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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Di-<italic>tert</italic>-butyl 2-benzoylhydrazine-1,1-dicarboxylate</title><author><name sortKey="Didierjean, Claude" sort="Didierjean, Claude" uniqKey="Didierjean C" first="Claude" last="Didierjean">Claude Didierjean</name><affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux, et Biologiques (LCM3B), UMR n° 7036, Nancy Université, Faculté des Sciences et Techniques, BP 239, 54506 Vandoeuvre lès Nancy Cedex,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Brosse, Nicolas" sort="Brosse, Nicolas" uniqKey="Brosse N" first="Nicolas" last="Brosse">Nicolas Brosse</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Bodiguel, Jacques" sort="Bodiguel, Jacques" uniqKey="Bodiguel J" first="Jacques" last="Bodiguel">Jacques Bodiguel</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Jamart Gregoire, Brigitte" sort="Jamart Gregoire, Brigitte" uniqKey="Jamart Gregoire B" first="Brigitte" last="Jamart-Grégoire">Brigitte Jamart-Grégoire</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21200770</idno><idno type="pmc">2915266</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2915266</idno><idno type="RBID">PMC:2915266</idno><idno type="doi">10.1107/S160053680706391X</idno><date when="2007">2007</date><idno type="wicri:Area/Pmc/Corpus">000175</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000175</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Di-<italic>tert</italic>-butyl 2-benzoylhydrazine-1,1-dicarboxylate</title><author><name sortKey="Didierjean, Claude" sort="Didierjean, Claude" uniqKey="Didierjean C" first="Claude" last="Didierjean">Claude Didierjean</name><affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux, et Biologiques (LCM3B), UMR n° 7036, Nancy Université, Faculté des Sciences et Techniques, BP 239, 54506 Vandoeuvre lès Nancy Cedex,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Brosse, Nicolas" sort="Brosse, Nicolas" uniqKey="Brosse N" first="Nicolas" last="Brosse">Nicolas Brosse</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Bodiguel, Jacques" sort="Bodiguel, Jacques" uniqKey="Bodiguel J" first="Jacques" last="Bodiguel">Jacques Bodiguel</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Jamart Gregoire, Brigitte" sort="Jamart Gregoire, Brigitte" uniqKey="Jamart Gregoire B" first="Brigitte" last="Jamart-Grégoire">Brigitte Jamart-Grégoire</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</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="2007">2007</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The crystal structure of the title compound, C<sub>17</sub>H<sub>24</sub>N<sub>2</sub>O<sub>5</sub>, was determined in the course of our studies on the preparation of two families of pseudopeptides, <italic>viz</italic>. hydrazino- and <italic>N</italic>-amino- peptides. The most significant interaction in the crystal structure is a bifurcated intermolecular N—H⋯O hydrogen bond.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title></journal-title-group><issn pub-type="epub">1600-5368</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">21200770</article-id><article-id pub-id-type="pmc">2915266</article-id><article-id pub-id-type="publisher-id">hj2004</article-id><article-id pub-id-type="doi">10.1107/S160053680706391X</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S160053680706391X</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title>Di-<italic>tert</italic>-butyl 2-benzoylhydrazine-1,1-dicarboxylate</article-title><alt-title><italic>C<sub>17</sub>H<sub>24</sub>N<sub>2</sub>O<sub>5</sub></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Didierjean</surname><given-names>Claude</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>Brosse</surname><given-names>Nicolas</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Bodiguel</surname><given-names>Jacques</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Jamart-Grégoire</surname><given-names>Brigitte</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><aff id="a"><label>a</label>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux, et Biologiques (LCM3B), UMR n° 7036, Nancy Université, Faculté des Sciences et Techniques, BP 239, 54506 Vandoeuvre lès Nancy Cedex,<country>France</country></aff><aff id="b"><label>b</label>Laboratoire de Chimie Physique Macromoléculaire, UMR CNRS-INPL 7568, Nancy-Université, ENSIC 1, rue grandville BP 451, 54001 Nancy,<country>France</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>claude.didierjean@lcm3b.uhp-nancy.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>1</month><year>2008</year></pub-date><pub-date pub-type="epub"><day>06</day><month>12</month><year>2007</year></pub-date><pub-date pub-type="pmc-release"><day>06</day><month>12</month><year>2007</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>64</volume><issue>Pt 1</issue><issue-id pub-id-type="publisher-id">e080100</issue-id><fpage>o205</fpage><lpage>o205</lpage><history><date date-type="received"><day>22</day><month>11</month><year>2007</year></date><date date-type="accepted"><day>27</day><month>11</month><year>2007</year></date></history><permissions><copyright-statement>© International Union of Crystallography 2008</copyright-statement><copyright-year>2008</copyright-year><license license-type="open-access" xlink:href="http://journals.iucr.org/services/termsofuse.html"><license-p>This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html.</license-p></license></permissions><self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S160053680706391X">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>The crystal structure of the title compound, C<sub>17</sub>H<sub>24</sub>N<sub>2</sub>O<sub>5</sub>, was determined in the course of our studies on the preparation of two families of pseudopeptides, <italic>viz</italic>. hydrazino- and <italic>N</italic>-amino- peptides. The most significant interaction in the crystal structure is a bifurcated intermolecular N—H⋯O hydrogen bond.