Bis{bis(azido-κN)bis[bis(pyridin-2-yl-κN)amine]cobalt(III)} sulfate dihydrate
Identifieur interne : 000055 ( Pmc/Corpus ); précédent : 000054; suivant : 000056Bis{bis(azido-κN)bis[bis(pyridin-2-yl-κN)amine]cobalt(III)} sulfate dihydrate
Auteurs : Fatima Setifi ; Jacqueline M. Knaust ; Zouaoui Setifi ; Rachid TouzaniSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2016.
Abstract
The crystal structure of bis{bis(azido-κ
Url:
DOI: 10.1107/S2056989016003662
PubMed: 27375867
PubMed Central: 4910331
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Bis{bis(azido-κ<italic>N</italic>)bis[bis(pyridin-2-yl-κ<italic>N</italic>)amine]cobalt(III)} sulfate dihydrate</title><author><name sortKey="Setifi, Fatima" sort="Setifi, Fatima" uniqKey="Setifi F" first="Fatima" last="Setifi">Fatima Setifi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Knaust, Jacqueline M" sort="Knaust, Jacqueline M" uniqKey="Knaust J" first="Jacqueline M." last="Knaust">Jacqueline M. Knaust</name><affiliation><nlm:aff id="b">Department of Chemistry, Mathematics and Physics, Clarion University, 840 Wood Street, Clarion, PA 16214,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Setifi, Zouaoui" sort="Setifi, Zouaoui" uniqKey="Setifi Z" first="Zouaoui" last="Setifi">Zouaoui Setifi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name><affiliation><nlm:aff id="c">Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, and, Faculté Pluridisciplinaire Nador BP 300, Selouane, 62702, Nador,<country>Morocco</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">27375867</idno><idno type="pmc">4910331</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4910331</idno><idno type="RBID">PMC:4910331</idno><idno type="doi">10.1107/S2056989016003662</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000055</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000055</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Bis{bis(azido-κ<italic>N</italic>)bis[bis(pyridin-2-yl-κ<italic>N</italic>)amine]cobalt(III)} sulfate dihydrate</title><author><name sortKey="Setifi, Fatima" sort="Setifi, Fatima" uniqKey="Setifi F" first="Fatima" last="Setifi">Fatima Setifi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Knaust, Jacqueline M" sort="Knaust, Jacqueline M" uniqKey="Knaust J" first="Jacqueline M." last="Knaust">Jacqueline M. Knaust</name><affiliation><nlm:aff id="b">Department of Chemistry, Mathematics and Physics, Clarion University, 840 Wood Street, Clarion, PA 16214,<country>USA</country></nlm:aff></affiliation></author><author><name sortKey="Setifi, Zouaoui" sort="Setifi, Zouaoui" uniqKey="Setifi Z" first="Zouaoui" last="Setifi">Zouaoui Setifi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name><affiliation><nlm:aff id="c">Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, and, Faculté Pluridisciplinaire Nador BP 300, Selouane, 62702, Nador,<country>Morocco</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="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The crystal structure of bis{bis(azido-κ<italic>N</italic>)bis[bis(pyridin-2-yl-κ<italic>N</italic>)amine]cobalt(III)} sulfate dihydrate is comprised of discrete [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> cations, SO<sub>4</sub><sup>2−</sup> anions and solvent water molecules in a 2:1:2 ratio; extensive hydrogen-bonding interactions link the species into a three-dimensional supramolecular framework.</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><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><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">27375867</article-id><article-id pub-id-type="pmc">4910331</article-id><article-id pub-id-type="publisher-id">zl2656</article-id><article-id pub-id-type="doi">10.1107/S2056989016003662</article-id><article-id pub-id-type="coden">ACSECI</article-id><article-id pub-id-type="pii">S2056989016003662</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject></subj-group></article-categories><title-group><article-title>Bis{bis(azido-κ<italic>N</italic>)bis[bis(pyridin-2-yl-κ<italic>N</italic>)amine]cobalt(III)} sulfate dihydrate</article-title><alt-title><italic>[Co(N<sub>3</sub>)<sub>2</sub>(C<sub>10</sub>H<sub>9</sub>N<sub>3</sub>)<sub>2</sub>]<sub>2</sub>SO<sub>4</sub>·2H<sub>2</sub>O</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Setifi</surname><given-names>Fatima</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>Knaust</surname><given-names>Jacqueline M.</given-names></name><xref ref-type="aff" rid="b">b</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Setifi</surname><given-names>Zouaoui</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Touzani</surname><given-names>Rachid</given-names></name><xref ref-type="aff" rid="c">c</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Laboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000,<country>Algeria</country></aff><aff id="b"><label>b</label>Department of Chemistry, Mathematics and Physics, Clarion University, 840 Wood Street, Clarion, PA 16214,<country>USA</country></aff><aff id="c"><label>c</label>Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, and, Faculté Pluridisciplinaire Nador BP 300, Selouane, 62702, Nador,<country>Morocco</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>fat_setifi@yahoo.fr</email>, <email>jknaust@clarion.edu</email>, <email>touzanir@yahoo.