MersV1, Pmc, Corpus, bibRecord, 000A06

4-(4-Chlorophenyl)piperidin-4-ol

Identifieur interne : 000A06 ( Pmc/Corpus ); précédent : 000A05; suivant : 000A07

4-(4-Chlorophenyl)piperidin-4-ol

Auteurs : Grzegorz Dutkiewicz ; B. P. Siddaraju ; H. S. Yathirajan ; M. S. Siddegowda ; Maciej Kubicki

Source :

Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2010.

RBID : PMC:2983646

Abstract

In the title compound, C₁₁H₁₄ClNO, the piperidine ring adopts a chair conformation: the hydroxyl substituent and the N-bound H atom occupy the axial positions, while the benzene ring occupies the equatorial position. In the crystal, the molecules are linked into a centrosymmetric tetramer through strong O—H⋯N and weak N—H⋯O hydrogen bonds; the N and O atoms act as both donor and acceptor for these interactions. The tetramers are further joined by hydrogen bonds into a layer parallel to (100).

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983646

DOI: 10.1107/S1600536810004216
PubMed: 21580330
PubMed Central: 2983646

Links to Exploration step

PMC:2983646

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">4-(4-Chlorophenyl)piperidin-4-ol</title>
<author><name sortKey="Dutkiewicz, Grzegorz" sort="Dutkiewicz, Grzegorz" uniqKey="Dutkiewicz G" first="Grzegorz" last="Dutkiewicz">Grzegorz Dutkiewicz</name>
<affiliation><nlm:aff id="a">Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań,<country>Poland</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Siddaraju, B P" sort="Siddaraju, B P" uniqKey="Siddaraju B" first="B. P." last="Siddaraju">B. P. Siddaraju</name>
<affiliation><nlm:aff id="b">Department of Chemistry, V. V. Puram College of Science, Bangalore 560 004,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Yathirajan, H S" sort="Yathirajan, H S" uniqKey="Yathirajan H" first="H. S." last="Yathirajan">H. S. Yathirajan</name>
<affiliation><nlm:aff id="c">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Siddegowda, M S" sort="Siddegowda, M S" uniqKey="Siddegowda M" first="M. S." last="Siddegowda">M. S. Siddegowda</name>
<affiliation><nlm:aff id="c">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Kubicki, Maciej" sort="Kubicki, Maciej" uniqKey="Kubicki M" first="Maciej" last="Kubicki">Maciej Kubicki</name>
<affiliation><nlm:aff id="a">Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań,<country>Poland</country>
</nlm:aff>
</affiliation>
</author>
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<publicationStmt><idno type="wicri:source">PMC</idno>
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<idno type="doi">10.1107/S1600536810004216</idno>
<date when="2010">2010</date>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">4-(4-Chlorophenyl)piperidin-4-ol</title>
<author><name sortKey="Dutkiewicz, Grzegorz" sort="Dutkiewicz, Grzegorz" uniqKey="Dutkiewicz G" first="Grzegorz" last="Dutkiewicz">Grzegorz Dutkiewicz</name>
<affiliation><nlm:aff id="a">Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań,<country>Poland</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Siddaraju, B P" sort="Siddaraju, B P" uniqKey="Siddaraju B" first="B. P." last="Siddaraju">B. P. Siddaraju</name>
<affiliation><nlm:aff id="b">Department of Chemistry, V. V. Puram College of Science, Bangalore 560 004,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Yathirajan, H S" sort="Yathirajan, H S" uniqKey="Yathirajan H" first="H. S." last="Yathirajan">H. S. Yathirajan</name>
<affiliation><nlm:aff id="c">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Siddegowda, M S" sort="Siddegowda, M S" uniqKey="Siddegowda M" first="M. S." last="Siddegowda">M. S. Siddegowda</name>
<affiliation><nlm:aff id="c">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006,<country>India</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Kubicki, Maciej" sort="Kubicki, Maciej" uniqKey="Kubicki M" first="Maciej" last="Kubicki">Maciej Kubicki</name>
<affiliation><nlm:aff id="a">Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań,<country>Poland</country>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title>
<idno type="eISSN">1600-5368</idno>
<imprint><date when="2010">2010</date>
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<front><div type="abstract" xml:lang="en"><p>In the title compound, C<sub>11</sub>
H<sub>14</sub>
ClNO, the piperidine ring adopts a chair conformation: the hydroxyl substituent and the N-bound H atom occupy the axial positions, while the benzene ring occupies the equatorial position. In the crystal, the molecules are linked into a centrosymmetric tetramer through strong O—H⋯N and weak N—H⋯O hydrogen bonds; the N and O atoms act as both donor and acceptor for these interactions. The tetramers are further joined by hydrogen bonds into a layer parallel to (100).</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
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</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 Sect E Struct Rep Online</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title>
</journal-title-group>
<issn pub-type="epub">1600-5368</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">21580330</article-id>
<article-id pub-id-type="pmc">2983646</article-id>
<article-id pub-id-type="publisher-id">is2520</article-id>
<article-id pub-id-type="doi">10.1107/S1600536810004216</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536810004216</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>4-(4-Chlorophenyl)piperidin-4-ol</article-title>
