1e7717" sec-type="tablewrapcrystaldatalong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e7726"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">2C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2</sup>
<sup>−</sup>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 576</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 536.74</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.224 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 9.0259 (6) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 4569 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 14.7314 (11) Å</td>
<td rowspan="1" colspan="1">θ = 2.3–23.7°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 11.1993 (8) Å</td>
<td rowspan="1" colspan="1">µ = 0.22 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 101.943 (6)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 173 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 1456.87 (18) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">Prism, orange</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 2</td>
<td rowspan="1" colspan="1">0.15 × 0.08 × 0.02 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e7855" sec-type="tablewrapdatacollectionlong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e7864"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Rigaku XtaLAB P200 HPC diffractometer</td>
<td rowspan="1" colspan="1">6424 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: rotating anode, Rigaku FR-X</td>
<td rowspan="1" colspan="1">3792 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Rigaku Osmic Confocal Optical System monochromator</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.080</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 29.1°, θ<sub>min</sub>
 = 1.9°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −12→11</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.333, <italic>T</italic>
<sub>max</sub>
 = 1.000</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −18→20</td>
</tr>
<tr><td rowspan="1" colspan="1">19263 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −14→12</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e7966" sec-type="tablewraprefinementdatalong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e7975"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Hydrogen site location: mixed</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.062</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0488<italic>P</italic>
)<sup>2</sup>
] where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.128</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 < 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.00</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.27 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">6424 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.26 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">350 parameters</td>
<td rowspan="1" colspan="1">Absolute structure: Flack <italic>x</italic> determined using 1279 quotients
[(<italic>I</italic>
<sup>+</sup>
)-(<italic>I</italic>
<sup>-</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>-</sup>)]
(Parsons <italic>et al.</italic>
, 2013).</td>
</tr>
<tr><td rowspan="1" colspan="1">1 restraint</td>
<td rowspan="1" colspan="1">Absolute structure parameter: 0.46 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e8150" sec-type="specialdetails"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e8160"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e8169" sec-type="tablewrapcoords"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e8181"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1">Occ. (<1)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">1.2869 (6)</td>
<td rowspan="1" colspan="1">0.3952 (4)</td>
<td rowspan="1" colspan="1">0.6937 (4)</td>
<td rowspan="1" colspan="1">0.0339 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">1.3939 (6)</td>
<td rowspan="1" colspan="1">0.4406 (4)</td>
<td rowspan="1" colspan="1">0.7989 (5)</td>
<td rowspan="1" colspan="1">0.0467 (15)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3A</td>
<td rowspan="1" colspan="1">1.2984 (8)</td>
<td rowspan="1" colspan="1">0.5068 (7)</td>
<td rowspan="1" colspan="1">0.8546 (8)</td>
<td rowspan="1" colspan="1">0.052 (3)*</td>
<td rowspan="1" colspan="1">0.78 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A1</td>
<td rowspan="1" colspan="1">1.2720</td>
<td rowspan="1" colspan="1">0.5596</td>
<td rowspan="1" colspan="1">0.7996</td>
<td rowspan="1" colspan="1">0.062*</td>
<td rowspan="1" colspan="1">0.78 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A2</td>
<td rowspan="1" colspan="1">1.3578</td>
<td rowspan="1" colspan="1">0.5293</td>
<td rowspan="1" colspan="1">0.9334</td>
<td rowspan="1" colspan="1">0.062*</td>
<td rowspan="1" colspan="1">0.78 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A</td>
<td rowspan="1" colspan="1">1.1520 (10)</td>
<td rowspan="1" colspan="1">0.4615 (8)</td>
<td rowspan="1" colspan="1">0.8755 (8)</td>
<td rowspan="1" colspan="1">0.047 (2)*</td>
<td rowspan="1" colspan="1">0.78 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A1</td>
<td rowspan="1" colspan="1">1.1017</td>
<td rowspan="1" colspan="1">0.5022</td>
<td rowspan="1" colspan="1">0.9252</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1">0.78 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A2</td>
<td rowspan="1" colspan="1">1.1780</td>
<td rowspan="1" colspan="1">0.4044</td>
<td rowspan="1" colspan="1">0.9216</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1">0.78 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B</td>
<td rowspan="1" colspan="1">1.284 (3)</td>
<td rowspan="1" colspan="1">0.456 (3)</td>
<td rowspan="1" colspan="1">0.899 (3)</td>
<td rowspan="1" colspan="1">0.063 (12)*</td>
<td rowspan="1" colspan="1">0.22 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B1</td>
<td rowspan="1" colspan="1">1.2677</td>
<td rowspan="1" colspan="1">0.3968</td>
<td rowspan="1" colspan="1">0.9362</td>
<td rowspan="1" colspan="1">0.075*</td>
<td rowspan="1" colspan="1">0.22 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B2</td>
<td rowspan="1" colspan="1">1.3377</td>
<td rowspan="1" colspan="1">0.4959</td>
<td rowspan="1" colspan="1">0.9657</td>
<td rowspan="1" colspan="1">0.075*</td>
<td rowspan="1" colspan="1">0.22 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B</td>
<td rowspan="1" colspan="1">1.130 (3)</td>
<td rowspan="1" colspan="1">0.498 (2)</td>
<td rowspan="1" colspan="1">0.846 (3)</td>
<td rowspan="1" colspan="1">0.033 (8)*</td>
<td rowspan="1" colspan="1">0.22 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B1</td>
<td rowspan="1" colspan="1">1.0735</td>
<td rowspan="1" colspan="1">0.5078</td>
<td rowspan="1" colspan="1">0.9121</td>
<td rowspan="1" colspan="1">0.039*</td>
<td rowspan="1" colspan="1">0.22 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B2</td>
<td rowspan="1" colspan="1">1.1445</td>
<td rowspan="1" colspan="1">0.5582</td>
<td rowspan="1" colspan="1">0.8102</td>
<td rowspan="1" colspan="1">0.039*</td>
<td rowspan="1" colspan="1">0.22 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">1.0394 (6)</td>
<td rowspan="1" colspan="1">0.4401 (4)</td>
<td rowspan="1" colspan="1">0.7513 (4)</td>
<td rowspan="1" colspan="1">0.0372 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">1.1349 (6)</td>
<td rowspan="1" colspan="1">0.3955 (3)</td>
<td rowspan="1" colspan="1">0.6728 (4)</td>
<td rowspan="1" colspan="1">0.0312 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">1.1687 (6)</td>
<td rowspan="1" colspan="1">0.3114 (3)</td>
<td rowspan="1" colspan="1">0.5087 (4)</td>
<td rowspan="1" colspan="1">0.0320 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">1.4824 (7)</td>
<td rowspan="1" colspan="1">0.3683 (4)</td>
<td rowspan="1" colspan="1">0.8815 (6)</td>
<td rowspan="1" colspan="1">0.067 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">1.5474</td>
<td rowspan="1" colspan="1">0.3975</td>
<td rowspan="1" colspan="1">0.9519</td>
<td rowspan="1" colspan="1">0.101*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">1.5451</td>
<td rowspan="1" colspan="1">0.3337</td>
<td rowspan="1" colspan="1">0.8359</td>
<td rowspan="1" colspan="1">0.101*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8C</td>
<td rowspan="1" colspan="1">1.4115</td>
<td rowspan="1" colspan="1">0.3272</td>
<td rowspan="1" colspan="1">0.9098</td>
<td rowspan="1" colspan="1">0.101*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">1.5096 (8)</td>
<td rowspan="1" colspan="1">0.4998 (5)</td>
<td rowspan="1" colspan="1">0.7490 (6)</td>
<td rowspan="1" colspan="1">0.076 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">1.5751</td>
<td rowspan="1" colspan="1">0.5316</td>
<td rowspan="1" colspan="1">0.8168</td>
<td rowspan="1" colspan="1">0.114*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9B</td>
<td rowspan="1" colspan="1">1.4553</td>
<td rowspan="1" colspan="1">0.5443</td>
<td rowspan="1" colspan="1">0.6909</td>
<td rowspan="1" colspan="1">0.114*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9C</td>
<td rowspan="1" colspan="1">1.5715</td>
<td rowspan="1" colspan="1">0.4610</td>
<td rowspan="1" colspan="1">0.7077</td>
<td rowspan="1" colspan="1">0.114*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.9232 (6)</td>
<td rowspan="1" colspan="1">0.3732 (4)</td>
<td rowspan="1" colspan="1">0.7813 (5)</td>
<td rowspan="1" colspan="1">0.0506 (16)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.8700</td>
<td rowspan="1" colspan="1">0.4009</td>
<td rowspan="1" colspan="1">0.8400</td>
<td rowspan="1" colspan="1">0.076*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">0.9750</td>
<td rowspan="1" colspan="1">0.3180</td>
<td rowspan="1" colspan="1">0.8167</td>
<td rowspan="1" colspan="1">0.076*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10C</td>
<td rowspan="1" colspan="1">0.8501</td>
<td rowspan="1" colspan="1">0.3578</td>
<td rowspan="1" colspan="1">0.7065</td>
<td rowspan="1" colspan="1">0.076*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.9553 (8)</td>
<td rowspan="1" colspan="1">0.5223 (5)</td>
<td rowspan="1" colspan="1">0.6843 (6)</td>
<td rowspan="1" colspan="1">0.070 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.8941</td>
<td rowspan="1" colspan="1">0.5512</td>
<td rowspan="1" colspan="1">0.7364</td>
<td rowspan="1" colspan="1">0.105*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.8892</td>
<td rowspan="1" colspan="1">0.5020</td>
<td rowspan="1" colspan="1">0.6083</td>
<td rowspan="1" colspan="1">0.105*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11C</td>
<td rowspan="1" colspan="1">1.0291</td>
<td rowspan="1" colspan="1">0.5661</td>
<td rowspan="1" colspan="1">0.6656</td>
<td rowspan="1" colspan="1">0.105*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">1.0694 (5)</td>
<td rowspan="1" colspan="1">0.3476 (3)</td>
<td rowspan="1" colspan="1">0.5669 (4)</td>
<td rowspan="1" colspan="1">0.0298 (11)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1N</td>
<td rowspan="1" colspan="1">0.976 (6)</td>
<td rowspan="1" colspan="1">0.334 (4)</td>
<td rowspan="1" colspan="1">0.544 (4)</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">1.1307 (6)</td>
<td rowspan="1" colspan="1">0.2614 (4)</td>
<td rowspan="1" colspan="1">0.4096 (4)</td>
<td rowspan="1" colspan="1">0.0452 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2N</td>
<td rowspan="1" colspan="1">1.029 (7)</td>
<td rowspan="1" colspan="1">0.263 (4)</td>
<td rowspan="1" colspan="1">0.369 (5)</td>
<td rowspan="1" colspan="1">0.054*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3N</td>
<td rowspan="1" colspan="1">1.202 (6)</td>
<td rowspan="1" colspan="1">0.248 (4)</td>
<td rowspan="1" colspan="1">0.365 (5)</td>
<td rowspan="1" colspan="1">0.054*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">1.35226 (14)</td>
<td rowspan="1" colspan="1">0.33370 (9)</td>
<td rowspan="1" colspan="1">0.58194 (12)</td>
<td rowspan="1" colspan="1">0.0396 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">−0.1633 (6)</td>
<td rowspan="1" colspan="1">0.1107 (4)</td>
<td rowspan="1" colspan="1">−0.1894 (4)</td>
<td rowspan="1" colspan="1">0.0340 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">−0.2578 (6)</td>
<td rowspan="1" colspan="1">0.0698 (4)</td>
<td rowspan="1" colspan="1">−0.3022 (5)</td>
<td rowspan="1" colspan="1">0.0408 (14)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">−0.1503 (6)</td>
<td rowspan="1" colspan="1">0.0460 (4)</td>
<td rowspan="1" colspan="1">−0.3869 (5)</td>
<td rowspan="1" colspan="1">0.0501 (16)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14A</td>
<td rowspan="1" colspan="1">−0.2031</td>
<td rowspan="1" colspan="1">0.0048</td>
<td rowspan="1" colspan="1">−0.4519</td>
<td rowspan="1" colspan="1">0.060*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14B</td>
<td rowspan="1" colspan="1">−0.1244</td>
<td rowspan="1" colspan="1">0.1022</td>
<td rowspan="1" colspan="1">−0.4265</td>
<td rowspan="1" colspan="1">0.060*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">−0.0046 (6)</td>
<td rowspan="1" colspan="1">0.0005 (4)</td>
<td rowspan="1" colspan="1">−0.3204 (5)</td>
<td rowspan="1" colspan="1">0.0493 (15)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15A</td>
<td rowspan="1" colspan="1">0.0557</td>
<td rowspan="1" colspan="1">−0.0170</td>
<td rowspan="1" colspan="1">−0.3813</td>
<td rowspan="1" colspan="1">0.059*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15B</td>
<td rowspan="1" colspan="1">−0.0312</td>
<td rowspan="1" colspan="1">−0.0558</td>
<td rowspan="1" colspan="1">−0.2816</td>
<td rowspan="1" colspan="1">0.059*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.0948 (6)</td>
<td rowspan="1" colspan="1">0.0599 (4)</td>
<td rowspan="1" colspan="1">−0.2219 (4)</td>
<td rowspan="1" colspan="1">0.0353 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">−0.0114 (5)</td>
<td rowspan="1" colspan="1">0.1088 (3)</td>
<td rowspan="1" colspan="1">−0.1552 (4)</td>
<td rowspan="1" colspan="1">0.0286 (12)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">−0.0619 (6)</td>
<td rowspan="1" colspan="1">0.1945 (4)</td>
<td rowspan="1" colspan="1">0.0014 (5)</td>
<td rowspan="1" colspan="1">0.0338 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">−0.3410 (7)</td>
<td rowspan="1" colspan="1">−0.0144 (4)</td>
<td rowspan="1" colspan="1">−0.2709 (6)</td>
<td rowspan="1" colspan="1">0.0662 (19)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19A</td>
<td rowspan="1" colspan="1">−0.4097</td>
<td rowspan="1" colspan="1">−0.0366</td>
<td rowspan="1" colspan="1">−0.3446</td>
<td rowspan="1" colspan="1">0.099*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19B</td>
<td rowspan="1" colspan="1">−0.3995</td>
<td rowspan="1" colspan="1">0.0012</td>
<td rowspan="1" colspan="1">−0.2092</td>
<td rowspan="1" colspan="1">0.099*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19C</td>
<td rowspan="1" colspan="1">−0.2672</td>
<td rowspan="1" colspan="1">−0.0618</td>
<td rowspan="1" colspan="1">−0.2389</td>
<td rowspan="1" colspan="1">0.099*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">−0.3760 (6)</td>
<td rowspan="1" colspan="1">0.1378 (4)</td>
<td rowspan="1" colspan="1">−0.3673 (6)</td>
<td rowspan="1" colspan="1">0.0556 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20A</td>
<td rowspan="1" colspan="1">−0.4356</td>
<td rowspan="1" colspan="1">0.1098</td>
<td rowspan="1" colspan="1">−0.4412</td>
<td rowspan="1" colspan="1">0.083*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20B</td>
<td rowspan="1" colspan="1">−0.3246</td>
<td rowspan="1" colspan="1">0.1919</td>
<td rowspan="1" colspan="1">−0.3896</td>
<td rowspan="1" colspan="1">0.083*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20C</td>
<td rowspan="1" colspan="1">−0.4432</td>
<td rowspan="1" colspan="1">0.1552</td>
<td rowspan="1" colspan="1">−0.3127</td>
<td rowspan="1" colspan="1">0.083*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.2029 (6)</td>
<td rowspan="1" colspan="1">−0.0017 (4)</td>
<td rowspan="1" colspan="1">−0.1334 (5)</td>
<td rowspan="1" colspan="1">0.0498 (15)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21A</td>
<td rowspan="1" colspan="1">0.2615</td>
<td rowspan="1" colspan="1">−0.0391</td>
<td rowspan="1" colspan="1">−0.1793</td>
<td rowspan="1" colspan="1">0.075*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21B</td>
<td rowspan="1" colspan="1">0.1441</td>
<td rowspan="1" colspan="1">−0.0412</td>
<td rowspan="1" colspan="1">−0.0901</td>
<td rowspan="1" colspan="1">0.075*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21C</td>
<td rowspan="1" colspan="1">0.2720</td>
<td rowspan="1" colspan="1">0.0357</td>
<td rowspan="1" colspan="1">−0.0743</td>
<td rowspan="1" colspan="1">0.075*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.1855 (7)</td>
<td rowspan="1" colspan="1">0.1290 (4)</td>
<td rowspan="1" colspan="1">−0.2784 (5)</td>
<td rowspan="1" colspan="1">0.0520 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22A</td>
<td rowspan="1" colspan="1">0.2544</td>
<td rowspan="1" colspan="1">0.0971</td>
<td rowspan="1" colspan="1">−0.3212</td>
<td rowspan="1" colspan="1">0.078*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22B</td>
<td rowspan="1" colspan="1">0.2443</td>
<td rowspan="1" colspan="1">0.1671</td>
<td rowspan="1" colspan="1">−0.2140</td>
<td rowspan="1" colspan="1">0.078*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22C</td>
<td rowspan="1" colspan="1">0.1162</td>
<td rowspan="1" colspan="1">0.1671</td>
<td rowspan="1" colspan="1">−0.3364</td>
<td rowspan="1" colspan="1">0.078*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.0446 (5)</td>
<td rowspan="1" colspan="1">0.1575 (3)</td>
<td rowspan="1" colspan="1">−0.0477 (4)</td>
<td rowspan="1" colspan="1">0.0329 (11)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4N</td>
<td rowspan="1" colspan="1">0.151 (6)</td>
<td rowspan="1" colspan="1">0.163 (4)</td>
<td rowspan="1" colspan="1">−0.013 (4)</td>
<td rowspan="1" colspan="1">0.040*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">−0.0317 (6)</td>
<td rowspan="1" colspan="1">0.2444 (4)</td>
<td rowspan="1" colspan="1">0.1013 (4)</td>
<td rowspan="1" colspan="1">0.0457 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H5N</td>
<td rowspan="1" colspan="1">0.078 (7)</td>
<td rowspan="1" colspan="1">0.242 (4)</td>
<td rowspan="1" colspan="1">0.141 (5)</td>
<td rowspan="1" colspan="1">0.055*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H6N</td>
<td rowspan="1" colspan="1">−0.104 (7)</td>
<td rowspan="1" colspan="1">0.256 (4)</td>
<td rowspan="1" colspan="1">0.130 (5)</td>
<td rowspan="1" colspan="1">0.055*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">−0.24072 (14)</td>
<td rowspan="1" colspan="1">0.17401 (9)</td>
<td rowspan="1" colspan="1">−0.08375 (12)</td>
<td rowspan="1" colspan="1">0.0386 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C23</td>
<td rowspan="1" colspan="1">0.7409 (6)</td>
