4-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid
Identifieur interne : 000A04 ( Pmc/Corpus ); précédent : 000A03; suivant : 000A054-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid
Auteurs : Songwen Xie ; Dannette A. Nusbaum ; Holly J. Stein ; Maren PinkSource :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2010.
Abstract
The racemic title compound, C16H20O3, was synthesized to study the hydrogen-bonding interaction of the two enantiomers in the solid state. In the crystal structure,
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DOI: 10.1107/S1600536810018544
PubMed: 21579516
PubMed Central: 2979377
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">4-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid</title><author><name sortKey="Xie, Songwen" sort="Xie, Songwen" uniqKey="Xie S" first="Songwen" last="Xie">Songwen Xie</name><affiliation><nlm:aff id="a">Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Nusbaum, Dannette A" sort="Nusbaum, Dannette A" uniqKey="Nusbaum D" first="Dannette A." last="Nusbaum">Dannette A. Nusbaum</name><affiliation><nlm:aff id="a">Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Stein, Holly J" sort="Stein, Holly J" uniqKey="Stein H" first="Holly J." last="Stein">Holly J. Stein</name><affiliation><nlm:aff id="a">Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Pink, Maren" sort="Pink, Maren" uniqKey="Pink M" first="Maren" last="Pink">Maren Pink</name><affiliation><nlm:aff id="b">Indiana University Molecular Structure Center, Indiana University, Bloomington, IN 47405–7102,<country>USA</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21579516</idno><idno type="pmc">2979377</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979377</idno><idno type="RBID">PMC:2979377</idno><idno type="doi">10.1107/S1600536810018544</idno><date when="2010">2010</date><idno type="wicri:Area/Pmc/Corpus">000A04</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A04</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">4-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid</title><author><name sortKey="Xie, Songwen" sort="Xie, Songwen" uniqKey="Xie S" first="Songwen" last="Xie">Songwen Xie</name><affiliation><nlm:aff id="a">Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Nusbaum, Dannette A" sort="Nusbaum, Dannette A" uniqKey="Nusbaum D" first="Dannette A." last="Nusbaum">Dannette A. Nusbaum</name><affiliation><nlm:aff id="a">Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Stein, Holly J" sort="Stein, Holly J" uniqKey="Stein H" first="Holly J." last="Stein">Holly J. Stein</name><affiliation><nlm:aff id="a">Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Pink, Maren" sort="Pink, Maren" uniqKey="Pink M" first="Maren" last="Pink">Maren Pink</name><affiliation><nlm:aff id="b">Indiana University Molecular Structure Center, Indiana University, Bloomington, IN 47405–7102,<country>USA</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></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The racemic title compound, C<sub>16</sub>H<sub>20</sub>O<sub>3</sub>, was synthesized to study the hydrogen-bonding interaction of the two enantiomers in the solid state. In the crystal structure, <italic>R</italic> and <italic>S</italic> pairs of the racemate are linked by pairs of intermolecular O—H⋯O hydrogen bonds, producing centrosymmetric <italic>R</italic><sub>2</sub><sup>2</sup>(8) rings.</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></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 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">21579516</article-id><article-id pub-id-type="pmc">2979377</article-id><article-id pub-id-type="publisher-id">fj2304</article-id><article-id pub-id-type="doi">10.1107/S1600536810018544</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536810018544</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title>4-(3-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid</article-title><alt-title><italic>C<sub>16</sub>H<sub>20</sub>O<sub>3</sub></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Xie</surname><given-names>Songwen</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Nusbaum</surname><given-names>Dannette A.</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Stein</surname><given-names>Holly J.</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Pink</surname><given-names>Maren</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><aff id="a"><label>a</label>Department of Natural, Information, and Mathematical Sciences, Indiana University Kokomo, Kokomo, IN 46904–9003,<country>USA</country></aff><aff id="b"><label>b</label>Indiana University Molecular Structure Center, Indiana University, Bloomington, IN 47405–7102,<country>USA</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>soxie@iuk.edu</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>6</month><year>2010</year></pub-date><pub-date pub-type="epub"><day>26</day><month>5</month><year>2010</year></pub-date><pub-date pub-type="pmc-release"><day>26</day><month>5</month><year>2010</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>66</volume><issue>Pt 6</issue><issue-id pub-id-type="publisher-id">e100600</issue-id><fpage>o1443</fpage><lpage>o1443</lpage><history><date date-type="received"><day>15</day><month>5</month><year>2010</year></date><date date-type="accepted"><day>18</day><month>5</month><year>2010</year></date></history><permissions><copyright-statement>© Xie 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/S1600536810018544">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>The racemic title compound, C<sub>16</sub>H<sub>20</sub>O<sub>3</sub>, was synthesized to study the hydrogen-bonding interaction of the two enantiomers in the solid state. In the crystal structure, <italic>R</italic> and <italic>S</italic> pairs of the racemate are linked by pairs of intermolecular O—H⋯O hydrogen bonds, producing centrosymmetric <italic>R</italic><sub>2</sub><sup>2</sup>(8) rings.