<alt-title><italic>C<sub>11</sub>
H<sub>14</sub>
ClNO</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Dutkiewicz</surname>
<given-names>Grzegorz</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Siddaraju</surname>
<given-names>B. P.</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Yathirajan</surname>
<given-names>H. S.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Siddegowda</surname>
<given-names>M. S.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Kubicki</surname>
<given-names>Maciej</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, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań,<country>Poland</country>
</aff>
<aff id="b"><label>b</label>
Department of Chemistry, V. V. Puram College of Science, Bangalore 560 004,<country>India</country>
</aff>
<aff id="c"><label>c</label>
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006,<country>India</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>mkubicki@amu.edu.pl</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>3</month>
<year>2010</year>
</pub-date>
<pub-date pub-type="epub"><day>06</day>
<month>2</month>
<year>2010</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>06</day>
<month>2</month>
<year>2010</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the 
 							. </pmc-comment>
      <volume>66</volume>
<issue>Pt 3</issue>
<issue-id pub-id-type="publisher-id">e100300</issue-id>
<fpage>o562</fpage>
<lpage>o562</lpage>
<history><date date-type="received"><day>28</day>
<month>1</month>
<year>2010</year>
</date>
<date date-type="accepted"><day>02</day>
<month>2</month>
<year>2010</year>
</date>
</history>
<permissions><copyright-statement>© Dutkiewicz et al. 2010</copyright-statement>
<copyright-year>2010</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 Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
</license>
</permissions>
<self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536810004216">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>In the title compound, C<sub>11</sub>
H<sub>14</sub>
ClNO, the piperidine ring adopts a chair conformation: the hydroxyl substituent and the N-bound H atom occupy the axial positions, while the benzene ring occupies the equatorial position. In the crystal, the molecules are linked into a centrosymmetric tetramer through strong O—H⋯N and weak N—H⋯O hydrogen bonds; the N and O atoms act as both donor and acceptor for these interactions. The tetramers are further joined by hydrogen bonds into a layer parallel to (100).</p>
</abstract>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature</title>
<p>For related structures, see: De Camp & Ahmed (1972<italic>a</italic>
<xref ref-type="bibr" rid="bb3"> ▶</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb4"> ▶</xref>
); Friederich <italic>et al.</italic>
 (1993<xref ref-type="bibr" rid="bb6"> ▶</xref>
); Kimura & Okabayashi (1986<xref ref-type="bibr" rid="bb7"> ▶</xref>
). For details of the asymmetry parameters for chair conformations, see: Duax & Norton (1975<xref ref-type="bibr" rid="bb5"> ▶</xref>
). For a description of the Cambridge Structural Database, see: Allen (2002<xref ref-type="bibr" rid="bb1"> ▶</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-66-0o562-scheme1.jpg" position="float"></graphic>
</chem-struct>
</p>
</sec>
<sec sec-type="" id="sec2"><title>Experimental</title>
<sec id="sec2.1"><title></title>
<sec id="sec2.1.1"><title>Crystal data</title>
<p><list list-type="simple"><list-item><p>C<sub>11</sub>
H<sub>14</sub>
ClNO</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 211.68</p>
</list-item>
<list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-66-0o562-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
 = 11.3706 (10) Å</p>
</list-item>
<list-item><p><italic>b</italic>
 = 9.5204 (8) Å</p>
</list-item>
<list-item><p><italic>c</italic>
 = 10.6164 (9) Å</p>
</list-item>
<list-item><p>β = 108.458 (8)°</p>
</list-item>
<list-item><p><italic>V</italic>
 = 1090.13 (16) Å<sup>3</sup>
</p>
</list-item>
<list-item><p><italic>Z</italic>
 = 4</p>
</list-item>
<list-item><p>Cu <italic>K</italic>
α radiation</p>
</list-item>
<list-item><p>μ = 2.83 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
 = 295 K</p>
</list-item>
<list-item><p>0.3 × 0.2 × 0.15 mm</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.1.2"><title>Data collection</title>
<p><list list-type="simple"><list-item><p>Oxford Diffraction SuperNova, single source at offset, Atlas diffractometer</p>
</list-item>
<list-item><p>Absorption correction: multi-scan (<italic>CrysAlis PRO</italic>
; Oxford Diffraction, 2009<xref ref-type="bibr" rid="bb9"> ▶</xref>
) <italic>T</italic>
<sub>min</sub>
 = 0.401, <italic>T</italic>
<sub>max</sub>
 = 0.654</p>
</list-item>
<list-item><p>4068 measured reflections</p>
</list-item>
<list-item><p>2190 independent reflections</p>
</list-item>
<list-item><p>2014 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</p>
</list-item>
<list-item><p><italic>R</italic>
<sub>int</sub>
 = 0.011</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.1.3"><title>Refinement</title>
<p><list list-type="simple"><list-item><p><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.038</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.111</p>
</list-item>
<list-item><p><italic>S</italic>
 = 1.07</p>
</list-item>
<list-item><p>2190 reflections</p>
</list-item>