<td rowspan="1" colspan="1">0.2901 (4)</td>
<td rowspan="1" colspan="1">0.3641 (5)</td>
<td rowspan="1" colspan="1">0.0358 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C24</td>
<td rowspan="1" colspan="1">0.5781 (6)</td>
<td rowspan="1" colspan="1">0.2738 (4)</td>
<td rowspan="1" colspan="1">0.3122 (5)</td>
<td rowspan="1" colspan="1">0.0392 (14)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H24</td>
<td rowspan="1" colspan="1">0.5076</td>
<td rowspan="1" colspan="1">0.2871</td>
<td rowspan="1" colspan="1">0.3621</td>
<td rowspan="1" colspan="1">0.047*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C25</td>
<td rowspan="1" colspan="1">0.5242 (6)</td>
<td rowspan="1" colspan="1">0.2420 (4)</td>
<td rowspan="1" colspan="1">0.2013 (5)</td>
<td rowspan="1" colspan="1">0.0380 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H25</td>
<td rowspan="1" colspan="1">0.5942</td>
<td rowspan="1" colspan="1">0.2310</td>
<td rowspan="1" colspan="1">0.1502</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C26</td>
<td rowspan="1" colspan="1">0.3622 (6)</td>
<td rowspan="1" colspan="1">0.2223 (4)</td>
<td rowspan="1" colspan="1">0.1512 (5)</td>
<td rowspan="1" colspan="1">0.0371 (14)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.7763 (4)</td>
<td rowspan="1" colspan="1">0.3234 (3)</td>
<td rowspan="1" colspan="1">0.4689 (3)</td>
<td rowspan="1" colspan="1">0.0469 (10)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.8346 (4)</td>
<td rowspan="1" colspan="1">0.2695 (3)</td>
<td rowspan="1" colspan="1">0.2995 (3)</td>
<td rowspan="1" colspan="1">0.0591 (12)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.3301 (4)</td>
<td rowspan="1" colspan="1">0.1922 (3)</td>
<td rowspan="1" colspan="1">0.0429 (3)</td>
<td rowspan="1" colspan="1">0.0473 (11)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.2689 (4)</td>
<td rowspan="1" colspan="1">0.2349 (4)</td>
<td rowspan="1" colspan="1">0.2157 (3)</td>
<td rowspan="1" colspan="1">0.0642 (14)</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e9323" sec-type="tablewrapadps"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e9335"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.031 (3)</td>
<td rowspan="1" colspan="1">0.003 (2)</td>
<td rowspan="1" colspan="1">0.003 (2)</td>
<td rowspan="1" colspan="1">−0.002 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.040 (3)</td>
<td rowspan="1" colspan="1">0.053 (4)</td>
<td rowspan="1" colspan="1">0.042 (3)</td>
<td rowspan="1" colspan="1">0.004 (3)</td>
<td rowspan="1" colspan="1">−0.001 (3)</td>
<td rowspan="1" colspan="1">−0.011 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.039 (3)</td>
<td rowspan="1" colspan="1">0.040 (3)</td>
<td rowspan="1" colspan="1">0.033 (3)</td>
<td rowspan="1" colspan="1">0.001 (3)</td>
<td rowspan="1" colspan="1">0.008 (3)</td>
<td rowspan="1" colspan="1">−0.007 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.041 (3)</td>
<td rowspan="1" colspan="1">0.026 (3)</td>
<td rowspan="1" colspan="1">0.025 (3)</td>
<td rowspan="1" colspan="1">−0.002 (3)</td>
<td rowspan="1" colspan="1">0.003 (2)</td>
<td rowspan="1" colspan="1">−0.003 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.039 (3)</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.022 (3)</td>
<td rowspan="1" colspan="1">−0.004 (2)</td>
<td rowspan="1" colspan="1">0.007 (2)</td>
<td rowspan="1" colspan="1">0.000 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.064 (4)</td>
<td rowspan="1" colspan="1">0.073 (5)</td>
<td rowspan="1" colspan="1">0.048 (4)</td>
<td rowspan="1" colspan="1">−0.007 (3)</td>
<td rowspan="1" colspan="1">−0.028 (3)</td>
<td rowspan="1" colspan="1">0.007 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.070 (5)</td>
<td rowspan="1" colspan="1">0.058 (5)</td>
<td rowspan="1" colspan="1">0.090 (5)</td>
<td rowspan="1" colspan="1">−0.021 (4)</td>
<td rowspan="1" colspan="1">−0.006 (4)</td>
<td rowspan="1" colspan="1">−0.004 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.047 (4)</td>
<td rowspan="1" colspan="1">0.064 (4)</td>
<td rowspan="1" colspan="1">0.047 (4)</td>
<td rowspan="1" colspan="1">−0.003 (3)</td>
<td rowspan="1" colspan="1">0.022 (3)</td>
<td rowspan="1" colspan="1">0.002 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.085 (5)</td>
<td rowspan="1" colspan="1">0.060 (5)</td>
<td rowspan="1" colspan="1">0.077 (5)</td>
<td rowspan="1" colspan="1">0.025 (4)</td>
<td rowspan="1" colspan="1">0.044 (4)</td>
<td rowspan="1" colspan="1">0.015 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.030 (2)</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.024 (2)</td>
<td rowspan="1" colspan="1">−0.001 (2)</td>
<td rowspan="1" colspan="1">0.006 (2)</td>
<td rowspan="1" colspan="1">0.000 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.064 (4)</td>
<td rowspan="1" colspan="1">0.037 (3)</td>
<td rowspan="1" colspan="1">0.003 (3)</td>
<td rowspan="1" colspan="1">0.007 (2)</td>
<td rowspan="1" colspan="1">−0.013 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0327 (7)</td>
<td rowspan="1" colspan="1">0.0473 (9)</td>
<td rowspan="1" colspan="1">0.0377 (8)</td>
<td rowspan="1" colspan="1">0.0049 (7)</td>
<td rowspan="1" colspan="1">0.0045 (6)</td>
<td rowspan="1" colspan="1">−0.0037 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.039 (3)</td>
<td rowspan="1" colspan="1">0.033 (3)</td>
<td rowspan="1" colspan="1">0.029 (3)</td>
<td rowspan="1" colspan="1">0.001 (3)</td>
<td rowspan="1" colspan="1">0.005 (2)</td>
<td rowspan="1" colspan="1">0.002 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.038 (3)</td>
<td rowspan="1" colspan="1">0.043 (4)</td>
<td rowspan="1" colspan="1">0.039 (3)</td>
<td rowspan="1" colspan="1">−0.005 (3)</td>
<td rowspan="1" colspan="1">0.001 (3)</td>
<td rowspan="1" colspan="1">0.002 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.046 (3)</td>
<td rowspan="1" colspan="1">0.066 (4)</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.003 (3)</td>
<td rowspan="1" colspan="1">0.000 (3)</td>
<td rowspan="1" colspan="1">−0.018 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.049 (4)</td>
<td rowspan="1" colspan="1">0.053 (4)</td>
<td rowspan="1" colspan="1">0.043 (3)</td>
<td rowspan="1" colspan="1">−0.002 (3)</td>
<td rowspan="1" colspan="1">0.004 (3)</td>
<td rowspan="1" colspan="1">−0.017 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.041 (3)</td>
<td rowspan="1" colspan="1">0.031 (3)</td>
<td rowspan="1" colspan="1">0.002 (3)</td>
<td rowspan="1" colspan="1">0.007 (2)</td>
<td rowspan="1" colspan="1">−0.005 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.031 (3)</td>
<td rowspan="1" colspan="1">0.029 (3)</td>
<td rowspan="1" colspan="1">0.024 (3)</td>
<td rowspan="1" colspan="1">0.000 (2)</td>
<td rowspan="1" colspan="1">0.000 (2)</td>
<td rowspan="1" colspan="1">0.003 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.036 (3)</td>
<td rowspan="1" colspan="1">0.035 (4)</td>
<td rowspan="1" colspan="1">0.030 (3)</td>
<td rowspan="1" colspan="1">0.005 (2)</td>
<td rowspan="1" colspan="1">0.008 (3)</td>
<td rowspan="1" colspan="1">−0.001 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.068 (4)</td>
<td rowspan="1" colspan="1">0.055 (4)</td>
<td rowspan="1" colspan="1">0.070 (4)</td>
<td rowspan="1" colspan="1">−0.023 (4)</td>
<td rowspan="1" colspan="1">0.001 (4)</td>
<td rowspan="1" colspan="1">−0.004 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">0.047 (4)</td>
<td rowspan="1" colspan="1">0.068 (5)</td>
<td rowspan="1" colspan="1">0.048 (4)</td>
<td rowspan="1" colspan="1">0.000 (3)</td>
<td rowspan="1" colspan="1">0.000 (3)</td>
<td rowspan="1" colspan="1">−0.003 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.054 (4)</td>
<td rowspan="1" colspan="1">0.044 (4)</td>
<td rowspan="1" colspan="1">0.046 (3)</td>
<td rowspan="1" colspan="1">0.016 (3)</td>
<td rowspan="1" colspan="1">0.000 (3)</td>
<td rowspan="1" colspan="1">−0.007 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.053 (4)</td>
<td rowspan="1" colspan="1">0.064 (5)</td>
<td rowspan="1" colspan="1">0.044 (4)</td>
<td rowspan="1" colspan="1">−0.002 (3)</td>
<td rowspan="1" colspan="1">0.021 (3)</td>
<td rowspan="1" colspan="1">−0.006 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.027 (2)</td>
<td rowspan="1" colspan="1">0.043 (3)</td>
<td rowspan="1" colspan="1">0.028 (2)</td>
<td rowspan="1" colspan="1">0.000 (2)</td>
<td rowspan="1" colspan="1">0.0033 (19)</td>
<td rowspan="1" colspan="1">−0.003 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.071 (4)</td>
<td rowspan="1" colspan="1">0.033 (3)</td>
<td rowspan="1" colspan="1">0.009 (3)</td>
<td rowspan="1" colspan="1">0.011 (2)</td>
<td rowspan="1" colspan="1">−0.012 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">0.0323 (7)</td>
<td rowspan="1" colspan="1">0.0488 (10)</td>
<td rowspan="1" colspan="1">0.0352 (8)</td>
<td rowspan="1" colspan="1">0.0019 (7)</td>
<td rowspan="1" colspan="1">0.0081 (6)</td>
<td rowspan="1" colspan="1">0.0029 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C23</td>
<td rowspan="1" colspan="1">0.033 (3)</td>
<td rowspan="1" colspan="1">0.040 (4)</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">−0.002 (3)</td>
<td rowspan="1" colspan="1">0.008 (3)</td>
<td rowspan="1" colspan="1">0.000 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C24</td>
<td rowspan="1" colspan="1">0.032 (3)</td>
<td rowspan="1" colspan="1">0.047 (4)</td>
<td rowspan="1" colspan="1">0.040 (4)</td>
<td rowspan="1" colspan="1">−0.004 (3)</td>
<td rowspan="1" colspan="1">0.011 (3)</td>
<td rowspan="1" colspan="1">−0.008 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C25</td>
<td rowspan="1" colspan="1">0.035 (3)</td>
<td rowspan="1" colspan="1">0.050 (4)</td>
<td rowspan="1" colspan="1">0.031 (3)</td>
<td rowspan="1" colspan="1">−0.002 (3)</td>
<td rowspan="1" colspan="1">0.011 (3)</td>
<td rowspan="1" colspan="1">−0.003 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C26</td>
<td rowspan="1" colspan="1">0.036 (3)</td>
<td rowspan="1" colspan="1">0.042 (4)</td>
<td rowspan="1" colspan="1">0.032 (3)</td>
<td rowspan="1" colspan="1">0.000 (3)</td>
<td rowspan="1" colspan="1">0.004 (3)</td>
<td rowspan="1" colspan="1">−0.002 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.036 (2)</td>
<td rowspan="1" colspan="1">0.072 (3)</td>
<td rowspan="1" colspan="1">0.031 (2)</td>
<td rowspan="1" colspan="1">−0.010 (2)</td>
<td rowspan="1" colspan="1">0.0048 (17)</td>
<td rowspan="1" colspan="1">−0.019 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">0.108 (4)</td>
<td rowspan="1" colspan="1">0.033 (2)</td>
<td rowspan="1" colspan="1">−0.007 (2)</td>
<td rowspan="1" colspan="1">0.0091 (19)</td>
<td rowspan="1" colspan="1">−0.020 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.037 (2)</td>
<td rowspan="1" colspan="1">0.071 (3)</td>
<td rowspan="1" colspan="1">0.033 (2)</td>
<td rowspan="1" colspan="1">−0.0045 (19)</td>
<td rowspan="1" colspan="1">0.0055 (17)</td>
<td rowspan="1" colspan="1">−0.017 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.035 (2)</td>
<td rowspan="1" colspan="1">0.121 (4)</td>
<td rowspan="1" colspan="1">0.039 (2)</td>
<td rowspan="1" colspan="1">−0.010 (2)</td>
<td rowspan="1" colspan="1">0.013 (2)</td>
<td rowspan="1" colspan="1">−0.028 (2)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e9970" sec-type="tablewrapgeomlong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e9980"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.344 (7)</td>
<td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.496 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.514 (7)</td>
<td rowspan="1" colspan="1">C12—S2</td>
<td rowspan="1" colspan="1">1.761 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—S1</td>
<td rowspan="1" colspan="1">1.744 (5)</td>
<td rowspan="1" colspan="1">C13—C19</td>
<td rowspan="1" colspan="1">1.527 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A</td>
<td rowspan="1" colspan="1">1.520 (9)</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.532 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8</td>
<td rowspan="1" colspan="1">1.524 (8)</td>
<td rowspan="1" colspan="1">C13—C20</td>
<td rowspan="1" colspan="1">1.533 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9</td>
<td rowspan="1" colspan="1">1.551 (9)</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.526 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B</td>
<td rowspan="1" colspan="1">1.66 (3)</td>
<td rowspan="1" colspan="1">C14—H14A</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A</td>
<td rowspan="1" colspan="1">1.541 (14)</td>
<td rowspan="1" colspan="1">C14—H14B</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—H3A1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C15—C16</td>
<td rowspan="1" colspan="1">1.542 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—H3A2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C15—H15A</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5</td>
<td rowspan="1" colspan="1">1.575 (10)</td>
<td rowspan="1" colspan="1">C15—H15B</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H4A1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.513 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H4A2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C16—C22</td>
<td rowspan="1" colspan="1">1.523 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B</td>
<td rowspan="1" colspan="1">1.53 (5)</td>
<td rowspan="1" colspan="1">C16—C21</td>
<td rowspan="1" colspan="1">1.536 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—H3B1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C17—N3</td>
<td rowspan="1" colspan="1">1.404 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—H3B2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C18—N4</td>
<td rowspan="1" colspan="1">1.319 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5</td>
<td rowspan="1" colspan="1">1.47 (2)</td>
<td rowspan="1" colspan="1">C18—N3</td>
<td rowspan="1" colspan="1">1.320 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H4B1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C18—S2</td>
<td rowspan="1" colspan="1">1.723 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H4B2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C19—H19A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.504 (7)</td>
<td rowspan="1" colspan="1">C19—H19B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10</td>
<td rowspan="1" colspan="1">1.526 (8)</td>
<td rowspan="1" colspan="1">C19—H19C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11</td>
<td rowspan="1" colspan="1">1.540 (8)</td>
<td rowspan="1" colspan="1">C20—H20A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1</td>
<td rowspan="1" colspan="1">1.401 (6)</td>
<td rowspan="1" colspan="1">C20—H20B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2</td>
<td rowspan="1" colspan="1">1.318 (6)</td>
<td rowspan="1" colspan="1">C20—H20C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1</td>
<td rowspan="1" colspan="1">1.325 (6)</td>
<td rowspan="1" colspan="1">C21—H21A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—S1</td>
<td rowspan="1" colspan="1">1.721 (5)</td>
<td rowspan="1" colspan="1">C21—H21B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C21—H21C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C22—H22A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C22—H22B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C22—H22C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N3—H4N</td>
<td rowspan="1" colspan="1">0.96 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N4—H5N</td>
<td rowspan="1" colspan="1">1.00 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N4—H6N</td>
<td rowspan="1" colspan="1">0.81 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C23—O1</td>
<td rowspan="1" colspan="1">1.251 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C23—O2</td>
<td rowspan="1" colspan="1">1.258 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C23—C24</td>
<td rowspan="1" colspan="1">1.484 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C24—C25</td>
<td rowspan="1" colspan="1">1.321 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C24—H24</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1N</td>
<td rowspan="1" colspan="1">0.85 (5)</td>
<td rowspan="1" colspan="1">C25—C26</td>
<td rowspan="1" colspan="1">1.483 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2N</td>
<td rowspan="1" colspan="1">0.94 (6)</td>
<td rowspan="1" colspan="1">C25—H25</td>
<td rowspan="1" colspan="1">0.9500</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3N</td>
<td rowspan="1" colspan="1">0.91 (6)</td>
<td rowspan="1" colspan="1">C26—O4</td>
<td rowspan="1" colspan="1">1.232 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12—C17</td>
<td rowspan="1" colspan="1">1.345 (7)</td>
<td rowspan="1" colspan="1">C26—O3</td>
<td rowspan="1" colspan="1">1.267 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2</td>
<td rowspan="1" colspan="1">126.7 (5)</td>
<td rowspan="1" colspan="1">C7—N2—H3N</td>
<td rowspan="1" colspan="1">119 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—S1</td>
<td rowspan="1" colspan="1">111.2 (4)</td>
<td rowspan="1" colspan="1">H2N—N2—H3N</td>
<td rowspan="1" colspan="1">118 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—S1</td>
<td rowspan="1" colspan="1">122.1 (4)</td>
<td rowspan="1" colspan="1">C7—S1—C1</td>
<td rowspan="1" colspan="1">90.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3A</td>
<td rowspan="1" colspan="1">106.1 (5)</td>
<td rowspan="1" colspan="1">C17—C12—C13</td>
<td rowspan="1" colspan="1">127.0 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C8</td>
<td rowspan="1" colspan="1">109.5 (5)</td>
<td rowspan="1" colspan="1">C17—C12—S2</td>
<td rowspan="1" colspan="1">110.0 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C2—C8</td>
<td rowspan="1" colspan="1">118.0 (6)</td>
<td rowspan="1" colspan="1">C13—C12—S2</td>
<td rowspan="1" colspan="1">122.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C9</td>
<td rowspan="1" colspan="1">109.7 (5)</td>
<td rowspan="1" colspan="1">C12—C13—C19</td>
<td rowspan="1" colspan="1">110.8 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C2—C9</td>
<td rowspan="1" colspan="1">105.5 (6)</td>
<td rowspan="1" colspan="1">C12—C13—C14</td>
<td rowspan="1" colspan="1">106.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C9</td>
<td rowspan="1" colspan="1">107.7 (5)</td>
<td rowspan="1" colspan="1">C19—C13—C14</td>
<td rowspan="1" colspan="1">111.1 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3B</td>
<td rowspan="1" colspan="1">102.3 (11)</td>
<td rowspan="1" colspan="1">C12—C13—C20</td>
<td rowspan="1" colspan="1">110.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3B</td>
<td rowspan="1" colspan="1">89.8 (15)</td>
<td rowspan="1" colspan="1">C19—C13—C20</td>
<td rowspan="1" colspan="1">108.2 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3B</td>
<td rowspan="1" colspan="1">134.9 (15)</td>
<td rowspan="1" colspan="1">C14—C13—C20</td>
