2-Oxo-2H-chromen-4-yl 4-methoxybenzoate
Identifieur interne : 000993 ( Pmc/Corpus ); précédent : 000992; suivant : 0009942-Oxo-2H-chromen-4-yl 4-methoxybenzoate
Auteurs : Akoun Abou ; Abdoulaye Djandé ; Grégoire Danger ; Adama Saba ; Rita Kakou-YaoSource :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2012.
Abstract
In the title molecule, C17H12O5, the chromen-2-one ring and the 4-methoxybenzoate side chain are inclined to one another at a dihedral angle of 69.82 (9)°. The crystal structure features parallel sheets of centrosymmetric
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DOI: 10.1107/S1600536812047666
PubMed: 23476255
PubMed Central: 3589019
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">2-Oxo-2<italic>H</italic>-chromen-4-yl 4-methoxybenzoate</title><author><name sortKey="Abou, Akoun" sort="Abou, Akoun" uniqKey="Abou A" first="Akoun" last="Abou">Akoun Abou</name><affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d’Ivoire</nlm:aff></affiliation></author><author><name sortKey="Djande, Abdoulaye" sort="Djande, Abdoulaye" uniqKey="Djande A" first="Abdoulaye" last="Djandé">Abdoulaye Djandé</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03,<country>Burkina Faso</country></nlm:aff></affiliation></author><author><name sortKey="Danger, Gregoire" sort="Danger, Gregoire" uniqKey="Danger G" first="Grégoire" last="Danger">Grégoire Danger</name><affiliation><nlm:aff id="c">Laboratoire de Physique des Interactions Ioniques et Moléculaires, Equipe-Spectrométries et Dynamique Moléculaire, Centre Saint Jérôme, Université de Provence, 13397 Marseille,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Saba, Adama" sort="Saba, Adama" uniqKey="Saba A" first="Adama" last="Saba">Adama Saba</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03,<country>Burkina Faso</country></nlm:aff></affiliation></author><author><name sortKey="Kakou Yao, Rita" sort="Kakou Yao, Rita" uniqKey="Kakou Yao R" first="Rita" last="Kakou-Yao">Rita Kakou-Yao</name><affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d’Ivoire</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">23476255</idno><idno type="pmc">3589019</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3589019</idno><idno type="RBID">PMC:3589019</idno><idno type="doi">10.1107/S1600536812047666</idno><date when="2012">2012</date><idno type="wicri:Area/Pmc/Corpus">000993</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000993</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">2-Oxo-2<italic>H</italic>-chromen-4-yl 4-methoxybenzoate</title><author><name sortKey="Abou, Akoun" sort="Abou, Akoun" uniqKey="Abou A" first="Akoun" last="Abou">Akoun Abou</name><affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d’Ivoire</nlm:aff></affiliation></author><author><name sortKey="Djande, Abdoulaye" sort="Djande, Abdoulaye" uniqKey="Djande A" first="Abdoulaye" last="Djandé">Abdoulaye Djandé</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03,<country>Burkina Faso</country></nlm:aff></affiliation></author><author><name sortKey="Danger, Gregoire" sort="Danger, Gregoire" uniqKey="Danger G" first="Grégoire" last="Danger">Grégoire Danger</name><affiliation><nlm:aff id="c">Laboratoire de Physique des Interactions Ioniques et Moléculaires, Equipe-Spectrométries et Dynamique Moléculaire, Centre Saint Jérôme, Université de Provence, 13397 Marseille,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Saba, Adama" sort="Saba, Adama" uniqKey="Saba A" first="Adama" last="Saba">Adama Saba</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03,<country>Burkina Faso</country></nlm:aff></affiliation></author><author><name sortKey="Kakou Yao, Rita" sort="Kakou Yao, Rita" uniqKey="Kakou Yao R" first="Rita" last="Kakou-Yao">Rita Kakou-Yao</name><affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d’Ivoire</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="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the title molecule, C<sub>17</sub>H<sub>12</sub>O<sub>5</sub>, the chromen-2-one ring and the 4-methoxybenzoate side chain are inclined to one another at a dihedral angle of 69.82 (9)°. The crystal structure features parallel sheets of centrosymmetric <italic>R</italic><sub>2</sub><sup>2</sup>(6) dimers joined by a <italic>C</italic>(7) chain, resulting in centrosymetric tetramers of hydrogen-bonded molecules with graph-set motif <italic>R</italic><sub>4</sub><sup>4</sup>(40). These centrosymetric tetramers are connected by a pair of hydrogen bonds described by an <italic>R</italic><sub>2</sub><sup>2</sup>(8) ring motif and a <italic>C</italic>(7) chain <italic>via</italic> C—H⋯O interactions. In the structure, there are also π–π stacking interactions between chromene benzene and the six-membered heterocyclic rings [centroid–centroid distance = 3.691 (2) Å] and weak C=O⋯π interactions [O⋯(ring centroid) distance = 3.357 (3) Å].</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></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="iso-abbrev">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">23476255</article-id><article-id pub-id-type="pmc">3589019</article-id><article-id pub-id-type="publisher-id">zs2245</article-id><article-id pub-id-type="doi">10.1107/S1600536812047666</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536812047666</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title>2-Oxo-2<italic>H</italic>-chromen-4-yl 4-methoxybenzoate</article-title><alt-title><italic>C<sub>17</sub>H<sub>12</sub>O<sub>5</sub></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Abou</surname><given-names>Akoun</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>Djandé</surname><given-names>Abdoulaye</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Danger</surname><given-names>Grégoire</given-names></name><xref ref-type="aff" rid="c">c</xref></contrib><contrib contrib-type="author"><name><surname>Saba</surname><given-names>Adama</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Kakou-Yao</surname><given-names>Rita</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><aff id="a"><label>a</label>Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d’Ivoire</aff><aff id="b"><label>b</label>Laboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03,<country>Burkina Faso</country></aff><aff id="c"><label>c</label>Laboratoire de Physique des Interactions Ioniques et Moléculaires, Equipe-Spectrométries et Dynamique Moléculaire, Centre Saint Jérôme, Université de Provence, 13397 Marseille,<country>France</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>abou_akoun@yahoo.