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature</title><p>For the synthesis, see: Brosse <italic>et al.</italic> (2003<xref ref-type="bibr" rid="bb3"> ▶</xref>). For geometry, see: Allen (2002<xref ref-type="bibr" rid="bb1"> ▶</xref>); Kauffmann <italic>et al.</italic> (2004<xref ref-type="bibr" rid="bb7"> ▶</xref>); Fong <italic>et al.</italic> (1996<xref ref-type="bibr" rid="bb6"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-64-0o205-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>17</sub>H<sub>24</sub>N<sub>2</sub>O<sub>5</sub></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 336.38</p></list-item><list-item><p>Orthorhombic, <inline-formula><inline-graphic xlink:href="e-64-0o205-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 9.9794 (2) Å</p></list-item><list-item><p><italic>b</italic> = 11.5763 (3) Å</p></list-item><list-item><p><italic>c</italic> = 16.0720 (4) Å</p></list-item><list-item><p><italic>V</italic> = 1856.71 (8) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 4</p></list-item><list-item><p>Mo <italic>K</italic>α radiation</p></list-item><list-item><p>μ = 0.09 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 293 (2) K</p></list-item><list-item><p>0.3 × 0.05 × 0.05 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 area-detector diffractometer</p></list-item><list-item><p>Absorption correction: none</p></list-item><list-item><p>9649 measured reflections</p></list-item><list-item><p>1944 independent reflections</p></list-item><list-item><p>1559 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.032</p></list-item></list></p></sec><sec id="sec2.1.3"><title>Refinement</title><p><list list-type="simple"><list-item><p><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.038</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.109</p></list-item><list-item><p><italic>S</italic> = 1.03</p></list-item><list-item><p>1944 reflections</p></list-item><list-item><p>226 parameters</p></list-item><list-item><p>H atoms treated by a mixture of independent and constrained refinement</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.16 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.15 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e407"><title></title><p>Data collection: <italic>COLLECT</italic> (Nonius, 1998<xref ref-type="bibr" rid="bb9"> ▶</xref>); cell refinement: <italic>SCALEPACK</italic> (Otwinowski & Minor, 1997<xref ref-type="bibr" rid="bb10"> ▶</xref>); data reduction: <italic>SCALEPACK</italic> and <italic>DENZO</italic> (Otwinowski & Minor, 1997<xref ref-type="bibr" rid="bb10"> ▶</xref>); program(s) used to solve structure: <italic>SIR92</italic> (Altomare <italic>et al.</italic>, 1999<xref ref-type="bibr" rid="bb2"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 1997<xref ref-type="bibr" rid="bb11"> ▶</xref>); molecular graphics: <italic>ORTEP-3 for Windows</italic> (Farrugia, 1997<xref ref-type="bibr" rid="bb4"> ▶</xref>) and <italic>WebLab ViewerPro 3.5</italic> (MSI, 1999<xref ref-type="bibr" rid="bb8"> ▶</xref>); software used to prepare material for publication: <italic>WinGX</italic> publication routines (Farrugia, 1999<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" xlink:href="e-64-0o205-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablocks global, I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S160053680706391X/hj2004sup1.cif">10.1107/S160053680706391X/hj2004sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-64-0o205-sup1.cif" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material content-type="local-data" xlink:href="e-64-0o205-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/S160053680706391X/hj2004Isup2.hkl">10.1107/S160053680706391X/hj2004Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-64-0o205-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?hj2004&file=hj2004sup0.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?hj2004sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hj2004&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?hj2004">HJ2004</ext-link>).</p></fn></fn-group><ack><p>The authors thank the National Research Agency (ANR) for financial support (No. NT05_4_42848) and the Service Commun de Diffraction X (Nancy Université) for providing access to experimental crystallographic facilities.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>As part of our continuing studies on the synthesis and structure of hydrazino-
and <italic>N</italic>-amino-peptides, we have described the crystal structure of
<italic>N</italic>-(<italic>tert</italic>-Butyloxycarbonylamino)phthalimide (Kauffmann <italic>et
al.</italic>, 2004). Here we report the crystal structure of the title compound,
<italic>N</italic>-benzoyl-N<sup>β</sup>, N<sup>α</sup>- bis (<italic>tert</italic>-butoxycarbonyl) hydrazine
(Fig. 1).</p><p>Although the title compound is not chiral, it crystallizes in the
non-centrosymmetric space group <italic>P</italic>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub>. The angle between the
amide plane and the mean plane of the imidodicarbonate group is 78.43 (18)°,
showing that these two groups are nearly perpendicular. The angle between the
best-fit phenyl plane and the amide plane of 27.34 (7)° is similar to that
reported for the benzamide group (Fong <italic>et al.</italic>, 1996).</p><p>In the crystal structure of the title compound, molecules are linked into
infinite chains parallel to a <italic>via</italic> bifurcated N—H···O hydrogen bonds
involving both carbonate of the aminoimidodicarbonate group (Fig. 2). All
other intermolecular interactions are due to van der Waals forces.</p></sec><sec id="experimental"><title>Experimental </title><p>The title compound was prepared from
<italic>N</italic>-(<italic>tert</italic>-Butyloxycarbonylamino)phthalimide (Brosse <italic>et al.</italic>,
