Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate
Identifieur interne : 000980 ( Pmc/Corpus ); précédent : 000979; suivant : 000981Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate
Auteurs : Muthaiah Jeevaraj ; Palaniyappan Sivajeyanthi ; Bellarmin Edison ; Kaliyaperumal Thanigaimani ; Kasthuri Balasubramani ; Ibrahim Abdul RazakSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2017.
Abstract
Tetrameric associations of two cations and two anions occur, being linked by N—H⋯O hydrogen bonds.
Url:
DOI: 10.1107/S2056989017011252
PubMed: 28932461
PubMed Central: 5588567
Links to Exploration step
PMC:5588567Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate</title><author><name sortKey="Jeevaraj, Muthaiah" sort="Jeevaraj, Muthaiah" uniqKey="Jeevaraj M" first="Muthaiah" last="Jeevaraj">Muthaiah Jeevaraj</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Sivajeyanthi, Palaniyappan" sort="Sivajeyanthi, Palaniyappan" uniqKey="Sivajeyanthi P" first="Palaniyappan" last="Sivajeyanthi">Palaniyappan Sivajeyanthi</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Edison, Bellarmin" sort="Edison, Bellarmin" uniqKey="Edison B" first="Bellarmin" last="Edison">Bellarmin Edison</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Thanigaimani, Kaliyaperumal" sort="Thanigaimani, Kaliyaperumal" uniqKey="Thanigaimani K" first="Kaliyaperumal" last="Thanigaimani">Kaliyaperumal Thanigaimani</name><affiliation><nlm:aff id="b">Department of Chemistry, Government Arts College, Tiruchirappalli 620 022, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Balasubramani, Kasthuri" sort="Balasubramani, Kasthuri" uniqKey="Balasubramani K" first="Kasthuri" last="Balasubramani">Kasthuri Balasubramani</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Razak, Ibrahim Abdul" sort="Razak, Ibrahim Abdul" uniqKey="Razak I" first="Ibrahim Abdul" last="Razak">Ibrahim Abdul Razak</name><affiliation><nlm:aff id="c">School of Physics, Universiti Sains Malaysia, 11800 USM, Penang,<country>Malaysia</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">28932461</idno><idno type="pmc">5588567</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5588567</idno><idno type="RBID">PMC:5588567</idno><idno type="doi">10.1107/S2056989017011252</idno><date when="2017">2017</date><idno type="wicri:Area/Pmc/Corpus">000980</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000980</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate</title><author><name sortKey="Jeevaraj, Muthaiah" sort="Jeevaraj, Muthaiah" uniqKey="Jeevaraj M" first="Muthaiah" last="Jeevaraj">Muthaiah Jeevaraj</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Sivajeyanthi, Palaniyappan" sort="Sivajeyanthi, Palaniyappan" uniqKey="Sivajeyanthi P" first="Palaniyappan" last="Sivajeyanthi">Palaniyappan Sivajeyanthi</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Edison, Bellarmin" sort="Edison, Bellarmin" uniqKey="Edison B" first="Bellarmin" last="Edison">Bellarmin Edison</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Thanigaimani, Kaliyaperumal" sort="Thanigaimani, Kaliyaperumal" uniqKey="Thanigaimani K" first="Kaliyaperumal" last="Thanigaimani">Kaliyaperumal Thanigaimani</name><affiliation><nlm:aff id="b">Department of Chemistry, Government Arts College, Tiruchirappalli 620 022, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Balasubramani, Kasthuri" sort="Balasubramani, Kasthuri" uniqKey="Balasubramani K" first="Kasthuri" last="Balasubramani">Kasthuri Balasubramani</name><affiliation><nlm:aff id="a">Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Razak, Ibrahim Abdul" sort="Razak, Ibrahim Abdul" uniqKey="Razak I" first="Ibrahim Abdul" last="Razak">Ibrahim Abdul Razak</name><affiliation><nlm:aff id="c">School of Physics, Universiti Sains Malaysia, 11800 USM, Penang,<country>Malaysia</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title><idno type="eISSN">2056-9890</idno><imprint><date when="2017">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Tetrameric associations of two cations and two anions occur, being linked by N—H⋯O hydrogen bonds.</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><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 E Crystallogr Commun</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr E Crystallogr Commun</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Crystallographic Communications</journal-title></journal-title-group><issn pub-type="epub">2056-9890</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">28932461</article-id><article-id pub-id-type="pmc">5588567</article-id><article-id pub-id-type="publisher-id">hb7693</article-id><article-id pub-id-type="doi">10.1107/S2056989017011252</article-id><article-id pub-id-type="coden">ACSECI</article-id><article-id pub-id-type="pii">S2056989017011252</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject></subj-group></article-categories><title-group><article-title>Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate</article-title><alt-title><italic>C<sub>6</sub>H<sub>10</sub>N<sub>3</sub>O<sup>+</sup>·C<sub>7</sub>H<sub>5</sub>O<sub>3</sub><sup>−</sup></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Jeevaraj</surname><given-names>Muthaiah</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Sivajeyanthi</surname><given-names>Palaniyappan</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Edison</surname><given-names>Bellarmin</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Thanigaimani</surname><given-names>Kaliyaperumal</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Balasubramani</surname><given-names>Kasthuri</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Razak</surname><given-names>Ibrahim Abdul</given-names></name><xref ref-type="aff" rid="c">c</xref><xref ref-type="author-notes" rid="aunote1">‡</xref></contrib><aff id="a"><label>a</label>Department of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu,<country>India</country></aff><aff id="b"><label>b</label>Department of Chemistry, Government Arts College, Tiruchirappalli 620 022, Tamil Nadu,<country>India</country></aff><aff id="c"><label>c</label>School of Physics, Universiti Sains Malaysia, 11800 USM, Penang,<country>Malaysia</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>manavaibala@gmail.com</email></corresp><fn id="aunote1"><label>‡</label><p>Thomson Reuters ResearcherID: A-5599-2009.</p></fn></author-notes><pub-date pub-type="collection"><day>01</day><month>9</month><year>2017</year></pub-date><pub-date pub-type="epub"><day>08</day><month>8</month><year>2017</year></pub-date><pub-date pub-type="pmc-release"><day>08</day><month>8</month><year>2017</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>73</volume><issue>Pt 9</issue><issue-id pub-id-type="publisher-id">e170900</issue-id><fpage>1305</fpage><lpage>1307</lpage><history><date date-type="received"><day>17</day><month>7</month><year>2017</year></date><date date-type="accepted"><day>31</day><month>7</month><year>2017</year></date></history><permissions><copyright-statement>© Jeevaraj et al. 2017</copyright-statement><copyright-year>2017</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 (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p><ali:license_ref>http://creativecommons.org/licenses/by/2.0/uk/</ali:license_ref></license></permissions><self-uri xlink:href="https://doi.org/10.1107/S2056989017011252">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract abstract-type="toc"><p>Tetrameric associations of two cations and two anions occur, being linked by N—H⋯O hydrogen bonds.