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>12</month><year>2012</year></pub-date><pub-date pub-type="epub"><day>24</day><month>11</month><year>2012</year></pub-date><pub-date pub-type="pmc-release"><day>24</day><month>11</month><year>2012</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>68</volume><issue>Pt 12</issue><issue-id pub-id-type="publisher-id">e121200</issue-id><fpage>o3438</fpage><lpage>o3439</lpage><history><date date-type="received"><day>08</day><month>11</month><year>2012</year></date><date date-type="accepted"><day>20</day><month>11</month><year>2012</year></date></history><permissions><copyright-statement>© Abou et al. 2012</copyright-statement><copyright-year>2012</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/S1600536812047666">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>In the title molecule, C<sub>17</sub>H<sub>12</sub>O<sub>5</sub>, the chromen-2-one ring and the 4-methoxybenzoate side chain are inclined to one another at a dihedral angle of 69.82 (9)°. The crystal structure features parallel sheets of centrosymmetric <italic>R</italic><sub>2</sub><sup>2</sup>(6) dimers joined by a <italic>C</italic>(7) chain, resulting in centrosymetric tetramers of hydrogen-bonded molecules with graph-set motif <italic>R</italic><sub>4</sub><sup>4</sup>(40). These centrosymetric tetramers are connected by a pair of hydrogen bonds described by an <italic>R</italic><sub>2</sub><sup>2</sup>(8) ring motif and a <italic>C</italic>(7) chain <italic>via</italic> C—H⋯O interactions. In the structure, there are also π–π stacking interactions between chromene benzene and the six-membered heterocyclic rings [centroid–centroid distance = 3.691 (2) Å] and weak C=O⋯π interactions [O⋯(ring centroid) distance = 3.357 (3) Å].</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature
</title><p>For the biological activity of coumarin derivatives, see: Basanagouda <italic>et al.</italic> (2009<xref ref-type="bibr" rid="bb1"> ▶</xref>); Vukovic <italic>et al.</italic> (2010<xref ref-type="bibr" rid="bb12"> ▶</xref>); Emmanuel-Giota <italic>et al.</italic> (2001<xref ref-type="bibr" rid="bb4"> ▶</xref>); Marchenko <italic>et al.</italic> (2006<xref ref-type="bibr" rid="bb8"> ▶</xref>). For hydrogen-bond motifs, see: Bernstein <italic>et al.</italic> (1995<xref ref-type="bibr" rid="bb2"> ▶</xref>). For π–π stacking interactions, see: Janiak (2000<xref ref-type="bibr" rid="bb7"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-68-o3438-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec 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>17</sub>H<sub>12</sub>O<sub>5</sub></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 296.27</p></list-item><list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-68-o3438-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 4.371 (1) Å</p></list-item><list-item><p><italic>b</italic> = 10.535 (4) Å</p></list-item><list-item><p><italic>c</italic> = 15.193 (2) Å</p></list-item><list-item><p>α = 85.218 (3)°</p></list-item><list-item><p>β = 83.688 (2)°</p></list-item><list-item><p>γ = 81.893 (1)°</p></list-item><list-item><p><italic>V</italic> = 686.8 (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 = 0.11 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 298 K</p></list-item><list-item><p>0.25 × 0.15 × 0.04 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection
</title><p><list list-type="simple"><list-item><p>Nonius KappaCCD diffractometer</p></list-item><list-item><p>5683 measured reflections</p></list-item><list-item><p>2731 independent reflections</p></list-item><list-item><p>1540 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.055</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>)] = 0.066</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.163</p></list-item><list-item><p><italic>S</italic> = 1.11</p></list-item><list-item><p>2731 reflections</p></list-item><list-item><p>200 parameters</p></list-item><list-item><p>H-atom parameters constrained</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="d5e503"><title></title><p>Data collection: <italic>COLLECT</italic> (Hooft, 1998<xref ref-type="bibr" rid="bb6"> ▶</xref>); cell refinement: <italic>DENZO</italic>/<italic>SCALEPACK</italic> (Otwinowski & Minor, 1997<xref ref-type="bibr" rid="bb9"> ▶</xref>); data reduction: <italic>DENZO</italic>/<italic>SCALEPACK</italic>; program(s) used to solve structure: <italic>SIR2004</italic> (Burla <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb3"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb10"> ▶</xref>); molecular graphics: <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb11"> ▶</xref>); software used to prepare material for publication: <italic>SHELXL97</italic>, <italic>publCIF</italic> (Westrip, 2010<xref ref-type="bibr" rid="bb13"> ▶</xref>) and <italic>WinGX</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb5"> ▶</xref>).</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><media xlink:href="e-68-o3438-sup1.cif" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p></caption></media><p>Crystal structure: contains datablock(s) I, global. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536812047666/zs2245sup1.cif">10.1107/S1600536812047666/zs2245sup1.cif</ext-link></p><media xlink:href="e-68-o3438-sup1.cif" xlink:type="simple" id="d34e144" position="anchor" mimetype="text" mime-subtype="plain"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-68-o3438-Isup2.hkl" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p></caption></media><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536812047666/zs2245Isup2.hkl">10.1107/S1600536812047666/zs2245Isup2.hkl</ext-link></p><media xlink:href="e-68-o3438-Isup2.hkl" xlink:type="simple" id="d34e151" position="anchor" mimetype="text" mime-subtype="plain"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-68-o3438-Isup3.cml" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p></caption></media><p>Supplementary material file. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536812047666/zs2245Isup3.cml">10.1107/S1600536812047666/zs2245Isup3.cml</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?zs2245&file=zs2245sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?zs2245sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?zs2245&checkcif=yes">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?zs2245">ZS2245</ext-link>).</p></fn></fn-group><ack><p>The authors thank the Spectropôle Service of the Faculty of Sciences and Techniques of Saint Jérôme (France) for the use of the diffractometer and the NMR spectrometer.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>Coumarin constitutes one of the major classes of naturally occurring compounds
and interest in its chemistry continues unabated because of its usefulness as
a biologically active agent. It also represents the core structure of several
molecules of pharmaceutical importance. Coumarin and its derivatives have been
reported to serve as anti-bacterial (Basanagouda <italic>et al.</italic>, 2009),
anti-oxidant (Vukovic <italic>et al.</italic>, 2010), anti-inflammatory
(Emmanuel-Giota
<italic>et al.</italic>, 2001) and anti-tumour agents (Marchenko, <italic>et al.</italic>,
2006).
