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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate</title><author><name sortKey="Ayvazyan, Armen" sort="Ayvazyan, Armen" uniqKey="Ayvazyan A" first="Armen" last="Ayvazyan">Armen Ayvazyan</name><affiliation><nlm:aff id="a">Molecule Structure Research Center of, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences Republic of Armenia, Azatutyan ave. 26, Yerevan 0014,<country>Armenia</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">25484655</idno><idno type="pmc">4257167</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257167</idno><idno type="RBID">PMC:4257167</idno><idno type="doi">10.1107/S1600536814020200</idno><date when="2014">2014</date><idno type="wicri:Area/Pmc/Corpus">000996</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000996</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate</title><author><name sortKey="Ayvazyan, Armen" sort="Ayvazyan, Armen" uniqKey="Ayvazyan A" first="Armen" last="Ayvazyan">Armen Ayvazyan</name><affiliation><nlm:aff id="a">Molecule Structure Research Center of, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences Republic of Armenia, Azatutyan ave. 26, Yerevan 0014,<country>Armenia</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="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><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">25484655</article-id><article-id pub-id-type="pmc">4257167</article-id><article-id pub-id-type="publisher-id">hb7283</article-id><article-id pub-id-type="doi">10.1107/S1600536814020200</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536814020200</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject></subj-group></article-categories><title-group><article-title>Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate</article-title><alt-title><italic>2C<sub>20</sub>H<sub>18</sub>N<sub>6</sub>O<sub>5</sub>·C<sub>3</sub>H<sub>7</sub>NO</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Ayvazyan</surname><given-names>Armen</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Molecule Structure Research Center of, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences Republic of Armenia, Azatutyan ave. 26, Yerevan 0014,<country>Armenia</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>armen@msrc.am</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>10</month><year>2014</year></pub-date><pub-date pub-type="epub"><day>17</day><month>9</month><year>2014</year></pub-date><pub-date pub-type="pmc-release"><day>17</day><month>9</month><year>2014</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>70</volume><issue>Pt 10</issue><issue-id pub-id-type="publisher-id">e141000</issue-id><fpage>213</fpage><lpage>215</lpage><history><date date-type="received"><day>07</day><month>9</month><year>2014</year></date><date date-type="accepted"><day>08</day><month>9</month><year>2014</year></date></history><permissions><copyright-statement>© Armen Ayvazyan 2014</copyright-statement><copyright-year>2014</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/S1600536814020200">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract abstract-type="toc"><p>In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry.</p></abstract><abstract><p>The title compound, C<sub>20</sub>H<sub>18</sub>N<sub>6</sub>O<sub>5</sub>·0.5C<sub>3</sub>H<sub>7</sub>NO, crystallized as a dimethylformamide (DMF) solvate. In the main molecule, the dihedral angle between the pyridodipyrimidine fused-ring system and the benzamide substituent is 82.26 (11)°. In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry. The DMF molecule is disordered about a crystallographic twofold axis and accepts a C—H⋯O interaction from the benzamide molecule.</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>heterocyclic compounds</kwd><kwd>amide</kwd><kwd>hydrogen bonding</kwd><kwd>tetramer</kwd></kwd-group></article-meta></front><body><sec id="sec1"><title>Chemical context </title><p>Compounds containing fused pyrimidine rings show diverse and interesting biological properties. In particular, the representatives of this family show antiviral (Hossain <italic>et al.</italic>, 1997<xref ref-type="bibr" rid="bb9"> ▶</xref>), antibacterial (Sabnis & Rangnekar, 1990<xref ref-type="bibr" rid="bb12"> ▶</xref>), anti-AIDS (Joseph & Burke, 1993<xref ref-type="bibr" rid="bb10"> ▶</xref>) and antinociceptive (Bookser <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb2"> ▶</xref>) activities and may serve as non-nucleoside reverse transcriptase inhibitors as well (De Clercq, 1996<xref ref-type="bibr" rid="bb4"> ▶</xref>). Such a broad spectrum of biological properties for these compounds gives rise to interest in their structures and in this paper the structure of the title solvate, (I)<xref ref-type="chem" rid="scheme1"></xref>, is described.<chem-struct id="scheme1"><graphic xlink:href="e-70-00213-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec id="sec2"><title>Structural commentary </title><p>The molecular structure of the title compound is depicted in Fig. 1<xref ref-type="fig" rid="fig1"> ▶</xref>. The molecule of (I)<xref ref-type="chem" rid="scheme1"></xref> contains two almost planar fragments: (i) pyridodipyrimidine (r.m.s. deviation = 0.046 Å) and (ii) benzamide (r.m.s. deviation = 0.010 Å). The dihedral angle between them is 82.26 (11)°. The dimethyl formamide solvent molecule is disordered about a crystallographic twofold axis.</p></sec><sec id="sec3"><title>Supramolecular features </title><p>Each disordered DMF solvent molecule is connected to an adjacent 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidin-5-yl)benzamide molecule, related by twofold axes, <italic>via</italic> a non-classical C17–H17⋯O51 hydrogen bond (see Fig. 2<xref ref-type="fig" rid="fig2"> ▶</xref> and Table 1<xref ref-type="table" rid="table1"> ▶</xref>). The hydrogen atoms of the amide group are involved in the formation of intermolecular N23–H23<italic>B</italic>⋯O31<sup>i</sup> and N23–H32<italic>A</italic>⋯O22<sup>ii</sup> hydrogen bonds, which link four molecules of the title compound into a four-membered tetramer with an almost square-prismatic shape (see Fig. 3<xref ref-type="fig" rid="fig3"> ▶</xref>). In the extended structure, the interactions between these telomeres have solely van der Waals character. It appears that the almost square-prismatic shape of these tetramers is responsible for the unusual high symmetry of this structure (space group <italic>I</italic><inline-formula><inline-graphic xlink:href="e-70-00213-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>2<italic>d</italic>).</p></sec><sec id="sec4"><title>Database survey </title><p>In the Cambridge Structural Database, just three comparable structures were found: (i) 5-(4-fluorophenyl)-1,3,7,9-tetramethylpyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>]dipyrimidine-2,4,6,8(1<italic>H</italic>,3<italic>H</italic>,7<italic>H</italic>,9<italic>H</italic>)-tetrone (Ghorbani & Bazgir, 2007<xref ref-type="bibr" rid="bb8"> ▶</xref>); (ii) 5-(4-bromophenyl)-1,3,7,9-tetramethylpyrimido[5′,4′:5,6]pyrido[2,3-<italic>d</italic>]pyrimidine-2,4,6,8(1<italic>H</italic>,3<italic>H</italic>,7<italic>H</italic>,9<italic>H</italic>)-tetrone (Dabiri <italic>et al.</italic>, 2007<xref ref-type="bibr" rid="bb3"> ▶</xref>); (iii) 1,3,7,9-tetramethylpyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidine-2,4,6,8-tetrone (Enrique-Miron <italic>et al.</italic>, 1994<xref ref-type="bibr" rid="bb6"> ▶</xref>). The basic fragment for the title compound and compounds (i) and (ii) is the structure of compound (iii), in which the hydrogen atom of the pyridine ring is replaced by benzamide, fluorophenyl and bromophenyl respectively. There are no essential differences in the geometrical characteristics of corresponding chemical bonds, but the crystal packing of the molecules differs essentially because of various features of the intermolecular hydrogen bonding.</p></sec><sec id="sec5"><title>Synthesis and crystallization </title><p>A mixture of 6-amino-1,3-dimethyl-1,2,3,4-tetrahydro-2,4-pyrimidinedione 1.55 g (10 m<italic>M</italic>) and 1,2-benzenedicarbonyl chloride 2.0 g (10 m<italic>M</italic>) dissolved in 10 ml DMFA was stirred under reflux for 2 h. The mixture was concentrated under reduced pressure, then 20 ml of iced water was added to it and filtered. The synthesized compound was dissolved in ethanol and crystallized by slow evaporation at room temperature (m.p. = 627–628 K, 55% yield).