2003), and was crystallized by slow evaporation of an ethanol solution.</p></sec><sec id="refinement"><title>Refinement </title><p>All H atoms were located in difference maps. The C-bonded H atoms were placed at
calculated positions and refined using a riding model, with C—H distances of
0.93–0.96 Å. The N-bonded H atom was refined with free positional
parameters. The H-atom <italic>U</italic><sub>iso</sub> parameters were fixed at 1.3Ueq(C) for
aromatic C—H groups, at 1.3Ueq(N) for the N—H group and at 1.5Ueq(C) for
methyl C—H.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure of title compound showing the atom-numbering scheme. All non-H atoms are represented by 25% probability displacement ellipsoids.</p></caption><graphic xlink:href="e-64-0o205-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>Part of the crystal structure of the title compound showing the chains along [100]. The intermolecular hydrogen bonds are shown as dashed lines.</p></caption><graphic xlink:href="e-64-0o205-fig2"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e157"><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>24</sub>N<sub>2</sub>O<sub>5</sub></td><td rowspan="1" colspan="1"><italic>F</italic><sub>000</sub> = 720</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 336.38</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.203 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Orthorhombic, <italic>P</italic>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub></td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation λ = 0.7107 Å</td></tr><tr><td rowspan="1" colspan="1">Hall symbol: P 2ac 2ab</td><td rowspan="1" colspan="1">Cell parameters from 9649 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 9.9794 (2) Å</td><td rowspan="1" colspan="1">θ = 2.5–25.5º</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.5763 (3) Å</td><td rowspan="1" colspan="1">µ = 0.09 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 16.0720 (4) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 293 (2) K</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1856.71 (8) Å<sup>3</sup></td><td rowspan="1" colspan="1">Prism, colorless</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 4</td><td rowspan="1" colspan="1">0.3 × 0.05 × 0.05 mm</td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e287"><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 area-detector diffractometer</td><td rowspan="1" colspan="1">1559 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> = 0.032</td></tr><tr><td rowspan="1" colspan="1">Monochromator: graphite</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 25.5º</td></tr><tr><td rowspan="1" colspan="1">ω and φ scans</td><td rowspan="1" colspan="1">θ<sub>min</sub> = 2.5º</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: none</td><td rowspan="1" colspan="1"><italic>h</italic> = −11→11</td></tr><tr><td rowspan="1" colspan="1">9649 measured reflections</td><td rowspan="1" colspan="1"><italic>k</italic> = −14→14</td></tr><tr><td rowspan="1" colspan="1">1944 independent reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −19→19</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e380"><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">H atoms treated by a mixture of independent and constrained refinement</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1"> <italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0717<italic>P</italic>)<sup>2</sup> + 0.077<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>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.038</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.044</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.109</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.16 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.03</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.15 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">1944 reflections</td><td rowspan="1" colspan="1">Extinction correction: none</td></tr><tr><td rowspan="1" colspan="1">226 parameters</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e534"><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></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="d1e554"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>x</italic></td><td rowspan="1" colspan="1"><italic>y</italic></td><td rowspan="1" colspan="1"><italic>z</italic></td><td rowspan="1" colspan="1"><italic>U</italic><sub>iso</sub>*/<italic>U</italic><sub>eq</sub></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.5100 (2)</td><td rowspan="1" colspan="1">−0.0209 (2)</td><td rowspan="1" colspan="1">−0.17416 (18)</td><td rowspan="1" colspan="1">0.0659 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.6320 (3)</td><td rowspan="1" colspan="1">0.0439 (4)</td><td rowspan="1" colspan="1">−0.2024 (2)</td><td rowspan="1" colspan="1">0.0978 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2A</td><td rowspan="1" colspan="1">0.6566</td><td rowspan="1" colspan="1">0.0997</td><td rowspan="1" colspan="1">−0.1609</td><td rowspan="1" colspan="1">0.147*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2B</td><td rowspan="1" colspan="1">0.6128</td><td rowspan="1" colspan="1">0.0829</td><td rowspan="1" colspan="1">−0.2538</td><td rowspan="1" colspan="1">0.147*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2C</td><td rowspan="1" colspan="1">0.7046</td><td rowspan="1" colspan="1">−0.0092</td><td rowspan="1" colspan="1">−0.2106</td><td rowspan="1" colspan="1">0.147*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.3937 (3)</td><td rowspan="1" colspan="1">0.0597 (3)</td><td rowspan="1" colspan="1">−0.1641 (3)</td><td rowspan="1" colspan="1">0.1131 (13)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3A</td><td rowspan="1" colspan="1">0.3137</td><td rowspan="1" colspan="1">0.0158</td><td rowspan="1" colspan="1">−0.154</td><td rowspan="1" colspan="1">0.17*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3B</td><td rowspan="1" colspan="1">0.3829</td><td rowspan="1" colspan="1">0.1045</td><td