</p></abstract><abstract><p>In the title molecular salt, C<sub>6</sub>H<sub>10</sub>N<sub>3</sub>O<sup>+</sup>·C<sub>7</sub>H<sub>5</sub>O<sub>3</sub><sup>−</sup>, the cation is protonated at the N atom lying between the amine and methyl substituents and the dihedral angle between the carboxyl group and its attached ring in the anion is 4.0 (2)°. The anion features an intramolecular O—H⋯O hydrogen bond, which closes an <italic>S</italic>(6) ring. The cation and anion are linked by two N—H⋯O hydrogen bonds [<italic>R</italic><sub>2</sub><sup>2</sup>(8) motif] to generate an ion pair in which the dihedral angle between the aromatic rings is 8.34 (9)°. Crystal symmetry relates two ion pairs bridged by further N—H⋯O hydrogen bonds into a tetrameric <italic>DDAA</italic> array. The tetramers are linked by pairs of C—H⋯O hydrogen bonds to generate [100] chains. Hirshfeld surface and fingerprint plot analyses are presented.</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>Hirshfeld surface analysis</kwd><kwd>hydrogen bonding</kwd></kwd-group><funding-group><award-group><funding-source>Department of Science and Technology (DST-SERB)</funding-source><award-id>SB/FT/CS-058/2013</award-id><principal-award-recipient>PS</principal-award-recipient><principal-award-recipient>KB</principal-award-recipient></award-group><funding-statement>This work was funded by <funding-source>Department of Science and Technology (DST-SERB)</funding-source> grant <award-id>SB/FT/CS-058/2013</award-id> to PS and KB. </funding-statement></funding-group></article-meta></front><body><sec id="sec1"><title>chemical context </title><p>Pyrimidine and aminopyrimidine derivatives have many applications as pesticides and pharmaceutical agents (Condon <italic>et al.</italic>, 1993<xref ref-type="bibr" rid="bb3"> ▸</xref>). For example, imazosulfuron, ethirmol and mepanipyrim have been commercialized as agrochemicals (Maeno <italic>et al.</italic>, 1990<xref ref-type="bibr" rid="bb11"> ▸</xref>). Pyrimidine derivatives have also been developed as antiviral agents, such as AZT, which is the most widely-used anti-AIDS drug (Gilchrist, 1997<xref ref-type="bibr" rid="bb5"> ▸</xref>). Hydrogen bonding plays a vital role in molecular recognition. Supramolecular chemistry plays a pivotal role in biological systems and in artificial systems. It refers to the specific interaction between two or more motifs through non-covalent interactions such as hydrogen bonding, hydrophobic forces, van der Waals forces, π–π interactions <italic>etc</italic>. The generating of supramolecular architectures is correlated to the positions and properties of the active groups in molecules (Desiraju <italic>et al.</italic>, 1989<xref ref-type="bibr" rid="bb4"> ▸</xref>; Steiner <italic>et al.</italic>, 2002<xref ref-type="bibr" rid="bb17"> ▸</xref>) As part of our studies in these areas, the synthesis and structure of the title molecular salt, (I)<xref ref-type="chem" rid="scheme1"></xref>, is presented here.<chem-struct id="scheme1"><graphic xlink:href="e-73-01305-scheme1.jpg" position="float" orientation="portrait"></graphic></chem-struct></p></sec><sec id="sec2"><title>structural commentary </title><p>The molecular structure of (I)<xref ref-type="chem" rid="scheme1"></xref> is shown in Fig. 1<xref ref-type="fig" rid="fig1"> ▸</xref>. The asymmetric unit contains a 2-amino-4-methoxy-6-methylpyrimidinium cation and a 2-hydroxybenzoate anion. The cation is protonated at N1, which lies between the amine and methyl substituents: this protonation is reflected by an increase in the bond angle at N1 [C1—N1—C2 = 121.09 (15)°], when compared with the unprotonated atom N3 [C1—N3—C4 = 116.52 (18)°], and the corresponding angle of 116.01 (18)° in neutral 2-amino-4-methoxy-6-methylpyrimidine (Glidewell <italic>et al.</italic>, 2003<xref ref-type="bibr" rid="bb7"> ▸</xref>). An intramolecular O—H⋯O hydrogen bond occurs within the anion (Table 1<xref ref-type="table" rid="table1"> ▸</xref>).</p></sec><sec id="sec3"><title>supramolecular features </title><p>The protonated N atom (N1) and 2-amino group (N2) of the cation interacts with the O1 and O2 oxygen atoms of the carboxylate anion through a pair of N—H⋯O hydrogen bonds (Table 1<xref ref-type="table" rid="table1"> ▸</xref>), forming an eight-membered ring motif <inline-formula><inline-graphic xlink:href="e-73-01305-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8). Inversion-related <inline-formula><inline-graphic xlink:href="e-73-01305-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) ring motifs are further bridged by N—H⋯O hydrogen bonds thereby forming a <italic>DDAA</italic> tetramer (<italic>D</italic> stands for hydrogen-bond donor and <italic>A</italic> stands for hydrogen-bond acceptor). This set of fused rings can be represented by the graph-set notations <inline-formula><inline-graphic xlink:href="e-73-01305-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8), <inline-formula><inline-graphic xlink:href="e-73-01305-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) and <inline-formula><inline-graphic xlink:href="e-73-01305-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8). This type of motif has been reported previously in the crystal structures of trimethoprim hydrogen glutarate (Robert <italic>et al.</italic>, 2001<xref ref-type="bibr" rid="bb13"> ▸</xref>) and 2-amino-4-methoxy-6-methylpyridinium trifluoroacetate (Jeevaraj <italic>et al.</italic>, 2016<xref ref-type="bibr" rid="bb10"> ▸</xref>). These arrays are further linked <italic>via</italic> pairwise C—H⋯O hydrogen bonds to generate another <inline-formula><inline-graphic xlink:href="e-73-01305-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) ring motif as part of a [100] chain (Fig. 2<xref ref-type="fig" rid="fig2"> ▸</xref>).</p></sec><sec id="sec4"><title>Hirshfeld surface analysis </title><p>The <italic>d</italic><sub>norm</sub> parameter takes negative or positive values depending on whether the inter-molecular contact is shorter or longer, respectively, than the van der Waals radii (Spackman & Jayatilaka <italic>et al.</italic>, 2009<xref ref-type="bibr" rid="bb15"> ▸</xref>; McKinnon <italic>et al.</italic>, 2007<xref ref-type="bibr" rid="bb12"> ▸</xref>). The <italic>d</italic><sub>norm</sub> surface of the ion-pair in (I)<xref ref-type="chem" rid="scheme1"></xref> is shown in Fig. 3<xref ref-type="fig" rid="fig3"> ▸</xref>: this naturally neglects hydrogen bonds (intra-anion O—H⋯O and N—H⋯O cation-to-anion) that occur within the asymmetric unit. The red points represent closer contacts and negative <italic>d</italic><sub>norm</sub> values on the surface corresponding to the N—H⋯O and C—H⋯O interactions are light red in colour. Two-dimensional fingerprint plots from the Hirshfeld surface analysis, as shown in Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>, give a break-down of different contacts as follows: H⋯H (44.2%), C⋯H/H⋯C (19.6%), O⋯H/H⋯O (20.9%), C⋯O/O⋯C (3.0%), C⋯C (2.9%), N⋯H/H⋯N (8.1%) and O⋯O (1.0%). Two ‘wingtips’ in the fingerprint plot are related to the strong H⋯O and O⋯H interactions.</p></sec><sec id="sec5"><title>Database survey </title><p>A search of the Cambridge Structural Database (Version 5.37, update February 2017; Groom <italic>et al.</italic>, 2016<xref ref-type="bibr" rid="bb8"> ▸</xref>) for 2-amino-4-methoxy-6-methylpyrimidine yielded seven structures: VAQSOW, VAQSUC, VAQSEM, VAQSIQ, VAQRUB and VAQSAI (Aakeroy <italic>et al.</italic>, 2003<xref ref-type="bibr" rid="bb1"> ▸</xref>) and NUQTOJ (Jasinski <italic>et al.</italic> (2010<xref ref-type="bibr" rid="bb9"> ▸</xref>).</p></sec><sec id="sec6"><title>Synthesis and crystallization </title><p>The title compound was synthesized by mixing hot methanolic solutions (20 ml) of 2-amino-4-methoxy-6-methylpyrimidine (0.139 mg) and 2-hydroxybenzoic acid (0.156 mg) in a 1:1 molar ratio. The mixed solutions were warmed few minutes over a waterbath and then cooled and kept at room temperature for slow evaporation. After a few days, colourless block-shaped crystals of (I)<xref ref-type="chem" rid="scheme1"></xref> were obtained (yield = 65%).