</p></sec><sec id="sec6"><title>Refinement </title><p>Crystal data, data collection details and structure refinement details are summarized in Table 2<xref ref-type="table" rid="table2"> ▶</xref>. The solvent molecule of dimethylformamide is disordered about a crystallographic twofold axis. The coordinates of the H atoms of the phenyl ring and methyl groups were determined geometrically and refined using a riding model with the following restraints: for the phenyl ring, C—H = 0.93 Å, <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C), and for the methyl groups, C—H = 0.96 Å, <italic>U</italic><sub>iso</sub>(H) = 1.5<italic>U</italic><sub>eq</sub>(C). Only the coordinates of the H atoms of the amide group, involved in hydrogen bonding, were determined from difference Fourier syntheses and refined freely.</p></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) global, I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536814020200/hb7283sup1.cif">10.1107/S1600536814020200/hb7283sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-70-00213-sup1.cif" xlink:type="simple" id="d35e116" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536814020200/hb7283Isup2.hkl">10.1107/S1600536814020200/hb7283Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-70-00213-Isup2.hkl" xlink:type="simple" id="d35e123" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-70-00213-Isup3.cml"><caption><p>Click here for additional data file.</p></caption></media><p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536814020200/hb7283Isup3.cml">10.1107/S1600536814020200/hb7283Isup3.cml</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>CCDC reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1023362">1023362</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?hb7283&file=hb7283sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?hb7283sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hb7283&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><ack><p>The author acknowledges Dr Tamazyan for helpful discussions and the support from the RA State Committee of Science of the Ministry of Education and Science (grant 13-1D292).</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e36"><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">2C<sub>20</sub>H<sub>18</sub>N<sub>6</sub>O<sub>5</sub>·C<sub>3</sub>H<sub>7</sub>NO</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.432 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 917.90</td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1">Tetragonal, <italic>I</italic>42<italic>d</italic></td><td rowspan="1" colspan="1">Cell parameters from 24 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 26.173 (4) Å</td><td rowspan="1" colspan="1">θ = 12.2–17.3°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.434 (3) Å</td><td rowspan="1" colspan="1">µ = 0.11 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 8517 (3) Å<sup>3</sup></td><td rowspan="1" colspan="1"><italic>T</italic> = 293 K</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 8</td><td rowspan="1" colspan="1">Spherical, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>F</italic>(000) = 3840</td><td rowspan="1" colspan="1">0.16 × 0.16 × 0.16 × 0.16 (radius) mm</td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e160"><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">Enraf–Nonius CAD-4 diffractometer</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.015</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 30.0°, θ<sub>min</sub> = 1.6°</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1"><italic>h</italic> = −26→26</td></tr><tr><td rowspan="1" colspan="1">θ/2θ scans</td><td rowspan="1" colspan="1"><italic>k</italic> = −36→36</td></tr><tr><td rowspan="1" colspan="1">6734 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −17→17</td></tr><tr><td rowspan="1" colspan="1">6216 independent reflections</td><td rowspan="1" colspan="1">1 standard reflections every 60 min</td></tr><tr><td rowspan="1" colspan="1">3247 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e262"><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">Hydrogen site location: mixed</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.056</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0536<italic>P</italic>)<sup>2</sup> + 1.2893<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>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.135</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.006</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.01</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.12 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">6216 reflections</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.17 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">339 parameters</td><td rowspan="1" colspan="1">Absolute structure: Flack <italic>x</italic> determined using 1083 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">1 restraint</td><td rowspan="1" colspan="1">Absolute structure parameter: 0.0 (10)</td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e447"><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="d1e468"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>x</italic></td><td rowspan="1" colspan="1"><italic>y</italic></td><td rowspan="1" colspan="1"><italic>z</italic></td><td rowspan="1" colspan="1"><italic>U</italic><sub>iso</sub>*/<italic>U</italic><sub>eq</sub></td><td rowspan="1" colspan="1">Occ. (<1)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.54916 (10)</td><td rowspan="1" colspan="1">0.33509 (10)</td><td rowspan="1" colspan="1">0.1396 (2)</td><td rowspan="1" colspan="1">0.0533 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.54598 (13)</td><td rowspan="1" colspan="1">0.30369 (12)</td><td rowspan="1" colspan="1">0.0506 (2)</td><td rowspan="1" colspan="1">0.0561 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.49790 (10)</td><td rowspan="1" colspan="1">0.29334 (9)</td><td rowspan="1" colspan="1">0.01248 (19)</td><td rowspan="1" colspan="1">0.0564 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.45404 (12)</td><td rowspan="1" colspan="1">0.31201 (11)</td><td rowspan="1" colspan="1">0.0602 (2)</td><td rowspan="1" colspan="1">0.0491 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.41001 (10)</td><td rowspan="1" colspan="1">0.29570 (9)</td><td rowspan="1" colspan="1">0.01939 (18)</td><td rowspan="1" colspan="1">0.0510 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.36754 (12)</td><td rowspan="1" colspan="1">0.31226 (11)</td><td rowspan="1" colspan="1">0.0642 (2)</td><td rowspan="1" colspan="1">0.0483 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.32283 (10)</td><td rowspan="1" colspan="1">0.29304 (10)</td><td rowspan="1" colspan="1">0.0228 (2)</td><td rowspan="1" colspan="1">0.0572 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.27519 (13)</td><td rowspan="1" colspan="1">0.30566 (13)</td><td rowspan="1" colspan="1">0.0635 (3)</td><td rowspan="1" colspan="1">0.0645 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N9</td><td rowspan="1" colspan="1">0.27443 (10)</td><td rowspan="1" colspan="1">0.33727 (10)</td><td rowspan="1" colspan="1">0.1518 (2)</td><td rowspan="1" colspan="1">0.0596 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.31609 (11)</td><td rowspan="1" colspan="1">0.36475 (13)</td><td rowspan="1" colspan="1">0.1894 (2)</td><td rowspan="1" colspan="1">0.0539 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.36577 (11)</td><td rowspan="1" colspan="1">0.34801 (11)</td><td rowspan="1" colspan="1">0.1489 (2)</td><td rowspan="1" colspan="1">0.0460 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.41230 (11)</td><td rowspan="1" colspan="1">0.36644 (10)</td><td rowspan="1" colspan="1">0.1882 (2)</td><td rowspan="1" colspan="1">0.0434 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.45766 (11)</td><td rowspan="1" colspan="1">0.34605 (10)</td><td rowspan="1" colspan="1">0.1470 (2)</td><td rowspan="1" colspan="1">0.0442 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.50830 (11)</td><td rowspan="1" colspan="1">0.35936 (11)</td><td rowspan="1" colspan="1">0.1884 (2)</td><td rowspan="1" colspan="1">0.0474 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.41236 (10)</td><td