Expected and unexpected products of reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solvents
Identifieur interne : 000982 ( Pmc/Corpus ); précédent : 000981; suivant : 000983Expected and unexpected products of reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solvents
Auteurs : Alexandra Morscher ; Marcus V. N. De Souza ; James L. Wardell ; William T. A. HarrisonSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2018.
Abstract
Two compounds arose from the same reaction in methanol and the other arose from an unexpected reaction with the acetone solvent.
Url:
DOI: 10.1107/S2056989018005595
PubMed: 29850089
PubMed Central: 5947485
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Expected and unexpected products of reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solvents</title><author><name sortKey="Morscher, Alexandra" sort="Morscher, Alexandra" uniqKey="Morscher A" first="Alexandra" last="Morscher">Alexandra Morscher</name><affiliation><nlm:aff id="a">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country></nlm:aff></affiliation></author><author><name sortKey="De Souza, Marcus V N" sort="De Souza, Marcus V N" uniqKey="De Souza M" first="Marcus V. N." last="De Souza">Marcus V. N. De Souza</name><affiliation><nlm:aff id="b">Instituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ,<country>Brazil</country></nlm:aff></affiliation></author><author><name sortKey="Wardell, James L" sort="Wardell, James L" uniqKey="Wardell J" first="James L." last="Wardell">James L. Wardell</name><affiliation><nlm:aff id="b">Instituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ,<country>Brazil</country></nlm:aff></affiliation><affiliation><nlm:aff id="a">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<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="a">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">29850089</idno><idno type="pmc">5947485</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947485</idno><idno type="RBID">PMC:5947485</idno><idno type="doi">10.1107/S2056989018005595</idno><date when="2018">2018</date><idno type="wicri:Area/Pmc/Corpus">000982</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000982</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Expected and unexpected products of reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solvents</title><author><name sortKey="Morscher, Alexandra" sort="Morscher, Alexandra" uniqKey="Morscher A" first="Alexandra" last="Morscher">Alexandra Morscher</name><affiliation><nlm:aff id="a">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country></nlm:aff></affiliation></author><author><name sortKey="De Souza, Marcus V N" sort="De Souza, Marcus V N" uniqKey="De Souza M" first="Marcus V. N." last="De Souza">Marcus V. N. De Souza</name><affiliation><nlm:aff id="b">Instituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ,<country>Brazil</country></nlm:aff></affiliation></author><author><name sortKey="Wardell, James L" sort="Wardell, James L" uniqKey="Wardell J" first="James L." last="Wardell">James L. Wardell</name><affiliation><nlm:aff id="b">Instituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ,<country>Brazil</country></nlm:aff></affiliation><affiliation><nlm:aff id="a">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<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="a">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="2018">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Two compounds arose from the same reaction in methanol and the other arose from an unexpected reaction with the acetone solvent.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><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">29850089</article-id><article-id pub-id-type="pmc">5947485</article-id><article-id pub-id-type="publisher-id">sj5555</article-id><article-id pub-id-type="doi">10.1107/S2056989018005595</article-id><article-id pub-id-type="coden">ACSECI</article-id><article-id pub-id-type="pii">S2056989018005595</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject></subj-group></article-categories><title-group><article-title>Expected and unexpected products of reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solvents</article-title><alt-title><italic>C<sub>10</sub>H<sub>12</sub>N<sub>3</sub>S<sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup> and two related compounds</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Morscher</surname><given-names>Alexandra</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>de Souza</surname><given-names>Marcus V. N.</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Wardell</surname><given-names>James L.</given-names></name><xref ref-type="aff" rid="b">b</xref><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Harrison</surname><given-names>William T. A.</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country></aff><aff id="b"><label>b</label>Instituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ,<country>Brazil</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>5</month><year>2018</year></pub-date><pub-date pub-type="epub"><day>17</day><month>4</month><year>2018</year></pub-date><pub-date pub-type="pmc-release"><day>17</day><month>4</month><year>2018</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>74</volume><issue>Pt 5</issue><issue-id pub-id-type="publisher-id">e180500</issue-id><fpage>673</fpage><lpage>677</lpage><history><date date-type="received"><day>06</day><month>4</month><year>2018</year></date><date date-type="accepted"><day>10</day><month>4</month><year>2018</year></date></history><permissions><copyright-statement>© Morscher et al. 2018</copyright-statement><copyright-year>2018</copyright-year><license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><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/2.0/uk/</ali:license_ref></license></permissions><self-uri xlink:href="https://doi.org/10.1107/S2056989018005595">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract abstract-type="toc"><p>Two compounds arose from the same reaction in methanol and the other arose from an unexpected reaction with the acetone solvent.</p></abstract><abstract><p>The syntheses and crystal structures of 2-[2-(propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium 3-nitrobenzenesulfonate (C<sub>10</sub>H<sub>12</sub>N<sub>2</sub>S<sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup>), (I), 2-[2-(3-nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (C<sub>13</sub>H<sub>10</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub>), (II) and 2-[2-(3-nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium 3-nitrobenzenesulfonate (C<sub>13</sub>H<sub>11</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub><sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup>), (III) are reported. Salt (I) arose from an unexpected reaction of 2-hydrazinylbenzothiazole with the acetone solvent in the presence of 3-nitrobenzenesulfonyl chloride, whereas (II) and (III) were recovered from the equivalent reaction carried out in methanol. The crystal of (I) features ion pairs linked by pairs of N—H⋯O<sub>s</sub> (s = sulfonate) hydrogen bonds; adjacent cations interact by way of short π–π stacking interactions between the thiazole rings [centroid–centroid separation = 3.4274 (18) Å]. In (II), which crystallizes with two neutral molecules in the asymmetric unit, the molecules are linked by N—H⋯N and N—H⋯O<sub>n</sub> (n = nitro) hydrogen bonds to generate [<inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>1<inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>] chains, which are cross-linked by C—H⋯O and π–π stacking interactions. The crystal of (III) features centrosymmetric tetramers (two cations and two anions) linked by cooperative N—H⋯O hydrogen bonds; C—H⋯O and π–π interactions occur between tetramers.</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>hydrazinylbenzothiazole</kwd><kwd>hydrogen bonds</kwd><kwd>molecular salt</kwd></kwd-group><funding-group><award-group><funding-source>Conselho Nacional de Desenvolvimento Científico e Tecnológico</funding-source><principal-award-recipient>M.V.N. de Souza</principal-award-recipient><principal-award-recipient>J.L. Wardell</principal-award-recipient></award-group><funding-statement>This work was funded by <funding-source>Conselho Nacional de Desenvolvimento Científico e Tecnológico</funding-source> grant to M.V.N. de Souza and J.L. Wardell. </funding-statement></funding-group><conference><conf-date></conf-date><conf-name>Special issue on Weak interactions in crystals: an integrated approach</conf-name><conf-loc></conf-loc></conference><counts><page-count count="5"></page-count></counts></article-meta></front><body><sec id="sec1"><title>Chemical context </title><p>Heteroaromatic benzothiazole derivatives are well-studied compounds, due in the main to their various and useful biological activities (for a review, see Gulati <italic>et al.</italic>, 2017<xref ref-type="bibr" rid="bb7"> ▸</xref>), but also to their fluorescent and optical properties (<italic>e.g.</italic> Liu <italic>et al.</italic>, 2018<xref ref-type="bibr" rid="bb10"> ▸</xref>). Hydrazonyl derivatives, 2-Ar—CH=N—NH-benzothiazoles, formed from 2-hydrazinylbenzothiazole and ArCHO have attracted attention: for example, Katava <italic>et al.</italic> (2017<xref ref-type="bibr" rid="bb9"> ▸</xref>) have reported antitumor activities and Behera & Manivannan (2017<xref ref-type="bibr" rid="bb1"> ▸</xref>) studied their use as sensors. Less attention has been paid generally to 2-(ArSO<sub>2</sub>NHNH)-benzothiazoles, although antimicrobial activities have been briefly reported (Rao <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb13"> ▸</xref>; Hipparagi <italic>et al.</italic>, 2007<xref ref-type="bibr" rid="bb8"> ▸</xref>).</p><p>We have initiated a study of the syntheses, structures and biological activities of 2-(ArSO<sub>2</sub>NHNH)-benzothiazoles and we now describe the structures of three products of the reactions of 2-hydrazinylbenzothiazole with 3-nitrobenzenesulfonyl chloride in different solvents, <italic>viz</italic>. 2-[2-(propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium 3-nitrobenzenesulfonate (I)<xref ref-type="chem" rid="scheme1"></xref>, 2-[2-(3-nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II)<xref ref-type="chem" rid="scheme1"></xref> and 2-[2-(3-nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium 3-nitrobenzenesulfonate (III)<xref ref-type="chem" rid="scheme1"></xref>.<chem-struct id="scheme1"><graphic xlink:href="e-74-00673-scheme1.jpg" position="float" orientation="portrait"></graphic></chem-struct></p></sec><sec id="sec2"><title>Structural commentary </title><p>Compound (I)<xref ref-type="chem" rid="scheme1"></xref> crystallizes in space group <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula> with one C<sub>10</sub>H<sub>12</sub>N<sub>3</sub>S<sup>+</sup> cation (protonated at N1) and one C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup> sulfonate anion in the asymmetric unit (Fig. 1<xref ref-type="fig" rid="fig1"> ▸</xref>). Evidently, the starting hydrazone has reacted with the acetone solvent (Day & Whiting, 1970<xref ref-type="bibr" rid="bb2"> ▸</xref>) to generate an <italic>N</italic>-propylidine group; at the same time, the sulfonyl chloride has been hydrolysed to sulfonic acid and a molecular salt has crystallized after proton transfer from the sulfonic acid to the N atom of the thiazole ring. The cation is close to planar; the dihedral angle between the benzothiazole ring system (r.m.s. deviation = 0.005 Å) and the N2/N3/C8/C9/C10 grouping (r.m.s. deviation = 0.004 Å) is 7.89 (10)°; the C7—N2—N3—C8 torsion angle is −172.8 (2)°. The C8—N3 bond length of 1.278 (4) Å is fully consistent with double-bond character. In the anion, the nitro group is twisted by 26.7 (4)° with respect to the benzene ring. As expected, the S—O bond lengths of the sulfonate group are almost the same, indicating the usual delocalization of the negative charge and the same situation is found in compound (III)<xref ref-type="chem" rid="scheme1"></xref> described below.</p><p>Compound (II)<xref ref-type="chem" rid="scheme1"></xref> represents the expected condensation product of the starting hydrazone and sulfonyl chloride and crystallizes with two neutral C<sub>13</sub>H<sub>10</sub>N<sub>4</sub>O<sub>4</sub>S molecules in the asymmetric unit (Fig. 2<xref ref-type="fig" rid="fig2"> ▸</xref>) in space group <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>. In the first (S1) molecule, the dihedral angle between the benzothiazole ring system (r.m.s. deviation = 0.013 Å) and the C8 benzene ring is 32.59 (4)°; the nitro group is twisted by 0.68 (7)° from the C8 benzene ring. The C7—N2—N3—S2 torsion angle is −99.88 (12) and the H2—N2—N3—H3 torsion angle is −54 (2)°. The bond-angle sum at N2 is 359.9°, indicative of <italic>sp</italic><sup>2</sup> hybridization, whereas the corresponding value for N3 of 341.1° points towards substantial <italic>sp</italic><sup>3</sup> hybrid character. The C7—N2 bond length of 1.3529 (16) Å is short for a nominal single bond, presumably indicative of conjugation of the N2 nominal lone pair of electrons with the adjacent ring system. In the second (S3) molecule, the corresponding geometrical data are 0.008 Å (r.m.s. deviation for S3 ring system), 30.01 (3)° (S3/C21 rings), 3.46 (13)° (nitro group and C21 ring), −103.53 (12)° (C20—N6—N7—S4), −50.3 (18)° (H6—N6—N7—H7), 359.9° (bond-angle sum at N6), 341.7° (bond-angle sum at N7) and 1.3549 (16) Å (C20—N6 bond length). All-in-all, the S1 and S3 molecules have similar conformations as indicated by the r.m.s. overlay fit of 0.221 Å for their non-hydrogen atoms.</p><p>Compound (III)<xref ref-type="chem" rid="scheme1"></xref>, which was recovered from the same reaction as (II)<xref ref-type="chem" rid="scheme1"></xref>, represents the same condensation product, which has gone on to further react with a hydrolysed sulfonyl chloride species to form a molecular salt (proton transfer to N1). Once again, the space group is <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula> and one cation and one anion (Fig. 3<xref ref-type="fig" rid="fig3"> ▸</xref>) make up the asymmetric unit. The benzothiazole ring system (r.m.s. deviation = 0.005 Å) subtends a dihedral angle of 57.54 (3)° with the C8 benzene ring and the nitro group is twisted from its attached ring by 4.8 (3)°. The C7—N2—N3—S2 and H2—N2—N3—H3 torsion angles are −110.54 (12) and −48.5 (19)°, respectively. The bond-angle sums at N2 and N3 are 359.0 and 339.1°, respectively, and the same conclusions <italic>re</italic> hybridization states for these atoms as in (II)<xref ref-type="chem" rid="scheme1"></xref> may be drawn. This is backed up by the shortened C7—N2 bond length of 1.3317 (17) Å in (III)<xref ref-type="chem" rid="scheme1"></xref> compared to (II)<xref ref-type="chem" rid="scheme1"></xref>. presumably because resonance is enhanced by the positive charge on N1. In the anion, the nitro group is twisted from its attached ring by 17.7 (2)°.</p></sec><sec id="sec3"><title>Supramolecular features </title><p>In the crystal of (I)<xref ref-type="chem" rid="scheme1"></xref>, the cation and the anion are linked by a pair of N—H⋯O hydrogen bonds (Table 1<xref ref-type="table" rid="table1"> ▸</xref>), which generate an <inline-formula><inline-graphic xlink:href="e-74-00673-efi6.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) loop. The ion pairs are connected by various weak C—H⋯O interactions, with the acceptor O atoms being parts of the sulfonate and nitro groups. No C—H⋯π interactions could be identified in the crystal of (I)<xref ref-type="chem" rid="scheme1"></xref> but aromatic π–π stacking interactions are seen, with the shortest centroid–centroid separation of 3.4274 (18) Å (slippage = 0.729 Å) occurring between inversion-related pairs of thiazole rings (Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>); atom N2 of the hydrazone group lies above the benzene ring (<italic>Cg</italic>⋯N2 = 3.385 Å) and possibly provides some additional stabilization. Taken together, the directional intermolecular interactions in (I)<xref ref-type="chem" rid="scheme1"></xref> generate a three-dimensional network.</p><p>The dominant intermolecular interactions in (II)<xref ref-type="chem" rid="scheme1"></xref> are N—H⋯N and N—H⋯O hydrogen bonds (Table 2<xref ref-type="table" rid="table2"> ▸</xref>); the first of these (N2—H2⋯N5 and N6—H6⋯N1) occur in the arbitrarily chosen asymmetric unit to link the molecules into dimers that ‘slot together’: the dihedral angle between the benzothiazole planes in the two molecules is 36.06 (4)° and the pendant benzene sulfonyl groups project to the same side of the ensemble. The N—H⋯O<sub>n</sub> (n = nitro) links connect the dimers into infinite [<inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>1<inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>] chains (Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>). A number of weak C—H⋯O interactions are also observed, which serve to cross-link the chains. Several π–π stacking contacts occur in the crystal of (II)<xref ref-type="chem" rid="scheme1"></xref>, with the shortest [centroid–centroid separation = 3.5186 (7)Å] occurring between the C8–C13 and C14–C19 rings. Finally, a short N8—O7⋯π (π = centroid of the C21–C26 benzene ring) contact is observed with N⋯π = 3.2497 (12) Å and N—O⋯π = 86.24 (8)°.</p><p>The packing in (III)<xref ref-type="chem" rid="scheme1"></xref> features a pair of cation-to-anion N—H⋯O links from N1 and N2 (Table 3<xref ref-type="table" rid="table3"> ▸</xref>), which is essentially the same motif as seen in (I)<xref ref-type="chem" rid="scheme1"></xref>. The N3—H3 grouping links to a symmetry-generated sulfonate O atom and a centrosymmetric tetramer (two cations and two anions) results (Fig. 6<xref ref-type="fig" rid="fig6"> ▸</xref>). A pair of weak C—H⋯O interactions helps to provide cohesion between tetramers in the crystal and π–π stacking is also observed, with the shortest centroid–centroid separation being 3.6743 (8) Å between the thiazole and C1–C6 rings.</p></sec><sec id="sec4"><title>Database survey </title><p>A survey of of the Cambridge Structural Database (Groom <italic>et al.</italic>, 2016<xref ref-type="bibr" rid="bb6"> ▸</xref>: updated to March 2018) for benzothiazole hydrazones revealed the prototype compound, benzothiazol-2-yl-hydrazine (refcode: NAPKAR; Rajnikant <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb12"> ▸</xref>) as well as three derivatives with various substituents attached to the benzene ring, <italic>viz</italic>. EVARID (Liu <italic>et al.</italic>, 2011<xref ref-type="bibr" rid="bb11"> ▸</xref>), LAPCAI (Fun <italic>et al.</italic>, 2012<italic>a</italic><xref ref-type="bibr" rid="bb4"> ▸</xref>) and LEFTEX (Fun <italic>et al.</italic>, 2012<italic>b</italic><xref ref-type="bibr" rid="bb5"> ▸</xref>). No hits for benzenesulfonylhydrazino-benzothiazoles were recorded.</p></sec><sec id="sec5"><title>Synthesis and crystallization </title><p>To prepare (I)<xref ref-type="chem" rid="scheme1"></xref>, a mixture of 2-hydrazinylbenzothiazole (1.00 mmol) and 3-nitrobenzenesulfonyl chloride (1.00 mmol) in acetone (15 ml) was gently heated at 313–323 K for 30 minutes, then rotary evaporated and the residue was recrystallized by slow evaporation from methanol solution at room temperature; m.p. 444–445 K. ESI–HRMS (<italic>M</italic> + H). Calculated: 206.0752 for C<sub>10</sub>H<sub>12</sub>N<sub>3</sub>S, found: 206.0755. IR: 2930(br), 1621, 1530, 1350, 1241, 1151, 1028 cm<sup>−1</sup></p><p>Compounds (II)<xref ref-type="chem" rid="scheme1"></xref> and (III)<xref ref-type="chem" rid="scheme1"></xref> arose from the same reaction: a solution of 2-hydrazinylbenzothiazole (1.00 mmol) and 3-nitrobenzenesulfonyl chloride (1.00 mmol) in methanol (15 ml) was gently heated at 313–323 K for 30 minutes, then rotary evaporated and the residue was recrystallized by slow evaporation from methanol solution at room temperature. A mixture of two distinct crystalline products, one yellow [compound (II)] and the other colourless [compound (III)], was isolated. These were separated by eye, and each product was futher recrystallized from methanol solution. (II)<xref ref-type="chem" rid="scheme1"></xref>; m.p. 442–444 K. ESI–HRMS (<italic>M</italic> − H). Calculated: 349.0222 for C<sub>13</sub>H<sub>9</sub>N<sub>4</sub>O<sub>2</sub>S<sub>2</sub>: found: 351.0220 ESI–HRMS (<italic>M</italic> + H). Calculated: 351.0065 for C<sub>13</sub>H<sub>11</sub>N<sub>4</sub>O<sub>2</sub>S<sub>2</sub>: found: 349.0062 IR; 2989 (<italic>br</italic>), 1531, 1457, 1341, 1306, 1167 cm<sup>−1</sup>. (III)<xref ref-type="chem" rid="scheme1"></xref>: m.p. 463–466 K. ESI–HRMS (<italic>M</italic> + H). Calculated: 351.0065 for C<sub>13</sub>H<sub>11</sub>N<sub>4</sub>O<sub>2</sub>S<sub>2</sub>: found: 349.0065 IR: 2870 (<italic>br</italic>), 1553, 1436, 1363, 1241, 1127, 1065 cm<sup>−1</sup>.