</p></sec><sec id="sec7"><title>Refinement </title><p>Crystal data, data collection and structure refinement details are summarized in Table 2<xref ref-type="table" rid="table2"> ▸</xref>. The hydrogen atoms were positioned geometrically (N—H = 0.86, O—H = 0.82 and C—H = 0.96 or 0.93 Å) and were refined using a riding model, with <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C) or 1.5<italic>U</italic><sub>eq</sub>(methyl C). A rotating-group model was used for the methyl group.</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, 1. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989017011252/hb7693sup1.cif">10.1107/S2056989017011252/hb7693sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-73-01305-sup1.cif" orientation="portrait" id="d35e180" 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="https://doi.org/10.1107/S2056989017011252/hb7693Isup2.hkl">10.1107/S2056989017011252/hb7693Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-73-01305-Isup2.hkl" orientation="portrait" id="d35e187" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-73-01305-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="https://doi.org/10.1107/S2056989017011252/hb7693Isup3.cml">10.1107/S2056989017011252/hb7693Isup3.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=1559280">1559280</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?hb7693&file=hb7693sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?hb7693sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hb7693&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><app-group><app><title>supplementary crystallographic information</title><sec id="d1e136" sec-type="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e145"><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>6</sub>H<sub>10</sub>N<sub>3</sub>O<sup>+</sup>·C<sub>7</sub>H<sub>5</sub>O<sub>3</sub><sup>−</sup></td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 584</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 277.28</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.358 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>c</italic></td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 2ybc</td><td rowspan="1" colspan="1">Cell parameters from 4033 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 9.4291 (12) Å</td><td rowspan="1" colspan="1">θ = 2.5–27.5°</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 15.0620 (19) Å</td><td rowspan="1" colspan="1">µ = 0.10 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.1595 (11) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 296 K</td></tr><tr><td rowspan="1" colspan="1">β = 128.252 (6)°</td><td rowspan="1" colspan="1">Block, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1356.1 (3) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.55 × 0.33 × 0.16 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 4</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e279" sec-type="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e288"><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">Bruker KappaCCD APEXII diffractometer</td><td rowspan="1" colspan="1">4033 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">2373 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> = 0.042</td></tr><tr><td rowspan="1" colspan="1">ω and φ scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 30.2°, θ<sub>min</sub> = 2.5°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (SADABS; Bruker, 2004)</td><td rowspan="1" colspan="1"><italic>h</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.960, <italic>T</italic><sub>max</sub> = 0.984</td><td rowspan="1" colspan="1"><italic>k</italic> = −21→21</td></tr><tr><td rowspan="1" colspan="1">33325 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −17→17</td></tr></table></table-wrap></sec><sec id="d1e393" sec-type="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e402"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic><sup>2</sup></td><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.056</td><td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.164</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>S</italic> = 1.02</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0587<italic>P</italic>)<sup>2</sup> + 0.4004<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">4033 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">183 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.21 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">0 restraints</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.19 e Å<sup>−</sup><sup>3</sup></td></tr></table></table-wrap></sec><sec id="d1e549" sec-type="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e559"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles</td></tr><tr><td rowspan="1" colspan="1">Refinement. Refinement of F<sup>2</sup> against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F<sup>2</sup>, conventional R-factors R are based
on F, with F set to zero for negative F<sup>2</sup>. The threshold expression of
F<sup>2</sup> > 2sigma(F<sup>2</sup>) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F<sup>2</sup> are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.</td></tr></table></table-wrap></sec><sec id="d1e593" sec-type="tablewrapcoords"><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e605"><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">1.29929 (16)</td><td rowspan="1" colspan="1">0.42997 (10)</td><td rowspan="1" colspan="1">1.00372 (13)</td><td rowspan="1" colspan="1">0.0632 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.97381 (17)</td><td rowspan="1" colspan="1">0.55436 (9)</td><td rowspan="1" colspan="1">0.63943 (14)</td><td rowspan="1" colspan="1">0.0475 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.72932 (19)</td><td rowspan="1" colspan="1">0.50804 (12)</td><td rowspan="1" colspan="1">0.62236 (17)</td><td rowspan="1" colspan="1">0.0659 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">1.01155 (18)</td><td rowspan="1" colspan="1">0.46656 (10)</td><td rowspan="1" colspan="1">0.81604 (14)</td><td rowspan="1" colspan="1">0.0486 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.9058 (2)</td><td rowspan="1" colspan="1">0.50922 (12)</td><td rowspan="1" colspan="1">0.69373 (17)</td><td rowspan="1" colspan="1">0.0482 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">1.1545 (2)</td><td rowspan="1" colspan="1">0.55729 (11)</td><td rowspan="1" colspan="1">0.70701 (17)</td><td rowspan="1" colspan="1">0.0465 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">1.2648 (2)</td><td rowspan="1" colspan="1">0.51464 (12)</td><td rowspan="1" colspan="1">0.82987 (18)</td><td rowspan="1" colspan="1">0.0510 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">1.1868 (2)</td><td rowspan="1" colspan="1">0.46995 (11)</td><td rowspan="1" colspan="1">0.88151 (17)</td><td rowspan="1" colspan="1">0.0472 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">1.2254 (3)</td><td rowspan="1" colspan="1">0.38111 (18)</td><td rowspan="1" colspan="1">1.0601 (3)</td><td rowspan="1" colspan="1">0.0863 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">1.2148 (3)</td><td rowspan="1" colspan="1">0.60934 (14)</td><td rowspan="1" colspan="1">0.6387 (2)</td><td rowspan="1" colspan="1">0.0620 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.75239 (17)</td><td rowspan="1" colspan="1">0.63571 (9)</td><td rowspan="1" colspan="1">0.38790 (13)</td><td rowspan="1" colspan="1">0.0593 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.51173 (16)</td><td rowspan="1" colspan="1">0.57024 (9)</td><td rowspan="1" colspan="1">0.34276 (13)</td><td rowspan="1" colspan="1">0.0597 