<list-item><p>183 parameters</p>
</list-item>
<list-item><p>H atoms treated by a mixture of independent and constrained refinement</p>
</list-item>
<list-item><p>Δρ<sub>max</sub>
 = 0.32 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
 = −0.38 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
</sec>
<sec id="d5e474"><title></title>
<p>Data collection: <italic>CrysAlis PRO</italic>
 (Oxford Diffraction, 2009<xref ref-type="bibr" rid="bb9"> ▶</xref>
); cell refinement: <italic>CrysAlis PRO</italic>
; data reduction: <italic>CrysAlis PRO</italic>
; program(s) used to solve structure: <italic>SIR92</italic>
 (Altomare <italic>et al.</italic>
, 1993<xref ref-type="bibr" rid="bb2"> ▶</xref>
); program(s) used to refine structure: <italic>SHELXL97</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb10"> ▶</xref>
); molecular graphics: <italic>Stereochemical Workstation Operation Manual</italic>
 (Siemens, 1989<xref ref-type="bibr" rid="bb11"> ▶</xref>
) and <italic>Mercury</italic>
 (Macrae <italic>et al.</italic>
, 2008<xref ref-type="bibr" rid="bb8"> ▶</xref>
); software used to prepare material for publication: <italic>SHELXL97</italic>
.</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data" xlink:href="e-66-0o562-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablocks I, global. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536810004216/is2520sup1.cif">10.1107/S1600536810004216/is2520sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-66-0o562-sup1.cif" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material content-type="local-data" xlink:href="e-66-0o562-Isup2.hkl" position="float" xlink:type="simple"><p>Structure factors: contains datablocks I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536810004216/is2520Isup2.hkl">10.1107/S1600536810004216/is2520Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-66-0o562-Isup2.hkl" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material position="float" xlink:type="simple"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?is2520&file=is2520sup0.html&mime=text/html" xlink:type="simple"> crystallographic information</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?is2520sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?is2520&checkcif=yes" xlink:type="simple">checkCIF report</ext-link>
</p>
</supplementary-material>
</sec>
</body>
<back><fn-group><fn id="fnu1"><p>Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsup?is2520">IS2520</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>BPS thanks R. L. FineChem, Bangalore, India, for the gift of a sample of the title compound.</p>
</ack>
<app-group><app><title>supplementary crystallographic 
information</title>
<sec id="comment"><title>Comment </title>
<p>The title compound, (1, Scheme 1), 4-(4-chlorophenyl)piperidin-4-ol is
used as an intermediate for the synthesis of pharmaceuticals such as
haloperidol (neuroleptic drug used to treat psychotic illnesses, extreme
agitation, or Tourette's syndrome) and loperamide which is effective against
diarrhea resulting from gastroenteritis or inflammatory bowel disease.</p>
<p>The piperidine ring adopts an almost ideal chair conformation (Fig. 1); the
asymmetry parameters (Duax & Norton, 1975) are all smaller than 2.5°.
The
hydroxy group and N—H hydrogen atom occupy the axial positions [torsion
angles: C2—C3—C4—O4 -64.46 (15)°, C6—C5—C4—O4 60.81 (15)°,
C5—C6—N1—H1 65.0 (13)°, and C3—C2—N1—H1 -64.8 (14)°]. Such a
mutual conformation of hydroxyl and phenyl groups is very typical, in the
Cambridge Database (Allen, 2002; ver. 5.30 of Nov. 2008, last update
Sep.
2009) there are 65 crystal structures of six-membered saturated rings with
both OH and aromatic substituent in one position, only in three of them the
hydroxyl group adopts the equatorial position [two polymorphs of
(±)-β-1,2,5-trimethyl-4-phenylpiperidin-4-ol (De Camp & Ahmed,
1972<italic>a</italic>
,<italic>b</italic>),
cis-1,4-bis(4-bromophenyl)-1,4-dimethoxycyclohexane
(Friederich <italic>et al.</italic>, 1993), and
cis-1-phenyl-3-piperidinocyclohexan-1-ol
hydrochloride (Kimura & Okabayashi, 1986)].</p>
<p>The relatively strong and directional O—H···N hydrogen bonds join the
molecules of 1, related by two-fold screw axis, into the chains along
[010] directions. These chains are interconnected by far weaker N—H···O
hydrogen bonds. These two kinds of contacts form centrosymmetric tetramers of
the molecules (Fig. 2). In the crystal structures there are the
hydrogen-bonded layers of molecules, created by interconnecting chains, in the
<italic>bc</italic> plane (Fig. 3a). There are no directional interactions between
neighbouring layers (Fig. 3b).</p>
</sec>
<sec id="experimental"><title>Experimental </title>
<p>The title compound was obtained as a gift sample from R. L. Fine Chem,
Bangalore, India. X-ray quality crystals were obtained by a slow evaporation
from an ethyl acetate solution (m.p. 410–413 K).</p>
</sec>
<sec id="refinement"><title>Refinement </title>
<p>Hydrogen atoms were found in the subsequent difference Fourier maps, and freely
refined.</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>Anisotropic ellipsoid representation of the compound 1 together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii.</p>
</caption>
<graphic xlink:href="e-66-0o562-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>Hydrogen-bonded tetramer [symmetry codes: (i) x, 1/2 - y, 1/2 + z; (ii) 2 - x, 1 - y, 1 - z; (iii) 2 - x, 1/2 + y, 1/2 - z].</p>
