MersV1, Pmc, Corpus, bibRecord, 000A07

Bostrycin

Identifieur interne : 000A07 ( Pmc/Corpus ); précédent : 000A06; suivant : 000A08

Bostrycin

Auteurs : Shao-Yuan Chen ; Chao Huang ; Chu-Long Zhang ; Yu-Zhe Chen ; Fu-Cheng Lin

Source :

Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2008.

RBID : PMC:2959567

Abstract

The title compound, C₁₆H₁₆O₈, is a potent nonspecific phytotoxin. The crystal structure is the average of two tautomers, 5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione. The cyclohexene rings in both tautomers display a half-chair conformation. An extensive O—H⋯O hydrogen-bonding network is present in the crystal structure.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959567

DOI: 10.1107/S1600536808032030
PubMed: 21581081
PubMed Central: 2959567

Links to Exploration step

PMC:2959567

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Bostrycin</title>
<author><name sortKey="Chen, Shao Yuan" sort="Chen, Shao Yuan" uniqKey="Chen S" first="Shao-Yuan" last="Chen">Shao-Yuan Chen</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Huang, Chao" sort="Huang, Chao" uniqKey="Huang C" first="Chao" last="Huang">Chao Huang</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zhang, Chu Long" sort="Zhang, Chu Long" uniqKey="Zhang C" first="Chu-Long" last="Zhang">Chu-Long Zhang</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Chen, Yu Zhe" sort="Chen, Yu Zhe" uniqKey="Chen Y" first="Yu-Zhe" last="Chen">Yu-Zhe Chen</name>
<affiliation><nlm:aff id="b">College of Pharmaceutical Sicence, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Lin, Fu Cheng" sort="Lin, Fu Cheng" uniqKey="Lin F" first="Fu-Cheng" last="Lin">Fu-Cheng Lin</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">21581081</idno>
<idno type="pmc">2959567</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959567</idno>
<idno type="RBID">PMC:2959567</idno>
<idno type="doi">10.1107/S1600536808032030</idno>
<date when="2008">2008</date>
<idno type="wicri:Area/Pmc/Corpus">000A07</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A07</idno>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Bostrycin</title>
<author><name sortKey="Chen, Shao Yuan" sort="Chen, Shao Yuan" uniqKey="Chen S" first="Shao-Yuan" last="Chen">Shao-Yuan Chen</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Huang, Chao" sort="Huang, Chao" uniqKey="Huang C" first="Chao" last="Huang">Chao Huang</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zhang, Chu Long" sort="Zhang, Chu Long" uniqKey="Zhang C" first="Chu-Long" last="Zhang">Chu-Long Zhang</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Chen, Yu Zhe" sort="Chen, Yu Zhe" uniqKey="Chen Y" first="Yu-Zhe" last="Chen">Yu-Zhe Chen</name>
<affiliation><nlm:aff id="b">College of Pharmaceutical Sicence, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Lin, Fu Cheng" sort="Lin, Fu Cheng" uniqKey="Lin F" first="Fu-Cheng" last="Lin">Fu-Cheng Lin</name>
<affiliation><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</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="2008">2008</date>
</imprint>
</series>
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<profileDesc><textClass></textClass>
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</teiHeader>
<front><div type="abstract" xml:lang="en"><p>The title compound, C<sub>16</sub>
H<sub>16</sub>
O<sub>8</sub>
, is a potent nonspecific phytotoxin. The crystal structure is the average of two tautomers, 5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione. The cyclohexene rings in both tautomers display a half-chair conformation. An extensive O—H⋯O hydrogen-bonding network is present in the crystal structure.</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>
</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">21581081</article-id>
<article-id pub-id-type="pmc">2959567</article-id>
<article-id pub-id-type="publisher-id">xu2453</article-id>
<article-id pub-id-type="doi">10.1107/S1600536808032030</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536808032030</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>Bostrycin</article-title>
<alt-title><italic>C<sub>16</sub>
H<sub>16</sub>
O<sub>8</sub>
</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Chen</surname>
<given-names>Shao-Yuan</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>Huang</surname>
<given-names>Chao</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhang</surname>
<given-names>Chu-Long</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Chen</surname>
<given-names>Yu-Zhe</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Lin</surname>
<given-names>Fu-Cheng</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<aff id="a"><label>a</label>
State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</aff>
<aff id="b"><label>b</label>
College of Pharmaceutical Sicence, Zhejiang University,<country>People’s Republic of China</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>fuchenglin@zju.edu.cn</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>11</month>
<year>2008</year>
</pub-date>
<pub-date pub-type="epub"><day>31</day>
<month>10</month>
<year>2008</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>31</day>
<month>10</month>
<year>2008</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the 
 							. </pmc-comment>
      <volume>64</volume>
<issue>Pt 11</issue>
<issue-id pub-id-type="publisher-id">e081100</issue-id>
<fpage>o2226</fpage>
<lpage>o2226</lpage>
<history><date date-type="received"><day>06</day>
<month>9</month>
<year>2008</year>
</date>
<date date-type="accepted"><day>06</day>
<month>10</month>
<year>2008</year>
</date>
</history>
<permissions><copyright-statement>© Chen et al. 2008</copyright-statement>
<copyright-year>2008</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/S1600536808032030">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>The title compound, C<sub>16</sub>
H<sub>16</sub>
O<sub>8</sub>
, is a potent nonspecific phytotoxin. The crystal structure is the average of two tautomers, 5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione. The cyclohexene rings in both tautomers display a half-chair conformation. An extensive O—H⋯O hydrogen-bonding network is present in the crystal structure.</p>
</abstract>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature</title>
<p>For general background, see: Charudattan & Rao (1982<xref ref-type="bibr" rid="bb1"> ▶</xref>
); van Eijk (1975<xref ref-type="bibr" rid="bb2"> ▶</xref>
