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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Methyl <italic>N</italic>-(3-cyanopicolinoyl)-<sc>l</sc>-tryptophanate</title><author><name sortKey="Ovdiichuk, Olga" sort="Ovdiichuk, Olga" uniqKey="Ovdiichuk O" first="Olga" last="Ovdiichuk">Olga Ovdiichuk</name><affiliation><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></nlm:aff></affiliation></author><author><name sortKey="Hordiyenko, Olga" sort="Hordiyenko, Olga" uniqKey="Hordiyenko O" first="Olga" last="Hordiyenko">Olga Hordiyenko</name><affiliation><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></nlm:aff></affiliation></author><author><name sortKey="Voitenko, Zoia" sort="Voitenko, Zoia" uniqKey="Voitenko Z" first="Zoia" last="Voitenko">Zoia Voitenko</name><affiliation><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></nlm:aff></affiliation></author><author><name sortKey="Arrault, Axelle" sort="Arrault, Axelle" uniqKey="Arrault A" first="Axelle" last="Arrault">Axelle Arrault</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoleculaire, UMR 7568, ENSIC, BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Medviediev, Volodymyr" sort="Medviediev, Volodymyr" uniqKey="Medviediev V" first="Volodymyr" last="Medviediev">Volodymyr Medviediev</name><affiliation><nlm:aff id="c">STC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar’kov,<country>Ukraine</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">24454241</idno><idno type="pmc">3885065</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3885065</idno><idno type="RBID">PMC:3885065</idno><idno type="doi">10.1107/S160053681303153X</idno><date when="2013">2013</date><idno type="wicri:Area/Pmc/Corpus">000174</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000174</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Methyl <italic>N</italic>-(3-cyanopicolinoyl)-<sc>l</sc>-tryptophanate</title><author><name sortKey="Ovdiichuk, Olga" sort="Ovdiichuk, Olga" uniqKey="Ovdiichuk O" first="Olga" last="Ovdiichuk">Olga Ovdiichuk</name><affiliation><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></nlm:aff></affiliation></author><author><name sortKey="Hordiyenko, Olga" sort="Hordiyenko, Olga" uniqKey="Hordiyenko O" first="Olga" last="Hordiyenko">Olga Hordiyenko</name><affiliation><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></nlm:aff></affiliation></author><author><name sortKey="Voitenko, Zoia" sort="Voitenko, Zoia" uniqKey="Voitenko Z" first="Zoia" last="Voitenko">Zoia Voitenko</name><affiliation><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></nlm:aff></affiliation></author><author><name sortKey="Arrault, Axelle" sort="Arrault, Axelle" uniqKey="Arrault A" first="Axelle" last="Arrault">Axelle Arrault</name><affiliation><nlm:aff id="b">Laboratoire de Chimie Physique Macromoleculaire, UMR 7568, ENSIC, BP 451, 54001 Nancy,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Medviediev, Volodymyr" sort="Medviediev, Volodymyr" uniqKey="Medviediev V" first="Volodymyr" last="Medviediev">Volodymyr Medviediev</name><affiliation><nlm:aff id="c">STC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar’kov,<country>Ukraine</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="2013">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the title compound, C<sub>19</sub>H<sub>16</sub>N<sub>4</sub>O<sub>3</sub>, the stereocenter has an <sc>l</sc> configuration; <sc>l</sc>-tryptophan methyl ester hydrochloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent molecules are linked <italic>via</italic> N—H⋯O hydrogen bonds, forming chains propagating along the <italic>c</italic>-axis direction.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="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">24454241</article-id><article-id pub-id-type="pmc">3885065</article-id><article-id pub-id-type="publisher-id">su2666</article-id><article-id pub-id-type="doi">10.1107/S160053681303153X</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S160053681303153X</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title>Methyl <italic>N</italic>-(3-cyanopicolinoyl)-<sc>l</sc>-tryptophanate</article-title><alt-title><italic>C<sub>19</sub>H<sub>16</sub>N<sub>4</sub>O<sub>3</sub></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Ovdiichuk</surname><given-names>Olga</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Hordiyenko</surname><given-names>Olga</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Voitenko</surname><given-names>Zoia</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Arrault</surname><given-names>Axelle</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Medviediev</surname><given-names>Volodymyr</given-names></name><xref ref-type="aff" rid="c">c</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country></aff><aff id="b"><label>b</label>Laboratoire de Chimie Physique Macromoleculaire, UMR 7568, ENSIC, BP 451, 54001 Nancy,<country>France</country></aff><aff id="c"><label>c</label>STC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar’kov,<country>Ukraine</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>vmedvedev@xray.isc.kharkov.com</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>12</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>23</day><month>11</month><year>2013</year></pub-date><pub-date pub-type="pmc-release"><day>23</day><month>11</month><year>2013</year></pub-date><volume>69</volume><issue>Pt 12</issue><issue-id pub-id-type="publisher-id">e131200</issue-id><fpage>o1810</fpage><lpage>o1810</lpage><history><date date-type="received"><day>13</day><month>11</month><year>2013</year></date><date date-type="accepted"><day>19</day><month>11</month><year>2013</year></date></history><permissions><copyright-statement>© Ovdiichuk et al. 2013</copyright-statement><copyright-year>2013</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/S160053681303153X">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>In the title compound, C<sub>19</sub>H<sub>16</sub>N<sub>4</sub>O<sub>3</sub>, the stereocenter has an <sc>l</sc> configuration; <sc>l</sc>-tryptophan methyl ester hydrochloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent molecules are linked <italic>via</italic> N—H⋯O hydrogen bonds, forming chains propagating along the <italic>c</italic>-axis direction.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature
</title><p>Cyano-substituted compounds, like the title compound, are useful as intermediates in the synthesis of <italic>N</italic>-hydroxybenzamidines, see: Peterlin-Mašič & Kikelj (2001<xref ref-type="bibr" rid="bb6"> ▶</xref>). For the synthesis of the title compound, see: Devillers <italic>et al.</italic> (2002<xref ref-type="bibr" rid="bb2"> ▶</xref>). For the biological activity of 1,2,4-oxadiazole derivatives, see: Kundu <italic>et al.</italic> (2012<xref ref-type="bibr" rid="bb4"> ▶</xref>); Sakamoto <italic>et al.</italic> (2007<xref ref-type="bibr" rid="bb7"> ▶</xref>); Tyrkov & Sukhenko (2004<xref ref-type="bibr" rid="bb9"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-69-o1810-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" id="l1"><list-item><p>C<sub>19</sub>H<sub>16</sub>N<sub>4</sub>O<sub>3</sub></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 348.36</p></list-item><list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-69-o1810-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 7.473 (2) Å</p></list-item><list-item><p><italic>b</italic> = 11.977 (4) Å</p></list-item><list-item><p><italic>c</italic> = 9.661 (3) Å</p></list-item><list-item><p>β = 91.01 (2)°</p></list-item><list-item><p><italic>V</italic> = 864.6 (4) 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 = 0.09 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 293 K</p></list-item><list-item><p>0.34 × 0.29 × 0.21 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection
</title><p><list list-type="simple" id="l2"><list-item><p>Agilent Xcalibur Sapphire3 diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>CrysAlis PRO</italic>; Agilent, 2011<xref ref-type="bibr" rid="bb1"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.753, <italic>T</italic><sub>max</sub> = 1.000</p></list-item><list-item><p>9857 measured reflections</p></list-item><list-item><p>4832 independent reflections</p></list-item><list-item><p>2596 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.047</p></list-item></list></p></sec><sec id="sec2.1.3"><title>Refinement
</title><p><list list-type="simple" id="l3"><list-item><p><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.051</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.133</p></list-item><list-item><p><italic>S</italic> = 0.93</p></list-item><list-item><p>4832 reflections</p></list-item><list-item><p>236 parameters</p></list-item><list-item><p>1 restraint</p></list-item><list-item><p>H-atom parameters constrained</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.20 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.14 e Å<sup>−3</sup></p></list-item><list-item><p>Absolute structure: Flack parameter determined using 855 quotients [(<italic>I</italic><sup>+</sup>)−(<italic>I</italic><sup>−</sup>)]/[(<italic>I</italic><sup>+</sup>)+(<italic>I</italic><sup>−</sup>)] (Parsons <italic>et al.</italic>, 2013<xref ref-type="bibr" rid="bb5"> ▶</xref>)</p></list-item><list-item><p>Absolute structure parameter: −0.001 (3)</p></list-item></list></p></sec></sec><sec id="d5e482"><title></title><p>Data collection: <italic>CrysAlis PRO</italic> (Agilent, 2011<xref ref-type="bibr" rid="bb1"> ▶</xref>); cell refinement: <italic>CrysAlis PRO</italic>; data reduction: <italic>CrysAlis PRO</italic>; program(s) used to solve structure: <italic>SHELXS2013</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb8"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL2013</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb8"> ▶</xref>); molecular graphics: <italic>OLEX2</italic> (Dolomanov <italic>et al.</italic>, 2009<xref ref-type="bibr" rid="bb3"> ▶</xref>); software used to prepare material for publication: <italic>OLEX2</italic>.</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="loca-data"><p>Crystal structure: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S160053681303153X/su2666sup1.cif">10.1107/S160053681303153X/su2666sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-69-o1810-sup1.cif" xlink:type="simple" id="d35e152" position="anchor"></media></supplementary-material><supplementary-material content-type="loca-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S160053681303153X/su2666Isup2.hkl">10.1107/S160053681303153X/su2666Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-69-o1810-Isup2.hkl" xlink:type="simple" id="d35e159" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-69-o1810-Isup3.cdx"><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/S160053681303153X/su2666Isup3.cdx">10.1107/S160053681303153X/su2666Isup3.cdx</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-69-o1810-Isup4.cml"><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/S160053681303153X/su2666Isup4.cml">10.1107/S160053681303153X/su2666Isup4.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?su2666&file=su2666sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?su2666sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?su2666&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?su2666">SU2666</ext-link>).</p></fn></fn-group><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>1. Comment </title><p>Cyano substituted compounds like the title compound are useful as intermediates
in the synthesis of N-hydroxybenzamidines (Peterlin-Mašič & Kikelj,
2001).
Substituted <italic>N</italic>-hydroxybenzamidines as well as their heterocyclic analogs
are key intermediates in the synthesis of pharmaceutically important
derivatives of 1,2,4-oxadiazole. The latter are well known for their
anticancer (Kundu <italic>et al.</italic>, 2012), anti-HIV (Sakamoto <italic>et
al.</italic>,
2007), and anti-microbial activities (Tyrkov & Sukhenko, 2004).
In our studies
on <italic>N</italic>-hydroxyamidines, of a heterocyclic nature from corresponding cyano
derivatives, we synthesized the title compound and report herein on its
crystal structure.</p><p>The molecular structure of the title compound is illustrated in Fig. 1. The
stereo center, C8, has an <italic>L</italic>-configuration similar to the starting
material <italic>L</italic>-tryptophan methyl ester hydrochloride. The dihedral angle
between the indole ring system (N4/C12-C19; maximum deviation 0.033 (3) Å for
atom C15) and pyridine ring (N1/C1-C4/C6) is 13.55 (14)°.</p><p>In the crystal, adjacent molecules are linked <italic>via</italic> N—H···O hydrogen
bonds, forming chains propagating along the <italic>c</italic> axis direction (Table 1).</p></sec><sec id="experimental"><title>2. Experimental </title><p>The title compound was synthesized according to the literature procedure
(Devillers <italic>et al.</italic>, 2002). 2-Cyanonicotinic acid (5 mmol) was
dissolved
in CH<sub>2</sub>Cl<sub>2</sub> (30 ml), then triethylamine (10 mmol), <italic>L</italic>-tryptophan
methyl ester hydrochloride (5 mmol) and <italic>N</italic>-hydroxybenzotriazole (5 mmol)
were added to the solution. The mixture was stirred at 273 K and EDCI (5.05 mmol; 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydroiodide) was added.