</caption>
<graphic xlink:href="e-66-0o562-fig2"></graphic>
</fig>
<fig id="Fap3"><label>Fig. 3.</label>
<caption><p>The packing of the molecules of 1. (a) Hydrogen-boded layer; (b) the packing as seen along the y-direction.</p>
</caption>
<graphic xlink:href="e-66-0o562-fig3"></graphic>
</fig>
</sec>
<sec id="tablewrapcrystaldatalong"><title>Crystal data</title>
<table-wrap position="anchor" id="d1e161"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C<sub>11</sub>
H<sub>14</sub>
ClNO</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 448</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 211.68</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.290 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Cu <italic>K</italic>
α radiation, λ = 1.54178 Å</td>
</tr>
<tr><td rowspan="1" colspan="1">Hall symbol:  -P 2ybc</td>
<td rowspan="1" colspan="1">Cell parameters from 3304 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 11.3706 (10) Å</td>
<td rowspan="1" colspan="1">θ = 4.1–75.2°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 9.5204 (8) Å</td>
<td rowspan="1" colspan="1">µ = 2.83 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 10.6164 (9) Å</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 295 K</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 108.458 (8)°</td>
<td rowspan="1" colspan="1">Prism, yellow</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 1090.13 (16)  Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.3 × 0.2 × 0.15 mm</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 4</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapdatacollectionlong"><title>Data collection</title>
<table-wrap position="anchor" id="d1e286"><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">Oxford Diffraction SuperNova, single source at offset, Atlas diffractometer</td>
<td rowspan="1" colspan="1">2190 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: SuperNova (Cu) X-ray Source</td>
<td rowspan="1" colspan="1">2014 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">mirror</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.011</td>
</tr>
<tr><td rowspan="1" colspan="1">Detector resolution: 10.5357 pixels mm<sup>-1</sup>
</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 75.3°, θ<sub>min</sub>
 = 4.1°</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −13→14</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>CrysAlis PRO</italic>
; Oxford Diffraction, 2009)</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −11→7</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.401, <italic>T</italic>
<sub>max</sub>
 = 0.654</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −12→13</td>
</tr>
<tr><td rowspan="1" colspan="1">4068 measured reflections</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraprefinementdatalong"><title>Refinement</title>
<table-wrap position="anchor" id="d1e406"><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">Secondary atom site location: difference Fourier map</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.038</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.111</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>S</italic>
 = 1.07</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0549<italic>P</italic>
)<sup>2</sup>
 + 0.250<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">2190 reflections</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 < 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1">183 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.32 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">0 restraints</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.38 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e563"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.</td>
</tr>
<tr><td rowspan="1" colspan="1">Refinement. Refinement of <italic>F</italic>
<sup>2</sup>
 against ALL reflections. The weighted <italic>R</italic>-factor
wR and goodness of fit <italic>S</italic>
 are based on <italic>F</italic>
<sup>2</sup>, conventional
<italic>R</italic>
-factors <italic>R</italic>
 are based on <italic>F</italic>
, with <italic>F</italic> set to zero for
negative <italic>F</italic>
<sup>2</sup>
. The threshold expression of <italic>F</italic>
<sup>2</sup> >
2σ(<italic>F</italic>
<sup>2</sup>
) is used only for calculating <italic>R</italic>-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. <italic>R</italic>-factors
based on <italic>F</italic>
<sup>2</sup> are statistically about twice as large as those based on
<italic>F</italic>
, and <italic>R</italic>
- factors based on ALL data will be even larger.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapcoords"><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e655"><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">N1</td>
<td rowspan="1" colspan="1">0.92832 (13)</td>
<td rowspan="1" colspan="1">0.42199 (14)</td>
<td rowspan="1" colspan="1">0.33836 (13)</td>
<td rowspan="1" colspan="1">0.0530 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1</td>
<td rowspan="1" colspan="1">0.8930 (19)</td>
<td rowspan="1" colspan="1">0.430 (2)</td>
<td rowspan="1" colspan="1">0.402 (2)</td>
<td rowspan="1" colspan="1">0.069 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.83116 (16)</td>
<td rowspan="1" colspan="1">0.40784 (17)</td>
<td rowspan="1" colspan="1">0.20917 (16)</td>