). For a related structure, see: Kelly & Saha (1985<xref ref-type="bibr" rid="bb6"> ▶</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-64-o2226-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>16</sub>
O<sub>8</sub>
</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 336.29</p>
</list-item>
<list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-64-o2226-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
 = 8.280 (2) Å</p>
</list-item>
<list-item><p><italic>b</italic>
 = 6.644 (2) Å</p>
</list-item>
<list-item><p><italic>c</italic>
 = 13.1535 (12) Å</p>
</list-item>
<list-item><p>β = 102.12 (2)°</p>
</list-item>
<list-item><p><italic>V</italic>
 = 707.5 (3) Å<sup>3</sup>
</p>
</list-item>
<list-item><p><italic>Z</italic>
 = 2</p>
</list-item>
<list-item><p>Mo <italic>K</italic>
α radiation</p>
</list-item>
<list-item><p>μ = 0.13 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
 = 293 (2) K</p>
</list-item>
<list-item><p>0.30 × 0.20 × 0.08 mm</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.1.2"><title>Data collection</title>
<p><list list-type="simple"><list-item><p>Rigaku R-AXIS RAPID IP diffractometer</p>
</list-item>
<list-item><p>Absorption correction: multi-scan (<italic>ABSCOR</italic>
; Higashi, 1995<xref ref-type="bibr" rid="bb5"> ▶</xref>
) <italic>T</italic>
<sub>min</sub>
 = 0.953, <italic>T</italic>
<sub>max</sub>
 = 0.990</p>
</list-item>
<list-item><p>6151 measured reflections</p>
</list-item>
<list-item><p>1517 independent reflections</p>
</list-item>
<list-item><p>1282 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</p>
</list-item>
<list-item><p><italic>R</italic>
<sub>int</sub>
 = 0.025</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>
)] = 0.035</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.105</p>
</list-item>
<list-item><p><italic>S</italic>
 = 1.08</p>
</list-item>
<list-item><p>1517 reflections</p>
</list-item>
<list-item><p>220 parameters</p>
</list-item>
<list-item><p>1 restraint</p>
</list-item>
<list-item><p>H-atom parameters constrained</p>
</list-item>
<list-item><p>Δρ<sub>max</sub>
 = 0.24 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
 = −0.19 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
</sec>
<sec id="d5e506"><title></title>
<p>Data collection: <italic>PROCESS-AUTO</italic>
 (Rigaku, 1998<xref ref-type="bibr" rid="bb7"> ▶</xref>
); cell refinement: <italic>PROCESS-AUTO</italic>
; data reduction: <italic>CrystalStructure</italic>
 (Rigaku/MSC, 2002<xref ref-type="bibr" rid="bb8"> ▶</xref>
); program(s) used to solve structure: <italic>SHELXS97</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb9"> ▶</xref>
); program(s) used to refine structure: <italic>SHELXL97</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb9"> ▶</xref>
); molecular graphics: <italic>ORTEP-3</italic>
 (Farrugia, 1997<xref ref-type="bibr" rid="bb3"> ▶</xref>
); software used to prepare material for publication: <italic>WinGX</italic>
 (Farrugia, 1999<xref ref-type="bibr" rid="bb4"> ▶</xref>
).</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data" xlink:href="e-64-o2226-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/S1600536808032030/xu2453sup1.cif">10.1107/S1600536808032030/xu2453sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-64-o2226-sup1.cif" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material content-type="local-data" xlink:href="e-64-o2226-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/S1600536808032030/xu2453Isup2.hkl">10.1107/S1600536808032030/xu2453Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-64-o2226-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?xu2453&file=xu2453sup0.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?xu2453sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?xu2453&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?xu2453">XU2453</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>The work was supported by the Science and Technology Project of Zhejiang Province (grant Nos. 2004 C22008 and 2006 C12088) and the National Natural Science Foundation of China (grant No. 30600002).</p>
</ack>
<app-group><app><title>supplementary crystallographic 
information</title>
<sec id="comment"><title>Comment </title>
<p>Bostrycin, a nonspecific phytotoxin, was identified as a metabolite of the
fungus Arthrinium phaeospermum in 1975 (van Eijk,  1975;
Charudattan & Rao,
1982). It is active against Bacillus subtilis but inactive against the
fungus
Geotrichum candidum (Charudattan & Rao, 1982). We report here the
crystal
structure of the title compound.</p>
<p>The crystal structure of the title compound is the average structure of
two tautomers,
5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-
1,4-dione (I) and
1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-
9,10-dione (II). The molecular structures of the two tautomers are shown
in Fig. 1 and Fig. 2, respectively. Both of tautomer molecules contains
three six-membered rings, among which the C9-containing ring displays a
half-chair conformation. Within the molecule the carbonyl group is hydrogen
bonded to the neighboring hydroxyl group(s). The bond distances and angles
agree with those found in a derivative of bostrycin, bostrycin acetonide (Kelly
& Saha, 1985). The extensive O—H···O hydrogen bonding network helps
to
stabilize the crystal structure (Table 1).</p>
</sec>
<sec id="experimental"><title>Experimental </title>
<p>For morphological identification (Arthrinium <italic>sp</italic>. (CGMCC 2082), a fungi
from Polygonum hydropiper <italic>L</italic>.) cultures were grown on OA, PDA, and SNA
media for 7–14 days at room temperature (293 K) under ambient daylight.
Microscopic observations and measurements were made from slides mounted in
water. For metabolite production, the strains were inoculated onto PDA media
and incubated for 10 days at 298 K in the dark. Selected strains were also
cultivated in liquid media placed in a rotary shaker at 120 rpm for 7 days at
298 K in the dark. After cultivation, the bottles were stored at 253 K until
extraction.</p>
<p>Liquid cultures were extracted with trichloromethane. The trichloromethane
phase was filtered and evaporated <italic>in vacuo</italic>. Samples were then
redissolved in trichloromethane, then filtered to remove solid. The
trichloromethane solution was evaporated <italic>in vacuo</italic>. The single crystals
were obtained from an ethanol solution.</p>
</sec>
<sec id="refinement"><title>Refinement </title>
<p>Hydroxyl H atoms were located in a difference Fourier map and refined as riding
in as-found relative positions with <italic>U</italic>
<sub>iso</sub>
(H) = 1.5<italic>U</italic>
<sub>eq</sub>(O).