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>4</month><year>2016</year></pub-date><pub-date pub-type="epub"><day>08</day><month>3</month><year>2016</year></pub-date><pub-date pub-type="pmc-release"><day>08</day><month>3</month><year>2016</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>72</volume><issue>Pt 4</issue><issue-id pub-id-type="publisher-id">e160400</issue-id><fpage>470</fpage><lpage>476</lpage><history><date date-type="received"><day>04</day><month>2</month><year>2016</year></date><date date-type="accepted"><day>02</day><month>3</month><year>2016</year></date></history><permissions><copyright-statement>© Setifi et al. 2016</copyright-statement><copyright-year>2016</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/S2056989016003662">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract abstract-type="toc"><p>The crystal structure of bis{bis(azido-κ<italic>N</italic>)bis[bis(pyridin-2-yl-κ<italic>N</italic>)amine]cobalt(III)} sulfate dihydrate is comprised of discrete [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> cations, SO<sub>4</sub><sup>2−</sup> anions and solvent water molecules in a 2:1:2 ratio; extensive hydrogen-bonding interactions link the species into a three-dimensional supramolecular framework.</p></abstract><abstract><p>The search for new molecular materials with interesting magnetic properties, using the pseudohalide azide ion and di-2-pyridylamine (dpa, C<sub>10</sub>H<sub>9</sub>N<sub>3</sub>) as a chelating ligand, led to the synthesis and structure determination of the title compound, [Co(N<sub>3</sub>)<sub>2</sub>(dpa)<sub>2</sub>]<sub>2</sub>SO<sub>4</sub>·2H<sub>2</sub>O. The crystal structure comprises discrete [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> cations, sulfate anions, as well as H<sub>2</sub>O solvent molecules. The Co<sup>III</sup> cations display a slightly distorted octahedral coordination sphere defined by two N atoms from azide anions and four N atoms from the pyridyl rings of two dpa ligands. In the crystal, extensive C—H⋯O, N—H⋯O, and O—H⋯O interactions result in supramolecular sheets that lie parallel to the <italic>ab</italic> plane. The sheets are further linked through O—H⋯N interactions between the water molecules of one sheet and azide anions of another sheet, forming a supramolecular framework.</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>coordination compound</kwd><kwd>Co<sup>III</sup> complex</kwd><kwd>di-2-pyridylamine (dpa)</kwd><kwd>azide</kwd><kwd>hydrogen bonding</kwd><kwd>supramolecular structure</kwd></kwd-group></article-meta></front><body><sec id="sec1"><title>Chemical context </title><p>In recent years, molecular magnetism has attracted great attention due to the interest in designing new molecular materials with interesting magnetic properties and potential applications (Kahn, 1993<xref ref-type="bibr" rid="bb17"> ▸</xref>; Miller & Gatteschi, 2011<xref ref-type="bibr" rid="bb20"> ▸</xref>). Connecting paramagnetic ions by use of bridging polynitrile or pseudohalide ligands is an important strategy in the design of such materials (Setifi <italic>et al.</italic>, 2002<xref ref-type="bibr" rid="bb27"> ▸</xref>, 2003<xref ref-type="bibr" rid="bb28"> ▸</xref>, 2013<xref ref-type="bibr" rid="bb29"> ▸</xref>, 2014<xref ref-type="bibr" rid="bb26"> ▸</xref>; Miyazaki <italic>et al.</italic>, 2003<xref ref-type="bibr" rid="bb21"> ▸</xref>; Benmansour <italic>et al.</italic>, 2008<xref ref-type="bibr" rid="bb2"> ▸</xref>, 2009<xref ref-type="bibr" rid="bb3"> ▸</xref>; Yuste <italic>et al.</italic>, 2009<xref ref-type="bibr" rid="bb35"> ▸</xref>). As a short bridging ligand and efficient superexchange mediator, the pseudohalide azide ion has proven to be very versatile and diverse in both coordination chemistry and magnetism. It can link metal ions in μ-1,1 (end-on, EO), μ-1,3 (end-to-end, EE) and μ-1,1,1 coordination modes among others, and effectively mediate either ferromagnetic or antiferromagnetic coupling. Many azide-bridged systems with different dimensionality and topology have been synthesized by using various auxiliary ligands, and a great diversity of magnetic behaviors have been demonstrated (Ribas <italic>et al.</italic>, 1999<xref ref-type="bibr" rid="bb24"> ▸</xref>; Gao <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb12"> ▸</xref>; Liu <italic>et al.</italic>, 2007<xref ref-type="bibr" rid="bb18"> ▸</xref>; Mautner <italic>et al.</italic>, 2010<xref ref-type="bibr" rid="bb19"> ▸</xref>). In view of the possible roles of the versatile azido ligand, we have been interested in using it in combination with other chelating or bridging neutral co-ligands to explore their structural and electronic characteristics in the field of molecular materials exhibiting interesting magnetic exchange coupling. During the course of attempts to prepare such complexes with di-2-pyridylamine, we isolated the title compound, whose structure is described herein.