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.7259 (2)</td><td rowspan="1" colspan="1">0.72936 (11)</td><td rowspan="1" colspan="1">0.20277 (15)</td><td rowspan="1" colspan="1">0.0756 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.5836 (2)</td><td rowspan="1" colspan="1">0.62036 (11)</td><td rowspan="1" colspan="1">0.30856 (17)</td><td rowspan="1" colspan="1">0.0459 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.4695 (2)</td><td rowspan="1" colspan="1">0.66507 (10)</td><td rowspan="1" colspan="1">0.16945 (16)</td><td rowspan="1" colspan="1">0.0445 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.5463 (3)</td><td rowspan="1" colspan="1">0.71779 (12)</td><td rowspan="1" colspan="1">0.12434 (19)</td><td rowspan="1" colspan="1">0.0554 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.4349 (4)</td><td rowspan="1" colspan="1">0.75988 (14)</td><td rowspan="1" colspan="1">−0.0047 (2)</td><td rowspan="1" colspan="1">0.0723 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.2513 (3)</td><td rowspan="1" colspan="1">0.74946 (14)</td><td rowspan="1" colspan="1">−0.0879 (2)</td><td rowspan="1" colspan="1">0.0719 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.1737 (3)</td><td rowspan="1" colspan="1">0.69718 (14)</td><td rowspan="1" colspan="1">−0.0458 (2)</td><td rowspan="1" colspan="1">0.0649 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.2822 (2)</td><td rowspan="1" colspan="1">0.65538 (12)</td><td rowspan="1" colspan="1">0.08200 (19)</td><td rowspan="1" colspan="1">0.0529 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.90150</td><td rowspan="1" colspan="1">0.58160</td><td rowspan="1" colspan="1">0.56090</td><td rowspan="1" colspan="1">0.0570*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2A</td><td rowspan="1" colspan="1">0.68270</td><td rowspan="1" colspan="1">0.47990</td><td rowspan="1" colspan="1">0.65460</td><td rowspan="1" colspan="1">0.0790*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2B</td><td rowspan="1" colspan="1">0.66070</td><td rowspan="1" colspan="1">0.53540</td><td rowspan="1" colspan="1">0.54350</td><td rowspan="1" colspan="1">0.0790*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">1.38930</td><td rowspan="1" colspan="1">0.51480</td><td rowspan="1" colspan="1">0.87920</td><td rowspan="1" colspan="1">0.0610*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5A</td><td rowspan="1" colspan="1">1.14960</td><td rowspan="1" colspan="1">0.41960</td><td rowspan="1" colspan="1">1.06650</td><td rowspan="1" colspan="1">0.1290*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5B</td><td rowspan="1" colspan="1">1.32220</td><td rowspan="1" colspan="1">0.35930</td><td rowspan="1" colspan="1">1.15160</td><td rowspan="1" colspan="1">0.1290*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5C</td><td rowspan="1" colspan="1">1.15550</td><td rowspan="1" colspan="1">0.33200</td><td rowspan="1" colspan="1">0.99970</td><td rowspan="1" colspan="1">0.1290*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6A</td><td rowspan="1" colspan="1">1.22890</td><td rowspan="1" colspan="1">0.67050</td><td rowspan="1" colspan="1">0.66590</td><td rowspan="1" colspan="1">0.0930*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6B</td><td rowspan="1" colspan="1">1.12630</td><td rowspan="1" colspan="1">0.60460</td><td rowspan="1" colspan="1">0.53890</td><td rowspan="1" colspan="1">0.0930*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6C</td><td rowspan="1" colspan="1">1.32820</td><td rowspan="1" colspan="1">0.58650</td><td rowspan="1" colspan="1">0.66740</td><td rowspan="1" colspan="1">0.0930*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.77590</td><td rowspan="1" colspan="1">0.70480</td><td rowspan="1" colspan="1">0.27870</td><td rowspan="1" colspan="1">0.1130*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">0.48530</td><td rowspan="1" colspan="1">0.79540</td><td rowspan="1" colspan="1">−0.03500</td><td rowspan="1" colspan="1">0.0870*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">0.17840</td><td rowspan="1" colspan="1">0.77820</td><td rowspan="1" colspan="1">−0.17400</td><td rowspan="1" colspan="1">0.0860*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.04900</td><td rowspan="1" colspan="1">0.69010</td><td rowspan="1" colspan="1">−0.10300</td><td rowspan="1" colspan="1">0.0780*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.22980</td><td rowspan="1" colspan="1">0.61990</td><td rowspan="1" colspan="1">0.11070</td><td rowspan="1" colspan="1">0.0640*</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e1064" sec-type="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e1076"><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">0.0472 (7)</td><td rowspan="1" colspan="1">0.0777 (9)</td><td rowspan="1" colspan="1">0.0528 (7)</td><td rowspan="1" colspan="1">0.0025 (6)</td><td rowspan="1" colspan="1">0.0250 (6)</td><td rowspan="1" colspan="1">0.0194 (6)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0436 (7)</td><td rowspan="1" colspan="1">0.0531 (8)</td><td rowspan="1" colspan="1">0.0423 (7)</td><td rowspan="1" colspan="1">−0.0014 (6)</td><td rowspan="1" colspan="1">0.0249 (6)</td><td rowspan="1" colspan="1">0.0067 (6)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0418 (8)</td><td rowspan="1" colspan="1">0.0915 (12)</td><td rowspan="1" colspan="1">0.0561 (9)</td><td rowspan="1" colspan="1">0.0001 (8)</td><td rowspan="1" colspan="1">0.0262 (7)</td><td rowspan="1" colspan="1">0.0254 (9)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0426 (7)</td><td rowspan="1" colspan="1">0.0549 (8)</td><td rowspan="1" colspan="1">0.0442 (8)</td><td rowspan="1" colspan="1">−0.0032 (6)</td><td rowspan="1" colspan="1">0.0249 (6)</td><td rowspan="1" colspan="1">0.0054 (6)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0433 (8)</td><td rowspan="1" colspan="1">0.0543 (10)</td><td rowspan="1" colspan="1">0.0446 (9)</td><td rowspan="1" colspan="1">−0.0026 (7)</td><td rowspan="1" colspan="1">0.0260 (8)</td><td rowspan="1" colspan="1">0.0036 (7)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0468 (9)</td><td rowspan="1" colspan="1">0.0486 (9)</td><td rowspan="1" colspan="1">0.0478 (9)</td><td rowspan="1" colspan="1">−0.0061 (7)</td><td rowspan="1" colspan="1">0.0311 (8)</td><td rowspan="1" colspan="1">−0.0041 (7)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0417 (8)</td><td rowspan="1" colspan="1">0.0597 (10)</td><td rowspan="1" colspan="1">0.0492 (9)</td><td rowspan="1" colspan="1">−0.0022 (7)</td><td rowspan="1" colspan="1">0.0269 (8)</td><td rowspan="1" colspan="1">0.0016 (8)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0447 (9)</td><td rowspan="1" colspan="1">0.0496 (9)</td><td rowspan="1" colspan="1">0.0428 (9)</td><td rowspan="1" colspan="1">0.0003 (7)</td><td rowspan="1" colspan="1">0.0248 (7)</td><td rowspan="1" colspan="1">0.0021 (7)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0666 (13)</td><td rowspan="1" colspan="1">0.1089 (19)</td><td rowspan="1" colspan="1">0.0698 (14)</td><td rowspan="1" colspan="1">−0.0019 (12)</td><td rowspan="1" colspan="1">0.0355 (12)</td><td rowspan="1" colspan="1">0.0374 (13)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0594 (11)</td><td rowspan="1" colspan="1">0.0715 (12)</td><td rowspan="1" colspan="1">0.0613 (11)</td><td rowspan="1" colspan="1">−0.0109 (9)</td><td rowspan="1" colspan="1">0.0405 (10)</td><td rowspan="1" colspan="1">0.0042 (9)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0508 (7)</td><td rowspan="1" colspan="1">0.0703 (8)</td><td rowspan="1" colspan="1">0.0485 (7)</td><td rowspan="1" colspan="1">−0.0047 (6)</td><td rowspan="1" colspan="1">0.0266 (6)</td><td rowspan="1" colspan="1">0.0078 (6)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0537 (7)</td><td rowspan="1" colspan="1">0.0726 (9)</td><td