Therefore, the synthesis of new coumarin derivatives is of considerable
interest. In order to study the influence of new substituents on the activity
of the coumarin derivatives, the title compound, the ester C<sub>17</sub>H<sub>12</sub>O<sub>5</sub> has
been synthesized and its molecular and crystal structure is reported herein.</p><p>In the title compound (Fig. 1), the side chain is tilted with respect to the
chromen-2-one ring with torsion angles C1—C9—O3—C10 = -76.3 (4)° and
C8—C9—O3—C10 = 107.7 (3)°. The dihedral angle between the chromene ring
and the side chain is 69.82 (9) °.</p><p>In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table
1) generate hydrogen-bonding motifs ranging from a chain to various rings.
Indeed, in the methoxy group, an H atom of the methyl group (H17<italic>B</italic>)
bonds to the oxygen atom of the same group on a neighbouring molecule (related
by an inversion center) to form parallel sheets of centrosymetric dimers
[graph set <italic>R</italic><sub>2</sub><sup>2</sup>(6) (Bernstein <italic>et al.</italic>, 1995)]. Also, a
hydrogen of the chromene-benzene ring (H2) bonds to the oxygen atom of the
carbonyl group of the side chain of a neighbouring molecule to form an
infinite chain [graph set <italic>C</italic>(7)]. The combination of the <italic>C</italic>(7)
chain and the <italic>R</italic><sub>2</sub><sup>2</sup>(6) dimers results in a ring of hydrogen-bonded
molecules described by the graph set <italic>R</italic><sub>4</sub><sup>4</sup>(40) (Fig. 2). Further, the
hydrogen of the six-membered heterocyclic ring bonds to the oxygen atom of the
carbonyl group of the chromen-2-one moiety of an inversion-related
neighbouring molecule to form a pair of hydrogen bonds [graph set
<italic>R</italic><sub>2</sub><sup>2</sup>(8)]. The latter hydrogen bonds and the <italic>C</italic>(7) chain
connect the <italic>R</italic><sub>4</sub><sup>4</sup>(40) centrosymmetric tetramers, resulting in a
supramolecular aggregation (Fig. 3) which is further consolidated by weak
C═ O···π interactions [O2···<italic>Cg</italic>1 (<italic>x</italic> - 1, <italic>y</italic>, <italic>z</italic>)
= 3.357 (3) Å], where <italic>Cg</italic>1 is the centroid of the six-membered O
containing ring, and π–π stacking between the chromene-benzene C1—C6 and
the six-membered heterocyclic rings; in the latter, the centroid···centroid
distance, [<italic>Cg</italic>2···<italic>Cg</italic>1 (<italic>x</italic> + 1, <italic>y</italic>, <italic>z</italic>) or
<italic>Cg</italic>1···<italic>Cg</italic>2 (<italic>x</italic> - 1, <italic>y</italic>, <italic>z</italic>) = 3.691 (2) Å], is
less than 3.8 Å, the maximum regarded as relevant for π–π interactions
(Janiak, 2000) (Fig. 4).</p></sec><sec id="experimental"><title>Experimental </title><p>To a solution of 4-methoxybenzoyl chloride (40 mmol) in dried tetrahydrofuran
(150 ml), was added dried triethylamine (120 mmol) and 4-hydroxycoumarin (40 mmol)in small portions over 30 min. The mixture was then refluxed for 3 h and
poured in 300 ml of chloroform. The solution was acidified with dilute
hydrochloric acid until the pH was 2–3. The organic layer was extracted,
washed with water, dried over MgSO<sub>4</sub> and the solvent removed. The crude
product was recrystallized from chloroform. Colourless crystals of the title
compound were obtained in a good yield (84%); m.p. 421–422 K.
<sup>1</sup>H NMR (Bruker TOPSPIN, CDCl<sub>3</sub>, 400 MHz, p.p.m.) δ: 6.63 (s, 1H, H8); 7.43
(d, 1H, H2); 7.33 (t.d, 1H, H3); 7.61 (t.d,1<italic>H</italic>, H4); 7.73 (d, 1H, H5);
8.2 (d, 2H, H12 and H16); 7.05 (d, 2H, H13 and H15); 3.93 (s, 3H, CH<sub>3</sub>).
<sup>13</sup>C NMR (Bruker TOPSPIN, CDCl<sub>3</sub>, 100 MHz, p.p.m.) δ: 162 (C7); 108 (C8);
161 (C9); 127 (C2); 124 (C3); 117 (C4); 126 (C5); 153 (C6); 115 (C1); 165
(C10); 160 (C11); 133 (C12 and C16); 113 (C13 and C15); 120 (C14); 55 (C17).</p></sec><sec id="refinement"><title>Refinement </title><p>H atoms were placed in calculated positions [C—H = 0.93 (aromatic) or 0.96 Å
(methyl group)] and refined using a riding model approximation with
<italic>U</italic><sub>iso</sub>(H) constrained to 1.2 (aromatic) or 1.5 (methyl) times
<italic>U</italic><sub>eq</sub> of the respective parent atom.