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature</title><p>For similar compounds in which the racemates also consist of carboxylic acid <italic>RS</italic> dimers, see: Xie <italic>et al.</italic> (2002<xref ref-type="bibr" rid="bb6"> ▶</xref>, 2007<italic>a</italic><xref ref-type="bibr" rid="bb7"> ▶</xref>, 2008<italic>a</italic><xref ref-type="bibr" rid="bb10"> ▶</xref>,<italic>b</italic><xref ref-type="bibr" rid="bb11"> ▶</xref>). For the structure of the precursor of the title compound, which is achiral and forms hydrogen-bonded dimers, see: Xie <italic>et al.</italic> (2007<italic>b</italic><xref ref-type="bibr" rid="bb8"> ▶</xref>). The chirality of the title compound is solely generated by the presence of the double bond in the cyclohexene ring, see: Xie <italic>et al.</italic> (2004<xref ref-type="bibr" rid="bb9"> ▶</xref>). For hydrogen-bond motifs, see: Bernstein <italic>et al.</italic> (1995<xref ref-type="bibr" rid="bb1"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-66-o1443-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>16</sub>H<sub>20</sub>O<sub>3</sub></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 260.32</p></list-item><list-item><p>Orthorhombic, <inline-formula><inline-graphic xlink:href="e-66-o1443-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 11.032 (2) Å</p></list-item><list-item><p><italic>b</italic> = 7.8423 (17) Å</p></list-item><list-item><p><italic>c</italic> = 32.140 (8) Å</p></list-item><list-item><p><italic>V</italic> = 2780.7 (11) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 8</p></list-item><list-item><p>Synchrotron radiation</p></list-item><list-item><p>λ = 0.44280 Å</p></list-item><list-item><p>μ = 0.05 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 100 K</p></list-item><list-item><p>0.02 × 0.01 × 0.01 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection</title><p><list list-type="simple"><list-item><p>Bruker Platform goniometer diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2007<xref ref-type="bibr" rid="bb3"> ▶</xref>; Blessing, 1995<xref ref-type="bibr" rid="bb2"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.999, <italic>T</italic><sub>max</sub> = 1.000</p></list-item><list-item><p>8586 measured reflections</p></list-item><list-item><p>2173 independent reflections</p></list-item><list-item><p>1755 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.050</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>)] = 0.037</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.119</p></list-item><list-item><p><italic>S</italic> = 1.11</p></list-item><list-item><p>2173 reflections</p></list-item><list-item><p>179 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> = 0.17 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.23 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e437"><title></title><p>Data collection: <italic>APEX2</italic> (Bruker, 2007<xref ref-type="bibr" rid="bb3"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2007<xref ref-type="bibr" rid="bb3"> ▶</xref>); data reduction: <italic>SAINT</italic>; program(s) used to solve structure: <italic>SIR2004</italic> (Burla <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb4"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb5"> ▶</xref>); molecular graphics: <italic>SHELXTL</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb5"> ▶</xref>); software used to prepare material for publication: <italic>SHELXTL</italic>.</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data" xlink:href="e-66-o1443-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablocks global, I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536810018544/fj2304sup1.cif">10.1107/S1600536810018544/fj2304sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-66-o1443-sup1.cif" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material content-type="local-data" xlink:href="e-66-o1443-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/S1600536810018544/fj2304Isup2.hkl">10.1107/S1600536810018544/fj2304Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-66-o1443-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?fj2304&file=fj2304sup0.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?fj2304sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?fj2304&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?fj2304">FJ2304</ext-link>).</p></fn></fn-group><ack><p>SX, DN, and HS are grateful for the Grant-in-aid for Faculty Research from Indiana University Kokomo, as well as the Senior Research Grant from Indiana Academy of Science. ChemMatCARS Sector 15 is principally supported by the National Science Foundation/Department of Energy under grant No. CHE-0535644. Use of the advanced Photon Source was supported by the US Department of Energy, Office of Science, Office of Basic Energy Sciences, under contract No. DE—AC02-06CH11357. The authors also want to thank the beamline for synchrotron radiation at the Advanced Photon Source, Argonne National Laboratory.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>The title carboxylic acid was prepared to study the interaction of the two