rowspan="1" colspan="1">−0.2139</td><td rowspan="1" colspan="1">0.17*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3C</td><td rowspan="1" colspan="1">0.4099</td><td rowspan="1" colspan="1">0.1104</td><td rowspan="1" colspan="1">−0.1179</td><td rowspan="1" colspan="1">0.17*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.4826 (5)</td><td rowspan="1" colspan="1">−0.1216 (4)</td><td rowspan="1" colspan="1">−0.2302 (2)</td><td rowspan="1" colspan="1">0.1084 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4A</td><td rowspan="1" colspan="1">0.5609</td><td rowspan="1" colspan="1">−0.1695</td><td rowspan="1" colspan="1">−0.2334</td><td rowspan="1" colspan="1">0.163*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4B</td><td rowspan="1" colspan="1">0.4602</td><td rowspan="1" colspan="1">−0.094</td><td rowspan="1" colspan="1">−0.2848</td><td rowspan="1" colspan="1">0.163*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4C</td><td rowspan="1" colspan="1">0.4092</td><td rowspan="1" colspan="1">−0.1657</td><td rowspan="1" colspan="1">−0.2084</td><td rowspan="1" colspan="1">0.163*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.55435 (15)</td><td rowspan="1" colspan="1">−0.06767 (16)</td><td rowspan="1" colspan="1">−0.09296 (11)</td><td rowspan="1" colspan="1">0.0615 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.4705 (2)</td><td rowspan="1" colspan="1">−0.1231 (2)</td><td rowspan="1" colspan="1">−0.04390 (17)</td><td rowspan="1" colspan="1">0.0556 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.35449 (18)</td><td rowspan="1" colspan="1">−0.14394 (19)</td><td rowspan="1" colspan="1">−0.05764 (15)</td><td rowspan="1" colspan="1">0.0834 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.53802 (19)</td><td rowspan="1" colspan="1">−0.15842 (17)</td><td rowspan="1" colspan="1">0.02859 (13)</td><td rowspan="1" colspan="1">0.0533 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.67171 (18)</td><td rowspan="1" colspan="1">−0.12688 (16)</td><td rowspan="1" colspan="1">0.03912 (13)</td><td rowspan="1" colspan="1">0.0493 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.723 (3)</td><td rowspan="1" colspan="1">−0.177 (2)</td><td rowspan="1" colspan="1">0.0211 (18)</td><td rowspan="1" colspan="1">0.064*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.7009 (2)</td><td rowspan="1" colspan="1">−0.0142 (2)</td><td rowspan="1" colspan="1">0.05343 (15)</td><td rowspan="1" colspan="1">0.0501 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.61438 (18)</td><td rowspan="1" colspan="1">0.05698 (16)</td><td rowspan="1" colspan="1">0.06796 (13)</td><td rowspan="1" colspan="1">0.0722 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.8465 (2)</td><td rowspan="1" colspan="1">0.0151 (2)</td><td rowspan="1" colspan="1">0.04796 (15)</td><td rowspan="1" colspan="1">0.0530 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.9465 (2)</td><td rowspan="1" colspan="1">−0.0644 (2)</td><td rowspan="1" colspan="1">0.06302 (17)</td><td rowspan="1" colspan="1">0.0629 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">0.9244</td><td rowspan="1" colspan="1">−0.139</td><td rowspan="1" colspan="1">0.0795</td><td rowspan="1" colspan="1">0.082*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">1.0804 (3)</td><td rowspan="1" colspan="1">−0.0334 (3)</td><td rowspan="1" colspan="1">0.0536 (2)</td><td rowspan="1" colspan="1">0.0855 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">1.1477</td><td rowspan="1" colspan="1">−0.0872</td><td rowspan="1" colspan="1">0.0637</td><td rowspan="1" colspan="1">0.111*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">1.1127 (3)</td><td rowspan="1" colspan="1">0.0761 (4)</td><td rowspan="1" colspan="1">0.0296 (2)</td><td rowspan="1" colspan="1">0.0952 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">1.2022</td><td rowspan="1" colspan="1">0.0965</td><td rowspan="1" colspan="1">0.0232</td><td rowspan="1" colspan="1">0.124*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">1.0149 (4)</td><td rowspan="1" colspan="1">0.1561 (3)</td><td rowspan="1" colspan="1">0.0149 (2)</td><td rowspan="1" colspan="1">0.0937 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">1.0378</td><td rowspan="1" colspan="1">0.2304</td><td rowspan="1" colspan="1">−0.0019</td><td rowspan="1" colspan="1">0.122*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.8811 (3)</td><td rowspan="1" colspan="1">0.1263 (3)</td><td rowspan="1" colspan="1">0.02503 (19)</td><td rowspan="1" colspan="1">0.0735 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.8146</td><td rowspan="1" colspan="1">0.1812</td><td rowspan="1" colspan="1">0.0164</td><td rowspan="1" colspan="1">0.096*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.4706 (2)</td><td rowspan="1" colspan="1">−0.2161 (2)</td><td rowspan="1" colspan="1">0.09331 (16)</td><td rowspan="1" colspan="1">0.0542 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.35904 (18)</td><td rowspan="1" colspan="1">−0.25409 (17)</td><td rowspan="1" colspan="1">0.08502 (12)</td><td rowspan="1" colspan="1">0.0743 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.54681 (15)</td><td rowspan="1" colspan="1">−0.22196 (15)</td><td rowspan="1" colspan="1">0.15998 (11)</td><td rowspan="1" colspan="1">0.0584 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.5017 (3)</td><td rowspan="1" colspan="1">−0.2927 (2)</td><td rowspan="1" colspan="1">0.23280 (17)</td><td rowspan="1" colspan="1">0.0595 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.3708 (3)</td><td rowspan="1" colspan="1">−0.2462 (2)</td><td rowspan="1" colspan="1">0.26688 (19)</td><td rowspan="1" colspan="1">0.0715 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15A</td><td rowspan="1" colspan="1">0.3791</td><td rowspan="1" colspan="1">−0.1646</td><td rowspan="1" colspan="1">0.2764</td><td rowspan="1" colspan="1">0.107*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15B</td><td rowspan="1" colspan="1">0.3502</td><td rowspan="1" colspan="1">−0.2843</td><td