Then, the mixture was stirred at room temperature over night. The residue was
diluted in CH<sub>2</sub>Cl<sub>2</sub>, washed with a solution of 0.1<italic>M</italic> HCl (3 × 15 ml), brine (20 ml) and then dried over MgSO<sub>4</sub> and concentrated under vacuo.
The solid obtained was purified by column chromatography (CH<sub>2</sub>Cl<sub>2</sub>:MeOH
94:6). The title compound is a byproduct and crystallized as pale-yellow
block-like crystals, suitable for X-ray diffraction analysis, by slow
evaporation of a solution in dichloromethane and methanol (9:1).</p></sec><sec id="refinement"><title>3. Refinement </title><p>All H atoms were placed in idealized positions and constrained to ride on their
parent atoms: N-H = 0.86 Å, C-H = 0.93, 0.98, 0.97 and 0.96 Å for
H(aromatic), methine, methylene and methyl H atoms, respectively, with
<italic>U</italic><sub>iso</sub> = 1.5U<sub>eq</sub>(C-methyl) and = 1.2U<sub>eq</sub>(N,C) for other H atoms.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.</p></caption><graphic xlink:href="e-69-o1810-fig1"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e152"><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>19</sub>H<sub>16</sub>N<sub>4</sub>O<sub>3</sub></td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 364</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 348.36</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.338 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>2<sub>1</sub></td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.7107 Å</td></tr><tr><td rowspan="1" colspan="1">Hall symbol: P 2yb</td><td rowspan="1" colspan="1">Cell parameters from 1601 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 7.473 (2) Å</td><td rowspan="1" colspan="1">θ = 3.2–32.1°</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.977 (4) 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> = 9.661 (3) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 293 K</td></tr><tr><td rowspan="1" colspan="1">β = 91.01 (2)°</td><td rowspan="1" colspan="1">Block, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 864.6 (4) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.34 × 0.29 × 0.21 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e275"><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">Agilent Xcalibur Sapphire3 diffractometer</td><td rowspan="1" colspan="1">4832 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: Enhance (Mo) X-ray Source</td><td rowspan="1" colspan="1">2596 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.047</td></tr><tr><td rowspan="1" colspan="1">Detector resolution: 16.1827 pixels mm<sup>-1</sup></td><td rowspan="1" colspan="1">θ<sub>max</sub> = 30.0°, θ<sub>min</sub> = 3.2°</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1"><italic>h</italic> = −10→10</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>CrysAlis PRO</italic>; Agilent, 2011)</td><td rowspan="1" colspan="1"><italic>k</italic> = −16→16</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.753, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>l</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1">9857 measured reflections</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e391"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic><sup>2</sup></td><td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.051</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.133</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0481<italic>P</italic>)<sup>2</sup>]
where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 0.93</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.002</td></tr><tr><td rowspan="1" colspan="1">4832 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.20 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">236 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.14 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">1 restraint</td><td rowspan="1" colspan="1">Absolute structure: Flack parameter determined using 855 quotients
[(<italic>I</italic><sup>+</sup>)-(<italic>I</italic><sup>-</sup>)]/[(<italic>I</italic><sup>+</sup>)+(<italic>I</italic><sup>-</sup>)]
(Parsons <italic>et al.</italic>, 2013)</td></tr><tr><td rowspan="1" colspan="1">64 constraints</td><td rowspan="1" colspan="1">Absolute structure parameter: −0.001 (3)</td></tr><tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e578"><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="d1e595"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>x</italic></td><td rowspan="1" colspan="1"><italic>y</italic></td><td rowspan="1" colspan="1"><italic>z</italic></td><td rowspan="1" colspan="1"><italic>U</italic><sub>iso</sub>*/<italic>U</italic><sub>eq</sub></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.3366 (4)</td><td rowspan="1" colspan="1">0.9180 (2)</td><td rowspan="1" colspan="1">0.4295 (2)</td><td rowspan="1" colspan="1">0.0820 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">−0.0128 (4)</td><td rowspan="1" colspan="1">1.0476 (3)</td><td rowspan="1" colspan="1">0.1272 (4)</td><td rowspan="1" colspan="1">0.0933 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.1275 (3)</td><td rowspan="1" colspan="1">1.2086 (2)</td><td rowspan="1" colspan="1">0.1722 (3)</td><td rowspan="1" colspan="1">0.0744 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.2235 (4)</td><td rowspan="1" colspan="1">0.7036 (2)</td><td rowspan="1" colspan="1">0.1931 (3)</td><td rowspan="1" colspan="1">0.0593 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.4469 (6)</td><td rowspan="1" colspan="1">0.7467 (3)</td><td rowspan="1" colspan="1">0.6623 (4)</td><td rowspan="1" colspan="1">0.0918 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.2808 (4)</td><td rowspan="1" colspan="1">0.9245 (2)</td><td rowspan="1" colspan="1">0.2012 (3)</td><td rowspan="1" colspan="1">0.0588 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.2553</td><td rowspan="1" colspan="1">0.8865</td><td