rowspan="1" colspan="1">0.40442 (10)</td><td rowspan="1" colspan="1">0.2778 (2)</td><td rowspan="1" colspan="1">0.0414 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.40476 (11)</td><td rowspan="1" colspan="1">0.38612 (11)</td><td rowspan="1" colspan="1">0.3818 (2)</td><td rowspan="1" colspan="1">0.0487 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.4010</td><td rowspan="1" colspan="1">0.3512</td><td rowspan="1" colspan="1">0.3931</td><td rowspan="1" colspan="1">0.058*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.40282 (11)</td><td rowspan="1" colspan="1">0.41874 (12)</td><td rowspan="1" colspan="1">0.4672 (2)</td><td rowspan="1" colspan="1">0.0533 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17</td><td rowspan="1" colspan="1">0.3967</td><td rowspan="1" colspan="1">0.4061</td><td rowspan="1" colspan="1">0.5359</td><td rowspan="1" colspan="1">0.064*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.40994 (14)</td><td rowspan="1" colspan="1">0.47024 (12)</td><td rowspan="1" colspan="1">0.4523 (2)</td><td rowspan="1" colspan="1">0.0620 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">0.4094</td><td rowspan="1" colspan="1">0.4924</td><td rowspan="1" colspan="1">0.5107</td><td rowspan="1" colspan="1">0.074*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.41787 (13)</td><td rowspan="1" colspan="1">0.48880 (11)</td><td rowspan="1" colspan="1">0.3495 (2)</td><td rowspan="1" colspan="1">0.0569 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">0.4227</td><td rowspan="1" colspan="1">0.5237</td><td rowspan="1" colspan="1">0.3395</td><td rowspan="1" colspan="1">0.068*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.41875 (10)</td><td rowspan="1" colspan="1">0.45666 (10)</td><td rowspan="1" colspan="1">0.2610 (2)</td><td rowspan="1" colspan="1">0.0444 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.42413 (11)</td><td rowspan="1" colspan="1">0.47689 (11)</td><td rowspan="1" colspan="1">0.1484 (2)</td><td rowspan="1" colspan="1">0.0497 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O22</td><td rowspan="1" colspan="1">0.41550 (10)</td><td rowspan="1" colspan="1">0.45010 (8)</td><td rowspan="1" colspan="1">0.06982 (15)</td><td rowspan="1" colspan="1">0.0680 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N23</td><td rowspan="1" colspan="1">0.43726 (14)</td><td rowspan="1" colspan="1">0.52520 (11)</td><td rowspan="1" colspan="1">0.1365 (3)</td><td rowspan="1" colspan="1">0.0786 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H23A</td><td rowspan="1" colspan="1">0.4405 (14)</td><td rowspan="1" colspan="1">0.5378 (14)</td><td rowspan="1" colspan="1">0.065 (3)</td><td rowspan="1" colspan="1">0.088 (12)*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H23B</td><td rowspan="1" colspan="1">0.4487 (13)</td><td rowspan="1" colspan="1">0.5433 (12)</td><td rowspan="1" colspan="1">0.191 (2)</td><td rowspan="1" colspan="1">0.069 (10)*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O24</td><td rowspan="1" colspan="1">0.30973 (8)</td><td rowspan="1" colspan="1">0.39919 (10)</td><td rowspan="1" colspan="1">0.2537 (2)</td><td rowspan="1" colspan="1">0.0722 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.22403 (12)</td><td rowspan="1" colspan="1">0.35043 (16)</td><td rowspan="1" colspan="1">0.1963 (3)</td><td rowspan="1" colspan="1">0.0811 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25A</td><td rowspan="1" colspan="1">0.2016</td><td rowspan="1" colspan="1">0.3216</td><td rowspan="1" colspan="1">0.1898</td><td rowspan="1" colspan="1">0.122*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25B</td><td rowspan="1" colspan="1">0.2101</td><td rowspan="1" colspan="1">0.3789</td><td rowspan="1" colspan="1">0.1573</td><td rowspan="1" colspan="1">0.122*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25C</td><td rowspan="1" colspan="1">0.2276</td><td rowspan="1" colspan="1">0.3594</td><td rowspan="1" colspan="1">0.2708</td><td rowspan="1" colspan="1">0.122*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O26</td><td rowspan="1" colspan="1">0.23650 (9)</td><td rowspan="1" colspan="1">0.28828 (12)</td><td rowspan="1" colspan="1">0.0252 (2)</td><td rowspan="1" colspan="1">0.0939 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C27</td><td rowspan="1" colspan="1">0.32474 (15)</td><td rowspan="1" colspan="1">0.25925 (14)</td><td rowspan="1" colspan="1">−0.0717 (3)</td><td rowspan="1" colspan="1">0.0736 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H27A</td><td rowspan="1" colspan="1">0.3295</td><td rowspan="1" colspan="1">0.2794</td><td rowspan="1" colspan="1">−0.1354</td><td rowspan="1" colspan="1">0.110*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H27B</td><td rowspan="1" colspan="1">0.2933</td><td rowspan="1" colspan="1">0.2406</td><td rowspan="1" colspan="1">−0.0772</td><td rowspan="1" colspan="1">0.110*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H27C</td><td rowspan="1" colspan="1">0.3527</td><td rowspan="1" colspan="1">0.2357</td><td rowspan="1" colspan="1">−0.0642</td><td rowspan="1" colspan="1">0.110*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C28</td><td rowspan="1" colspan="1">0.49437 (16)</td><td rowspan="1" colspan="1">0.26283 (14)</td><td rowspan="1" colspan="1">−0.0869 (3)</td><td rowspan="1" colspan="1">0.0777 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H28A</td><td rowspan="1" colspan="1">0.4900</td><td rowspan="1" colspan="1">0.2274</td><td rowspan="1" colspan="1">−0.0688</td><td rowspan="1" colspan="1">0.116*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H28B</td><td rowspan="1" colspan="1">0.5251</td><td rowspan="1" colspan="1">0.2670</td><td rowspan="1" colspan="1">−0.1281</td><td rowspan="1" colspan="1">0.116*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H28C</td><td rowspan="1" colspan="1">0.4657</td><td rowspan="1" colspan="1">0.2742</td><td rowspan="1" colspan="1">−0.1285</td><td rowspan="1" colspan="1">0.116*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O29</td><td rowspan="1" colspan="1">0.58408 (9)</td><td rowspan="1" colspan="1">0.28574 (10)</td><td rowspan="1" colspan="1">0.00875 (19)</td><td rowspan="1" colspan="1">0.0769 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C30</td><td rowspan="1" colspan="1">0.60084 (12)</td><td rowspan="1" colspan="1">0.34458 (14)</td><td rowspan="1" colspan="1">0.1798 (3)</td><td rowspan="1" colspan="1">0.0697 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H30A</td><td rowspan="1" colspan="1">0.6183</td><td rowspan="1" colspan="1">0.3673</td><td rowspan="1" colspan="1">0.1317</td><td rowspan="1" colspan="1">0.105*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H30B</td><td rowspan="1" colspan="1">0.6191</td><td rowspan="1" colspan="1">0.3129</td><td rowspan="1" colspan="1">0.1840</td><td rowspan="1" colspan="1">0.105*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H30C</td><td rowspan="1" colspan="1">0.5990</td><td rowspan="1" colspan="1">0.3598</td><td rowspan="1" colspan="1">0.2499</td><td rowspan="1" colspan="1">0.105*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O31</td><td rowspan="1" colspan="1">0.51616 (7)</td><td rowspan="1" colspan="1">0.38890 (9)</td><td rowspan="1" colspan="1">0.26314 (18)</td><td rowspan="1" colspan="1">0.0603 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N50</td><td rowspan="1" colspan="1">0.44874 (14)</td><td rowspan="1" colspan="1">0.25496 (10)</td><td rowspan="1" colspan="1">0.6322 (12)</td><td rowspan="1" colspan="1">0.0817 (17)</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">O51</td><td rowspan="1" colspan="1">0.4092 (3)</td><td rowspan="1" colspan="1">0.3226 (3)</td><td rowspan="1" colspan="1">0.6400 (9)</td><td rowspan="1" colspan="1">0.180 (4)</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">C52</td><td rowspan="1" colspan="1">0.3997 (5)</td><td rowspan="1" colspan="1">0.2778 (4)</td><td rowspan="1" colspan="1">0.6276 (15)</td><td rowspan="1" colspan="1">0.173 (6)</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H52</td><td rowspan="1" colspan="1">0.3681</td><td rowspan="1" colspan="1">0.2622</td><td rowspan="1" colspan="1">0.6175</td><td rowspan="1" colspan="1">0.208*</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">C53</td><td rowspan="1" colspan="1">0.49626 (16)</td><td rowspan="1" colspan="1">0.2790 (3)</td><td rowspan="1" colspan="1">0.6091 (7)</td><td