<chem-struct id="scheme1"><graphic xlink:href="e-72-00470-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec id="sec2"><title>Structural commentary </title><p>The structure of the title compound is composed of discrete [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> cations, SO<sub>4</sub><sup>2−</sup> anions, and solvent water molecules in a 2:1:2 ratio (Fig. 1<xref ref-type="fig" rid="fig1"> ▸</xref>). The sulfate anion is located on a twofold rotational axis, and all other atoms lie on general positions. The central Co<sup>III</sup> ion has an approximately octahedral coordination geometry formed by four N-donors from the pyridyl rings of two chelating bidentate dpa ligands and two N-donors from the terminal azide anions with the <italic>cisoid</italic> angles ranging from 84.97 (8) to 94.15 (8)° and <italic>transoid</italic> angles ranging from 174.02 (8) to 176.36 (8)° (Table 1<xref ref-type="table" rid="table1"> ▸</xref>). While the bite angles of the dpa ligands are both less than 90° the smallest <italic>cisoid</italic> angle observed is for N4—Co1—N10 (Table 1<xref ref-type="table" rid="table1"> ▸</xref>), and the pyridyl ring containing N4 and azide anion containing N10 are involved in a weak C—H⋯N interaction (C11—H11⋯N10) (Table 2<xref ref-type="table" rid="table2"> ▸</xref>). The two pyridyl rings of each chelating dpa ligand coordinate to the metal in a <italic>cis</italic>-disposition, and the azide anions are also coordinating <italic>cis</italic> to each other.</p><p>A similar arrangement of ligands is observed in four of the five transition metal compounds reported with coordination environments comprised of two chelating dpa ligands and two terminal azide anions [CSD refcodes: ATAFEG (Du <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb11"> ▸</xref>); EYOWEU (Villanueva <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb32"> ▸</xref>); HUFNUR (Du <italic>et al.</italic>, 2001<xref ref-type="bibr" rid="bb10"> ▸</xref>); JANPOE (Bose <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb4"> ▸</xref>); ATAFEG01 and EYOWEU01 (Rahaman <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb23"> ▸</xref>)]; in the fifth compound, [Cu(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]·2H<sub>2</sub>O, the two pyridyl rings of each chelating dpa ligand still coordinate to the metal in a <italic>cis</italic>-disposition, but the azide anions are coordinated <italic>trans</italic> to each other [CSD refcode: XUYWIX (Du <italic>et al.</italic>, 2003<xref ref-type="bibr" rid="bb9"> ▸</xref>)]. The six Co—N bond lengths are comparable to those observed in [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]ClO<sub>4</sub> [CSD refcode; HUFNUR; Du <italic>et al.</italic>, 2001<xref ref-type="bibr" rid="bb10"> ▸</xref>)] and range from 1.9334 (18) to 1.9699 (17) Å with a mean bond length of 1.955 Å (Table 1<xref ref-type="table" rid="table1"> ▸</xref>). Both of the coordinating azide anions are nearly linear with N—N—N bond angles of 175.7 (2) and 175.3 (3)° for N7—N8—N9 and N10—N11—N12, respectively (Table 1<xref ref-type="table" rid="table1"> ▸</xref>). Not unexpectedly, the Co1—N7—N8 and Co1—N10—N11 bond angles are 122.05 (15) and 126.09 (17)°, respectively, and the N—N bond lengths are slightly longer for the bonds involving nitrogen atoms coordinating to the Co<sup>III</sup> ion at 1.208 (3) and 1.181 (2) Å for N7—N8 and N10—N11, respectively, <italic>versus</italic> 1.142 (3) and 1.148 (3) Å for N8—N9 and N11—N12, respectively (Dori & Ziolo, 1973<xref ref-type="bibr" rid="bb8"> ▸</xref>) (Table 1<xref ref-type="table" rid="table1"> ▸</xref>).</p><p>Three conformations are known for dpa, <italic>cis–cis</italic>, <italic>cis–trans</italic>, or <italic>trans–trans</italic> (Fig. 2<xref ref-type="fig" rid="fig2"> ▸</xref>); <italic>cis</italic> and <italic>trans</italic> refer to the relation of the pyridyl nitrogen atoms to the amine nitrogen (Gornitzka & Stalke, 1998<xref ref-type="bibr" rid="bb13"> ▸</xref>). Several bonding modes are possible involving just the pyridyl nitrogen atoms (Fig. 3<xref ref-type="fig" rid="fig3"> ▸</xref>). Only bonding modes <bold>I</bold>–<bold>II</bold> and <bold>IV–VI</bold> are observed for dpa with transition metals, but additional bonding modes are possible for anionic dpa involving coordination <italic>via</italic> the amide nitrogen, and there are also a few reports of coordination at the deprotonated <italic>ortho</italic> carbon of one of the pyridyl rings (Brogden & Berry, 2016<xref ref-type="bibr" rid="bb5"> ▸</xref>). In the title compound, as in the vast majority of structures where neutral dpa coordinates to a transition metal (see <italic>Database Survey</italic>), dpa adopts the <italic>trans–trans</italic> conformation and acts as a chelating ligand in bonding mode <bold>VI</bold>. The flexible nature of the dpa ligand is well recognized (Carranza <italic>et al.</italic>, 2008<xref ref-type="bibr" rid="bb7"> ▸</xref>; Du <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb11"> ▸</xref>; Wang <italic>et al.</italic>, 2009<xref ref-type="bibr" rid="bb33"> ▸</xref>), and as is often observed for coordinating dpa ligands, each dpa ligand in the title complex is quite distorted from planarity due to folding of the pyridyl rings about the line connecting the amino nitrogen atom and the metal cation with a 46.18 (5)° angle between plane 1 (defined by atoms Co1/N1/C1–C5/N2) and plane 2 (defined by atoms N2/C6–C10/N3/Co1) and a 37.40 (6)° angle between plane 3 (defined by atoms Co1/N4/C11–C15/N5) and plane 4 (defined by atoms N5/C16–C20/N6/Co1) (Table 3<xref ref-type="table" rid="table3"> ▸</xref>). For dpa ligands coordinating to a metal atom <italic>via</italic> bonding mode <bold>VI</bold>, a wide range of pyridine centroid–amine nitrogen–pyridine centroid (Py<sub>cent</sub>—N<sub>a</sub>—Py<sub>cent</sub>) angles and pyridine nitrogen–metal–pyridine nitrogen (N<sub>py</sub>—<italic>M</italic>—N<sub>py</sub>) bite angles are reported, but no simple trend between the two angles is observed (Brogden & Berry, 2016<xref ref-type="bibr" rid="bb5"> ▸</xref>).