<td rowspan="1" colspan="1">108.8 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—C4A</td>
<td rowspan="1" colspan="1">111.1 (9)</td>
<td rowspan="1" colspan="1">C15—C14—C13</td>
<td rowspan="1" colspan="1">113.0 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—H3A1</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C15—C14—H14A</td>
<td rowspan="1" colspan="1">109.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—H3A1</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C13—C14—H14A</td>
<td rowspan="1" colspan="1">109.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—H3A2</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C15—C14—H14B</td>
<td rowspan="1" colspan="1">109.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—H3A2</td>
<td rowspan="1" colspan="1">109.4</td>
<td rowspan="1" colspan="1">C13—C14—H14B</td>
<td rowspan="1" colspan="1">109.0</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A1—C3A—H3A2</td>
<td rowspan="1" colspan="1">108.0</td>
<td rowspan="1" colspan="1">H14A—C14—H14B</td>
<td rowspan="1" colspan="1">107.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5</td>
<td rowspan="1" colspan="1">111.7 (8)</td>
<td rowspan="1" colspan="1">C14—C15—C16</td>
<td rowspan="1" colspan="1">114.5 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—H4A1</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">C14—C15—H15A</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4A—H4A1</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">C16—C15—H15A</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—H4A2</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">C14—C15—H15B</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4A—H4A2</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">C16—C15—H15B</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A1—C4A—H4A2</td>
<td rowspan="1" colspan="1">107.9</td>
<td rowspan="1" colspan="1">H15A—C15—H15B</td>
<td rowspan="1" colspan="1">107.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—C2</td>
<td rowspan="1" colspan="1">114 (3)</td>
<td rowspan="1" colspan="1">C17—C16—C22</td>
<td rowspan="1" colspan="1">109.7 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—H3B1</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C17—C16—C21</td>
<td rowspan="1" colspan="1">110.2 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—H3B1</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C22—C16—C21</td>
<td rowspan="1" colspan="1">109.8 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—H3B2</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C17—C16—C15</td>
<td rowspan="1" colspan="1">106.8 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—H3B2</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C22—C16—C15</td>
<td rowspan="1" colspan="1">111.4 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B1—C3B—H3B2</td>
<td rowspan="1" colspan="1">107.6</td>
<td rowspan="1" colspan="1">C21—C16—C15</td>
<td rowspan="1" colspan="1">108.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—C3B</td>
<td rowspan="1" colspan="1">112 (3)</td>
<td rowspan="1" colspan="1">C12—C17—N3</td>
<td rowspan="1" colspan="1">113.5 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—H4B1</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">C12—C17—C16</td>
<td rowspan="1" colspan="1">125.6 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—H4B1</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">N3—C17—C16</td>
<td rowspan="1" colspan="1">120.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—H4B2</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">N4—C18—N3</td>
<td rowspan="1" colspan="1">122.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—H4B2</td>
<td rowspan="1" colspan="1">109.3</td>
<td rowspan="1" colspan="1">N4—C18—S2</td>
<td rowspan="1" colspan="1">124.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B1—C4B—H4B2</td>
<td rowspan="1" colspan="1">107.9</td>
<td rowspan="1" colspan="1">N3—C18—S2</td>
<td rowspan="1" colspan="1">112.1 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C6</td>
<td rowspan="1" colspan="1">112.1 (10)</td>
<td rowspan="1" colspan="1">C13—C19—H19A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C10</td>
<td rowspan="1" colspan="1">121.4 (12)</td>
<td rowspan="1" colspan="1">C13—C19—H19B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C10</td>
<td rowspan="1" colspan="1">110.5 (5)</td>
<td rowspan="1" colspan="1">H19A—C19—H19B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C11</td>
<td rowspan="1" colspan="1">92.1 (15)</td>
<td rowspan="1" colspan="1">C13—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C11</td>
<td rowspan="1" colspan="1">110.1 (4)</td>
<td rowspan="1" colspan="1">H19A—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C11</td>
<td rowspan="1" colspan="1">108.9 (5)</td>
<td rowspan="1" colspan="1">H19B—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4A</td>
<td rowspan="1" colspan="1">105.1 (5)</td>
<td rowspan="1" colspan="1">C13—C20—H20A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C4A</td>
<td rowspan="1" colspan="1">106.4 (5)</td>
<td rowspan="1" colspan="1">C13—C20—H20B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C4A</td>
<td rowspan="1" colspan="1">115.8 (6)</td>
<td rowspan="1" colspan="1">H20A—C20—H20B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1</td>
<td rowspan="1" colspan="1">112.5 (4)</td>
<td rowspan="1" colspan="1">C13—C20—H20C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—C5</td>
<td rowspan="1" colspan="1">126.0 (4)</td>
<td rowspan="1" colspan="1">H20A—C20—H20C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C6—C5</td>
<td rowspan="1" colspan="1">121.5 (4)</td>
<td rowspan="1" colspan="1">H20B—C20—H20C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1</td>
<td rowspan="1" colspan="1">123.7 (5)</td>
<td rowspan="1" colspan="1">C16—C21—H21A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1</td>
<td rowspan="1" colspan="1">124.4 (4)</td>
<td rowspan="1" colspan="1">C16—C21—H21B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C7—S1</td>
<td rowspan="1" colspan="1">111.8 (4)</td>
<td rowspan="1" colspan="1">H21A—C21—H21B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C21—H21C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H21A—C21—H21C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H21B—C21—H21C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C22—H22A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C22—H22B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8B—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H22A—C22—H22B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C22—H22C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H22A—C22—H22C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H22B—C22—H22C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N3—C17</td>
<td rowspan="1" colspan="1">113.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N3—H4N</td>
<td rowspan="1" colspan="1">123 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9B—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C17—N3—H4N</td>
<td rowspan="1" colspan="1">123 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N4—H5N</td>
<td rowspan="1" colspan="1">112 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N4—H6N</td>
<td rowspan="1" colspan="1">115 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H10A—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H5N—N4—H6N</td>
<td rowspan="1" colspan="1">130 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—S2—C12</td>
<td rowspan="1" colspan="1">90.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H10A—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O1—C23—O2</td>
<td rowspan="1" colspan="1">124.2 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">H10B—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O1—C23—C24</td>
<td rowspan="1" colspan="1">118.1 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11—H11A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O2—C23—C24</td>
<td rowspan="1" colspan="1">117.7 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C25—C24—C23</td>
<td rowspan="1" colspan="1">124.6 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">H11A—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C25—C24—H24</td>
<td rowspan="1" colspan="1">117.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C23—C24—H24</td>
<td rowspan="1" colspan="1">117.7</td>
</tr>
<tr><td rowspan="1" colspan="1">H11A—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C24—C25—C26</td>
<td rowspan="1" colspan="1">124.6 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">H11B—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C24—C25—H25</td>
<td rowspan="1" colspan="1">117.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1—C6</td>
<td rowspan="1" colspan="1">114.1 (4)</td>
<td rowspan="1" colspan="1">C26—C25—H25</td>
<td rowspan="1" colspan="1">117.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1—H1N</td>
<td rowspan="1" colspan="1">119 (3)</td>
<td rowspan="1" colspan="1">O4—C26—O3</td>
<td rowspan="1" colspan="1">124.4 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1—H1N</td>
<td rowspan="1" colspan="1">126 (3)</td>
<td rowspan="1" colspan="1">O4—C26—C25</td>
<td rowspan="1" colspan="1">119.2 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2—H2N</td>
<td rowspan="1" colspan="1">117 (4)</td>
<td rowspan="1" colspan="1">O3—C26—C25</td>
<td rowspan="1" colspan="1">116.3 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C3A</td>
<td rowspan="1" colspan="1">−15.4 (9)</td>
<td rowspan="1" colspan="1">N1—C7—S1—C1</td>
<td rowspan="1" colspan="1">−0.6 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C3A</td>
<td rowspan="1" colspan="1">165.0 (6)</td>
<td rowspan="1" colspan="1">C6—C1—S1—C7</td>
<td rowspan="1" colspan="1">0.8 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C8</td>
<td rowspan="1" colspan="1">113.1 (6)</td>
<td rowspan="1" colspan="1">C2—C1—S1—C7</td>
<td rowspan="1" colspan="1">−179.5 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C8</td>
<td rowspan="1" colspan="1">−66.6 (6)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C19</td>
<td rowspan="1" colspan="1">107.5 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C9</td>
<td rowspan="1" colspan="1">−128.9 (6)</td>
<td rowspan="1" colspan="1">S2—C12—C13—C19</td>
<td rowspan="1" colspan="1">−75.3 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C9</td>
<td rowspan="1" colspan="1">51.4 (6)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C14</td>
<td rowspan="1" colspan="1">−13.7 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C3B</td>
<td rowspan="1" colspan="1">18.8 (17)</td>
<td rowspan="1" colspan="1">S2—C12—C13—C14</td>
<td rowspan="1" colspan="1">163.5 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C3B</td>
<td rowspan="1" colspan="1">−160.8 (16)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C20</td>
<td rowspan="1" colspan="1">−132.2 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3A—C4A</td>
<td rowspan="1" colspan="1">47.8 (10)</td>
<td rowspan="1" colspan="1">S2—C12—C13—C20</td>
<td rowspan="1" colspan="1">45.0 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3A—C4A</td>
<td rowspan="1" colspan="1">−75.5 (9)</td>
<td rowspan="1" colspan="1">C12—C13—C14—C15</td>
<td rowspan="1" colspan="1">44.1 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3A—C4A</td>
<td rowspan="1" colspan="1">164.1 (8)</td>
<td rowspan="1" colspan="1">C19—C13—C14—C15</td>
<td rowspan="1" colspan="1">−77.0 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—C4A—C5</td>
<td rowspan="1" colspan="1">−69.2 (12)</td>
<td rowspan="1" colspan="1">C20—C13—C14—C15</td>
<td rowspan="1" colspan="1">163.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3B—C4B</td>
<td rowspan="1" colspan="1">−48 (3)</td>
<td rowspan="1" colspan="1">C13—C14—C15—C16</td>
<td rowspan="1" colspan="1">−62.5 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3B—C4B</td>
<td rowspan="1" colspan="1">−158 (3)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C17</td>
<td rowspan="1" colspan="1">40.9 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3B—C4B</td>
<td rowspan="1" colspan="1">87 (3)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C22</td>
<td rowspan="1" colspan="1">−78.9 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—C4B—C5</td>
<td rowspan="1" colspan="1">62 (4)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C21</td>
<td rowspan="1" colspan="1">159.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5—C6</td>
<td rowspan="1" colspan="1">−38 (3)</td>
<td rowspan="1" colspan="1">C13—C12—C17—N3</td>
<td rowspan="1" colspan="1">176.7 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5—C10</td>
<td rowspan="1" colspan="1">95 (3)</td>
<td rowspan="1" colspan="1">S2—C12—C17—N3</td>
<td rowspan="1" colspan="1">−0.8 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5—C11</td>
<td rowspan="1" colspan="1">−151 (3)</td>
<td rowspan="1" colspan="1">C13—C12—C17—C16</td>
<td rowspan="1" colspan="1">−3.4 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5—C6</td>
<td rowspan="1" colspan="1">47.3 (10)</td>
<td rowspan="1" colspan="1">S2—C12—C17—C16</td>
<td rowspan="1" colspan="1">179.1 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5—C10</td>
<td rowspan="1" colspan="1">164.5 (8)</td>
<td rowspan="1" colspan="1">C22—C16—C17—C12</td>
<td rowspan="1" colspan="1">111.1 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5—C11</td>
<td rowspan="1" colspan="1">−74.4 (10)</td>
<td rowspan="1" colspan="1">C21—C16—C17—C12</td>
<td rowspan="1" colspan="1">−127.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—N1</td>
<td rowspan="1" colspan="1">179.6 (5)</td>
<td rowspan="1" colspan="1">C15—C16—C17—C12</td>
<td rowspan="1" colspan="1">−9.8 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C6—N1</td>
<td rowspan="1" colspan="1">−0.7 (5)</td>
<td rowspan="1" colspan="1">C22—C16—C17—N3</td>
<td rowspan="1" colspan="1">−69.1 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td>
<td rowspan="1" colspan="1">−0.9 (9)</td>
<td rowspan="1" colspan="1">C21—C16—C17—N3</td>
<td rowspan="1" colspan="1">51.9 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C6—C5</td>
<td rowspan="1" colspan="1">178.8 (4)</td>
<td rowspan="1" colspan="1">C15—C16—C17—N3</td>
<td rowspan="1" colspan="1">170.1 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C6—C1</td>
<td rowspan="1" colspan="1">9.7 (17)</td>
<td rowspan="1" colspan="1">N4—C18—N3—C17</td>
<td rowspan="1" colspan="1">−178.6 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C6—C1</td>
<td rowspan="1" colspan="1">−129.1 (5)</td>
<td rowspan="1" colspan="1">S2—C18—N3—C17</td>
<td rowspan="1" colspan="1">−1.4 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C6—C1</td>
<td rowspan="1" colspan="1">110.6 (6)</td>
<td rowspan="1" colspan="1">C12—C17—N3—C18</td>
<td rowspan="1" colspan="1">1.5 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5—C6—C1</td>
<td rowspan="1" colspan="1">−14.7 (8)</td>
<td rowspan="1" colspan="1">C16—C17—N3—C18</td>
<td rowspan="1" colspan="1">−178.4 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C6—N1</td>
<td rowspan="1" colspan="1">−170.9 (16)</td>
<td rowspan="1" colspan="1">N4—C18—S2—C12</td>
<td rowspan="1" colspan="1">177.9 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C6—N1</td>
<td rowspan="1" colspan="1">50.4 (6)</td>
<td rowspan="1" colspan="1">N3—C18—S2—C12</td>
<td rowspan="1" colspan="1">0.8 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C6—N1</td>
<td rowspan="1" colspan="1">−69.9 (6)</td>
<td rowspan="1" colspan="1">C17—C12—S2—C18</td>
<td rowspan="1" colspan="1">0.0 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5—C6—N1</td>
<td rowspan="1" colspan="1">164.7 (6)</td>
<td rowspan="1" colspan="1">C13—C12—S2—C18</td>
<td rowspan="1" colspan="1">−177.6 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1—C6</td>
<td rowspan="1" colspan="1">177.7 (5)</td>
<td rowspan="1" colspan="1">O1—C23—C24—C25</td>
<td rowspan="1" colspan="1">177.5 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C7—N1—C6</td>
<td rowspan="1" colspan="1">0.3 (6)</td>
<td rowspan="1" colspan="1">O2—C23—C24—C25</td>
<td rowspan="1" colspan="1">−2.4 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1—C7</td>
<td rowspan="1" colspan="1">0.3 (6)</td>
<td rowspan="1" colspan="1">C23—C24—C25—C26</td>
<td rowspan="1" colspan="1">177.5 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—N1—C7</td>
<td rowspan="1" colspan="1">−179.2 (5)</td>
<td rowspan="1" colspan="1">C24—C25—C26—O4</td>
<td rowspan="1" colspan="1">−0.8 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1—C1</td>
<td rowspan="1" colspan="1">−177.9 (5)</td>
<td rowspan="1" colspan="1">C24—C25—C26—O3</td>
<td rowspan="1" colspan="1">179.9 (5)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e11527" sec-type="tablewraphbondslong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
fumarate (IV) </label>
<title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e11536"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H</td>
<td rowspan="1" colspan="1">H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1<italic>N</italic>
···O1</td>
<td rowspan="1" colspan="1">0.85 (5)</td>
<td rowspan="1" colspan="1">1.84 (5)</td>
<td rowspan="1" colspan="1">2.670 (5)</td>
<td rowspan="1" colspan="1">167 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2<italic>N</italic>
···O2</td>
<td rowspan="1" colspan="1">0.94 (6)</td>
<td rowspan="1" colspan="1">1.77 (6)</td>
<td rowspan="1" colspan="1">2.704 (6)</td>
<td rowspan="1" colspan="1">177 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3<italic>N</italic>
···O4<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.91 (6)</td>
<td rowspan="1" colspan="1">1.90 (6)</td>
<td rowspan="1" colspan="1">2.746 (6)</td>
<td rowspan="1" colspan="1">153 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3—H4<italic>N</italic>
···O3</td>
<td rowspan="1" colspan="1">0.96 (5)</td>
<td rowspan="1" colspan="1">1.67 (5)</td>
<td rowspan="1" colspan="1">2.617 (5)</td>
<td rowspan="1" colspan="1">169 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4—H5<italic>N</italic>
···O4</td>
<td rowspan="1" colspan="1">1.00 (6)</td>
<td rowspan="1" colspan="1">1.75 (6)</td>
<td rowspan="1" colspan="1">2.754 (7)</td>
<td rowspan="1" colspan="1">178 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4—H6<italic>N</italic>
···O2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.81 (6)</td>
<td rowspan="1" colspan="1">2.09 (6)</td>
<td rowspan="1" colspan="1">2.763 (6)</td>
<td rowspan="1" colspan="1">141 (6)</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) <italic>x</italic>
+1, <italic>y</italic>
, <italic>z</italic>
; (ii) <italic>x</italic>
−1, <italic>y</italic>
, <italic>z</italic>
.</p>
</sec>
<sec id="d1e11697" sec-type="tablewrapcrystaldatalong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e11706"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">1.5C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·0.5C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2</sup>