rowspan="1" colspan="1">0.126 (4)</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H53A</td><td rowspan="1" colspan="1">0.4934</td><td rowspan="1" colspan="1">0.2979</td><td rowspan="1" colspan="1">0.5432</td><td rowspan="1" colspan="1">0.189*</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H53B</td><td rowspan="1" colspan="1">0.5224</td><td rowspan="1" colspan="1">0.2534</td><td rowspan="1" colspan="1">0.6017</td><td rowspan="1" colspan="1">0.189*</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H53C</td><td rowspan="1" colspan="1">0.5051</td><td rowspan="1" colspan="1">0.3018</td><td rowspan="1" colspan="1">0.6666</td><td rowspan="1" colspan="1">0.189*</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">C55</td><td rowspan="1" colspan="1">0.4465 (5)</td><td rowspan="1" colspan="1">0.20136 (14)</td><td rowspan="1" colspan="1">0.6134 (9)</td><td rowspan="1" colspan="1">0.141 (5)</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H55A</td><td rowspan="1" colspan="1">0.4204</td><td rowspan="1" colspan="1">0.1942</td><td rowspan="1" colspan="1">0.5613</td><td rowspan="1" colspan="1">0.211*</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H55B</td><td rowspan="1" colspan="1">0.4387</td><td rowspan="1" colspan="1">0.1840</td><td rowspan="1" colspan="1">0.6795</td><td rowspan="1" colspan="1">0.211*</td><td rowspan="1" colspan="1">0.5</td></tr><tr><td rowspan="1" colspan="1">H55C</td><td rowspan="1" colspan="1">0.4789</td><td rowspan="1" colspan="1">0.1897</td><td rowspan="1" colspan="1">0.5868</td><td rowspan="1" colspan="1">0.211*</td><td rowspan="1" colspan="1">0.5</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">N1</td><td rowspan="1" colspan="1">0.0482 (14)</td><td rowspan="1" colspan="1">0.0619 (15)</td><td rowspan="1" colspan="1">0.0498 (14)</td><td rowspan="1" colspan="1">0.0064 (12)</td><td rowspan="1" colspan="1">0.0030 (12)</td><td rowspan="1" colspan="1">0.0018 (13)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0662 (19)</td><td rowspan="1" colspan="1">0.0569 (18)</td><td rowspan="1" colspan="1">0.0453 (16)</td><td rowspan="1" colspan="1">0.0124 (16)</td><td rowspan="1" colspan="1">0.0074 (16)</td><td rowspan="1" colspan="1">0.0080 (15)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0700 (16)</td><td rowspan="1" colspan="1">0.0575 (14)</td><td rowspan="1" colspan="1">0.0416 (13)</td><td rowspan="1" colspan="1">0.0034 (13)</td><td rowspan="1" colspan="1">0.0066 (14)</td><td rowspan="1" colspan="1">−0.0056 (12)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0633 (18)</td><td rowspan="1" colspan="1">0.0438 (15)</td><td rowspan="1" colspan="1">0.0403 (15)</td><td rowspan="1" colspan="1">0.0031 (14)</td><td rowspan="1" colspan="1">0.0002 (15)</td><td rowspan="1" colspan="1">0.0008 (13)</td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.0650 (15)</td><td rowspan="1" colspan="1">0.0483 (12)</td><td rowspan="1" colspan="1">0.0397 (12)</td><td rowspan="1" colspan="1">−0.0029 (12)</td><td rowspan="1" colspan="1">−0.0055 (13)</td><td rowspan="1" colspan="1">−0.0051 (11)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0606 (18)</td><td rowspan="1" colspan="1">0.0444 (15)</td><td rowspan="1" colspan="1">0.0399 (14)</td><td rowspan="1" colspan="1">−0.0080 (14)</td><td rowspan="1" colspan="1">−0.0108 (14)</td><td rowspan="1" colspan="1">0.0073 (13)</td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.0667 (16)</td><td rowspan="1" colspan="1">0.0580 (15)</td><td rowspan="1" colspan="1">0.0470 (14)</td><td rowspan="1" colspan="1">−0.0150 (13)</td><td rowspan="1" colspan="1">−0.0187 (13)</td><td rowspan="1" colspan="1">0.0022 (13)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.065 (2)</td><td rowspan="1" colspan="1">0.073 (2)</td><td rowspan="1" colspan="1">0.0557 (19)</td><td rowspan="1" colspan="1">−0.0204 (17)</td><td rowspan="1" colspan="1">−0.0157 (17)</td><td rowspan="1" colspan="1">0.0133 (17)</td></tr><tr><td rowspan="1" colspan="1">N9</td><td rowspan="1" colspan="1">0.0501 (14)</td><td rowspan="1" colspan="1">0.0730 (17)</td><td rowspan="1" colspan="1">0.0556 (16)</td><td rowspan="1" colspan="1">−0.0119 (13)</td><td rowspan="1" colspan="1">−0.0073 (13)</td><td rowspan="1" colspan="1">0.0102 (14)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0490 (16)</td><td rowspan="1" colspan="1">0.0661 (19)</td><td rowspan="1" colspan="1">0.0466 (16)</td><td rowspan="1" colspan="1">−0.0066 (15)</td><td rowspan="1" colspan="1">−0.0070 (14)</td><td rowspan="1" colspan="1">0.0078 (16)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0494 (16)</td><td rowspan="1" colspan="1">0.0487 (15)</td><td rowspan="1" colspan="1">0.0400 (15)</td><td rowspan="1" colspan="1">−0.0037 (13)</td><td rowspan="1" colspan="1">−0.0047 (13)</td><td rowspan="1" colspan="1">0.0051 (13)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0491 (14)</td><td rowspan="1" colspan="1">0.0422 (13)</td><td rowspan="1" colspan="1">0.0389 (13)</td><td rowspan="1" colspan="1">−0.0061 (13)</td><td rowspan="1" colspan="1">−0.0013 (13)</td><td rowspan="1" colspan="1">0.0039 (12)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0495 (15)</td><td rowspan="1" colspan="1">0.0412 (14)</td><td rowspan="1" colspan="1">0.0419 (15)</td><td rowspan="1" colspan="1">−0.0025 (13)</td><td rowspan="1" colspan="1">0.0004 (13)</td><td rowspan="1" colspan="1">0.0006 (13)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0473 (15)</td><td rowspan="1" colspan="1">0.0495 (16)</td><td rowspan="1" colspan="1">0.0453 (15)</td><td rowspan="1" colspan="1">−0.0001 (13)</td><td rowspan="1" colspan="1">0.0001 (14)</td><td rowspan="1" colspan="1">0.0056 (13)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0364 (12)</td><td rowspan="1" colspan="1">0.0481 (14)</td><td rowspan="1" colspan="1">0.0398 (13)</td><td rowspan="1" colspan="1">0.0001 (13)</td><td rowspan="1" colspan="1">−0.0021 (12)</td><td rowspan="1" colspan="1">−0.0024 (12)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0491 (16)</td><td rowspan="1" colspan="1">0.0520 (15)</td><td rowspan="1" colspan="1">0.0452 (14)</td><td rowspan="1" colspan="1">−0.0044 (14)</td><td rowspan="1" colspan="1">−0.0024 (14)</td><td rowspan="1" colspan="1">0.0036 (13)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0516 (16)</td><td rowspan="1" colspan="1">0.0709 (19)</td><td rowspan="1" colspan="1">0.0375 (14)</td><td rowspan="1" colspan="1">0.0023 (16)</td><td rowspan="1" colspan="1">−0.0004 (13)</td><td rowspan="1" colspan="1">0.0013 (14)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.084 (2)</td><td rowspan="1" colspan="1">0.0601 (18)</td><td rowspan="1" colspan="1">0.0417 (15)</td><td rowspan="1" colspan="1">0.0050 (18)</td><td rowspan="1" colspan="1">−0.0008 (18)</td><td rowspan="1" colspan="1">−0.0108 (14)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.074 (2)</td><td rowspan="1" colspan="1">0.0454 (16)</td><td rowspan="1" colspan="1">0.0518 (16)</td><td rowspan="1" colspan="1">0.0043 (15)</td><td rowspan="1" colspan="1">−0.0009 (17)</td><td rowspan="1" colspan="1">−0.0045 (14)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.0427 (14)</td><td rowspan="1" colspan="1">0.0495 (15)</td><td rowspan="1" colspan="1">0.0409 (13)</td><td rowspan="1" colspan="1">0.0008 (13)</td><td rowspan="1" colspan="1">−0.0007 (13)</td><td rowspan="1" colspan="1">−0.0028 (13)</td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.0517 (17)</td><td rowspan="1" colspan="1">0.0484 (15)</td><td rowspan="1" colspan="1">0.0491 (17)</td><td rowspan="1" colspan="1">−0.0007 (13)</td><td rowspan="1" colspan="1">0.0010 (14)</td><td rowspan="1" colspan="1">0.0021 (14)</td></tr><tr><td rowspan="1" colspan="1">O22</td><td rowspan="1" colspan="1">0.1034 (17)</td><td rowspan="1" colspan="1">0.0591 (12)</td><td rowspan="1" colspan="1">0.0416 (11)</td><td rowspan="1" colspan="1">−0.0127 (13)</td><td rowspan="1" colspan="1">0.0011 (12)</td><td rowspan="1" colspan="1">−0.0043 (10)</td></tr><tr><td rowspan="1" colspan="1">N23</td><td rowspan="1" colspan="1">0.134 (3)</td><td rowspan="1" colspan="1">0.0529 (16)</td><td rowspan="1" colspan="1">0.0484 (16)</td><td rowspan="1" colspan="1">−0.0154 (17)</td><td rowspan="1" colspan="1">0.0014 (18)</td><td rowspan="1" colspan="1">0.0023 (14)</td></tr><tr><td rowspan="1" colspan="1">O24</td><td rowspan="1" colspan="1">0.0514 (12)</td><td rowspan="1" colspan="1">0.0916 (17)</td><td rowspan="1" colspan="1">0.0736 (15)</td><td rowspan="1" colspan="1">0.0044 (12)</td><td rowspan="1" colspan="1">−0.0026 (12)</td><td rowspan="1" colspan="1">−0.0222 (14)</td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.0446 (18)</td><td rowspan="1" colspan="1">0.118 (3)</td><td rowspan="1" colspan="1">0.080 (3)</td><td rowspan="1" colspan="1">−0.010 (2)</td><td rowspan="1" colspan="1">−0.0022 (18)</td><td rowspan="1" colspan="1">0.006 (2)</td></tr><tr><td rowspan="1" colspan="1">O26</td><td rowspan="1" colspan="1">0.0717 (15)</td><td rowspan="1" colspan="1">0.128 (2)</td><td rowspan="1" colspan="1">0.0816 (17)</td><td rowspan="1" colspan="1">−0.0388 (15)</td><td rowspan="1" colspan="1">−0.0298 (14)</td><td rowspan="1" colspan="1">−0.0001 (17)</td></tr><tr><td rowspan="1" colspan="1">C27</td><td rowspan="1" colspan="1">0.094 (3)</td><td rowspan="1" colspan="1">0.071 (2)</td><td rowspan="1" colspan="1">0.056 (2)</td><td rowspan="1" colspan="1">−0.013 (2)</td><td rowspan="1" colspan="1">−0.0233 (19)</td><td rowspan="1" colspan="1">−0.0092 (18)</td></tr><tr><td rowspan="1" colspan="1">C28</td><td rowspan="1" colspan="1">0.099 (3)</td><td rowspan="1" colspan="1">0.082 (2)</td><td rowspan="1" colspan="1">0.0515 (19)</td><td rowspan="1" colspan="1">0.010 (2)</td><td rowspan="1" colspan="1">0.007 (2)</td><td rowspan="1" colspan="1">−0.0215 (18)</td></tr><tr><td rowspan="1" colspan="1">O29</td><td rowspan="1" colspan="1">0.0739 (14)</td><td rowspan="1" colspan="1">0.0908 (16)</td><td rowspan="1" colspan="1">0.0659 (14)</td><td rowspan="1" colspan="1">0.0232 (14)</td><td rowspan="1" colspan="1">0.0178 (13)</td><td rowspan="1" colspan="1">−0.0051 (13)</td></tr><tr><td rowspan="1" colspan="1">C30</td><td rowspan="1" colspan="1">0.0494 (18)</td><td rowspan="1" colspan="1">0.083 (2)</td><td rowspan="1" colspan="1">0.076 (2)</td><td rowspan="1" colspan="1">0.0070 (16)</td><td rowspan="1" colspan="1">−0.0015 (17)</td><td rowspan="1" colspan="1">−0.003 (2)</td></tr><tr><td rowspan="1" colspan="1">O31</td><td rowspan="1" colspan="1">0.0492 (12)</td><td rowspan="1" colspan="1">0.0676 (13)</td><td rowspan="1" colspan="1">0.0642 (13)</td><td rowspan="1" colspan="1">−0.0020 (10)</td><td rowspan="1" colspan="1">−0.0057 (10)</td><td rowspan="1" colspan="1">−0.0177 (12)</td></tr><tr><td rowspan="1" colspan="1">N50</td><td rowspan="1" colspan="1">0.120 (4)</td><td rowspan="1" colspan="1">0.047 (3)</td><td rowspan="1" colspan="1">0.078 (4)</td><td rowspan="1" colspan="1">0.001 (5)</td><td rowspan="1" colspan="1">−0.009 (8)</td><td rowspan="1" colspan="1">−0.005 (3)</td></tr><tr><td rowspan="1" colspan="1">O51</td><td rowspan="1" colspan="1">0.164 (7)</td><td rowspan="1" colspan="1">0.124 (5)</td><td rowspan="1" colspan="1">0.252 (10)</td><td rowspan="1" colspan="1">0.065 (5)</td><td rowspan="1" colspan="1">0.057 (7)</td><td rowspan="1" colspan="1">0.065 (6)</td></tr><tr><td rowspan="1" colspan="1">C52</td><td rowspan="1" colspan="1">0.126 (9)</td><td rowspan="1" colspan="1">0.101 (7)</td><td rowspan="1" colspan="1">0.291 (17)</td><td rowspan="1" colspan="1">0.034 (7)</td><td rowspan="1" colspan="1">0.034 (11)</td><td rowspan="1" colspan="1">0.057 (10)</td></tr><tr><td rowspan="1" colspan="1">C53</td><td rowspan="1" colspan="1">0.149 (8)</td><td rowspan="1" colspan="1">0.140 (8)</td><td rowspan="1" colspan="1">0.089 (6)</td><td rowspan="1" colspan="1">−0.054 (7)</td><td rowspan="1" colspan="1">−0.002 (7)</td><td rowspan="1" colspan="1">−0.026 (7)</td></tr><tr><td rowspan="1" colspan="1">C55</td><td rowspan="1" colspan="1">0.193 (12)</td><td rowspan="1" colspan="1">0.091 (7)</td><td rowspan="1" colspan="1">0.138 (9)</td><td rowspan="1" colspan="1">−0.033 (8)</td><td rowspan="1" colspan="1">−0.025 (10)</td><td rowspan="1" colspan="1">0.031 (7)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1975"><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">N1—C2</td><td rowspan="1" colspan="1">1.380 (4)</td><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C14</td><td rowspan="1" colspan="1">1.384 (4)</td><td rowspan="1" colspan="1">C19—C20</td><td rowspan="1" colspan="1">1.385 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—C30</td><td rowspan="1" colspan="1">1.463 (4)</td><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C2—O29</td><td rowspan="1" colspan="1">1.219 (4)</td><td rowspan="1" colspan="1">C20—C21</td><td rowspan="1" colspan="1">1.503 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—N3</td><td rowspan="1" colspan="1">1.372 (4)</td><td rowspan="1" colspan="1">C21—O22</td><td rowspan="1" colspan="1">1.224 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C4</td><td rowspan="1" colspan="1">1.382 (4)</td><td rowspan="1" colspan="1">C21—N23</td><td rowspan="1" colspan="1">1.319 (4)</td></tr><tr><td rowspan="1" colspan="1">N3—C28</td><td rowspan="1" colspan="1">1.474 (4)</td><td rowspan="1" colspan="1">N23—H23A</td><td rowspan="1" colspan="1">0.96 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—N5</td><td rowspan="1" colspan="1">1.330 (4)</td><td rowspan="1" colspan="1">N23—H23B</td><td rowspan="1" colspan="1">0.88 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C13</td><td rowspan="1" colspan="1">1.402 (4)</td><td rowspan="1" colspan="1">C25—H25A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N5—C6</td><td rowspan="1" colspan="1">1.317 (4)</td><td rowspan="1" colspan="1">C25—H25B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C6—N7</td><td rowspan="1" colspan="1">1.374 (4)</td><td rowspan="1" colspan="1">C25—H25C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C6—C11</td><td rowspan="1" colspan="1">1.409 (4)</td><td rowspan="1" colspan="1">C27—H27A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N7—C8</td><td rowspan="1" colspan="1">1.386 (4)</td><td rowspan="1" colspan="1">C27—H27B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N7—C27</td><td rowspan="1" colspan="1">1.471 (4)</td><td rowspan="1" colspan="1">C27—H27C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C8—O26</td><td rowspan="1" colspan="1">1.207 (4)</td><td rowspan="1" colspan="1">C28—H28A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C8—N9</td><td rowspan="1" colspan="1">1.375 (4)</td><td rowspan="1" colspan="1">C28—H28B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N9—C10</td><td rowspan="1" colspan="1">1.388 (4)</td><td rowspan="1" colspan="1">C28—H28C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N9—C25</td><td rowspan="1" colspan="1">1.471 (4)</td><td rowspan="1" colspan="1">C30—H30A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C10—O24</td><td rowspan="1" colspan="1">1.216 (4)</td><td rowspan="1" colspan="1">C30—H30B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.462 (4)</td><td rowspan="1" colspan="1">C30—H30C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.398 (4)</td><td rowspan="1" colspan="1">N50—C52</td><td rowspan="1" colspan="1">1.417 (13)</td></tr><tr><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.399 (4)</td><td rowspan="1" colspan="1">N50—C53</td><td rowspan="1" colspan="1">1.423 (5)</td></tr><tr><td rowspan="1" colspan="1">C12—C15</td><td rowspan="1" colspan="1">1.493 (4)</td><td rowspan="1" colspan="1">N50—C55</td><td rowspan="1" colspan="1">1.423 (5)</td></tr><tr><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.464 (4)</td><td rowspan="1" colspan="1">O51—C52</td><td rowspan="1" colspan="1">1.207 (14)</td></tr><tr><td rowspan="1" colspan="1">O31—C14</td><td rowspan="1" colspan="1">1.226 (3)</td><td rowspan="1" colspan="1">C52—H52</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.393 (4)</td><td rowspan="1" colspan="1">C53—H53A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C15—C20</td><td rowspan="1" colspan="1">1.393 (4)</td><td rowspan="1" colspan="1">C53—H53B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C16—C17</td><td rowspan="1" colspan="1">1.364 (4)</td><td rowspan="1" colspan="1">C53—H53C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C55—H55A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C17—C18</td><td rowspan="1" colspan="1">1.373 (4)</td><td rowspan="1" colspan="1">C55—H55B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C17—H17</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C55—H55C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.383 (4)</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">C2—N1—C14</td><td rowspan="1" colspan="1">125.3 (3)</td><td rowspan="1" colspan="1">C18—C19—H19</td><td rowspan="1" colspan="1">119.2</td></tr><tr><td rowspan="1" colspan="1">C2—N1—C30</td><td rowspan="1" colspan="1">115.5 (3)</td><td rowspan="1" colspan="1">C20—C19—H19</td><td rowspan="1" colspan="1">119.2</td></tr><tr><td rowspan="1" colspan="1">C14—N1—C30</td><td rowspan="1" colspan="1">119.1 (3)</td><td rowspan="1" colspan="1">C19—C20—C15</td><td rowspan="1" colspan="1">118.3 (3)</td></tr><tr><td rowspan="1" colspan="1">O29—C2—N3</td><td rowspan="1" colspan="1">121.8 (3)</td><td rowspan="1" colspan="1">C19—C20—C21</td><td rowspan="1" colspan="1">121.8 (3)</td></tr><tr><td rowspan="1" colspan="1">O29—C2—N1</td><td rowspan="1" colspan="1">121.5 (3)</td><td rowspan="1" colspan="1">C15—C20—C21</td><td rowspan="1" colspan="1">119.8 (2)</td></tr><tr><td rowspan="1" colspan="1">N3—C2—N1</td><td rowspan="1" colspan="1">116.7 (3)</td><td rowspan="1" colspan="1">O22—C21—N23</td><td rowspan="1" colspan="1">120.