rowspan="1" colspan="1">0.0564 (7)</td><td rowspan="1" colspan="1">0.0029 (6)</td><td rowspan="1" colspan="1">0.0359 (6)</td><td rowspan="1" colspan="1">0.0161 (6)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0751 (9)</td><td rowspan="1" colspan="1">0.0866 (11)</td><td rowspan="1" colspan="1">0.0666 (9)</td><td rowspan="1" colspan="1">−0.0209 (8)</td><td rowspan="1" colspan="1">0.0446 (8)</td><td rowspan="1" colspan="1">0.0052 (8)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0511 (9)</td><td rowspan="1" colspan="1">0.0460 (9)</td><td rowspan="1" colspan="1">0.0460 (9)</td><td rowspan="1" colspan="1">0.0039 (7)</td><td rowspan="1" colspan="1">0.0328 (8)</td><td rowspan="1" colspan="1">0.0010 (7)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0540 (9)</td><td rowspan="1" colspan="1">0.0387 (8)</td><td rowspan="1" colspan="1">0.0421 (8)</td><td rowspan="1" colspan="1">0.0046 (7)</td><td rowspan="1" colspan="1">0.0304 (8)</td><td rowspan="1" colspan="1">0.0002 (6)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0703 (12)</td><td rowspan="1" colspan="1">0.0485 (9)</td><td rowspan="1" colspan="1">0.0518 (10)</td><td rowspan="1" colspan="1">−0.0050 (8)</td><td rowspan="1" colspan="1">0.0400 (10)</td><td rowspan="1" colspan="1">−0.0011 (8)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.1055 (18)</td><td rowspan="1" colspan="1">0.0579 (12)</td><td rowspan="1" colspan="1">0.0625 (13)</td><td rowspan="1" colspan="1">−0.0020 (11)</td><td rowspan="1" colspan="1">0.0565 (13)</td><td rowspan="1" colspan="1">0.0097 (10)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0920 (16)</td><td rowspan="1" colspan="1">0.0589 (12)</td><td rowspan="1" colspan="1">0.0491 (11)</td><td rowspan="1" colspan="1">0.0191 (11)</td><td rowspan="1" colspan="1">0.0359 (12)</td><td rowspan="1" colspan="1">0.0094 (9)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0653 (12)</td><td rowspan="1" colspan="1">0.0627 (12)</td><td rowspan="1" colspan="1">0.0528 (11)</td><td rowspan="1" colspan="1">0.0186 (9)</td><td rowspan="1" colspan="1">0.0296 (10)</td><td rowspan="1" colspan="1">0.0042 (9)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0571 (10)</td><td rowspan="1" colspan="1">0.0490 (10)</td><td rowspan="1" colspan="1">0.0502 (10)</td><td rowspan="1" colspan="1">0.0100 (8)</td><td rowspan="1" colspan="1">0.0320 (9)</td><td rowspan="1" colspan="1">0.0026 (8)</td></tr></table></table-wrap></sec><sec id="d1e1437" sec-type="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1447"><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—C4</td><td rowspan="1" colspan="1">1.321 (2)</td><td rowspan="1" colspan="1">C5—H5A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">O1—C5</td><td rowspan="1" colspan="1">1.445 (4)</td><td rowspan="1" colspan="1">C5—H5C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">O2—C7</td><td rowspan="1" colspan="1">1.271 (3)</td><td rowspan="1" colspan="1">C5—H5B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">O3—C7</td><td rowspan="1" colspan="1">1.245 (3)</td><td rowspan="1" colspan="1">C6—H6B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">O4—C9</td><td rowspan="1" colspan="1">1.345 (3)</td><td rowspan="1" colspan="1">C6—H6C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">O4—H4</td><td rowspan="1" colspan="1">0.8200</td><td rowspan="1" colspan="1">C6—H6A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">N1—C2</td><td rowspan="1" colspan="1">1.359 (3)</td><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.490 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.354 (3)</td><td rowspan="1" colspan="1">C8—C13</td><td rowspan="1" colspan="1">1.395 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—C1</td><td rowspan="1" colspan="1">1.317 (3)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.396 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C1</td><td rowspan="1" colspan="1">1.335 (2)</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C4</td><td rowspan="1" colspan="1">1.318 (3)</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.370 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—H1</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.372 (4)</td></tr><tr><td rowspan="1" colspan="1">N2—H2B</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.375 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—H2A</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C2—C6</td><td rowspan="1" colspan="1">1.488 (3)</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.343 (2)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.400 (3)</td><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9300</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">O1···C3<sup>i</sup></td><td rowspan="1" colspan="1">3.374 (3)</td><td rowspan="1" colspan="1">C7···H10<sup>iv</sup></td><td rowspan="1" colspan="1">2.8800</td></tr><tr><td rowspan="1" colspan="1">O2···C3<sup>ii</sup></td><td rowspan="1" colspan="1">3.411 (2)</td><td rowspan="1" colspan="1">C7···H2B</td><td rowspan="1" colspan="1">2.7800</td></tr><tr><td rowspan="1" colspan="1">O2···N1</td><td rowspan="1" colspan="1">2.7033 (19)</td><td rowspan="1" colspan="1">C7···H1</td><td rowspan="1" colspan="1">2.7100</td></tr><tr><td rowspan="1" colspan="1">O2···O4</td><td rowspan="1" colspan="1">2.534 (2)</td><td rowspan="1" colspan="1">C7···H4</td><td rowspan="1" colspan="1">2.4200</td></tr><tr><td rowspan="1" colspan="1">O3···N2<sup>iii</sup></td><td rowspan="1" colspan="1">2.816 (3)</td><td rowspan="1" colspan="1">C9···H5B<sup>vi</sup></td><td rowspan="1" colspan="1">3.0500</td></tr><tr><td rowspan="1" colspan="1">O3···N2</td><td rowspan="1" colspan="1">2.830 (2)</td><td rowspan="1" colspan="1">C12···H6A<sup>ix</sup></td><td rowspan="1" colspan="1">3.0300</td></tr><tr><td rowspan="1" colspan="1">O4···O2</td><td rowspan="1" colspan="1">2.534 (2)</td><td rowspan="1" colspan="1">C13···H6A<sup>ix</sup></td><td rowspan="1" colspan="1">2.9700</td></tr><tr><td rowspan="1" colspan="1">O1···H3<sup>i</sup></td><td rowspan="1" colspan="1">2.4800</td><td rowspan="1" colspan="1">H1···O2</td><td rowspan="1" colspan="1">1.8400</td></tr><tr><td rowspan="1" colspan="1">O2···H4</td><td rowspan="1" colspan="1">1.8100</td><td rowspan="1" colspan="1">H1···O3</td><td rowspan="1" colspan="1">2.9200</td></tr><tr><td rowspan="1" colspan="1">O2···H6B</td><td rowspan="1" colspan="1">2.8300</td><td rowspan="1" colspan="1">H1···C7</td><td rowspan="1" colspan="1">2.7100</td></tr><tr><td rowspan="1" colspan="1">O2···H1</td><td rowspan="1" colspan="1">1.8400</td><td rowspan="1" colspan="1">H1···H2B</td><td rowspan="1" colspan="1">2.2600</td></tr><tr><td rowspan="1" colspan="1">O3···H2B</td><td rowspan="1" colspan="1">1.9900</td><td rowspan="1" colspan="1">H1···H6B</td><td rowspan="1" colspan="1">2.3200</td></tr><tr><td rowspan="1" colspan="1">O3···H13</td><td rowspan="1" colspan="1">2.5100</td><td rowspan="1" colspan="1">H2A···O3<sup>iii</sup></td><td rowspan="1" colspan="1">2.0000</td></tr><tr><td rowspan="1" colspan="1">O3···H1</td><td rowspan="1" colspan="1">2.9200</td><td rowspan="1" colspan="1">H2A···H2B<sup>iii</sup></td><td rowspan="1" colspan="1">2.5800</td></tr><tr><td rowspan="1" colspan="1">O3···H2A<sup>iii</sup></td><td rowspan="1" colspan="1">2.0000</td><td rowspan="1" colspan="1">H2B···O3</td><td rowspan="1" colspan="1">1.9900</td></tr><tr><td rowspan="1" colspan="1">O3···H6C<sup>ii</sup></td><td rowspan="1" colspan="1">2.8500</td><td rowspan="1" colspan="1">H2B···C7</td><td rowspan="1" colspan="1">2.7800</td></tr><tr><td rowspan="1" colspan="1">O3···H10<sup>iv</sup></td><td rowspan="1" colspan="1">2.6100</td><td rowspan="1" colspan="1">H2B···H1</td><td rowspan="1" colspan="1">2.2600</td></tr><tr><td rowspan="1" colspan="1">O4···H12<sup>v</sup></td><td