<sup>−</sup>
·0.5C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>−</sup>
·0.5C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 580</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 538.75</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.226 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 8.9437 (3) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 9613 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 14.7253 (4) Å</td>
<td rowspan="1" colspan="1">θ = 2.3–28.0°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 11.2676 (4) Å</td>
<td rowspan="1" colspan="1">µ = 0.22 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 100.493 (3)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 173 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 1459.11 (8) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">Plate, colourless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 2</td>
<td rowspan="1" colspan="1">0.32 × 0.15 × 0.02 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e11858" sec-type="tablewrapdatacollectionlong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e11867"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Rigaku XtaLAB P200 HPC diffractometer</td>
<td rowspan="1" colspan="1">6272 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: rotating anode, Rigaku FR-X</td>
<td rowspan="1" colspan="1">5511 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Rigaku Osmic Confocal Optical System monochromator</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.034</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 29.1°, θ<sub>min</sub>
 = 2.3°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −10→12</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.779, <italic>T</italic>
<sub>max</sub>
 = 1.000</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −19→19</td>
</tr>
<tr><td rowspan="1" colspan="1">19079 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −14→14</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e11969" sec-type="tablewraprefinementdatalong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e11978"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Hydrogen site location: mixed</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.039</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0529<italic>P</italic>
)<sup>2</sup>
 + 0.1056<italic>P</italic>
] where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.094</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 = 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.04</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.26 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">6272 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.25 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">354 parameters</td>
<td rowspan="1" colspan="1">Absolute structure: Flack <italic>x</italic> determined using 2211
quotients
[(<italic>I</italic>
<sup>+</sup>
)-(<italic>I</italic>
<sup>-</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>-</sup>)]
(Parsons <italic>et al.</italic>
, 2013)</td>
</tr>
<tr><td rowspan="1" colspan="1">1 restraint</td>
<td rowspan="1" colspan="1">Absolute structure parameter: 0.00 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e12156" sec-type="specialdetails"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e12166"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e12175" sec-type="tablewrapcoords"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e12187"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1">Occ. (<1)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">1.2888 (3)</td>
<td rowspan="1" colspan="1">0.39542 (19)</td>
<td rowspan="1" colspan="1">0.6860 (2)</td>
<td rowspan="1" colspan="1">0.0263 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">1.3946 (3)</td>
<td rowspan="1" colspan="1">0.4407 (2)</td>
<td rowspan="1" colspan="1">0.7881 (3)</td>
<td rowspan="1" colspan="1">0.0357 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3A</td>
<td rowspan="1" colspan="1">1.2962 (6)</td>
<td rowspan="1" colspan="1">0.5069 (4)</td>
<td rowspan="1" colspan="1">0.8461 (5)</td>
<td rowspan="1" colspan="1">0.0365 (17)*</td>
<td rowspan="1" colspan="1">0.593 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A1</td>
<td rowspan="1" colspan="1">1.2689</td>
<td rowspan="1" colspan="1">0.5598</td>
<td rowspan="1" colspan="1">0.7923</td>
<td rowspan="1" colspan="1">0.044*</td>
<td rowspan="1" colspan="1">0.593 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A2</td>
<td rowspan="1" colspan="1">1.3548</td>
<td rowspan="1" colspan="1">0.5293</td>
<td rowspan="1" colspan="1">0.9237</td>
<td rowspan="1" colspan="1">0.044*</td>
<td rowspan="1" colspan="1">0.593 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A</td>
<td rowspan="1" colspan="1">1.1500 (6)</td>
<td rowspan="1" colspan="1">0.4594 (5)</td>
<td rowspan="1" colspan="1">0.8685 (6)</td>
<td rowspan="1" colspan="1">0.0366 (16)*</td>
<td rowspan="1" colspan="1">0.593 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A1</td>
<td rowspan="1" colspan="1">1.0979</td>
<td rowspan="1" colspan="1">0.4985</td>
<td rowspan="1" colspan="1">0.9198</td>
<td rowspan="1" colspan="1">0.044*</td>
<td rowspan="1" colspan="1">0.593 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A2</td>
<td rowspan="1" colspan="1">1.1768</td>
<td rowspan="1" colspan="1">0.4015</td>
<td rowspan="1" colspan="1">0.9118</td>
<td rowspan="1" colspan="1">0.044*</td>
<td rowspan="1" colspan="1">0.593 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B</td>
<td rowspan="1" colspan="1">1.2917 (10)</td>
<td rowspan="1" colspan="1">0.4598 (8)</td>
<td rowspan="1" colspan="1">0.8865 (9)</td>
<td rowspan="1" colspan="1">0.049 (3)*</td>
<td rowspan="1" colspan="1">0.407 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B1</td>
<td rowspan="1" colspan="1">1.2754</td>
<td rowspan="1" colspan="1">0.4020</td>
<td rowspan="1" colspan="1">0.9271</td>
<td rowspan="1" colspan="1">0.059*</td>
<td rowspan="1" colspan="1">0.407 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B2</td>
<td rowspan="1" colspan="1">1.3468</td>
<td rowspan="1" colspan="1">0.5015</td>
<td rowspan="1" colspan="1">0.9483</td>
<td rowspan="1" colspan="1">0.059*</td>
<td rowspan="1" colspan="1">0.407 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B</td>
<td rowspan="1" colspan="1">1.1399 (9)</td>
<td rowspan="1" colspan="1">0.5005 (7)</td>
<td rowspan="1" colspan="1">0.8353 (8)</td>
<td rowspan="1" colspan="1">0.038 (2)*</td>
<td rowspan="1" colspan="1">0.407 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B1</td>
<td rowspan="1" colspan="1">1.1564</td>
<td rowspan="1" colspan="1">0.5586</td>
<td rowspan="1" colspan="1">0.7954</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1">0.407 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B2</td>
<td rowspan="1" colspan="1">1.0860</td>
<td rowspan="1" colspan="1">0.5143</td>
<td rowspan="1" colspan="1">0.9025</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1">0.407 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">1.0393 (3)</td>
<td rowspan="1" colspan="1">0.4400 (2)</td>
<td rowspan="1" colspan="1">0.7449 (3)</td>
<td rowspan="1" colspan="1">0.0308 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">1.1354 (3)</td>
<td rowspan="1" colspan="1">0.39467 (18)</td>
<td rowspan="1" colspan="1">0.6659 (2)</td>
<td rowspan="1" colspan="1">0.0236 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">1.1723 (3)</td>
<td rowspan="1" colspan="1">0.30960 (19)</td>
<td rowspan="1" colspan="1">0.5050 (2)</td>
<td rowspan="1" colspan="1">0.0265 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">1.4933 (5)</td>
<td rowspan="1" colspan="1">0.3708 (3)</td>
<td rowspan="1" colspan="1">0.8639 (4)</td>
<td rowspan="1" colspan="1">0.0612 (11)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">1.5574</td>
<td rowspan="1" colspan="1">0.4010</td>
<td rowspan="1" colspan="1">0.9324</td>
<td rowspan="1" colspan="1">0.092*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">1.5579</td>
<td rowspan="1" colspan="1">0.3404</td>
<td rowspan="1" colspan="1">0.8146</td>
<td rowspan="1" colspan="1">0.092*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8C</td>
<td rowspan="1" colspan="1">1.4285</td>
<td rowspan="1" colspan="1">0.3258</td>
<td rowspan="1" colspan="1">0.8939</td>
<td rowspan="1" colspan="1">0.092*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">1.5000 (5)</td>
<td rowspan="1" colspan="1">0.5061 (3)</td>
<td rowspan="1" colspan="1">0.7370 (4)</td>
<td rowspan="1" colspan="1">0.0690 (12)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">1.5592</td>
<td rowspan="1" colspan="1">0.5414</td>
<td rowspan="1" colspan="1">0.8030</td>
<td rowspan="1" colspan="1">0.103*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9B</td>
<td rowspan="1" colspan="1">1.4390</td>
<td rowspan="1" colspan="1">0.5474</td>
<td rowspan="1" colspan="1">0.6793</td>
<td rowspan="1" colspan="1">0.103*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9C</td>
<td rowspan="1" colspan="1">1.5691</td>
<td rowspan="1" colspan="1">0.4714</td>
<td rowspan="1" colspan="1">0.6961</td>
<td rowspan="1" colspan="1">0.103*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.9296 (4)</td>
<td rowspan="1" colspan="1">0.3719 (2)</td>
<td rowspan="1" colspan="1">0.7834 (3)</td>
<td rowspan="1" colspan="1">0.0480 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.8715</td>
<td rowspan="1" colspan="1">0.4014</td>
<td rowspan="1" colspan="1">0.8385</td>
<td rowspan="1" colspan="1">0.072*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">0.9869</td>
<td rowspan="1" colspan="1">0.3207</td>
<td rowspan="1" colspan="1">0.8245</td>
<td rowspan="1" colspan="1">0.072*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10C</td>
<td rowspan="1" colspan="1">0.8596</td>
<td rowspan="1" colspan="1">0.3499</td>
<td rowspan="1" colspan="1">0.7121</td>
<td rowspan="1" colspan="1">0.072*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.9468 (5)</td>
<td rowspan="1" colspan="1">0.5170 (3)</td>
<td rowspan="1" colspan="1">0.6769 (4)</td>
<td rowspan="1" colspan="1">0.0669 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.8820</td>
<td rowspan="1" colspan="1">0.5444</td>
<td rowspan="1" colspan="1">0.7285</td>
<td rowspan="1" colspan="1">0.100*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.8830</td>
<td rowspan="1" colspan="1">0.4928</td>
<td rowspan="1" colspan="1">0.6036</td>
<td rowspan="1" colspan="1">0.100*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11C</td>
<td rowspan="1" colspan="1">1.0158</td>
<td rowspan="1" colspan="1">0.5631</td>
<td rowspan="1" colspan="1">0.6547</td>
<td rowspan="1" colspan="1">0.100*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">1.0710 (3)</td>
<td rowspan="1" colspan="1">0.34631 (16)</td>
<td rowspan="1" colspan="1">0.5629 (2)</td>
<td rowspan="1" colspan="1">0.0246 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1N</td>
<td rowspan="1" colspan="1">0.968 (4)</td>
<td rowspan="1" colspan="1">0.335 (2)</td>
<td rowspan="1" colspan="1">0.534 (3)</td>
<td rowspan="1" colspan="1">0.030*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">1.1368 (3)</td>
<td rowspan="1" colspan="1">0.2592 (2)</td>
<td rowspan="1" colspan="1">0.4072 (2)</td>
<td rowspan="1" colspan="1">0.0397 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2N</td>
<td rowspan="1" colspan="1">1.209 (4)</td>
<td rowspan="1" colspan="1">0.241 (3)</td>
<td rowspan="1" colspan="1">0.369 (3)</td>
<td rowspan="1" colspan="1">0.048*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3N</td>
<td rowspan="1" colspan="1">1.047 (4)</td>
<td rowspan="1" colspan="1">0.257 (3)</td>
<td rowspan="1" colspan="1">0.374 (3)</td>
<td rowspan="1" colspan="1">0.048*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">1.35670 (7)</td>
<td rowspan="1" colspan="1">0.33342 (5)</td>
<td rowspan="1" colspan="1">0.57387 (6)</td>
<td rowspan="1" colspan="1">0.03090 (18)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">−0.1518 (3)</td>
<td rowspan="1" colspan="1">0.11232 (19)</td>
<td rowspan="1" colspan="1">−0.1824 (3)</td>
<td rowspan="1" colspan="1">0.0261 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">−0.2459 (4)</td>
<td rowspan="1" colspan="1">0.0700 (2)</td>
<td rowspan="1" colspan="1">−0.2927 (3)</td>
<td rowspan="1" colspan="1">0.0345 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">−0.1355 (4)</td>
<td rowspan="1" colspan="1">0.0472 (2)</td>
<td rowspan="1" colspan="1">−0.3784 (3)</td>
<td rowspan="1" colspan="1">0.0405 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14A</td>
<td rowspan="1" colspan="1">−0.1871</td>
<td rowspan="1" colspan="1">0.0066</td>
<td rowspan="1" colspan="1">−0.4431</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14B</td>
<td rowspan="1" colspan="1">−0.1081</td>
<td rowspan="1" colspan="1">0.1038</td>
<td rowspan="1" colspan="1">−0.4167</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0097 (4)</td>
<td rowspan="1" colspan="1">0.0011 (2)</td>
<td rowspan="1" colspan="1">−0.3133 (3)</td>
<td rowspan="1" colspan="1">0.0426 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15A</td>
<td rowspan="1" colspan="1">0.0715</td>
<td rowspan="1" colspan="1">−0.0172</td>
<td rowspan="1" colspan="1">−0.3738</td>
<td rowspan="1" colspan="1">0.051*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15B</td>
<td rowspan="1" colspan="1">−0.0183</td>
<td rowspan="1" colspan="1">−0.0547</td>
<td rowspan="1" colspan="1">−0.2736</td>
<td rowspan="1" colspan="1">0.051*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.1071 (3)</td>
<td rowspan="1" colspan="1">0.06150 (19)</td>
<td rowspan="1" colspan="1">−0.2180 (3)</td>
<td rowspan="1" colspan="1">0.0295 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.0007 (3)</td>
<td rowspan="1" colspan="1">0.11035 (18)</td>
<td rowspan="1" colspan="1">−0.1495 (2)</td>
<td rowspan="1" colspan="1">0.0245 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">−0.0513 (3)</td>
<td rowspan="1" colspan="1">0.19535 (18)</td>
<td rowspan="1" colspan="1">0.0048 (2)</td>
<td rowspan="1" colspan="1">0.0263 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">−0.3270 (5)</td>
<td rowspan="1" colspan="1">−0.0149 (3)</td>
<td rowspan="1" colspan="1">−0.2585 (4)</td>
<td rowspan="1" colspan="1">0.0581 (10)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19A</td>
<td rowspan="1" colspan="1">−0.3866</td>
<td rowspan="1" colspan="1">−0.0421</td>
<td rowspan="1" colspan="1">−0.3315</td>
<td rowspan="1" colspan="1">0.087*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19B</td>
<td rowspan="1" colspan="1">−0.3950</td>
<td rowspan="1" colspan="1">0.0018</td>
<td rowspan="1" colspan="1">−0.2030</td>
<td rowspan="1" colspan="1">0.087*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19C</td>
<td rowspan="1" colspan="1">−0.2516</td>
<td rowspan="1" colspan="1">−0.0588</td>
<td rowspan="1" colspan="1">−0.2193</td>
<td rowspan="1" colspan="1">0.087*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">−0.3652 (4)</td>
<td rowspan="1" colspan="1">0.1381 (2)</td>
<td rowspan="1" colspan="1">−0.3552 (3)</td>
<td rowspan="1" colspan="1">0.0459 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20A</td>
<td rowspan="1" colspan="1">−0.4216</td>
<td rowspan="1" colspan="1">0.1112</td>
<td rowspan="1" colspan="1">−0.4295</td>
<td rowspan="1" colspan="1">0.069*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20B</td>
<td rowspan="1" colspan="1">−0.3141</td>
<td rowspan="1" colspan="1">0.1936</td>
<td rowspan="1" colspan="1">−0.3748</td>
<td rowspan="1" colspan="1">0.069*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20C</td>
<td rowspan="1" colspan="1">−0.4358</td>
<td rowspan="1" colspan="1">0.1530</td>
<td rowspan="1" colspan="1">−0.3010</td>
<td rowspan="1" colspan="1">0.069*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.2173 (4)</td>
<td rowspan="1" colspan="1">0.0007 (2)</td>
<td rowspan="1" colspan="1">−0.1322 (3)</td>
<td rowspan="1" colspan="1">0.0446 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21A</td>
<td rowspan="1" colspan="1">0.2785</td>
<td rowspan="1" colspan="1">−0.0351</td>
<td rowspan="1" colspan="1">−0.1789</td>
<td rowspan="1" colspan="1">0.067*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21B</td>
<td rowspan="1" colspan="1">0.1593</td>
<td rowspan="1" colspan="1">−0.0401</td>
<td rowspan="1" colspan="1">−0.0890</td>
<td rowspan="1" colspan="1">0.067*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21C</td>
<td rowspan="1" colspan="1">0.2844</td>
<td rowspan="1" colspan="1">0.0388</td>
<td rowspan="1" colspan="1">−0.0739</td>
<td rowspan="1" colspan="1">0.067*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.1982 (4)</td>
<td rowspan="1" colspan="1">0.1307 (2)</td>
<td rowspan="1" colspan="1">−0.2773 (3)</td>
<td rowspan="1" colspan="1">0.0426 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22A</td>
<td rowspan="1" colspan="1">0.2681</td>
<td rowspan="1" colspan="1">0.0986</td>
<td rowspan="1" colspan="1">−0.3203</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22B</td>
<td rowspan="1" colspan="1">0.2564</td>
<td rowspan="1" colspan="1">0.1697</td>
<td rowspan="1" colspan="1">−0.2150</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22C</td>
<td rowspan="1" colspan="1">0.1283</td>
<td rowspan="1" colspan="1">0.1680</td>
<td rowspan="1" colspan="1">−0.3344</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.0575 (3)</td>
<td rowspan="1" colspan="1">0.15834 (16)</td>
<td rowspan="1" colspan="1">−0.0442 (2)</td>
<td rowspan="1" colspan="1">0.0248 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4N</td>
<td rowspan="1" colspan="1">0.153 (9)</td>
<td rowspan="1" colspan="1">0.165 (5)</td>
<td rowspan="1" colspan="1">−0.011 (6)</td>
<td rowspan="1" colspan="1">0.030*</td>
<td rowspan="1" colspan="1">0.50 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">−0.0255 (3)</td>
<td rowspan="1" colspan="1">0.2469 (2)</td>
<td rowspan="1" colspan="1">0.1041 (2)</td>
<td rowspan="1" colspan="1">0.0387 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H5N</td>
<td rowspan="1" colspan="1">−0.096 (4)</td>
<td rowspan="1" colspan="1">0.249 (3)</td>
<td rowspan="1" colspan="1">0.142 (3)</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H6N</td>
<td rowspan="1" colspan="1">0.073 (4)</td>
<td rowspan="1" colspan="1">0.245 (2)</td>
<td rowspan="1" colspan="1">0.147 (3)</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">−0.23122 (8)</td>
<td rowspan="1" colspan="1">0.17442 (5)</td>
<td rowspan="1" colspan="1">−0.07649 (6)</td>
<td rowspan="1" colspan="1">0.02918 (18)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C26</td>
<td rowspan="1" colspan="1">0.3743 (3)</td>
<td rowspan="1" colspan="1">0.22426 (19)</td>
<td rowspan="1" colspan="1">0.1462 (3)</td>
<td rowspan="1" colspan="1">0.0271 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C25</td>