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—N3—C4</td><td rowspan="1" colspan="1">122.9 (3)</td><td rowspan="1" colspan="1">O22—C21—C20</td><td rowspan="1" colspan="1">121.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—N3—C28</td><td rowspan="1" colspan="1">117.0 (3)</td><td rowspan="1" colspan="1">N23—C21—C20</td><td rowspan="1" colspan="1">117.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—N3—C28</td><td rowspan="1" colspan="1">120.0 (3)</td><td rowspan="1" colspan="1">C21—N23—H23A</td><td rowspan="1" colspan="1">117 (2)</td></tr><tr><td rowspan="1" colspan="1">N5—C4—N3</td><td rowspan="1" colspan="1">116.2 (3)</td><td rowspan="1" colspan="1">C21—N23—H23B</td><td rowspan="1" colspan="1">121 (2)</td></tr><tr><td rowspan="1" colspan="1">N5—C4—C13</td><td rowspan="1" colspan="1">123.8 (3)</td><td rowspan="1" colspan="1">H23A—N23—H23B</td><td rowspan="1" colspan="1">120 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C4—C13</td><td rowspan="1" colspan="1">119.9 (3)</td><td rowspan="1" colspan="1">N9—C25—H25A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—N5—C4</td><td rowspan="1" colspan="1">117.6 (2)</td><td rowspan="1" colspan="1">N9—C25—H25B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N5—C6—N7</td><td rowspan="1" colspan="1">116.1 (3)</td><td rowspan="1" colspan="1">H25A—C25—H25B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N5—C6—C11</td><td rowspan="1" colspan="1">124.2 (3)</td><td rowspan="1" colspan="1">N9—C25—H25C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N7—C6—C11</td><td rowspan="1" colspan="1">119.7 (3)</td><td rowspan="1" colspan="1">H25A—C25—H25C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—N7—C8</td><td rowspan="1" colspan="1">122.8 (3)</td><td rowspan="1" colspan="1">H25B—C25—H25C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—N7—C27</td><td rowspan="1" colspan="1">119.4 (3)</td><td rowspan="1" colspan="1">N7—C27—H27A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C8—N7—C27</td><td rowspan="1" colspan="1">117.7 (3)</td><td rowspan="1" colspan="1">N7—C27—H27B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O26—C8—N9</td><td rowspan="1" colspan="1">121.9 (3)</td><td rowspan="1" colspan="1">H27A—C27—H27B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O26—C8—N7</td><td rowspan="1" colspan="1">121.4 (3)</td><td rowspan="1" colspan="1">N7—C27—H27C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N9—C8—N7</td><td rowspan="1" colspan="1">116.6 (3)</td><td rowspan="1" colspan="1">H27A—C27—H27C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C8—N9—C10</td><td rowspan="1" colspan="1">124.7 (3)</td><td rowspan="1" colspan="1">H27B—C27—H27C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C8—N9—C25</td><td rowspan="1" colspan="1">117.0 (3)</td><td rowspan="1" colspan="1">N3—C28—H28A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C10—N9—C25</td><td rowspan="1" colspan="1">117.1 (3)</td><td rowspan="1" colspan="1">N3—C28—H28B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O24—C10—N9</td><td rowspan="1" colspan="1">119.9 (3)</td><td rowspan="1" colspan="1">H28A—C28—H28B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O24—C10—C11</td><td rowspan="1" colspan="1">124.8 (3)</td><td rowspan="1" colspan="1">N3—C28—H28C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N9—C10—C11</td><td rowspan="1" colspan="1">115.3 (3)</td><td rowspan="1" colspan="1">H28A—C28—H28C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C6</td><td rowspan="1" colspan="1">117.5 (3)</td><td rowspan="1" colspan="1">H28B—C28—H28C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C10</td><td rowspan="1" colspan="1">123.4 (3)</td><td rowspan="1" colspan="1">N1—C30—H30A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—C11—C10</td><td rowspan="1" colspan="1">119.1 (3)</td><td rowspan="1" colspan="1">N1—C30—H30B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">118.6 (2)</td><td rowspan="1" colspan="1">H30A—C30—H30B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C15</td><td rowspan="1" colspan="1">119.5 (3)</td><td rowspan="1" colspan="1">N1—C30—H30C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C13—C12—C15</td><td rowspan="1" colspan="1">121.8 (3)</td><td rowspan="1" colspan="1">H30A—C30—H30C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C13—C4</td><td rowspan="1" colspan="1">117.8 (3)</td><td rowspan="1" colspan="1">H30B—C30—H30C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C13—C14</td><td rowspan="1" colspan="1">123.3 (3)</td><td rowspan="1" colspan="1">C52—N50—C53</td><td rowspan="1" colspan="1">126.6 (7)</td></tr><tr><td rowspan="1" colspan="1">C4—C13—C14</td><td rowspan="1" colspan="1">118.9 (3)</td><td rowspan="1" colspan="1">C52—N50—C55</td><td rowspan="1" colspan="1">111.9 (9)</td></tr><tr><td rowspan="1" colspan="1">O31—C14—N1</td><td rowspan="1" colspan="1">119.5 (3)</td><td rowspan="1" colspan="1">C53—N50—C55</td><td rowspan="1" colspan="1">116.0 (8)</td></tr><tr><td rowspan="1" colspan="1">O31—C14—C13</td><td rowspan="1" colspan="1">124.7 (3)</td><td rowspan="1" colspan="1">O51—C52—N50</td><td rowspan="1" colspan="1">102.6 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C14—C13</td><td rowspan="1" colspan="1">115.8 (3)</td><td rowspan="1" colspan="1">O51—C52—H52</td><td rowspan="1" colspan="1">128.7</td></tr><tr><td rowspan="1" colspan="1">C16—C15—C20</td><td rowspan="1" colspan="1">119.6 (2)</td><td rowspan="1" colspan="1">N50—C52—H52</td><td rowspan="1" colspan="1">128.7</td></tr><tr><td rowspan="1" colspan="1">C16—C15—C12</td><td rowspan="1" colspan="1">117.6 (2)</td><td rowspan="1" colspan="1">N50—C53—H53A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C20—C15—C12</td><td rowspan="1" colspan="1">122.8 (2)</td><td rowspan="1" colspan="1">N50—C53—H53B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C17—C16—C15</td><td rowspan="1" colspan="1">120.9 (3)</td><td rowspan="1" colspan="1">H53A—C53—H53B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C17—C16—H16</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">N50—C53—H53C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">H53A—C53—H53C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C16—C17—C18</td><td rowspan="1" colspan="1">120.3 (3)</td><td rowspan="1" colspan="1">H53B—C53—H53C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C16—C17—H17</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">N50—C55—H55A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C18—C17—H17</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">N50—C55—H55B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C17—C18—C19</td><td rowspan="1" colspan="1">119.3 (3)</td><td rowspan="1" colspan="1">H55A—C55—H55B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C17—C18—H18</td><td rowspan="1" colspan="1">120.3</td><td rowspan="1" colspan="1">N50—C55—H55C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C19—C18—H18</td><td rowspan="1" colspan="1">120.3</td><td rowspan="1" colspan="1">H55A—C55—H55C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C18—C19—C20</td><td rowspan="1" colspan="1">121.6 (3)</td><td rowspan="1" colspan="1">H55B—C55—H55C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14—N1—C2—O29</td><td rowspan="1" colspan="1">176.2 (3)</td><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">177.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C30—N1—C2—O29</td><td rowspan="1" colspan="1">−0.6 (4)</td><td rowspan="1" colspan="1">C6—C11—C12—C15</td><td rowspan="1" colspan="1">180.