rowspan="1" colspan="1">0.3184</td><td rowspan="1" colspan="1">0.107*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15C</td><td rowspan="1" colspan="1">0.3003</td><td rowspan="1" colspan="1">−0.2601</td><td rowspan="1" colspan="1">0.2275</td><td rowspan="1" colspan="1">0.107*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.4944 (3)</td><td rowspan="1" colspan="1">−0.4176 (3)</td><td rowspan="1" colspan="1">0.2060 (2)</td><td rowspan="1" colspan="1">0.0883 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16A</td><td rowspan="1" colspan="1">0.423</td><td rowspan="1" colspan="1">−0.427</td><td rowspan="1" colspan="1">0.1665</td><td rowspan="1" colspan="1">0.132*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16B</td><td rowspan="1" colspan="1">0.4778</td><td rowspan="1" colspan="1">−0.4655</td><td rowspan="1" colspan="1">0.2536</td><td rowspan="1" colspan="1">0.132*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16C</td><td rowspan="1" colspan="1">0.5777</td><td rowspan="1" colspan="1">−0.4396</td><td rowspan="1" colspan="1">0.1807</td><td rowspan="1" colspan="1">0.132*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.6120 (3)</td><td rowspan="1" colspan="1">−0.2720 (4)</td><td rowspan="1" colspan="1">0.2951 (2)</td><td rowspan="1" colspan="1">0.0920 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17A</td><td rowspan="1" colspan="1">0.6962</td><td rowspan="1" colspan="1">−0.2953</td><td rowspan="1" colspan="1">0.2717</td><td rowspan="1" colspan="1">0.138*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17B</td><td rowspan="1" colspan="1">0.5947</td><td rowspan="1" colspan="1">−0.3162</td><td rowspan="1" colspan="1">0.3445</td><td rowspan="1" colspan="1">0.138*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17C</td><td rowspan="1" colspan="1">0.6153</td><td rowspan="1" colspan="1">−0.1914</td><td rowspan="1" colspan="1">0.3089</td><td rowspan="1" colspan="1">0.138*</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="d1e1270"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>U</italic><sup>11</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>22</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>33</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>12</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>13</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>23</sup></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0554 (13)</td><td rowspan="1" colspan="1">0.0720 (17)</td><td rowspan="1" colspan="1">0.0704 (16)</td><td rowspan="1" colspan="1">−0.0016 (12)</td><td rowspan="1" colspan="1">−0.0099 (13)</td><td rowspan="1" colspan="1">0.0087 (14)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.077 (2)</td><td rowspan="1" colspan="1">0.125 (3)</td><td rowspan="1" colspan="1">0.091 (2)</td><td rowspan="1" colspan="1">−0.022 (2)</td><td rowspan="1" colspan="1">−0.0004 (18)</td><td rowspan="1" colspan="1">0.034 (2)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.080 (2)</td><td rowspan="1" colspan="1">0.096 (2)</td><td rowspan="1" colspan="1">0.163 (4)</td><td rowspan="1" colspan="1">0.026 (2)</td><td rowspan="1" colspan="1">0.012 (3)</td><td rowspan="1" colspan="1">0.041 (3)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.137 (3)</td><td rowspan="1" colspan="1">0.108 (3)</td><td rowspan="1" colspan="1">0.080 (2)</td><td rowspan="1" colspan="1">−0.020 (3)</td><td rowspan="1" colspan="1">−0.023 (2)</td><td rowspan="1" colspan="1">−0.010 (2)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0458 (8)</td><td rowspan="1" colspan="1">0.0760 (11)</td><td rowspan="1" colspan="1">0.0626 (10)</td><td rowspan="1" colspan="1">−0.0073 (9)</td><td rowspan="1" colspan="1">−0.0035 (8)</td><td rowspan="1" colspan="1">0.0080 (9)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0431 (13)</td><td rowspan="1" colspan="1">0.0549 (13)</td><td rowspan="1" colspan="1">0.0689 (16)</td><td rowspan="1" colspan="1">−0.0016 (11)</td><td rowspan="1" colspan="1">0.0006 (12)</td><td rowspan="1" colspan="1">0.0000 (12)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0423 (10)</td><td rowspan="1" colspan="1">0.1008 (14)</td><td rowspan="1" colspan="1">0.1071 (16)</td><td rowspan="1" colspan="1">−0.0138 (9)</td><td rowspan="1" colspan="1">−0.0132 (10)</td><td rowspan="1" colspan="1">0.0264 (13)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0362 (10)</td><td rowspan="1" colspan="1">0.0588 (11)</td><td rowspan="1" colspan="1">0.0648 (12)</td><td rowspan="1" colspan="1">−0.0080 (8)</td><td rowspan="1" colspan="1">0.0018 (9)</td><td rowspan="1" colspan="1">0.0017 (10)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0359 (10)</td><td rowspan="1" colspan="1">0.0495 (11)</td><td rowspan="1" colspan="1">0.0626 (12)</td><td rowspan="1" colspan="1">−0.0023 (8)</td><td rowspan="1" colspan="1">0.0041 (9)</td><td rowspan="1" colspan="1">−0.0032 (9)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0476 (13)</td><td rowspan="1" colspan="1">0.0537 (13)</td><td rowspan="1" colspan="1">0.0490 (13)</td><td rowspan="1" colspan="1">−0.0005 (10)</td><td rowspan="1" colspan="1">0.0015 (11)</td><td rowspan="1" colspan="1">−0.0047 (11)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0571 (10)</td><td rowspan="1" colspan="1">0.0634 (10)</td><td rowspan="1" colspan="1">0.0960 (13)</td><td rowspan="1" colspan="1">0.0068 (9)</td><td rowspan="1" colspan="1">0.0060 (9)</td><td rowspan="1" colspan="1">−0.0205 (11)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0470 (12)</td><td rowspan="1" colspan="1">0.0615 (14)</td><td rowspan="1" colspan="1">0.0503 (13)</td><td rowspan="1" colspan="1">−0.0099 (11)</td><td rowspan="1" colspan="1">0.0009 (11)</td><td rowspan="1" colspan="1">−0.0090 (11)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0499 (13)</td><td rowspan="1" colspan="1">0.0681 (15)</td><td rowspan="1" colspan="1">0.0707 (16)</td><td rowspan="1" colspan="1">−0.0058 (13)</td><td rowspan="1" colspan="1">−0.0006 (12)</td><td