enantiomers in the solid state. We have previously reported the structure of
its precursor, which is achiral and forms hydrogen-bonded dimers (Xie <italic>et
al.</italic>, 2007b). The chirality of the title compound is solely
generated by
the presence of the double bond in the cyclohexene ring (Xie <italic>et al.</italic>,
2004). The resultant racemate is made up of carboxylic acid RS dimers
(Xie
<italic>et al.</italic>, 2002, 2007a, 2008a,b). The
structure and atom numbering are
shown in Fig. 1, which illustrates the half-chair conformation of the
cyclohexene ring. The torsion angles involving atoms C4, C5, C6, C1, and C2
are near 180°. The carboxyl group is almost perpendicular to the cyclohexene
ring with an angle of 85.3° between the O1—C14—O2—C3 plane and the
C1—C6 ring. The double bond between C5—C6 is not fully conjugated with the
aromatic ring as shown by the C1—C6—C5 plane to benzene ring angle of
38.7°. Unlike other previously reported <italic>para</italic> substituted analogs and
like other previously reported <italic>meta</italic> substituted analogs (Xie <italic>et
al.</italic>, 2008b), the molecule also has a chiral axis due to the
<italic>meta</italic>methoxy substituent on the aromatic ring.</p><p>Fig. 2 shows the hydrogen bonding scheme. Atom O2 acts as a donor in an
intermolecular hydrogen bond to atom O1, producing an R22(8) ring (Bernstein
<italic>et al.</italic>, 1995), thus creating a hydrogen- bonded dimer. There is
no
evidence to suggest that weak directional interactions interconnect the
dimers. Hydrogen bond geometry is given in Table 1.</p></sec><sec id="experimental"><title>Experimental </title><p>The title carboxylic acid was synthesized following the similar method reported
by Xie <italic>et al.</italic>, 2002. Purified compound was recrystallized from
hexane-
dichloromethane as colorless plates (m.p. 415-417 K).</p></sec><sec id="refinement"><title>Refinement </title><p>The data collection was carried out using synchrotron radiation (λ= 0.44280,
diamond 111 monochromator, two mirrors to exclude higher harmonics) with a
frame time of 2 second and a detector distance of 6.0 cm. A randomly oriented
region of reciprocal space was surveyed to the extent of a hemisphere. Two
major sections of frames were collected with 0.50° steps in φ and a detector
position of -20° in 2θ. Data to a resolution of 0.84 Å were considered in
the reduction. Final cell constants were calculated from the xyz centroids of
2804 strong reflections from the actual data collection after integration
(SAINT, Bruker Analytical X-Ray Systems, Madison, WI, 2008). The intensity
data were corrected for absorption (SADABS) (Blessing, 1995).</p><p>The space group Pbca was determined based on intensity statistics and
systematic absences. The structure was solved using SIR-2004 (Burla <italic>et
al.</italic>, 2005) and refined with SHELXL-97 (Sheldrick, 2008). A
direct-methods
solution was calculated, which provided most non-hydrogen atoms from the
E-map. Full-matrix least squares / difference Fourier cycles were performed,
which located the remaining non-hydrogen atoms. All non-hydrogen atoms were
refined with anisotropic displacement parameters. The hydrogen atoms were
placed in ideal positions and refined as riding atoms with relative isotropic
displacement parameters with the exception of the hydroxyl hydrogen atom,
which was refined for all parameters. The final full matrix least squares
refinement converged to R1 = 0.0368 and wR2 = 0.1190 (F<sup>2</sup>, all data). The
structure was found as proposed. The remaining electron density is minuscule
and located on bonds.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure and atom numbering scheme.</p></caption><graphic xlink:href="e-66-o1443-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>Hydrogen bonded dimer. Dashed lines represent hydrogen bonds. [Symmetry code: #1 -x,-y,-z+1.]</p></caption><graphic xlink:href="e-66-o1443-fig2"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e142"><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>16</sub>H<sub>20</sub>O<sub>3</sub></td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 1120</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 260.32</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.244 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Orthorhombic, <italic>P</italic><italic>b</italic><italic>c</italic><italic>a</italic></td><td rowspan="1" colspan="1">Synchrotron radiation, λ = 0.44280 Å</td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 2ac 2ab</td><td rowspan="1" colspan="1">Cell parameters from 2804 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 11.032 (2) Å</td><td rowspan="1" colspan="1">θ = 2.3–15.3°</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 7.8423 (17) Å</td><td rowspan="1" colspan="1">µ = 0.05 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 32.140 (8) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 100 K</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 2780.7 (11) Å<sup>3</sup></td><td rowspan="1" colspan="1">Plate, colorless</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 8</td><td rowspan="1" colspan="1">0.02 × 0.01 × 0.01 mm</td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e258"><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">Bruker Platform goniometer