</p></sec><sec id="sec6"><title>Refinement </title><p>Crystal data, data collection and structure refinement details are summarized in Table 4<xref ref-type="table" rid="table4"> ▸</xref>. The N-bound hydrogen atoms were located in difference maps and their positions freely refined. The C-bound hydrogen atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding atoms. 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 in all cases. The methyl groups in (I)<xref ref-type="chem" rid="scheme1"></xref> were allowed to rotate, but not to tip, to best fit the electron density.</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, global. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018005595/sj5555sup1.cif">10.1107/S2056989018005595/sj5555sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-74-00673-sup1.cif" orientation="portrait" id="d35e153" 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/S2056989018005595/sj5555Isup2.hkl">10.1107/S2056989018005595/sj5555Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-74-00673-Isup2.hkl" orientation="portrait" id="d35e160" 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/S2056989018005595/sj5555IIsup3.hkl">10.1107/S2056989018005595/sj5555IIsup3.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-74-00673-IIsup3.hkl" orientation="portrait" id="d35e167" 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/S2056989018005595/sj5555IIIsup4.hkl">10.1107/S2056989018005595/sj5555IIIsup4.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-74-00673-IIIsup4.hkl" orientation="portrait" id="d35e174" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-74-00673-Isup5.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/S2056989018005595/sj5555Isup5.cml">10.1107/S2056989018005595/sj5555Isup5.cml</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-74-00673-IIsup6.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/S2056989018005595/sj5555IIsup6.cml">10.1107/S2056989018005595/sj5555IIsup6.cml</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-74-00673-IIIsup7.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/S2056989018005595/sj5555IIIsup7.cml">10.1107/S2056989018005595/sj5555IIIsup7.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=1835988">1835988</ext-link>, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1835987">1835987</ext-link>, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1835986">1835986</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?sj5555&file=sj5555sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?sj5555sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?sj5555&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><ack><p>We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.</p></ack><app-group><app><title>supplementary crystallographic information</title><sec id="d1e139" sec-type="tablewrapcrystaldatalong"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Crystal data</title><table-wrap position="anchor" id="d1e148"><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>10</sub>H<sub>12</sub>N<sub>3</sub>S<sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup></td><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 408.45</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 424</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.528 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 7.5308 (4) Å</td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71075 Å</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 10.9167 (7) Å</td><td rowspan="1" colspan="1">Cell parameters from 6372 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.4438 (8) Å</td><td rowspan="1" colspan="1">θ = 2.8–30.4°</td></tr><tr><td rowspan="1" colspan="1">α = 66.058 (6)°</td><td rowspan="1" colspan="1">µ = 0.34 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 79.034 (5)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 100 K</td></tr><tr><td rowspan="1" colspan="1">γ = 72.156 (5)°</td><td rowspan="1" colspan="1">Block, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 887.47 (10) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.06 × 0.05 × 0.01 mm</td></tr></table></table-wrap></sec><sec id="d1e284" sec-type="tablewrapdatacollectionlong"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Data collection</title><table-wrap position="anchor" id="d1e293"><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 Mercury CCD diffractometer</td><td rowspan="1" colspan="1">3249 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.036</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>FS_ABSCOR</italic>; Rigaku, 2013)</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 26.0°, θ<sub>min</sub> = 2.9°</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.614, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>h</italic> = −9→7</td></tr><tr><td rowspan="1" colspan="1">11341 measured reflections</td><td rowspan="1" colspan="1"><italic>k</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1">3490 independent reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −15→15</td></tr></table></table-wrap></sec><sec id="d1e393" sec-type="tablewraprefinementdatalong"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Refinement</title><table-wrap position="anchor" id="d1e402"><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>)] = 0.066</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>) = 0.184</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.1206<italic>P</italic>)<sup>2</sup> + 0.8477<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> = 1.11</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.001</td></tr><tr><td rowspan="1" colspan="1">3490 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 1.32 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">250 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.63 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="d1e548" sec-type="specialdetails"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Special details</title><table-wrap position="anchor" id="d1e558"><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="d1e567" sec-type="tablewrapcoords"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e579"><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">0.2281 (4)</td><td rowspan="1" colspan="1">0.3162 (3)</td><td rowspan="1" colspan="1">0.5033 (3)</td><td rowspan="1" colspan="1">0.0203 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.2122 (4)</td><td rowspan="1" colspan="1">0.1899 (3)</td><td rowspan="1" colspan="1">0.5087 (3)</td><td rowspan="1" colspan="1">0.0228 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2A</td><td rowspan="1" colspan="1">0.2284</td><td rowspan="1" colspan="1">0.1105</td><td rowspan="1" colspan="1">0.5798</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.1720 (4)</td><td rowspan="1" colspan="1">0.1837 (3)</td><td rowspan="1" colspan="1">0.4070 (3)</td><td rowspan="1" colspan="1">0.0262 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.1611</td><td rowspan="1" colspan="1">0.0986</td><td rowspan="1" colspan="1">0.4083</td><td rowspan="1" colspan="1">0.031*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.1472 (4)</td><td rowspan="1" colspan="1">0.3006 (3)</td><td rowspan="1" colspan="1">0.3030 (3)</td><td rowspan="1" colspan="1">0.0248 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.1204</td><td rowspan="1" colspan="1">0.2937</td><td rowspan="1" colspan="1">0.2344</td><td rowspan="1" colspan="1">0.030*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.1609 (4)</td><td rowspan="1" colspan="1">0.4267 (3)</td><td rowspan="1" colspan="1">0.2978 (3)</td><td rowspan="1" colspan="1">0.0231 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.1419</td><td rowspan="1" colspan="1">0.5065</td><td rowspan="1" colspan="1">0.2270</td><td rowspan="1" colspan="1">0.028*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.2032 (4)</td><td rowspan="1" colspan="1">0.4330 (3)</td><td rowspan="1" colspan="1">0.3988 (3)</td><td rowspan="1" colspan="1">0.0191 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.2606 (4)</td><td rowspan="1" colspan="1">0.5238 (3)</td><td rowspan="1" colspan="1">0.5207 (3)</td><td rowspan="1" colspan="1">0.0187 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.3338 (4)</td><td rowspan="1" colspan="1">0.6563 (3)</td><td rowspan="1" colspan="1">0.7133 (3)</td><td rowspan="1" colspan="1">0.0228 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.2989 (5)</td><td rowspan="1" colspan="1">0.8099 (3)</td><td rowspan="1" colspan="1">0.6481 (3)</td><td rowspan="1" colspan="1">0.0276 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9A</td><td rowspan="1" colspan="1">0.3122</td><td rowspan="1" colspan="1">0.8531</td><td rowspan="1" colspan="1">0.7004</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9B</td><td rowspan="1" colspan="1">0.3897</td><td rowspan="1" colspan="1">0.8293</td><td rowspan="1" colspan="1">0.5795</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9C</td><td rowspan="1" colspan="1">0.1719</td><td rowspan="1" colspan="1">0.8476</td><td rowspan="1" colspan="1">0.6217</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.3777 (5)</td><td rowspan="1" colspan="1">0.6021 (4)</td><td rowspan="1" colspan="1">0.8395 (3)</td><td rowspan="1" colspan="1">0.0298 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10A</td><td rowspan="1" colspan="1">0.3780</td><td rowspan="1" colspan="1">0.6793</td><td rowspan="1" colspan="1">0.8606</td><td rowspan="1" colspan="1">0.045*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10B</td><td rowspan="1" colspan="1">0.2827</td><td rowspan="1" colspan="1">0.5556</td><td rowspan="1" colspan="1">0.8906</td><td rowspan="1" colspan="1">0.045*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10C</td><td rowspan="1" colspan="1">0.5011</td><td rowspan="1" colspan="1">0.5359</td><td rowspan="1" colspan="1">0.8499</td><td rowspan="1" colspan="1">0.045*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.2209 (3)</td><td rowspan="1" colspan="1">0.5486 (3)</td><td rowspan="1" colspan="1">0.4133 (2)</td><td rowspan="1" colspan="1">0.0190 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.188 (5)</td><td rowspan="1" colspan="1">0.633 (4)</td><td rowspan="1" colspan="1">0.364 (3)</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.2853 (3)</td><td rowspan="1" colspan="1">0.6164 (3)</td><td rowspan="1" colspan="1">0.5555 (2)</td><td rowspan="1" colspan="1">0.0197 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.272 (5)</td><td rowspan="1" colspan="1">0.697 (4)</td><td rowspan="1" colspan="1">0.509 (3)</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.3282 (3)</td><td rowspan="1" colspan="1">0.5676 (3)</td><td rowspan="1" colspan="1">0.6723 (2)</td><td rowspan="1" colspan="1">0.0221 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.27708 (10)</td><td rowspan="1" colspan="1">0.35384 (7)</td><td rowspan="1" colspan="1">0.61732 (6)</td><td rowspan="1" colspan="1">0.0196 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.4451 (4)</td><td rowspan="1" colspan="1">0.9109 (3)</td><td rowspan="1" colspan="1">0.1794 (2)</td><td rowspan="1" colspan="1">0.0183 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.5278 (4)</td><td rowspan="1" colspan="1">0.8235 (3)</td><td rowspan="1" colspan="1">0.1184 (2)</td><td rowspan="1" colspan="1">0.0195 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.4602</td><td rowspan="1" colspan="1">0.7699</td><td rowspan="1" colspan="1">0.1067</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.7139 (4)</td><td rowspan="1" colspan="1">0.8170 (3)</td><td rowspan="1" colspan="1">0.0747 (3)</td><td rowspan="1" colspan="1">0.0223 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.8145 (4)</td><td rowspan="1" colspan="1">0.8949 (3)</td><td rowspan="1" colspan="1">0.0890 (3)</td><td rowspan="1" colspan="1">0.0262 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">0.9422</td><td rowspan="1" colspan="1">0.8861</td><td rowspan="1" colspan="1">0.0602</td><td rowspan="1" colspan="1">0.031*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.7274 (4)</td><td rowspan="1" colspan="1">0.9858 (3)</td><td rowspan="1" colspan="1">0.1455 (3)</td><td rowspan="1" colspan="1">0.0259 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.7938</td><td rowspan="1" colspan="1">1.0430</td><td rowspan="1" colspan="1">0.1529</td><td rowspan="1" colspan="1">0.031*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.5418 (4)</td><td rowspan="1" colspan="1">0.9941 (3)</td><td rowspan="1" colspan="1">0.1918 (3)</td><td rowspan="1" colspan="1">0.0221 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.4820</td><td rowspan="1" colspan="1">1.0560</td><td rowspan="1" colspan="1">0.2315</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">0.21789 (9)</td><td rowspan="1" colspan="1">0.91074 (7)</td><td rowspan="1" colspan="1">0.25157 (6)</td><td rowspan="1" colspan="1">0.0184 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.8044 (4)</td><td rowspan="1" colspan="1">0.7214 (3)</td><td rowspan="1" colspan="1">0.0138 (2)</td><td rowspan="1" colspan="1">0.0302 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.1647 (3)</td><td rowspan="1" colspan="1">0.8018 (2)</td><td rowspan="1" colspan="1">0.23498 (18)</td><td rowspan="1" colspan="1">0.0222 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.2432 (3)</td><td rowspan="1" colspan="1">0.8753 (2)</td><td rowspan="1" colspan="1">0.37542 (18)</td><td rowspan="1" colspan="1">0.0238 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.1002 (3)</td><td rowspan="1" colspan="1">1.0479 (2)</td><td rowspan="1" colspan="1">0.19792 (19)</td><td rowspan="1" colspan="1">0.0255 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.7054 (4)</td><td rowspan="1" colspan="1">0.6912 (3)</td><td rowspan="1" colspan="1">−0.0342 (2)</td><td rowspan="1" colspan="1">0.0360 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.9750 (3)</td><td rowspan="1" colspan="1">0.6763 (3)</td><td rowspan="1" colspan="1">0.0148 (2)</td><td rowspan="1" colspan="1">0.0432 (7)</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e1124" sec-type="tablewrapadps"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e1136"><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">0.0162 (13)</td><td rowspan="1" colspan="1">0.0222 (14)</td><td rowspan="1" colspan="1">0.0203 (14)</td><td rowspan="1" colspan="1">−0.0039 (11)</td><td rowspan="1" colspan="1">0.0017 (11)</td><td rowspan="1" colspan="1">−0.0077 (11)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0213 (14)</td><td rowspan="1" colspan="1">0.0197 (14)</td><td rowspan="1" colspan="1">0.0270 (15)</td><td rowspan="1" colspan="1">−0.0063 (11)</td><td rowspan="1" colspan="1">0.0015 (12)</td><td rowspan="1" colspan="1">−0.0089 (12)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0203 (14)</td><td rowspan="1" colspan="1">0.0263 (15)</td><td rowspan="1" colspan="1">0.0358 (17)</td><td rowspan="1" colspan="1">−0.0088 (12)</td><td rowspan="1" colspan="1">0.0037 (13)</td><td rowspan="1" colspan="1">−0.0158 (14)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0183 (14)</td><td rowspan="1" colspan="1">0.0342 (16)</td><td rowspan="1" colspan="1">0.0259 (15)</td><td rowspan="1" colspan="1">−0.0076 (12)</td><td rowspan="1" colspan="1">0.0028 (12)</td><td rowspan="1" colspan="1">−0.0164 (13)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0171 (13)</td><td rowspan="1" colspan="1">0.0290 (15)</td><td rowspan="1" colspan="1">0.0204 (14)</td><td rowspan="1" colspan="1">−0.0085 (12)</td><td rowspan="1" colspan="1">0.0039 (11)</td><td rowspan="1" colspan="1">−0.0069 (12)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0122 (12)</td><td rowspan="1" colspan="1">0.0201 (13)</td><td rowspan="1" colspan="1">0.0227 (14)</td><td rowspan="1" colspan="1">−0.0056 (10)</td><td rowspan="1" colspan="1">0.0048 (11)</td><td rowspan="1" colspan="1">−0.0073 (11)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0099 (12)</td><td rowspan="1" colspan="1">0.0218 (14)</td><td rowspan="1" colspan="1">0.0226 (14)</td><td rowspan="1" colspan="1">−0.0058 (10)</td><td rowspan="1" colspan="1">0.0047 (10)</td><td rowspan="1" colspan="1">−0.0078 (11)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0135 (13)</td><td rowspan="1" colspan="1">0.0302 (16)</td><td rowspan="1" colspan="1">0.0254 (15)</td><td rowspan="1" colspan="1">−0.0100 (12)</td><td rowspan="1" colspan="1">0.0056 (11)</td><td rowspan="1" colspan="1">−0.0107 (13)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0294 (16)</td><td rowspan="1" colspan="1">0.0281 (16)</td><td rowspan="1" colspan="1">0.0300 (16)</td><td rowspan="1" colspan="1">−0.0103 (13)</td><td rowspan="1" colspan="1">−0.0003 (13)</td><td rowspan="1" colspan="1">−0.0140 (13)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0295 (16)</td><td rowspan="1" colspan="1">0.0390 (18)</td><td rowspan="1" colspan="1">0.0248 (16)</td><td rowspan="1" colspan="1">−0.0160 (14)</td><td rowspan="1" colspan="1">0.0026 (13)</td><td rowspan="1" colspan="1">−0.0125 (14)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0162 (11)</td><td rowspan="1" colspan="1">0.0178 (12)</td><td rowspan="1" colspan="1">0.0196 (12)</td><td rowspan="1" colspan="1">−0.0062 (9)</td><td rowspan="1" colspan="1">0.0028 (9)</td><td rowspan="1" colspan="1">−0.0042 (10)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0188 (12)</td><td rowspan="1" colspan="1">0.0178 (12)</td><td rowspan="1" colspan="1">0.0214 (12)</td><td rowspan="1" colspan="1">−0.0070 (10)</td><td rowspan="1" colspan="1">0.0009 (10)</td><td rowspan="1" colspan="1">−0.0056 (10)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0178 (12)</td><td rowspan="1" colspan="1">0.0264 (13)</td><td rowspan="1" colspan="1">0.0220 (12)</td><td rowspan="1" colspan="1">−0.0088 (10)</td><td rowspan="1" colspan="1">0.0023 (10)</td><td rowspan="1" colspan="1">−0.0084 (10)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.0197 (4)</td><td rowspan="1" colspan="1">0.0179 (4)</td><td rowspan="1" colspan="1">0.0193 (4)</td><td rowspan="1" colspan="1">−0.0062 (3)</td><td rowspan="1" colspan="1">−0.0008 (3)</td><td rowspan="1" colspan="1">−0.0044 (3)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0153 (13)</td><td rowspan="1" colspan="1">0.0199 (13)</td><td rowspan="1" colspan="1">0.0170 (13)</td><td rowspan="1" colspan="1">−0.0062 (11)</td><td rowspan="1" colspan="1">−0.0021 (10)</td><td rowspan="1" colspan="1">−0.0026 (11)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0202 (14)</td><td rowspan="1" colspan="1">0.0197 (13)</td><td rowspan="1" colspan="1">0.0168 (13)</td><td rowspan="1" colspan="1">−0.0071 (11)</td><td rowspan="1" colspan="1">−0.0021 (11)</td><td rowspan="1" colspan="1">−0.0034 (11)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0201 (14)</td><td rowspan="1" colspan="1">0.0241 (14)</td><td rowspan="1" colspan="1">0.0174 (13)</td><td rowspan="1" colspan="1">−0.0032 (12)</td><td rowspan="1" colspan="1">−0.0003 (11)</td><td rowspan="1" colspan="1">−0.0045 (11)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0156 (13)</td><td rowspan="1" colspan="1">0.0353 (17)</td><td rowspan="1" colspan="1">0.0207 (14)</td><td rowspan="1" colspan="1">−0.0068 (12)</td><td rowspan="1" colspan="1">−0.0018 (11)</td><td rowspan="1" colspan="1">−0.0029 (12)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0177 (14)</td><td rowspan="1" colspan="1">0.0363 (17)</td><td rowspan="1" colspan="1">0.0250 (15)</td><td rowspan="1" colspan="1">−0.0141 (13)</td><td rowspan="1" colspan="1">−0.0015 (12)</td><td rowspan="1" colspan="1">−0.0077 (13)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0217 (14)</td><td rowspan="1" colspan="1">0.0231 (14)</td><td rowspan="1" colspan="1">0.0213 (14)</td><td rowspan="1" colspan="1">−0.0066 (12)</td><td rowspan="1" colspan="1">−0.0024 (11)</td><td rowspan="1" colspan="1">−0.0071 (12)</td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">0.0147 (4)</td><td rowspan="1" colspan="1">0.0195 (4)</td><td rowspan="1" colspan="1">0.0200 (4)</td><td rowspan="1" colspan="1">−0.0077 (3)</td><td rowspan="1" colspan="1">0.0015 (3)</td><td rowspan="1" colspan="1">−0.0051 (3)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0333 (15)</td><td rowspan="1" colspan="1">0.0265 (14)</td><td rowspan="1" colspan="1">0.0196 (13)</td><td rowspan="1" colspan="1">−0.0047 (12)</td><td rowspan="1" colspan="1">0.0065 (11)</td><td rowspan="1" colspan="1">−0.0033 (11)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0214 (10)</td><td rowspan="1" colspan="1">0.0224 (10)</td><td rowspan="1" colspan="1">0.0223 (10)</td><td rowspan="1" colspan="1">−0.0098 (8)</td><td rowspan="1" colspan="1">−0.0013 (8)</td><td