rowspan="1" colspan="1">2.7200</td><td rowspan="1" colspan="1">H2B···H2A<sup>iii</sup></td><td rowspan="1" colspan="1">2.5800</td></tr><tr><td rowspan="1" colspan="1">O4···H5B<sup>vi</sup></td><td rowspan="1" colspan="1">2.8600</td><td rowspan="1" colspan="1">H3···H6C</td><td rowspan="1" colspan="1">2.5100</td></tr><tr><td rowspan="1" colspan="1">N1···O2</td><td rowspan="1" colspan="1">2.7033 (19)</td><td rowspan="1" colspan="1">H3···O1<sup>i</sup></td><td rowspan="1" colspan="1">2.4800</td></tr><tr><td rowspan="1" colspan="1">N2···O3</td><td rowspan="1" colspan="1">2.830 (2)</td><td rowspan="1" colspan="1">H3···C3<sup>i</sup></td><td rowspan="1" colspan="1">3.0100</td></tr><tr><td rowspan="1" colspan="1">N2···O3<sup>iii</sup></td><td rowspan="1" colspan="1">2.816 (3)</td><td rowspan="1" colspan="1">H3···H3<sup>i</sup></td><td rowspan="1" colspan="1">2.3600</td></tr><tr><td rowspan="1" colspan="1">N3···H5C</td><td rowspan="1" colspan="1">2.6800</td><td rowspan="1" colspan="1">H4···O2</td><td rowspan="1" colspan="1">1.8100</td></tr><tr><td rowspan="1" colspan="1">N3···H5A</td><td rowspan="1" colspan="1">2.5600</td><td rowspan="1" colspan="1">H4···C7</td><td rowspan="1" colspan="1">2.4200</td></tr><tr><td rowspan="1" colspan="1">C2···C11<sup>vii</sup></td><td rowspan="1" colspan="1">3.551 (3)</td><td rowspan="1" colspan="1">H4···H12<sup>v</sup></td><td rowspan="1" colspan="1">2.5700</td></tr><tr><td rowspan="1" colspan="1">C2···C12<sup>vii</sup></td><td rowspan="1" colspan="1">3.582 (3)</td><td rowspan="1" colspan="1">H5A···N3</td><td rowspan="1" colspan="1">2.5600</td></tr><tr><td rowspan="1" colspan="1">C3···O1<sup>i</sup></td><td rowspan="1" colspan="1">3.374 (3)</td><td rowspan="1" colspan="1">H5B···O4<sup>x</sup></td><td rowspan="1" colspan="1">2.8600</td></tr><tr><td rowspan="1" colspan="1">C3···C12<sup>vii</sup></td><td rowspan="1" colspan="1">3.492 (3)</td><td rowspan="1" colspan="1">H5B···C9<sup>x</sup></td><td rowspan="1" colspan="1">3.0500</td></tr><tr><td rowspan="1" colspan="1">C3···C7<sup>ii</sup></td><td rowspan="1" colspan="1">3.463 (3)</td><td rowspan="1" colspan="1">H5C···N3</td><td rowspan="1" colspan="1">2.6800</td></tr><tr><td rowspan="1" colspan="1">C3···O2<sup>ii</sup></td><td rowspan="1" colspan="1">3.411 (2)</td><td rowspan="1" colspan="1">H6A···C13<sup>v</sup></td><td rowspan="1" colspan="1">2.9700</td></tr><tr><td rowspan="1" colspan="1">C4···C12<sup>vii</sup></td><td rowspan="1" colspan="1">3.556 (3)</td><td rowspan="1" colspan="1">H6A···C12<sup>v</sup></td><td rowspan="1" colspan="1">3.0300</td></tr><tr><td rowspan="1" colspan="1">C4···C13<sup>vii</sup></td><td rowspan="1" colspan="1">3.441 (3)</td><td rowspan="1" colspan="1">H6B···O2</td><td rowspan="1" colspan="1">2.8300</td></tr><tr><td rowspan="1" colspan="1">C6···C12<sup>v</sup></td><td rowspan="1" colspan="1">3.550 (3)</td><td rowspan="1" colspan="1">H6B···H1</td><td rowspan="1" colspan="1">2.3200</td></tr><tr><td rowspan="1" colspan="1">C7···C3<sup>ii</sup></td><td rowspan="1" colspan="1">3.463 (3)</td><td rowspan="1" colspan="1">H6C···H3</td><td rowspan="1" colspan="1">2.5100</td></tr><tr><td rowspan="1" colspan="1">C11···C2<sup>viii</sup></td><td rowspan="1" colspan="1">3.551 (3)</td><td rowspan="1" colspan="1">H6C···O3<sup>ii</sup></td><td rowspan="1" colspan="1">2.8500</td></tr><tr><td rowspan="1" colspan="1">C12···C3<sup>viii</sup></td><td rowspan="1" colspan="1">3.492 (3)</td><td rowspan="1" colspan="1">H10···O3<sup>xi</sup></td><td rowspan="1" colspan="1">2.6100</td></tr><tr><td rowspan="1" colspan="1">C12···C2<sup>viii</sup></td><td rowspan="1" colspan="1">3.582 (3)</td><td rowspan="1" colspan="1">H10···C7<sup>xi</sup></td><td rowspan="1" colspan="1">2.8800</td></tr><tr><td rowspan="1" colspan="1">C12···C4<sup>viii</sup></td><td rowspan="1" colspan="1">3.556 (3)</td><td rowspan="1" colspan="1">H12···O4<sup>ix</sup></td><td rowspan="1" colspan="1">2.7200</td></tr><tr><td rowspan="1" colspan="1">C12···C6<sup>ix</sup></td><td rowspan="1" colspan="1">3.550 (3)</td><td rowspan="1" colspan="1">H12···H4<sup>ix</sup></td><td rowspan="1" colspan="1">2.5700</td></tr><tr><td rowspan="1" colspan="1">C13···C4<sup>viii</sup></td><td rowspan="1" colspan="1">3.441 (3)</td><td rowspan="1" colspan="1">H13···O3</td><td rowspan="1" colspan="1">2.5100</td></tr><tr><td rowspan="1" colspan="1">C3···H3<sup>i</sup></td><td rowspan="1" colspan="1">3.0100</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">C4—O1—C5</td><td rowspan="1" colspan="1">118.6 (2)</td><td rowspan="1" colspan="1">C2—C6—H6A</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C9—O4—H4</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">C2—C6—H6C</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C2</td><td rowspan="1" colspan="1">121.09 (15)</td><td rowspan="1" colspan="1">H6A—C6—H6B</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C1—N3—C4</td><td rowspan="1" colspan="1">116.52 (18)</td><td rowspan="1" colspan="1">C2—C6—H6B</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C1—N1—H1</td><td rowspan="1" colspan="1">119.00</td><td rowspan="1" colspan="1">H6B—C6—H6C</td><td rowspan="1" colspan="1">110.00</td></tr><tr><td rowspan="1" colspan="1">C2—N1—H1</td><td rowspan="1" colspan="1">119.00</td><td rowspan="1" colspan="1">H6A—C6—H6C</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">H2A—N2—H2B</td><td rowspan="1" colspan="1">120.00</td><td rowspan="1" colspan="1">O2—C7—C8</td><td rowspan="1" colspan="1">117.66 (18)</td></tr><tr><td rowspan="1" colspan="1">C1—N2—H2A</td><td rowspan="1" colspan="1">120.00</td><td rowspan="1" colspan="1">O3—C7—C8</td><td rowspan="1" colspan="1">119.57 (18)</td></tr><tr><td rowspan="1" colspan="1">C1—N2—H2B</td><td rowspan="1" colspan="1">120.00</td><td rowspan="1" colspan="1">O2—C7—O3</td><td rowspan="1" colspan="1">122.77 (16)</td></tr><tr><td rowspan="1" colspan="1">N2—C1—N3</td><td rowspan="1" colspan="1">119.68 (19)</td><td rowspan="1" colspan="1">C7—C8—C13</td><td rowspan="1" colspan="1">120.12 (18)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—N3</td><td rowspan="1" colspan="1">122.16 (19)</td><td rowspan="1" colspan="1">C9—C8—C13</td><td rowspan="1" colspan="1">118.69 (16)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—N2</td><td rowspan="1" colspan="1">118.17 (16)</td><td rowspan="1" colspan="1">C7—C8—C9</td><td rowspan="1" colspan="1">121.19 (19)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—C6</td><td rowspan="1" colspan="1">116.68 (16)</td><td rowspan="1" colspan="1">O4—C9—C10</td><td rowspan="1" colspan="1">118.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C6</td><td rowspan="1" colspan="1">125.0 (2)</td><td rowspan="1" colspan="1">C8—C9—C10</td><td rowspan="1" colspan="1">119.4 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—C3</td><td rowspan="1" colspan="1">118.35 (19)</td><td rowspan="1" colspan="1">O4—C9—C8</td><td rowspan="1" colspan="1">121.81 (17)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">118.0 (2)</td><td rowspan="1" colspan="1">C9—C10—C11</td><td rowspan="1" colspan="1">120.6 (3)</td></tr><tr><td rowspan="1" colspan="1">N3—C4—C3</td><td rowspan="1" colspan="1">123.91 (16)</td><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">120.8 (2)</td></tr><tr><td rowspan="1" colspan="1">O1—C4—C3</td><td rowspan="1" colspan="1">116.42 (19)</td><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">119.3 (2)</td></tr><tr><td rowspan="1" colspan="1">O1—C4—N3</td><td rowspan="1" colspan="1">119.67 (18)</td><td rowspan="1" colspan="1">C8—C13—C12</td><td rowspan="1" colspan="1">121.