<td rowspan="1" colspan="1">0.5352 (3)</td>
<td rowspan="1" colspan="1">0.2536 (2)</td>
<td rowspan="1" colspan="1">0.1889 (3)</td>
<td rowspan="1" colspan="1">0.0298 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H25A</td>
<td rowspan="1" colspan="1">0.5538</td>
<td rowspan="1" colspan="1">0.3096</td>
<td rowspan="1" colspan="1">0.1451</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H25B</td>
<td rowspan="1" colspan="1">0.6039</td>
<td rowspan="1" colspan="1">0.2060</td>
<td rowspan="1" colspan="1">0.1676</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C24</td>
<td rowspan="1" colspan="1">0.5760 (3)</td>
<td rowspan="1" colspan="1">0.2717 (2)</td>
<td rowspan="1" colspan="1">0.3238 (3)</td>
<td rowspan="1" colspan="1">0.0300 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H24A</td>
<td rowspan="1" colspan="1">0.5202</td>
<td rowspan="1" colspan="1">0.3264</td>
<td rowspan="1" colspan="1">0.3427</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H24B</td>
<td rowspan="1" colspan="1">0.5406</td>
<td rowspan="1" colspan="1">0.2199</td>
<td rowspan="1" colspan="1">0.3672</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C23</td>
<td rowspan="1" colspan="1">0.7441 (3)</td>
<td rowspan="1" colspan="1">0.2859 (2)</td>
<td rowspan="1" colspan="1">0.3709 (3)</td>
<td rowspan="1" colspan="1">0.0284 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.7810 (2)</td>
<td rowspan="1" colspan="1">0.32184 (16)</td>
<td rowspan="1" colspan="1">0.47272 (18)</td>
<td rowspan="1" colspan="1">0.0379 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.8363 (2)</td>
<td rowspan="1" colspan="1">0.2585 (2)</td>
<td rowspan="1" colspan="1">0.3079 (2)</td>
<td rowspan="1" colspan="1">0.0575 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.3395 (3)</td>
<td rowspan="1" colspan="1">0.20074 (16)</td>
<td rowspan="1" colspan="1">0.03486 (19)</td>
<td rowspan="1" colspan="1">0.0388 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1O</td>
<td rowspan="1" colspan="1">0.249 (11)</td>
<td rowspan="1" colspan="1">0.191 (5)</td>
<td rowspan="1" colspan="1">0.008 (7)</td>
<td rowspan="1" colspan="1">0.047*</td>
<td rowspan="1" colspan="1">0.50 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.2832 (2)</td>
<td rowspan="1" colspan="1">0.2213 (2)</td>
<td rowspan="1" colspan="1">0.21545 (19)</td>
<td rowspan="1" colspan="1">0.0500 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e13361" sec-type="tablewrapadps"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e13373"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0280 (14)</td>
<td rowspan="1" colspan="1">0.0258 (13)</td>
<td rowspan="1" colspan="1">0.0253 (14)</td>
<td rowspan="1" colspan="1">0.0017 (11)</td>
<td rowspan="1" colspan="1">0.0051 (11)</td>
<td rowspan="1" colspan="1">−0.0003 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0308 (15)</td>
<td rowspan="1" colspan="1">0.0380 (16)</td>
<td rowspan="1" colspan="1">0.0364 (17)</td>
<td rowspan="1" colspan="1">0.0002 (13)</td>
<td rowspan="1" colspan="1">0.0009 (13)</td>
<td rowspan="1" colspan="1">−0.0095 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0322 (15)</td>
<td rowspan="1" colspan="1">0.0316 (15)</td>
<td rowspan="1" colspan="1">0.0295 (15)</td>
<td rowspan="1" colspan="1">−0.0011 (13)</td>
<td rowspan="1" colspan="1">0.0082 (13)</td>
<td rowspan="1" colspan="1">−0.0073 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0287 (14)</td>
<td rowspan="1" colspan="1">0.0218 (12)</td>
<td rowspan="1" colspan="1">0.0207 (13)</td>
<td rowspan="1" colspan="1">−0.0020 (11)</td>
<td rowspan="1" colspan="1">0.0050 (11)</td>
<td rowspan="1" colspan="1">0.0005 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0236 (14)</td>
<td rowspan="1" colspan="1">0.0331 (15)</td>
<td rowspan="1" colspan="1">0.0223 (14)</td>
<td rowspan="1" colspan="1">0.0018 (11)</td>
<td rowspan="1" colspan="1">0.0032 (11)</td>
<td rowspan="1" colspan="1">0.0001 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.063 (2)</td>
<td rowspan="1" colspan="1">0.059 (2)</td>
<td rowspan="1" colspan="1">0.048 (2)</td>
<td rowspan="1" colspan="1">−0.019 (2)</td>
<td rowspan="1" colspan="1">−0.0263 (19)</td>
<td rowspan="1" colspan="1">0.0101 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.069 (3)</td>
<td rowspan="1" colspan="1">0.047 (2)</td>
<td rowspan="1" colspan="1">0.079 (3)</td>
<td rowspan="1" colspan="1">−0.026 (2)</td>
<td rowspan="1" colspan="1">−0.018 (2)</td>
<td rowspan="1" colspan="1">0.003 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.054 (2)</td>
<td rowspan="1" colspan="1">0.0462 (19)</td>
<td rowspan="1" colspan="1">0.053 (2)</td>
<td rowspan="1" colspan="1">0.0011 (17)</td>
<td rowspan="1" colspan="1">0.0319 (18)</td>
<td rowspan="1" colspan="1">0.0051 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.079 (3)</td>
<td rowspan="1" colspan="1">0.048 (2)</td>
<td rowspan="1" colspan="1">0.088 (3)</td>
<td rowspan="1" colspan="1">0.031 (2)</td>
<td rowspan="1" colspan="1">0.052 (3)</td>
<td rowspan="1" colspan="1">0.023 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0226 (12)</td>
<td rowspan="1" colspan="1">0.0286 (12)</td>
<td rowspan="1" colspan="1">0.0226 (12)</td>
<td rowspan="1" colspan="1">−0.0009 (10)</td>
<td rowspan="1" colspan="1">0.0037 (9)</td>
<td rowspan="1" colspan="1">−0.0015 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.0287 (14)</td>
<td rowspan="1" colspan="1">0.0613 (19)</td>
<td rowspan="1" colspan="1">0.0288 (15)</td>
<td rowspan="1" colspan="1">0.0056 (13)</td>
<td rowspan="1" colspan="1">0.0044 (12)</td>
<td rowspan="1" colspan="1">−0.0156 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0231 (3)</td>
<td rowspan="1" colspan="1">0.0400 (4)</td>
<td rowspan="1" colspan="1">0.0290 (4)</td>
<td rowspan="1" colspan="1">0.0043 (3)</td>
<td rowspan="1" colspan="1">0.0032 (3)</td>
<td rowspan="1" colspan="1">−0.0045 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.0266 (14)</td>
<td rowspan="1" colspan="1">0.0253 (13)</td>
<td rowspan="1" colspan="1">0.0267 (14)</td>
<td rowspan="1" colspan="1">−0.0014 (11)</td>
<td rowspan="1" colspan="1">0.0058 (12)</td>
<td rowspan="1" colspan="1">0.0007 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.0337 (16)</td>
<td rowspan="1" colspan="1">0.0343 (15)</td>
<td rowspan="1" colspan="1">0.0331 (16)</td>
<td rowspan="1" colspan="1">−0.0093 (13)</td>
<td rowspan="1" colspan="1">−0.0005 (13)</td>
<td rowspan="1" colspan="1">−0.0047 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.0425 (18)</td>
<td rowspan="1" colspan="1">0.0461 (18)</td>
<td rowspan="1" colspan="1">0.0305 (16)</td>
<td rowspan="1" colspan="1">−0.0013 (14)</td>
<td rowspan="1" colspan="1">0.0000 (14)</td>
<td rowspan="1" colspan="1">−0.0137 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0437 (18)</td>
<td rowspan="1" colspan="1">0.0420 (17)</td>
<td rowspan="1" colspan="1">0.0408 (18)</td>
<td rowspan="1" colspan="1">0.0018 (15)</td>
<td rowspan="1" colspan="1">0.0044 (15)</td>
<td rowspan="1" colspan="1">−0.0170 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.0303 (14)</td>
<td rowspan="1" colspan="1">0.0295 (14)</td>
<td rowspan="1" colspan="1">0.0287 (15)</td>
<td rowspan="1" colspan="1">0.0027 (12)</td>
<td rowspan="1" colspan="1">0.0052 (12)</td>
<td rowspan="1" colspan="1">−0.0028 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.0276 (14)</td>
<td rowspan="1" colspan="1">0.0231 (12)</td>
<td rowspan="1" colspan="1">0.0225 (14)</td>
<td rowspan="1" colspan="1">−0.0007 (11)</td>
<td rowspan="1" colspan="1">0.0038 (11)</td>
<td rowspan="1" colspan="1">0.0016 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.0262 (14)</td>
<td rowspan="1" colspan="1">0.0297 (15)</td>
<td rowspan="1" colspan="1">0.0225 (14)</td>
<td rowspan="1" colspan="1">0.0023 (11)</td>
<td rowspan="1" colspan="1">0.0032 (12)</td>
<td rowspan="1" colspan="1">0.0017 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.062 (2)</td>
<td rowspan="1" colspan="1">0.048 (2)</td>
<td rowspan="1" colspan="1">0.061 (2)</td>
<td rowspan="1" colspan="1">−0.0282 (18)</td>
<td rowspan="1" colspan="1">0.004 (2)</td>
<td rowspan="1" colspan="1">−0.0068 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">0.0333 (17)</td>
<td rowspan="1" colspan="1">0.060 (2)</td>
<td rowspan="1" colspan="1">0.0387 (19)</td>
<td rowspan="1" colspan="1">0.0004 (16)</td>
<td rowspan="1" colspan="1">−0.0078 (14)</td>
<td rowspan="1" colspan="1">−0.0049 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.0418 (18)</td>
<td rowspan="1" colspan="1">0.0429 (18)</td>
<td rowspan="1" colspan="1">0.0472 (19)</td>
<td rowspan="1" colspan="1">0.0173 (15)</td>
<td rowspan="1" colspan="1">0.0028 (16)</td>
<td rowspan="1" colspan="1">−0.0068 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.0396 (18)</td>
<td rowspan="1" colspan="1">0.0499 (19)</td>
<td rowspan="1" colspan="1">0.0433 (19)</td>
<td rowspan="1" colspan="1">−0.0023 (15)</td>
<td rowspan="1" colspan="1">0.0206 (16)</td>
<td rowspan="1" colspan="1">−0.0042 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.0218 (11)</td>
<td rowspan="1" colspan="1">0.0306 (13)</td>
<td rowspan="1" colspan="1">0.0210 (12)</td>
<td rowspan="1" colspan="1">0.0003 (10)</td>
<td rowspan="1" colspan="1">0.0015 (9)</td>
<td rowspan="1" colspan="1">−0.0004 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.0286 (14)</td>
<td rowspan="1" colspan="1">0.0594 (17)</td>
<td rowspan="1" colspan="1">0.0277 (15)</td>
<td rowspan="1" colspan="1">0.0047 (13)</td>
<td rowspan="1" colspan="1">0.0038 (12)</td>
<td rowspan="1" colspan="1">−0.0121 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">0.0230 (3)</td>
<td rowspan="1" colspan="1">0.0361 (4)</td>
<td rowspan="1" colspan="1">0.0287 (4)</td>
<td rowspan="1" colspan="1">0.0008 (3)</td>
<td rowspan="1" colspan="1">0.0053 (3)</td>
<td rowspan="1" colspan="1">0.0016 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C26</td>
<td rowspan="1" colspan="1">0.0268 (14)</td>
<td rowspan="1" colspan="1">0.0289 (14)</td>
<td rowspan="1" colspan="1">0.0248 (14)</td>
<td rowspan="1" colspan="1">0.0020 (12)</td>
<td rowspan="1" colspan="1">0.0021 (12)</td>
<td rowspan="1" colspan="1">−0.0022 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C25</td>
<td rowspan="1" colspan="1">0.0281 (15)</td>
<td rowspan="1" colspan="1">0.0363 (15)</td>
<td rowspan="1" colspan="1">0.0243 (15)</td>
<td rowspan="1" colspan="1">−0.0015 (12)</td>
<td rowspan="1" colspan="1">0.0031 (12)</td>
<td rowspan="1" colspan="1">−0.0019 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C24</td>
<td rowspan="1" colspan="1">0.0250 (14)</td>
<td rowspan="1" colspan="1">0.0386 (16)</td>
<td rowspan="1" colspan="1">0.0256 (15)</td>
<td rowspan="1" colspan="1">0.0016 (12)</td>
<td rowspan="1" colspan="1">0.0025 (12)</td>
<td rowspan="1" colspan="1">−0.0064 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C23</td>
<td rowspan="1" colspan="1">0.0279 (15)</td>
<td rowspan="1" colspan="1">0.0321 (14)</td>
<td rowspan="1" colspan="1">0.0251 (15)</td>
<td rowspan="1" colspan="1">−0.0012 (12)</td>
<td rowspan="1" colspan="1">0.0045 (12)</td>
<td rowspan="1" colspan="1">−0.0019 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0275 (10)</td>
<td rowspan="1" colspan="1">0.0581 (14)</td>
<td rowspan="1" colspan="1">0.0274 (11)</td>
<td rowspan="1" colspan="1">−0.0050 (10)</td>
<td rowspan="1" colspan="1">0.0029 (8)</td>
<td rowspan="1" colspan="1">−0.0178 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0259 (12)</td>
<td rowspan="1" colspan="1">0.109 (2)</td>
<td rowspan="1" colspan="1">0.0368 (13)</td>
<td rowspan="1" colspan="1">−0.0003 (13)</td>
<td rowspan="1" colspan="1">0.0035 (10)</td>
<td rowspan="1" colspan="1">−0.0313 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.0263 (11)</td>
<td rowspan="1" colspan="1">0.0618 (16)</td>
<td rowspan="1" colspan="1">0.0273 (12)</td>
<td rowspan="1" colspan="1">−0.0077 (10)</td>
<td rowspan="1" colspan="1">0.0022 (9)</td>
<td rowspan="1" colspan="1">−0.0105 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.0280 (11)</td>
<td rowspan="1" colspan="1">0.0919 (19)</td>
<td rowspan="1" colspan="1">0.0312 (12)</td>
<td rowspan="1" colspan="1">−0.0076 (12)</td>
<td rowspan="1" colspan="1">0.0084 (10)</td>
<td rowspan="1" colspan="1">−0.0186 (13)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e14010" sec-type="tablewrapgeomlong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e14020"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.349 (4)</td>
<td rowspan="1" colspan="1">C13—C19</td>
<td rowspan="1" colspan="1">1.530 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.506 (4)</td>
<td rowspan="1" colspan="1">C13—C20</td>
<td rowspan="1" colspan="1">1.538 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—S1</td>
<td rowspan="1" colspan="1">1.754 (3)</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.538 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8</td>
<td rowspan="1" colspan="1">1.515 (5)</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.528 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9</td>
<td rowspan="1" colspan="1">1.531 (5)</td>
<td rowspan="1" colspan="1">C14—H14A</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A</td>
<td rowspan="1" colspan="1">1.537 (6)</td>
<td rowspan="1" colspan="1">C14—H14B</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B</td>
<td rowspan="1" colspan="1">1.589 (10)</td>
<td rowspan="1" colspan="1">C15—C16</td>
<td rowspan="1" colspan="1">1.536 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A</td>
<td rowspan="1" colspan="1">1.544 (9)</td>
<td rowspan="1" colspan="1">C15—H15A</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—H3A1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C15—H15B</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—H3A2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.512 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5</td>
<td rowspan="1" colspan="1">1.581 (6)</td>
<td rowspan="1" colspan="1">C16—C22</td>
<td rowspan="1" colspan="1">1.532 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H4A1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C16—C21</td>
<td rowspan="1" colspan="1">1.536 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H4A2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C17—N3</td>
<td rowspan="1" colspan="1">1.395 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B</td>
<td rowspan="1" colspan="1">1.499 (14)</td>
<td rowspan="1" colspan="1">C18—N3</td>
<td rowspan="1" colspan="1">1.321 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—H3B1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C18—N4</td>
<td rowspan="1" colspan="1">1.337 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—H3B2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C18—S2</td>
<td rowspan="1" colspan="1">1.728 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5</td>
<td rowspan="1" colspan="1">1.519 (8)</td>
<td rowspan="1" colspan="1">C19—H19A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H4B1</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C19—H19B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H4B2</td>
<td rowspan="1" colspan="1">0.9900</td>
<td rowspan="1" colspan="1">C19—H19C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.502 (4)</td>
<td rowspan="1" colspan="1">C20—H20A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10</td>
<td rowspan="1" colspan="1">1.520 (4)</td>
<td rowspan="1" colspan="1">C20—H20B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11</td>
<td rowspan="1" colspan="1">1.525 (5)</td>
<td rowspan="1" colspan="1">C20—H20C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1</td>
<td rowspan="1" colspan="1">1.394 (3)</td>
<td rowspan="1" colspan="1">C21—H21A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2</td>
<td rowspan="1" colspan="1">1.319 (4)</td>
<td rowspan="1" colspan="1">C21—H21B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1</td>
<td rowspan="1" colspan="1">1.325 (3)</td>
<td rowspan="1" colspan="1">C21—H21C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—S1</td>
<td rowspan="1" colspan="1">1.726 (3)</td>
<td rowspan="1" colspan="1">C22—H22A</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C22—H22B</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C22—H22C</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—H8C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N3—H4N</td>
<td rowspan="1" colspan="1">0.87 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N4—H5N</td>
<td rowspan="1" colspan="1">0.82 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">N4—H6N</td>
<td rowspan="1" colspan="1">0.92 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C26—O4</td>
<td rowspan="1" colspan="1">1.228 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C26—O3</td>
<td rowspan="1" colspan="1">1.283 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C26—C25</td>
<td rowspan="1" colspan="1">1.496 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—H10C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C25—C24</td>
<td rowspan="1" colspan="1">1.521 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C25—H25A</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11B</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C25—H25B</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11C</td>
<td rowspan="1" colspan="1">0.9800</td>
<td rowspan="1" colspan="1">C24—C23</td>
<td rowspan="1" colspan="1">1.515 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1N</td>
<td rowspan="1" colspan="1">0.93 (3)</td>
<td rowspan="1" colspan="1">C24—H24A</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2N</td>
<td rowspan="1" colspan="1">0.89 (4)</td>
<td rowspan="1" colspan="1">C24—H24B</td>
<td rowspan="1" colspan="1">0.9900</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3N</td>
<td rowspan="1" colspan="1">0.82 (4)</td>
<td rowspan="1" colspan="1">C23—O2</td>
<td rowspan="1" colspan="1">1.249 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12—C17</td>
<td rowspan="1" colspan="1">1.348 (4)</td>
<td rowspan="1" colspan="1">C23—O1</td>
<td rowspan="1" colspan="1">1.252 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.503 (4)</td>
<td rowspan="1" colspan="1">O3—H1O</td>
<td rowspan="1" colspan="1">0.82 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12—S2</td>
<td rowspan="1" colspan="1">1.753 (3)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2</td>
<td rowspan="1" colspan="1">127.6 (3)</td>
<td rowspan="1" colspan="1">C17—C12—S2</td>
<td rowspan="1" colspan="1">109.8 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—S1</td>
<td rowspan="1" colspan="1">110.5 (2)</td>
<td rowspan="1" colspan="1">C13—C12—S2</td>
<td rowspan="1" colspan="1">123.0 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—S1</td>
<td rowspan="1" colspan="1">122.0 (2)</td>
<td rowspan="1" colspan="1">C12—C13—C19</td>
<td rowspan="1" colspan="1">110.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C8</td>
<td rowspan="1" colspan="1">110.5 (3)</td>