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C14—N1—C2—N3</td><td rowspan="1" colspan="1">−4.4 (4)</td><td rowspan="1" colspan="1">C10—C11—C12—C15</td><td rowspan="1" colspan="1">1.3 (4)</td></tr><tr><td rowspan="1" colspan="1">C30—N1—C2—N3</td><td rowspan="1" colspan="1">178.8 (3)</td><td rowspan="1" colspan="1">C11—C12—C13—C4</td><td rowspan="1" colspan="1">6.6 (4)</td></tr><tr><td rowspan="1" colspan="1">O29—C2—N3—C4</td><td rowspan="1" colspan="1">178.1 (3)</td><td rowspan="1" colspan="1">C15—C12—C13—C4</td><td rowspan="1" colspan="1">−177.8 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—N3—C4</td><td rowspan="1" colspan="1">−1.3 (4)</td><td rowspan="1" colspan="1">C11—C12—C13—C14</td><td rowspan="1" colspan="1">−174.8 (3)</td></tr><tr><td rowspan="1" colspan="1">O29—C2—N3—C28</td><td rowspan="1" colspan="1">−4.8 (4)</td><td rowspan="1" colspan="1">C15—C12—C13—C14</td><td rowspan="1" colspan="1">0.9 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—N3—C28</td><td rowspan="1" colspan="1">175.8 (3)</td><td rowspan="1" colspan="1">N5—C4—C13—C12</td><td rowspan="1" colspan="1">−4.2 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—N3—C4—N5</td><td rowspan="1" colspan="1">−175.1 (3)</td><td rowspan="1" colspan="1">N3—C4—C13—C12</td><td rowspan="1" colspan="1">176.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C28—N3—C4—N5</td><td rowspan="1" colspan="1">7.9 (4)</td><td rowspan="1" colspan="1">N5—C4—C13—C14</td><td rowspan="1" colspan="1">177.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—N3—C4—C13</td><td rowspan="1" colspan="1">4.7 (4)</td><td rowspan="1" colspan="1">N3—C4—C13—C14</td><td rowspan="1" colspan="1">−2.7 (4)</td></tr><tr><td rowspan="1" colspan="1">C28—N3—C4—C13</td><td rowspan="1" colspan="1">−172.3 (3)</td><td rowspan="1" colspan="1">C2—N1—C14—O31</td><td rowspan="1" colspan="1">−175.5 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C4—N5—C6</td><td rowspan="1" colspan="1">179.1 (3)</td><td rowspan="1" colspan="1">C30—N1—C14—O31</td><td rowspan="1" colspan="1">1.2 (4)</td></tr><tr><td rowspan="1" colspan="1">C13—C4—N5—C6</td><td rowspan="1" colspan="1">−0.7 (4)</td><td rowspan="1" colspan="1">C2—N1—C14—C13</td><td rowspan="1" colspan="1">6.1 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—N5—C6—N7</td><td rowspan="1" colspan="1">−177.5 (3)</td><td rowspan="1" colspan="1">C30—N1—C14—C13</td><td rowspan="1" colspan="1">−177.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—N5—C6—C11</td><td rowspan="1" colspan="1">3.3 (4)</td><td rowspan="1" colspan="1">C12—C13—C14—O31</td><td rowspan="1" colspan="1">0.7 (5)</td></tr><tr><td rowspan="1" colspan="1">N5—C6—N7—C8</td><td rowspan="1" colspan="1">178.1 (3)</td><td rowspan="1" colspan="1">C4—C13—C14—O31</td><td rowspan="1" colspan="1">179.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C11—C6—N7—C8</td><td rowspan="1" colspan="1">−2.7 (4)</td><td rowspan="1" colspan="1">C12—C13—C14—N1</td><td rowspan="1" colspan="1">179.0 (3)</td></tr><tr><td rowspan="1" colspan="1">N5—C6—N7—C27</td><td rowspan="1" colspan="1">−4.6 (4)</td><td rowspan="1" colspan="1">C4—C13—C14—N1</td><td rowspan="1" colspan="1">−2.3 (4)</td></tr><tr><td rowspan="1" colspan="1">C11—C6—N7—C27</td><td rowspan="1" colspan="1">174.7 (3)</td><td rowspan="1" colspan="1">C11—C12—C15—C16</td><td rowspan="1" colspan="1">79.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—N7—C8—O26</td><td rowspan="1" colspan="1">179.8 (3)</td><td rowspan="1" colspan="1">C13—C12—C15—C16</td><td rowspan="1" colspan="1">−96.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C27—N7—C8—O26</td><td rowspan="1" colspan="1">2.4 (5)</td><td rowspan="1" colspan="1">C11—C12—C15—C20</td><td rowspan="1" colspan="1">−99.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—N7—C8—N9</td><td rowspan="1" colspan="1">−2.6 (4)</td><td rowspan="1" colspan="1">C13—C12—C15—C20</td><td rowspan="1" colspan="1">84.6 (4)</td></tr><tr><td rowspan="1" colspan="1">C27—N7—C8—N9</td><td rowspan="1" colspan="1">180.0 (3)</td><td rowspan="1" colspan="1">C20—C15—C16—C17</td><td rowspan="1" colspan="1">0.9 (4)</td></tr><tr><td rowspan="1" colspan="1">O26—C8—N9—C10</td><td rowspan="1" colspan="1">−169.4 (3)</td><td rowspan="1" colspan="1">C12—C15—C16—C17</td><td rowspan="1" colspan="1">−178.0 (3)</td></tr><tr><td rowspan="1" colspan="1">N7—C8—N9—C10</td><td rowspan="1" colspan="1">13.0 (5)</td><td rowspan="1" colspan="1">C15—C16—C17—C18</td><td rowspan="1" colspan="1">−2.0 (5)</td></tr><tr><td rowspan="1" colspan="1">O26—C8—N9—C25</td><td rowspan="1" colspan="1">−1.8 (5)</td><td rowspan="1" colspan="1">C16—C17—C18—C19</td><td rowspan="1" colspan="1">1.5 (5)</td></tr><tr><td rowspan="1" colspan="1">N7—C8—N9—C25</td><td rowspan="1" colspan="1">−179.4 (3)</td><td rowspan="1" colspan="1">C17—C18—C19—C20</td><td rowspan="1" colspan="1">0.1 (5)</td></tr><tr><td rowspan="1" colspan="1">C8—N9—C10—O24</td><td rowspan="1" colspan="1">165.2 (3)</td><td rowspan="1" colspan="1">C18—C19—C20—C15</td><td rowspan="1" colspan="1">−1.2 (5)</td></tr><tr><td rowspan="1" colspan="1">C25—N9—C10—O24</td><td rowspan="1" colspan="1">−2.4 (4)</td><td rowspan="1" colspan="1">C18—C19—C20—C21</td><td rowspan="1" colspan="1">176.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—N9—C10—C11</td><td rowspan="1" colspan="1">−16.6 (4)</td><td rowspan="1" colspan="1">C16—C15—C20—C19</td><td rowspan="1" colspan="1">0.7 (4)</td></tr><tr><td rowspan="1" colspan="1">C25—N9—C10—C11</td><td rowspan="1" colspan="1">175.8 (3)</td><td rowspan="1" colspan="1">C12—C15—C20—C19</td><td rowspan="1" colspan="1">179.6 (3)</td></tr><tr><td rowspan="1" colspan="1">N5—C6—C11—C12</td><td rowspan="1" colspan="1">−0.8 (4)</td><td rowspan="1" colspan="1">C16—C15—C20—C21</td><td rowspan="1" colspan="1">−176.7 (3)</td></tr><tr><td rowspan="1" colspan="1">N7—C6—C11—C12</td><td rowspan="1" colspan="1">−180.0 (3)</td><td rowspan="1" colspan="1">C12—C15—C20—C21</td><td rowspan="1" colspan="1">2.1 (4)</td></tr><tr><td rowspan="1" colspan="1">N5—C6—C11—C10</td><td rowspan="1" colspan="1">177.9 (3)</td><td rowspan="1" colspan="1">C19—C20—C21—O22</td><td rowspan="1" colspan="1">−166.2 (3)</td></tr><tr><td rowspan="1" colspan="1">N7—C6—C11—C10</td><td rowspan="1" colspan="1">−1.3 (4)</td><td rowspan="1" colspan="1">C15—C20—C21—O22</td><td rowspan="1" colspan="1">11.1 (4)</td></tr><tr><td rowspan="1" colspan="1">O24—C10—C11—C12</td><td rowspan="1" colspan="1">6.9 (5)</td><td rowspan="1" colspan="1">C19—C20—C21—N23</td><td rowspan="1" colspan="1">12.0 (4)</td></tr><tr><td rowspan="1" colspan="1">N9—C10—C11—C12</td><td rowspan="1" colspan="1">−171.3 (3)</td><td rowspan="1" colspan="1">C15—C20—C21—N23</td><td rowspan="1" colspan="1">−170.6 (3)</td></tr><tr><td rowspan="1" colspan="1">O24—C10—C11—C6</td><td rowspan="1" colspan="1">−171.7 (3)</td><td rowspan="1" colspan="1">C53—N50—C52—O51</td><td rowspan="1" colspan="1">−25 (2)</td></tr><tr><td rowspan="1" colspan="1">N9—C10—C11—C6</td><td rowspan="1" colspan="1">10.1 (4)</td><td rowspan="1" colspan="1">C55—N50—C52—O51</td><td rowspan="1" colspan="1">−176.9 (13)</td></tr><tr><td rowspan="1" colspan="1">C6—C11—C12—C13</td><td rowspan="1" colspan="1">−4.3 (4)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e3220"><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">N23—H23<italic>B</italic>···O31<sup>i</sup></td><td rowspan="1" colspan="1">0.88 (3)</td><td rowspan="1" colspan="1">2.19 (3)</td><td rowspan="1" colspan="1">3.003 (4)</td><td rowspan="1" colspan="1">153 (3)</td></tr><tr><td rowspan="1" colspan="1">N23—H23<italic>A</italic>···O22<sup>ii</sup></td><td rowspan="1" colspan="1">0.96 (4)</td><td rowspan="1" colspan="1">2.09 (4)</td><td rowspan="1" colspan="1">3.017 (4)</td><td rowspan="1" colspan="1">164 (3)</td></tr><tr><td rowspan="1" colspan="1">C17—H17···O51</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.56</td><td rowspan="1" colspan="1">3.313 (10)</td><td rowspan="1" colspan="1">138</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+1, −<italic>y</italic>+1, <italic>z</italic>; (ii) <italic>y</italic>, −<italic>x</italic>+1, −<italic>z</italic>.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). <italic>J. Appl. Cryst.</italic><bold>37</bold>, 335–338.