</p><p>In [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup>, the Py1<sub>cent</sub>—N<sub>2</sub>—Py3<sub>cent</sub> and N1—Co1—N3 angles are 120.92 (7) and 86.48 (7)°, and the Py4<sub>cent</sub>—N5—Py5<sub>cent</sub> and N4—Co1—N6 angles are 125.49 (7) and 88.08 (7)° (Py1, Py3, Py4, and Py6 are the pyridyl rings containing N1, N3, N4, and N6 respectively) (Table 1<xref ref-type="table" rid="table1"> ▸</xref>). The C—N—C angles around the amino nitrogen are larger than expected for a trigonal planar nitrogen atom at 123.44 (17)° for C5—N2—C6 and 125.87 (19)° for C15—N5—C16, but N—C—N angles at the ring junctions are closer to 120° [N1—C5—N2 = 119.38 (18)°; N2—C6—N3 = 119.1 (2)°; N4—C15—N5 = 119.30 (18)°; N5—C16—N6 = 120.16 (18)°], and the metal lies less than 2.5° from the lone-pair direction for each pyridyl nitrogen atom [C5—N1—Co1 = 120.94 (14); C6—N3—Co1 = 120.49 (14); C15—N4—Co1=122.47 (15); C16—N6—Co1 = 121.35 (13)°; Table 1<xref ref-type="table" rid="table1"> ▸</xref>]. Both of the dpa ligands form six-membered chelate rings with boat conformations. For chelate ring –Co1–N1–C5–N2–C6–N3–, atoms Co1 and N2 lie 0.868 (3) and 0.336 (3) Å below the mean plane defined by atoms N1/C5/C6/N3, and for chelate ring –Co–N4–C15–N5–C16–N6–, atoms Co1 and N5 lie 0.770 (3) and 0.278 (3) Å above the mean plane defined by atoms N4/C15/C16/N6 (Table 3<xref ref-type="table" rid="table3"> ▸</xref>).</p></sec><sec id="sec3"><title>Supramolecular features </title><p>Stabilizing C—H⋯N interactions (C11—H11⋯N10, C20—H20⋯N7, C20—H20⋯N11) are observed between neighboring dpa ligands and azide anions within the coordination sphere of the Co<sup>III</sup> cation (Table 2<xref ref-type="table" rid="table2"> ▸</xref>). The complex cations and water molecules aggregate into layers parallel to the <italic>ab</italic> plane, and each [Co(C<sub>10</sub>H<sub>9</sub>H<sub>3</sub>)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> complex cation interacts with one water molecule through a C—H⋯O hydrogen bond (C10—H10⋯O3). The sulfate anions are sandwiched between two symmetry-related layers of complex cations and water molecules (Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>). Each sulfate anion interacts with two water molecules and four [Co(C<sub>10</sub>H<sub>9</sub>H<sub>3</sub>)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> cations through twelve hydrogen bonds (Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>). As the sulfate anion is located on a twofold rotational axis, only six of the twelve hydrogen bonds are unique (O3—H3<italic>A</italic>⋯O2<sup>ii</sup>, N2—H2<italic>N</italic>⋯O2<sup>iii</sup>, N5—H5<italic>N</italic>⋯O1, C4—H4⋯O2<sup>iii</sup>, C14—H14⋯O1<sup>iv</sup>, and C17—H17⋯O1). The extensive C—H⋯O, N—H⋯O, and O—H⋯O interactions result in two-dimensional supramolecular sheets parallel to the <italic>ab</italic> plane (Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>). Finally, the sheets are linked <italic>via</italic> O—H⋯N interactions between the water molecules of one sheet and the azide anions of another sheet (O3—H3<italic>B</italic>⋯N12<sup>i</sup>), forming a supramolecular framework (Fig. 6<xref ref-type="fig" rid="fig6"> ▸</xref>).</p></sec><sec id="sec4"><title>Database survey </title><p>Free dpa crystallizes as one of several polymorphs, but only in the <italic>cis–trans</italic> conformation with an intramolecular C—H⋯N hydrogen bond between the two pyridyl rings [CSD refcodes: DPYRAM (Johnson & Jacobson, 1973<xref ref-type="bibr" rid="bb16"> ▸</xref>); DPYRAM01 (Pyrka & Pinkerton, 1992<xref ref-type="bibr" rid="bb22"> ▸</xref>); DPYRAM03 and DPYRAM04 (Schödel <italic>et al.</italic>, 1996<xref ref-type="bibr" rid="bb25"> ▸</xref>)]. Theoretical calculations by Wu <italic>et al.</italic> (2013<xref ref-type="bibr" rid="bb34"> ▸</xref>) give the <italic>cis–trans</italic> conformation at 2.5 and 8.0. kcal mol<sup>−1</sup> more stable than the <italic>cis–cis</italic> and <italic>trans–trans</italic> conformations, respectively, and the authors suggest that the instability of free dpa in the <italic>trans–trans</italic> conformation is due to repulsive interactions between of the pyridyl nitrogen lone pairs. However, when dpa coordinates to a transition metal, the <italic>trans–trans</italic> conformation is preferred. A survey of the Cambridge Structural Database (CSD; Groom & Allen, 2014<xref ref-type="bibr" rid="bb14"> ▸</xref>) returned 735 hits for structures involving a dpa ligand coordinating to a transition metal cation <italic>via</italic> at least one of its pyridyl rings (structures involving anionic dpa and coordination to a metal <italic>via</italic> the amide nitrogen were excluded from the search). Of the 735 hits, only 15 structures involve dpa acting as a monodentate ligand in either the <italic>cis–cis</italic> or <italic>cis–trans</italic> conformations (bonding modes <bold>I</bold> and <bold>II</bold>, respectively) are reported. Dpa acts as a bridging ligand in only three structures in either the <italic>cis–cis</italic> or <italic>cis–trans</italic> conformations (bonding modes <bold>IV</bold> and <bold>V</bold>, respectively). No structures are observed with dpa in bonding mode <bold>III</bold>. In the remainder of the structures, dpa adopts the <italic>trans–trans</italic> conformation and acts as a chelating ligand in bonding mode <bold>VI</bold>.