rowspan="1" colspan="1">−0.0049 (8)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0250 (11)</td><td rowspan="1" colspan="1">0.0247 (11)</td><td rowspan="1" colspan="1">0.0221 (11)</td><td rowspan="1" colspan="1">−0.0119 (9)</td><td rowspan="1" colspan="1">0.0029 (8)</td><td rowspan="1" colspan="1">−0.0071 (8)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0174 (10)</td><td rowspan="1" colspan="1">0.0240 (11)</td><td rowspan="1" colspan="1">0.0305 (12)</td><td rowspan="1" colspan="1">−0.0078 (9)</td><td rowspan="1" colspan="1">0.0016 (9)</td><td rowspan="1" colspan="1">−0.0052 (9)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0485 (15)</td><td rowspan="1" colspan="1">0.0343 (13)</td><td rowspan="1" colspan="1">0.0270 (12)</td><td rowspan="1" colspan="1">−0.0169 (11)</td><td rowspan="1" colspan="1">0.0107 (11)</td><td rowspan="1" colspan="1">−0.0144 (10)</td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.0280 (13)</td><td rowspan="1" colspan="1">0.0419 (14)</td><td rowspan="1" colspan="1">0.0406 (15)</td><td rowspan="1" colspan="1">0.0041 (11)</td><td rowspan="1" colspan="1">0.0079 (11)</td><td rowspan="1" colspan="1">−0.0105 (12)</td></tr></table></table-wrap></sec><sec id="d1e1701" sec-type="tablewrapgeomlong"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1711"><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—C2</td><td rowspan="1" colspan="1">1.393 (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">C1—C6</td><td rowspan="1" colspan="1">1.397 (4)</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">1.757 (3)</td><td rowspan="1" colspan="1">N1—H1</td><td rowspan="1" colspan="1">0.86 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.388 (4)</td><td rowspan="1" colspan="1">N2—N3</td><td rowspan="1" colspan="1">1.395 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—H2A</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N2—H2</td><td rowspan="1" colspan="1">0.82 (4)</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.394 (5)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.386 (4)</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C11—C16</td><td rowspan="1" colspan="1">1.393 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.387 (4)</td><td rowspan="1" colspan="1">C11—S2</td><td rowspan="1" colspan="1">1.775 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.395 (4)</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.386 (4)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.377 (5)</td></tr><tr><td rowspan="1" colspan="1">C6—N1</td><td rowspan="1" colspan="1">1.393 (4)</td><td rowspan="1" colspan="1">C13—N4</td><td rowspan="1" colspan="1">1.462 (4)</td></tr><tr><td rowspan="1" colspan="1">C7—N2</td><td rowspan="1" colspan="1">1.321 (4)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.379 (5)</td></tr><tr><td rowspan="1" colspan="1">C7—N1</td><td rowspan="1" colspan="1">1.327 (4)</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—S1</td><td rowspan="1" colspan="1">1.734 (3)</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.398 (4)</td></tr><tr><td rowspan="1" colspan="1">C8—N3</td><td rowspan="1" colspan="1">1.278 (4)</td><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.499 (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">C8—C10</td><td rowspan="1" colspan="1">1.500 (4)</td><td rowspan="1" colspan="1">S2—O3</td><td rowspan="1" colspan="1">1.440 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—H9A</td><td rowspan="1" colspan="1">0.9800</td><td rowspan="1" colspan="1">S2—O1</td><td rowspan="1" colspan="1">1.463 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—H9B</td><td rowspan="1" colspan="1">0.9800</td><td rowspan="1" colspan="1">S2—O2</td><td rowspan="1" colspan="1">1.464 (2)</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—O4</td><td rowspan="1" colspan="1">1.226 (4)</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">1.227 (4)</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">C2—C1—C6</td><td rowspan="1" colspan="1">120.9 (3)</td><td rowspan="1" colspan="1">C7—N1—C6</td><td rowspan="1" colspan="1">114.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—S1</td><td rowspan="1" colspan="1">127.7 (2)</td><td rowspan="1" colspan="1">C7—N1—H1</td><td rowspan="1" colspan="1">120 (2)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—S1</td><td rowspan="1" colspan="1">111.4 (2)</td><td rowspan="1" colspan="1">C6—N1—H1</td><td rowspan="1" colspan="1">125 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">117.9 (3)</td><td rowspan="1" colspan="1">C7—N2—N3</td><td rowspan="1" colspan="1">115.8 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2A</td><td rowspan="1" colspan="1">121.0</td><td rowspan="1" colspan="1">C7—N2—H2</td><td rowspan="1" colspan="1">119 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2A</td><td rowspan="1" colspan="1">121.0</td><td rowspan="1" colspan="1">N3—N2—H2</td><td rowspan="1" colspan="1">125 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">120.9 (3)</td><td rowspan="1" colspan="1">C8—N3—N2</td><td rowspan="1" colspan="1">117.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">C7—S1—C1</td><td rowspan="1" colspan="1">89.17 (14)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">C12—C11—C16</td><td rowspan="1" colspan="1">121.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">121.3 (3)</td><td rowspan="1" colspan="1">C12—C11—S2</td><td rowspan="1" colspan="1">120.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">119.4</td><td rowspan="1" colspan="1">C16—C11—S2</td><td rowspan="1" colspan="1">118.5 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">119.4</td><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">117.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">118.0 (3)</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">121.2</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">121.0</td><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">121.2</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">121.0</td><td rowspan="1" colspan="1">C14—C13—C12</td><td rowspan="1" colspan="1">122.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—N1</td><td rowspan="1" colspan="1">127.4 (3)</td><td rowspan="1" colspan="1">C14—C13—N4</td><td rowspan="1" colspan="1">119.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C1</td><td rowspan="1" colspan="1">120.9 (3)</td><td rowspan="1" colspan="1">C12—C13—N4</td><td rowspan="1" colspan="1">118.0 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C1</td><td rowspan="1" colspan="1">111.6 (3)</td><td rowspan="1" colspan="1">C13—C14—C15</td><td rowspan="1" colspan="1">119.1 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—N1</td><td rowspan="1" colspan="1">125.2 (3)</td><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">N2—C7—S1</td><td rowspan="1" colspan="1">121.0 (2)</td><td rowspan="1" colspan="1">C15—C14—H14</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">N1—C7—S1</td><td rowspan="1" colspan="1">113.8 (2)</td><td rowspan="1" colspan="1">C14—C15—C16</td><td rowspan="1" colspan="1">120.1 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C9</td><td rowspan="1" colspan="1">126.5 (3)</td><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C10</td><td rowspan="1" colspan="1">117.1 (3)</td><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C10</td><td rowspan="1" colspan="1">116.5 (3)</td><td rowspan="1" colspan="1">C11—C16—C15</td><td rowspan="1" colspan="1">119.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9A</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C11—C16—H16</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">120.3</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—S2—O1</td><td rowspan="1" colspan="1">114.29 (12)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O3—S2—O2</td><td rowspan="1" colspan="1">113.10 (13)</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">O1—S2—O2</td><td rowspan="1" colspan="1">111.73 (12)</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">O3—S2—C11</td><td rowspan="1" colspan="1">106.88 (13)</td></tr><tr><td rowspan="1" colspan="1">C8—C10—H10A</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O1—S2—C11</td><td rowspan="1" colspan="1">105.44 (13)</td></tr><tr><td rowspan="1" colspan="1">C8—C10—H10B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O2—S2—C11</td><td rowspan="1" colspan="1">104.46 (12)</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">O4—N4—O5</td><td rowspan="1" colspan="1">124.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—C10—H10C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O4—N4—C13</td><td rowspan="1" colspan="1">118.1 (3)</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">O5—N4—C13</td><td rowspan="1" colspan="1">117.5 (3)</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"></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—C3</td><td rowspan="1" colspan="1">0.4 (4)</td><td rowspan="1" colspan="1">C2—C1—S1—C7</td><td rowspan="1" colspan="1">−179.2 (3)</td></tr><tr><td rowspan="1" colspan="1">S1—C1—C2—C3</td><td rowspan="1" colspan="1">179.9 (2)</td><td rowspan="1" colspan="1">C6—C1—S1—C7</td><td rowspan="1" colspan="1">0.4 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.4 (4)</td><td rowspan="1" colspan="1">C16—C11—C12—C13</td><td rowspan="1" colspan="1">3.0 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">−0.3 (4)</td><td rowspan="1" colspan="1">S2—C11—C12—C13</td><td rowspan="1" colspan="1">−173.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">1.0 (4)</td><td rowspan="1" colspan="1">C11—C12—C13—C14</td><td rowspan="1" colspan="1">−0.9 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—N1</td><td rowspan="1" colspan="1">−179.0 (3)</td><td rowspan="1" colspan="1">C11—C12—C13—N4</td><td rowspan="1" colspan="1">177.9 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">−1.0 (4)</td><td rowspan="1" colspan="1">C12—C13—C14—C15</td><td rowspan="1" colspan="1">−1.9 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">0.4 (4)</td><td rowspan="1" colspan="1">N4—C13—C14—C15</td><td rowspan="1" colspan="1">179.3 (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">C13—C14—C15—C16</td><td rowspan="1" colspan="1">2.6 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—N1</td><td rowspan="1" colspan="1">178.6 (2)</td><td rowspan="1" colspan="1">C12—C11—C16—C15</td><td rowspan="1" colspan="1">−2.2 (4)</td></tr><tr><td rowspan="1" colspan="1">S1—C1—C6—N1</td><td rowspan="1" colspan="1">−0.9 (3)</td><td rowspan="1" colspan="1">S2—C11—C16—C15</td><td rowspan="1" colspan="1">173.8 (2)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—N1—C6</td><td rowspan="1" colspan="1">179.5 (2)</td><td rowspan="1" colspan="1">C14—C15—C16—C11</td><td rowspan="1" colspan="1">−0.6 (4)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—N1—C6</td><td rowspan="1" colspan="1">−0.9 (3)</td><td rowspan="1" colspan="1">C12—C11—S2—O3</td><td rowspan="1" colspan="1">−118.7 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—N1—C7</td><td rowspan="1" colspan="1">179.3 (3)</td><td rowspan="1" colspan="1">C16—C11—S2—O3</td><td rowspan="1" colspan="1">65.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C6—N1—C7</td><td rowspan="1" colspan="1">1.2 (3)</td><td rowspan="1" colspan="1">C12—C11—S2—O1</td><td rowspan="1" colspan="1">3.3 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—N2—N3</td><td rowspan="1" colspan="1">−179.3 (2)</td><td rowspan="1" colspan="1">C16—C11—S2—O1</td><td rowspan="1" colspan="1">−172.8 (2)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—N2—N3</td><td rowspan="1" colspan="1">1.2 (3)</td><td rowspan="1" colspan="1">C12—C11—S2—O2</td><td rowspan="1" colspan="1">121.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—N3—N2</td><td rowspan="1" colspan="1">−0.1 (4)</td><td rowspan="1" colspan="1">C16—C11—S2—O2</td><td rowspan="1" colspan="1">−54.9 (2)</td></tr><tr><td rowspan="1" colspan="1">C10—C8—N3—N2</td><td rowspan="1" colspan="1">179.2 (2)</td><td rowspan="1" colspan="1">C14—C13—N4—O4</td><td rowspan="1" colspan="1">−154.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—N2—N3—C8</td><td rowspan="1" colspan="1">−172.8 (2)</td><td rowspan="1" colspan="1">C12—C13—N4—O4</td><td rowspan="1" colspan="1">26.4 (4)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—S1—C1</td><td rowspan="1" colspan="1">179.9 (2)</td><td rowspan="1" colspan="1">C14—C13—N4—O5</td><td rowspan="1" colspan="1">25.7 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—S1—C1</td><td rowspan="1" colspan="1">0.3 (2)</td><td rowspan="1" colspan="1">C12—C13—N4—O5</td><td rowspan="1" colspan="1">−153.2 (3)</td></tr></table></table-wrap></sec><sec id="d1e2495" sec-type="tablewraphbondslong"><label>2-[2-(Propan-2-ylidene)hydrazinyl]-1,3-benzothiazol-3-ium
3-nitrobenzenesulfonate (I) </label><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e2504"><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···O1</td><td rowspan="1" colspan="1">0.86 (4)</td><td rowspan="1" colspan="1">1.87 (4)</td><td rowspan="1" colspan="1">2.721 (3)</td><td rowspan="1" colspan="1">167 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—H2···O2</td><td rowspan="1" colspan="1">0.82 (4)</td><td rowspan="1" colspan="1">1.96 (4)</td><td rowspan="1" colspan="1">2.773 (3)</td><td rowspan="1" colspan="1">169 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—H3···O2<sup>i</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.51</td><td rowspan="1" colspan="1">3.415 (4)</td><td rowspan="1" colspan="1">160</td></tr><tr><td rowspan="1" colspan="1">C4—H4···O4<sup>ii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.55</td><td rowspan="1" colspan="1">3.292 (4)</td><td rowspan="1" colspan="1">135</td></tr><tr><td rowspan="1" colspan="1">C10—H10<italic>B</italic>···O4<sup>iii</sup></td><td rowspan="1" colspan="1">0.98</td><td rowspan="1" colspan="1">2.54</td><td rowspan="1" colspan="1">3.297 (5)</td><td rowspan="1" colspan="1">134</td></tr><tr><td rowspan="1" colspan="1">C15—H15···O3<sup>iv</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.50</td><td rowspan="1" colspan="1">3.315 (4)</td><td rowspan="1" colspan="1">144</td></tr></table></table-wrap><p>Symmetry codes: (i) <italic>x</italic>, <italic>y</italic>−1, <italic>z</italic>; (ii) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>; (iii) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>+1; (iv) <italic>x</italic>+1, <italic>y</italic>, <italic>z</italic>.</p></sec><sec id="d1e2685" sec-type="tablewrapcrystaldatalong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Crystal data</title><table-wrap position="anchor" id="d1e2694"><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>13</sub>H<sub>10</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub></td><td rowspan="1" colspan="1"><italic>Z</italic> = 4</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 350.37</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 720</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.639 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 6.83537 (15) Å</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>b</italic> = 13.5788 (3) Å</td><td rowspan="1" colspan="1">Cell parameters from 18994 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 15.6907 (4) Å</td><td rowspan="1" colspan="1">θ = 2.7–27.5°</td></tr><tr><td rowspan="1" colspan="1">α = 99.382 (2)°</td><td rowspan="1" colspan="1">µ = 0.40 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 98.2324 (19)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 100 K</td></tr><tr><td rowspan="1" colspan="1">γ = 91.9841 (19)°</td><td rowspan="1" colspan="1">Plate, yellow</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1419.55 (6) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.15 × 0.10 × 0.03 mm</td></tr></table></table-wrap></sec><sec id="d1e2819" sec-type="tablewrapdatacollectionlong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Data collection</title><table-wrap position="anchor" id="d1e2828"><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 Mercury CCD diffractometer</td><td rowspan="1" colspan="1">6033 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.018</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>FS_ABSCOR</italic>; Rigaku, 2013)</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 27.5°, θ<sub>min</sub> = 2.2°</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.861, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>h</italic> = −8→7</td></tr><tr><td rowspan="1" colspan="1">24032 measured reflections</td><td rowspan="1" colspan="1"><italic>k</italic> = −17→17</td></tr><tr><td rowspan="1" colspan="1">6465 independent reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −20→19</td></tr></table></table-wrap></sec><sec id="d1e2928" sec-type="tablewraprefinementdatalong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Refinement</title><table-wrap position="anchor" id="d1e2937"><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>)] = 0.027</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>) = 0.072</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0369<italic>P</italic>)<sup>2</sup> + 0.771<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> = 1.04</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.001</td></tr><tr><td rowspan="1" colspan="1">6465 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.40 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">427 parameters</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">0 restraints</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e3083" sec-type="specialdetails"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Special details</title><table-wrap position="anchor" id="d1e3093"><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="d1e3102" sec-type="tablewrapcoords"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e3114"><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">0.43539 (18)</td><td rowspan="1" colspan="1">0.33184 (9)</td><td rowspan="1" colspan="1">0.47102 (8)</td><td rowspan="1" colspan="1">0.0141 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.55062 (19)</td><td rowspan="1" colspan="1">0.27184 (10)</td><td rowspan="1" colspan="1">0.51978 (8)</td><td rowspan="1" colspan="1">0.0169 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3A</td><td rowspan="1" colspan="1">0.6190</td><td rowspan="1" colspan="1">0.2193</td><td rowspan="1" colspan="1">0.4915</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.5642 (2)</td><td rowspan="1" colspan="1">0.28988 (10)</td><td rowspan="1" colspan="1">0.61023 (9)</td><td rowspan="1" colspan="1">0.0202 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3B</td><td rowspan="1" colspan="1">0.6435</td><td rowspan="1" colspan="1">0.2497</td><td rowspan="1" colspan="1">0.6439</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.4627 (2)</td><td rowspan="1" colspan="1">0.36625 (11)</td><td rowspan="1" colspan="1">0.65225 (9)</td><td rowspan="1" colspan="1">0.0210 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.4751</td><td rowspan="1" colspan="1">0.3779</td><td rowspan="1" colspan="1">0.7142</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.3439 (2)</td><td rowspan="1" colspan="1">0.42538 (10)</td><td rowspan="1" colspan="1">0.60476 (8)</td><td rowspan="1" colspan="1">0.0185 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.2733</td><td rowspan="1" colspan="1">0.4767</td><td rowspan="1" colspan="1">0.6333</td><td rowspan="1" colspan="1">0.022*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.33125 (18)</td><td rowspan="1" colspan="1">0.40728 (9)</td><td rowspan="1" colspan="1">0.51429 (8)</td><td rowspan="1" colspan="1">0.0149 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.28467 (18)</td><td rowspan="1" colspan="1">0.38771 (9)</td><td rowspan="1" colspan="1">0.35588 (8)</td><td rowspan="1" colspan="1">0.0139 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">−0.12349 (18)</td><td rowspan="1" colspan="1">0.31751 (9)</td><td rowspan="1" colspan="1">0.11243 (8)</td><td rowspan="1" colspan="1">0.0140 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">−0.13679 (18)</td><td rowspan="1" colspan="1">0.36196 (9)</td><td rowspan="1" colspan="1">0.03836 (8)</td><td rowspan="1" colspan="1">0.0147 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">−0.1521</td><td rowspan="1" colspan="1">0.4317</td><td rowspan="1" colspan="1">0.0415</td><td rowspan="1" colspan="1">0.018*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">−0.12680 (18)</td><td rowspan="1" colspan="1">0.30065 (9)</td><td rowspan="1" colspan="1">−0.04025 (8)</td><td rowspan="1" colspan="1">0.0151 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">−0.10555 (19)</td><td rowspan="1" colspan="1">0.19861 (10)</td><td rowspan="1" colspan="1">−0.04774 (9)</td><td rowspan="1" colspan="1">0.0177 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">−0.1002</td><td