<td rowspan="1" colspan="1">0.0537 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21</td>
<td rowspan="1" colspan="1">0.8738 (17)</td>
<td rowspan="1" colspan="1">0.4069 (19)</td>
<td rowspan="1" colspan="1">0.1413 (18)</td>
<td rowspan="1" colspan="1">0.058 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22</td>
<td rowspan="1" colspan="1">0.7767 (18)</td>
<td rowspan="1" colspan="1">0.491 (2)</td>
<td rowspan="1" colspan="1">0.1973 (18)</td>
<td rowspan="1" colspan="1">0.065 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.75467 (14)</td>
<td rowspan="1" colspan="1">0.27404 (16)</td>
<td rowspan="1" colspan="1">0.19461 (16)</td>
<td rowspan="1" colspan="1">0.0507 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H31</td>
<td rowspan="1" colspan="1">0.7086 (19)</td>
<td rowspan="1" colspan="1">0.277 (2)</td>
<td rowspan="1" colspan="1">0.255 (2)</td>
<td rowspan="1" colspan="1">0.072 (6)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H32</td>
<td rowspan="1" colspan="1">0.6977 (17)</td>
<td rowspan="1" colspan="1">0.2675 (19)</td>
<td rowspan="1" colspan="1">0.0997 (19)</td>
<td rowspan="1" colspan="1">0.061 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.83678 (12)</td>
<td rowspan="1" colspan="1">0.14272 (14)</td>
<td rowspan="1" colspan="1">0.22350 (12)</td>
<td rowspan="1" colspan="1">0.0414 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.89540 (10)</td>
<td rowspan="1" colspan="1">0.13797 (11)</td>
<td rowspan="1" colspan="1">0.12224 (9)</td>
<td rowspan="1" colspan="1">0.0476 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4A</td>
<td rowspan="1" colspan="1">0.949 (2)</td>
<td rowspan="1" colspan="1">0.073 (2)</td>
<td rowspan="1" colspan="1">0.140 (2)</td>
<td rowspan="1" colspan="1">0.074 (6)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.93538 (14)</td>
<td rowspan="1" colspan="1">0.16101 (17)</td>
<td rowspan="1" colspan="1">0.36010 (13)</td>
<td rowspan="1" colspan="1">0.0462 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H51</td>
<td rowspan="1" colspan="1">0.9930 (16)</td>
<td rowspan="1" colspan="1">0.0777 (19)</td>
<td rowspan="1" colspan="1">0.3783 (16)</td>
<td rowspan="1" colspan="1">0.052 (4)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H52</td>
<td rowspan="1" colspan="1">0.8963 (17)</td>
<td rowspan="1" colspan="1">0.1649 (19)</td>
<td rowspan="1" colspan="1">0.4293 (18)</td>
<td rowspan="1" colspan="1">0.058 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">1.00732 (15)</td>
<td rowspan="1" colspan="1">0.29679 (18)</td>
<td rowspan="1" colspan="1">0.36784 (15)</td>
<td rowspan="1" colspan="1">0.0534 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H61</td>
<td rowspan="1" colspan="1">1.0557 (17)</td>
<td rowspan="1" colspan="1">0.2932 (19)</td>
<td rowspan="1" colspan="1">0.3036 (18)</td>
<td rowspan="1" colspan="1">0.059 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H62</td>
<td rowspan="1" colspan="1">1.0676 (18)</td>
<td rowspan="1" colspan="1">0.307 (2)</td>
<td rowspan="1" colspan="1">0.457 (2)</td>
<td rowspan="1" colspan="1">0.066 (5)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C41</td>
<td rowspan="1" colspan="1">0.75873 (12)</td>
<td rowspan="1" colspan="1">0.01087 (15)</td>
<td rowspan="1" colspan="1">0.21490 (13)</td>
<td rowspan="1" colspan="1">0.0433 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C42</td>
<td rowspan="1" colspan="1">0.76509 (17)</td>
<td rowspan="1" colspan="1">−0.0736 (2)</td>
<td rowspan="1" colspan="1">0.32296 (16)</td>
<td rowspan="1" colspan="1">0.0604 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H42</td>
<td rowspan="1" colspan="1">0.818 (2)</td>
<td rowspan="1" colspan="1">−0.051 (2)</td>
<td rowspan="1" colspan="1">0.409 (2)</td>
<td rowspan="1" colspan="1">0.080 (6)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C43</td>
<td rowspan="1" colspan="1">0.69364 (19)</td>
<td rowspan="1" colspan="1">−0.1934 (2)</td>
<td rowspan="1" colspan="1">0.3105 (2)</td>
<td rowspan="1" colspan="1">0.0715 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H43</td>
<td rowspan="1" colspan="1">0.699 (2)</td>
<td rowspan="1" colspan="1">−0.251 (2)</td>
<td rowspan="1" colspan="1">0.384 (2)</td>
<td rowspan="1" colspan="1">0.084 (6)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C44</td>
<td rowspan="1" colspan="1">0.61247 (15)</td>
<td rowspan="1" colspan="1">−0.22890 (18)</td>
<td rowspan="1" colspan="1">0.18927 (19)</td>
<td rowspan="1" colspan="1">0.0600 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">Cl44</td>
<td rowspan="1" colspan="1">0.52022 (5)</td>
<td rowspan="1" colspan="1">−0.37870 (6)</td>
<td rowspan="1" colspan="1">0.17414 (7)</td>
<td rowspan="1" colspan="1">0.0901 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C45</td>
<td rowspan="1" colspan="1">0.60313 (16)</td>
<td rowspan="1" colspan="1">−0.14761 (19)</td>
<td rowspan="1" colspan="1">0.07924 (18)</td>
<td rowspan="1" colspan="1">0.0601 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H45</td>
<td rowspan="1" colspan="1">0.550 (2)</td>
<td rowspan="1" colspan="1">−0.174 (2)</td>
<td rowspan="1" colspan="1">−0.007 (2)</td>
<td rowspan="1" colspan="1">0.081 (6)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C46</td>
<td rowspan="1" colspan="1">0.67646 (14)</td>
<td rowspan="1" colspan="1">−0.02996 (18)</td>
<td rowspan="1" colspan="1">0.09244 (15)</td>
<td rowspan="1" colspan="1">0.0536 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H46</td>