Methyl H atoms were placed in calculated positions with C—H = 0.96 Å and
torsion angles were refined to fit the electron density, <italic>U</italic>
<sub>iso</sub>(H) =
1.5<italic>U</italic>
<sub>eq</sub>(C). Other H atoms were placed in calculated positions with
C—H = 0.93 (aromatic), 0.97 (methylene) or 0.98 Å (methine), and refined
in riding mode with <italic>U</italic>
<sub>iso</sub>
(H) = 1.2<italic>U</italic>
<sub>eq</sub>(C). In the absence of
significant anomalous scattering effects, Friedel pairs were merged; the
absolute configuration was not determined.</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>The molecular structure of (I) with 50% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed line indicates hydrogen bonding.</p>
</caption>
<graphic xlink:href="e-64-o2226-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>The molecular structure of (II) with 50% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed line indicates hydrogen bonding.</p>
</caption>
<graphic xlink:href="e-64-o2226-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>16</sub>
O<sub>8</sub>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 352</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 336.29</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
 = 1.579 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71069 Å</td>
</tr>
<tr><td rowspan="1" colspan="1">Hall symbol:  P 2yb</td>
<td rowspan="1" colspan="1">Cell parameters from 5814 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 8.280 (2) Å</td>
<td rowspan="1" colspan="1">θ = 6.1–54.9°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 6.644 (2) Å</td>
<td rowspan="1" colspan="1">µ = 0.13 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 13.1535 (12) Å</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 293 K</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 102.12 (2)°</td>
<td rowspan="1" colspan="1">Chunk, red</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 707.5 (3)  Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.30 × 0.20 × 0.08 mm</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
 = 2</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapdatacollectionlong"><title>Data collection</title>
<table-wrap position="anchor" id="d1e266"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Rigaku R-AXIS RAPID IP diffractometer</td>
<td rowspan="1" colspan="1">1517 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td>
<td rowspan="1" colspan="1">1282 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">graphite</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.025</td>
</tr>
<tr><td rowspan="1" colspan="1">Detector resolution: 10 pixels mm<sup>-1</sup>
</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 26.0°, θ<sub>min</sub>
 = 3.2°</td>
</tr>
<tr><td rowspan="1" colspan="1">ω scans</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −10→10</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (ABSCOR; Higashi, 1995)</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −8→8</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.953, <italic>T</italic>
<sub>max</sub>
 = 0.990</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −16→16</td>
</tr>
<tr><td rowspan="1" colspan="1">6151 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="d1e383"><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">Secondary atom site location: difference Fourier map</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.035</td>
<td rowspan="1" colspan="1">H-atom parameters constrained</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.105</td>
<td rowspan="1" colspan="1"><italic>w</italic>
  =  1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0667<italic>P</italic>
)<sup>2</sup>
 + 0.0817<italic>P</italic>
]  where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.08</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 = 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1">1517 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.24 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">220 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.19 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">1 restraint</td>
<td rowspan="1" colspan="1">Extinction correction: SHELXL97 (Sheldrick, 2008), Fc<sup>*</sup>
=kFc[1+0.001xFc<sup>2</sup>
λ<sup>3</sup>
/sin(2θ)]<sup>-1/4</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1">Extinction coefficient: 0.009 (3)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e560"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'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
<italic>wR</italic>
 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) <italic>etc</italic>.
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="d1e659"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1">Occ. (<1)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.4354 (2)</td>
<td rowspan="1" colspan="1">0.3424 (4)</td>
<td rowspan="1" colspan="1">0.34450 (13)</td>
<td rowspan="1" colspan="1">0.0399 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1A</td>
<td rowspan="1" colspan="1">0.5153</td>
<td rowspan="1" colspan="1">0.3341</td>
<td rowspan="1" colspan="1">0.3968</td>
<td rowspan="1" colspan="1">0.060*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.1814 (2)</td>
<td rowspan="1" colspan="1">0.3555 (4)</td>
<td rowspan="1" colspan="1">0.19361 (12)</td>
<td rowspan="1" colspan="1">0.0414 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">−0.1725 (2)</td>
<td rowspan="1" colspan="1">0.3863 (4)</td>
<td rowspan="1" colspan="1">0.43528 (13)</td>
<td rowspan="1" colspan="1">0.0384 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3A</td>
<td rowspan="1" colspan="1">−0.1659</td>
<td rowspan="1" colspan="1">0.3844</td>
<td rowspan="1" colspan="1">0.4995</td>
<td rowspan="1" colspan="1">0.058*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">−0.0420 (2)</td>