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">121.00</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">120.00</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">121.00</td><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">120.00</td></tr><tr><td rowspan="1" colspan="1">O1—C5—H5B</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.00</td></tr><tr><td rowspan="1" colspan="1">O1—C5—H5C</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.00</td></tr><tr><td rowspan="1" colspan="1">O1—C5—H5A</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">120.00</td></tr><tr><td rowspan="1" colspan="1">H5A—C5—H5C</td><td rowspan="1" colspan="1">110.00</td><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">120.00</td></tr><tr><td rowspan="1" colspan="1">H5B—C5—H5C</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">C8—C13—H13</td><td rowspan="1" colspan="1">119.00</td></tr><tr><td rowspan="1" colspan="1">H5A—C5—H5B</td><td rowspan="1" colspan="1">110.00</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">119.00</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">C5—O1—C4—N3</td><td rowspan="1" colspan="1">1.9 (3)</td><td rowspan="1" colspan="1">O2—C7—C8—C13</td><td rowspan="1" colspan="1">−175.72 (17)</td></tr><tr><td rowspan="1" colspan="1">C5—O1—C4—C3</td><td rowspan="1" colspan="1">−178.55 (18)</td><td rowspan="1" colspan="1">O3—C7—C8—C9</td><td rowspan="1" colspan="1">−176.44 (18)</td></tr><tr><td rowspan="1" colspan="1">C2—N1—C1—N2</td><td rowspan="1" colspan="1">−179.22 (17)</td><td rowspan="1" colspan="1">O3—C7—C8—C13</td><td rowspan="1" colspan="1">4.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—N1—C1—N3</td><td rowspan="1" colspan="1">0.8 (3)</td><td rowspan="1" colspan="1">C7—C8—C9—O4</td><td rowspan="1" colspan="1">1.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C2—C3</td><td rowspan="1" colspan="1">−0.4 (2)</td><td rowspan="1" colspan="1">C7—C8—C9—C10</td><td rowspan="1" colspan="1">−178.58 (19)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C2—C6</td><td rowspan="1" colspan="1">−179.52 (16)</td><td rowspan="1" colspan="1">C13—C8—C9—O4</td><td rowspan="1" colspan="1">−179.40 (18)</td></tr><tr><td rowspan="1" colspan="1">C4—N3—C1—N1</td><td rowspan="1" colspan="1">−0.5 (3)</td><td rowspan="1" colspan="1">C13—C8—C9—C10</td><td rowspan="1" colspan="1">0.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—N3—C1—N2</td><td rowspan="1" colspan="1">179.56 (17)</td><td rowspan="1" colspan="1">C7—C8—C13—C12</td><td rowspan="1" colspan="1">178.86 (18)</td></tr><tr><td rowspan="1" colspan="1">C1—N3—C4—O1</td><td rowspan="1" colspan="1">179.29 (16)</td><td rowspan="1" colspan="1">C9—C8—C13—C12</td><td rowspan="1" colspan="1">−0.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—N3—C4—C3</td><td rowspan="1" colspan="1">−0.3 (3)</td><td rowspan="1" colspan="1">O4—C9—C10—C11</td><td rowspan="1" colspan="1">179.7 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.3 (3)</td><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">−0.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C2—C3—C4</td><td rowspan="1" colspan="1">178.73 (18)</td><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">−0.2 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—O1</td><td rowspan="1" colspan="1">−178.88 (16)</td><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">0.4 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—N3</td><td rowspan="1" colspan="1">0.7 (3)</td><td rowspan="1" colspan="1">C11—C12—C13—C8</td><td rowspan="1" colspan="1">−0.1 (3)</td></tr><tr><td rowspan="1" colspan="1">O2—C7—C8—C9</td><td rowspan="1" colspan="1">3.7 (3)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+3, −<italic>y</italic>+1, −<italic>z</italic>+2; (ii) −<italic>x</italic>+2, −<italic>y</italic>+1, −<italic>z</italic>+1; (iii) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>+1; (iv) <italic>x</italic>, −<italic>y</italic>+3/2, <italic>z</italic>+1/2; (v) <italic>x</italic>+1, −<italic>y</italic>+3/2, <italic>z</italic>+1/2; (vi) −<italic>x</italic>+2, <italic>y</italic>+1/2, −<italic>z</italic>+3/2; (vii) <italic>x</italic>+1, <italic>y</italic>, <italic>z</italic>+1; (viii) <italic>x</italic>−1, <italic>y</italic>, <italic>z</italic>−1; (ix) <italic>x</italic>−1, −<italic>y</italic>+3/2, <italic>z</italic>−1/2; (x) −<italic>x</italic>+2, <italic>y</italic>−1/2, −<italic>z</italic>+3/2; (xi) <italic>x</italic>, −<italic>y</italic>+3/2, <italic>z</italic>−1/2.</p></sec><sec id="d1e2663" sec-type="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e2672"><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">N1—H1···O2</td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">1.84</td><td rowspan="1" colspan="1">2.7033 (19)</td><td rowspan="1" colspan="1">176</td></tr><tr><td rowspan="1" colspan="1">N2—H2<italic>A</italic>···O3<sup>iii</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.00</td><td rowspan="1" colspan="1">2.816 (3)</td><td rowspan="1" colspan="1">158</td></tr><tr><td rowspan="1" colspan="1">N2—H2<italic>B</italic>···O3</td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">1.99</td><td rowspan="1" colspan="1">2.830 (2)</td><td rowspan="1" colspan="1">165</td></tr><tr><td rowspan="1" colspan="1">O4—H4···O2</td><td rowspan="1" colspan="1">0.82</td><td rowspan="1" colspan="1">1.81</td><td rowspan="1" colspan="1">2.534 (2)</td><td rowspan="1" colspan="1">147</td></tr><tr><td rowspan="1" colspan="1">C3—H3···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.48</td><td rowspan="1" colspan="1">3.374 (3)</td><td rowspan="1" colspan="1">160</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+3, −<italic>y</italic>+1, −<italic>z</italic>+2; (iii) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>+1.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Aakeröy, B. C., Beffert, K., Desper, J. & Elisabeth, E. (2003). <italic>Cryst. Growth Des.</italic><bold>3</bold>, 837–846.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Bruker (2004). <italic>APEX2</italic>, <italic>SAINT</italic> and <italic>SADABS</italic>. Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Condon, M. E., Brady, T. E., Feist, D., Malefyt, T., Marc, P., Quakenbush, L. S., Rodaway, S. J., Shaner, D. L. & Tecle, B. (1993). <italic>Brighton Crop Protection Conference on Weeds</italic>, pp. 41–46. Alton, Hampshire, England: BCPC Publications.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Desiraju, G. R. (1989). <italic>Crystal Engineering: The Design of Organic Solids.</italic> Amsterdam: Elsevier.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Gilchrist, T. L. (1997). <italic>Heterocyclic Chemistry</italic>, 3rd ed., pp. 261–276. Singapore: Addison Wesley Longman.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Glidewell, C., Low, J. N., Melguizo, M. & Quesada, A. (2003). <italic>Acta Cryst.</italic> C<bold>59</bold>, o9–o13.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). <italic>Acta Cryst.</italic> B<bold>72</bold>, 171–179.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010). <italic>Acta Cryst.</italic> E<bold>66</bold>, o1189–o1190.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Jeevaraj, M., Edison, B., Kavitha, S. J., Thanikasalam, K., Britto, S. & Balasubramani, K. (2016). <italic>IUCrData</italic>, <bold>1</bold>, x161010.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Maeno, S., Miura, I., Masuda, K. & Nagata, T. (1990). <italic>Brighton Crop Protection Conference on Pests and Diseases</italic>, pp. 415–422. Alton, Hampshire, England: BCPC Publications.</mixed-citation></ref><ref id="bb12"><mixed-citation publication-type="other">McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). <italic>Chem. Commun.</italic> pp. 3814–3816.</mixed-citation></ref><ref id="bb13"><mixed-citation publication-type="other">Robert, J. J., Raj, S. B. & Muthiah, P. T. (2001). <italic>Acta Cryst.</italic> E<bold>57</bold>, o1206–o1208.