<td rowspan="1" colspan="1">0.6735 (18)</td>
<td rowspan="1" colspan="1">0.028 (2)</td>
<td rowspan="1" colspan="1">0.014 (2)</td>
<td rowspan="1" colspan="1">0.072 (6)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e1049"><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">N1</td>
<td rowspan="1" colspan="1">0.0619 (8)</td>
<td rowspan="1" colspan="1">0.0540 (7)</td>
<td rowspan="1" colspan="1">0.0485 (7)</td>
<td rowspan="1" colspan="1">−0.0073 (6)</td>
<td rowspan="1" colspan="1">0.0250 (6)</td>
<td rowspan="1" colspan="1">−0.0050 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0587 (9)</td>
<td rowspan="1" colspan="1">0.0478 (8)</td>
<td rowspan="1" colspan="1">0.0548 (8)</td>
<td rowspan="1" colspan="1">0.0021 (7)</td>
<td rowspan="1" colspan="1">0.0181 (7)</td>
<td rowspan="1" colspan="1">0.0037 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0468 (7)</td>
<td rowspan="1" colspan="1">0.0509 (8)</td>
<td rowspan="1" colspan="1">0.0539 (8)</td>
<td rowspan="1" colspan="1">0.0038 (6)</td>
<td rowspan="1" colspan="1">0.0152 (6)</td>
<td rowspan="1" colspan="1">0.0030 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0446 (7)</td>
<td rowspan="1" colspan="1">0.0485 (7)</td>
<td rowspan="1" colspan="1">0.0339 (6)</td>
<td rowspan="1" colspan="1">0.0023 (5)</td>
<td rowspan="1" colspan="1">0.0163 (5)</td>
<td rowspan="1" colspan="1">0.0033 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.0558 (6)</td>
<td rowspan="1" colspan="1">0.0550 (6)</td>
<td rowspan="1" colspan="1">0.0377 (5)</td>
<td rowspan="1" colspan="1">0.0044 (5)</td>
<td rowspan="1" colspan="1">0.0227 (4)</td>
<td rowspan="1" colspan="1">0.0064 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0492 (7)</td>
<td rowspan="1" colspan="1">0.0539 (8)</td>
<td rowspan="1" colspan="1">0.0356 (6)</td>
<td rowspan="1" colspan="1">−0.0010 (6)</td>
<td rowspan="1" colspan="1">0.0136 (5)</td>
<td rowspan="1" colspan="1">0.0032 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0508 (8)</td>
<td rowspan="1" colspan="1">0.0627 (9)</td>
<td rowspan="1" colspan="1">0.0451 (7)</td>
<td rowspan="1" colspan="1">−0.0073 (7)</td>
<td rowspan="1" colspan="1">0.0129 (6)</td>
<td rowspan="1" colspan="1">−0.0003 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C41</td>
<td rowspan="1" colspan="1">0.0435 (6)</td>
<td rowspan="1" colspan="1">0.0479 (7)</td>
<td rowspan="1" colspan="1">0.0407 (6)</td>
<td rowspan="1" colspan="1">0.0032 (6)</td>
<td rowspan="1" colspan="1">0.0167 (5)</td>
<td rowspan="1" colspan="1">0.0004 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C42</td>
<td rowspan="1" colspan="1">0.0649 (10)</td>
<td rowspan="1" colspan="1">0.0668 (10)</td>
<td rowspan="1" colspan="1">0.0459 (8)</td>
<td rowspan="1" colspan="1">−0.0133 (8)</td>
<td rowspan="1" colspan="1">0.0123 (7)</td>
<td rowspan="1" colspan="1">0.0086 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C43</td>
<td rowspan="1" colspan="1">0.0746 (11)</td>
<td rowspan="1" colspan="1">0.0722 (12)</td>
<td rowspan="1" colspan="1">0.0672 (10)</td>
<td rowspan="1" colspan="1">−0.0159 (9)</td>
<td rowspan="1" colspan="1">0.0216 (9)</td>
<td rowspan="1" colspan="1">0.0162 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C44</td>
<td rowspan="1" colspan="1">0.0495 (8)</td>
<td rowspan="1" colspan="1">0.0533 (9)</td>
<td rowspan="1" colspan="1">0.0805 (11)</td>
<td rowspan="1" colspan="1">−0.0037 (7)</td>
<td rowspan="1" colspan="1">0.0253 (8)</td>
<td rowspan="1" colspan="1">−0.0041 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">Cl44</td>
<td rowspan="1" colspan="1">0.0732 (3)</td>
<td rowspan="1" colspan="1">0.0695 (3)</td>
<td rowspan="1" colspan="1">0.1295 (5)</td>
<td rowspan="1" colspan="1">−0.0240 (2)</td>
<td rowspan="1" colspan="1">0.0349 (3)</td>
<td rowspan="1" colspan="1">−0.0071 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C45</td>
<td rowspan="1" colspan="1">0.0515 (8)</td>
<td rowspan="1" colspan="1">0.0656 (10)</td>
<td rowspan="1" colspan="1">0.0609 (9)</td>
<td rowspan="1" colspan="1">−0.0039 (7)</td>
<td rowspan="1" colspan="1">0.0145 (7)</td>
<td rowspan="1" colspan="1">−0.0124 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C46</td>
<td rowspan="1" colspan="1">0.0540 (8)</td>
<td rowspan="1" colspan="1">0.0600 (9)</td>
<td rowspan="1" colspan="1">0.0453 (7)</td>
<td rowspan="1" colspan="1">−0.0006 (7)</td>
<td rowspan="1" colspan="1">0.0138 (6)</td>
<td rowspan="1" colspan="1">−0.0004 (7)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title>
<table-wrap position="anchor" id="d1e1335"><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">N1—C6</td>
<td rowspan="1" colspan="1">1.465 (2)</td>
<td rowspan="1" colspan="1">C5—H52</td>
<td rowspan="1" colspan="1">0.972 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2</td>
<td rowspan="1" colspan="1">1.470 (2)</td>
<td rowspan="1" colspan="1">C6—H61</td>
<td rowspan="1" colspan="1">1.003 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1</td>
<td rowspan="1" colspan="1">0.89 (2)</td>
<td rowspan="1" colspan="1">C6—H62</td>
<td rowspan="1" colspan="1">0.99 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.522 (2)</td>
<td rowspan="1" colspan="1">C41—C42</td>
<td rowspan="1" colspan="1">1.384 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—H21</td>
<td rowspan="1" colspan="1">0.987 (19)</td>
<td rowspan="1" colspan="1">C41—C46</td>