</p><p>As mentioned in the <italic>Structural commentary</italic>, dpa is a flexible ligand and adopts a wide range of Py<sub>cent</sub>—N<sub>a</sub>—Py<sub>cent</sub> and N<sub>py</sub>—<italic>M</italic>—N<sub>py</sub> bite angles in transition metal complexes. A comparison of these angles in the title compound to those observed in all structures reported to the CSD involving dpa coordinating to a transition metal in bonding mode <bold>VI</bold> reveals no simple trend (Brogden & Berry, 2016<xref ref-type="bibr" rid="bb5"> ▸</xref>) (Fig. 7<xref ref-type="fig" rid="fig7"> ▸</xref>). Comparison of the folding angle about N<sub>a</sub>—<italic>M</italic> versus the N<sub>py</sub>—<italic>M</italic>—N<sub>py</sub> bite angle (Fig. 8<xref ref-type="fig" rid="fig8"> ▸</xref>) as well as the folding angle about N<sub>a</sub>—<italic>M versus</italic> the mean N<sub>py</sub>—M distance (Fig. 9<xref ref-type="fig" rid="fig9"> ▸</xref>) in the title compound to those observed in all structures reported to the CSD involving dpa coordinating to a transition metal in bonding mode <bold>VI</bold> also supports the flexible nature of dpa as a chelating ligand; however, no simple trend between the folding angle and the bite angle or the folding angle and the mean N<sub>py</sub>—<italic>M</italic> distance is indicated.</p><p>A more narrow search for structures involving at least one terminal azide anion and one dpa ligand in bonding mode <bold>VI</bold> within the coordination sphere of a transition metal cation returned 30 hits for 25 unique structures. Of the 25 structures, 23 involve <italic>M</italic><sup>II</sup> cations; there is one report for Co<sup>III</sup> [CSD refcode: HUFNUR (Du <italic>et al.</italic>, 2001<xref ref-type="bibr" rid="bb10"> ▸</xref>)] and another report for Pt<sup>IV</sup>[CSD refcode: YATYOJ (Ha, 2012<xref ref-type="bibr" rid="bb15"> ▸</xref>)]. Five structures are reported where the metal cation has a coordination sphere similar to that of the title compound. In each case, an approximately octahedral coordination geometry is formed by four N-donors from the pyridyl rings of two dpa ligands and two N-donors from terminal azide anions. In [<italic>M</italic>(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]·H<sub>2</sub>O with <italic>M</italic> = Mn [CSD refcode: JANPOE (Bose <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb4"> ▸</xref>)], Ni [CSD refcodes: EYOWEU (Villanueva <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb32"> ▸</xref>) and EYOWEU01 (Rahaman <italic>et al.</italic> 2005<xref ref-type="bibr" rid="bb23"> ▸</xref>)], and Zn [CSD refcodes: ATAFEG (Du <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb11"> ▸</xref>) and ATAFEG01 (Rahaman <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb23"> ▸</xref>)], neutral complexes are observed. In each case, the azide anions coordinate to the metal cation in a <italic>cis</italic>-fashion, and hydrogen bonding, face-to-face π–π stacking, and edge-to-face C–H⋯π interactions result in a three-dimensional supramolecular framework. In [Cu(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]·2H<sub>2</sub>O, the azide anions coordinate to the Cu<sup>II</sup> ion weakly in a <italic>trans</italic>-fashion, resulting in a tetragonally elongated octahedral coordination sphere for the Cu<sup>II</sup> ion, and hydrogen bonding and face-to-face π–π stacking interactions result in two-dimensional supramolecular sheets that lie parallel to the <italic>bc</italic>-plane [CSD refcode: XUYWIX (Du <italic>et al.</italic>, 2003<xref ref-type="bibr" rid="bb9"> ▸</xref>)]. [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]ClO<sub>4</sub> is most closely related to the title complex in that the Co<sup>III</sup> ions are coordinated by two chelating dpa ligands and two azide anions in a <italic>cis</italic>-fashion to form [Co(dpa)<sub>2</sub>(N<sub>3</sub>)<sub>2</sub>]<sup>+</sup> complex cations [CSD refcode: HUFNUR (Du <italic>et al.</italic>, 2001<xref ref-type="bibr" rid="bb10"> ▸</xref>)]. The structure is stabilized by strong N—H⋯O interactions between the complex cation and perchlorate anions. Consideration of additional weak C—H⋯N interactions between the cations (which were not discussed by the authors) results in supramolecular ribbons that run parallel to the <italic>c</italic> axis.</p></sec><sec id="sec5"><title>Synthesis and crystallization </title><p>The title compound was synthesized hydrothermally under autogenous pressure from a mixture of cobalt(II) sulfate heptahydrate (28 mg, 0.1 mmol), di-2-pyridylamine (17 mg, 0.1 mmol) and sodium azide NaN<sub>3</sub> (13 mg, 0.2 mmol) in water–methanol (4:1 <italic>v</italic>/<italic>v</italic>, 20 ml). The mixture was sealed in a Teflon-lined autoclave and heated at 423 K for two days and cooled to room temperature at 10 K h<sup>−1</sup>. The crystals were obtained in <italic>ca</italic> 20% yield based on cobalt.</p><p><italic><bold>CAUTION!</bold></italic> Although not encountered in our experiments, azido compounds of metal ions are potentially explosive. Only a small amount of the materials should be prepared, and it should be handled with care.