<td rowspan="1" colspan="1">C12—C13—C20</td>
<td rowspan="1" colspan="1">110.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C9</td>
<td rowspan="1" colspan="1">109.6 (3)</td>
<td rowspan="1" colspan="1">C19—C13—C20</td>
<td rowspan="1" colspan="1">109.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C9</td>
<td rowspan="1" colspan="1">107.7 (3)</td>
<td rowspan="1" colspan="1">C12—C13—C14</td>
<td rowspan="1" colspan="1">106.4 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3A</td>
<td rowspan="1" colspan="1">106.1 (3)</td>
<td rowspan="1" colspan="1">C19—C13—C14</td>
<td rowspan="1" colspan="1">111.6 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3A</td>
<td rowspan="1" colspan="1">120.8 (4)</td>
<td rowspan="1" colspan="1">C20—C13—C14</td>
<td rowspan="1" colspan="1">109.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3A</td>
<td rowspan="1" colspan="1">101.6 (4)</td>
<td rowspan="1" colspan="1">C15—C14—C13</td>
<td rowspan="1" colspan="1">112.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3B</td>
<td rowspan="1" colspan="1">104.4 (4)</td>
<td rowspan="1" colspan="1">C15—C14—H14A</td>
<td rowspan="1" colspan="1">109.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3B</td>
<td rowspan="1" colspan="1">94.5 (5)</td>
<td rowspan="1" colspan="1">C13—C14—H14A</td>
<td rowspan="1" colspan="1">109.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3B</td>
<td rowspan="1" colspan="1">128.7 (5)</td>
<td rowspan="1" colspan="1">C15—C14—H14B</td>
<td rowspan="1" colspan="1">109.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—C4A</td>
<td rowspan="1" colspan="1">110.5 (5)</td>
<td rowspan="1" colspan="1">C13—C14—H14B</td>
<td rowspan="1" colspan="1">109.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—H3A1</td>
<td rowspan="1" colspan="1">109.6</td>
<td rowspan="1" colspan="1">H14A—C14—H14B</td>
<td rowspan="1" colspan="1">107.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—H3A1</td>
<td rowspan="1" colspan="1">109.6</td>
<td rowspan="1" colspan="1">C14—C15—C16</td>
<td rowspan="1" colspan="1">113.7 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—H3A2</td>
<td rowspan="1" colspan="1">109.6</td>
<td rowspan="1" colspan="1">C14—C15—H15A</td>
<td rowspan="1" colspan="1">108.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C3A—H3A2</td>
<td rowspan="1" colspan="1">109.6</td>
<td rowspan="1" colspan="1">C16—C15—H15A</td>
<td rowspan="1" colspan="1">108.8</td>
</tr>
<tr><td rowspan="1" colspan="1">H3A1—C3A—H3A2</td>
<td rowspan="1" colspan="1">108.1</td>
<td rowspan="1" colspan="1">C14—C15—H15B</td>
<td rowspan="1" colspan="1">108.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5</td>
<td rowspan="1" colspan="1">110.5 (5)</td>
<td rowspan="1" colspan="1">C16—C15—H15B</td>
<td rowspan="1" colspan="1">108.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—H4A1</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H15A—C15—H15B</td>
<td rowspan="1" colspan="1">107.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4A—H4A1</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C17—C16—C22</td>
<td rowspan="1" colspan="1">109.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—H4A2</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C17—C16—C21</td>
<td rowspan="1" colspan="1">110.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4A—H4A2</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C22—C16—C21</td>
<td rowspan="1" colspan="1">109.3 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">H4A1—C4A—H4A2</td>
<td rowspan="1" colspan="1">108.1</td>
<td rowspan="1" colspan="1">C17—C16—C15</td>
<td rowspan="1" colspan="1">107.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—C2</td>
<td rowspan="1" colspan="1">113.6 (8)</td>
<td rowspan="1" colspan="1">C22—C16—C15</td>
<td rowspan="1" colspan="1">111.0 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—H3B1</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C21—C16—C15</td>
<td rowspan="1" colspan="1">108.7 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—H3B1</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C12—C17—N3</td>
<td rowspan="1" colspan="1">114.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C3B—H3B2</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">C12—C17—C16</td>
<td rowspan="1" colspan="1">124.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—H3B2</td>
<td rowspan="1" colspan="1">108.8</td>
<td rowspan="1" colspan="1">N3—C17—C16</td>
<td rowspan="1" colspan="1">120.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H3B1—C3B—H3B2</td>
<td rowspan="1" colspan="1">107.7</td>
<td rowspan="1" colspan="1">N3—C18—N4</td>
<td rowspan="1" colspan="1">123.8 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5</td>
<td rowspan="1" colspan="1">114.1 (8)</td>
<td rowspan="1" colspan="1">N3—C18—S2</td>
<td rowspan="1" colspan="1">113.0 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—H4B1</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">N4—C18—S2</td>
<td rowspan="1" colspan="1">123.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—H4B1</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C13—C19—H19A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—H4B2</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C13—C19—H19B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4B—H4B2</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">H19A—C19—H19B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H4B1—C4B—H4B2</td>
<td rowspan="1" colspan="1">107.6</td>
<td rowspan="1" colspan="1">C13—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4B</td>
<td rowspan="1" colspan="1">109.0 (4)</td>
<td rowspan="1" colspan="1">H19A—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C10</td>
<td rowspan="1" colspan="1">110.2 (2)</td>
<td rowspan="1" colspan="1">H19B—C19—H19C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C10</td>
<td rowspan="1" colspan="1">122.0 (4)</td>
<td rowspan="1" colspan="1">C13—C20—H20A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C11</td>
<td rowspan="1" colspan="1">110.4 (3)</td>
<td rowspan="1" colspan="1">C13—C20—H20B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C11</td>
<td rowspan="1" colspan="1">95.9 (5)</td>
<td rowspan="1" colspan="1">H20A—C20—H20B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C11</td>
<td rowspan="1" colspan="1">108.3 (3)</td>
<td rowspan="1" colspan="1">C13—C20—H20C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4A</td>
<td rowspan="1" colspan="1">105.6 (3)</td>
<td rowspan="1" colspan="1">H20A—C20—H20C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C4A</td>
<td rowspan="1" colspan="1">101.6 (3)</td>
<td rowspan="1" colspan="1">H20B—C20—H20C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C4A</td>
<td rowspan="1" colspan="1">120.2 (4)</td>
<td rowspan="1" colspan="1">C16—C21—H21A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1</td>
<td rowspan="1" colspan="1">113.4 (2)</td>
<td rowspan="1" colspan="1">C16—C21—H21B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—C5</td>
<td rowspan="1" colspan="1">124.8 (3)</td>
<td rowspan="1" colspan="1">H21A—C21—H21B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C6—C5</td>
<td rowspan="1" colspan="1">121.7 (2)</td>
<td rowspan="1" colspan="1">C16—C21—H21C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1</td>
<td rowspan="1" colspan="1">124.0 (3)</td>
<td rowspan="1" colspan="1">H21A—C21—H21C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1</td>
<td rowspan="1" colspan="1">123.7 (2)</td>
<td rowspan="1" colspan="1">H21B—C21—H21C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C7—S1</td>
<td rowspan="1" colspan="1">112.3 (2)</td>
<td rowspan="1" colspan="1">C16—C22—H22A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C22—H22B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H22A—C22—H22B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C16—C22—H22C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H22A—C22—H22C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8A—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H22B—C22—H22C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H8B—C8—H8C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N3—C17</td>
<td rowspan="1" colspan="1">112.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N3—H4N</td>
<td rowspan="1" colspan="1">121 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C17—N3—H4N</td>
<td rowspan="1" colspan="1">127 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N4—H5N</td>
<td rowspan="1" colspan="1">115 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—N4—H6N</td>
<td rowspan="1" colspan="1">115 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9A—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H5N—N4—H6N</td>
<td rowspan="1" colspan="1">118 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">H9B—C9—H9C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C18—S2—C12</td>
<td rowspan="1" colspan="1">90.03 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O4—C26—O3</td>
<td rowspan="1" colspan="1">122.7 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O4—C26—C25</td>
<td rowspan="1" colspan="1">121.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">H10A—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">O3—C26—C25</td>
<td rowspan="1" colspan="1">116.1 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C26—C25—C24</td>
<td rowspan="1" colspan="1">114.4 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H10A—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C26—C25—H25A</td>
<td rowspan="1" colspan="1">108.7</td>
</tr>
<tr><td rowspan="1" colspan="1">H10B—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C24—C25—H25A</td>
<td rowspan="1" colspan="1">108.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11—H11A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C26—C25—H25B</td>
<td rowspan="1" colspan="1">108.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C24—C25—H25B</td>
<td rowspan="1" colspan="1">108.7</td>
</tr>
<tr><td rowspan="1" colspan="1">H11A—C11—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H25A—C25—H25B</td>
<td rowspan="1" colspan="1">107.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C23—C24—C25</td>
<td rowspan="1" colspan="1">114.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H11A—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C23—C24—H24A</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">H11B—C11—H11C</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C25—C24—H24A</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1—C6</td>
<td rowspan="1" colspan="1">113.7 (2)</td>
<td rowspan="1" colspan="1">C23—C24—H24B</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N1—H1N</td>
<td rowspan="1" colspan="1">118.6 (18)</td>
<td rowspan="1" colspan="1">C25—C24—H24B</td>
<td rowspan="1" colspan="1">108.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1—H1N</td>
<td rowspan="1" colspan="1">127.6 (18)</td>
<td rowspan="1" colspan="1">H24A—C24—H24B</td>
<td rowspan="1" colspan="1">107.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2—H2N</td>
<td rowspan="1" colspan="1">120 (2)</td>
<td rowspan="1" colspan="1">O2—C23—O1</td>
<td rowspan="1" colspan="1">124.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—N2—H3N</td>
<td rowspan="1" colspan="1">117 (3)</td>
<td rowspan="1" colspan="1">O2—C23—C24</td>
<td rowspan="1" colspan="1">118.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">H2N—N2—H3N</td>
<td rowspan="1" colspan="1">121 (4)</td>
<td rowspan="1" colspan="1">O1—C23—C24</td>
<td rowspan="1" colspan="1">117.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—S1—C1</td>
<td rowspan="1" colspan="1">90.11 (13)</td>
<td rowspan="1" colspan="1">C26—O3—H1O</td>
<td rowspan="1" colspan="1">117 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17—C12—C13</td>
<td rowspan="1" colspan="1">127.2 (3)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C8</td>
<td rowspan="1" colspan="1">117.8 (4)</td>
<td rowspan="1" colspan="1">N1—C7—S1—C1</td>
<td rowspan="1" colspan="1">0.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C8</td>
<td rowspan="1" colspan="1">−61.8 (3)</td>
<td rowspan="1" colspan="1">C6—C1—S1—C7</td>
<td rowspan="1" colspan="1">0.1 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C9</td>
<td rowspan="1" colspan="1">−123.7 (3)</td>
<td rowspan="1" colspan="1">C2—C1—S1—C7</td>
<td rowspan="1" colspan="1">179.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C9</td>
<td rowspan="1" colspan="1">56.7 (3)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C19</td>
<td rowspan="1" colspan="1">105.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C3A</td>
<td rowspan="1" colspan="1">−14.8 (5)</td>
<td rowspan="1" colspan="1">S2—C12—C13—C19</td>
<td rowspan="1" colspan="1">−74.9 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C3A</td>
<td rowspan="1" colspan="1">165.7 (3)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C20</td>
<td rowspan="1" colspan="1">−133.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C3B</td>
<td rowspan="1" colspan="1">17.2 (6)</td>
<td rowspan="1" colspan="1">S2—C12—C13—C20</td>
<td rowspan="1" colspan="1">45.7 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C2—C3B</td>
<td rowspan="1" colspan="1">−162.3 (5)</td>
<td rowspan="1" colspan="1">C17—C12—C13—C14</td>
<td rowspan="1" colspan="1">−15.3 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3A—C4A</td>
<td rowspan="1" colspan="1">47.7 (6)</td>
<td rowspan="1" colspan="1">S2—C12—C13—C14</td>
<td rowspan="1" colspan="1">163.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3A—C4A</td>
<td rowspan="1" colspan="1">−78.9 (5)</td>
<td rowspan="1" colspan="1">C12—C13—C14—C15</td>
<td rowspan="1" colspan="1">45.6 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3A—C4A</td>
<td rowspan="1" colspan="1">162.2 (5)</td>
<td rowspan="1" colspan="1">C19—C13—C14—C15</td>
<td rowspan="1" colspan="1">−74.9 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3A—C4A—C5</td>
<td rowspan="1" colspan="1">−70.2 (6)</td>
<td rowspan="1" colspan="1">C20—C13—C14—C15</td>
<td rowspan="1" colspan="1">164.5 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3B—C4B</td>
<td rowspan="1" colspan="1">−46.1 (9)</td>
<td rowspan="1" colspan="1">C13—C14—C15—C16</td>
<td rowspan="1" colspan="1">−63.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C2—C3B—C4B</td>
<td rowspan="1" colspan="1">−158.7 (8)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C17</td>
<td rowspan="1" colspan="1">42.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C2—C3B—C4B</td>
<td rowspan="1" colspan="1">84.4 (9)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C22</td>
<td rowspan="1" colspan="1">−78.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3B—C4B—C5</td>
<td rowspan="1" colspan="1">62.4 (12)</td>
<td rowspan="1" colspan="1">C14—C15—C16—C21</td>
<td rowspan="1" colspan="1">161.6 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5—C6</td>
<td rowspan="1" colspan="1">−40.4 (10)</td>
<td rowspan="1" colspan="1">C13—C12—C17—N3</td>
<td rowspan="1" colspan="1">177.9 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5—C10</td>
<td rowspan="1" colspan="1">89.8 (8)</td>
<td rowspan="1" colspan="1">S2—C12—C17—N3</td>
<td rowspan="1" colspan="1">−1.4 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B—C4B—C5—C11</td>
<td rowspan="1" colspan="1">−154.4 (8)</td>
<td rowspan="1" colspan="1">C13—C12—C17—C16</td>
<td rowspan="1" colspan="1">−1.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5—C6</td>
<td rowspan="1" colspan="1">49.7 (6)</td>
<td rowspan="1" colspan="1">S2—C12—C17—C16</td>
<td rowspan="1" colspan="1">178.8 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5—C10</td>
<td rowspan="1" colspan="1">164.7 (5)</td>
<td rowspan="1" colspan="1">C22—C16—C17—C12</td>
<td rowspan="1" colspan="1">110.0 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—C4A—C5—C11</td>
<td rowspan="1" colspan="1">−75.9 (5)</td>
<td rowspan="1" colspan="1">C21—C16—C17—C12</td>
<td rowspan="1" colspan="1">−129.4 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—N1</td>
<td rowspan="1" colspan="1">−179.9 (3)</td>
<td rowspan="1" colspan="1">C15—C16—C17—C12</td>
<td rowspan="1" colspan="1">−11.0 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C6—N1</td>
<td rowspan="1" colspan="1">−0.4 (3)</td>
<td rowspan="1" colspan="1">C22—C16—C17—N3</td>
<td rowspan="1" colspan="1">−69.8 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td>
<td rowspan="1" colspan="1">−0.4 (5)</td>
<td rowspan="1" colspan="1">C21—C16—C17—N3</td>
<td rowspan="1" colspan="1">50.8 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1—C6—C5</td>
<td rowspan="1" colspan="1">179.2 (2)</td>
<td rowspan="1" colspan="1">C15—C16—C17—N3</td>
<td rowspan="1" colspan="1">169.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C6—C1</td>
<td rowspan="1" colspan="1">10.6 (6)</td>
<td rowspan="1" colspan="1">N4—C18—N3—C17</td>
<td rowspan="1" colspan="1">−177.9 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C6—C1</td>
<td rowspan="1" colspan="1">−125.7 (3)</td>
<td rowspan="1" colspan="1">S2—C18—N3—C17</td>
<td rowspan="1" colspan="1">−0.6 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C6—C1</td>
<td rowspan="1" colspan="1">114.7 (3)</td>
<td rowspan="1" colspan="1">C12—C17—N3—C18</td>
<td rowspan="1" colspan="1">1.3 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5—C6—C1</td>
<td rowspan="1" colspan="1">−16.8 (4)</td>
<td rowspan="1" colspan="1">C16—C17—N3—C18</td>
<td rowspan="1" colspan="1">−178.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—C5—C6—N1</td>
<td rowspan="1" colspan="1">−169.9 (5)</td>
<td rowspan="1" colspan="1">N3—C18—S2—C12</td>
<td rowspan="1" colspan="1">−0.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C5—C6—N1</td>
<td rowspan="1" colspan="1">53.8 (4)</td>
<td rowspan="1" colspan="1">N4—C18—S2—C12</td>
<td rowspan="1" colspan="1">177.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C5—C6—N1</td>
<td rowspan="1" colspan="1">−65.8 (4)</td>
<td rowspan="1" colspan="1">C17—C12—S2—C18</td>
<td rowspan="1" colspan="1">0.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—C5—C6—N1</td>
<td rowspan="1" colspan="1">162.8 (4)</td>
<td rowspan="1" colspan="1">C13—C12—S2—C18</td>
<td rowspan="1" colspan="1">−178.4 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—N1—C6</td>
<td rowspan="1" colspan="1">178.3 (3)</td>
<td rowspan="1" colspan="1">O4—C26—C25—C24</td>
<td rowspan="1" colspan="1">4.3 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C7—N1—C6</td>
<td rowspan="1" colspan="1">−0.5 (3)</td>
<td rowspan="1" colspan="1">O3—C26—C25—C24</td>
<td rowspan="1" colspan="1">−174.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—N1—C7</td>
<td rowspan="1" colspan="1">0.6 (3)</td>
<td rowspan="1" colspan="1">C26—C25—C24—C23</td>
<td rowspan="1" colspan="1">170.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—N1—C7</td>
<td rowspan="1" colspan="1">−179.0 (2)</td>
<td rowspan="1" colspan="1">C25—C24—C23—O2</td>