rowspan="1" colspan="1">−0.0143 (14)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0511 (15)</td><td rowspan="1" colspan="1">0.106 (3)</td><td rowspan="1" colspan="1">0.099 (2)</td><td rowspan="1" colspan="1">−0.0035 (16)</td><td rowspan="1" colspan="1">0.0008 (16)</td><td rowspan="1" colspan="1">−0.032 (2)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0616 (18)</td><td rowspan="1" colspan="1">0.125 (3)</td><td rowspan="1" colspan="1">0.099 (2)</td><td rowspan="1" colspan="1">−0.039 (2)</td><td rowspan="1" colspan="1">0.0132 (18)</td><td rowspan="1" colspan="1">−0.022 (2)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.088 (2)</td><td rowspan="1" colspan="1">0.096 (2)</td><td rowspan="1" colspan="1">0.098 (3)</td><td rowspan="1" colspan="1">−0.042 (2)</td><td rowspan="1" colspan="1">0.0036 (19)</td><td rowspan="1" colspan="1">0.0067 (19)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0696 (17)</td><td rowspan="1" colspan="1">0.0702 (17)</td><td rowspan="1" colspan="1">0.0806 (19)</td><td rowspan="1" colspan="1">−0.0189 (14)</td><td rowspan="1" colspan="1">−0.0040 (15)</td><td rowspan="1" colspan="1">0.0049 (16)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0439 (13)</td><td rowspan="1" colspan="1">0.0551 (13)</td><td rowspan="1" colspan="1">0.0637 (14)</td><td rowspan="1" colspan="1">−0.0060 (11)</td><td rowspan="1" colspan="1">0.0075 (12)</td><td rowspan="1" colspan="1">−0.0056 (12)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0537 (10)</td><td rowspan="1" colspan="1">0.0951 (14)</td><td rowspan="1" colspan="1">0.0740 (12)</td><td rowspan="1" colspan="1">−0.0262 (10)</td><td rowspan="1" colspan="1">0.0028 (9)</td><td rowspan="1" colspan="1">−0.0005 (10)</td></tr><tr><td rowspan="1" colspan="1">O5</td><td rowspan="1" colspan="1">0.0451 (8)</td><td rowspan="1" colspan="1">0.0669 (10)</td><td rowspan="1" colspan="1">0.0632 (10)</td><td rowspan="1" colspan="1">−0.0113 (8)</td><td rowspan="1" colspan="1">0.0039 (8)</td><td rowspan="1" colspan="1">0.0058 (9)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0508 (13)</td><td rowspan="1" colspan="1">0.0568 (15)</td><td rowspan="1" colspan="1">0.0711 (17)</td><td rowspan="1" colspan="1">−0.0038 (11)</td><td rowspan="1" colspan="1">0.0058 (12)</td><td rowspan="1" colspan="1">0.0078 (12)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0632 (16)</td><td rowspan="1" colspan="1">0.0717 (18)</td><td rowspan="1" colspan="1">0.0796 (18)</td><td rowspan="1" colspan="1">0.0039 (14)</td><td rowspan="1" colspan="1">0.0190 (14)</td><td rowspan="1" colspan="1">0.0056 (14)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.092 (2)</td><td rowspan="1" colspan="1">0.0553 (17)</td><td rowspan="1" colspan="1">0.118 (3)</td><td rowspan="1" colspan="1">0.0054 (16)</td><td rowspan="1" colspan="1">0.023 (2)</td><td rowspan="1" colspan="1">0.0053 (16)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0674 (17)</td><td rowspan="1" colspan="1">0.123 (3)</td><td rowspan="1" colspan="1">0.086 (2)</td><td rowspan="1" colspan="1">−0.0129 (19)</td><td rowspan="1" colspan="1">−0.0080 (17)</td><td rowspan="1" colspan="1">0.027 (2)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title><table-wrap position="anchor" id="d1e1753"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">C1—O1</td><td rowspan="1" colspan="1">1.481 (3)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.393 (4)</td></tr><tr><td rowspan="1" colspan="1">C1—C3</td><td rowspan="1" colspan="1">1.498 (4)</td><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C1—C4</td><td rowspan="1" colspan="1">1.498 (5)</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.363 (5)</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.500 (4)</td><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C2—H2A</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.367 (5)</td></tr><tr><td rowspan="1" colspan="1">C2—H2B</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C2—H2C</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.388 (4)</td></tr><tr><td rowspan="1" colspan="1">C3—H3A</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C3—H3B</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C3—H3C</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C13—O4</td><td rowspan="1" colspan="1">1.204 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—H4A</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C13—O5</td><td rowspan="1" colspan="1">1.316 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—H4B</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">O5—C14</td><td rowspan="1" colspan="1">1.498 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—H4C</td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">C14—C17</td><td rowspan="1" colspan="1">1.508 (4)</td></tr><tr><td rowspan="1" colspan="1">O1—C5</td><td rowspan="1" colspan="1">1.317 (3)</td><td rowspan="1" colspan="1">C14—C16</td><td rowspan="1" colspan="1">1.510 (4)</td></tr><tr><td rowspan="1" colspan="1">C5—O2</td><td rowspan="1" colspan="1">1.203 (3)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.515 (4)</td></tr><tr><td rowspan="1" colspan="1">C5—N1</td><td rowspan="1" colspan="1">1.407 (3)</td><td rowspan="1" colspan="1">C15—H15A</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">N1—N2</td><td rowspan="1" colspan="1">1.393 (3)</td><td rowspan="1" colspan="1">C15—H15B</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">N1—C13</td><td rowspan="1" colspan="1">1.407 (3)</td><td rowspan="1" colspan="1">C15—H15C</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">N2—C6</td><td rowspan="1" colspan="1">1.356 (3)</td><td rowspan="1" colspan="1">C16—H16A</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">N2—H2</td><td rowspan="1" colspan="1">0.82 (3)</td><td rowspan="1" colspan="1">C16—H16B</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C6—O3</td><td rowspan="1" colspan="1">1.216 (3)</td><td rowspan="1" colspan="1">C16—H16C</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.495 (3)</td><td rowspan="1" colspan="1">C17—H17A</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.378 (4)</td><td rowspan="1" colspan="1">C17—H17B</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C7—C12</td><td rowspan="1" colspan="1">1.383 (4)</td><td rowspan="1" colspan="1">C17—H17C</td><td rowspan="1" colspan="1">0.96</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">O1—C1—C3</td><td rowspan="1" colspan="1">111.4 (3)</td><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">O1—C1—C4</td><td rowspan="1" colspan="1">107.5 (2)</td><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">119.