The five reflections (1 - 5 17), (0 - 1 1), (0 0 1),
(0 1 0), (1 0 1) were found
to have too low intensities, caused by a systematic
error, probably by shielding
by the beam stop interference. They were omitted from the refinement.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level. H atoms are shown as spheres of arbitrary radius.</p></caption><graphic xlink:href="e-68-o3438-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>The crystal packing, viewed down the c axis, showing parallel sheets of centrosymmetric R22(6) dimers linked by an infinite C(7) chain to form a centrosymetric R44(40) tetramers. The dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity.</p></caption><graphic xlink:href="e-68-o3438-fig2"></graphic></fig><fig id="Fap3"><label>Fig. 3.</label><caption><p>The crystal packing, viewed down the c axis, showing the supramolecular aggregation formed by the propagation of the centrosymetric R44(40) tetramers via C—H···O hydrogen bonds. The dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.</p></caption><graphic xlink:href="e-68-o3438-fig3"></graphic></fig><fig id="Fap4"><label>Fig. 4.</label><caption><p>A view of the crystal packing, showing C═O···π and π–π stacking interactions (dashed lines). The green dots are centroids of rings. H atoms have been omitted.</p></caption><graphic xlink:href="e-68-o3438-fig4"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e342"><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>17</sub>H<sub>12</sub>O<sub>5</sub></td><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 296.27</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 308</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.433 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 1</td><td rowspan="1" colspan="1">Melting point = 421–422 K</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 4.371 (1) Å</td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 10.535 (4) Å</td><td rowspan="1" colspan="1">Cell parameters from 5683 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 15.193 (2) Å</td><td rowspan="1" colspan="1">θ = 2.3–27.0°</td></tr><tr><td rowspan="1" colspan="1">α = 85.218 (3)°</td><td rowspan="1" colspan="1">µ = 0.11 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 83.688 (2)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 298 K</td></tr><tr><td rowspan="1" colspan="1">γ = 81.893 (1)°</td><td rowspan="1" colspan="1">Prism, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 686.8 (3) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.25 × 0.15 × 0.04 mm</td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e476"><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">Nonius KappaCCD diffractometer</td><td rowspan="1" colspan="1">1540 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.055</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 27.0°, θ<sub>min</sub> = 2.3°</td></tr><tr><td rowspan="1" colspan="1">φ and ω scans</td><td rowspan="1" colspan="1"><italic>h</italic> = 0→5</td></tr><tr><td rowspan="1" colspan="1">5683 measured reflections</td><td rowspan="1" colspan="1"><italic>k</italic> = −12→13</td></tr><tr><td rowspan="1" colspan="1">2731 independent reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −18→19</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e571"><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>)] = 0.066</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>) = 0.163</td><td rowspan="1" colspan="1">H-atom parameters constrained</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>) + (0.0324<italic>P</italic>)<sup>2</sup> + 0.5861<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">2731 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">200 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><tr><td rowspan="1" colspan="1">48 constraints</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e732"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.</td></tr><tr><td rowspan="1" colspan="1">Refinement. Refinement of <italic>F</italic><sup>2</sup> against ALL reflections. The weighted <italic>R</italic>-factor
<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> >
2σ(<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="d1e831"><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">O3</td><td rowspan="1" colspan="1">0.1598 (5)</td><td rowspan="1" colspan="1">0.05340 (19)</td><td rowspan="1" colspan="1">0.31179 (13)</td><td rowspan="1" colspan="1">0.0542 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">−0.3230 (5)</td><td rowspan="1" colspan="1">0.3325 (2)</td><td rowspan="1" colspan="1">0.47003 (14)</td><td rowspan="1" colspan="1">0.0528 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">−0.5808 (6)</td><td rowspan="1" colspan="1">0.1879 (2)</td><td rowspan="1" colspan="1">0.54685 (17)</td><td rowspan="1" colspan="1">0.0722 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.2683 (7)</td><td rowspan="1" colspan="1">−0.0573 (3)</td><td rowspan="1" colspan="1">0.1811 (2)</td><td rowspan="1" colspan="1">0.0447 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">−0.1068 (6)</td><td rowspan="1" colspan="1">0.1288 (2)</td><td rowspan="1" colspan="1">0.19569 (15)</td><td rowspan="1" colspan="1">0.0656 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.7433 (6)</td><td rowspan="1" colspan="1">−0.3598 (2)</td><td rowspan="1" colspan="1">0.04518 (16)</td><td rowspan="1" colspan="1">0.0702 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">−0.0670 (8)</td><td rowspan="1" colspan="1">0.4966 (3)</td><td rowspan="1" colspan="1">0.3926 (2)</td><td rowspan="1" colspan="1">0.0525 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">−0.1839</td><td rowspan="1" colspan="1">0.5552</td><td rowspan="1" colspan="1">0.4297</td><td rowspan="1" colspan="1">0.063*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">−0.0098 (7)</td><td rowspan="1" colspan="1">0.1490 (3)</td><td rowspan="1" colspan="1">0.3629 (2)</td><td rowspan="1" colspan="1">0.0459 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0601 (7)</td><td rowspan="1" colspan="1">0.2784 (3)</td><td rowspan="1" colspan="1">0.3473 (2)</td><td