</mixed-citation></ref><ref id="bb14"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb15"><mixed-citation publication-type="other">Spackman, M. A. & Jayatilaka, D. (2009). <italic>CrystEngComm</italic>, <bold>11</bold>, 19–32.</mixed-citation></ref><ref id="bb16"><mixed-citation publication-type="other">Spek, A. L. (2009). <italic>Acta Cryst.</italic> D<bold>65</bold>, 148–155.</mixed-citation></ref><ref id="bb17"><mixed-citation publication-type="other">Steiner, T. (2002). <italic>Angew. Chem. Int. Ed.</italic><bold>41</bold>, 48–76.</mixed-citation></ref></ref-list></back><floats-group><fig id="fig1" orientation="portrait" position="float"><label>Figure 1</label><caption><p>The asymmetric unit of (I)<xref ref-type="chem" rid="scheme1"></xref>, with 50% probability displacement ellipsoids. The hydrogen bonds are indicated by dashed lines.</p></caption><graphic xlink:href="e-73-01305-fig1"></graphic></fig><fig id="fig2" orientation="portrait" position="float"><label>Figure 2</label><caption><p>A [100] chain in the crystal of (I)<xref ref-type="chem" rid="scheme1"></xref> incorporating <inline-formula><inline-graphic xlink:href="e-73-01305-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8), <inline-formula><inline-graphic xlink:href="e-73-01305-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) and <inline-formula><inline-graphic xlink:href="e-73-01305-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(12) ring motifs.</p></caption><graphic xlink:href="e-73-01305-fig2"></graphic></fig><fig id="fig3" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Three-dimensional Hirshfeld surface of (I)<xref ref-type="chem" rid="scheme1"></xref>.</p></caption><graphic xlink:href="e-73-01305-fig3"></graphic></fig><fig id="fig4" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Fingerprint plots for (I)<xref ref-type="chem" rid="scheme1"></xref>.</p></caption><graphic xlink:href="e-73-01305-fig4"></graphic></fig><table-wrap id="table1" orientation="portrait" 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 rowspan="1" colspan="1" align="left" valign="top">N1—H1⋯O2</td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">1.84</td><td rowspan="1" colspan="1" align="left" valign="top">2.7033 (19)</td><td rowspan="1" colspan="1" align="left" valign="top">176</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>A</italic>⋯O3<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">2.00</td><td rowspan="1" colspan="1" align="left" valign="top">2.816 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">158</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>B</italic>⋯O3</td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">1.99</td><td rowspan="1" colspan="1" align="left" valign="top">2.830 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">165</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">O4—H4⋯O2</td><td rowspan="1" colspan="1" align="left" valign="top">0.82</td><td rowspan="1" colspan="1" align="left" valign="top">1.81</td><td rowspan="1" colspan="1" align="left" valign="top">2.534 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">147</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C3—H3⋯O1<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.48</td><td rowspan="1" colspan="1" align="left" valign="top">3.374 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">160</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-73-01305-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-73-01305-efi8.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap><table-wrap id="table2" orientation="portrait" position="float"><label>Table 2</label><caption><title>Experimental details</title></caption><table frame="hsides" rules="groups"><tbody valign="top"><tr><td rowspan="1" colspan="2" align="left" valign="top">Crystal data</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td><td rowspan="1" colspan="1" align="left" valign="top">C<sub>6</sub>H<sub>10</sub>N<sub>3</sub>O<sup>+</sup>·C<sub>7</sub>H<sub>5</sub>O<sub>3</sub><sup>−</sup></td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic><sub>r</sub></td><td rowspan="1" colspan="1" align="left" valign="top">277.28</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td><td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>c</italic></td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td><td rowspan="1" colspan="1" align="left" valign="top">296</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>, <italic>b</italic>, <italic>c</italic> (Å)</td><td rowspan="1" colspan="1" align="left" valign="top">9.4291 (12), 15.0620 (19), 12.1595 (11)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">β (°)</td><td rowspan="1" colspan="1" align="left" valign="top">128.252 (6)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic> (Å<sup>3</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">1356.1 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic></td><td rowspan="1" colspan="1" align="left" valign="top">4</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Radiation type</td><td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>α</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.10</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td><td rowspan="1" colspan="1" align="left" valign="top">0.55 × 0.33 × 0.16</td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top">Data collection</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td><td rowspan="1" colspan="1" align="left" valign="top">Bruker KappaCCD APEXII</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Absorption correction</td><td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>SADABS</italic>; Bruker, 2004<xref ref-type="bibr" rid="bb2"> ▸</xref>)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>T</italic><sub>min</sub>, <italic>T</italic><sub>max</sub></td><td rowspan="1" colspan="1" align="left" valign="top">0.960, 0.984</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic> > 2σ(<italic>I</italic>)] reflections</td><td rowspan="1" colspan="1" align="left" valign="top">33325, 4033, 2373</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic><sub>int</sub></td><td rowspan="1" colspan="1" align="left" valign="top">0.042</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub> (Å<sup>−1</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.708</td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top">Refinement</td></tr><tr><td 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 rowspan="1" colspan="1" align="left" valign="top">0.056, 0.164, 1.02</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td><td rowspan="1" colspan="1" align="left" valign="top">4033</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td><td rowspan="1" colspan="1" align="left" valign="top">183</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td><td rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>−3</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.21, −0.19</td></tr></tbody></table><table-wrap-foot><p>Computer programs: <italic>APEX2</italic> and <italic>SAINT</italic> (Bruker, 2004<xref ref-type="bibr" rid="bb2"> ▸</xref>), <italic>SHELXTL</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb14"> ▸</xref>) and <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb16"> ▸</xref>).</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/Pmc/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000980 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Pmc/Corpus/biblio.hfd -nk 000980 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Sante
|area= MersV1
|flux= Pmc
|étape= Corpus
|type= RBID
|clé= PMC:5588567
|texte= Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Pmc/Corpus/RBID.i -Sk "pubmed:28932461" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Pmc/Corpus/biblio.hfd \
| NlmPubMed2Wicri -a MersV1
| This area was generated with Dilib version V0.6.33. |  |