diffractometer</td><td rowspan="1" colspan="1">2173 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: synchrotron</td><td rowspan="1" colspan="1">1755 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">diamond 1 1 1</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.050</td></tr><tr><td rowspan="1" colspan="1">Detector resolution: 83.33 pixels mm<sup>-1</sup></td><td rowspan="1" colspan="1">θ<sub>max</sub> = 15.3°, θ<sub>min</sub> = 0.8°</td></tr><tr><td rowspan="1" colspan="1">ω and phi scans</td><td rowspan="1" colspan="1"><italic>h</italic> = −11→13</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2007; Blessing, 1995)</td><td rowspan="1" colspan="1"><italic>k</italic> = −8→6</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.999, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>l</italic> = −38→26</td></tr><tr><td rowspan="1" colspan="1">8586 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="d1e378"><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>)] = 0.037</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>) = 0.119</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> = 1.11</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0707<italic>P</italic>)<sup>2</sup> + 0.0727<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">2173 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.001</td></tr><tr><td rowspan="1" colspan="1">179 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.17 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> = −0.23 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="d1e535"><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><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> >
σ(<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="d1e627"><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">O1</td><td rowspan="1" colspan="1">−0.01213 (10)</td><td rowspan="1" colspan="1">0.06346 (16)</td><td rowspan="1" colspan="1">0.54893 (3)</td><td rowspan="1" colspan="1">0.0182 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.02685 (11)</td><td rowspan="1" colspan="1">0.22640 (18)</td><td rowspan="1" colspan="1">0.49329 (4)</td><td rowspan="1" colspan="1">0.0209 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2O</td><td rowspan="1" colspan="1">0.018 (2)</td><td rowspan="1" colspan="1">0.122 (4)</td><td rowspan="1" colspan="1">0.4790 (8)</td><td rowspan="1" colspan="1">0.049 (7)*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.19151 (12)</td><td rowspan="1" colspan="1">0.77788 (18)</td><td rowspan="1" colspan="1">0.76439 (3)</td><td rowspan="1" colspan="1">0.0250 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">−0.07178 (15)</td><td rowspan="1" colspan="1">0.5720 (2)</td><td rowspan="1" colspan="1">0.60649 (5)</td><td rowspan="1" colspan="1">0.0173 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1A</td><td rowspan="1" colspan="1">−0.0730</td><td rowspan="1" colspan="1">0.6650</td><td rowspan="1" colspan="1">0.5857</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1B</td><td rowspan="1" colspan="1">−0.1403</td><td rowspan="1" colspan="1">0.5909</td><td rowspan="1" colspan="1">0.6258</td><td rowspan="1" colspan="1">0.021*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">−0.09016 (14)</td><td rowspan="1" colspan="1">0.4018 (2)</td><td rowspan="1" colspan="1">0.58418 (5)</td><td rowspan="1" colspan="1">0.0152 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">−0.1031</td><td rowspan="1" colspan="1">0.3108</td><td rowspan="1" colspan="1">0.6055</td><td rowspan="1" colspan="1">0.018*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.02669 (14)</td><td rowspan="1" colspan="1">0.3611 (2)</td><td rowspan="1" colspan="1">0.55976 (5)</td><td rowspan="1" colspan="1">0.0141 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.0446</td><td rowspan="1" colspan="1">0.4592</td><td rowspan="1" colspan="1">0.5409</td><td rowspan="1" colspan="1">0.017*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.13603 (14)</td><td rowspan="1" colspan="1">0.3370 (2)</td><td rowspan="1" colspan="1">0.58944 (5)</td><td rowspan="1" colspan="1">0.0148 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.1288</td><td rowspan="1" colspan="1">0.2227</td><td rowspan="1" colspan="1">0.6030</td><td rowspan="1" colspan="1">0.018*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.13641 (15)</td><td rowspan="1" colspan="1">0.4715 (2)</td><td rowspan="1" colspan="1">0.62290 (5)</td><td rowspan="1" colspan="1">0.0161 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.2066</td><td rowspan="1" colspan="1">0.4796</td><td rowspan="1" colspan="1">0.6399</td><td rowspan="1" colspan="1">0.019*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.04532 (15)</td><td rowspan="1" colspan="1">0.5812 (2)</td><td rowspan="1" colspan="1">0.63059 (5)</td><td rowspan="1" colspan="1">0.0152 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.05757 (14)</td><td rowspan="1" colspan="1">0.7208 (2)</td><td rowspan="1" colspan="1">0.66193 (5)</td><td rowspan="1" colspan="1">0.0157 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.11780 (15)</td><td rowspan="1" colspan="1">0.6918 (2)</td><td rowspan="1" colspan="1">0.69955 (5)</td><td rowspan="1" colspan="1">0.0167 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">0.1500</td><td rowspan="1" colspan="1">0.5820</td><td rowspan="1" colspan="1">0.7054</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.13098 (15)</td><td rowspan="1" colspan="1">0.8233 (2)</td><td