rowspan="1" colspan="1">0.1586</td><td rowspan="1" colspan="1">−0.1029</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">−0.09235 (19)</td><td rowspan="1" colspan="1">0.15654 (10)</td><td rowspan="1" colspan="1">0.02733 (9)</td><td rowspan="1" colspan="1">0.0177 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">−0.0772</td><td rowspan="1" colspan="1">0.0868</td><td rowspan="1" colspan="1">0.0238</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">−0.10106 (18)</td><td rowspan="1" colspan="1">0.21541 (9)</td><td rowspan="1" colspan="1">0.10793 (8)</td><td rowspan="1" colspan="1">0.0161 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">−0.0918</td><td rowspan="1" colspan="1">0.1862</td><td rowspan="1" colspan="1">0.1593</td><td rowspan="1" colspan="1">0.019*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.19123 (5)</td><td rowspan="1" colspan="1">0.46708 (2)</td><td rowspan="1" colspan="1">0.43815 (2)</td><td rowspan="1" colspan="1">0.01478 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">−0.14385 (4)</td><td rowspan="1" colspan="1">0.39379 (2)</td><td rowspan="1" colspan="1">0.21312 (2)</td><td rowspan="1" colspan="1">0.01401 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.40625 (15)</td><td rowspan="1" colspan="1">0.32218 (8)</td><td rowspan="1" colspan="1">0.38016 (7)</td><td rowspan="1" colspan="1">0.0139 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.23064 (17)</td><td rowspan="1" colspan="1">0.39617 (9)</td><td rowspan="1" colspan="1">0.27112 (7)</td><td rowspan="1" colspan="1">0.0172 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.284 (3)</td><td rowspan="1" colspan="1">0.3656 (13)</td><td rowspan="1" colspan="1">0.2323 (11)</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.07391 (16)</td><td rowspan="1" colspan="1">0.45532 (8)</td><td rowspan="1" colspan="1">0.25127 (7)</td><td rowspan="1" colspan="1">0.0156 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.101 (2)</td><td rowspan="1" colspan="1">0.4983 (13)</td><td rowspan="1" colspan="1">0.2204 (11)</td><td rowspan="1" colspan="1">0.019*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">−0.14030 (17)</td><td rowspan="1" colspan="1">0.34643 (8)</td><td rowspan="1" colspan="1">−0.11915 (7)</td><td rowspan="1" colspan="1">0.0180 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">−0.27389 (14)</td><td rowspan="1" colspan="1">0.47084 (7)</td><td rowspan="1" colspan="1">0.19593 (6)</td><td rowspan="1" colspan="1">0.01904 (19)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">−0.17746 (14)</td><td rowspan="1" colspan="1">0.32943 (7)</td><td rowspan="1" colspan="1">0.27375 (6)</td><td rowspan="1" colspan="1">0.01830 (19)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">−0.15792 (16)</td><td rowspan="1" colspan="1">0.43763 (7)</td><td rowspan="1" colspan="1">−0.11068 (6)</td><td rowspan="1" colspan="1">0.0248 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">−0.13227 (18)</td><td rowspan="1" colspan="1">0.29368 (8)</td><td rowspan="1" colspan="1">−0.18884 (6)</td><td rowspan="1" colspan="1">0.0306 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.38706 (17)</td><td rowspan="1" colspan="1">0.27186 (9)</td><td rowspan="1" colspan="1">0.04845 (8)</td><td rowspan="1" colspan="1">0.0135 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.37430 (18)</td><td rowspan="1" colspan="1">0.35578 (10)</td><td rowspan="1" colspan="1">0.00746 (8)</td><td rowspan="1" colspan="1">0.0162 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.3734</td><td rowspan="1" colspan="1">0.4208</td><td rowspan="1" colspan="1">0.0407</td><td rowspan="1" colspan="1">0.019*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.36290 (19)</td><td rowspan="1" colspan="1">0.34242 (10)</td><td rowspan="1" colspan="1">−0.08280 (9)</td><td rowspan="1" colspan="1">0.0188 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.3550</td><td rowspan="1" colspan="1">0.3990</td><td rowspan="1" colspan="1">−0.1114</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.3629 (2)</td><td rowspan="1" colspan="1">0.24711 (10)</td><td rowspan="1" colspan="1">−0.13217 (9)</td><td rowspan="1" colspan="1">0.0203 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17</td><td rowspan="1" colspan="1">0.3535</td><td rowspan="1" colspan="1">0.2398</td><td rowspan="1" colspan="1">−0.1939</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.3765 (2)</td><td rowspan="1" colspan="1">0.16275 (10)</td><td rowspan="1" colspan="1">−0.09252 (8)</td><td rowspan="1" colspan="1">0.0183 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">0.3766</td><td rowspan="1" colspan="1">0.0979</td><td rowspan="1" colspan="1">−0.1261</td><td rowspan="1" colspan="1">0.022*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.38981 (18)</td><td rowspan="1" colspan="1">0.17643 (9)</td><td rowspan="1" colspan="1">−0.00197 (8)</td><td rowspan="1" colspan="1">0.0146 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.40680 (18)</td><td rowspan="1" colspan="1">0.18334 (9)</td><td rowspan="1" colspan="1">0.15515 (8)</td><td rowspan="1" colspan="1">0.0139 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.15315 (19)</td><td rowspan="1" colspan="1">0.07929 (9)</td><td rowspan="1" colspan="1">0.36629 (8)</td><td rowspan="1" colspan="1">0.0163 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.22077 (19)</td><td rowspan="1" colspan="1">0.04559 (10)</td><td rowspan="1" colspan="1">0.44344 (8)</td><td rowspan="1" colspan="1">0.0165 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H22</td><td rowspan="1" colspan="1">0.2967</td><td rowspan="1" colspan="1">−0.0117</td><td rowspan="1" colspan="1">0.4438</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.17295 (19)</td><td rowspan="1" colspan="1">0.09898 (10)</td><td rowspan="1" colspan="1">0.51990 (8)</td><td rowspan="1" colspan="1">0.0175 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C24</td><td rowspan="1" colspan="1">0.0642 (2)</td><td rowspan="1" colspan="1">0.18347 (10)</td><td rowspan="1" colspan="1">0.52236 (9)</td><td rowspan="1" colspan="1">0.0205 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H24</td><td rowspan="1" colspan="1">0.0348</td><td rowspan="1" colspan="1">0.2185</td><td rowspan="1" colspan="1">0.5761</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">−0.0005 (2)</td><td rowspan="1" colspan="1">0.21522 (10)</td><td rowspan="1" colspan="1">0.44401 (10)</td><td rowspan="1" colspan="1">0.0211 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25</td><td rowspan="1" colspan="1">−0.0747</td><td rowspan="1" colspan="1">0.2731</td><td rowspan="1" colspan="1">0.4439</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C26</td><td rowspan="1" colspan="1">0.0421 (2)</td><td rowspan="1" colspan="1">0.16336 (10)</td><td rowspan="1" colspan="1">0.36575 (9)</td><td rowspan="1" colspan="1">0.0190 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H26</td><td rowspan="1" colspan="1">−0.0042</td><td rowspan="1" colspan="1">0.1850</td><td rowspan="1" colspan="1">0.3122</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S3</td><td rowspan="1" colspan="1">0.40564 (5)</td><td rowspan="1" colspan="1">0.08651 (2)</td><td rowspan="1" colspan="1">0.06631 (2)</td><td rowspan="1" colspan="1">0.01512 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S4</td><td rowspan="1" colspan="1">0.21030 (5)</td><td rowspan="1" colspan="1">0.01172 (2)</td><td rowspan="1" colspan="1">0.26734 (2)</td><td rowspan="1" colspan="1">0.01740 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.39616 (15)</td><td rowspan="1" colspan="1">0.27357 (8)</td><td rowspan="1" colspan="1">0.13792 (7)</td><td rowspan="1" colspan="1">0.0136 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.41743 (18)</td><td rowspan="1" colspan="1">0.16301 (8)</td><td rowspan="1" colspan="1">0.23735 (7)</td><td rowspan="1" colspan="1">0.0184 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6</td><td rowspan="1" colspan="1">0.430 (2)</td><td rowspan="1" colspan="1">0.2085 (13)</td><td rowspan="1" colspan="1">0.2795 (12)</td><td rowspan="1" colspan="1">0.022*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.42029 (17)</td><td rowspan="1" colspan="1">0.06345 (8)</td><td rowspan="1" colspan="1">0.24827 (7)</td><td rowspan="1" colspan="1">0.0170 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.520 (3)</td><td rowspan="1" colspan="1">0.0496 (12)</td><td rowspan="1" colspan="1">0.2847 (11)</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N8</td><td rowspan="1" colspan="1">0.23973 (17)</td><td rowspan="1" colspan="1">0.06263 (9)</td><td rowspan="1" colspan="1">0.60183 (7)</td><td rowspan="1" colspan="1">0.0205 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.26067 (17)</td><td rowspan="1" colspan="1">−0.08604 (7)</td><td rowspan="1" colspan="1">0.28157 (6)</td><td rowspan="1" colspan="1">0.0248 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O6</td><td rowspan="1" colspan="1">0.05911 (15)</td><td rowspan="1" colspan="1">0.02700 (8)</td><td rowspan="1" colspan="1">0.19880 (6)</td><td rowspan="1" colspan="1">0.0242 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O7</td><td rowspan="1" colspan="1">0.32765 (15)</td><td rowspan="1" colspan="1">−0.01577 (8)</td><td rowspan="1" colspan="1">0.59683 (7)</td><td rowspan="1" colspan="1">0.0260 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O8</td><td rowspan="1" colspan="1">0.20339 (17)</td><td rowspan="1" colspan="1">0.10970 (9)</td><td rowspan="1" colspan="1">0.67020 (7)</td><td rowspan="1" colspan="1">0.0312 (2)</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e4006" sec-type="tablewrapadps"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e4018"><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">0.0141 (6)</td><td rowspan="1" colspan="1">0.0152 (6)</td><td rowspan="1" colspan="1">0.0123 (6)</td><td rowspan="1" colspan="1">−0.0026 (4)</td><td rowspan="1" colspan="1">0.0022 (4)</td><td rowspan="1" colspan="1">0.0005 (4)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0156 (6)</td><td rowspan="1" colspan="1">0.0167 (6)</td><td rowspan="1" colspan="1">0.0180 (6)</td><td rowspan="1" colspan="1">0.0007 (5)</td><td rowspan="1" colspan="1">0.0022 (5)</td><td rowspan="1" colspan="1">0.0023 (5)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0207 (6)</td><td rowspan="1" colspan="1">0.0218 (7)</td><td rowspan="1" colspan="1">0.0186 (6)</td><td rowspan="1" colspan="1">0.0001 (5)</td><td rowspan="1" colspan="1">0.0000 (5)</td><td rowspan="1" colspan="1">0.0076 (5)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0248 (7)</td><td rowspan="1" colspan="1">0.0256 (7)</td><td rowspan="1" colspan="1">0.0121 (6)</td><td rowspan="1" colspan="1">−0.0011 (5)</td><td rowspan="1" colspan="1">0.0017 (5)</td><td rowspan="1" colspan="1">0.0035 (5)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0211 (6)</td><td rowspan="1" colspan="1">0.0208 (6)</td><td rowspan="1" colspan="1">0.0131 (6)</td><td rowspan="1" colspan="1">0.0011 (5)</td><td rowspan="1" colspan="1">0.0044 (5)</td><td rowspan="1" colspan="1">0.0002 (5)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0143 (6)</td><td rowspan="1" colspan="1">0.0166 (6)</td><td rowspan="1" colspan="1">0.0132 (6)</td><td rowspan="1" colspan="1">−0.0002 (4)</td><td rowspan="1" colspan="1">0.0011 (4)</td><td rowspan="1" colspan="1">0.0019 (5)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0145 (6)</td><td rowspan="1" colspan="1">0.0142 (6)</td><td rowspan="1" colspan="1">0.0124 (6)</td><td rowspan="1" colspan="1">−0.0014 (4)</td><td rowspan="1" colspan="1">0.0039 (4)</td><td rowspan="1" colspan="1">−0.0006 (4)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0135 (5)</td><td rowspan="1" colspan="1">0.0154 (6)</td><td rowspan="1" colspan="1">0.0120 (6)</td><td rowspan="1" colspan="1">0.0018 (4)</td><td rowspan="1" colspan="1">0.0007 (4)</td><td rowspan="1" colspan="1">0.0005 (4)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0150 (6)</td><td rowspan="1" colspan="1">0.0146 (6)</td><td rowspan="1" colspan="1">0.0139 (6)</td><td rowspan="1" colspan="1">0.0004 (4)</td><td rowspan="1" colspan="1">0.0014 (4)</td><td rowspan="1" colspan="1">0.0016 (5)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0142 (6)</td><td rowspan="1" colspan="1">0.0177 (6)</td><td rowspan="1" colspan="1">0.0130 (6)</td><td rowspan="1" colspan="1">−0.0006 (4)</td><td rowspan="1" colspan="1">0.0008 (4)</td><td rowspan="1" colspan="1">0.0025 (5)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0160 (6)</td><td rowspan="1" colspan="1">0.0173 (6)</td><td rowspan="1" colspan="1">0.0175 (6)</td><td rowspan="1" colspan="1">−0.0001 (5)</td><td rowspan="1" colspan="1">0.0012 (5)</td><td rowspan="1" colspan="1">−0.0028 (5)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0177 (6)</td><td rowspan="1" colspan="1">0.0131 (6)</td><td rowspan="1" colspan="1">0.0211 (6)</td><td rowspan="1" colspan="1">0.0012 (5)</td><td rowspan="1" colspan="1">0.0006 (5)</td><td rowspan="1" colspan="1">0.0011 (5)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0152 (6)</td><td rowspan="1" colspan="1">0.0164 (6)</td><td rowspan="1" colspan="1">0.0166 (6)</td><td rowspan="1" colspan="1">0.0012 (5)</td><td rowspan="1" colspan="1">0.0001 (5)</td><td rowspan="1" colspan="1">0.0043 (5)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.01749 (15)</td><td rowspan="1" colspan="1">0.01571 (15)</td><td rowspan="1" colspan="1">0.01076 (14)</td><td rowspan="1" colspan="1">0.00315 (11)</td><td rowspan="1" colspan="1">0.00279 (11)</td><td rowspan="1" colspan="1">0.00015 (11)</td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">0.01745 (15)</td><td rowspan="1" colspan="1">0.01462 (14)</td><td rowspan="1" colspan="1">0.01033 (14)</td><td rowspan="1" colspan="1">0.00364 (11)</td><td rowspan="1" colspan="1">0.00230 (11)</td><td rowspan="1" colspan="1">0.00244 (11)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0147 (5)</td><td rowspan="1" colspan="1">0.0151 (5)</td><td rowspan="1" colspan="1">0.0114 (5)</td><td rowspan="1" colspan="1">−0.0002 (4)</td><td rowspan="1" colspan="1">0.0026 (4)</td><td rowspan="1" colspan="1">0.0005 (4)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0186 (5)</td><td rowspan="1" colspan="1">0.0224 (6)</td><td rowspan="1" colspan="1">0.0106 (5)</td><td rowspan="1" colspan="1">0.0069 (4)</td><td rowspan="1" colspan="1">0.0035 (4)</td><td rowspan="1" colspan="1">0.0004 (4)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0193 (5)</td><td rowspan="1" colspan="1">0.0144 (5)</td><td rowspan="1" colspan="1">0.0130 (5)</td><td rowspan="1" colspan="1">0.0019 (4)</td><td rowspan="1" colspan="1">0.0015 (4)</td><td rowspan="1" colspan="1">0.0030 (4)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0196 (5)</td><td rowspan="1" colspan="1">0.0212 (6)</td><td rowspan="1" colspan="1">0.0126 (5)</td><td rowspan="1" colspan="1">−0.0015 (4)</td><td rowspan="1" colspan="1">0.0015 (4)</td><td rowspan="1" colspan="1">0.0017 (4)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0238 (5)</td><td rowspan="1" colspan="1">0.0196 (5)</td><td rowspan="1" colspan="1">0.0145 (4)</td><td rowspan="1" colspan="1">0.0093 (4)</td><td rowspan="1" colspan="1">0.0029 (4)</td><td rowspan="1" colspan="1">0.0032 (4)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0222 (5)</td><td rowspan="1" colspan="1">0.0197 (5)</td><td rowspan="1" colspan="1">0.0144 (4)</td><td rowspan="1" colspan="1">0.0023 (4)</td><td rowspan="1" colspan="1">0.0039 (4)</td><td rowspan="1" colspan="1">0.0057 (4)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0390 (6)</td><td rowspan="1" colspan="1">0.0192 (5)</td><td rowspan="1" colspan="1">0.0181 (5)</td><td rowspan="1" colspan="1">0.0015 (4)</td><td rowspan="1" colspan="1">0.0069 (4)</td><td rowspan="1" colspan="1">0.0060 (4)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0487 (7)</td><td rowspan="1" colspan="1">0.0290 (6)</td><td rowspan="1" colspan="1">0.0116 (5)</td><td rowspan="1" colspan="1">0.0004 (5)</td><td rowspan="1" colspan="1">0.0035 (4)</td><td rowspan="1" colspan="1">−0.0022 (4)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0113 (5)</td><td rowspan="1" colspan="1">0.0162 (6)</td><td rowspan="1" colspan="1">0.0131 (6)</td><td rowspan="1" colspan="1">0.0016 (4)</td><td rowspan="1" colspan="1">0.0024 (4)</td><td rowspan="1" colspan="1">0.0018 (5)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0151 (6)</td><td rowspan="1" colspan="1">0.0158 (6)</td><td rowspan="1" colspan="1">0.0176 (6)</td><td rowspan="1" colspan="1">0.0016 (4)</td><td rowspan="1" colspan="1">0.0020 (5)</td><td rowspan="1" colspan="1">0.0033 (5)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0187 (6)</td><td rowspan="1" colspan="1">0.0206 (6)</td><td rowspan="1" colspan="1">0.0186 (6)</td><td rowspan="1" colspan="1">0.0025 (5)</td><td rowspan="1" colspan="1">0.0018 (5)</td><td rowspan="1" colspan="1">0.0087 (5)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0223 (7)</td><td rowspan="1" colspan="1">0.0265 (7)</td><td rowspan="1" colspan="1">0.0126 (6)</td><td rowspan="1" colspan="1">0.0026 (5)</td><td rowspan="1" colspan="1">0.0014 (5)</td><td rowspan="1" colspan="1">0.0050 (5)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0226 (6)</td><td rowspan="1" colspan="1">0.0187 (6)</td><td rowspan="1" colspan="1">0.0136 (6)</td><td rowspan="1" colspan="1">0.0038 (5)</td><td rowspan="1" colspan="1">0.0031 (5)</td><td rowspan="1" colspan="1">0.0015 (5)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.0152 (6)</td><td rowspan="1" colspan="1">0.0151 (6)</td><td rowspan="1" colspan="1">0.0138 (6)</td><td rowspan="1" colspan="1">0.0025 (4)</td><td rowspan="1" colspan="1">0.0019 (4)</td><td rowspan="1" colspan="1">0.0036 (5)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.0145 (6)</td><td rowspan="1" colspan="1">0.0146 (6)</td><td rowspan="1" colspan="1">0.0121 (6)</td><td rowspan="1" colspan="1">0.0007 (4)</td><td rowspan="1" colspan="1">0.0030 (4)</td><td rowspan="1" colspan="1">0.0003 (4)</td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.0192 (6)</td><td rowspan="1" colspan="1">0.0151 (6)</td><td rowspan="1" colspan="1">0.0147 (6)</td><td rowspan="1" colspan="1">−0.0028 (5)</td><td rowspan="1" colspan="1">0.0037 (5)</td><td rowspan="1" colspan="1">0.0025 (5)</td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.0169 (6)</td><td rowspan="1" colspan="1">0.0154 (6)</td><td rowspan="1" colspan="1">0.0174 (6)</td><td rowspan="1" colspan="1">−0.0023 (5)</td><td rowspan="1" colspan="1">0.0026 (5)</td><td rowspan="1" colspan="1">0.0040 (5)</td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.0175 (6)</td><td rowspan="1" colspan="1">0.0196 (6)</td><td rowspan="1" colspan="1">0.0156 (6)</td><td rowspan="1" colspan="1">−0.0048 (5)</td><td rowspan="1" colspan="1">0.0026 (5)</td><td rowspan="1" colspan="1">0.0042 (5)</td></tr><tr><td rowspan="1" colspan="1">C24</td><td rowspan="1" colspan="1">0.0202 (6)</td><td rowspan="1" colspan="1">0.0195 (6)</td><td rowspan="1" colspan="1">0.0218 (7)</td><td rowspan="1" colspan="1">−0.0041 (5)</td><td rowspan="1" colspan="1">0.0082 (5)</td><td rowspan="1" colspan="1">0.0000 (5)</td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.0202 (6)</td><td rowspan="1" colspan="1">0.0161 (6)</td><td rowspan="1" colspan="1">0.0290 (7)</td><td rowspan="1" colspan="1">0.0001 (5)</td><td rowspan="1" colspan="1">0.0080 (5)</td><td rowspan="1" colspan="1">0.0058 (5)</td></tr><tr><td rowspan="1" colspan="1">C26</td><td rowspan="1" colspan="1">0.0197 (6)</td><td rowspan="1" colspan="1">0.0175 (6)</td><td rowspan="1" colspan="1">0.0212 (7)</td><td rowspan="1" colspan="1">−0.0008 (5)</td><td rowspan="1" colspan="1">0.0035 (5)</td><td rowspan="1" colspan="1">0.0078 (5)</td></tr><tr><td rowspan="1" colspan="1">S3</td><td rowspan="1" colspan="1">0.02245 (16)</td><td rowspan="1" colspan="1">0.01240 (14)</td><td rowspan="1" colspan="1">0.01072 (14)</td><td rowspan="1" colspan="1">0.00307 (11)</td><td rowspan="1" colspan="1">0.00390 (11)</td><td rowspan="1" colspan="1">0.00095 (11)</td></tr><tr><td rowspan="1" colspan="1">S4</td><td rowspan="1" colspan="1">0.02582 (17)</td><td rowspan="1" colspan="1">0.01316 (15)</td><td rowspan="1" colspan="1">0.01286 (15)</td><td rowspan="1" colspan="1">−0.00091 (12)</td><td rowspan="1" colspan="1">0.00193 (12)</td><td rowspan="1" colspan="1">0.00245 (11)</td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.0158 (5)</td><td rowspan="1" colspan="1">0.0131 (5)</td><td rowspan="1" colspan="1">0.0118 (5)</td><td rowspan="1" colspan="1">0.0008 (4)</td><td rowspan="1" colspan="1">0.0029 (4)</td><td rowspan="1" colspan="1">0.0009 (4)</td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.0332 (6)</td><td rowspan="1" colspan="1">0.0112 (5)</td><td rowspan="1" colspan="1">0.0108 (5)</td><td rowspan="1" colspan="1">−0.0002 (4)</td><td rowspan="1" colspan="1">0.0048 (4)</td><td rowspan="1" colspan="1">0.0009 (4)</td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.0238 (6)</td><td rowspan="1" colspan="1">0.0146 (5)</td><td rowspan="1" colspan="1">0.0135 (5)</td><td rowspan="1" colspan="1">0.0035 (4)</td><td rowspan="1" colspan="1">0.0034 (4)</td><td rowspan="1" colspan="1">0.0039 (4)</td></tr><tr><td rowspan="1" colspan="1">N8</td><td rowspan="1" colspan="1">0.0198 (5)</td><td rowspan="1" colspan="1">0.0257 (6)</td><td rowspan="1" colspan="1">0.0152 (5)</td><td rowspan="1" colspan="1">−0.0052 (5)</td><td rowspan="1" colspan="1">0.0021 (4)</td><td rowspan="1" colspan="1">0.0030 (4)</td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.0423 (6)</td><td rowspan="1" colspan="1">0.0128 (4)</td><td rowspan="1" colspan="1">0.0197 (5)</td><td rowspan="1" colspan="1">0.0008 (4)</td><td rowspan="1" colspan="1">0.0056 (4)</td><td rowspan="1" colspan="1">0.0035 (4)</td></tr><tr><td rowspan="1" colspan="1">O6</td><td rowspan="1" colspan="1">0.0283 (5)</td><td rowspan="1" colspan="1">0.0252 (5)</td><td rowspan="1" colspan="1">0.0171 (5)</td><td rowspan="1" colspan="1">−0.0024 (4)</td><td rowspan="1" colspan="1">−0.0020 (4)</td><td rowspan="1" colspan="1">0.0038 (4)</td></tr><tr><td rowspan="1" colspan="1">O7</td><td rowspan="1" colspan="1">0.0274 (5)</td><td rowspan="1" colspan="1">0.0324 (6)</td><td rowspan="1" colspan="1">0.0192 (5)</td><td rowspan="1" colspan="1">0.0041 (4)</td><td rowspan="1" colspan="1">0.0015 (4)</td><td rowspan="1" colspan="1">0.0090 (4)</td></tr><tr><td rowspan="1" colspan="1">O8</td><td rowspan="1" colspan="1">0.0406 (6)</td><td rowspan="1" colspan="1">0.0368 (6)</td><td rowspan="1" colspan="1">0.0148 (5)</td><td rowspan="1" colspan="1">−0.0036 (5)</td><td rowspan="1" colspan="1">0.0069 (4)</td><td rowspan="1" colspan="1">−0.0009 (4)</td></tr></table></table-wrap></sec><sec id="d1e4792" sec-type="tablewrapgeomlong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e4802"><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—C2</td><td rowspan="1" colspan="1">1.3944 (18)</td><td rowspan="1" colspan="1">C14—N5</td><td rowspan="1" colspan="1">1.3927 (16)</td></tr><tr><td rowspan="1" colspan="1">C1—N1</td><td rowspan="1" colspan="1">1.3947 (16)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.3963 (17)</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.4068 (17)</td><td rowspan="1" colspan="1">C14—C19</td><td rowspan="1" colspan="1">1.4061 (17)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.3894 (19)</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.3887 (18)</td></tr><tr><td rowspan="1" colspan="1">C2—H3A</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.396 (2)</td><td rowspan="1" colspan="1">C16—C17</td><td rowspan="1" colspan="1">1.3958 (19)</td></tr><tr><td rowspan="1" colspan="1">C3—H3B</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.3877 (19)</td><td rowspan="1" colspan="1">C17—C18</td><td rowspan="1" colspan="1">1.3895 (19)</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C17—H17</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.3902 (17)</td><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.3918 (18)</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C6—S1</td><td rowspan="1" colspan="1">1.7450 (13)</td><td rowspan="1" colspan="1">C19—S3</td><td rowspan="1" colspan="1">1.7473 (13)</td></tr><tr><td rowspan="1" colspan="1">C7—N1</td><td rowspan="1" colspan="1">1.3033 (16)</td><td rowspan="1" colspan="1">C20—N5</td><td rowspan="1" colspan="1">1.2992 (16)</td></tr><tr><td rowspan="1" colspan="1">C7—N2</td><td rowspan="1" colspan="1">1.3529 (16)</td><td rowspan="1" colspan="1">C20—N6</td><td rowspan="1" colspan="1">1.3549 (16)</td></tr><tr><td rowspan="1" colspan="1">C7—S1</td><td rowspan="1" colspan="1">1.7511 (12)</td><td rowspan="1" colspan="1">C20—S3</td><td rowspan="1" colspan="1">1.7522 (12)</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.3876 (17)</td><td rowspan="1" colspan="1">C21—C22</td><td rowspan="1" colspan="1">1.3869 (18)</td></tr><tr><td rowspan="1" colspan="1">C8—C13</td><td rowspan="1" colspan="1">1.3917 (17)</td><td rowspan="1" colspan="1">C21—C26</td><td rowspan="1" colspan="1">1.3934 (18)</td></tr><tr><td rowspan="1" colspan="1">C8—S2</td><td rowspan="1" colspan="1">1.7685 (12)</td><td rowspan="1" colspan="1">C21—S4</td><td rowspan="1" colspan="1">1.7717 (13)</td></tr><tr><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.3829 (17)</td><td rowspan="1" colspan="1">C22—C23</td><td rowspan="1" colspan="1">1.3846 (18)</td></tr><tr><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C22—H22</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.3858 (18)</td><td rowspan="1" colspan="1">C23—C24</td><td rowspan="1" colspan="1">1.3868 (19)</td></tr><tr><td rowspan="1" colspan="1">C10—N4</td><td rowspan="1" colspan="1">1.4661 (16)</td><td rowspan="1" colspan="1">C23—N8</td><td rowspan="1" colspan="1">1.4693 (17)</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.3837 (19)</td><td rowspan="1" colspan="1">C24—C25</td><td rowspan="1" colspan="1">1.387 (2)</td></tr><tr><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C24—H24</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.3918 (18)</td><td rowspan="1" colspan="1">C25—C26</td><td rowspan="1" colspan="1">1.387 (2)</td></tr><tr><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C25—H25</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C26—H26</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">S2—O2</td><td rowspan="1" colspan="1">1.4287 (9)</td><td rowspan="1" colspan="1">S4—O5</td><td rowspan="1" colspan="1">1.4271 (10)</td></tr><tr><td rowspan="1" colspan="1">S2—O1</td><td rowspan="1" colspan="1">1.4301 (9)</td><td rowspan="1" colspan="1">S4—O6</td><td rowspan="1" colspan="1">1.4272 (10)</td></tr><tr><td rowspan="1" colspan="1">S2—N3</td><td rowspan="1" colspan="1">1.6636 (11)</td><td rowspan="1" colspan="1">S4—N7</td><td rowspan="1" colspan="1">1.6628 (12)</td></tr><tr><td rowspan="1" colspan="1">N2—N3</td><td rowspan="1" colspan="1">1.3912 (15)</td><td rowspan="1" colspan="1">N6—N7</td><td rowspan="1" colspan="1">1.3906 (15)</td></tr><tr><td rowspan="1" colspan="1">N2—H2</td><td rowspan="1" colspan="1">0.816 (18)</td><td rowspan="1" colspan="1">N6—H6</td><td rowspan="1" colspan="1">0.820 (18)</td></tr><tr><td rowspan="1" colspan="1">N3—H3</td><td rowspan="1" colspan="1">0.848 (17)</td><td rowspan="1" colspan="1">N7—H7</td><td rowspan="1" colspan="1">0.871 (17)</td></tr><tr><td rowspan="1" colspan="1">N4—O4</td><td rowspan="1" colspan="1">1.2150 (15)</td><td rowspan="1" colspan="1">N8—O8</td><td rowspan="1" colspan="1">1.2186 (16)</td></tr><tr><td rowspan="1" colspan="1">N4—O3</td><td rowspan="1" colspan="1">1.2358 (15)</td><td rowspan="1" colspan="1">N8—O7</td><td rowspan="1" colspan="1">1.2374 (16)</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">C2—C1—N1</td><td rowspan="1" colspan="1">125.63 (11)</td><td rowspan="1" colspan="1">N5—C14—C15</td><td rowspan="1" colspan="1">125.14 (11)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6</td><td rowspan="1" colspan="1">119.30 (11)</td><td rowspan="1" colspan="1">N5—C14—C19</td><td rowspan="1" colspan="1">115.21 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6</td><td rowspan="1" colspan="1">115.02 (11)</td><td rowspan="1" colspan="1">C15—C14—C19</td><td rowspan="1" colspan="1">119.65 (11)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">119.12 (12)</td><td rowspan="1" colspan="1">C16—C15—C14</td><td rowspan="1" colspan="1">118.75 (12)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H3A</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">120.6</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H3A</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">120.6</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">120.83 (12)</td><td rowspan="1" colspan="1">C15—C16—C17</td><td rowspan="1" colspan="1">120.99 (12)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3B</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3B</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">C17—C16—H16</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">120.91 (12)</td><td rowspan="1" colspan="1">C18—C17—C16</td><td rowspan="1" colspan="1">121.09 (12)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">119.5</td><td rowspan="1" colspan="1">C18—C17—H17</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">119.5</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">C4—C5—C6</td><td rowspan="1" colspan="1">118.08 (12)</td><td rowspan="1" colspan="1">C17—C18—C19</td><td rowspan="1" colspan="1">117.81 (12)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">121.0</td><td rowspan="1" colspan="1">C17—C18—H18</td><td rowspan="1" colspan="1">121.1</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">121.0</td><td rowspan="1" colspan="1">C19—C18—H18</td><td rowspan="1" colspan="1">121.1</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C1</td><td rowspan="1" colspan="1">121.74 (12)</td><td rowspan="1" colspan="1">C18—C19—C14</td><td rowspan="1" colspan="1">121.70 (12)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—S1</td><td rowspan="1" colspan="1">128.32 (10)</td><td rowspan="1" colspan="1">C18—C19—S3</td><td rowspan="1" colspan="1">128.77 (10)</td></tr><tr><td rowspan="1" colspan="1">C1—C6—S1</td><td rowspan="1" colspan="1">109.93 (9)</td><td rowspan="1" colspan="1">C14—C19—S3</td><td rowspan="1" colspan="1">109.51 (9)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—N2</td><td rowspan="1" colspan="1">122.68 (11)</td><td rowspan="1" colspan="1">N5—C20—N6</td><td rowspan="1" colspan="1">122.64 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—S1</td><td rowspan="1" colspan="1">117.31 (9)</td><td rowspan="1" colspan="1">N5—C20—S3</td><td rowspan="1" colspan="1">116.93 (9)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—S1</td><td rowspan="1" colspan="1">120.01 (10)</td><td rowspan="1" colspan="1">N6—C20—S3</td><td rowspan="1" colspan="1">120.43 (9)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C13</td><td rowspan="1" colspan="1">121.44 (11)</td><td rowspan="1" colspan="1">C22—C21—C26</td><td rowspan="1" colspan="1">121.43 (12)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2</td><td rowspan="1" colspan="1">118.05 (9)</td><td rowspan="1" colspan="1">C22—C21—S4</td><td rowspan="1" colspan="1">118.12 (10)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2</td><td rowspan="1" colspan="1">120.47 (10)</td><td rowspan="1" colspan="1">C26—C21—S4</td><td rowspan="1" colspan="1">120.45 (10)</td></tr><tr><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">117.29 (11)</td><td rowspan="1" colspan="1">C23—C22—C21</td><td rowspan="1" colspan="1">117.16 (12)</td></tr><tr><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C23—C22—H22</td><td rowspan="1" colspan="1">121.4</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C21—C22—H22</td><td rowspan="1" colspan="1">121.4</td></tr><tr><td rowspan="1" colspan="1">C9—C10—C11</td><td rowspan="1" colspan="1">123.15 (12)</td><td rowspan="1" colspan="1">C22—C23—C24</td><td rowspan="1" colspan="1">123.27 (12)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—N4</td><td rowspan="1" colspan="1">118.01 (11)</td><td rowspan="1" colspan="1">C22—C23—N8</td><td rowspan="1" colspan="1">117.66 (12)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—N4</td><td rowspan="1" colspan="1">118.84 (11)</td><td rowspan="1" colspan="1">C24—C23—N8</td><td rowspan="1" colspan="1">119.07 (12)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C10</td><td rowspan="1" colspan="1">118.18 (12)</td><td rowspan="1" colspan="1">C25—C24—C23</td><td rowspan="1" colspan="1">118.01 (13)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.9</td><td rowspan="1" colspan="1">C25—C24—H24</td><td rowspan="1" colspan="1">121.0</td></tr><tr><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.9</td><td rowspan="1" colspan="1">C23—C24—H24</td><td rowspan="1" colspan="1">121.0</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">120.65 (12)</td><td rowspan="1" colspan="1">C26—C25—C24</td><td rowspan="1" colspan="1">120.68 (13)</td></tr><tr><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">119.7</td><td rowspan="1" colspan="1">C26—C25—H25</td><td rowspan="1" colspan="1">119.7</td></tr><tr><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">119.7</td><td rowspan="1" colspan="1">C24—C25—H25</td><td rowspan="1" colspan="1">119.7</td></tr><tr><td rowspan="1" colspan="1">C8—C13—C12</td><td rowspan="1" colspan="1">119.28 (12)</td><td rowspan="1" colspan="1">C25—C26—C21</td><td rowspan="1" colspan="1">119.45 (12)</td></tr><tr><td rowspan="1" colspan="1">C8—C13—H13</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C25—C26—H26</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C21—C26—H26</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C6—S1—C7</td><td rowspan="1" colspan="1">88.04 (6)</td><td rowspan="1" colspan="1">C19—S3—C20</td><td rowspan="1" colspan="1">88.30 (6)</td></tr><tr><td rowspan="1" colspan="1">O2—S2—O1</td><td rowspan="1" colspan="1">121.70 (6)</td><td rowspan="1" colspan="1">O5—S4—O6</td><td rowspan="1" colspan="1">121.88 (6)</td></tr><tr><td rowspan="1" colspan="1">O2—S2—N3</td><td rowspan="1" colspan="1">106.58 (6)</td><td rowspan="1" colspan="1">O5—S4—N7</td><td rowspan="1" colspan="1">103.87 (6)</td></tr><tr><td rowspan="1" colspan="1">O1—S2—N3</td><td rowspan="1" colspan="1">103.87 (6)</td><td rowspan="1" colspan="1">O6—S4—N7</td><td rowspan="1" colspan="1">106.93 (6)</td></tr><tr><td rowspan="1" colspan="1">O2—S2—C8</td><td rowspan="1" colspan="1">107.73 (6)</td><td rowspan="1" colspan="1">O5—S4—C21</td><td rowspan="1" colspan="1">108.35 (6)</td></tr><tr><td rowspan="1" colspan="1">O1—S2—C8</td><td rowspan="1" colspan="1">108.20 (6)</td><td rowspan="1" colspan="1">O6—S4—C21</td><td rowspan="1" colspan="1">107.54 (6)</td></tr><tr><td rowspan="1" colspan="1">N3—S2—C8</td><td rowspan="1" colspan="1">108.09 (6)</td><td rowspan="1" colspan="1">N7—S4—C21</td><td rowspan="1" colspan="1">107.49 (6)</td></tr><tr><td rowspan="1" colspan="1">C7—N1—C1</td><td rowspan="1" colspan="1">109.69 (10)</td><td rowspan="1" colspan="1">C20—N5—C14</td><td rowspan="1" colspan="1">110.05 (10)</td></tr><tr><td rowspan="1" colspan="1">C7—N2—N3</td><td rowspan="1" colspan="1">117.74 (11)</td><td rowspan="1" colspan="1">C20—N6—N7</td><td rowspan="1" colspan="1">118.05 (11)</td></tr><tr><td rowspan="1" colspan="1">C7—N2—H2</td><td rowspan="1" colspan="1">121.7 (12)</td><td rowspan="1" colspan="1">C20—N6—H6</td><td rowspan="1" colspan="1">120.6 (12)</td></tr><tr><td rowspan="1" colspan="1">N3—N2—H2</td><td rowspan="1" colspan="1">120.5 (12)</td><td rowspan="1" colspan="1">N7—N6—H6</td><td rowspan="1" colspan="1">121.2 (12)</td></tr><tr><td rowspan="1" colspan="1">N2—N3—S2</td><td rowspan="1" colspan="1">115.55 (9)</td><td rowspan="1" colspan="1">N6—N7—S4</td><td rowspan="1" colspan="1">116.35 (9)</td></tr><tr><td rowspan="1" colspan="1">N2—N3—H3</td><td rowspan="1" colspan="1">113.4 (11)</td><td rowspan="1" colspan="1">N6—N7—H7</td><td rowspan="1" colspan="1">114.9 (11)</td></tr><tr><td rowspan="1" colspan="1">S2—N3—H3</td><td rowspan="1" colspan="1">112.1 (11)</td><td rowspan="1" colspan="1">S4—N7—H7</td><td rowspan="1" colspan="1">110.4 (11)</td></tr><tr><td rowspan="1" colspan="1">O4—N4—O3</td><td rowspan="1" colspan="1">123.45 (12)</td><td rowspan="1" colspan="1">O8—N8—O7</td><td rowspan="1" colspan="1">123.72 (12)</td></tr><tr><td rowspan="1" colspan="1">O4—N4—C10</td><td rowspan="1" colspan="1">118.93 (11)</td><td rowspan="1" colspan="1">O8—N8—C23</td><td rowspan="1" colspan="1">118.84 (12)</td></tr><tr><td rowspan="1" colspan="1">O3—N4—C10</td><td rowspan="1" colspan="1">117.61 (10)</td><td rowspan="1" colspan="1">O7—N8—C23</td><td rowspan="1" colspan="1">117.43 (11)</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">N1—C1—C2—C3</td><td rowspan="1" colspan="1">−179.34 (12)</td><td rowspan="1" colspan="1">N5—C14—C15—C16</td><td rowspan="1" colspan="1">−178.92 (12)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td><td rowspan="1" colspan="1">−1.78 (18)</td><td rowspan="1" colspan="1">C19—C14—C15—C16</td><td rowspan="1" colspan="1">0.54 (18)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">0.6 (2)</td><td rowspan="1" colspan="1">C14—C15—C16—C17</td><td rowspan="1" colspan="1">0.38 (19)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">0.7 (2)</td><td rowspan="1" colspan="1">C15—C16—C17—C18</td><td rowspan="1" colspan="1">−0.7 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">−0.9 (2)</td><td rowspan="1" colspan="1">C16—C17—C18—C19</td><td rowspan="1" colspan="1">0.1 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">−0.28 (19)</td><td rowspan="1" colspan="1">C17—C18—C19—C14</td><td rowspan="1" colspan="1">0.88 (19)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—S1</td><td rowspan="1" colspan="1">178.53 (10)</td><td rowspan="1" colspan="1">C17—C18—C19—S3</td><td rowspan="1" colspan="1">179.20 (10)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">1.64 (19)</td><td rowspan="1" colspan="1">N5—C14—C19—C18</td><td rowspan="1" colspan="1">178.32 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6—C5</td><td rowspan="1" colspan="1">179.45 (11)</td><td rowspan="1" colspan="1">C15—C14—C19—C18</td><td rowspan="1" colspan="1">−1.20 (19)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—S1</td><td rowspan="1" colspan="1">−177.37 (10)</td><td rowspan="1" colspan="1">N5—C14—C19—S3</td><td rowspan="1" colspan="1">−0.30 (14)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6—S1</td><td rowspan="1" colspan="1">0.44 (14)</td><td rowspan="1" colspan="1">C15—C14—C19—S3</td><td rowspan="1" colspan="1">−179.81 (9)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—C9—C10</td><td rowspan="1" colspan="1">−0.02 (18)</td><td rowspan="1" colspan="1">C26—C21—C22—C23</td><td rowspan="1" colspan="1">0.08 (19)</td></tr><tr><td rowspan="1" colspan="1">S2—C8—C9—C10</td><td rowspan="1" colspan="1">−178.02 (9)</td><td rowspan="1" colspan="1">S4—C21—C22—C23</td><td rowspan="1" colspan="1">−179.45 (9)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">0.36 (19)</td><td rowspan="1" colspan="1">C21—C22—C23—C24</td><td rowspan="1" colspan="1">−0.62 (19)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10—N4</td><td rowspan="1" colspan="1">−179.90 (11)</td><td rowspan="1" colspan="1">C21—C22—C23—N8</td><td rowspan="1" colspan="1">178.59 (11)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">−0.48 (19)</td><td rowspan="1" colspan="1">C22—C23—C24—C25</td><td rowspan="1" colspan="1">0.4 (2)</td></tr><tr><td rowspan="1" colspan="1">N4—C10—C11—C12</td><td rowspan="1" colspan="1">179.79 (11)</td><td rowspan="1" colspan="1">N8—C23—C24—C25</td><td rowspan="1" colspan="1">−178.77 (11)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">0.25 (19)</td><td rowspan="1" colspan="1">C23—C24—C25—C26</td><td rowspan="1" colspan="1">0.