rowspan="1" colspan="1">0.0443 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">−0.1068 (7)</td><td rowspan="1" colspan="1">0.3679 (3)</td><td rowspan="1" colspan="1">0.4027 (2)</td><td rowspan="1" colspan="1">0.0455 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.5790 (7)</td><td rowspan="1" colspan="1">−0.2567 (3)</td><td rowspan="1" colspan="1">0.0861 (2)</td><td rowspan="1" colspan="1">0.0512 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0876 (8)</td><td rowspan="1" colspan="1">0.0505 (3)</td><td rowspan="1" colspan="1">0.2267 (2)</td><td rowspan="1" colspan="1">0.0500 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.1473 (8)</td><td rowspan="1" colspan="1">0.5360 (3)</td><td rowspan="1" colspan="1">0.3273 (2)</td><td rowspan="1" colspan="1">0.0586 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.1758</td><td rowspan="1" colspan="1">0.6222</td><td rowspan="1" colspan="1">0.3199</td><td rowspan="1" colspan="1">0.070*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">−0.3849 (8)</td><td rowspan="1" colspan="1">0.2081 (3)</td><td rowspan="1" colspan="1">0.4861 (2)</td><td rowspan="1" colspan="1">0.0532 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.4725 (7)</td><td rowspan="1" colspan="1">−0.1501 (3)</td><td rowspan="1" colspan="1">0.2215 (2)</td><td rowspan="1" colspan="1">0.0510 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.5054</td><td rowspan="1" colspan="1">−0.1455</td><td rowspan="1" colspan="1">0.2805</td><td rowspan="1" colspan="1">0.061*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.3792 (8)</td><td rowspan="1" colspan="1">−0.1649 (3)</td><td rowspan="1" colspan="1">0.0454 (2)</td><td rowspan="1" colspan="1">0.0612 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.3468</td><td rowspan="1" colspan="1">−0.1691</td><td rowspan="1" colspan="1">−0.0138</td><td rowspan="1" colspan="1">0.073*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">−0.2172 (8)</td><td rowspan="1" colspan="1">0.1147 (3)</td><td rowspan="1" colspan="1">0.4278 (2)</td><td rowspan="1" colspan="1">0.0520 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">−0.2550</td><td rowspan="1" colspan="1">0.0296</td><td rowspan="1" colspan="1">0.4359</td><td rowspan="1" colspan="1">0.062*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.6278 (8)</td><td rowspan="1" colspan="1">−0.2498 (3)</td><td rowspan="1" colspan="1">0.1738 (2)</td><td rowspan="1" colspan="1">0.0565 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.7656</td><td rowspan="1" colspan="1">−0.3125</td><td rowspan="1" colspan="1">0.2008</td><td rowspan="1" colspan="1">0.068*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.2264 (8)</td><td rowspan="1" colspan="1">−0.0658 (3)</td><td rowspan="1" colspan="1">0.0939 (2)</td><td rowspan="1" colspan="1">0.0618 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.0905</td><td rowspan="1" colspan="1">−0.0027</td><td rowspan="1" colspan="1">0.0665</td><td rowspan="1" colspan="1">0.074*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.3223 (8)</td><td rowspan="1" colspan="1">0.4490 (3)</td><td rowspan="1" colspan="1">0.2719 (2)</td><td rowspan="1" colspan="1">0.0585 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.4692</td><td rowspan="1" colspan="1">0.4768</td><td rowspan="1" colspan="1">0.2283</td><td rowspan="1" colspan="1">0.070*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.2795 (7)</td><td rowspan="1" colspan="1">0.3217 (3)</td><td rowspan="1" colspan="1">0.2813 (2)</td><td rowspan="1" colspan="1">0.0525 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.3965</td><td rowspan="1" colspan="1">0.2639</td><td rowspan="1" colspan="1">0.2437</td><td rowspan="1" colspan="1">0.063*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.7156 (10)</td><td rowspan="1" colspan="1">−0.3667 (4)</td><td rowspan="1" colspan="1">−0.0473 (2)</td><td rowspan="1" colspan="1">0.0784 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17A</td><td rowspan="1" colspan="1">0.5023</td><td rowspan="1" colspan="1">−0.3692</td><td rowspan="1" colspan="1">−0.0560</td><td rowspan="1" colspan="1">0.118*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17B</td><td rowspan="1" colspan="1">0.8401</td><td rowspan="1" colspan="1">−0.4429</td><td rowspan="1" colspan="1">−0.0680</td><td rowspan="1" colspan="1">0.118*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17C</td><td rowspan="1" colspan="1">0.7859</td><td rowspan="1" colspan="1">−0.2924</td><td rowspan="1" colspan="1">−0.0800</td><td rowspan="1" colspan="1">0.118*</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="d1e1338"><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">O3</td><td rowspan="1" colspan="1">0.0695 (15)</td><td rowspan="1" colspan="1">0.0459 (12)</td><td rowspan="1" colspan="1">0.0453 (13)</td><td rowspan="1" colspan="1">0.0091 (10)</td><td rowspan="1" colspan="1">−0.0096 (11)</td><td rowspan="1" colspan="1">−0.0155 (10)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0634 (14)</td><td rowspan="1" colspan="1">0.0459 (13)</td><td rowspan="1" colspan="1">0.0478 (13)</td><td rowspan="1" colspan="1">−0.0031 (10)</td><td rowspan="1" colspan="1">0.0020 (11)</td><td rowspan="1" colspan="1">−0.0138 (10)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0892 (19)</td><td rowspan="1" colspan="1">0.0661 (16)</td><td rowspan="1" colspan="1">0.0575 (16)</td><td rowspan="1" colspan="1">−0.0115 (13)</td><td rowspan="1" colspan="1">0.0144 (14)</td><td rowspan="1" colspan="1">−0.0096 (12)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0515 (19)</td><td rowspan="1" colspan="1">0.0393 (17)</td><td rowspan="1" colspan="1">0.0429 (18)</td><td rowspan="1" colspan="1">−0.0017 (13)</td><td rowspan="1" colspan="1">−0.0024 (14)</td><td rowspan="1" colspan="1">−0.0103 (14)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0724 (16)</td><td rowspan="1" colspan="1">0.0624 (15)</td><td rowspan="1" colspan="1">0.0601 (15)</td><td rowspan="1" colspan="1">0.0189 (12)</td><td rowspan="1" colspan="1">−0.0207 (13)</td><td rowspan="1" colspan="1">−0.0215 (12)</td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.0938 (19)</td><td rowspan="1" colspan="1">0.0529 (14)</td><td rowspan="1" colspan="1">0.0594 (16)</td><td rowspan="1" colspan="1">0.0174 (13)</td><td rowspan="1" colspan="1">−0.0090 (13)</td><td rowspan="1" colspan="1">−0.0219 (12)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.060 (2)</td><td rowspan="1" colspan="1">0.0451 (19)</td><td rowspan="1" colspan="1">0.054 (2)</td><td rowspan="1" colspan="1">0.0007 (15)</td><td rowspan="1" colspan="1">−0.0131 (17)</td><td rowspan="1" colspan="1">−0.0166 (15)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.057 (2)</td><td rowspan="1" colspan="1">0.0391 (17)</td><td rowspan="1" colspan="1">0.0418 (18)</td><td rowspan="1" colspan="1">0.0060 (14)</td><td rowspan="1" colspan="1">−0.0117 (16)</td><td rowspan="1" colspan="1">−0.0130 (14)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0482 (18)</td><td rowspan="1" colspan="1">0.0443 (18)</td><td rowspan="1" colspan="1">0.0404 (17)</td><td rowspan="1" colspan="1">0.0026 (14)</td><td rowspan="1" colspan="1">−0.0096 (14)</td><td rowspan="1" colspan="1">−0.0106 (14)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0508 (19)</td><td rowspan="1" colspan="1">0.0458 (18)</td><td rowspan="1" colspan="1">0.0407 (18)</td><td rowspan="1" colspan="1">−0.0030 (14)</td><td rowspan="1" colspan="1">−0.0080 (15)</td><td rowspan="1" colspan="1">−0.0095 (14)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.060 (2)</td><td rowspan="1" colspan="1">0.0394 (17)</td><td rowspan="1" colspan="1">0.053 (2)</td><td rowspan="1" colspan="1">0.0007 (15)</td><td rowspan="1" colspan="1">−0.0023 (16)</td><td rowspan="1" colspan="1">−0.0139 (15)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.055 (2)</td><td rowspan="1" colspan="1">0.0488 (19)</td><td rowspan="1" colspan="1">0.047 (2)</td><td rowspan="1" colspan="1">−0.0023 (16)</td><td rowspan="1" colspan="1">−0.0085 (16)</td><td rowspan="1" colspan="1">−0.0116 (15)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.070 (2)</td><td rowspan="1" colspan="1">0.047 (2)</td><td rowspan="1" colspan="1">0.061 (2)</td><td rowspan="1" colspan="1">−0.0107 (17)</td><td rowspan="1" colspan="1">−0.0139 (19)</td><td rowspan="1" colspan="1">−0.0028 (17)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.065 (2)</td><td rowspan="1" colspan="1">0.049 (2)</td><td rowspan="1" colspan="1">0.045 (2)</td><td rowspan="1" colspan="1">−0.0026 (16)</td><td rowspan="1" colspan="1">−0.0074 (17)</td><td rowspan="1" colspan="1">−0.0086 (15)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.063 (2)</td><td rowspan="1" colspan="1">0.0443 (18)</td><td rowspan="1" colspan="1">0.0452 (19)</td><td rowspan="1" colspan="1">−0.0020 (15)</td><td rowspan="1" colspan="1">−0.0084 (16)</td><td rowspan="1" colspan="1">−0.0076 (15)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.077 (2)</td><td rowspan="1" colspan="1">0.059 (2)</td><td rowspan="1" colspan="1">0.047 (2)</td><td rowspan="1" colspan="1">0.0108 (18)</td><td rowspan="1" colspan="1">−0.0159 (18)</td><td rowspan="1" colspan="1">−0.0186 (17)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.066 (2)</td><td rowspan="1" colspan="1">0.0430 (18)</td><td rowspan="1" colspan="1">0.0464 (19)</td><td rowspan="1" colspan="1">−0.0012 (15)</td><td rowspan="1" colspan="1">−0.0070 (17)</td><td rowspan="1" colspan="1">−0.0073 (15)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.071 (2)</td><td rowspan="1" colspan="1">0.0420 (18)</td><td rowspan="1" colspan="1">0.053 (2)</td><td rowspan="1" colspan="1">0.0105 (16)</td><td rowspan="1" colspan="1">−0.0108 (17)</td><td rowspan="1" colspan="1">−0.0073 (16)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.078 (2)</td><td rowspan="1" colspan="1">0.054 (2)</td><td rowspan="1" colspan="1">0.051 (2)</td><td rowspan="1" colspan="1">0.0165 (17)</td><td rowspan="1" colspan="1">−0.0171 (18)</td><td rowspan="1" colspan="1">−0.0157 (17)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.065 (2)</td><td rowspan="1" colspan="1">0.062 (2)</td><td rowspan="1" colspan="1">0.051 (2)</td><td rowspan="1" colspan="1">−0.0137 (17)</td><td rowspan="1" colspan="1">−0.0056 (17)</td><td rowspan="1" colspan="1">−0.0051 (17)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.056 (2)</td><td rowspan="1" colspan="1">0.057 (2)</td><td rowspan="1" colspan="1">0.0447 (19)</td><td rowspan="1" colspan="1">0.0012 (16)</td><td rowspan="1" colspan="1">−0.0072 (16)</td><td rowspan="1" colspan="1">−0.0129 (15)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.103 (3)</td><td rowspan="1" colspan="1">0.071 (3)</td><td rowspan="1" colspan="1">0.057 (2)</td><td rowspan="1" colspan="1">0.015 (2)</td><td rowspan="1" colspan="1">−0.006 (2)</td><td rowspan="1" colspan="1">−0.029 (2)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1819"><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">O3—C10</td><td rowspan="1" colspan="1">1.368 (4)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.365 (4)</td></tr><tr><td rowspan="1" colspan="1">O3—C9</td><td rowspan="1" colspan="1">1.400 (3)</td><td rowspan="1" colspan="1">C14—C13</td><td rowspan="1" colspan="1">1.381 (4)</td></tr><tr><td rowspan="1" colspan="1">O1—C7</td><td rowspan="1" colspan="1">1.373 (4)</td><td rowspan="1" colspan="1">C4—C3</td><td rowspan="1" colspan="1">1.387 (5)</td></tr><tr><td rowspan="1" colspan="1">O1—C6</td><td rowspan="1" colspan="1">1.379 (4)</td><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">O2—C7</td><td rowspan="1" colspan="1">1.214 (4)</td><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.445 (4)</td></tr><tr><td rowspan="1" colspan="1">C11—C16</td><td rowspan="1" colspan="1">1.369 (4)</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.381 (4)</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.380 (4)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C11—C10</td><td rowspan="1" colspan="1">1.467 (4)</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.379 (4)</td></tr><tr><td rowspan="1" colspan="1">O4—C10</td><td rowspan="1" colspan="1">1.204 (4)</td><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">O5—C14</td><td rowspan="1" colspan="1">1.370 (3)</td><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">O5—C17</td><td