<td rowspan="1" colspan="1">0.3933 (4)</td>
<td rowspan="1" colspan="1">0.63061 (13)</td>
<td rowspan="1" colspan="1">0.0370 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4A</td>
<td rowspan="1" colspan="1">−0.1226</td>
<td rowspan="1" colspan="1">0.4012</td>
<td rowspan="1" colspan="1">0.5725</td>
<td rowspan="1" colspan="1">0.055*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">O5</td>
<td rowspan="1" colspan="1">0.1000 (3)</td>
<td rowspan="1" colspan="1">0.2810 (5)</td>
<td rowspan="1" colspan="1">0.82507 (17)</td>
<td rowspan="1" colspan="1">0.0571 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H5A</td>
<td rowspan="1" colspan="1">0.0233</td>
<td rowspan="1" colspan="1">0.2963</td>
<td rowspan="1" colspan="1">0.7644</td>
<td rowspan="1" colspan="1">0.086*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O6</td>
<td rowspan="1" colspan="1">0.3619 (2)</td>
<td rowspan="1" colspan="1">0.4004 (4)</td>
<td rowspan="1" colspan="1">0.97960 (12)</td>
<td rowspan="1" colspan="1">0.0417 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H6A</td>
<td rowspan="1" colspan="1">0.4364</td>
<td rowspan="1" colspan="1">0.3205</td>
<td rowspan="1" colspan="1">1.0303</td>
<td rowspan="1" colspan="1">0.063*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O7</td>
<td rowspan="1" colspan="1">0.5068 (2)</td>
<td rowspan="1" colspan="1">0.6526 (3)</td>
<td rowspan="1" colspan="1">0.84879 (13)</td>
<td rowspan="1" colspan="1">0.0336 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7A</td>
<td rowspan="1" colspan="1">0.5511</td>
<td rowspan="1" colspan="1">0.7105</td>
<td rowspan="1" colspan="1">0.7990</td>
<td rowspan="1" colspan="1">0.050*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O8</td>
<td rowspan="1" colspan="1">0.5671 (2)</td>
<td rowspan="1" colspan="1">0.3429 (4)</td>
<td rowspan="1" colspan="1">0.54013 (13)</td>
<td rowspan="1" colspan="1">0.0401 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.5559</td>
<td rowspan="1" colspan="1">0.3636</td>
<td rowspan="1" colspan="1">0.4666</td>
<td rowspan="1" colspan="1">0.060*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.2943 (3)</td>
<td rowspan="1" colspan="1">0.3552 (4)</td>
<td rowspan="1" colspan="1">0.37142 (18)</td>
<td rowspan="1" colspan="1">0.0302 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.1464 (3)</td>
<td rowspan="1" colspan="1">0.3632 (4)</td>
<td rowspan="1" colspan="1">0.28875 (18)</td>
<td rowspan="1" colspan="1">0.0303 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">−0.0063 (3)</td>
<td rowspan="1" colspan="1">0.3742 (5)</td>
<td rowspan="1" colspan="1">0.31216 (18)</td>
<td rowspan="1" colspan="1">0.0314 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3</td>
<td rowspan="1" colspan="1">−0.0996</td>
<td rowspan="1" colspan="1">0.3781</td>
<td rowspan="1" colspan="1">0.2587</td>
<td rowspan="1" colspan="1">0.038*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">−0.0247 (3)</td>
<td rowspan="1" colspan="1">0.3798 (4)</td>
<td rowspan="1" colspan="1">0.41735 (18)</td>
<td rowspan="1" colspan="1">0.0284 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.1177 (3)</td>
<td rowspan="1" colspan="1">0.3742 (4)</td>
<td rowspan="1" colspan="1">0.50050 (17)</td>
<td rowspan="1" colspan="1">0.0263 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.1023 (3)</td>
<td rowspan="1" colspan="1">0.3820 (4)</td>
<td rowspan="1" colspan="1">0.60602 (17)</td>
<td rowspan="1" colspan="1">0.0268 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.2492 (3)</td>
<td rowspan="1" colspan="1">0.3761 (5)</td>
<td rowspan="1" colspan="1">0.68900 (17)</td>
<td rowspan="1" colspan="1">0.0291 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.2301 (3)</td>
<td rowspan="1" colspan="1">0.3980 (5)</td>
<td rowspan="1" colspan="1">0.80142 (17)</td>
<td rowspan="1" colspan="1">0.0311 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8</td>
<td rowspan="1" colspan="1">0.2063</td>
<td rowspan="1" colspan="1">0.5396</td>
<td rowspan="1" colspan="1">0.8130</td>
<td rowspan="1" colspan="1">0.037*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.3863 (3)</td>
<td rowspan="1" colspan="1">0.3403 (4)</td>
<td rowspan="1" colspan="1">0.87974 (18)</td>
<td rowspan="1" colspan="1">0.0323 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9</td>
<td rowspan="1" colspan="1">0.3996</td>
<td rowspan="1" colspan="1">0.1938</td>
<td rowspan="1" colspan="1">0.8790</td>
<td rowspan="1" colspan="1">0.039*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.5382 (3)</td>
<td rowspan="1" colspan="1">0.4387 (4)</td>
<td rowspan="1" colspan="1">0.85300 (17)</td>
<td rowspan="1" colspan="1">0.0309 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.5585 (3)</td>
<td rowspan="1" colspan="1">0.3595 (5)</td>
<td rowspan="1" colspan="1">0.74721 (17)</td>
<td rowspan="1" colspan="1">0.0319 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.6425</td>
<td rowspan="1" colspan="1">0.4383</td>
<td rowspan="1" colspan="1">0.7240</td>
<td rowspan="1" colspan="1">0.038*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.5970</td>
<td rowspan="1" colspan="1">0.2213</td>
<td rowspan="1" colspan="1">0.7552</td>
<td rowspan="1" colspan="1">0.038*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.4022 (3)</td>
<td rowspan="1" colspan="1">0.3671 (4)</td>
<td rowspan="1" colspan="1">0.66537 (17)</td>
<td rowspan="1" colspan="1">0.0294 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.4195 (3)</td>
<td rowspan="1" colspan="1">0.3563 (4)</td>
<td rowspan="1" colspan="1">0.55826 (18)</td>
<td rowspan="1" colspan="1">0.0296 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.2770 (3)</td>
<td rowspan="1" colspan="1">0.3626 (4)</td>
<td rowspan="1" colspan="1">0.47627 (17)</td>
<td rowspan="1" colspan="1">0.0262 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0456 (3)</td>
<td rowspan="1" colspan="1">0.3549 (6)</td>
<td rowspan="1" colspan="1">0.10420 (18)</td>