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C13—C12</td><td rowspan="1" colspan="1">−0.19 (19)</td><td rowspan="1" colspan="1">C24—C25—C26—C21</td><td rowspan="1" colspan="1">−0.8 (2)</td></tr><tr><td rowspan="1" colspan="1">S2—C8—C13—C12</td><td rowspan="1" colspan="1">177.77 (10)</td><td rowspan="1" colspan="1">C22—C21—C26—C25</td><td rowspan="1" colspan="1">0.63 (19)</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C13—C8</td><td rowspan="1" colspan="1">0.07 (19)</td><td rowspan="1" colspan="1">S4—C21—C26—C25</td><td rowspan="1" colspan="1">−179.85 (10)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—S1—C7</td><td rowspan="1" colspan="1">−179.42 (13)</td><td rowspan="1" colspan="1">C18—C19—S3—C20</td><td rowspan="1" colspan="1">−178.41 (13)</td></tr><tr><td rowspan="1" colspan="1">C1—C6—S1—C7</td><td rowspan="1" colspan="1">−0.50 (9)</td><td rowspan="1" colspan="1">C14—C19—S3—C20</td><td rowspan="1" colspan="1">0.08 (9)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—S1—C6</td><td rowspan="1" colspan="1">0.52 (10)</td><td rowspan="1" colspan="1">N5—C20—S3—C19</td><td rowspan="1" colspan="1">0.17 (10)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—S1—C6</td><td rowspan="1" colspan="1">−179.24 (11)</td><td rowspan="1" colspan="1">N6—C20—S3—C19</td><td rowspan="1" colspan="1">179.86 (11)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2—O2</td><td rowspan="1" colspan="1">165.20 (10)</td><td rowspan="1" colspan="1">C22—C21—S4—O5</td><td rowspan="1" colspan="1">19.55 (12)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2—O2</td><td rowspan="1" colspan="1">−12.82 (12)</td><td rowspan="1" colspan="1">C26—C21—S4—O5</td><td rowspan="1" colspan="1">−159.98 (11)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2—O1</td><td rowspan="1" colspan="1">31.90 (12)</td><td rowspan="1" colspan="1">C22—C21—S4—O6</td><td rowspan="1" colspan="1">153.05 (10)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2—O1</td><td rowspan="1" colspan="1">−146.12 (10)</td><td rowspan="1" colspan="1">C26—C21—S4—O6</td><td rowspan="1" colspan="1">−26.48 (12)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2—N3</td><td rowspan="1" colspan="1">−79.99 (11)</td><td rowspan="1" colspan="1">C22—C21—S4—N7</td><td rowspan="1" colspan="1">−92.13 (11)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2—N3</td><td rowspan="1" colspan="1">101.99 (11)</td><td rowspan="1" colspan="1">C26—C21—S4—N7</td><td rowspan="1" colspan="1">88.34 (11)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—N1—C1</td><td rowspan="1" colspan="1">179.39 (11)</td><td rowspan="1" colspan="1">N6—C20—N5—C14</td><td rowspan="1" colspan="1">179.96 (12)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—N1—C1</td><td rowspan="1" colspan="1">−0.35 (13)</td><td rowspan="1" colspan="1">S3—C20—N5—C14</td><td rowspan="1" colspan="1">−0.36 (14)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—N1—C7</td><td rowspan="1" colspan="1">177.58 (12)</td><td rowspan="1" colspan="1">C15—C14—N5—C20</td><td rowspan="1" colspan="1">179.91 (12)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—N1—C7</td><td rowspan="1" colspan="1">−0.07 (15)</td><td rowspan="1" colspan="1">C19—C14—N5—C20</td><td rowspan="1" colspan="1">0.42 (15)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—N2—N3</td><td rowspan="1" colspan="1">168.50 (11)</td><td rowspan="1" colspan="1">N5—C20—N6—N7</td><td rowspan="1" colspan="1">177.46 (11)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—N2—N3</td><td rowspan="1" colspan="1">−11.75 (16)</td><td rowspan="1" colspan="1">S3—C20—N6—N7</td><td rowspan="1" colspan="1">−2.20 (17)</td></tr><tr><td rowspan="1" colspan="1">C7—N2—N3—S2</td><td rowspan="1" colspan="1">−99.88 (12)</td><td rowspan="1" colspan="1">C20—N6—N7—S4</td><td rowspan="1" colspan="1">−103.52 (12)</td></tr><tr><td rowspan="1" colspan="1">O2—S2—N3—N2</td><td rowspan="1" colspan="1">52.10 (10)</td><td rowspan="1" colspan="1">O5—S4—N7—N6</td><td rowspan="1" colspan="1">−176.11 (9)</td></tr><tr><td rowspan="1" colspan="1">O1—S2—N3—N2</td><td rowspan="1" colspan="1">−178.24 (9)</td><td rowspan="1" colspan="1">O6—S4—N7—N6</td><td rowspan="1" colspan="1">53.82 (10)</td></tr><tr><td rowspan="1" colspan="1">C8—S2—N3—N2</td><td rowspan="1" colspan="1">−63.47 (10)</td><td rowspan="1" colspan="1">C21—S4—N7—N6</td><td rowspan="1" colspan="1">−61.41 (10)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—N4—O4</td><td rowspan="1" colspan="1">−179.83 (12)</td><td rowspan="1" colspan="1">C22—C23—N8—O8</td><td rowspan="1" colspan="1">178.31 (12)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—N4—O4</td><td rowspan="1" colspan="1">−0.08 (18)</td><td rowspan="1" colspan="1">C24—C23—N8—O8</td><td rowspan="1" colspan="1">−2.44 (18)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—N4—O3</td><td rowspan="1" colspan="1">0.70 (17)</td><td rowspan="1" colspan="1">C22—C23—N8—O7</td><td rowspan="1" colspan="1">−2.85 (17)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—N4—O3</td><td rowspan="1" colspan="1">−179.55 (12)</td><td rowspan="1" colspan="1">C24—C23—N8—O7</td><td rowspan="1" colspan="1">176.39 (12)</td></tr></table></table-wrap></sec><sec id="d1e6147" sec-type="tablewraphbondslong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazole (II) </label><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e6156"><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">N2—H2···N5</td><td rowspan="1" colspan="1">0.816 (18)</td><td rowspan="1" colspan="1">2.033 (18)</td><td rowspan="1" colspan="1">2.8447 (15)</td><td rowspan="1" colspan="1">172.7 (16)</td></tr><tr><td rowspan="1" colspan="1">N3—H3···O3<sup>i</sup></td><td rowspan="1" colspan="1">0.848 (17)</td><td rowspan="1" colspan="1">2.129 (18)</td><td rowspan="1" colspan="1">2.9427 (15)</td><td rowspan="1" colspan="1">160.8 (15)</td></tr><tr><td rowspan="1" colspan="1">N6—H6···N1</td><td rowspan="1" colspan="1">0.820 (18)</td><td rowspan="1" colspan="1">2.050 (18)</td><td rowspan="1" colspan="1">2.8601 (15)</td><td rowspan="1" colspan="1">169.2 (17)</td></tr><tr><td rowspan="1" colspan="1">N7—H7···O7<sup>ii</sup></td><td rowspan="1" colspan="1">0.871 (17)</td><td rowspan="1" colspan="1">2.123 (18)</td><td rowspan="1" colspan="1">2.9472 (15)</td><td rowspan="1" colspan="1">157.6 (15)</td></tr><tr><td rowspan="1" colspan="1">C15—H15···O3<sup>i</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.65</td><td rowspan="1" colspan="1">3.4888 (17)</td><td rowspan="1" colspan="1">147</td></tr><tr><td rowspan="1" colspan="1">C26—H26···O2</td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.44</td><td rowspan="1" colspan="1">3.1774 (16)</td><td rowspan="1" colspan="1">134</td></tr><tr><td rowspan="1" colspan="1">C5—H5···O1<sup>iii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.66</td><td rowspan="1" colspan="1">3.3218 (16)</td><td rowspan="1" colspan="1">127</td></tr><tr><td rowspan="1" colspan="1">C13—H13···O6</td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.56</td><td rowspan="1" colspan="1">3.2731 (16)</td><td rowspan="1" colspan="1">133</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>, −<italic>y</italic>+1, −<italic>z</italic>; (ii) −<italic>x</italic>+1, −<italic>y</italic>, −<italic>z</italic>+1; (iii) −<italic>x</italic>, −<italic>y</italic>+1, −<italic>z</italic>+1.</p></sec><sec id="d1e6351" sec-type="tablewrapcrystaldatalong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Crystal data</title><table-wrap position="anchor" id="d1e6360"><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>13</sub>H<sub>11</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub><sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup></td><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 553.54</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 568</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.625 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 10.0399 (5) Å</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>b</italic> = 10.7585 (4) Å</td><td rowspan="1" colspan="1">Cell parameters from 14254 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 11.3372 (6) Å</td><td rowspan="1" colspan="1">θ = 2.0–27.5°</td></tr><tr><td rowspan="1" colspan="1">α = 85.607 (4)°</td><td rowspan="1" colspan="1">µ = 0.39 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 71.369 (5)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 100 K</td></tr><tr><td rowspan="1" colspan="1">γ = 77.115 (4)°</td><td rowspan="1" colspan="1">Plate, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1131.16 (10) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.23 × 0.18 × 0.04 mm</td></tr></table></table-wrap></sec><sec id="d1e6501" sec-type="tablewrapdatacollectionlong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Data collection</title><table-wrap position="anchor" id="d1e6510"><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 Mercury CCD diffractometer</td><td rowspan="1" colspan="1">4880 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.017</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>FS_ABSCOR</italic>; Rigaku, 2013)</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 27.6°, θ<sub>min</sub> = 2.2°</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.879, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>h</italic> = −13→11</td></tr><tr><td rowspan="1" colspan="1">19781 measured reflections</td><td rowspan="1" colspan="1"><italic>k</italic> = −14→13</td></tr><tr><td rowspan="1" colspan="1">5159 independent reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −14→14</td></tr></table></table-wrap></sec><sec id="d1e6610" sec-type="tablewraprefinementdatalong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Refinement</title><table-wrap position="anchor" id="d1e6619"><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>)] = 0.029</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>) = 0.076</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0353<italic>P</italic>)<sup>2</sup> + 0.8265<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> = 1.02</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.002</td></tr><tr><td rowspan="1" colspan="1">5159 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.39 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">334 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.42 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="d1e6765" sec-type="specialdetails"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Special details</title><table-wrap position="anchor" id="d1e6775"><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="d1e6784" sec-type="tablewrapcoords"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e6796"><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">1.07390 (14)</td><td rowspan="1" colspan="1">0.16015 (12)</td><td rowspan="1" colspan="1">−0.12063 (12)</td><td rowspan="1" colspan="1">0.0159 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">1.21341 (15)</td><td rowspan="1" colspan="1">0.10073 (13)</td><td rowspan="1" colspan="1">−0.18674 (14)</td><td rowspan="1" colspan="1">0.0198 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2A</td><td rowspan="1" colspan="1">1.2930</td><td rowspan="1" colspan="1">0.1380</td><td rowspan="1" colspan="1">−0.1940</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">1.23134 (15)</td><td rowspan="1" colspan="1">−0.01528 (13)</td><td rowspan="1" colspan="1">−0.24169 (14)</td><td rowspan="1" colspan="1">0.0211 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3A</td><td rowspan="1" colspan="1">1.3252</td><td rowspan="1" colspan="1">−0.0581</td><td rowspan="1" colspan="1">−0.2878</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">1.11437 (15)</td><td rowspan="1" colspan="1">−0.07065 (13)</td><td rowspan="1" colspan="1">−0.23068 (13)</td><td rowspan="1" colspan="1">0.0197 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">1.1304</td><td rowspan="1" colspan="1">−0.1505</td><td rowspan="1" colspan="1">−0.2689</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.97546 (15)</td><td rowspan="1" colspan="1">−0.01107 (13)</td><td rowspan="1" colspan="1">−0.16489 (13)</td><td rowspan="1" colspan="1">0.0177 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.8958</td><td rowspan="1" colspan="1">−0.0484</td><td rowspan="1" colspan="1">−0.1574</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.95732 (14)</td><td rowspan="1" colspan="1">0.10512 (12)</td><td rowspan="1" colspan="1">−0.11042 (12)</td><td rowspan="1" colspan="1">0.0151 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.84167 (14)</td><td rowspan="1" colspan="1">0.28675 (12)</td><td rowspan="1" colspan="1">−0.00034 (12)</td><td rowspan="1" colspan="1">0.0151 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.55707 (14)</td><td rowspan="1" colspan="1">0.47110 (13)</td><td rowspan="1" colspan="1">0.32289 (12)</td><td rowspan="1" colspan="1">0.0167 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.53199 (16)</td><td rowspan="1" colspan="1">0.36315 (14)</td><td rowspan="1" colspan="1">0.39425 (13)</td><td rowspan="1" colspan="1">0.0211 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">0.6099</td><td rowspan="1" colspan="1">0.3004</td><td rowspan="1" colspan="1">0.4059</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.39098 (18)</td><td rowspan="1" colspan="1">0.34797 (15)</td><td rowspan="1" colspan="1">0.44861 (14)</td><td rowspan="1" colspan="1">0.0269 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">0.3725</td><td rowspan="1" colspan="1">0.2748</td><td rowspan="1" colspan="1">0.4983</td><td rowspan="1" colspan="1">0.032*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.27802 (17)</td><td rowspan="1" colspan="1">0.43861 (17)</td><td rowspan="1" colspan="1">0.43063 (14)</td><td rowspan="1" colspan="1">0.0285 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">0.1816</td><td rowspan="1" colspan="1">0.4289</td><td rowspan="1" colspan="1">0.4679</td><td rowspan="1" colspan="1">0.034*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.30799 (16)</td><td rowspan="1" colspan="1">0.54390 (16)</td><td rowspan="1" colspan="1">0.35725 (13)</td><td rowspan="1" colspan="1">0.0255 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.44587 (15)</td><td rowspan="1" colspan="1">0.56403 (14)</td><td rowspan="1" colspan="1">0.30272 (13)</td><td rowspan="1" colspan="1">0.0209 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.4637</td><td rowspan="1" colspan="1">0.6378</td><td rowspan="1" colspan="1">0.2538</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">1.01665 (3)</td><td rowspan="1" colspan="1">0.30546 (3)</td><td rowspan="1" colspan="1">−0.04133 (3)</td><td rowspan="1" colspan="1">0.01753 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">0.73513 (3)</td><td rowspan="1" colspan="1">0.49153 (3)</td><td rowspan="1" colspan="1">0.25131 (3)</td><td rowspan="1" colspan="1">0.01507 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.82742 (12)</td><td rowspan="1" colspan="1">0.17982 (11)</td><td rowspan="1" colspan="1">−0.04048 (10)</td><td rowspan="1" colspan="1">0.0154 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.746 (2)</td><td rowspan="1" colspan="1">0.1638 (16)</td><td rowspan="1" colspan="1">−0.0270 (16)</td><td rowspan="1" colspan="1">0.018*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.73035 (13)</td><td rowspan="1" colspan="1">0.37297 (11)</td><td rowspan="1" colspan="1">0.06510 (11)</td><td rowspan="1" colspan="1">0.0176 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.646 (2)</td><td rowspan="1" colspan="1">0.3709 (17)</td><td rowspan="1" colspan="1">0.0737 (16)</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.76169 (12)</td><td rowspan="1" colspan="1">0.48236 (11)</td><td rowspan="1" colspan="1">0.09996 (11)</td><td rowspan="1" colspan="1">0.0166 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.7208 (19)</td><td rowspan="1" colspan="1">0.5525 (17)</td><td rowspan="1" colspan="1">0.0710 (16)</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.18823 (15)</td><td rowspan="1" colspan="1">0.63839 (18)</td><td rowspan="1" colspan="1">0.33454 (13)</td><td rowspan="1" colspan="1">0.0396 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.82921 (11)</td><td rowspan="1" colspan="1">0.38488 (9)</td><td rowspan="1" colspan="1">0.28530 (10)</td><td rowspan="1" colspan="1">0.0220 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.74518 (11)</td><td rowspan="1" colspan="1">0.61876 (9)</td><td rowspan="1" colspan="1">0.26804 (9)</td><td rowspan="1" colspan="1">0.0195 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.21622 (15)</td><td rowspan="1" colspan="1">0.73477 (17)</td><td rowspan="1" colspan="1">0.27552 (14)</td><td rowspan="1" colspan="1">0.0584 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.06728 (14)</td><td rowspan="1" colspan="1">0.61654 (19)</td><td rowspan="1" colspan="1">0.37558 (15)</td><td rowspan="1" colspan="1">0.0589 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.31611 (14)</td><td rowspan="1" colspan="1">0.18627 (13)</td><td rowspan="1" colspan="1">0.18875 (13)</td><td rowspan="1" colspan="1">0.0164 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.36568 (15)</td><td rowspan="1" colspan="1">0.07109 (13)</td><td rowspan="1" colspan="1">0.23976 (13)</td><td rowspan="1" colspan="1">0.0197 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.4570</td><td rowspan="1" colspan="1">0.0192</td><td rowspan="1" colspan="1">0.1998</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.27603 (16)</td><td rowspan="1" colspan="1">0.03482 (14)</td><td rowspan="1" colspan="1">0.35187 (14)</td><td rowspan="1" colspan="1">0.0218 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.14253 (15)</td><td rowspan="1" colspan="1">0.10749 (14)</td><td rowspan="1" colspan="1">0.41347 (13)</td><td rowspan="1" colspan="1">0.0219 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17</td><td rowspan="1" colspan="1">0.0849</td><td rowspan="1" colspan="1">0.0799</td><td rowspan="1" colspan="1">0.4907</td><td rowspan="1" colspan="1">0.026*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.09530 (15)</td><td rowspan="1" colspan="1">0.22141 (14)</td><td rowspan="1" colspan="1">0.35952 (14)</td><td rowspan="1" colspan="1">0.0212 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">0.0036</td><td rowspan="1" colspan="1">0.2727</td><td rowspan="1" colspan="1">0.3995</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.18114 (15)</td><td rowspan="1" colspan="1">0.26111 (13)</td><td rowspan="1" colspan="1">0.24729 (13)</td><td rowspan="1" colspan="1">0.0194 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">0.1480</td><td rowspan="1" colspan="1">0.3392</td><td rowspan="1" colspan="1">0.2103</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S3</td><td rowspan="1" colspan="1">0.42650 (3)</td><td rowspan="1" colspan="1">0.24195 (3)</td><td rowspan="1" colspan="1">0.04827 (3)</td><td rowspan="1" colspan="1">0.01634 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.32639 (15)</td><td rowspan="1" colspan="1">−0.08700 (13)</td><td rowspan="1" colspan="1">0.40760 (13)</td><td rowspan="1" colspan="1">0.0315 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.45472 (11)</td><td rowspan="1" colspan="1">0.36044 (9)</td><td rowspan="1" colspan="1">0.08076 (10)</td><td rowspan="1" colspan="1">0.0225 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O6</td><td rowspan="1" colspan="1">0.55538 (10)</td><td rowspan="1" colspan="1">0.14188 (9)</td><td rowspan="1" colspan="1">0.00769 (9)</td><td rowspan="1" colspan="1">0.0200 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O7</td><td rowspan="1" colspan="1">0.34166 (11)</td><td rowspan="1" colspan="1">0.26546 (10)</td><td rowspan="1" colspan="1">−0.03675 (10)</td><td rowspan="1" colspan="1">0.0224 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O8</td><td rowspan="1" colspan="1">0.23692 (14)</td><td rowspan="1" colspan="1">−0.13450 (12)</td><td rowspan="1" colspan="1">0.48774 (11)</td><td rowspan="1" colspan="1">0.0393 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O9</td><td rowspan="1" colspan="1">0.45499 (14)</td><td rowspan="1" colspan="1">−0.13511 (13)</td><td rowspan="1" colspan="1">0.37160 (14)</td><td rowspan="1" colspan="1">0.0493 (4)</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e7484" sec-type="tablewrapadps"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e7496"><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">0.0170 (6)</td><td rowspan="1" colspan="1">0.0135 (6)</td><td rowspan="1" colspan="1">0.0176 (6)</td><td rowspan="1" colspan="1">−0.0045 (5)</td><td rowspan="1" colspan="1">−0.0045 (5)</td><td rowspan="1" colspan="1">−0.0013 (5)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0157 (6)</td><td rowspan="1" colspan="1">0.0183 (6)</td><td rowspan="1" colspan="1">0.0247 (7)</td><td rowspan="1" colspan="1">−0.0044 (5)</td><td rowspan="1" colspan="1">−0.0044 (5)</td><td rowspan="1" colspan="1">−0.0016 (5)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0179 (7)</td><td rowspan="1" colspan="1">0.0176 (6)</td><td rowspan="1" colspan="1">0.0247 (7)</td><td rowspan="1" colspan="1">−0.0003 (5)</td><td rowspan="1" colspan="1">−0.0041 (5)</td><td rowspan="1" colspan="1">−0.0034 (5)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0241 (7)</td><td rowspan="1" colspan="1">0.0141 (6)</td><td rowspan="1" colspan="1">0.0214 (7)</td><td rowspan="1" colspan="1">−0.0027 (5)</td><td rowspan="1" colspan="1">−0.0081 (5)</td><td rowspan="1" colspan="1">−0.0031 (5)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0202 (6)</td><td rowspan="1" colspan="1">0.0163 (6)</td><td rowspan="1" colspan="1">0.0195 (6)</td><td rowspan="1" colspan="1">−0.0065 (5)</td><td rowspan="1" colspan="1">−0.0082 (5)</td><td rowspan="1" colspan="1">−0.0002 (5)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0149 (6)</td><td rowspan="1" colspan="1">0.0156 (6)</td><td rowspan="1" colspan="1">0.0149 (6)</td><td rowspan="1" colspan="1">−0.0037 (5)</td><td rowspan="1" colspan="1">−0.0048 (5)</td><td rowspan="1" colspan="1">0.0008 (5)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0146 (6)</td><td rowspan="1" colspan="1">0.0172 (6)</td><td rowspan="1" colspan="1">0.0142 (6)</td><td rowspan="1" colspan="1">−0.0054 (5)</td><td rowspan="1" colspan="1">−0.0040 (5)</td><td rowspan="1" colspan="1">0.0006 (5)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0162 (6)</td><td rowspan="1" colspan="1">0.0195 (6)</td><td rowspan="1" colspan="1">0.0141 (6)</td><td rowspan="1" colspan="1">−0.0047 (5)</td><td rowspan="1" colspan="1">−0.0032 (5)</td><td rowspan="1" colspan="1">−0.0019 (5)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0269 (7)</td><td rowspan="1" colspan="1">0.0191 (7)</td><td rowspan="1" colspan="1">0.0171 (6)</td><td rowspan="1" colspan="1">−0.0079 (5)</td><td rowspan="1" colspan="1">−0.0041 (5)</td><td rowspan="1" colspan="1">−0.0012 (5)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0321 (8)</td><td rowspan="1" colspan="1">0.0294 (8)</td><td rowspan="1" colspan="1">0.0193 (7)</td><td rowspan="1" colspan="1">−0.0163 (6)</td><td rowspan="1" colspan="1">−0.0011 (6)</td><td rowspan="1" colspan="1">−0.0025 (6)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0225 (7)</td><td rowspan="1" colspan="1">0.0459 (9)</td><td rowspan="1" colspan="1">0.0186 (7)</td><td rowspan="1" colspan="1">−0.0158 (7)</td><td rowspan="1" colspan="1">−0.0005 (6)</td><td rowspan="1" colspan="1">−0.0091 (6)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0178 (7)</td><td rowspan="1" colspan="1">0.0423 (9)</td><td rowspan="1" colspan="1">0.0155 (6)</td><td rowspan="1" colspan="1">−0.0017 (6)</td><td rowspan="1" colspan="1">−0.0056 (5)</td><td rowspan="1" colspan="1">−0.0059 (6)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0193 (7)</td><td rowspan="1" colspan="1">0.0270 (7)</td><td rowspan="1" colspan="1">0.0143 (6)</td><td rowspan="1" colspan="1">−0.0020 (5)</td><td rowspan="1" colspan="1">−0.0042 (5)</td><td rowspan="1" colspan="1">−0.0004 (5)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.01279 (15)</td><td rowspan="1" colspan="1">0.01565 (15)</td><td rowspan="1" colspan="1">0.02306 (17)</td><td rowspan="1" colspan="1">−0.00532 (12)</td><td rowspan="1" colspan="1">−0.00137 (12)</td><td rowspan="1" colspan="1">−0.00507 (12)</td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">0.01461 (15)</td><td rowspan="1" colspan="1">0.01342 (15)</td><td rowspan="1" colspan="1">0.01680 (16)</td><td rowspan="1" colspan="1">−0.00269 (11)</td><td rowspan="1" colspan="1">−0.00443 (12)</td><td rowspan="1" colspan="1">−0.00064 (11)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0128 (5)</td><td rowspan="1" colspan="1">0.0175 (5)</td><td rowspan="1" colspan="1">0.0167 (5)</td><td rowspan="1" colspan="1">−0.0055 (4)</td><td rowspan="1" colspan="1">−0.0039 (4)</td><td rowspan="1" colspan="1">−0.0018 (4)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0124 (5)</td><td rowspan="1" colspan="1">0.0190 (6)</td><td rowspan="1" colspan="1">0.0214 (6)</td><td rowspan="1" colspan="1">−0.0053 (4)</td><td rowspan="1" colspan="1">−0.0025 (4)</td><td rowspan="1" colspan="1">−0.0063 (4)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0174 (5)</td><td rowspan="1" colspan="1">0.0146 (5)</td><td rowspan="1" colspan="1">0.0174 (5)</td><td rowspan="1" colspan="1">−0.0046 (4)</td><td rowspan="1" colspan="1">−0.0036 (4)</td><td rowspan="1" colspan="1">−0.0021 (4)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0208 (7)</td><td rowspan="1" colspan="1">0.0723 (12)</td><td rowspan="1" colspan="1">0.0192 (7)</td><td rowspan="1" colspan="1">0.0057 (7)</td><td rowspan="1" colspan="1">−0.0070 (5)</td><td rowspan="1" colspan="1">−0.0037 (7)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0195 (5)</td><td rowspan="1" colspan="1">0.0190 (5)</td><td rowspan="1" colspan="1">0.0278 (5)</td><td rowspan="1" colspan="1">−0.0004 (4)</td><td rowspan="1" colspan="1">−0.0105 (4)</td><td rowspan="1" colspan="1">0.0006 (4)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0224 (5)</td><td rowspan="1" colspan="1">0.0160 (5)</td><td rowspan="1" colspan="1">0.0196 (5)</td><td rowspan="1" colspan="1">−0.0059 (4)</td><td rowspan="1" colspan="1">−0.0044 (4)</td><td rowspan="1" colspan="1">−0.0021 (4)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0337 (7)</td><td rowspan="1" colspan="1">0.0828 (12)</td><td rowspan="1" colspan="1">0.0411 (8)</td><td rowspan="1" colspan="1">0.0156 (7)</td><td rowspan="1" colspan="1">−0.0114 (6)</td><td rowspan="1" colspan="1">0.0212 (8)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0166 (6)</td><td rowspan="1" colspan="1">0.1043 (14)</td><td rowspan="1" colspan="1">0.0500 (9)</td><td rowspan="1" colspan="1">−0.0015 (7)</td><td rowspan="1" colspan="1">−0.0084 (6)</td><td rowspan="1" colspan="1">−0.0081 (9)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0150 (6)</td><td rowspan="1" colspan="1">0.0186 (6)</td><td rowspan="1" colspan="1">0.0185 (6)</td><td rowspan="1" colspan="1">−0.0065 (5)</td><td rowspan="1" colspan="1">−0.0071 (5)</td><td rowspan="1" colspan="1">0.0009 (5)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0154 (6)</td><td rowspan="1" colspan="1">0.0201 (7)</td><td rowspan="1" colspan="1">0.0225 (7)</td><td rowspan="1" colspan="1">−0.0030 (5)</td><td rowspan="1" colspan="1">−0.0053 (5)</td><td rowspan="1" colspan="1">0.0020 (5)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0209 (7)</td><td rowspan="1" colspan="1">0.0207 (7)</td><td rowspan="1" colspan="1">0.0222 (7)</td><td rowspan="1" colspan="1">−0.0030 (5)</td><td rowspan="1" colspan="1">−0.0066 (5)</td><td rowspan="1" colspan="1">0.0050 (5)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0199 (7)</td><td rowspan="1" colspan="1">0.0261 (7)</td><td rowspan="1" colspan="1">0.0187 (7)</td><td rowspan="1" colspan="1">−0.0061 (6)</td><td rowspan="1" colspan="1">−0.0037 (5)</td><td rowspan="1" colspan="1">−0.0005 (5)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0161 (6)</td><td rowspan="1" colspan="1">0.0239 (7)</td><td rowspan="1" colspan="1">0.0228 (7)</td><td rowspan="1" colspan="1">−0.0015 (5)</td><td rowspan="1" colspan="1">−0.0056 (5)</td><td rowspan="1" colspan="1">−0.0054 (5)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.0197 (7)</td><td rowspan="1" colspan="1">0.0174 (6)</td><td rowspan="1" colspan="1">0.0233 (7)</td><td rowspan="1" colspan="1">−0.0034 (5)</td><td rowspan="1" colspan="1">−0.0099 (5)</td><td rowspan="1" colspan="1">−0.0010 (5)</td></tr><tr><td rowspan="1" colspan="1">S3</td><td rowspan="1" colspan="1">0.01426 (15)</td><td rowspan="1" colspan="1">0.01613 (16)</td><td rowspan="1" colspan="1">0.02054 (17)</td><td rowspan="1" colspan="1">−0.00592 (12)</td><td rowspan="1" colspan="1">−0.00693 (12)</td><td rowspan="1" colspan="1">0.00324 (12)</td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.0284 (7)</td><td rowspan="1" colspan="1">0.0281 (7)</td><td rowspan="1" colspan="1">0.0269 (7)</td><td rowspan="1" colspan="1">0.0010 (5)</td><td rowspan="1" colspan="1">−0.0006 (5)</td><td rowspan="1" colspan="1">0.0102 (5)</td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.0195 (5)</td><td rowspan="1" colspan="1">0.0176 (5)</td><td rowspan="1" colspan="1">0.0322 (6)</td><td rowspan="1" colspan="1">−0.0076 (4)</td><td rowspan="1" colspan="1">−0.0083 (4)</td><td rowspan="1" colspan="1">0.0000 (4)</td></tr><tr><td rowspan="1" colspan="1">O6</td><td rowspan="1" colspan="1">0.0152 (5)</td><td rowspan="1" colspan="1">0.0189 (5)</td><td rowspan="1" colspan="1">0.0253 (5)</td><td rowspan="1" colspan="1">−0.0058 (4)</td><td rowspan="1" colspan="1">−0.0043 (4)</td><td rowspan="1" colspan="1">0.0014 (4)</td></tr><tr><td rowspan="1" colspan="1">O7</td><td rowspan="1" colspan="1">0.0230 (5)</td><td rowspan="1" colspan="1">0.0253 (5)</td><td rowspan="1" colspan="1">0.0236 (5)</td><td rowspan="1" colspan="1">−0.0090 (4)</td><td rowspan="1" colspan="1">−0.0126 (4)</td><td rowspan="1" colspan="1">0.0066 (4)</td></tr><tr><td rowspan="1" colspan="1">O8</td><td rowspan="1" colspan="1">0.0388 (7)</td><td rowspan="1" colspan="1">0.0325 (6)</td><td rowspan="1" colspan="1">0.0298 (6)</td><td rowspan="1" colspan="1">−0.0029 (5)</td><td rowspan="1" colspan="1">0.0058 (5)</td><td rowspan="1" colspan="1">0.0143 (5)</td></tr><tr><td rowspan="1" colspan="1">O9</td><td rowspan="1" colspan="1">0.0287 (7)</td><td rowspan="1" colspan="1">0.0444 (8)</td><td rowspan="1" colspan="1">0.0511 (8)</td><td rowspan="1" colspan="1">0.0100 (6)</td><td rowspan="1" colspan="1">0.0022 (6)</td><td rowspan="1" colspan="1">0.0252 (6)</td></tr></table></table-wrap></sec><sec id="d1e8249" sec-type="tablewrapgeomlong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e8259"><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—C2</td><td rowspan="1" colspan="1">1.3913 (19)</td><td rowspan="1" colspan="1">S2—O2</td><td rowspan="1" colspan="1">1.4260 (10)</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.3950 (18)</td><td rowspan="1" colspan="1">S2—O1</td><td rowspan="1" colspan="1">1.4279 (10)</td></tr><tr><td rowspan="1" colspan="1">C1—S1</td><td rowspan="1" colspan="1">1.7513 (13)</td><td rowspan="1" colspan="1">S2—N3</td><td rowspan="1" colspan="1">1.6574 (12)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.3876 (19)</td><td rowspan="1" colspan="1">N1—H1</td><td rowspan="1" colspan="1">0.841 (19)</td></tr><tr><td rowspan="1" colspan="1">C2—H2A</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N2—N3</td><td rowspan="1" colspan="1">1.3985 (16)</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.399 (2)</td><td rowspan="1" colspan="1">N2—H2</td><td rowspan="1" colspan="1">0.826 (19)</td></tr><tr><td rowspan="1" colspan="1">C3—H3A</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N3—H3</td><td rowspan="1" colspan="1">0.869 (18)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.386 (2)</td><td rowspan="1" colspan="1">N4—O4</td><td rowspan="1" colspan="1">1.223 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N4—O3</td><td rowspan="1" colspan="1">1.227 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.3863 (18)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.3844 (19)</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C14—C19</td><td rowspan="1" colspan="1">1.3949 (19)</td></tr><tr><td rowspan="1" colspan="1">C6—N1</td><td rowspan="1" colspan="1">1.3946 (17)</td><td rowspan="1" colspan="1">C14—S3</td><td rowspan="1" colspan="1">1.7736 (14)</td></tr><tr><td rowspan="1" colspan="1">C7—N1</td><td rowspan="1" colspan="1">1.3215 (17)</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.3884 (19)</td></tr><tr><td rowspan="1" colspan="1">C7—N2</td><td rowspan="1" colspan="1">1.3317 (17)</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—S1</td><td rowspan="1" colspan="1">1.7218 (13)</td><td rowspan="1" colspan="1">C16—C17</td><td rowspan="1" colspan="1">1.383 (2)</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.3867 (19)</td><td rowspan="1" colspan="1">C16—N5</td><td rowspan="1" colspan="1">1.4677 (18)</td></tr><tr><td rowspan="1" colspan="1">C8—C13</td><td rowspan="1" colspan="1">1.3887 (19)</td><td rowspan="1" colspan="1">C17—C18</td><td rowspan="1" colspan="1">1.383 (2)</td></tr><tr><td rowspan="1" colspan="1">C8—S2</td><td rowspan="1" colspan="1">1.7674 (14)</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—C10</td><td rowspan="1" colspan="1">1.393 (2)</td><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.387 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.379 (2)</td><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">S3—O7</td><td rowspan="1" colspan="1">1.4526 (10)</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.383 (2)</td><td rowspan="1" colspan="1">S3—O6</td><td rowspan="1" colspan="1">1.4558 (10)</td></tr><tr><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">S3—O5</td><td rowspan="1" colspan="1">1.4630 (10)</td></tr><tr><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.383 (2)</td><td rowspan="1" colspan="1">N5—O9</td><td rowspan="1" colspan="1">1.2244 (18)</td></tr><tr><td rowspan="1" colspan="1">C12—N4</td><td rowspan="1" colspan="1">1.469 (2)</td><td rowspan="1" colspan="1">N5—O8</td><td rowspan="1" colspan="1">1.2270 (17)</td></tr><tr><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9500</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">C2—C1—C6</td><td rowspan="1" colspan="1">121.20 (12)</td><td rowspan="1" colspan="1">O2—S2—C8</td><td rowspan="1" colspan="1">110.40 (6)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—S1</td><td rowspan="1" colspan="1">128.05 (10)</td><td rowspan="1" colspan="1">O1—S2—C8</td><td rowspan="1" colspan="1">107.66 (6)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—S1</td><td rowspan="1" colspan="1">110.75 (10)</td><td rowspan="1" colspan="1">N3—S2—C8</td><td rowspan="1" colspan="1">104.82 (6)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">117.18 (13)</td><td rowspan="1" colspan="1">C7—N1—C6</td><td rowspan="1" colspan="1">113.48 (11)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2A</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C7—N1—H1</td><td rowspan="1" colspan="1">120.7 (12)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2A</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C6—N1—H1</td><td rowspan="1" colspan="1">125.7 (12)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">121.52 (13)</td><td rowspan="1" colspan="1">C7—N2—N3</td><td rowspan="1" colspan="1">116.58 (11)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3A</td><td rowspan="1" colspan="1">119.2</td><td rowspan="1" colspan="1">C7—N2—H2</td><td rowspan="1" colspan="1">123.0 (12)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3A</td><td rowspan="1" colspan="1">119.2</td><td rowspan="1" colspan="1">N3—N2—H2</td><td rowspan="1" colspan="1">119.4 (12)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">121.15 (13)</td><td rowspan="1" colspan="1">N2—N3—S2</td><td rowspan="1" colspan="1">114.02 (9)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">119.4</td><td rowspan="1" colspan="1">N2—N3—H3</td><td rowspan="1" colspan="1">113.4 (12)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">119.4</td><td rowspan="1" colspan="1">S2—N3—H3</td><td rowspan="1" colspan="1">111.7 (12)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">117.39 (12)</td><td rowspan="1" colspan="1">O4—N4—O3</td><td rowspan="1" colspan="1">124.11 (16)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">121.3</td><td rowspan="1" colspan="1">O4—N4—C12</td><td rowspan="1" colspan="1">118.27 (17)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">121.3</td><td rowspan="1" colspan="1">O3—N4—C12</td><td rowspan="1" colspan="1">117.62 (15)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—N1</td><td rowspan="1" colspan="1">126.36 (12)</td><td rowspan="1" colspan="1">C15—C14—C19</td><td rowspan="1" colspan="1">121.07 (13)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C1</td><td rowspan="1" colspan="1">121.56 (12)</td><td rowspan="1" colspan="1">C15—C14—S3</td><td rowspan="1" colspan="1">119.86 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C1</td><td rowspan="1" colspan="1">112.08 (12)</td><td rowspan="1" colspan="1">C19—C14—S3</td><td rowspan="1" colspan="1">119.06 (10)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—N2</td><td rowspan="1" colspan="1">122.94 (12)</td><td rowspan="1" colspan="1">C14—C15—C16</td><td rowspan="1" colspan="1">117.05 (13)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—S1</td><td rowspan="1" colspan="1">114.10 (10)</td><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">121.5</td></tr><tr><td rowspan="1" colspan="1">N2—C7—S1</td><td rowspan="1" colspan="1">122.96 (10)</td><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">121.5</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C13</td><td rowspan="1" colspan="1">121.98 (13)</td><td rowspan="1" colspan="1">C17—C16—C15</td><td rowspan="1" colspan="1">123.45 (13)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2</td><td rowspan="1" colspan="1">119.96 (11)</td><td rowspan="1" colspan="1">C17—C16—N5</td><td rowspan="1" colspan="1">118.58 (13)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2</td><td rowspan="1" colspan="1">118.04 (11)</td><td rowspan="1" colspan="1">C15—C16—N5</td><td rowspan="1" colspan="1">117.97 (13)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10</td><td rowspan="1" colspan="1">119.11 (14)</td><td rowspan="1" colspan="1">C18—C17—C16</td><td rowspan="1" colspan="1">118.15 (13)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C18—C17—H17</td><td rowspan="1" colspan="1">120.9</td></tr><tr><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C16—C17—H17</td><td rowspan="1" colspan="1">120.9</td></tr><tr><td rowspan="1" colspan="1">C11—C10—C9</td><td rowspan="1" colspan="1">120.37 (14)</td><td rowspan="1" colspan="1">C17—C18—C19</td><td rowspan="1" colspan="1">120.32 (13)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">C17—C18—H18</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">C19—C18—H18</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">118.62 (14)</td><td rowspan="1" colspan="1">C18—C19—C14</td><td rowspan="1" colspan="1">119.95 (13)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.7</td><td rowspan="1" colspan="1">C18—C19—H19</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.7</td><td rowspan="1" colspan="1">C14—C19—H19</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">123.14 (15)</td><td rowspan="1" colspan="1">O7—S3—O6</td><td rowspan="1" colspan="1">113.88 (6)</td></tr><tr><td rowspan="1" colspan="1">C13—C12—N4</td><td rowspan="1" colspan="1">118.14 (15)</td><td rowspan="1" colspan="1">O7—S3—O5</td><td rowspan="1" colspan="1">111.37 (6)</td></tr><tr><td rowspan="1" colspan="1">C11—C12—N4</td><td rowspan="1" colspan="1">118.71 (14)</td><td rowspan="1" colspan="1">O6—S3—O5</td><td rowspan="1" colspan="1">113.23 (6)</td></tr><tr><td rowspan="1" colspan="1">C12—C13—C8</td><td rowspan="1" colspan="1">116.76 (14)</td><td rowspan="1" colspan="1">O7—S3—C14</td><td rowspan="1" colspan="1">105.96 (6)</td></tr><tr><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">121.6</td><td rowspan="1" colspan="1">O6—S3—C14</td><td rowspan="1" colspan="1">106.14 (6)</td></tr><tr><td rowspan="1" colspan="1">C8—C13—H13</td><td rowspan="1" colspan="1">121.6</td><td rowspan="1" colspan="1">O5—S3—C14</td><td rowspan="1" colspan="1">105.46 (6)</td></tr><tr><td rowspan="1" colspan="1">C7—S1—C1</td><td rowspan="1" colspan="1">89.58 (6)</td><td rowspan="1" colspan="1">O9—N5—O8</td><td rowspan="1" colspan="1">123.89 (14)</td></tr><tr><td rowspan="1" colspan="1">O2—S2—O1</td><td rowspan="1" colspan="1">120.92 (6)</td><td rowspan="1" colspan="1">O9—N5—C16</td><td rowspan="1" colspan="1">118.16 (13)</td></tr><tr><td rowspan="1" colspan="1">O2—S2—N3</td><td rowspan="1" colspan="1">104.08 (6)</td><td rowspan="1" colspan="1">O8—N5—C16</td><td rowspan="1" colspan="1">117.95 (13)</td></tr><tr><td rowspan="1" colspan="1">O1—S2—N3</td><td rowspan="1" colspan="1">107.77 (6)</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—C3</td><td rowspan="1" colspan="1">−0.1 (2)</td><td rowspan="1" colspan="1">C5—C6—N1—C7</td><td rowspan="1" colspan="1">−179.60 (13)</td></tr><tr><td rowspan="1" colspan="1">S1—C1—C2—C3</td><td rowspan="1" colspan="1">179.86 (11)</td><td rowspan="1" colspan="1">C1—C6—N1—C7</td><td rowspan="1" colspan="1">0.83 (16)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.3 (2)</td><td rowspan="1" colspan="1">N1—C7—N2—N3</td><td rowspan="1" colspan="1">−179.22 (12)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">0.4 (2)</td><td rowspan="1" colspan="1">S1—C7—N2—N3</td><td rowspan="1" colspan="1">0.16 (17)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">−0.1 (2)</td><td rowspan="1" colspan="1">C7—N2—N3—S2</td><td rowspan="1" colspan="1">−110.54 (12)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—N1</td><td rowspan="1" colspan="1">−179.80 (13)</td><td rowspan="1" colspan="1">O2—S2—N3—N2</td><td rowspan="1" colspan="1">−168.76 (9)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">−0.3 (2)</td><td rowspan="1" colspan="1">O1—S2—N3—N2</td><td rowspan="1" colspan="1">61.70 (11)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">0.4 (2)</td><td rowspan="1" colspan="1">C8—S2—N3—N2</td><td rowspan="1" colspan="1">−52.78 (11)</td></tr><tr><td rowspan="1" colspan="1">S1—C1—C6—C5</td><td rowspan="1" colspan="1">−179.57 (10)</td><td rowspan="1" colspan="1">C13—C12—N4—O4</td><td rowspan="1" colspan="1">175.11 (15)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—N1</td><td rowspan="1" colspan="1">179.98 (12)</td><td rowspan="1" colspan="1">C11—C12—N4—O4</td><td rowspan="1" colspan="1">−4.1 (2)</td></tr><tr><td rowspan="1" colspan="1">S1—C1—C6—N1</td><td rowspan="1" colspan="1">0.03 (14)</td><td rowspan="1" colspan="1">C13—C12—N4—O3</td><td rowspan="1" colspan="1">−5.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—C9—C10</td><td rowspan="1" colspan="1">−0.8 (2)</td><td rowspan="1" colspan="1">C11—C12—N4—O3</td><td rowspan="1" colspan="1">175.70 (16)</td></tr><tr><td rowspan="1" colspan="1">S2—C8—C9—C10</td><td rowspan="1" colspan="1">−179.19 (11)</td><td rowspan="1" colspan="1">C19—C14—C15—C16</td><td rowspan="1" colspan="1">−0.8 (2)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">0.6 (2)</td><td rowspan="1" colspan="1">S3—C14—C15—C16</td><td rowspan="1" colspan="1">177.97 (11)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">0.3 (2)</td><td rowspan="1" colspan="1">C14—C15—C16—C17</td><td rowspan="1" colspan="1">−0.