rowspan="1" colspan="1">0.72858 (5)</td><td rowspan="1" colspan="1">0.0181 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.08441 (15)</td><td rowspan="1" colspan="1">0.9845 (2)</td><td rowspan="1" colspan="1">0.72076 (5)</td><td rowspan="1" colspan="1">0.0202 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">0.0930</td><td rowspan="1" colspan="1">1.0736</td><td rowspan="1" colspan="1">0.7406</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.02467 (16)</td><td rowspan="1" colspan="1">1.0126 (3)</td><td rowspan="1" colspan="1">0.68315 (5)</td><td rowspan="1" colspan="1">0.0209 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">−0.0067</td><td rowspan="1" colspan="1">1.1228</td><td rowspan="1" colspan="1">0.6772</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.01008 (15)</td><td rowspan="1" colspan="1">0.8828 (2)</td><td rowspan="1" colspan="1">0.65423 (5)</td><td rowspan="1" colspan="1">0.0189 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">−0.0324</td><td rowspan="1" colspan="1">0.9042</td><td rowspan="1" colspan="1">0.6291</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">−0.20110 (15)</td><td rowspan="1" colspan="1">0.4090 (2)</td><td rowspan="1" colspan="1">0.55581 (5)</td><td rowspan="1" colspan="1">0.0194 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13A</td><td rowspan="1" colspan="1">−0.2153</td><td rowspan="1" colspan="1">0.2962</td><td rowspan="1" colspan="1">0.5436</td><td rowspan="1" colspan="1">0.029*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13B</td><td rowspan="1" colspan="1">−0.1870</td><td rowspan="1" colspan="1">0.4920</td><td rowspan="1" colspan="1">0.5335</td><td rowspan="1" colspan="1">0.029*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13C</td><td rowspan="1" colspan="1">−0.2722</td><td rowspan="1" colspan="1">0.4433</td><td rowspan="1" colspan="1">0.5721</td><td rowspan="1" colspan="1">0.029*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.01185 (14)</td><td rowspan="1" colspan="1">0.2031 (2)</td><td rowspan="1" colspan="1">0.53354 (5)</td><td rowspan="1" colspan="1">0.0137 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.25486 (15)</td><td rowspan="1" colspan="1">0.3418 (2)</td><td rowspan="1" colspan="1">0.56468 (5)</td><td rowspan="1" colspan="1">0.0183 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15A</td><td rowspan="1" colspan="1">0.3235</td><td rowspan="1" colspan="1">0.3277</td><td rowspan="1" colspan="1">0.5837</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15B</td><td rowspan="1" colspan="1">0.2618</td><td rowspan="1" colspan="1">0.4515</td><td rowspan="1" colspan="1">0.5503</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15C</td><td rowspan="1" colspan="1">0.2552</td><td rowspan="1" colspan="1">0.2492</td><td rowspan="1" colspan="1">0.5442</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.19283 (18)</td><td rowspan="1" colspan="1">0.8987 (3)</td><td rowspan="1" colspan="1">0.79772 (5)</td><td rowspan="1" colspan="1">0.0244 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16A</td><td rowspan="1" colspan="1">0.2328</td><td rowspan="1" colspan="1">0.8483</td><td rowspan="1" colspan="1">0.8220</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16B</td><td rowspan="1" colspan="1">0.1094</td><td rowspan="1" colspan="1">0.9297</td><td rowspan="1" colspan="1">0.8050</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16C</td><td rowspan="1" colspan="1">0.2371</td><td rowspan="1" colspan="1">1.0010</td><td rowspan="1" colspan="1">0.7890</td><td rowspan="1" colspan="1">0.037*</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="d1e1158"><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">O1</td><td rowspan="1" colspan="1">0.0202 (7)</td><td rowspan="1" colspan="1">0.0155 (9)</td><td rowspan="1" colspan="1">0.0188 (7)</td><td rowspan="1" colspan="1">−0.0023 (5)</td><td rowspan="1" colspan="1">0.0004 (5)</td><td rowspan="1" colspan="1">−0.0007 (5)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0300 (7)</td><td rowspan="1" colspan="1">0.0176 (10)</td><td rowspan="1" colspan="1">0.0153 (7)</td><td rowspan="1" colspan="1">−0.0046 (5)</td><td rowspan="1" colspan="1">0.0012 (5)</td><td rowspan="1" colspan="1">−0.0023 (5)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0342 (8)</td><td rowspan="1" colspan="1">0.0229 (10)</td><td rowspan="1" colspan="1">0.0177 (7)</td><td rowspan="1" colspan="1">0.0040 (5)</td><td rowspan="1" colspan="1">−0.0082 (5)</td><td rowspan="1" colspan="1">−0.0049 (5)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0154 (9)</td><td rowspan="1" colspan="1">0.0176 (13)</td><td rowspan="1" colspan="1">0.0190 (9)</td><td rowspan="1" colspan="1">0.0023 (7)</td><td rowspan="1" colspan="1">0.0011 (7)</td><td rowspan="1" colspan="1">−0.0024 (7)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0133 (9)</td><td rowspan="1" colspan="1">0.0163 (12)</td><td rowspan="1" colspan="1">0.0161 (8)</td><td rowspan="1" colspan="1">0.0002 (6)</td><td rowspan="1" colspan="1">0.0005 (6)</td><td rowspan="1" colspan="1">0.0001 (6)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0147 (9)</td><td rowspan="1" colspan="1">0.0130 (12)</td><td rowspan="1" colspan="1">0.0148 (8)</td><td rowspan="1" colspan="1">−0.0001 (6)</td><td rowspan="1" colspan="1">−0.0009 (6)</td><td rowspan="1" colspan="1">0.0004 (7)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0126 (9)</td><td rowspan="1" colspan="1">0.0149 (12)</td><td rowspan="1" colspan="1">0.0169 (8)</td><td