<td rowspan="1" colspan="1">0.0435 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15A</td>
<td rowspan="1" colspan="1">−0.0220</td>
<td rowspan="1" colspan="1">0.2384</td>
<td rowspan="1" colspan="1">0.1068</td>
<td rowspan="1" colspan="1">0.065*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15B</td>
<td rowspan="1" colspan="1">0.0881</td>
<td rowspan="1" colspan="1">0.3517</td>
<td rowspan="1" colspan="1">0.0417</td>
<td rowspan="1" colspan="1">0.065*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15C</td>
<td rowspan="1" colspan="1">−0.0196</td>
<td rowspan="1" colspan="1">0.4743</td>
<td rowspan="1" colspan="1">0.1048</td>
<td rowspan="1" colspan="1">0.065*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.6936 (3)</td>
<td rowspan="1" colspan="1">0.3933 (6)</td>
<td rowspan="1" colspan="1">0.93488 (19)</td>
<td rowspan="1" colspan="1">0.0408 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16A</td>
<td rowspan="1" colspan="1">0.7885</td>
<td rowspan="1" colspan="1">0.4434</td>
<td rowspan="1" colspan="1">0.9117</td>
<td rowspan="1" colspan="1">0.061*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16B</td>
<td rowspan="1" colspan="1">0.7039</td>
<td rowspan="1" colspan="1">0.2505</td>
<td rowspan="1" colspan="1">0.9453</td>
<td rowspan="1" colspan="1">0.061*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16C</td>
<td rowspan="1" colspan="1">0.6861</td>
<td rowspan="1" colspan="1">0.4575</td>
<td rowspan="1" colspan="1">0.9991</td>
<td rowspan="1" colspan="1">0.061*</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="d1e1225"><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">0.0294 (10)</td>
<td rowspan="1" colspan="1">0.0644 (15)</td>
<td rowspan="1" colspan="1">0.0268 (8)</td>
<td rowspan="1" colspan="1">0.0039 (10)</td>
<td rowspan="1" colspan="1">0.0076 (7)</td>
<td rowspan="1" colspan="1">−0.0058 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0318 (10)</td>
<td rowspan="1" colspan="1">0.0719 (15)</td>
<td rowspan="1" colspan="1">0.0203 (7)</td>
<td rowspan="1" colspan="1">0.0052 (11)</td>
<td rowspan="1" colspan="1">0.0050 (7)</td>
<td rowspan="1" colspan="1">−0.0025 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.0233 (9)</td>
<td rowspan="1" colspan="1">0.0584 (13)</td>
<td rowspan="1" colspan="1">0.0343 (9)</td>
<td rowspan="1" colspan="1">0.0031 (10)</td>
<td rowspan="1" colspan="1">0.0082 (7)</td>
<td rowspan="1" colspan="1">0.0005 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.0279 (10)</td>
<td rowspan="1" colspan="1">0.0541 (12)</td>
<td rowspan="1" colspan="1">0.0311 (8)</td>
<td rowspan="1" colspan="1">−0.0002 (10)</td>
<td rowspan="1" colspan="1">0.0112 (7)</td>
<td rowspan="1" colspan="1">−0.0016 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O5</td>
<td rowspan="1" colspan="1">0.0513 (14)</td>
<td rowspan="1" colspan="1">0.0811 (19)</td>
<td rowspan="1" colspan="1">0.0421 (11)</td>
<td rowspan="1" colspan="1">−0.0192 (13)</td>
<td rowspan="1" colspan="1">0.0170 (10)</td>
<td rowspan="1" colspan="1">0.0069 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">O6</td>
<td rowspan="1" colspan="1">0.0528 (12)</td>
<td rowspan="1" colspan="1">0.0518 (12)</td>
<td rowspan="1" colspan="1">0.0226 (8)</td>
<td rowspan="1" colspan="1">0.0093 (11)</td>
<td rowspan="1" colspan="1">0.0126 (8)</td>
<td rowspan="1" colspan="1">0.0056 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O7</td>
<td rowspan="1" colspan="1">0.0444 (11)</td>
<td rowspan="1" colspan="1">0.0318 (10)</td>
<td rowspan="1" colspan="1">0.0262 (8)</td>
<td rowspan="1" colspan="1">−0.0028 (9)</td>
<td rowspan="1" colspan="1">0.0112 (7)</td>
<td rowspan="1" colspan="1">0.0001 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">O8</td>
<td rowspan="1" colspan="1">0.0223 (9)</td>
<td rowspan="1" colspan="1">0.0710 (16)</td>
<td rowspan="1" colspan="1">0.0279 (8)</td>
<td rowspan="1" colspan="1">0.0015 (10)</td>
<td rowspan="1" colspan="1">0.0073 (7)</td>
<td rowspan="1" colspan="1">−0.0065 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0294 (13)</td>
<td rowspan="1" colspan="1">0.0370 (15)</td>
<td rowspan="1" colspan="1">0.0262 (11)</td>
<td rowspan="1" colspan="1">0.0026 (13)</td>
<td rowspan="1" colspan="1">0.0101 (9)</td>
<td rowspan="1" colspan="1">−0.0003 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0326 (14)</td>
<td rowspan="1" colspan="1">0.0360 (15)</td>
<td rowspan="1" colspan="1">0.0233 (11)</td>
<td rowspan="1" colspan="1">0.0014 (14)</td>
<td rowspan="1" colspan="1">0.0079 (9)</td>
<td rowspan="1" colspan="1">−0.0003 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0298 (13)</td>
<td rowspan="1" colspan="1">0.0360 (14)</td>
<td rowspan="1" colspan="1">0.0274 (11)</td>
<td rowspan="1" colspan="1">0.0032 (13)</td>
<td rowspan="1" colspan="1">0.0035 (9)</td>
<td rowspan="1" colspan="1">0.0003 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0249 (13)</td>
<td rowspan="1" colspan="1">0.0297 (13)</td>
<td rowspan="1" colspan="1">0.0307 (11)</td>
<td rowspan="1" colspan="1">0.0012 (12)</td>
<td rowspan="1" colspan="1">0.0064 (9)</td>
<td rowspan="1" colspan="1">0.0003 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0274 (13)</td>
<td rowspan="1" colspan="1">0.0282 (12)</td>
<td rowspan="1" colspan="1">0.0249 (11)</td>
<td rowspan="1" colspan="1">0.0006 (12)</td>
<td rowspan="1" colspan="1">0.0089 (9)</td>
<td rowspan="1" colspan="1">0.0005 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0267 (12)</td>
<td rowspan="1" colspan="1">0.0279 (12)</td>
<td rowspan="1" colspan="1">0.0278 (11)</td>
<td rowspan="1" colspan="1">−0.0006 (12)</td>
<td rowspan="1" colspan="1">0.0103 (9)</td>
<td rowspan="1" colspan="1">−0.0021 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0317 (13)</td>
<td rowspan="1" colspan="1">0.0334 (13)</td>
<td rowspan="1" colspan="1">0.0245 (11)</td>
<td rowspan="1" colspan="1">−0.0020 (13)</td>