</p></sec><sec id="sec6"><title>Refinement </title><p>Crystal data, data collection and structure refinement details are summarized in Table 4<xref ref-type="table" rid="table4"> ▸</xref>. All aromatic H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C). The N—H and O—H-atoms were located in difference Fourier maps and then refined as riding on the carrying nitrogen or oxygen atom with <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(N) or <italic>U</italic><sub>iso</sub>(H) = 1.5<italic>U</italic><sub>eq</sub>(O). Two reflections considered to be affected by beam stop interference, 0 0 2 and 2 0 0, were omitted from the refinement.</p></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S2056989016003662/zl2656sup1.cif">10.1107/S2056989016003662/zl2656sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-72-00470-sup1.cif" xlink:type="simple" id="d36e171" 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/S2056989016003662/zl2656Isup2.hkl">10.1107/S2056989016003662/zl2656Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-72-00470-Isup2.hkl" xlink:type="simple" id="d36e178" position="anchor"></media></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=1457112">1457112</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?zl2656&file=zl2656sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?zl2656sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?zl2656&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><ack><p>The authors acknowledge the Algerian agency MESRS (Ministère de l’Enseignement Supérieur et de la Recherche Scientifique), the DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique), as well as the Université Ferhat Abbas Sétif 1 and Clarion University for financial support.</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">[Co(N<sub>3</sub>)<sub>2</sub>(C<sub>10</sub>H<sub>9</sub>N<sub>3</sub>)<sub>2</sub>]<sub>2</sub>SO<sub>4</sub>·2H<sub>2</sub>O</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 2264</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 1102.88</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.560 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>C</italic>2/<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"><italic>a</italic> = 19.9014 (4) Å</td><td rowspan="1" colspan="1">Cell parameters from 7924 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 8.7044 (2) Å</td><td rowspan="1" colspan="1">θ = 2.5–24.6°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 27.1181 (5) Å</td><td rowspan="1" colspan="1">µ = 0.83 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 90.753 (1)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 293 K</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 4697.25 (17) Å<sup>3</sup></td><td rowspan="1" colspan="1">Block, red</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 4</td><td rowspan="1" colspan="1">0.26 × 0.17 × 0.09 mm</td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e176"><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 APEXII CCD diffractometer</td><td rowspan="1" colspan="1">6893 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: sealed tube</td><td rowspan="1" colspan="1">3940 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> = 0.096</td></tr><tr><td rowspan="1" colspan="1">φ and ω scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 30.1°, θ<sub>min</sub> = 2.5°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2009)</td><td rowspan="1" colspan="1"><italic>h</italic> = −28→28</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.808, <italic>T</italic><sub>max</sub> = 0.875</td><td rowspan="1" colspan="1"><italic>k</italic> = −12→12</td></tr><tr><td rowspan="1" colspan="1">50250 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −38→38</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e293"><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">0 restraints</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Hydrogen site location: mixed</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.043</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.094</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0412<italic>P</italic>)<sup>2</sup>] where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 0.90</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.001</td></tr><tr><td rowspan="1" colspan="1">6893 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.49 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">331 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.52 e Å<sup>−</sup><sup>3</sup></td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e443"><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="d1e464"><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">Co1</td><td rowspan="1" colspan="1">0.62803 (2)</td><td rowspan="1" colspan="1">0.08164 (3)</td><td rowspan="1" colspan="1">0.07843 (2)</td><td rowspan="1" colspan="1">0.02579 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.5000</td><td rowspan="1" colspan="1">0.58900 (9)</td><td rowspan="1" colspan="1">0.2500</td><td rowspan="1" colspan="1">0.0362 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.55892 (9)</td><td rowspan="1" colspan="1">0.4950 (2)</td><td rowspan="1" colspan="1">0.24043 (8)</td><td rowspan="1" colspan="1">0.0631 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.48452 (10)</td><td rowspan="1" colspan="1">0.6853 (3)</td><td rowspan="1" colspan="1">0.20752 (7)</td><td rowspan="1" colspan="1">0.0753 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.86029 (11)</td><td rowspan="1" colspan="1">0.2512 (3)</td><td rowspan="1" colspan="1">0.15996 (8)</td><td rowspan="1" colspan="1">0.0925 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3A</td><td rowspan="1" colspan="1">0.8961</td><td rowspan="1" colspan="1">0.2070</td><td rowspan="1" colspan="1">0.1708</td><td rowspan="1" colspan="1">0.139*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3B</td><td rowspan="1" colspan="1">0.8603</td><td rowspan="1" colspan="1">0.2324</td><td rowspan="1" colspan="1">0.1289</td><td rowspan="1" colspan="1">0.139*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.60151 (9)</td><td rowspan="1" colspan="1">−0.13172 (19)</td><td rowspan="1" colspan="1">0.06724 (7)</td><td rowspan="1" colspan="1">0.0277 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.57170 (9)</td><td rowspan="1" colspan="1">−0.1581 (2)</td><td rowspan="1" colspan="1">0.15044 (7)</td><td rowspan="1" colspan="1">0.0316 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2N</td><td rowspan="1" colspan="1">0.5366</td><td rowspan="1" colspan="1">−0.1727</td><td rowspan="1" colspan="1">0.1680</td><td rowspan="1" colspan="1">0.038*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.66233 (8)</td><td rowspan="1" colspan="1">0.01273 (19)</td><td rowspan="1" colspan="1">0.14314 (6)</td><td rowspan="1" colspan="1">0.0263 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.53936 (9)</td><td rowspan="1" colspan="1">0.13277 (19)</td><td rowspan="1" colspan="1">0.10540 (7)</td><td rowspan="1" colspan="1">0.0282 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.58666 (9)</td><td rowspan="1" colspan="1">0.30108 (19)</td><td rowspan="1" colspan="1">0.16366 (7)</td><td rowspan="1" colspan="1">0.0323 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5N</td><td rowspan="1" colspan="1">0.5886</td><td rowspan="1" colspan="1">0.3159</td><td rowspan="1" colspan="1">0.1950</td><td rowspan="1" colspan="1">0.039*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.65632 (8)</td><td rowspan="1" colspan="1">0.29126 (18)</td><td rowspan="1" colspan="1">0.09387 (7)</td><td rowspan="1" colspan="1">0.0274 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.71278 (10)</td><td rowspan="1" colspan="1">0.0457 (2)</td><td rowspan="1" colspan="1">0.04634 (7)</td><td rowspan="1" colspan="1">0.0374 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N8</td><td rowspan="1" colspan="1">0.75070 (10)</td><td rowspan="1" colspan="1">−0.0551 (2)</td><td rowspan="1" colspan="1">0.05942 (8)</td><td rowspan="1" colspan="1">0.0404 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N9</td><td rowspan="1" colspan="1">0.78932 (12)</td><td rowspan="1" colspan="1">−0.1472 (3)</td><td rowspan="1" colspan="1">0.06960 (11)</td><td rowspan="1" colspan="1">0.0730 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N10</td><td rowspan="1" colspan="1">0.58775 (10)</td><td rowspan="1" colspan="1">0.1370 (2)</td><td rowspan="1" colspan="1">0.01490 (8)</td><td rowspan="1" colspan="1">0.0420 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N11</td><td rowspan="1" colspan="1">0.61222 (10)</td><td rowspan="1" colspan="1">0.2161 (2)</td><td rowspan="1" colspan="1">−0.01536 (8)</td><td rowspan="1" colspan="1">0.0369 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N12</td><td rowspan="1" colspan="1">0.63226 (14)</td><td rowspan="1" colspan="1">0.2907 (3)</td><td rowspan="1" colspan="1">−0.04682 (10)</td><td rowspan="1" colspan="1">0.0783 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.60855 (11)</td><td rowspan="1" colspan="1">−0.1984 (3)</td><td rowspan="1" colspan="1">0.02241 (9)</td><td rowspan="1" colspan="1">0.0356 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.6312</td><td rowspan="1" colspan="1">−0.1445</td><td rowspan="1" colspan="1">−0.0019</td><td rowspan="1" colspan="1">0.043*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.58399 (12)</td><td rowspan="1" colspan="1">−0.3408 (3)</td><td rowspan="1" colspan="1">0.01124 (9)</td><td rowspan="1" colspan="1">0.0394 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.5908</td><td rowspan="1" colspan="1">−0.3845</td><td rowspan="1" colspan="1">−0.0196</td><td rowspan="1" colspan="1">0.047*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.54857 (12)</td><td rowspan="1" colspan="1">−0.4186 (3)</td><td rowspan="1" colspan="1">0.04718 (10)</td><td rowspan="1" colspan="1">0.0418 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.5298</td><td rowspan="1" colspan="1">−0.5141</td><td rowspan="1" colspan="1">0.0402</td><td rowspan="1" colspan="1">0.050*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.54117 (11)</td><td rowspan="1" colspan="1">−0.3552 (3)</td><td rowspan="1" colspan="1">0.09263 (9)</td><td rowspan="1" colspan="1">0.0354 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.5165</td><td rowspan="1" colspan="1">−0.4054</td><td rowspan="1" colspan="1">0.1166</td><td rowspan="1" colspan="1">0.042*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.57136 (10)</td><td rowspan="1" colspan="1">−0.2132 (2)</td><td rowspan="1" colspan="1">0.10264 (8)</td><td rowspan="1" colspan="1">0.0276 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.62535 (11)</td><td