rowspan="1" colspan="1">1.433 (4)</td><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C5—C4</td><td rowspan="1" colspan="1">1.368 (4)</td><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.385 (4)</td><td rowspan="1" colspan="1">C3—C2</td><td rowspan="1" colspan="1">1.373 (4)</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C9—C8</td><td rowspan="1" colspan="1">1.327 (4)</td><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C9—C1</td><td rowspan="1" colspan="1">1.434 (4)</td><td rowspan="1" colspan="1">C17—H17A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.391 (4)</td><td rowspan="1" colspan="1">C17—H17B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.403 (4)</td><td rowspan="1" colspan="1">C17—H17C</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">C10—O3—C9</td><td rowspan="1" colspan="1">117.2 (2)</td><td rowspan="1" colspan="1">O1—C7—C8</td><td rowspan="1" colspan="1">116.9 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—O1—C6</td><td rowspan="1" colspan="1">122.2 (2)</td><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">119.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C16—C11—C12</td><td rowspan="1" colspan="1">119.0 (3)</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">120.2</td></tr><tr><td rowspan="1" colspan="1">C16—C11—C10</td><td rowspan="1" colspan="1">117.4 (3)</td><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">120.2</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C10</td><td rowspan="1" colspan="1">123.6 (3)</td><td rowspan="1" colspan="1">C14—C15—C16</td><td rowspan="1" colspan="1">118.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C14—O5—C17</td><td rowspan="1" colspan="1">117.5 (3)</td><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">120.8</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6</td><td rowspan="1" colspan="1">118.9 (3)</td><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">120.8</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">C9—C8—C7</td><td rowspan="1" colspan="1">120.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C8—C9—O3</td><td rowspan="1" colspan="1">118.5 (3)</td><td rowspan="1" colspan="1">C7—C8—H8</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C1</td><td rowspan="1" colspan="1">122.3 (3)</td><td rowspan="1" colspan="1">C12—C13—C14</td><td rowspan="1" colspan="1">120.2 (3)</td></tr><tr><td rowspan="1" colspan="1">O3—C9—C1</td><td rowspan="1" colspan="1">119.1 (3)</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2</td><td rowspan="1" colspan="1">117.9 (3)</td><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C9</td><td rowspan="1" colspan="1">116.4 (3)</td><td rowspan="1" colspan="1">C11—C16—C15</td><td rowspan="1" colspan="1">122.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C9</td><td rowspan="1" colspan="1">125.7 (3)</td><td rowspan="1" colspan="1">C11—C16—H16</td><td rowspan="1" colspan="1">118.9</td></tr><tr><td rowspan="1" colspan="1">O1—C6—C5</td><td rowspan="1" colspan="1">116.8 (3)</td><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">118.9</td></tr><tr><td rowspan="1" colspan="1">O1—C6—C1</td><td rowspan="1" colspan="1">121.3 (3)</td><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">120.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C1</td><td rowspan="1" colspan="1">121.9 (3)</td><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C15—C14—O5</td><td rowspan="1" colspan="1">123.9 (3)</td><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C15—C14—C13</td><td rowspan="1" colspan="1">120.6 (3)</td><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">120.4 (3)</td></tr><tr><td rowspan="1" colspan="1">O5—C14—C13</td><td rowspan="1" colspan="1">115.5 (3)</td><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">O4—C10—O3</td><td rowspan="1" colspan="1">121.8 (3)</td><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">O4—C10—C11</td><td rowspan="1" colspan="1">125.8 (3)</td><td rowspan="1" colspan="1">O5—C17—H17A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O3—C10—C11</td><td rowspan="1" colspan="1">112.4 (3)</td><td rowspan="1" colspan="1">O5—C17—H17B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">120.8 (3)</td><td rowspan="1" colspan="1">H17A—C17—H17B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">O5—C17—H17C</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">119.6</td><td rowspan="1" colspan="1">H17A—C17—H17C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O2—C7—O1</td><td rowspan="1" colspan="1">116.6 (3)</td><td rowspan="1" colspan="1">H17B—C17—H17C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O2—C7—C8</td><td rowspan="1" colspan="1">126.4 (3)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10—O3—C9—C8</td><td rowspan="1" colspan="1">107.7 (3)</td><td rowspan="1" colspan="1">C6—C5—C4—C3</td><td rowspan="1" colspan="1">0.0 (5)</td></tr><tr><td rowspan="1" colspan="1">C10—O3—C9—C1</td><td rowspan="1" colspan="1">−76.3 (4)</td><td rowspan="1" colspan="1">C6—O1—C7—O2</td><td rowspan="1" colspan="1">−179.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C1—C6</td><td rowspan="1" colspan="1">−1.4 (4)</td><td rowspan="1" colspan="1">C6—O1—C7—C8</td><td rowspan="1" colspan="1">−1.3 (4)</td></tr><tr><td rowspan="1" colspan="1">O3—C9—C1—C6</td><td rowspan="1" colspan="1">−177.3 (3)</td><td rowspan="1" colspan="1">C16—C11—C12—C13</td><td rowspan="1" colspan="1">−0.6 (5)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C1—C2</td><td rowspan="1" colspan="1">178.8 (3)</td><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">178.6 (3)</td></tr><tr><td rowspan="1" colspan="1">O3—C9—C1—C2</td><td rowspan="1" colspan="1">2.9 (5)</td><td rowspan="1" colspan="1">O5—C14—C15—C16</td><td rowspan="1" colspan="1">179.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—O1—C6—C5</td><td rowspan="1" colspan="1">179.5 (3)</td><td rowspan="1" colspan="1">C13—C14—C15—C16</td><td rowspan="1" colspan="1">−0.3 (5)</td></tr><tr><td rowspan="1" colspan="1">C7—O1—C6—C1</td><td rowspan="1" colspan="1">0.1 (4)</td><td rowspan="1" colspan="1">O3—C9—C8—C7</td><td rowspan="1" colspan="1">176.