rowspan="1" colspan="1">0.1280</td><td rowspan="1" colspan="1">0.071*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.3014 (4)</td><td rowspan="1" colspan="1">0.9839 (3)</td><td rowspan="1" colspan="1">−0.2741 (3)</td><td rowspan="1" colspan="1">0.0649 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.2870</td><td rowspan="1" colspan="1">0.9343</td><td rowspan="1" colspan="1">−0.3376</td><td rowspan="1" colspan="1">0.078*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.2040 (5)</td><td rowspan="1" colspan="1">0.5917 (3)</td><td rowspan="1" colspan="1">0.1847 (4)</td><td rowspan="1" colspan="1">0.0733 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.1587</td><td rowspan="1" colspan="1">0.5615</td><td rowspan="1" colspan="1">0.1026</td><td rowspan="1" colspan="1">0.088*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.2477 (5)</td><td rowspan="1" colspan="1">0.5201 (3)</td><td rowspan="1" colspan="1">0.2913 (5)</td><td rowspan="1" colspan="1">0.0779 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.2344</td><td rowspan="1" colspan="1">0.4434</td><td rowspan="1" colspan="1">0.2802</td><td rowspan="1" colspan="1">0.094*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.3103 (5)</td><td rowspan="1" colspan="1">0.5626 (4)</td><td rowspan="1" colspan="1">0.4126 (4)</td><td rowspan="1" colspan="1">0.0710 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3A</td><td rowspan="1" colspan="1">0.3404</td><td rowspan="1" colspan="1">0.5156</td><td rowspan="1" colspan="1">0.4860</td><td rowspan="1" colspan="1">0.085*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.3291 (4)</td><td rowspan="1" colspan="1">0.6783 (3)</td><td rowspan="1" colspan="1">0.4258 (3)</td><td rowspan="1" colspan="1">0.0565 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.3958 (5)</td><td rowspan="1" colspan="1">0.7217 (3)</td><td rowspan="1" colspan="1">0.5548 (4)</td><td rowspan="1" colspan="1">0.0692 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.2835 (4)</td><td rowspan="1" colspan="1">0.7458 (3)</td><td rowspan="1" colspan="1">0.3133 (3)</td><td rowspan="1" colspan="1">0.0540 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.3022 (5)</td><td rowspan="1" colspan="1">0.8708 (3)</td><td rowspan="1" colspan="1">0.3205 (3)</td><td rowspan="1" colspan="1">0.0544 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.2987 (4)</td><td rowspan="1" colspan="1">1.0447 (3)</td><td rowspan="1" colspan="1">0.1894 (3)</td><td rowspan="1" colspan="1">0.0534 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">0.3446</td><td rowspan="1" colspan="1">1.0731</td><td rowspan="1" colspan="1">0.2783</td><td rowspan="1" colspan="1">0.064*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.1191 (5)</td><td rowspan="1" colspan="1">1.0983 (3)</td><td rowspan="1" colspan="1">0.1613 (3)</td><td rowspan="1" colspan="1">0.0576 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">−0.0323 (6)</td><td rowspan="1" colspan="1">1.2707 (4)</td><td rowspan="1" colspan="1">0.1397 (6)</td><td rowspan="1" colspan="1">0.0924 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10A</td><td rowspan="1" colspan="1">−0.0786</td><td rowspan="1" colspan="1">1.2479</td><td rowspan="1" colspan="1">0.0508</td><td rowspan="1" colspan="1">0.139*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10B</td><td rowspan="1" colspan="1">−0.0049</td><td rowspan="1" colspan="1">1.3490</td><td rowspan="1" colspan="1">0.1377</td><td rowspan="1" colspan="1">0.139*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10C</td><td rowspan="1" colspan="1">−0.1201</td><td rowspan="1" colspan="1">1.2567</td><td rowspan="1" colspan="1">0.2089</td><td rowspan="1" colspan="1">0.139*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.4336 (5)</td><td rowspan="1" colspan="1">1.0773 (3)</td><td rowspan="1" colspan="1">0.0766 (3)</td><td rowspan="1" colspan="1">0.0611 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11A</td><td rowspan="1" colspan="1">0.4658</td><td rowspan="1" colspan="1">1.1551</td><td rowspan="1" colspan="1">0.0895</td><td rowspan="1" colspan="1">0.073*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11B</td><td rowspan="1" colspan="1">0.5414</td><td rowspan="1" colspan="1">1.0333</td><td rowspan="1" colspan="1">0.0906</td><td rowspan="1" colspan="1">0.073*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.3694 (4)</td><td rowspan="1" colspan="1">1.0617 (3)</td><td rowspan="1" colspan="1">−0.0696 (3)</td><td rowspan="1" colspan="1">0.0555 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.3676 (5)</td><td rowspan="1" colspan="1">0.9647 (3)</td><td rowspan="1" colspan="1">−0.1435 (3)</td><td rowspan="1" colspan="1">0.0628 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.4058</td><td rowspan="1" colspan="1">0.8957</td><td rowspan="1" colspan="1">−0.1100</td><td rowspan="1" colspan="1">0.075*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.2617 (5)</td><td rowspan="1" colspan="1">1.0954 (3)</td><td rowspan="1" colspan="1">−0.2872 (3)</td><td rowspan="1" colspan="1">0.0558 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.3002 (4)</td><td rowspan="1" colspan="1">1.1473 (3)</td><td rowspan="1" colspan="1">−0.1602 (3)</td><td rowspan="1" colspan="1">0.0521 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.2762 (5)</td><td rowspan="1" colspan="1">1.2624 (3)</td><td rowspan="1" colspan="1">−0.1484 (4)</td><td rowspan="1" colspan="1">0.0651 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.3016</td><td rowspan="1" colspan="1">1.2987</td><td rowspan="1" colspan="1">−0.0653</td><td rowspan="1" colspan="1">0.078*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.2146 (6)</td><td rowspan="1" colspan="1">1.3211 (3)</td><td rowspan="1" colspan="1">−0.2616 (5)</td><td rowspan="1" colspan="1">0.0776 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17</td><td rowspan="1" colspan="1">0.1990</td><td rowspan="1" colspan="1">1.3979</td><td rowspan="1" colspan="1">−0.2546</td><td