rowspan="1" colspan="1">0.0003 (6)</td><td rowspan="1" colspan="1">−0.0016 (6)</td><td rowspan="1" colspan="1">0.0007 (7)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0159 (9)</td><td rowspan="1" colspan="1">0.0165 (12)</td><td rowspan="1" colspan="1">0.0159 (8)</td><td rowspan="1" colspan="1">−0.0020 (7)</td><td rowspan="1" colspan="1">−0.0018 (6)</td><td rowspan="1" colspan="1">−0.0007 (7)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0162 (9)</td><td rowspan="1" colspan="1">0.0151 (12)</td><td rowspan="1" colspan="1">0.0142 (8)</td><td rowspan="1" colspan="1">−0.0016 (7)</td><td rowspan="1" colspan="1">0.0014 (7)</td><td rowspan="1" colspan="1">0.0018 (6)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0119 (9)</td><td rowspan="1" colspan="1">0.0179 (13)</td><td rowspan="1" colspan="1">0.0171 (9)</td><td rowspan="1" colspan="1">−0.0020 (7)</td><td rowspan="1" colspan="1">0.0038 (6)</td><td rowspan="1" colspan="1">−0.0007 (7)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0182 (9)</td><td rowspan="1" colspan="1">0.0138 (12)</td><td rowspan="1" colspan="1">0.0181 (9)</td><td rowspan="1" colspan="1">0.0009 (6)</td><td rowspan="1" colspan="1">0.0022 (6)</td><td rowspan="1" colspan="1">−0.0004 (6)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0175 (9)</td><td rowspan="1" colspan="1">0.0198 (13)</td><td rowspan="1" colspan="1">0.0170 (8)</td><td rowspan="1" colspan="1">−0.0018 (7)</td><td rowspan="1" colspan="1">0.0005 (7)</td><td rowspan="1" colspan="1">0.0002 (7)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0197 (10)</td><td rowspan="1" colspan="1">0.0204 (13)</td><td rowspan="1" colspan="1">0.0205 (9)</td><td rowspan="1" colspan="1">−0.0017 (7)</td><td rowspan="1" colspan="1">0.0028 (7)</td><td rowspan="1" colspan="1">−0.0063 (7)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0228 (10)</td><td rowspan="1" colspan="1">0.0161 (13)</td><td rowspan="1" colspan="1">0.0239 (10)</td><td rowspan="1" colspan="1">0.0045 (7)</td><td rowspan="1" colspan="1">0.0012 (7)</td><td rowspan="1" colspan="1">−0.0020 (7)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0172 (9)</td><td rowspan="1" colspan="1">0.0206 (14)</td><td rowspan="1" colspan="1">0.0189 (9)</td><td rowspan="1" colspan="1">0.0025 (7)</td><td rowspan="1" colspan="1">−0.0013 (7)</td><td rowspan="1" colspan="1">−0.0012 (7)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0145 (9)</td><td rowspan="1" colspan="1">0.0199 (13)</td><td rowspan="1" colspan="1">0.0238 (9)</td><td rowspan="1" colspan="1">0.0016 (7)</td><td rowspan="1" colspan="1">−0.0021 (7)</td><td rowspan="1" colspan="1">−0.0031 (7)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0074 (8)</td><td rowspan="1" colspan="1">0.0156 (13)</td><td rowspan="1" colspan="1">0.0181 (9)</td><td rowspan="1" colspan="1">0.0008 (6)</td><td rowspan="1" colspan="1">−0.0011 (6)</td><td rowspan="1" colspan="1">0.0011 (7)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0151 (9)</td><td rowspan="1" colspan="1">0.0173 (12)</td><td rowspan="1" colspan="1">0.0225 (8)</td><td rowspan="1" colspan="1">0.0000 (7)</td><td rowspan="1" colspan="1">−0.0005 (7)</td><td rowspan="1" colspan="1">−0.0029 (7)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0330 (11)</td><td rowspan="1" colspan="1">0.0235 (14)</td><td rowspan="1" colspan="1">0.0168 (9)</td><td rowspan="1" colspan="1">−0.0040 (8)</td><td rowspan="1" colspan="1">−0.0029 (8)</td><td rowspan="1" colspan="1">−0.0055 (7)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title><table-wrap position="anchor" id="d1e1551"><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">O1—C14</td><td rowspan="1" colspan="1">1.230 (2)</td><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.493 (2)</td></tr><tr><td rowspan="1" colspan="1">O2—C14</td><td rowspan="1" colspan="1">1.317 (2)</td><td rowspan="1" colspan="1">C7—C12</td><td rowspan="1" colspan="1">1.396 (3)</td></tr><tr><td rowspan="1" colspan="1">O2—H2O</td><td rowspan="1" colspan="1">0.94 (3)</td><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.398 (2)</td></tr><tr><td rowspan="1" colspan="1">O3—C9</td><td rowspan="1" colspan="1">1.378 (2)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.399 (2)</td></tr><tr><td rowspan="1" colspan="1">O3—C16</td><td rowspan="1" colspan="1">1.430 (2)</td><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.508 (2)</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.387 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.528 (2)</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.394 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—H1A</td><td rowspan="1" colspan="1">0.9900</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C1—H1B</td><td rowspan="1" colspan="1">0.9900</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C13</td><td rowspan="1" colspan="1">1.527 (2)</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.543 (2)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">1.0000</td><td rowspan="1" colspan="1">C13—H13A</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C3—C14</td><td rowspan="1" colspan="1">1.508 (2)</td><td rowspan="1" colspan="1">C13—H13B</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.549 (2)</td><td rowspan="1" colspan="1">C13—H13C</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">1.0000</td><td rowspan="1" colspan="1">C15—H15A</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.507 (2)</td><td rowspan="1" colspan="1">C15—H15B</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C4—C15</td><td