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C1—C4</td><td rowspan="1" colspan="1">114.0 (3)</td><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">O1—C1—C2</td><td rowspan="1" colspan="1">102.0 (2)</td><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">C3—C1—C2</td><td rowspan="1" colspan="1">110.5 (3)</td><td rowspan="1" colspan="1">C9—C10—C11</td><td rowspan="1" colspan="1">120.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C1—C2</td><td rowspan="1" colspan="1">110.8 (3)</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2A</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">119.8 (3)</td></tr><tr><td rowspan="1" colspan="1">H2A—C2—H2B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">H2A—C2—H2C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C7—C12—C11</td><td rowspan="1" colspan="1">120.2 (3)</td></tr><tr><td rowspan="1" colspan="1">H2B—C2—H2C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C7—C12—H12</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C1—C3—H3A</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C1—C3—H3B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O4—C13—O5</td><td rowspan="1" colspan="1">127.3 (2)</td></tr><tr><td rowspan="1" colspan="1">H3A—C3—H3B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O4—C13—N1</td><td rowspan="1" colspan="1">122.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C3—H3C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O5—C13—N1</td><td rowspan="1" colspan="1">110.47 (18)</td></tr><tr><td rowspan="1" colspan="1">H3A—C3—H3C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C13—O5—C14</td><td rowspan="1" colspan="1">119.39 (17)</td></tr><tr><td rowspan="1" colspan="1">H3B—C3—H3C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O5—C14—C17</td><td rowspan="1" colspan="1">102.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C4—H4A</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O5—C14—C16</td><td rowspan="1" colspan="1">108.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C4—H4B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C17—C14—C16</td><td rowspan="1" colspan="1">112.2 (3)</td></tr><tr><td rowspan="1" colspan="1">H4A—C4—H4B</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">O5—C14—C15</td><td rowspan="1" colspan="1">110.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—C4—H4C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C17—C14—C15</td><td rowspan="1" colspan="1">109.4 (2)</td></tr><tr><td rowspan="1" colspan="1">H4A—C4—H4C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C16—C14—C15</td><td rowspan="1" colspan="1">113.7 (2)</td></tr><tr><td rowspan="1" colspan="1">H4B—C4—H4C</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C14—C15—H15A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—O1—C1</td><td rowspan="1" colspan="1">121.07 (18)</td><td rowspan="1" colspan="1">C14—C15—H15B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O2—C5—O1</td><td rowspan="1" colspan="1">126.8 (3)</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">O2—C5—N1</td><td rowspan="1" colspan="1">123.7 (2)</td><td rowspan="1" colspan="1">C14—C15—H15C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O1—C5—N1</td><td rowspan="1" colspan="1">109.43 (19)</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">N2—N1—C5</td><td rowspan="1" colspan="1">118.9 (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">N2—N1—C13</td><td rowspan="1" colspan="1">119.5 (2)</td><td rowspan="1" colspan="1">C14—C16—H16A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—N1—C13</td><td rowspan="1" colspan="1">121.37 (19)</td><td rowspan="1" colspan="1">C14—C16—H16B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—N2—N1</td><td rowspan="1" colspan="1">118.55 (19)</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">C6—N2—H2</td><td rowspan="1" colspan="1">127.0 (19)</td><td rowspan="1" colspan="1">C14—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N1—N2—H2</td><td rowspan="1" colspan="1">111.5 (19)</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">O3—C6—N2</td><td rowspan="1" colspan="1">122.2 (2)</td><td rowspan="1" colspan="1">H16B—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O3—C6—C7</td><td rowspan="1" colspan="1">123.2 (2)</td><td rowspan="1" colspan="1">C14—C17—H17A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N2—C6—C7</td><td rowspan="1" colspan="1">114.6 (2)</td><td rowspan="1" colspan="1">C14—C17—H17B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C8—C7—C12</td><td rowspan="1" colspan="1">119.1 (2)</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">C8—C7—C6</td><td rowspan="1" colspan="1">122.8 (2)</td><td rowspan="1" colspan="1">C14—C17—H17C</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">118.0 (2)</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">C7—C8—C9</td><td rowspan="1" colspan="1">120.2 (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">C7—C8—H8</td><td rowspan="1" colspan="1">119.9</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">C3—C1—O1—C5</td><td rowspan="1" colspan="1">56.4 (3)</td><td rowspan="1" colspan="1">C12—C7—C8—C9</td><td rowspan="1" colspan="1">−1.3 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—C1—O1—C5</td><td rowspan="1" colspan="1">−69.2 (3)</td><td rowspan="1" colspan="1">C6—C7—C8—C9</td><td rowspan="1" colspan="1">177.3 