<td rowspan="1" colspan="1">1.395 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—H22</td>
<td rowspan="1" colspan="1">0.99 (2)</td>
<td rowspan="1" colspan="1">C42—C43</td>
<td rowspan="1" colspan="1">1.382 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.5322 (19)</td>
<td rowspan="1" colspan="1">C42—H42</td>
<td rowspan="1" colspan="1">0.95 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H31</td>
<td rowspan="1" colspan="1">0.95 (2)</td>
<td rowspan="1" colspan="1">C43—C44</td>
<td rowspan="1" colspan="1">1.368 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H32</td>
<td rowspan="1" colspan="1">1.013 (18)</td>
<td rowspan="1" colspan="1">C43—H43</td>
<td rowspan="1" colspan="1">0.94 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—O4</td>
<td rowspan="1" colspan="1">1.4337 (15)</td>
<td rowspan="1" colspan="1">C44—C45</td>
<td rowspan="1" colspan="1">1.377 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C41</td>
<td rowspan="1" colspan="1">1.5233 (19)</td>
<td rowspan="1" colspan="1">C44—Cl44</td>
<td rowspan="1" colspan="1">1.7473 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.5365 (18)</td>
<td rowspan="1" colspan="1">C45—C46</td>
<td rowspan="1" colspan="1">1.377 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—H4A</td>
<td rowspan="1" colspan="1">0.84 (2)</td>
<td rowspan="1" colspan="1">C45—H45</td>
<td rowspan="1" colspan="1">0.96 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.518 (2)</td>
<td rowspan="1" colspan="1">C46—H46</td>
<td rowspan="1" colspan="1">0.99 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—H51</td>
<td rowspan="1" colspan="1">1.008 (17)</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—N1—C2</td>
<td rowspan="1" colspan="1">110.71 (12)</td>
<td rowspan="1" colspan="1">C4—C5—H52</td>
<td rowspan="1" colspan="1">110.2 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N1—H1</td>
<td rowspan="1" colspan="1">107.4 (13)</td>
<td rowspan="1" colspan="1">H51—C5—H52</td>
<td rowspan="1" colspan="1">108.1 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—N1—H1</td>
<td rowspan="1" colspan="1">109.3 (13)</td>
<td rowspan="1" colspan="1">N1—C6—C5</td>
<td rowspan="1" colspan="1">113.44 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—C3</td>
<td rowspan="1" colspan="1">114.07 (13)</td>
<td rowspan="1" colspan="1">N1—C6—H61</td>
<td rowspan="1" colspan="1">108.3 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—H21</td>
<td rowspan="1" colspan="1">106.5 (10)</td>
<td rowspan="1" colspan="1">C5—C6—H61</td>
<td rowspan="1" colspan="1">109.6 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—H21</td>
<td rowspan="1" colspan="1">108.4 (11)</td>
<td rowspan="1" colspan="1">N1—C6—H62</td>
<td rowspan="1" colspan="1">108.6 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—H22</td>
<td rowspan="1" colspan="1">107.6 (11)</td>
<td rowspan="1" colspan="1">C5—C6—H62</td>
<td rowspan="1" colspan="1">109.5 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—H22</td>
<td rowspan="1" colspan="1">110.0 (11)</td>
<td rowspan="1" colspan="1">H61—C6—H62</td>
<td rowspan="1" colspan="1">107.2 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">H21—C2—H22</td>
<td rowspan="1" colspan="1">110.3 (15)</td>
<td rowspan="1" colspan="1">C42—C41—C46</td>
<td rowspan="1" colspan="1">117.02 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4</td>
<td rowspan="1" colspan="1">111.72 (12)</td>
<td rowspan="1" colspan="1">C42—C41—C4</td>
<td rowspan="1" colspan="1">123.54 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H31</td>
<td rowspan="1" colspan="1">109.2 (13)</td>
<td rowspan="1" colspan="1">C46—C41—C4</td>
<td rowspan="1" colspan="1">119.44 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H31</td>
<td rowspan="1" colspan="1">108.6 (12)</td>
<td rowspan="1" colspan="1">C43—C42—C41</td>
<td rowspan="1" colspan="1">121.70 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H32</td>
<td rowspan="1" colspan="1">108.5 (10)</td>
<td rowspan="1" colspan="1">C43—C42—H42</td>
<td rowspan="1" colspan="1">117.1 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H32</td>
<td rowspan="1" colspan="1">107.8 (10)</td>
<td rowspan="1" colspan="1">C41—C42—H42</td>
<td rowspan="1" colspan="1">121.2 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">H31—C3—H32</td>
<td rowspan="1" colspan="1">111.1 (15)</td>
<td rowspan="1" colspan="1">C44—C43—C42</td>
<td rowspan="1" colspan="1">119.67 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C4—C41</td>
<td rowspan="1" colspan="1">109.23 (10)</td>
<td rowspan="1" colspan="1">C44—C43—H43</td>
<td rowspan="1" colspan="1">119.2 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C4—C3</td>
<td rowspan="1" colspan="1">105.91 (11)</td>
<td rowspan="1" colspan="1">C42—C43—H43</td>
<td rowspan="1" colspan="1">121.1 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C41—C4—C3</td>
<td rowspan="1" colspan="1">110.72 (11)</td>
<td rowspan="1" colspan="1">C43—C44—C45</td>
<td rowspan="1" colspan="1">120.47 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C4—C5</td>
<td rowspan="1" colspan="1">109.74 (11)</td>
<td rowspan="1" colspan="1">C43—C44—Cl44</td>
<td rowspan="1" colspan="1">119.66 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C41—C4—C5</td>
<td rowspan="1" colspan="1">112.78 (11)</td>
<td rowspan="1" colspan="1">C45—C44—Cl44</td>
<td rowspan="1" colspan="1">119.87 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5</td>
<td rowspan="1" colspan="1">108.23 (12)</td>