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">−1.2 (2)</td><td rowspan="1" colspan="1">C14—C15—C16—N5</td><td rowspan="1" colspan="1">179.96 (13)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12—N4</td><td rowspan="1" colspan="1">177.97 (14)</td><td rowspan="1" colspan="1">C15—C16—C17—C18</td><td rowspan="1" colspan="1">0.9 (2)</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C13—C8</td><td rowspan="1" colspan="1">1.1 (2)</td><td rowspan="1" colspan="1">N5—C16—C17—C18</td><td rowspan="1" colspan="1">−179.26 (14)</td></tr><tr><td rowspan="1" colspan="1">N4—C12—C13—C8</td><td rowspan="1" colspan="1">−178.12 (13)</td><td rowspan="1" colspan="1">C16—C17—C18—C19</td><td rowspan="1" colspan="1">−0.6 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C13—C12</td><td rowspan="1" colspan="1">−0.1 (2)</td><td rowspan="1" colspan="1">C17—C18—C19—C14</td><td rowspan="1" colspan="1">−0.4 (2)</td></tr><tr><td rowspan="1" colspan="1">S2—C8—C13—C12</td><td rowspan="1" colspan="1">178.39 (11)</td><td rowspan="1" colspan="1">C15—C14—C19—C18</td><td rowspan="1" colspan="1">1.1 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—C7—S1—C1</td><td rowspan="1" colspan="1">1.13 (11)</td><td rowspan="1" colspan="1">S3—C14—C19—C18</td><td rowspan="1" colspan="1">−177.70 (11)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—S1—C1</td><td rowspan="1" colspan="1">−178.31 (12)</td><td rowspan="1" colspan="1">C15—C14—S3—O7</td><td rowspan="1" colspan="1">125.09 (11)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—S1—C7</td><td rowspan="1" colspan="1">179.43 (14)</td><td rowspan="1" colspan="1">C19—C14—S3—O7</td><td rowspan="1" colspan="1">−56.11 (12)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—S1—C7</td><td rowspan="1" colspan="1">−0.62 (10)</td><td rowspan="1" colspan="1">C15—C14—S3—O6</td><td rowspan="1" colspan="1">3.69 (13)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2—O2</td><td rowspan="1" colspan="1">−135.32 (11)</td><td rowspan="1" colspan="1">C19—C14—S3—O6</td><td rowspan="1" colspan="1">−177.51 (10)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2—O2</td><td rowspan="1" colspan="1">46.19 (13)</td><td rowspan="1" colspan="1">C15—C14—S3—O5</td><td rowspan="1" colspan="1">−116.72 (12)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2—O1</td><td rowspan="1" colspan="1">−1.39 (13)</td><td rowspan="1" colspan="1">C19—C14—S3—O5</td><td rowspan="1" colspan="1">62.08 (12)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2—O1</td><td rowspan="1" colspan="1">−179.89 (11)</td><td rowspan="1" colspan="1">C17—C16—N5—O9</td><td rowspan="1" colspan="1">−162.03 (16)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—S2—N3</td><td rowspan="1" colspan="1">113.16 (12)</td><td rowspan="1" colspan="1">C15—C16—N5—O9</td><td rowspan="1" colspan="1">17.8 (2)</td></tr><tr><td rowspan="1" colspan="1">C13—C8—S2—N3</td><td rowspan="1" colspan="1">−65.33 (12)</td><td rowspan="1" colspan="1">C17—C16—N5—O8</td><td rowspan="1" colspan="1">17.9 (2)</td></tr><tr><td rowspan="1" colspan="1">N2—C7—N1—C6</td><td rowspan="1" colspan="1">178.09 (12)</td><td rowspan="1" colspan="1">C15—C16—N5—O8</td><td rowspan="1" colspan="1">−162.28 (15)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—N1—C6</td><td rowspan="1" colspan="1">−1.34 (15)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e9278" sec-type="tablewraphbondslong"><label>2-[2-(3-Nitrobenzenesulfonyl)hydrazinyl]-1,3-benzothiazol-3-ium;
3-nitrobenzenesulfonate (III) </label><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e9287"><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···O6</td><td rowspan="1" colspan="1">0.841 (19)</td><td rowspan="1" colspan="1">1.888 (19)</td><td rowspan="1" colspan="1">2.7267 (15)</td><td rowspan="1" colspan="1">175.2 (17)</td></tr><tr><td rowspan="1" colspan="1">N2—H2···O5</td><td rowspan="1" colspan="1">0.826 (19)</td><td rowspan="1" colspan="1">1.92 (2)</td><td rowspan="1" colspan="1">2.7489 (16)</td><td rowspan="1" colspan="1">175.4 (18)</td></tr><tr><td rowspan="1" colspan="1">N3—H3···O7<sup>i</sup></td><td rowspan="1" colspan="1">0.869 (18)</td><td rowspan="1" colspan="1">1.968 (19)</td><td rowspan="1" colspan="1">2.8058 (16)</td><td rowspan="1" colspan="1">161.6 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—H2<italic>A</italic>···O7<sup>ii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.55</td><td rowspan="1" colspan="1">3.2510 (18)</td><td rowspan="1" colspan="1">130</td></tr><tr><td rowspan="1" colspan="1">C9—H9···O8<sup>iii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.58</td><td rowspan="1" colspan="1">3.487 (2)</td><td rowspan="1" colspan="1">161</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>; (ii) <italic>x</italic>+1, <italic>y</italic>, <italic>z</italic>; (iii) −<italic>x</italic>+1, −<italic>y</italic>, −<italic>z</italic>+1.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Behera, N. & Manivannan, V. (2017). <italic>ChemistrySelect</italic>, <bold>2</bold>, 11048–11054.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Day, A. C. & Whiting, M. C. (1970). <italic>Org. Synth.</italic><bold>50</bold>, 3–5.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Fun, H.-K., Ooi, C. W., Sarojini, B. K., Mohan, B. J. & Narayana, B. (2012<italic>a</italic>). <italic>Acta Cryst.</italic> E<bold>68</bold>, o691–o692.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Fun, H.-K., Quah, C. K., Sarojini, B. K., Mohan, B. J. & Narayana, B. (2012<italic>b</italic>). <italic>Acta Cryst.</italic> E<bold>68</bold>, o2459.</mixed-citation></ref><ref id="bb6"><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="bb7"><mixed-citation publication-type="other">Gulati, S., Wakode, S., Kaur, A. & Anand, K. (2017). <italic>World J. Pharm. Pharm Sci.</italic><bold>6</bold>, 1842–1869.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Hipparagi, S. M., Majumder, U. K., Parikshit, B., Geethavani, M. & Kumar, V. S. (2007). <italic>Orient. J. Chem.</italic><bold>23</bold>, 65–66.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Katava, R., Pavelić, S. K., Harej, A., Hrenar, T. & Pavlović, G. (2017). <italic>Struct. Chem.</italic><bold>28</bold>, 709–721.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Liu, C. T., Wang, F., Xiao, T., Chi, B., Wu, Y. H., Zhu, D.-R. & Chen, X. Q. (2018). <italic>Sens. 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Rigaku Corporation, Tokyo, Japan.</mixed-citation></ref><ref id="bb16"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb17"><mixed-citation publication-type="other">Sheldrick, G. M. (2015). <italic>Acta Cryst.</italic> C<bold>71</bold>, 3–8.</mixed-citation></ref><ref id="bb18"><mixed-citation publication-type="other">Westrip, S. P. (2010). <italic>J. Appl. Cryst.</italic><bold>43</bold>, 920–925.</mixed-citation></ref></ref-list></back><floats-group><fig id="fig1" orientation="portrait" position="float"><label>Figure 1</label><caption><p>The asymmetric unit of (I)<xref ref-type="chem" rid="scheme1"></xref> showing 50% displacement ellipsoids. Hydrogen bonds are indicated by double-dashed lines.</p></caption><graphic xlink:href="e-74-00673-fig1"></graphic></fig><fig id="fig2" orientation="portrait" position="float"><label>Figure 2</label><caption><p>The asymmetric unit of (II)<xref ref-type="chem" rid="scheme1"></xref> showing 50% displacement ellipsoids. Hydrogen bonds are indicated by double-dashed lines.</p></caption><graphic xlink:href="e-74-00673-fig2"></graphic></fig><fig id="fig3" orientation="portrait" position="float"><label>Figure 3</label><caption><p>The asymmetric unit of (III)<xref ref-type="chem" rid="scheme1"></xref> showing 50% displacement ellipsoids. Hydrogen bonds are indicated by double-dashed lines.</p></caption><graphic xlink:href="e-74-00673-fig3"></graphic></fig><fig id="fig4" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Detail of the extended structure of (I)<xref ref-type="chem" rid="scheme1"></xref> showing π–π stacking between inversion-related thiazole rings and possible secondary N⋯π interactions. Symmetry code: (i) −x, 1 − y, 1 − z.</p></caption><graphic xlink:href="e-74-00673-fig4"></graphic></fig><fig id="fig5" orientation="portrait" position="float"><label>Figure 5</label><caption><p>Fragment of a [<inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>1<inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>] hydrogen-bonded chain in (II)<xref ref-type="chem" rid="scheme1"></xref> with the N—H⋯N and N—H⋯O bonds shown as blue and red double-dashed lines, respectively. All C-bonded hydrogen atoms have been omitted for clarity. Symmetry codes: (i) −<italic>x</italic>, 1 − <italic>y</italic>, −z; (ii) 1 − <italic>x</italic>, −<italic>y</italic>, 1 − <italic>z</italic>.</p></caption><graphic xlink:href="e-74-00673-fig5"></graphic></fig><fig id="fig6" orientation="portrait" position="float"><label>Figure 6</label><caption><p>An inversion-generated tetramer in the crystal of (III)<xref ref-type="chem" rid="scheme1"></xref>. Symmetry code: (i) 1 − <italic>x</italic>, 1 − <italic>y</italic>, −<italic>z</italic>.</p></caption><graphic xlink:href="e-74-00673-fig6"></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⋯O1</td><td rowspan="1" colspan="1" align="left" valign="top">0.86 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">1.87 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">2.721 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">167 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2⋯O2</td><td rowspan="1" colspan="1" align="left" valign="top">0.82 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">1.96 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">2.773 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">169 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C3—H3⋯O2<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.51</td><td rowspan="1" colspan="1" align="left" valign="top">3.415 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">160</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C4—H4⋯O4<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.55</td><td rowspan="1" colspan="1" align="left" valign="top">3.292 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">135</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C10—H10<italic>B</italic>⋯O4<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.98</td><td rowspan="1" colspan="1" align="left" valign="top">2.54</td><td rowspan="1" colspan="1" align="left" valign="top">3.297 (5)</td><td rowspan="1" colspan="1" align="left" valign="top">134</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C15—H15⋯O3<sup>iv</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.50</td><td rowspan="1" colspan="1" align="left" valign="top">3.315 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">144</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-74-00673-efi9.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-74-00673-efi10.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-74-00673-efi11.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iv) <inline-formula><inline-graphic xlink:href="e-74-00673-efi12.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">N2—H2⋯N5</td><td rowspan="1" colspan="1" align="left" valign="top">0.816 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">2.033 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">2.8447 (15)</td><td rowspan="1" colspan="1" align="left" valign="top">172.7 (16)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3—H3⋯O3<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.848 (17)</td><td rowspan="1" colspan="1" align="left" valign="top">2.129 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">2.9427 (15)</td><td rowspan="1" colspan="1" align="left" valign="top">160.8 (15)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N6—H6⋯N1</td><td rowspan="1" colspan="1" align="left" valign="top">0.820 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">2.050 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">2.8601 (15)</td><td rowspan="1" colspan="1" align="left" valign="top">169.2 (17)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N7—H7⋯O7<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.871 (17)</td><td rowspan="1" colspan="1" align="left" valign="top">2.123 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">2.9472 (15)</td><td rowspan="1" colspan="1" align="left" valign="top">157.6 (15)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C15—H15⋯O3<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.65</td><td rowspan="1" colspan="1" align="left" valign="top">3.4888 (17)</td><td rowspan="1" colspan="1" align="left" valign="top">147</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C26—H26⋯O2</td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.44</td><td rowspan="1" colspan="1" align="left" valign="top">3.1774 (16)</td><td rowspan="1" colspan="1" align="left" valign="top">134</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C5—H5⋯O1<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.66</td><td rowspan="1" colspan="1" align="left" valign="top">3.3218 (16)</td><td rowspan="1" colspan="1" align="left" valign="top">127</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C13—H13⋯O6</td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.56</td><td rowspan="1" colspan="1" align="left" valign="top">3.2731 (16)</td><td rowspan="1" colspan="1" align="left" valign="top">133</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-74-00673-efi13.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-74-00673-efi14.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-74-00673-efi15.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⋯O6</td><td rowspan="1" colspan="1" align="left" valign="top">0.841 (19)</td><td rowspan="1" colspan="1" align="left" valign="top">1.888 (19)</td><td rowspan="1" colspan="1" align="left" valign="top">2.7267 (15)</td><td rowspan="1" colspan="1" align="left" valign="top">175.2 (17)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2⋯O5</td><td rowspan="1" colspan="1" align="left" valign="top">0.826 (19)</td><td rowspan="1" colspan="1" align="left" valign="top">1.92 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">2.7489 (16)</td><td rowspan="1" colspan="1" align="left" valign="top">175.4 (18)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3—H3⋯O7<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.869 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">1.968 (19)</td><td rowspan="1" colspan="1" align="left" valign="top">2.8058 (16)</td><td rowspan="1" colspan="1" align="left" valign="top">161.6 (16)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C2—H2<italic>A</italic>⋯O7<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.55</td><td rowspan="1" colspan="1" align="left" valign="top">3.2510 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">130</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C9—H9⋯O8<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.58</td><td rowspan="1" colspan="1" align="left" valign="top">3.487 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">161</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-74-00673-efi10.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-74-00673-efi12.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-74-00673-efi14.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>Experimental details</title></caption><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>10</sub>H<sub>12</sub>N<sub>3</sub>S<sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<sup>−</sup></td><td rowspan="1" colspan="1" align="left" valign="top">C<sub>13</sub>H<sub>10</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub></td><td rowspan="1" colspan="1" align="left" valign="top">C<sub>13</sub>H<sub>11</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub><sup>+</sup>·C<sub>6</sub>H<sub>4</sub>NO<sub>5</sub>S<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">408.45</td><td rowspan="1" colspan="1" align="left" valign="top">350.37</td><td rowspan="1" colspan="1" align="left" valign="top">553.54</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">Triclinic, <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></td><td rowspan="1" colspan="1" align="left" valign="top">Triclinic, <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></td><td rowspan="1" colspan="1" align="left" valign="top">Triclinic, <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-00673-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td><td rowspan="1" colspan="1" align="left" valign="top">100</td><td rowspan="1" colspan="1" align="left" valign="top">100</td><td rowspan="1" colspan="1" align="left" valign="top">100</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">7.5308 (4), 10.9167 (7), 12.4438 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">6.83537 (15), 13.5788 (3), 15.6907 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">10.0399 (5), 10.7585 (4), 11.3372 (6)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">α, β, γ (°)</td><td rowspan="1" colspan="1" align="left" valign="top">66.058 (6), 79.034 (5), 72.156 (5)</td><td rowspan="1" colspan="1" align="left" valign="top">99.382 (2), 98.2324 (19), 91.9841 (19)</td><td rowspan="1" colspan="1" align="left" valign="top">85.607 (4), 71.369 (5), 77.115 (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">887.47 (10)</td><td rowspan="1" colspan="1" align="left" valign="top">1419.55 (6)</td><td rowspan="1" colspan="1" align="left" valign="top">1131.16 (10)</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">4</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><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">0.34</td><td rowspan="1" colspan="1" align="left" valign="top">0.40</td><td rowspan="1" colspan="1" align="left" valign="top">0.39</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">0.06 × 0.05 × 0.01</td><td rowspan="1" colspan="1" align="left" valign="top">0.15 × 0.10 × 0.03</td><td rowspan="1" colspan="1" align="left" valign="top">0.23 × 0.18 × 0.04</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 Mercury CCD</td><td rowspan="1" colspan="1" align="left" valign="top">Rigaku Mercury CCD</td><td rowspan="1" colspan="1" align="left" valign="top">Rigaku Mercury CCD</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>FS_ABSCOR</italic>; Rigaku, 2013<xref ref-type="bibr" rid="bb15"> ▸</xref>)</td><td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>FS_ABSCOR</italic>; Rigaku, 2013<xref ref-type="bibr" rid="bb15"> ▸</xref>)</td><td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>FS_ABSCOR</italic>; Rigaku, 2013<xref ref-type="bibr" rid="bb15"> ▸</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">0.614, 1.000</td><td rowspan="1" colspan="1" align="left" valign="top">0.861, 1.000</td><td rowspan="1" colspan="1" align="left" valign="top">0.879, 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">11341, 3490, 3249</td><td rowspan="1" colspan="1" align="left" valign="top">24032, 6465, 6033</td><td rowspan="1" colspan="1" align="left" valign="top">19781, 5159, 4880</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">0.036</td><td rowspan="1" colspan="1" align="left" valign="top">0.018</td><td rowspan="1" colspan="1" align="left" valign="top">0.017</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">0.617</td><td rowspan="1" colspan="1" align="left" valign="top">0.649</td><td rowspan="1" colspan="1" align="left" valign="top">0.651</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">0.066, 0.184, 1.11</td><td rowspan="1" colspan="1" align="left" valign="top">0.027, 0.072, 1.04</td><td rowspan="1" colspan="1" align="left" valign="top">0.029, 0.076, 1.02</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">3490</td><td rowspan="1" colspan="1" align="left" valign="top">6465</td><td rowspan="1" colspan="1" align="left" valign="top">5159</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">250</td><td rowspan="1" colspan="1" align="left" valign="top">427</td><td rowspan="1" colspan="1" align="left" valign="top">334</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">1.32, −0.63</td><td rowspan="1" colspan="1" align="left" valign="top">0.40, −0.38</td><td rowspan="1" colspan="1" align="left" valign="top">0.39, −0.42</td></tr></tbody></table><table-wrap-foot><p>Computer programs: <italic>CrystalClear</italic> (Rigaku, 2012<xref ref-type="bibr" rid="bb14"> ▸</xref>), <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb16"> ▸</xref>), <italic>SHELXL2014</italic> (Sheldrick, 2015<xref ref-type="bibr" rid="bb17"> ▸</xref>), <italic>ORTEP-3 for Windows</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb3"> ▸</xref>) and <italic>publCIF</italic> (Westrip, 2010<xref ref-type="bibr" rid="bb18"> ▸</xref>).</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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