rowspan="1" colspan="1">0.093*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.1748 (5)</td><td rowspan="1" colspan="1">1.2681 (4)</td><td rowspan="1" colspan="1">−0.3863 (5)</td><td rowspan="1" colspan="1">0.0800 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">0.1324</td><td rowspan="1" colspan="1">1.3099</td><td rowspan="1" colspan="1">−0.4610</td><td rowspan="1" colspan="1">0.096*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.1972 (5)</td><td rowspan="1" colspan="1">1.1552 (4)</td><td rowspan="1" colspan="1">−0.4010 (3)</td><td rowspan="1" colspan="1">0.0680 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">0.1701</td><td rowspan="1" colspan="1">1.1197</td><td rowspan="1" colspan="1">−0.4843</td><td rowspan="1" colspan="1">0.082*</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="d1e1175"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>U</italic><sup>11</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>22</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>33</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>12</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>13</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>23</sup></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.138 (2)</td><td rowspan="1" colspan="1">0.0690 (16)</td><td rowspan="1" colspan="1">0.0390 (13)</td><td rowspan="1" colspan="1">0.0108 (16)</td><td rowspan="1" colspan="1">−0.0117 (14)</td><td rowspan="1" colspan="1">−0.0018 (12)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0744 (18)</td><td rowspan="1" colspan="1">0.0795 (19)</td><td rowspan="1" colspan="1">0.125 (3)</td><td rowspan="1" colspan="1">−0.0159 (16)</td><td rowspan="1" colspan="1">−0.0208 (17)</td><td rowspan="1" colspan="1">0.0269 (18)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0749 (18)</td><td rowspan="1" colspan="1">0.0649 (16)</td><td rowspan="1" colspan="1">0.0831 (18)</td><td rowspan="1" colspan="1">0.0101 (13)</td><td rowspan="1" colspan="1">−0.0101 (13)</td><td rowspan="1" colspan="1">−0.0138 (13)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0617 (18)</td><td rowspan="1" colspan="1">0.0628 (18)</td><td rowspan="1" colspan="1">0.0533 (18)</td><td rowspan="1" colspan="1">0.0036 (14)</td><td rowspan="1" colspan="1">−0.0028 (14)</td><td rowspan="1" colspan="1">−0.0073 (14)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.136 (3)</td><td rowspan="1" colspan="1">0.090 (2)</td><td rowspan="1" colspan="1">0.0489 (19)</td><td rowspan="1" colspan="1">0.045 (2)</td><td rowspan="1" colspan="1">−0.0133 (19)</td><td rowspan="1" colspan="1">0.0005 (18)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0815 (19)</td><td rowspan="1" colspan="1">0.0571 (17)</td><td rowspan="1" colspan="1">0.0374 (15)</td><td rowspan="1" colspan="1">−0.0026 (15)</td><td rowspan="1" colspan="1">−0.0072 (13)</td><td rowspan="1" colspan="1">−0.0031 (12)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.088 (2)</td><td rowspan="1" colspan="1">0.0628 (18)</td><td rowspan="1" colspan="1">0.0445 (17)</td><td rowspan="1" colspan="1">−0.0164 (16)</td><td rowspan="1" colspan="1">0.0091 (14)</td><td rowspan="1" colspan="1">−0.0101 (14)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.074 (3)</td><td rowspan="1" colspan="1">0.071 (3)</td><td rowspan="1" colspan="1">0.074 (3)</td><td rowspan="1" colspan="1">−0.003 (2)</td><td rowspan="1" colspan="1">−0.008 (2)</td><td rowspan="1" colspan="1">−0.014 (2)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.075 (3)</td><td rowspan="1" colspan="1">0.060 (2)</td><td rowspan="1" colspan="1">0.099 (4)</td><td rowspan="1" colspan="1">−0.0003 (19)</td><td rowspan="1" colspan="1">−0.003 (2)</td><td rowspan="1" colspan="1">0.002 (2)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.072 (2)</td><td rowspan="1" colspan="1">0.067 (2)</td><td rowspan="1" colspan="1">0.074 (3)</td><td rowspan="1" colspan="1">0.010 (2)</td><td rowspan="1" colspan="1">−0.004 (2)</td><td rowspan="1" colspan="1">0.012 (2)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0557 (19)</td><td rowspan="1" colspan="1">0.063 (2)</td><td rowspan="1" colspan="1">0.051 (2)</td><td rowspan="1" colspan="1">0.0115 (15)</td><td rowspan="1" colspan="1">0.0030 (15)</td><td rowspan="1" colspan="1">0.0044 (16)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.087 (3)</td><td rowspan="1" colspan="1">0.066 (2)</td><td rowspan="1" colspan="1">0.054 (2)</td><td rowspan="1" colspan="1">0.026 (2)</td><td rowspan="1" colspan="1">0.0042 (19)</td><td rowspan="1" colspan="1">0.0076 (19)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0508 (19)</td><td rowspan="1" colspan="1">0.064 (2)</td><td rowspan="1" colspan="1">0.0478 (19)</td><td rowspan="1" colspan="1">0.0073 (16)</td><td rowspan="1" colspan="1">0.0032 (14)</td><td rowspan="1" colspan="1">−0.0031 (16)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.063 (2)</td><td rowspan="1" colspan="1">0.064 (2)</td><td rowspan="1" colspan="1">0.0362 (18)</td><td rowspan="1" colspan="1">0.0110 (16)</td><td rowspan="1" colspan="1">−0.0013 (15)</td><td rowspan="1" colspan="1">0.0013 (15)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.069 (2)</td><td rowspan="1" colspan="1">0.0526 (19)</td><td rowspan="1" colspan="1">0.0380 (16)</td><td rowspan="1" colspan="1">−0.0012 (16)</td><td rowspan="1" colspan="1">−0.0088 (14)</td><td rowspan="1" colspan="1">−0.0014 (15)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.061 (2)</td><td rowspan="1" colspan="1">0.065 (2)</td><td rowspan="1" colspan="1">0.0465 (18)</td><td rowspan="1" colspan="1">−0.0050 (17)</td><td rowspan="1" colspan="1">0.0004 (15)</td><td rowspan="1" colspan="1">0.0072 (16)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.079 (3)</td><td rowspan="1" colspan="1">0.084 (3)</td><td rowspan="1" colspan="1">0.114 (4)</td><td rowspan="1" colspan="1">0.028 (2)</td><td rowspan="1" colspan="1">−0.002 (2)</td><td rowspan="1" colspan="1">−0.002 (3)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.064 (2)</td><td rowspan="1" colspan="1">0.066 (2)</td><td rowspan="1" colspan="1">0.0531 (19)</td><td rowspan="1" colspan="1">−0.0022 (18)</td><td rowspan="1" colspan="1">−0.0010 (15)</td><td rowspan="1" colspan="1">0.0000 (17)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0613 (19)</td><td rowspan="1" colspan="1">0.0580 (19)</td><td rowspan="1" colspan="1">0.0474 (17)</td><td rowspan="1" colspan="1">−0.0095 (17)</td><td rowspan="1" colspan="1">0.0079 (14)</td><td rowspan="1" colspan="1">−0.0039 (16)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.079 (2)</td><td rowspan="1" colspan="1">0.058 (2)</td><td rowspan="1" colspan="1">0.051 (2)</td><td rowspan="1" colspan="1">−0.0090 (18)</td><td rowspan="1" colspan="1">0.0086 (17)</td><td rowspan="1" colspan="1">−0.0012 (17)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.060 (2)</td><td rowspan="1" colspan="1">0.061 (2)</td><td rowspan="1" colspan="1">0.0473 (18)</td><td rowspan="1" colspan="1">−0.0087 (16)</td><td rowspan="1" colspan="1">0.0130 (15)</td><td rowspan="1" colspan="1">0.0006 (16)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0559 (18)</td><td rowspan="1" colspan="1">0.0554 (19)</td><td rowspan="1" colspan="1">0.0454 (17)</td><td rowspan="1" colspan="1">−0.0082 (16)</td><td rowspan="1" colspan="1">0.0117 (14)</td><td rowspan="1" colspan="1">−0.0022 (16)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.073 (2)</td><td rowspan="1" colspan="1">0.061 (2)</td><td rowspan="1" colspan="1">0.062 (2)</td><td rowspan="1" colspan="1">−0.0071 (18)</td><td rowspan="1" colspan="1">0.0122 (18)</td><td rowspan="1" colspan="1">−0.0032 (19)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.080 (3)</td><td rowspan="1" colspan="1">0.067 (2)</td><td rowspan="1" colspan="1">0.087 (3)</td><td rowspan="1" colspan="1">0.003 (2)</td><td rowspan="1" colspan="1">0.021 (2)</td><td rowspan="1" colspan="1">0.005 (2)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.080 (3)</td><td rowspan="1" colspan="1">0.092 (3)</td><td rowspan="1" colspan="1">0.069 (3)</td><td rowspan="1" colspan="1">0.009 (2)</td><td rowspan="1" colspan="1">0.015 (2)</td><td rowspan="1" colspan="1">0.018 (2)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.071 (2)</td><td rowspan="1" colspan="1">0.088 (3)</td><td rowspan="1" colspan="1">0.0456 (19)</td><td rowspan="1" colspan="1">−0.007 (2)</td><td rowspan="1" colspan="1">0.0086 (16)</td><td rowspan="1" colspan="1">0.0029 (19)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1687"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">O1—C7</td><td rowspan="1" colspan="1">1.219 (4)</td><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.9800</td></tr><tr><td rowspan="1" colspan="1">O2—C9</td><td rowspan="1" colspan="1">1.199 (4)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.507 (5)</td></tr><tr><td rowspan="1" colspan="1">O3—C9</td><td rowspan="1" colspan="1">1.327 (4)</td><td rowspan="1" colspan="1">C8—C11</td><td rowspan="1" colspan="1">1.547 (4)</td></tr><tr><td rowspan="1" colspan="1">O3—C10</td><td rowspan="1" colspan="1">1.437 (5)</td><td rowspan="1" colspan="1">C10—H10A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.351 (5)</td><td rowspan="1" colspan="1">C10—H10B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N1—C6</td><td rowspan="1" colspan="1">1.337 (4)</td><td rowspan="1" colspan="1">C10—H10C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N2—C5</td><td rowspan="1" colspan="1">1.141 (5)</td><td rowspan="1" colspan="1">C11—H11A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">N3—H3</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C11—H11B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">N3—C7</td><td rowspan="1" colspan="1">1.327 (4)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.495 (5)</td></tr><tr><td rowspan="1" colspan="1">N3—C8</td><td rowspan="1" colspan="1">1.451 (4)</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.364 (5)</td></tr><tr><td rowspan="1" colspan="1">N4—H4</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C12—C15</td><td rowspan="1" colspan="1">1.438 (5)</td></tr><tr><td rowspan="1" colspan="1">N4—C13</td><td rowspan="1" colspan="1">1.366 (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">N4—C14</td><td rowspan="1" colspan="1">1.374 (5)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.401 (4)</td></tr><tr><td rowspan="1" colspan="1">C1—H1</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C14—C19</td><td rowspan="1" colspan="1">1.391 (5)</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.375 (6)</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.394 (5)</td></tr><tr><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.354 (6)</td><td rowspan="1" colspan="1">C16—C17</td><td rowspan="1" colspan="1">1.372 (6)</td></tr><tr><td rowspan="1" colspan="1">C3—H3A</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C17—H17</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.399 (6)</td><td rowspan="1" colspan="1">C17—C18</td><td rowspan="1" colspan="1">1.389 (6)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.431 (5)</td><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C4—C6</td><td rowspan="1" colspan="1">1.392 (5)</td><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.370 (6)</td></tr><tr><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.505 (5)</td><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.9300</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">C9—O3—C10</td><td rowspan="1" colspan="1">117.4 (3)</td><td rowspan="1" colspan="1">O3—C10—H10A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—N1—C1</td><td rowspan="1" colspan="1">117.5 (3)</td><td rowspan="1" colspan="1">O3—C10—H10B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C7—N3—H3</td><td rowspan="1" colspan="1">118.7</td><td rowspan="1" colspan="1">O3—C10—H10C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C7—N3—C8</td><td