<td rowspan="1" colspan="1">0.0108 (9)</td>
<td rowspan="1" colspan="1">−0.0003 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0335 (14)</td>
<td rowspan="1" colspan="1">0.0369 (14)</td>
<td rowspan="1" colspan="1">0.0261 (11)</td>
<td rowspan="1" colspan="1">−0.0011 (12)</td>
<td rowspan="1" colspan="1">0.0137 (10)</td>
<td rowspan="1" colspan="1">0.0017 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0411 (15)</td>
<td rowspan="1" colspan="1">0.0348 (14)</td>
<td rowspan="1" colspan="1">0.0232 (10)</td>
<td rowspan="1" colspan="1">0.0016 (13)</td>
<td rowspan="1" colspan="1">0.0117 (10)</td>
<td rowspan="1" colspan="1">0.0021 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0363 (15)</td>
<td rowspan="1" colspan="1">0.0338 (15)</td>
<td rowspan="1" colspan="1">0.0224 (12)</td>
<td rowspan="1" colspan="1">0.0012 (12)</td>
<td rowspan="1" colspan="1">0.0055 (10)</td>
<td rowspan="1" colspan="1">0.0004 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.0283 (13)</td>
<td rowspan="1" colspan="1">0.0429 (16)</td>
<td rowspan="1" colspan="1">0.0251 (11)</td>
<td rowspan="1" colspan="1">0.0016 (13)</td>
<td rowspan="1" colspan="1">0.0067 (9)</td>
<td rowspan="1" colspan="1">−0.0028 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.0304 (13)</td>
<td rowspan="1" colspan="1">0.0340 (14)</td>
<td rowspan="1" colspan="1">0.0248 (11)</td>
<td rowspan="1" colspan="1">0.0024 (13)</td>
<td rowspan="1" colspan="1">0.0079 (9)</td>
<td rowspan="1" colspan="1">−0.0028 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.0270 (13)</td>
<td rowspan="1" colspan="1">0.0370 (15)</td>
<td rowspan="1" colspan="1">0.0262 (11)</td>
<td rowspan="1" colspan="1">0.0028 (12)</td>
<td rowspan="1" colspan="1">0.0087 (9)</td>
<td rowspan="1" colspan="1">−0.0019 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.0250 (12)</td>
<td rowspan="1" colspan="1">0.0309 (13)</td>
<td rowspan="1" colspan="1">0.0230 (10)</td>
<td rowspan="1" colspan="1">0.0014 (12)</td>
<td rowspan="1" colspan="1">0.0059 (9)</td>
<td rowspan="1" colspan="1">−0.0019 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0381 (15)</td>
<td rowspan="1" colspan="1">0.068 (2)</td>
<td rowspan="1" colspan="1">0.0225 (11)</td>
<td rowspan="1" colspan="1">0.0052 (17)</td>
<td rowspan="1" colspan="1">0.0028 (10)</td>
<td rowspan="1" colspan="1">−0.0018 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.0368 (15)</td>
<td rowspan="1" colspan="1">0.0555 (17)</td>
<td rowspan="1" colspan="1">0.0279 (12)</td>
<td rowspan="1" colspan="1">0.0023 (15)</td>
<td rowspan="1" colspan="1">0.0019 (10)</td>
<td rowspan="1" colspan="1">−0.0011 (14)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title>
<table-wrap position="anchor" id="d1e1672"><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—C1</td>
<td rowspan="1" colspan="1">1.293 (3)</td>
<td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.421 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—H1A</td>
<td rowspan="1" colspan="1">0.8501</td>
<td rowspan="1" colspan="1">C5—C14</td>
<td rowspan="1" colspan="1">1.423 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C2</td>
<td rowspan="1" colspan="1">1.344 (3)</td>
<td rowspan="1" colspan="1">C6—C7</td>
<td rowspan="1" colspan="1">1.454 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C15</td>
<td rowspan="1" colspan="1">1.447 (3)</td>
<td rowspan="1" colspan="1">C7—C12</td>
<td rowspan="1" colspan="1">1.368 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—C4</td>
<td rowspan="1" colspan="1">1.294 (3)</td>
<td rowspan="1" colspan="1">C7—C8</td>
<td rowspan="1" colspan="1">1.527 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—H3A</td>
<td rowspan="1" colspan="1">0.8350</td>
<td rowspan="1" colspan="1">C8—C9</td>
<td rowspan="1" colspan="1">1.524 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C6</td>
<td rowspan="1" colspan="1">1.304 (3)</td>
<td rowspan="1" colspan="1">C8—H8</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—H4A</td>
<td rowspan="1" colspan="1">0.9046</td>
<td rowspan="1" colspan="1">C9—C10</td>
<td rowspan="1" colspan="1">1.523 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">O5—C8</td>
<td rowspan="1" colspan="1">1.415 (4)</td>
<td rowspan="1" colspan="1">C9—H9</td>
<td rowspan="1" colspan="1">0.9800</td>
</tr>
<tr><td rowspan="1" colspan="1">O5—H5A</td>
<td rowspan="1" colspan="1">0.9154</td>
<td rowspan="1" colspan="1">C10—C16</td>
<td rowspan="1" colspan="1">1.525 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O6—C9</td>
<td rowspan="1" colspan="1">1.427 (3)</td>
<td rowspan="1" colspan="1">C10—C11</td>
<td rowspan="1" colspan="1">1.530 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O6—H6A</td>
<td rowspan="1" colspan="1">0.9667</td>
<td rowspan="1" colspan="1">C11—C12</td>
<td rowspan="1" colspan="1">1.501 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O7—C10</td>
<td rowspan="1" colspan="1">1.444 (3)</td>
<td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">O7—H7A</td>
<td rowspan="1" colspan="1">0.9012</td>
<td rowspan="1" colspan="1">C11—H11B</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">O8—C13</td>
<td rowspan="1" colspan="1">1.296 (3)</td>
<td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.448 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O8—H8A</td>
<td rowspan="1" colspan="1">0.9624</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.422 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C14</td>
<td rowspan="1" colspan="1">1.417 (3)</td>
<td rowspan="1" colspan="1">C15—H15A</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.458 (3)</td>
<td rowspan="1" colspan="1">C15—H15B</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.364 (4)</td>
<td rowspan="1" colspan="1">C15—H15C</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.424 (3)</td>
<td rowspan="1" colspan="1">C16—H16A</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C16—H16B</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.431 (3)</td>