<td rowspan="1" colspan="1">C46—C45—C44</td>
<td rowspan="1" colspan="1">119.30 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—O4—H4A</td>
<td rowspan="1" colspan="1">109.3 (14)</td>
<td rowspan="1" colspan="1">C46—C45—H45</td>
<td rowspan="1" colspan="1">119.4 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4</td>
<td rowspan="1" colspan="1">111.55 (12)</td>
<td rowspan="1" colspan="1">C44—C45—H45</td>
<td rowspan="1" colspan="1">121.3 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—H51</td>
<td rowspan="1" colspan="1">110.7 (10)</td>
<td rowspan="1" colspan="1">C45—C46—C41</td>
<td rowspan="1" colspan="1">121.82 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—H51</td>
<td rowspan="1" colspan="1">109.1 (9)</td>
<td rowspan="1" colspan="1">C45—C46—H46</td>
<td rowspan="1" colspan="1">120.8 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—H52</td>
<td rowspan="1" colspan="1">107.1 (11)</td>
<td rowspan="1" colspan="1">C41—C46—H46</td>
<td rowspan="1" colspan="1">117.4 (12)</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—N1—C2—C3</td>
<td rowspan="1" colspan="1">53.23 (17)</td>
<td rowspan="1" colspan="1">O4—C4—C41—C46</td>
<td rowspan="1" colspan="1">−49.35 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—C3—C4</td>
<td rowspan="1" colspan="1">−54.44 (18)</td>
<td rowspan="1" colspan="1">C3—C4—C41—C46</td>
<td rowspan="1" colspan="1">66.91 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4—O4</td>
<td rowspan="1" colspan="1">−64.46 (15)</td>
<td rowspan="1" colspan="1">C5—C4—C41—C46</td>
<td rowspan="1" colspan="1">−171.65 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4—C41</td>
<td rowspan="1" colspan="1">177.25 (12)</td>
<td rowspan="1" colspan="1">C46—C41—C42—C43</td>
<td rowspan="1" colspan="1">0.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td>
<td rowspan="1" colspan="1">53.16 (15)</td>
<td rowspan="1" colspan="1">C4—C41—C42—C43</td>
<td rowspan="1" colspan="1">−179.21 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C4—C5—C6</td>
<td rowspan="1" colspan="1">60.81 (15)</td>
<td rowspan="1" colspan="1">C41—C42—C43—C44</td>
<td rowspan="1" colspan="1">−1.3 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C41—C4—C5—C6</td>
<td rowspan="1" colspan="1">−177.17 (11)</td>
<td rowspan="1" colspan="1">C42—C43—C44—C45</td>
<td rowspan="1" colspan="1">1.2 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td>
<td rowspan="1" colspan="1">−54.33 (15)</td>
<td rowspan="1" colspan="1">C42—C43—C44—Cl44</td>
<td rowspan="1" colspan="1">−178.91 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—N1—C6—C5</td>
<td rowspan="1" colspan="1">−54.19 (16)</td>
<td rowspan="1" colspan="1">C43—C44—C45—C46</td>
<td rowspan="1" colspan="1">0.0 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6—N1</td>
<td rowspan="1" colspan="1">56.56 (16)</td>
<td rowspan="1" colspan="1">Cl44—C44—C45—C46</td>
<td rowspan="1" colspan="1">−179.90 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C4—C41—C42</td>
<td rowspan="1" colspan="1">130.07 (15)</td>
<td rowspan="1" colspan="1">C44—C45—C46—C41</td>
<td rowspan="1" colspan="1">−1.1 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C41—C42</td>
<td rowspan="1" colspan="1">−113.68 (16)</td>
<td rowspan="1" colspan="1">C42—C41—C46—C45</td>
<td rowspan="1" colspan="1">1.0 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—C41—C42</td>
<td rowspan="1" colspan="1">7.76 (19)</td>
<td rowspan="1" colspan="1">C4—C41—C46—C45</td>
<td rowspan="1" colspan="1">−179.54 (14)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title>
<table-wrap position="anchor" id="d1e1878"><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···O4<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.89 (2)</td>
<td rowspan="1" colspan="1">2.41 (2)</td>
<td rowspan="1" colspan="1">3.2036 (16)</td>
<td rowspan="1" colspan="1">147.2 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—H4A···N1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.84 (2)</td>
<td rowspan="1" colspan="1">1.97 (2)</td>
<td rowspan="1" colspan="1">2.8089 (17)</td>
<td rowspan="1" colspan="1">174 (2)</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) <italic>x</italic>
, −<italic>y</italic>
+1/2, <italic>z</italic>
+1/2; (ii) −<italic>x</italic>
+2, <italic>y</italic>
−1/2, −<italic>z</italic>
+1/2.</p>
</sec>
</app>
</app-group>
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</ref-list>
</back>
<floats-group><table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (Å, °)</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 style="" rowspan="1" colspan="1" align="left" valign="top">N1—H1⋯O4<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.89 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.41 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.2036 (16)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">147.2 (17)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O4—H4<italic>A</italic>
⋯N1<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.84 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.97 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.8089 (17)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">174 (2)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-66-0o562-efi6.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-66-0o562-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>

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