rowspan="1" colspan="1">1.534 (2)</td><td rowspan="1" colspan="1">C15—H15C</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">1.0000</td><td rowspan="1" colspan="1">C16—H16A</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.346 (3)</td><td rowspan="1" colspan="1">C16—H16B</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C16—H16C</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14—O2—H2O</td><td rowspan="1" colspan="1">110.1 (16)</td><td rowspan="1" colspan="1">C7—C8—H8</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C9—O3—C16</td><td rowspan="1" colspan="1">117.34 (15)</td><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2</td><td rowspan="1" colspan="1">113.35 (14)</td><td rowspan="1" colspan="1">O3—C9—C10</td><td rowspan="1" colspan="1">124.50 (15)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—H1A</td><td rowspan="1" colspan="1">108.9</td><td rowspan="1" colspan="1">O3—C9—C8</td><td rowspan="1" colspan="1">114.65 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—H1A</td><td rowspan="1" colspan="1">108.9</td><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">120.85 (16)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—H1B</td><td rowspan="1" colspan="1">108.9</td><td rowspan="1" colspan="1">C9—C10—C11</td><td rowspan="1" colspan="1">118.43 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—H1B</td><td rowspan="1" colspan="1">108.9</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">120.8</td></tr><tr><td rowspan="1" colspan="1">H1A—C1—H1B</td><td rowspan="1" colspan="1">107.7</td><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">120.8</td></tr><tr><td rowspan="1" colspan="1">C13—C2—C1</td><td rowspan="1" colspan="1">110.76 (14)</td><td rowspan="1" colspan="1">C12—C11—C10</td><td rowspan="1" colspan="1">121.27 (18)</td></tr><tr><td rowspan="1" colspan="1">C13—C2—C3</td><td rowspan="1" colspan="1">111.93 (13)</td><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">119.4</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3</td><td rowspan="1" colspan="1">107.97 (13)</td><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">119.4</td></tr><tr><td rowspan="1" colspan="1">C13—C2—H2</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C11—C12—C7</td><td rowspan="1" colspan="1">120.36 (16)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C7—C12—H12</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C14—C3—C2</td><td rowspan="1" colspan="1">111.34 (13)</td><td rowspan="1" colspan="1">C2—C13—H13A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C14—C3—C4</td><td rowspan="1" colspan="1">109.16 (14)</td><td rowspan="1" colspan="1">C2—C13—H13B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">111.26 (13)</td><td rowspan="1" colspan="1">H13A—C13—H13B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C14—C3—H3</td><td rowspan="1" colspan="1">108.3</td><td rowspan="1" colspan="1">C2—C13—H13C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">108.3</td><td rowspan="1" colspan="1">H13A—C13—H13C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">108.3</td><td rowspan="1" colspan="1">H13B—C13—H13C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C15</td><td rowspan="1" colspan="1">110.53 (14)</td><td rowspan="1" colspan="1">O1—C14—O2</td><td rowspan="1" colspan="1">123.06 (15)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">110.86 (14)</td><td rowspan="1" colspan="1">O1—C14—C3</td><td rowspan="1" colspan="1">122.03 (14)</td></tr><tr><td rowspan="1" colspan="1">C15—C4—C3</td><td rowspan="1" colspan="1">110.06 (13)</td><td rowspan="1" colspan="1">O2—C14—C3</td><td rowspan="1" colspan="1">114.91 (15)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">108.4</td><td rowspan="1" colspan="1">C4—C15—H15A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C15—C4—H4</td><td rowspan="1" colspan="1">108.4</td><td rowspan="1" colspan="1">C4—C15—H15B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">108.4</td><td rowspan="1" colspan="1">H15A—C15—H15B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">125.23 (15)</td><td rowspan="1" colspan="1">C4—C15—H15C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">117.4</td><td rowspan="1" colspan="1">H15A—C15—H15C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">117.4</td><td rowspan="1" colspan="1">H15B—C15—H15C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C7</td><td rowspan="1" colspan="1">121.65 (15)</td><td rowspan="1" colspan="1">O3—C16—H16A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C1</td><td rowspan="1" colspan="1">120.98 (16)</td><td rowspan="1" colspan="1">O3—C16—H16B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C7—C6—C1</td><td rowspan="1" colspan="1">117.32 (14)</td><td rowspan="1" colspan="1">H16A—C16—H16B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C7—C8</td><td rowspan="1" colspan="1">118.65 (15)</td><td rowspan="1" colspan="1">O3—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C7—C6</td><td rowspan="1" colspan="1">120.89 (15)</td><td rowspan="1" colspan="1">H16A—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C8—C7—C6</td><td rowspan="1" colspan="1">120.46 (16)</td><td rowspan="1" colspan="1">H16B—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C7—C8—C9</td><td rowspan="1" colspan="1">120.42 (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—C1—C2—C13</td><td rowspan="1" colspan="1">−172.40 (14)</td><td rowspan="1" colspan="1">C5—C6—C7—C8</td><td rowspan="1" colspan="1">−39.5 (2)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td><td rowspan="1" colspan="1">−49.53 (18)</td><td rowspan="1" colspan="1">C1—C6—C7—C8</td><td rowspan="1" colspan="1">142.90 (16)</td></tr><tr><td rowspan="1" colspan="1">C13—C2—C3—C14</td><td rowspan="1" colspan="1">−52.46 (19)</td><td rowspan="1" colspan="1">C12—C7—C8—C9</td><td rowspan="1" colspan="1">−0.6 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C14</td><td rowspan="1" colspan="1">−174.62 (13)</td><td rowspan="1" colspan="1">C6—C7—C8—C9</td><td rowspan="1" colspan="1">178.94 (15)</td></tr><tr><td rowspan="1" colspan="1">C13—C2—C3—C4</td><td rowspan="1" colspan="1">−174.47 (15)</td><td rowspan="1" colspan="1">C16—O3—C9—C10</td><td rowspan="1" colspan="1">8.