<td rowspan="1" colspan="1">−18.9 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C7—S1—C1</td>
<td rowspan="1" colspan="1">−178.5 (3)</td>
<td rowspan="1" colspan="1">C25—C24—C23—O1</td>
<td rowspan="1" colspan="1">163.5 (3)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e15620" sec-type="tablewraphbondslong"><label>Bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium)
succinate–2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate
4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (1/1) (V) </label>
<title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e15629"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H</td>
<td rowspan="1" colspan="1">H···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
···<italic>A</italic>
</td>
<td rowspan="1" colspan="1"><italic>D</italic>
—H···<italic>A</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1<italic>N</italic>
···O1</td>
<td rowspan="1" colspan="1">0.93 (3)</td>
<td rowspan="1" colspan="1">1.70 (3)</td>
<td rowspan="1" colspan="1">2.632 (3)</td>
<td rowspan="1" colspan="1">175 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H2<italic>N</italic>
···O4<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.89 (4)</td>
<td rowspan="1" colspan="1">1.98 (4)</td>
<td rowspan="1" colspan="1">2.779 (3)</td>
<td rowspan="1" colspan="1">149 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—H3<italic>N</italic>
···O2</td>
<td rowspan="1" colspan="1">0.82 (4)</td>
<td rowspan="1" colspan="1">1.89 (4)</td>
<td rowspan="1" colspan="1">2.716 (4)</td>
<td rowspan="1" colspan="1">176 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3—H4<italic>N</italic>
···O3</td>
<td rowspan="1" colspan="1">0.87 (8)</td>
<td rowspan="1" colspan="1">1.73 (8)</td>
<td rowspan="1" colspan="1">2.594 (3)</td>
<td rowspan="1" colspan="1">166 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4—H5<italic>N</italic>
···O2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.82 (4)</td>
<td rowspan="1" colspan="1">2.07 (4)</td>
<td rowspan="1" colspan="1">2.804 (4)</td>
<td rowspan="1" colspan="1">148 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4—H6<italic>N</italic>
···O4</td>
<td rowspan="1" colspan="1">0.92 (4)</td>
<td rowspan="1" colspan="1">1.93 (4)</td>
<td rowspan="1" colspan="1">2.842 (4)</td>
<td rowspan="1" colspan="1">169 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—H1<italic>O</italic>
···N3</td>
<td rowspan="1" colspan="1">0.82 (10)</td>
<td rowspan="1" colspan="1">1.78 (10)</td>
<td rowspan="1" colspan="1">2.594 (3)</td>
<td rowspan="1" colspan="1">174 (8)</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) <italic>x</italic>
+1, <italic>y</italic>
, <italic>z</italic>
; (ii) <italic>x</italic>
−1, <italic>y</italic>
, <italic>z</italic>
.</p>
</sec>
</app>
</app-group>
<ref-list><title>References</title>
<ref id="bb1"><mixed-citation publication-type="other">Biliškov, N., Kojić-Prodić, B., Mali, G., Molčanov, K. & Stare, J. (2011). <italic>J. Phys. Chem. A</italic>
, <bold>115</bold>
, 3154–3166.</mixed-citation>
</ref>
<ref id="bb2"><mixed-citation publication-type="other">Caprathe, B. W., Jaen, J. C., Wise, L. D., Heffner, T. G., Pugsley, T. A., Meltzer, L. T. & Parvez, M. (1991). <italic>J. Med. Chem.</italic>
<bold>34</bold>
, 2736–2746.</mixed-citation>
</ref>
<ref id="bb3"><mixed-citation publication-type="other">Dadmal, T. L., Katre, S. D., Mandewale, M. C. & Kumbhare, R. M. (2018). <italic>New J. Chem.</italic>
<bold>42</bold>
, 776–797.</mixed-citation>
</ref>
<ref id="bb4"><mixed-citation publication-type="other">Fábry, J. (2018). <italic>Acta Cryst.</italic>
 E<bold>74</bold>
, 1344–1357.</mixed-citation>
</ref>
<ref id="bb5"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic>
<bold>45</bold>
, 849–854.</mixed-citation>
</ref>
<ref id="bb6"><mixed-citation publication-type="other">Gao, E., Liu, L., Zhu, M., Huang, Y., Guan, F., Gao, X., Zhang, M., Wang, L., Zhang, W. & Sun, Y. (2011). <italic>Inorg. Chem.</italic>
<bold>50</bold>
, 4732–4741.</mixed-citation>
</ref>
<ref id="bb7"><mixed-citation publication-type="other">Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). <italic>Acta Cryst.</italic>
 B<bold>72</bold>
, 171–179.</mixed-citation>
</ref>
<ref id="bb8"><mixed-citation publication-type="other">Jover, J., Bosque, R. & Sales, J. (2008). <italic>QSAR Comb. Sci.</italic>
<bold>27</bold>
, 563–581.</mixed-citation>
</ref>
<ref id="bb9"><mixed-citation publication-type="other">Kuwar, A., Tayade, K., Keshav, K., Sahoo, S. K., Mayank & Singh, N. (2018). <italic>Supramol. Chem.</italic>
<bold>30</bold>
, 52–60.</mixed-citation>
</ref>
<ref id="bb10"><mixed-citation publication-type="other">Ma, W.-X., Qian, B.-H. & Ge, H.-Y. (2012). <italic>Asian J. Chem.</italic>
<bold>24</bold>
, 3504–3506.</mixed-citation>
</ref>
<ref id="bb11"><mixed-citation publication-type="other">McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). <italic>Chem. Commun.</italic>
 3814–3816.</mixed-citation>
</ref>
<ref id="bb12"><mixed-citation publication-type="other">Noohinejad, L., Mondal, S., Ali, S. I., Dey, S., van Smaalen, S. & Schönleber, A. (2015). <italic>Acta Cryst.</italic>
 B<bold>71</bold>
, 228–234.</mixed-citation>
</ref>
<ref id="bb13"><mixed-citation publication-type="other">Parsons, S., Flack, H. D. & Wagner, T. (2013). <italic>Acta Cryst.</italic>
 B<bold>69</bold>
, 249–259.</mixed-citation>
</ref>
<ref id="bb14"><mixed-citation publication-type="other">Rigaku (2017). <italic>CrystalClear</italic>
 and <italic>CrysAlis PRO</italic>
. Rigaku Corporation, Tokyo, Japan.</mixed-citation>
</ref>
<ref id="bb15"><mixed-citation publication-type="other">Roy, M.-A., Doiron, M., Talon-Croteau, J., Dupré, N. & Simard, M. (2018). <italic>Can. J. Neurol. Sci.</italic>
<bold>45</bold>
, 375–404.</mixed-citation>
</ref>
<ref id="bb16"><mixed-citation publication-type="other">Sagar, B. K., Girisha, M., Yathirajan, H. S., Rathore, R. S. & Glidewell, C. (2017). <italic>Acta Cryst.</italic>
 E<bold>73</bold>
, 1320–1325.</mixed-citation>
</ref>
<ref id="bb17"><mixed-citation publication-type="other">Schneider, C. S. & Mierau, J. (1987). <italic>J. Med. Chem.</italic>
<bold>30</bold>
, 494–498.</mixed-citation>
</ref>
<ref id="bb18"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic>
 A<bold>64</bold>
, 112–122.</mixed-citation>
</ref>
<ref id="bb19"><mixed-citation publication-type="other">Sheldrick, G. M. (2015). <italic>Acta Cryst.</italic>
 C<bold>71</bold>
, 3–8.</mixed-citation>
</ref>
<ref id="bb20"><mixed-citation publication-type="other">Sweeney, J. B., Rattray, M., Pugh, V. & Powell, L. A. (2018). <italic>ACS Med. Chem. Lett.</italic>
<bold>9</bold>
, 552–556.</mixed-citation>
</ref>
<ref id="bb21"><mixed-citation publication-type="other">Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). <italic>CrystalExplorer17</italic>
. University of Western Australia, Nedlands, Australia; http://hirshfeldsurface.net.</mixed-citation>
</ref>
<ref id="bb22"><mixed-citation publication-type="other">Westrip, S. P. (2010). <italic>J. Appl. Cryst.</italic>
<bold>43</bold>
, 920–925.</mixed-citation>
</ref>
<ref id="bb23"><mixed-citation publication-type="other">Zhu, G.-Z., Lu, Z.-S., Lu, H. & Wang, X.-S. (2012). <italic>Z. Krist. New Cryst. Struct.</italic>
<bold>227</bold>
, 525–526.</mixed-citation>
</ref>
</ref-list>
</back>
<floats-group><fig id="fig1" orientation="portrait" position="float"><label>Figure 1</label>
<caption><p>The molecular structure of (I)<xref ref-type="chem" rid="scheme1"></xref>
 showing the major disorder component only of the cation (50% displacement ellipsoids) with the hydrogen bonds indicated by double-dashed lines.</p>
</caption>
<graphic xlink:href="e-75-00167-fig1"></graphic>
</fig>
<fig id="fig2" orientation="portrait" position="float"><label>Figure 2</label>
<caption><p>The molecular structure of (II)<xref ref-type="chem" rid="scheme1"></xref>
 showing 50% displacement ellipsoids with the hydrogen bonds indicated by double-dashed lines.</p>
</caption>
<graphic xlink:href="e-75-00167-fig2"></graphic>
</fig>
<fig id="fig3" orientation="portrait" position="float"><label>Figure 3</label>
<caption><p>The molecular structure of (III)<xref ref-type="chem" rid="scheme1"></xref>
 showing 50% displacement ellipsoids with the hydrogen bonds indicated by double-dashed lines.</p>
</caption>
<graphic xlink:href="e-75-00167-fig3"></graphic>
</fig>
<fig id="fig4" orientation="portrait" position="float"><label>Figure 4</label>
<caption><p>The molecular structure of (IV)<xref ref-type="chem" rid="scheme1"></xref>
 showing the major disorder component only (50% displacement ellipsoids) with the hydrogen bonds indicated by double-dashed lines.</p>
</caption>
<graphic xlink:href="e-75-00167-fig4"></graphic>
</fig>
<fig id="fig5" orientation="portrait" position="float"><label>Figure 5</label>
<caption><p>The molecular structure of (V)<xref ref-type="chem" rid="scheme1"></xref>
 showing the major disorder component of the methylene groups only (50% displacement ellipsoids) and both disorder components for the N3—H⋯O3 and N3⋯H—O3 hydrogen bonds; the hydrogen bonds are indicated by double-dashed lines.</p>
</caption>
<graphic xlink:href="e-75-00167-fig5"></graphic>
</fig>
<fig id="fig6" orientation="portrait" position="float"><label>Figure 6</label>
<caption><p>Fragment of an [001] hydrogen-bonded chain in the crystal of (I)<xref ref-type="chem" rid="scheme1"></xref>
; the chain in (II)<xref ref-type="chem" rid="scheme1"></xref>
 is almost identical to this. C-bound H atoms omitted for clarity. Symmetry code: (i) <italic>x</italic>
, 1 − y, <inline-formula><inline-graphic xlink:href="e-75-00167-efi14.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
 + <italic>z</italic>
.</p>
</caption>
<graphic xlink:href="e-75-00167-fig6"></graphic>
</fig>
<fig id="fig7" orientation="portrait" position="float"><label>Figure 7</label>
<caption><p>A centrosymmetric hydrogen-bonded tetramer in (III)<xref ref-type="chem" rid="scheme1"></xref>
. Symmetry code: (i) 1 − x, 2 − y, 1 − z.</p>
</caption>
<graphic xlink:href="e-75-00167-fig7"></graphic>
</fig>
<fig id="fig8" orientation="portrait" position="float"><label>Figure 8</label>
<caption><p>Fragment of a [100] hydrogen-bonded chain in the crystal of (IV)<xref ref-type="chem" rid="scheme1"></xref>
; the chain in (V)<xref ref-type="chem" rid="scheme1"></xref>
 is almost identical to this. C-bound H atoms omitted for clarity. Symmetry codes: (i) <italic>x</italic>
 + 1, <italic>y</italic>
, <italic>z</italic>
; (ii) <italic>x</italic>
 − 1, <italic>y</italic>
, <italic>z</italic>
.</p>
</caption>
<graphic xlink:href="e-75-00167-fig8"></graphic>
</fig>
<fig id="fig9" orientation="portrait" position="float"><label>Figure 9</label>
<caption><p>Hirshfeld fingerprint plot for (I)<xref ref-type="chem" rid="scheme1"></xref>
.</p>
</caption>
<graphic xlink:href="e-75-00167-fig9"></graphic>
</fig>
<table-wrap id="table1" orientation="portrait" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (I)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>N</italic>
⋯O1</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.88 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.76 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.632 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">175 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>N</italic>
⋯O2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.83 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.98 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.801 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">170 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H3<italic>N</italic>
⋯O2<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.89 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.93 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.805 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">164 (3)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-75-00167-efi6.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table2" orientation="portrait" position="float"><label>Table 2</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (II)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>N</italic>
⋯O1</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.01 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.62 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.626 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">172 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>N</italic>
⋯O2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.72 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.12 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.816 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">162 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H3<italic>N</italic>
⋯O2<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.88 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.94 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.808 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">170 (4)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-75-00167-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table3" orientation="portrait" position="float"><label>Table 3</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (III)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>N</italic>
⋯O1</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.885 (19)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.838 (19)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.7187 (17)</td>
<td rowspan="1" colspan="1" align="left" valign="top">173.4 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H3<italic>N</italic>
⋯O2<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.90 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.01 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.8509 (19)</td>
<td rowspan="1" colspan="1" align="left" valign="top">156.3 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>N</italic>
⋯O2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.91 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.86 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.7551 (18)</td>
<td rowspan="1" colspan="1" align="left" valign="top">168.3 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">C8—H8<italic>A</italic>
⋯O6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.98</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.43</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.397 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">170</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-75-00167-efi8.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-75-00167-efi9.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table4" orientation="portrait" position="float"><label>Table 4</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (IV)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>N</italic>
⋯O1</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.85 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.84 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.670 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">167 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>N</italic>
⋯O2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.94 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.77 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.704 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">177 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H3<italic>N</italic>
⋯O4<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.91 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.90 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.746 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">153 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N3—H4<italic>N</italic>
⋯O3</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.96 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.67 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.617 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">169 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N4—H5<italic>N</italic>
⋯O4</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.00 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.75 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.754 (7)</td>
<td rowspan="1" colspan="1" align="left" valign="top">178 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N4—H6<italic>N</italic>
⋯O2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.81 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.09 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.763 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">141 (6)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-75-00167-efi10.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-75-00167-efi11.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table5" orientation="portrait" position="float"><label>Table 5</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (V)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>N</italic>
⋯O1</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.93 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.70 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.632 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">175 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>N</italic>
⋯O4<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.89 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.98 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.779 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">149 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H3<italic>N</italic>
⋯O2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.82 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.89 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.716 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">176 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N3—H4<italic>N</italic>
⋯O3</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.87 (8)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.73 (8)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.594 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">166 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N4—H5<italic>N</italic>
⋯O2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.82 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.07 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.804 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">148 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N4—H6<italic>N</italic>
⋯O4</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.92 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.93 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.842 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">169 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O3—H1<italic>O</italic>