rowspan="1" colspan="1">122.7 (3)</td><td rowspan="1" colspan="1">H10A—C10—H10B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C8—N3—H3</td><td rowspan="1" colspan="1">118.7</td><td rowspan="1" colspan="1">H10A—C10—H10C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C13—N4—H4</td><td rowspan="1" colspan="1">125.6</td><td rowspan="1" colspan="1">H10B—C10—H10C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C13—N4—C14</td><td rowspan="1" colspan="1">108.9 (3)</td><td rowspan="1" colspan="1">C8—C11—H11A</td><td rowspan="1" colspan="1">108.4</td></tr><tr><td rowspan="1" colspan="1">C14—N4—H4</td><td rowspan="1" colspan="1">125.6</td><td rowspan="1" colspan="1">C8—C11—H11B</td><td rowspan="1" colspan="1">108.4</td></tr><tr><td rowspan="1" colspan="1">N1—C1—H1</td><td rowspan="1" colspan="1">118.3</td><td rowspan="1" colspan="1">H11A—C11—H11B</td><td rowspan="1" colspan="1">107.4</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">123.4 (4)</td><td rowspan="1" colspan="1">C12—C11—C8</td><td rowspan="1" colspan="1">115.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—H1</td><td rowspan="1" colspan="1">118.3</td><td rowspan="1" colspan="1">C12—C11—H11A</td><td rowspan="1" colspan="1">108.4</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C12—C11—H11B</td><td rowspan="1" colspan="1">108.4</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">119.2 (4)</td><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">126.9 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">C13—C12—C15</td><td rowspan="1" colspan="1">106.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3A</td><td rowspan="1" colspan="1">120.5</td><td rowspan="1" colspan="1">C15—C12—C11</td><td rowspan="1" colspan="1">126.3 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">119.0 (4)</td><td rowspan="1" colspan="1">N4—C13—H13</td><td rowspan="1" colspan="1">125.1</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3A</td><td rowspan="1" colspan="1">120.5</td><td rowspan="1" colspan="1">C12—C13—N4</td><td rowspan="1" colspan="1">109.9 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5</td><td rowspan="1" colspan="1">118.1 (3)</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">125.1</td></tr><tr><td rowspan="1" colspan="1">C6—C4—C3</td><td rowspan="1" colspan="1">118.7 (3)</td><td rowspan="1" colspan="1">N4—C14—C15</td><td rowspan="1" colspan="1">108.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C4—C5</td><td rowspan="1" colspan="1">123.1 (3)</td><td rowspan="1" colspan="1">N4—C14—C19</td><td rowspan="1" colspan="1">130.1 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—C5—C4</td><td rowspan="1" colspan="1">173.8 (4)</td><td rowspan="1" colspan="1">C19—C14—C15</td><td rowspan="1" colspan="1">121.8 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C4</td><td rowspan="1" colspan="1">122.2 (3)</td><td rowspan="1" colspan="1">C14—C15—C12</td><td rowspan="1" colspan="1">106.4 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C7</td><td rowspan="1" colspan="1">116.5 (3)</td><td rowspan="1" colspan="1">C16—C15—C12</td><td rowspan="1" colspan="1">134.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C6—C7</td><td rowspan="1" colspan="1">121.3 (3)</td><td rowspan="1" colspan="1">C16—C15—C14</td><td rowspan="1" colspan="1">119.0 (3)</td></tr><tr><td rowspan="1" colspan="1">O1—C7—N3</td><td rowspan="1" colspan="1">123.1 (3)</td><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">O1—C7—C6</td><td rowspan="1" colspan="1">121.3 (3)</td><td rowspan="1" colspan="1">C17—C16—C15</td><td rowspan="1" colspan="1">118.9 (4)</td></tr><tr><td rowspan="1" colspan="1">N3—C7—C6</td><td rowspan="1" colspan="1">115.6 (3)</td><td rowspan="1" colspan="1">C17—C16—H16</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">N3—C8—H8</td><td rowspan="1" colspan="1">107.9</td><td rowspan="1" colspan="1">C16—C17—H17</td><td rowspan="1" colspan="1">119.3</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C9</td><td rowspan="1" colspan="1">110.7 (3)</td><td rowspan="1" colspan="1">C16—C17—C18</td><td rowspan="1" colspan="1">121.3 (4)</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C11</td><td rowspan="1" colspan="1">111.6 (3)</td><td rowspan="1" colspan="1">C18—C17—H17</td><td rowspan="1" colspan="1">119.3</td></tr><tr><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">107.9</td><td rowspan="1" colspan="1">C17—C18—H18</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C11</td><td rowspan="1" colspan="1">110.8 (3)</td><td rowspan="1" colspan="1">C19—C18—C17</td><td rowspan="1" colspan="1">121.1 (4)</td></tr><tr><td rowspan="1" colspan="1">C11—C8—H8</td><td rowspan="1" colspan="1">107.9</td><td rowspan="1" colspan="1">C19—C18—H18</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">O2—C9—O3</td><td rowspan="1" colspan="1">124.3 (3)</td><td rowspan="1" colspan="1">C14—C19—H19</td><td rowspan="1" colspan="1">121.1</td></tr><tr><td rowspan="1" colspan="1">O2—C9—C8</td><td rowspan="1" colspan="1">124.0 (3)</td><td rowspan="1" colspan="1">C18—C19—C14</td><td rowspan="1" colspan="1">117.8 (4)</td></tr><tr><td rowspan="1" colspan="1">O3—C9—C8</td><td rowspan="1" colspan="1">111.6 (3)</td><td rowspan="1" colspan="1">C18—C19—H19</td><td rowspan="1" colspan="1">121.1</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">N1—C1—C2—C3</td><td rowspan="1" colspan="1">1.4 (6)</td><td rowspan="1" colspan="1">C8—C11—C12—C13</td><td rowspan="1" colspan="1">−81.6 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C7—O1</td><td rowspan="1" colspan="1">171.7 (3)</td><td rowspan="1" colspan="1">C8—C11—C12—C15</td><td rowspan="1" colspan="1">99.6 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C7—N3</td><td rowspan="1" colspan="1">−8.9 (4)</td><td rowspan="1" colspan="1">C9—C8—C11—C12</td><td rowspan="1" colspan="1">−50.2 (4)</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C9—O2</td><td rowspan="1" colspan="1">−13.3 (5)</td><td rowspan="1" colspan="1">C10—O3—C9—O2</td><td