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">63.37 (17)</td><td rowspan="1" colspan="1">C16—O3—C9—C8</td><td rowspan="1" colspan="1">−171.22 (15)</td></tr><tr><td rowspan="1" colspan="1">C14—C3—C4—C5</td><td rowspan="1" colspan="1">−166.45 (14)</td><td rowspan="1" colspan="1">C7—C8—C9—O3</td><td rowspan="1" colspan="1">179.71 (14)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">−43.19 (19)</td><td rowspan="1" colspan="1">C7—C8—C9—C10</td><td rowspan="1" colspan="1">0.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C14—C3—C4—C15</td><td rowspan="1" colspan="1">70.95 (17)</td><td rowspan="1" colspan="1">O3—C9—C10—C11</td><td rowspan="1" colspan="1">−179.78 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C15</td><td rowspan="1" colspan="1">−165.78 (14)</td><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">−0.4 (2)</td></tr><tr><td rowspan="1" colspan="1">C15—C4—C5—C6</td><td rowspan="1" colspan="1">132.37 (18)</td><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">0.9 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">10.1 (2)</td><td rowspan="1" colspan="1">C10—C11—C12—C7</td><td rowspan="1" colspan="1">−1.3 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C7</td><td rowspan="1" colspan="1">−174.49 (16)</td><td rowspan="1" colspan="1">C8—C7—C12—C11</td><td rowspan="1" colspan="1">1.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">3.0 (3)</td><td rowspan="1" colspan="1">C6—C7—C12—C11</td><td rowspan="1" colspan="1">−178.39 (15)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">17.8 (2)</td><td rowspan="1" colspan="1">C2—C3—C14—O1</td><td rowspan="1" colspan="1">−60.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C7</td><td rowspan="1" colspan="1">−164.57 (14)</td><td rowspan="1" colspan="1">C4—C3—C14—O1</td><td rowspan="1" colspan="1">63.06 (19)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C7—C12</td><td rowspan="1" colspan="1">140.02 (18)</td><td rowspan="1" colspan="1">C2—C3—C14—O2</td><td rowspan="1" colspan="1">120.03 (15)</td></tr><tr><td rowspan="1" colspan="1">C1—C6—C7—C12</td><td rowspan="1" colspan="1">−37.5 (2)</td><td rowspan="1" colspan="1">C4—C3—C14—O2</td><td rowspan="1" colspan="1">−116.76 (15)</td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title><table-wrap position="anchor" id="d1e2287"><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">O2—H2O···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.94 (3)</td><td rowspan="1" colspan="1">1.71 (3)</td><td rowspan="1" colspan="1">2.6523 (19)</td><td rowspan="1" colspan="1">175 (2)</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>, −<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">Bernstein, J., Davis, R., Shimoni, L. & Chang, N.-L. (1995). <italic>Angew. Chem. Int. Ed. Engl.</italic><bold>34</bold>, 1555–1573.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Blessing, R. H. (1995). <italic>Acta Cryst.</italic> A<bold>51</bold>, 33–38.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Bruker (2007). <italic>APEX2</italic>, <italic>SAINT</italic> and <italic>SADABS</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). <italic>J. Appl. Cryst.</italic><bold>38</bold>, 381–388.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Xie, S., Hou, Y., Meyers, C. Y. & Robinson, P. D. (2002). <italic>Acta Cryst.</italic> E<bold>58</bold>, o1460–o1462.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Xie, S., Kenny, C. & Robinson, P. D. (2007<italic>a</italic>). <italic>Acta Cryst.</italic> E<bold>63</bold>, o3897.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Xie, S., Kenny, C. & Robinson, P. D. (2007<italic>b</italic>). <italic>Acta Cryst.</italic> E<bold>63</bold>, o1660–o1662.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Xie, S., Meyers, C. Y. & Robinson, P. D. (2004). <italic>Acta Cryst.</italic> E<bold>60</bold>, o1362–o1364.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Xie, S., O’Hearn, C. R. & Robinson, P. D. (2008<italic>a</italic>). <italic>Acta Cryst.</italic> E<bold>64</bold>, o554.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Xie, S., Stein, H. J. & Pink, M. (2008<italic>b</italic>). <italic>Acta Cryst.</italic> E<bold>64</bold>, o1869.</mixed-citation></ref></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">O2—H2<italic>O</italic>⋯O1<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.94 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.71 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.6523 (19)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">175 (2)</td></tr></tbody></table><table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-66-o1443-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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