<td rowspan="1" colspan="1">C16—H16C</td>
<td rowspan="1" colspan="1">0.9600</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">C1—O1—H1A</td>
<td rowspan="1" colspan="1">112.1</td>
<td rowspan="1" colspan="1">C10—C9—C8</td>
<td rowspan="1" colspan="1">111.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—O2—C15</td>
<td rowspan="1" colspan="1">118.3 (2)</td>
<td rowspan="1" colspan="1">O6—C9—H9</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—O3—H3A</td>
<td rowspan="1" colspan="1">108.7</td>
<td rowspan="1" colspan="1">C10—C9—H9</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—O4—H4A</td>
<td rowspan="1" colspan="1">110.2</td>
<td rowspan="1" colspan="1">C8—C9—H9</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—O5—H5A</td>
<td rowspan="1" colspan="1">99.7</td>
<td rowspan="1" colspan="1">O7—C10—C9</td>
<td rowspan="1" colspan="1">106.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—O6—H6A</td>
<td rowspan="1" colspan="1">106.8</td>
<td rowspan="1" colspan="1">O7—C10—C16</td>
<td rowspan="1" colspan="1">109.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—O7—H7A</td>
<td rowspan="1" colspan="1">110.5</td>
<td rowspan="1" colspan="1">C9—C10—C16</td>
<td rowspan="1" colspan="1">111.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13—O8—H8A</td>
<td rowspan="1" colspan="1">106.3</td>
<td rowspan="1" colspan="1">O7—C10—C11</td>
<td rowspan="1" colspan="1">110.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1—C14</td>
<td rowspan="1" colspan="1">123.4 (2)</td>
<td rowspan="1" colspan="1">C9—C10—C11</td>
<td rowspan="1" colspan="1">108.4 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1—C2</td>
<td rowspan="1" colspan="1">117.6 (2)</td>
<td rowspan="1" colspan="1">C16—C10—C11</td>
<td rowspan="1" colspan="1">109.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14—C1—C2</td>
<td rowspan="1" colspan="1">119.0 (2)</td>
<td rowspan="1" colspan="1">C12—C11—C10</td>
<td rowspan="1" colspan="1">113.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C2—C3</td>
<td rowspan="1" colspan="1">127.1 (2)</td>
<td rowspan="1" colspan="1">C12—C11—H11A</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C2—C1</td>
<td rowspan="1" colspan="1">112.4 (2)</td>
<td rowspan="1" colspan="1">C10—C11—H11A</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—C1</td>
<td rowspan="1" colspan="1">120.4 (2)</td>
<td rowspan="1" colspan="1">C12—C11—H11B</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4</td>
<td rowspan="1" colspan="1">120.9 (2)</td>
<td rowspan="1" colspan="1">C10—C11—H11B</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3</td>
<td rowspan="1" colspan="1">119.5</td>
<td rowspan="1" colspan="1">H11A—C11—H11B</td>
<td rowspan="1" colspan="1">107.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3</td>
<td rowspan="1" colspan="1">119.5</td>
<td rowspan="1" colspan="1">C7—C12—C13</td>
<td rowspan="1" colspan="1">120.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—C4—C3</td>
<td rowspan="1" colspan="1">118.4 (2)</td>
<td rowspan="1" colspan="1">C7—C12—C11</td>
<td rowspan="1" colspan="1">122.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—C4—C5</td>
<td rowspan="1" colspan="1">121.4 (2)</td>
<td rowspan="1" colspan="1">C13—C12—C11</td>
<td rowspan="1" colspan="1">116.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5</td>
<td rowspan="1" colspan="1">120.2 (2)</td>
<td rowspan="1" colspan="1">O8—C13—C14</td>
<td rowspan="1" colspan="1">121.8 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C14</td>
<td rowspan="1" colspan="1">119.9 (2)</td>
<td rowspan="1" colspan="1">O8—C13—C12</td>
<td rowspan="1" colspan="1">118.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—C4</td>
<td rowspan="1" colspan="1">121.1 (2)</td>
<td rowspan="1" colspan="1">C14—C13—C12</td>
<td rowspan="1" colspan="1">120.1 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14—C5—C4</td>
<td rowspan="1" colspan="1">119.0 (2)</td>
<td rowspan="1" colspan="1">C1—C14—C13</td>
<td rowspan="1" colspan="1">120.0 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C6—C5</td>
<td rowspan="1" colspan="1">121.3 (2)</td>
<td rowspan="1" colspan="1">C1—C14—C5</td>
<td rowspan="1" colspan="1">120.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C6—C7</td>
<td rowspan="1" colspan="1">118.7 (2)</td>
<td rowspan="1" colspan="1">C13—C14—C5</td>
<td rowspan="1" colspan="1">119.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—C7</td>
<td rowspan="1" colspan="1">120.0 (2)</td>
<td rowspan="1" colspan="1">O2—C15—H15A</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">119.9 (2)</td>
<td rowspan="1" colspan="1">O2—C15—H15B</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">120.9 (2)</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—C7—C8</td>
<td rowspan="1" colspan="1">119.0 (2)</td>
<td rowspan="1" colspan="1">O2—C15—H15C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O5—C8—C9</td>
<td rowspan="1" colspan="1">106.9 (2)</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">O5—C8—C7</td>
<td rowspan="1" colspan="1">113.5 (2)</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">C9—C8—C7</td>
<td rowspan="1" colspan="1">112.6 (2)</td>
<td rowspan="1" colspan="1">C10—C16—H16A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O5—C8—H8</td>
<td rowspan="1" colspan="1">107.8</td>
<td rowspan="1" colspan="1">C10—C16—H16B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C8—H8</td>
<td rowspan="1" colspan="1">107.8</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">C7—C8—H8</td>
<td rowspan="1" colspan="1">107.8</td>
<td rowspan="1" colspan="1">C10—C16—H16C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O6—C9—C10</td>
<td rowspan="1" colspan="1">112.1 (2)</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">O6—C9—C8</td>
<td rowspan="1" colspan="1">106.7 (2)</td>