rowspan="1" colspan="1">−0.6 (6)</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C9—O3</td><td rowspan="1" colspan="1">169.9 (3)</td><td rowspan="1" colspan="1">C10—O3—C9—C8</td><td rowspan="1" colspan="1">176.3 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C8—C11—C12</td><td rowspan="1" colspan="1">73.6 (4)</td><td rowspan="1" colspan="1">C11—C8—C9—O2</td><td rowspan="1" colspan="1">111.1 (4)</td></tr><tr><td rowspan="1" colspan="1">N4—C14—C15—C12</td><td rowspan="1" colspan="1">1.3 (3)</td><td rowspan="1" colspan="1">C11—C8—C9—O3</td><td rowspan="1" colspan="1">−65.8 (4)</td></tr><tr><td rowspan="1" colspan="1">N4—C14—C15—C16</td><td rowspan="1" colspan="1">178.0 (3)</td><td rowspan="1" colspan="1">C11—C12—C13—N4</td><td rowspan="1" colspan="1">−179.2 (3)</td></tr><tr><td rowspan="1" colspan="1">N4—C14—C19—C18</td><td rowspan="1" colspan="1">−177.9 (3)</td><td rowspan="1" colspan="1">C11—C12—C15—C14</td><td rowspan="1" colspan="1">178.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C6—C4</td><td rowspan="1" colspan="1">1.5 (5)</td><td rowspan="1" colspan="1">C11—C12—C15—C16</td><td rowspan="1" colspan="1">2.4 (6)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C6—C7</td><td rowspan="1" colspan="1">−179.4 (3)</td><td rowspan="1" colspan="1">C12—C15—C16—C17</td><td rowspan="1" colspan="1">176.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.1 (6)</td><td rowspan="1" colspan="1">C13—N4—C14—C15</td><td rowspan="1" colspan="1">−1.4 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">−179.9 (3)</td><td rowspan="1" colspan="1">C13—N4—C14—C19</td><td rowspan="1" colspan="1">177.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C6</td><td rowspan="1" colspan="1">−0.3 (5)</td><td rowspan="1" colspan="1">C13—C12—C15—C14</td><td rowspan="1" colspan="1">−0.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C6—N1</td><td rowspan="1" colspan="1">−0.4 (5)</td><td rowspan="1" colspan="1">C13—C12—C15—C16</td><td rowspan="1" colspan="1">−176.6 (4)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C6—C7</td><td rowspan="1" colspan="1">−179.4 (3)</td><td rowspan="1" colspan="1">C14—N4—C13—C12</td><td rowspan="1" colspan="1">1.0 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—C6—C7—O1</td><td rowspan="1" colspan="1">−9.2 (5)</td><td rowspan="1" colspan="1">C14—C15—C16—C17</td><td rowspan="1" colspan="1">0.4 (5)</td></tr><tr><td rowspan="1" colspan="1">C4—C6—C7—N3</td><td rowspan="1" colspan="1">170.1 (3)</td><td rowspan="1" colspan="1">C15—C12—C13—N4</td><td rowspan="1" colspan="1">−0.2 (4)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C6—N1</td><td rowspan="1" colspan="1">179.2 (3)</td><td rowspan="1" colspan="1">C15—C14—C19—C18</td><td rowspan="1" colspan="1">1.2 (5)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C6—C7</td><td rowspan="1" colspan="1">0.1 (5)</td><td rowspan="1" colspan="1">C15—C16—C17—C18</td><td rowspan="1" colspan="1">0.4 (6)</td></tr><tr><td rowspan="1" colspan="1">C6—N1—C1—C2</td><td rowspan="1" colspan="1">−2.0 (6)</td><td rowspan="1" colspan="1">C16—C17—C18—C19</td><td rowspan="1" colspan="1">−0.5 (6)</td></tr><tr><td rowspan="1" colspan="1">C7—N3—C8—C9</td><td rowspan="1" colspan="1">−109.7 (4)</td><td rowspan="1" colspan="1">C17—C18—C19—C14</td><td rowspan="1" colspan="1">−0.3 (5)</td></tr><tr><td rowspan="1" colspan="1">C7—N3—C8—C11</td><td rowspan="1" colspan="1">126.5 (3)</td><td rowspan="1" colspan="1">C19—C14—C15—C12</td><td rowspan="1" colspan="1">−178.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—N3—C7—O1</td><td rowspan="1" colspan="1">0.8 (6)</td><td rowspan="1" colspan="1">C19—C14—C15—C16</td><td rowspan="1" colspan="1">−1.2 (5)</td></tr><tr><td rowspan="1" colspan="1">C8—N3—C7—C6</td><td rowspan="1" colspan="1">−178.5 (3)</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="d1e2514"><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">N4—H4···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.29</td><td rowspan="1" colspan="1">2.987 (3)</td><td rowspan="1" colspan="1">138</td></tr></table></table-wrap><p>Symmetry code: (i) <italic>x</italic>, <italic>y</italic>, <italic>z</italic>−1.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Agilent (2011). <italic>CrysAlis PRO</italic> Agilent Technologies, Yarton, England.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Devillers, I., Arrault, A., Olive, G. & Marchand-Brynaert, J. (2002). <italic>Tetrahedron Lett.</italic><bold>43</bold>, 3161–3164.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). <italic>J. Appl. Cryst.</italic><bold>42</bold>, 339–341.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Kundu, M., Singh, J., Singh, B., Ghosh, T., Maiti, B. C. & Maity, T. K. (2012). <italic>Indian J. Chem. Sect. B</italic>, <bold>51</bold>, 493–497.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Parsons, S., Flack, H. D. & Wagner, T. (2013). <italic>Acta Cryst.</italic> B<bold>69</bold>, 249–259.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Peterlin-Mašič, L. & Kikelj, D. (2001). <italic>Tetrahedron</italic>, <bold>57</bold>, 7073–7105.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Sakamoto, T., Cullen, M. D., Hartman, T. L., Watson, K. M., Buckheit, R. W., Pannecouque, C., DeClercq, E. & Cushman, M. (2007). <italic>J. Med. Chem.</italic><bold>50</bold>, 3314–3319.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Tyrkov, A. G. & Sukhenko, L. T. (2004). <italic>Pharm. Chem. J.</italic><bold>38</bold>, 30–38.</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">N4—H4⋯O1<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.86</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.29</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.987 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">138</td></tr></tbody></table><table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-69-o1810-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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