⋯N3</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.82 (10)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.78 (10)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.594 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">174 (8)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-75-00167-efi10.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-75-00167-efi11.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table6" orientation="portrait" position="float"><label>Table 6</label>
<caption><title>Hirshfeld contact interactions arising from the C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
 cation (%) in (I)–(V)</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Contact type</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(I)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(II)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(III)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(IV)<italic>a</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(IV)<italic>b</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(V)<italic>a</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">(V)<italic>b</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">H⋯H</td>
<td rowspan="1" colspan="1" align="left" valign="top">68.7</td>
<td rowspan="1" colspan="1" align="left" valign="top">60.9</td>
<td rowspan="1" colspan="1" align="left" valign="top">47.6</td>
<td rowspan="1" colspan="1" align="left" valign="top">62.2</td>
<td rowspan="1" colspan="1" align="left" valign="top">63.3</td>
<td rowspan="1" colspan="1" align="left" valign="top">65.2</td>
<td rowspan="1" colspan="1" align="left" valign="top">65.4</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H⋯Br</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.2</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H⋯O</td>
<td rowspan="1" colspan="1" align="left" valign="top">10.9</td>
<td rowspan="1" colspan="1" align="left" valign="top">12.0</td>
<td rowspan="1" colspan="1" align="left" valign="top">29.1</td>
<td rowspan="1" colspan="1" align="left" valign="top">13.5</td>
<td rowspan="1" colspan="1" align="left" valign="top">13.0</td>
<td rowspan="1" colspan="1" align="left" valign="top">13.4</td>
<td rowspan="1" colspan="1" align="left" valign="top">12.0</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H⋯C</td>
<td rowspan="1" colspan="1" align="left" valign="top">5.9</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.7</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.6</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.0</td>
<td rowspan="1" colspan="1" align="left" valign="top">5.5</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.7</td>
<td rowspan="1" colspan="1" align="left" valign="top">4.2</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H⋯S</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.1</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.8</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.6</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.5</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.0</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.3</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.6</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">C⋯all</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.8</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.9</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.9</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.1</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.1</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.1</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.0</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">N⋯all</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.7</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.7</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.7</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.0</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.9</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.8</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.2</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">S⋯all</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.5</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.3</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.4</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.2</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.4</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.2</td>
<td rowspan="1" colspan="1" align="left" valign="top">6.5</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>‘<italic>a</italic>
’ refers to the S1-containing cation and ‘<italic>b</italic>
’ to the S2-cation.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap-group id="table7" orientation="portrait" position="float"><label>Table 7</label>
<caption><title>Experimental details</title>
</caption>
<table-wrap orientation="portrait" id="d35e2309" position="anchor"><table frame="hsides" rules="groups"><thead valign="top"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top"> </th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(I)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(II)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(III)</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="4" align="left" valign="top">Crystal data</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td>
<td rowspan="1" colspan="1" align="left" valign="top">C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>−</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>−</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>−</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic>
<sub>r</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">346.48</td>
<td rowspan="1" colspan="1" align="left" valign="top">411.35</td>
<td rowspan="1" colspan="1" align="left" valign="top">422.45</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
<italic>c</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
<italic>c</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>n</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td>
<td rowspan="1" colspan="1" align="left" valign="top">173</td>
<td rowspan="1" colspan="1" align="left" valign="top">173</td>
<td rowspan="1" colspan="1" align="left" valign="top">173</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>
, <italic>b</italic>
, <italic>c</italic>
 (Å)</td>
<td rowspan="1" colspan="1" align="left" valign="top">10.1879 (5), 11.6149 (5), 8.7790 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">10.2506 (5), 11.5855 (4), 8.8269 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">17.3232 (6), 5.84087 (17), 21.0876 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">β (°)</td>
<td rowspan="1" colspan="1" align="left" valign="top">113.480 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">113.807 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">109.875 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic>
 (Å<sup>3</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">952.82 (9)</td>
<td rowspan="1" colspan="1" align="left" valign="top">959.07 (8)</td>
<td rowspan="1" colspan="1" align="left" valign="top">2006.60 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">4</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Radiation type</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.18</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.26</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.21</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.24 × 0.11 × 0.02</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.12 × 0.08 × 0.02</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.27 × 0.10 × 0.03</td>
</tr>
<tr><td rowspan="1" colspan="4" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="4" align="left" valign="top">Data collection</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td>
<td rowspan="1" colspan="1" align="left" valign="top">Rigaku XtaLAB P200 HPC</td>
<td rowspan="1" colspan="1" align="left" valign="top">Rigaku XtaLAB P200 HPC</td>
<td rowspan="1" colspan="1" align="left" valign="top">Rigaku XtaLAB P200 HPC</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absorption correction</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>CrysAlis PRO</italic>
; Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>CrysAlis PRO</italic>
; Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>CrysAlis PRO</italic>
; Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>T</italic>
<sub>min</sub>
, <italic>T</italic>
<sub>max</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.793, 1.000</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.761, 1.000</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.566, 1.000</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic>
 > 2σ(<italic>I</italic>
)] reflections</td>
<td rowspan="1" colspan="1" align="left" valign="top">12189, 4056, 3440</td>
<td rowspan="1" colspan="1" align="left" valign="top">12220, 3993, 3311</td>
<td rowspan="1" colspan="1" align="left" valign="top">25034, 4698, 3712</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
<sub>int</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.029</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.026</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.056</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub>
 (Å<sup>−1</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.683</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.683</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.686</td>
</tr>
<tr><td rowspan="1" colspan="4" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="4" align="left" valign="top">Refinement</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)], <italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
), <italic>S</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.038, 0.089, 1.03</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.032, 0.083, 1.06</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.042, 0.116, 1.05</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td>
<td rowspan="1" colspan="1" align="left" valign="top">4056</td>
<td rowspan="1" colspan="1" align="left" valign="top">3993</td>
<td rowspan="1" colspan="1" align="left" valign="top">4698</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td>
<td rowspan="1" colspan="1" align="left" valign="top">230</td>
<td rowspan="1" colspan="1" align="left" valign="top">230</td>
<td rowspan="1" colspan="1" align="left" valign="top">275</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of restraints</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td>
<td rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td>
<td rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td>
<td rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>
, Δρ<sub>min</sub>
 (e Å<sup>−3</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.20, −0.17</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.62, −0.38</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.49, −0.25</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absolute structure</td>
<td rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic>
 determined using 1371 quotients [(<italic>I</italic>
<sup>+</sup>
)−(<italic>I</italic>
<sup>−</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>−</sup>
)] (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb13"> ▸</xref>
).</td>
<td rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic>
 determined using 1344 quotients [(<italic>I</italic>
<sup>+</sup>
)−(<italic>I</italic>
<sup>−</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>−</sup>
)] (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb13"> ▸</xref>
).</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absolute structure parameter</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.03 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.005 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
</tr>
</tbody>
</table>
</table-wrap>
<table-wrap orientation="portrait" id="d35e2847" position="anchor"><table frame="hsides" rules="groups"><thead valign="top"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top"> </th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(IV)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(V)</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="3" align="left" valign="top">Crystal data</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td>
<td rowspan="1" colspan="1" align="left" valign="top">2C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2−</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">1.5C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·0.5C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2−</sup>
·0.5C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>−</sup>
·0.5C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic>
<sub>r</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">536.74</td>
<td rowspan="1" colspan="1" align="left" valign="top">538.75</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
2<sub>1</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
2<sub>1</sub>
</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td>
<td rowspan="1" colspan="1" align="left" valign="top">173</td>
<td rowspan="1" colspan="1" align="left" valign="top">173</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>
, <italic>b</italic>
, <italic>c</italic>
 (Å)</td>
<td rowspan="1" colspan="1" align="left" valign="top">9.0259 (6), 14.7314 (11), 11.1993 (8)</td>
<td rowspan="1" colspan="1" align="left" valign="top">8.9437 (3), 14.7253 (4), 11.2676 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">β (°)</td>
<td rowspan="1" colspan="1" align="left" valign="top">101.943 (6)</td>
<td rowspan="1" colspan="1" align="left" valign="top">100.493 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic>
 (Å<sup>3</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1456.87 (18)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1459.11 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Radiation type</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.22</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.22</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.15 × 0.08 × 0.02</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.32 × 0.15 × 0.02</td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top">Data collection</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td>
<td rowspan="1" colspan="1" align="left" valign="top">Rigaku XtaLAB P200 HPC</td>
<td rowspan="1" colspan="1" align="left" valign="top">Rigaku XtaLAB P200 HPC</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absorption correction</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>CrysAlis PRO</italic>
; Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>CrysAlis PRO</italic>
; Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>T</italic>
<sub>min</sub>
, <italic>T</italic>
<sub>max</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.333, 1.000</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.779, 1.000</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic>
 > 2σ(<italic>I</italic>
)] reflections</td>
<td rowspan="1" colspan="1" align="left" valign="top">19263, 6424, 3792</td>
<td rowspan="1" colspan="1" align="left" valign="top">19079, 6272, 5511</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
<sub>int</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.080</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.034</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub>
 (Å<sup>−1</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.684</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.685</td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top">Refinement</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)], <italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
), <italic>S</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.062, 0.128, 1.00</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.039, 0.094, 1.04</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td>
<td rowspan="1" colspan="1" align="left" valign="top">6424</td>
<td rowspan="1" colspan="1" align="left" valign="top">6272</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td>
<td rowspan="1" colspan="1" align="left" valign="top">350</td>
<td rowspan="1" colspan="1" align="left" valign="top">354</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of restraints</td>
<td rowspan="1" colspan="1" align="left" valign="top">1</td>
<td rowspan="1" colspan="1" align="left" valign="top">1</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td>
<td rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td>
<td rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>
, Δρ<sub>min</sub>
 (e Å<sup>−3</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.27, −0.26</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.26, −0.25</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absolute structure</td>
<td rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic>
 determined using 1279 quotients [(<italic>I</italic>
<sup>+</sup>
)−(<italic>I</italic>
<sup>−</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>−</sup>
)] (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb13"> ▸</xref>
).</td>
<td rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic>
 determined using 2211 quotients [(<italic>I</italic>
<sup>+</sup>
)−(<italic>I</italic>
<sup>−</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>−</sup>
)] (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb13"> ▸</xref>
)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absolute structure parameter</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.46 (7)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.00 (3)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Computer programs: <italic>CrystalClear-SM</italic>
 (Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
), <italic>CrysAlis PRO</italic>
 (Rigaku, 2017<xref ref-type="bibr" rid="bb14"> ▸</xref>
), <italic>SHELXS97</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb18"> ▸</xref>
), <italic>SHELXL2014</italic>
 (Sheldrick, 2015<xref ref-type="bibr" rid="bb19"> ▸</xref>
), <italic>ORTEP-3 for Windows</italic>
 (Farrugia, 2012<xref ref-type="bibr" rid="bb5"> ▸</xref>
) and <italic>publCIF</italic>
 (Westrip, 2010<xref ref-type="bibr" rid="bb22"> ▸</xref>
).</p>
</table-wrap-foot>
</table-wrap>
</table-wrap-group>
</floats-group>
</pmc>
</record>

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Hydrogen-bonded mol­ecular salts of reduced benzo­thia­zole derivatives with carboxyl­ates: a robust (8) supra­molecular motif (even when disordered)

Hydrogen-bonded mol­ecular salts of reduced benzo­thia­zole derivatives with carboxyl­ates: a robust (8) supra­molecular motif (even when disordered)

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Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)

Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)