<td rowspan="1" colspan="1">H16B—C16—H16C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title>
<table-wrap position="anchor" id="d1e2229"><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">O1—H1A···O3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.85</td>
<td rowspan="1" colspan="1">2.55</td>
<td rowspan="1" colspan="1">3.229 (3)</td>
<td rowspan="1" colspan="1">137</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—H3A···O8<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.84</td>
<td rowspan="1" colspan="1">2.40</td>
<td rowspan="1" colspan="1">2.808 (3)</td>
<td rowspan="1" colspan="1">111</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—H4A···O8<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.90</td>
<td rowspan="1" colspan="1">2.54</td>
<td rowspan="1" colspan="1">3.223 (3)</td>
<td rowspan="1" colspan="1">132</td>
</tr>
<tr><td rowspan="1" colspan="1">O5—H5A···O4</td>
<td rowspan="1" colspan="1">0.92</td>
<td rowspan="1" colspan="1">1.85</td>
<td rowspan="1" colspan="1">2.687 (3)</td>
<td rowspan="1" colspan="1">152</td>
</tr>
<tr><td rowspan="1" colspan="1">O6—H6A···O7<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">0.97</td>
<td rowspan="1" colspan="1">1.92</td>
<td rowspan="1" colspan="1">2.821 (3)</td>
<td rowspan="1" colspan="1">154</td>
</tr>
<tr><td rowspan="1" colspan="1">O7—H7A···O1<sup>iv</sup>
</td>
<td rowspan="1" colspan="1">0.90</td>
<td rowspan="1" colspan="1">2.11</td>
<td rowspan="1" colspan="1">2.966 (3)</td>
<td rowspan="1" colspan="1">159</td>
</tr>
<tr><td rowspan="1" colspan="1">O7—H7A···O2<sup>iv</sup>
</td>
<td rowspan="1" colspan="1">0.90</td>
<td rowspan="1" colspan="1">2.40</td>
<td rowspan="1" colspan="1">3.066 (3)</td>
<td rowspan="1" colspan="1">131</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) <italic>x</italic>
+1, <italic>y</italic>
, <italic>z</italic>
; (ii) <italic>x</italic>
−1, <italic>y</italic>
, <italic>z</italic>
; (iii) −<italic>x</italic>
+1, <italic>y</italic>
−1/2, −<italic>z</italic>
+2; (iv) −<italic>x</italic>
+1, <italic>y</italic>
+1/2, −<italic>z</italic>
+1.</p>
</sec>
</app>
</app-group>
<ref-list><title>References</title>
<ref id="bb1"><mixed-citation publication-type="other">Charudattan, R. & Rao, K. V. (1982). <italic>Appl. Environ. Microbiol.</italic>
<bold>43</bold>
, 846–849.</mixed-citation>
</ref>
<ref id="bb2"><mixed-citation publication-type="other">Eijk, G. W. van (1975). <italic>Cell. Mol. Life Sci.</italic>
<bold>31</bold>
, 783–784.</mixed-citation>
</ref>
<ref id="bb3"><mixed-citation publication-type="other">Farrugia, L. J. (1997). <italic>J. Appl. Cryst.</italic>
<bold>30</bold>
, 565.</mixed-citation>
</ref>
<ref id="bb4"><mixed-citation publication-type="other">Farrugia, L. J. (1999). <italic>J. Appl. Cryst.</italic>
<bold>32</bold>
, 837–838.</mixed-citation>
</ref>
<ref id="bb5"><mixed-citation publication-type="other">Higashi, T. (1995). <italic>ABSCOR</italic>
 Rigaku Corporation, Tokyo, Japan.</mixed-citation>
</ref>
<ref id="bb6"><mixed-citation publication-type="other">Kelly, T. & Saha, J. K. (1985). <italic>J. Org. Chem.</italic>
<bold>50</bold>
, 3679–3685.</mixed-citation>
</ref>
<ref id="bb7"><mixed-citation publication-type="other">Rigaku (1998). <italic>PROCESS-AUTO</italic>
 Rigaku Corporation, Tokyo, Japan.</mixed-citation>
</ref>
<ref id="bb8"><mixed-citation publication-type="other">Rigaku/MSC (2002). <italic>CrystalStructure</italic>
 Rigaku/MSC, The Woodlands, Texas, USA.</mixed-citation>
</ref>
<ref id="bb9"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic>
 A<bold>64</bold>
, 112–122.</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">O1—H1<italic>A</italic>
⋯O3<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.85</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.55</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.229 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">137</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O3—H3<italic>A</italic>
⋯O8<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.40</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.808 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">111</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O4—H4<italic>A</italic>
⋯O8<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.90</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.54</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.223 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">132</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O5—H5<italic>A</italic>
⋯O4</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.92</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.85</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.687 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">152</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O6—H6<italic>A</italic>
⋯O7<sup>iii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.97</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.92</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.821 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">154</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O7—H7<italic>A</italic>
⋯O1<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.90</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.11</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.966 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">159</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O7—H7<italic>A</italic>
⋯O2<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.90</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.40</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.066 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">131</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iii) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iv) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>

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