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Bookser, B. C., Ugarkar, B. G., Matelich, M. C., Lemus, R. H., Alla, M., Tsuchiya, M., Nakane, M., Nagahisa, A., Wiesner, J. B. & Erion, M. D. (2005). <italic>J. Med. Chem.</italic><bold>48</bold>, 7808–7820.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Dabiri, M., Arvin-Nezhad, H., Khavasi, H. R. & Bazgir, A. (2007). <italic>Tetrahedron</italic>, <bold>63</bold>, 1770–1774.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">De Clercq, E. (1996). <italic>Rev. Med. Virol.</italic><bold>6</bold>, 97–117.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Enraf–Nonius (1988). <italic>CAD-4 Software</italic> Enraf–Nonius, Delft, The Netherlands.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Enrique-Miron, C., Quiros-Olozabal, M., Romero-Molina, M. A., Salas-Peregrin, J. M., Sanchez-Sanchez, M. P., Hueso-Urena, F., Moreno-Carretero, M. N. & Martin-Ramos, J. D. (1994). <italic>J. Chem. Crystallogr.</italic><bold>24</bold>, 465–468.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Ghorbani, H. & Bazgir, A. (2007). <italic>Acta Cryst.</italic> E<bold>63</bold>, o2790.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Hossain, N., Rozenski, J., De Clercq, E. & Herdewijn, P. (1997). <italic>J. Org. Chem.</italic><bold>62</bold>, 2442–2447.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Joseph, S. & Burke, J. M. (1993). <italic>J. Biol. Chem.</italic><bold>268</bold>, 24515–24518.</mixed-citation></ref><ref id="bb11"><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="bb12"><mixed-citation publication-type="other">Sabnis, R. W. & Rangnekar, D. W. (1990). <italic>Indian J. Technol.</italic><bold>28</bold>, 54–58.</mixed-citation></ref><ref id="bb13"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb14"><mixed-citation publication-type="other">Spek, A. L. (1997). <italic>HELENA</italic> University of Utrecht, The Netherlands.</mixed-citation></ref><ref id="bb15"><mixed-citation publication-type="other">Westrip, S. P. (2010). <italic>J. Appl. Cryst.</italic><bold>43</bold>, 920–925.</mixed-citation></ref></ref-list></back><floats-group><fig id="fig1" position="float"><label>Figure 1</label><caption><p>The molecular structure with thermal displacement ellipsoids drawn at the 50% probability level (H atoms omitted for clarity).</p></caption><graphic xlink:href="e-70-00213-fig1"></graphic></fig><fig id="fig2" position="float"><label>Figure 2</label><caption><p>Non-classical hydrogen bonding of disordered DMFA solvent molecules with molecules of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidin-5-yl)benzamide related by the twofold axes of the space group.</p></caption><graphic xlink:href="e-70-00213-fig2"></graphic></fig><fig id="fig3" position="float"><label>Figure 3</label><caption><p>Square-prismatic telomer formed by four 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>:6,5-<italic>d</italic>′]dipyrimidin-5-yl)<0.02pt>benzamide molecules <italic>via</italic> intermolecular hydrogen bonding.</p></caption><graphic xlink:href="e-70-00213-fig3"></graphic></fig><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">N23—H23<italic>B</italic>⋯O31<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.88 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.19 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.003 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">153 (3)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N23—H23<italic>A</italic>⋯O22<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.96 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.09 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.017 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">164 (3)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C17—H17⋯O51</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.56</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.313 (10)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">138</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-70-00213-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-70-00213-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap><table-wrap id="table2" position="float"><label>Table 2</label><caption><title>Experimental details</title></caption><table frame="hsides" rules="groups"><tbody valign="top"><tr><td style="" rowspan="1" colspan="2" align="left" valign="top">Crystal data</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2C<sub>20</sub>H<sub>18</sub>N<sub>6</sub>O<sub>5</sub>·C<sub>3</sub>H<sub>7</sub>NO</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic><sub>r</sub></td><td style="" rowspan="1" colspan="1" align="left" valign="top">917.90</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td><td style="" rowspan="1" colspan="1" align="left" valign="top">Tetragonal, <italic>I</italic><inline-formula><inline-graphic xlink:href="e-70-00213-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>2<italic>d</italic></td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">293</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>, <italic>c</italic> (Å)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">26.173 (4), 12.434 (3)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic> (Å<sup>3</sup>)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">8517 (3)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic></td><td style="" rowspan="1" colspan="1" align="left" valign="top">8</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Radiation type</td><td style="" rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>α</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.11</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.16 (radius)</td></tr><tr><td style="" rowspan="1" colspan="2" align="left" valign="top"> </td></tr><tr><td style="" rowspan="1" colspan="2" align="left" valign="top">Data collection</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td><td style="" rowspan="1" colspan="1" align="left" valign="top">Enraf–Nonius CAD-4</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic> > 2σ(<italic>I</italic>)] reflections</td><td style="" rowspan="1" colspan="1" align="left" valign="top">6734, 6216, 3247</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic><sub>int</sub></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.015</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub> (Å<sup>−1</sup>)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.703</td></tr><tr><td style="" rowspan="1" colspan="2" align="left" valign="top"> </td></tr><tr><td style="" rowspan="1" colspan="2" align="left" valign="top">Refinement</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)], <italic>wR</italic>(<italic>F</italic><sup>2</sup>), <italic>S</italic></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.056, 0.135, 1.01</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td><td style="" rowspan="1" colspan="1" align="left" valign="top">6216</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td><td style="" rowspan="1" colspan="1" align="left" valign="top">339</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of restraints</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td><td style="" rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>−3</sup>)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.12, −0.17</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Absolute structure</td><td style="" rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic> determined using 1083 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="bb11"> ▶</xref>)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Absolute structure parameter</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.0 (10)</td></tr></tbody></table><table-wrap-foot><p>Computer programs: <italic>CAD-4 Software</italic> (Enraf–Nonius, 1988<xref ref-type="bibr" rid="bb5"> ▶</xref>), <italic>HELENA</italic> (Spek, 1997<xref ref-type="bibr" rid="bb14"> ▶</xref>), <italic>SHELXS2014</italic> and <italic>SHELXL2014</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb13"> ▶</xref>), <italic>ORTEP-3 for Windows</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb7"> ▶</xref>), <italic>enCIFer</italic> (Allen <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb1"> ▶</xref>) and <italic>publCIF</italic> (Westrip, 2010<xref ref-type="bibr" rid="bb15"> ▶</xref>).</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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