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—O1</td><td rowspan="1" colspan="1">179.4 (3)</td><td rowspan="1" colspan="1">C1—C9—C8—C7</td><td rowspan="1" colspan="1">0.3 (5)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">−1.3 (5)</td><td rowspan="1" colspan="1">O2—C7—C8—C9</td><td rowspan="1" colspan="1">179.3 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—O1</td><td rowspan="1" colspan="1">−179.0 (3)</td><td rowspan="1" colspan="1">O1—C7—C8—C9</td><td rowspan="1" colspan="1">1.1 (5)</td></tr><tr><td rowspan="1" colspan="1">C9—C1—C6—O1</td><td rowspan="1" colspan="1">1.2 (4)</td><td rowspan="1" colspan="1">C11—C12—C13—C14</td><td rowspan="1" colspan="1">0.0 (5)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">1.7 (4)</td><td rowspan="1" colspan="1">C15—C14—C13—C12</td><td rowspan="1" colspan="1">0.5 (5)</td></tr><tr><td rowspan="1" colspan="1">C9—C1—C6—C5</td><td rowspan="1" colspan="1">−178.1 (3)</td><td rowspan="1" colspan="1">O5—C14—C13—C12</td><td rowspan="1" colspan="1">−179.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C17—O5—C14—C15</td><td rowspan="1" colspan="1">3.8 (5)</td><td rowspan="1" colspan="1">C12—C11—C16—C15</td><td rowspan="1" colspan="1">0.7 (5)</td></tr><tr><td rowspan="1" colspan="1">C17—O5—C14—C13</td><td rowspan="1" colspan="1">−176.1 (3)</td><td rowspan="1" colspan="1">C10—C11—C16—C15</td><td rowspan="1" colspan="1">−178.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C9—O3—C10—O4</td><td rowspan="1" colspan="1">2.2 (5)</td><td rowspan="1" colspan="1">C14—C15—C16—C11</td><td rowspan="1" colspan="1">−0.3 (6)</td></tr><tr><td rowspan="1" colspan="1">C9—O3—C10—C11</td><td rowspan="1" colspan="1">−177.0 (3)</td><td rowspan="1" colspan="1">C5—C4—C3—C2</td><td rowspan="1" colspan="1">0.9 (5)</td></tr><tr><td rowspan="1" colspan="1">C16—C11—C10—O4</td><td rowspan="1" colspan="1">4.1 (5)</td><td rowspan="1" colspan="1">C4—C3—C2—C1</td><td rowspan="1" colspan="1">−0.5 (5)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C10—O4</td><td rowspan="1" colspan="1">−175.1 (3)</td><td rowspan="1" colspan="1">C6—C1—C2—C3</td><td rowspan="1" colspan="1">−0.8 (5)</td></tr><tr><td rowspan="1" colspan="1">C16—C11—C10—O3</td><td rowspan="1" colspan="1">−176.7 (3)</td><td rowspan="1" colspan="1">C9—C1—C2—C3</td><td rowspan="1" colspan="1">179.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C10—O3</td><td rowspan="1" colspan="1">4.1 (4)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e2506"><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">C8—H8···O2<sup>i</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.48</td><td rowspan="1" colspan="1">3.407 (4)</td><td rowspan="1" colspan="1">173</td></tr><tr><td rowspan="1" colspan="1">C2—H2···O4<sup>ii</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.49</td><td rowspan="1" colspan="1">3.340 (4)</td><td rowspan="1" colspan="1">151</td></tr><tr><td rowspan="1" colspan="1">C17—H17<italic>B</italic>···O5<sup>iii</sup></td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">2.59</td><td rowspan="1" colspan="1">3.461 (4)</td><td rowspan="1" colspan="1">151</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>−1, −<italic>y</italic>, −<italic>z</italic>+1; (ii) <italic>x</italic>+1, <italic>y</italic>, <italic>z</italic>; (iii) −<italic>x</italic>+2, −<italic>y</italic>−1, −<italic>z</italic>.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Sandhyarani, P. & Rasal, V. P. (2009). <italic>J. Chem. Sci.</italic><bold>121</bold>, 485–495.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). <italic>Angew. Chem. Int. Ed. Engl.</italic><bold>34</bold>, 1555–1573.</mixed-citation></ref><ref id="bb3"><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="bb4"><mixed-citation publication-type="other">Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). <italic>J. Heterocycl. Chem.</italic><bold>38</bold>, 717–722.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Hooft, R. (1998). <italic>COLLECT</italic> Nonius BV, Delft, The Netherlands.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Janiak, C. (2000). <italic>J. Chem. Soc. Dalton Trans.</italic> pp. 3885–3896.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Marchenko, M. M., Kopyl’chuk, G. P., Shmarakov, I. A., Ketsa, O. V. & Kushnir, V. M. (2006). <italic>Pharm. Chem. J.</italic><bold>40</bold>, 296–297.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Otwinowski, Z. & Minor, W. (1997). <italic>Methods in Enzymology</italic>, Vol. 276, <italic>Macromolecular Crystallography</italic>, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Spek, A. L. (2009). <italic>Acta Cryst.</italic> D<bold>65</bold>, 148–155.</mixed-citation></ref><ref id="bb12"><mixed-citation publication-type="other">Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). <italic>Arch. Pharm. Res.</italic><bold>33</bold>, 5–15.</mixed-citation></ref><ref id="bb13"><mixed-citation publication-type="other">Westrip, S. P. (2010). <italic>J. Appl. Cryst.</italic><bold>43</bold>, 920–925.</mixed-citation></ref></ref-list></back><floats-group><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">C8—H8⋯O2<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.48</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.407 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">173</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C2—H2⋯O4<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.49</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.340 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">151</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C17—H17<italic>B</italic>⋯O5<sup>iii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.96</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.59</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.461 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">151</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-68-o3438-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-68-o3438-efi6.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-68-o3438-efi7.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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