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—O1—C5</td><td rowspan="1" colspan="1">174.2 (3)</td><td rowspan="1" colspan="1">C7—C8—C9—C10</td><td rowspan="1" colspan="1">0.2 (5)</td></tr><tr><td rowspan="1" colspan="1">C1—O1—C5—O2</td><td rowspan="1" colspan="1">1.2 (4)</td><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">0.2 (5)</td></tr><tr><td rowspan="1" colspan="1">C1—O1—C5—N1</td><td rowspan="1" colspan="1">179.81 (19)</td><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">0.5 (6)</td></tr><tr><td rowspan="1" colspan="1">O2—C5—N1—N2</td><td rowspan="1" colspan="1">−178.3 (2)</td><td rowspan="1" colspan="1">C8—C7—C12—C11</td><td rowspan="1" colspan="1">2.0 (4)</td></tr><tr><td rowspan="1" colspan="1">O1—C5—N1—N2</td><td rowspan="1" colspan="1">3.1 (3)</td><td rowspan="1" colspan="1">C6—C7—C12—C11</td><td rowspan="1" colspan="1">−176.7 (3)</td></tr><tr><td rowspan="1" colspan="1">O2—C5—N1—C13</td><td rowspan="1" colspan="1">−3.7 (4)</td><td rowspan="1" colspan="1">C10—C11—C12—C7</td><td rowspan="1" colspan="1">−1.6 (5)</td></tr><tr><td rowspan="1" colspan="1">O1—C5—N1—C13</td><td rowspan="1" colspan="1">177.6 (2)</td><td rowspan="1" colspan="1">N2—N1—C13—O4</td><td rowspan="1" colspan="1">−173.4 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—N1—N2—C6</td><td rowspan="1" colspan="1">69.7 (3)</td><td rowspan="1" colspan="1">C5—N1—C13—O4</td><td rowspan="1" colspan="1">12.0 (4)</td></tr><tr><td rowspan="1" colspan="1">C13—N1—N2—C6</td><td rowspan="1" colspan="1">−105.0 (3)</td><td rowspan="1" colspan="1">N2—N1—C13—O5</td><td rowspan="1" colspan="1">5.8 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—N2—C6—O3</td><td rowspan="1" colspan="1">9.7 (4)</td><td rowspan="1" colspan="1">C5—N1—C13—O5</td><td rowspan="1" colspan="1">−168.72 (19)</td></tr><tr><td rowspan="1" colspan="1">N1—N2—C6—C7</td><td rowspan="1" colspan="1">−169.0 (2)</td><td rowspan="1" colspan="1">O4—C13—O5—C14</td><td rowspan="1" colspan="1">6.9 (4)</td></tr><tr><td rowspan="1" colspan="1">O3—C6—C7—C8</td><td rowspan="1" colspan="1">154.6 (3)</td><td rowspan="1" colspan="1">N1—C13—O5—C14</td><td rowspan="1" colspan="1">−172.37 (19)</td></tr><tr><td rowspan="1" colspan="1">N2—C6—C7—C8</td><td rowspan="1" colspan="1">−26.7 (4)</td><td rowspan="1" colspan="1">C13—O5—C14—C17</td><td rowspan="1" colspan="1">−177.6 (2)</td></tr><tr><td rowspan="1" colspan="1">O3—C6—C7—C12</td><td rowspan="1" colspan="1">−26.7 (4)</td><td rowspan="1" colspan="1">C13—O5—C14—C16</td><td rowspan="1" colspan="1">63.8 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—C6—C7—C12</td><td rowspan="1" colspan="1">151.9 (2)</td><td rowspan="1" colspan="1">C13—O5—C14—C15</td><td rowspan="1" colspan="1">−61.3 (3)</td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title><table-wrap position="anchor" id="d1e2561"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1"><italic>D</italic>—H···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>—H</td><td rowspan="1" colspan="1">H···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>—H···<italic>A</italic></td></tr><tr><td rowspan="1" colspan="1">N2—H2···O2<sup>i</sup></td><td rowspan="1" colspan="1">0.82 (3)</td><td rowspan="1" colspan="1">2.53 (3)</td><td rowspan="1" colspan="1">3.233 (3)</td><td rowspan="1" colspan="1">145 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—H2···O4<sup>i</sup></td><td rowspan="1" colspan="1">0.82 (3)</td><td rowspan="1" colspan="1">2.32 (3)</td><td rowspan="1" colspan="1">3.062 (3)</td><td rowspan="1" colspan="1">150 (3)</td></tr></table></table-wrap><p>Symmetry codes: (i) <italic>x</italic>+1/2, −<italic>y</italic>−1/2, −<italic>z</italic>.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Allen, F. H. (2002). <italic>Acta Cryst.</italic> B<bold>58</bold>, 380–388.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). <italic>J. Appl. Cryst.</italic><bold>32</bold>, 115–119.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Brosse, N., Pinto, M.-F. & Jamart-Grégoire, B. (2003). <italic>Eur. J. Org. Chem.</italic><bold>24</bold>, 4757–4764.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Farrugia, L. J. (1997). <italic>J. Appl. Cryst.</italic><bold>30</bold>, 565.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Farrugia, L. J. (1999). <italic>J. Appl. Cryst.</italic><bold>32</bold>, 837–838.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Fong, M. C., Gable, R. W. & Schiesser, C. H. (1996). <italic>Acta Cryst.</italic> C<bold>52</bold>, 1886–1889.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Kauffmann, B., Didierjean, C., Brosse, N., Jamart-Grégoire, B. & Aubry, A. (2004). <italic>Acta Cryst.</italic> E<bold>60</bold>, o934–o935.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">MSI (1999). <italic>WebLab ViewerPro 3.5</italic> Molecular Simulation Inc., San Diego, USA.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Nonius (1998). <italic>COLLECT</italic> Nonius BV, Delft, The Netherlands.</mixed-citation></ref><ref id="bb10"><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="bb11"><mixed-citation publication-type="other">Sheldrick, G. M. (1997). <italic>SHELXL97</italic> University of Göttingen, Germany.</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">N2—H2⋯O2<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.82 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.53 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.233 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">145 (3)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N2—H2⋯O4<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.82 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.32 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.062 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">150 (3)</td></tr></tbody></table><table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-64-0o205-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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