rowspan="1" colspan="1">−0.0810 (2)</td><td rowspan="1" colspan="1">0.17145 (8)</td><td rowspan="1" colspan="1">0.0292 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.64101 (14)</td><td rowspan="1" colspan="1">−0.1050 (3)</td><td rowspan="1" colspan="1">0.22072 (9)</td><td rowspan="1" colspan="1">0.0443 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.6126</td><td rowspan="1" colspan="1">−0.1632</td><td rowspan="1" colspan="1">0.2403</td><td rowspan="1" colspan="1">0.053*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.69828 (15)</td><td rowspan="1" colspan="1">−0.0430 (3)</td><td rowspan="1" colspan="1">0.24052 (10)</td><td rowspan="1" colspan="1">0.0560 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">0.7092</td><td rowspan="1" colspan="1">−0.0582</td><td rowspan="1" colspan="1">0.2736</td><td rowspan="1" colspan="1">0.067*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.74015 (13)</td><td rowspan="1" colspan="1">0.0436 (3)</td><td rowspan="1" colspan="1">0.21047 (10)</td><td rowspan="1" colspan="1">0.0492 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">0.7806</td><td rowspan="1" colspan="1">0.0827</td><td rowspan="1" colspan="1">0.2226</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.72045 (11)</td><td rowspan="1" colspan="1">0.0694 (2)</td><td rowspan="1" colspan="1">0.16294 (9)</td><td rowspan="1" colspan="1">0.0357 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">0.7480</td><td rowspan="1" colspan="1">0.1287</td><td rowspan="1" colspan="1">0.1430</td><td rowspan="1" colspan="1">0.043*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.48315 (11)</td><td rowspan="1" colspan="1">0.0676 (2)</td><td rowspan="1" colspan="1">0.08557 (9)</td><td rowspan="1" colspan="1">0.0364 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">0.4870</td><td rowspan="1" colspan="1">0.0131</td><td rowspan="1" colspan="1">0.0562</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.42166 (12)</td><td rowspan="1" colspan="1">0.0780 (3)</td><td rowspan="1" colspan="1">0.10643 (11)</td><td rowspan="1" colspan="1">0.0476 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.3844</td><td rowspan="1" colspan="1">0.0307</td><td rowspan="1" colspan="1">0.0920</td><td rowspan="1" colspan="1">0.057*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.41593 (13)</td><td rowspan="1" colspan="1">0.1606 (3)</td><td rowspan="1" colspan="1">0.14953 (11)</td><td rowspan="1" colspan="1">0.0590 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.3748</td><td rowspan="1" colspan="1">0.1660</td><td rowspan="1" colspan="1">0.1653</td><td rowspan="1" colspan="1">0.071*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.47057 (12)</td><td rowspan="1" colspan="1">0.2342 (3)</td><td rowspan="1" colspan="1">0.16911 (10)</td><td rowspan="1" colspan="1">0.0494 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">0.4669</td><td rowspan="1" colspan="1">0.2927</td><td rowspan="1" colspan="1">0.1976</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.53216 (11)</td><td rowspan="1" colspan="1">0.2201 (2)</td><td rowspan="1" colspan="1">0.14548 (9)</td><td rowspan="1" colspan="1">0.0323 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.63826 (10)</td><td rowspan="1" colspan="1">0.3604 (2)</td><td rowspan="1" colspan="1">0.13612 (8)</td><td rowspan="1" colspan="1">0.0277 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.67037 (11)</td><td rowspan="1" colspan="1">0.4937 (2)</td><td rowspan="1" colspan="1">0.15335 (9)</td><td rowspan="1" colspan="1">0.0343 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17</td><td rowspan="1" colspan="1">0.6599</td><td rowspan="1" colspan="1">0.5344</td><td rowspan="1" colspan="1">0.1840</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.71738 (11)</td><td rowspan="1" colspan="1">0.5632 (2)</td><td rowspan="1" colspan="1">0.12447 (10)</td><td rowspan="1" colspan="1">0.0382 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">0.7391</td><td rowspan="1" colspan="1">0.6519</td><td rowspan="1" colspan="1">0.1352</td><td rowspan="1" colspan="1">0.046*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.73217 (11)</td><td rowspan="1" colspan="1">0.5000 (3)</td><td rowspan="1" colspan="1">0.07916 (9)</td><td rowspan="1" colspan="1">0.0378 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">0.7620</td><td rowspan="1" colspan="1">0.5487</td><td rowspan="1" colspan="1">0.0582</td><td rowspan="1" colspan="1">0.045*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.70238 (11)</td><td rowspan="1" colspan="1">0.3651 (2)</td><td rowspan="1" colspan="1">0.06560 (9)</td><td rowspan="1" colspan="1">0.0331 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H20</td><td rowspan="1" colspan="1">0.7140</td><td rowspan="1" colspan="1">0.3213</td><td rowspan="1" colspan="1">0.0356</td><td rowspan="1" colspan="1">0.040*</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e1235"><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">Co1</td><td rowspan="1" colspan="1">0.02576 (15)</td><td rowspan="1" colspan="1">0.02659 (15)</td><td rowspan="1" colspan="1">0.02507 (17)</td><td rowspan="1" colspan="1">−0.00383 (12)</td><td rowspan="1" colspan="1">0.00259 (12)</td><td rowspan="1" colspan="1">0.00118 (13)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.0488 (5)</td><td rowspan="1" colspan="1">0.0334 (4)</td><td rowspan="1" colspan="1">0.0268 (5)</td><td rowspan="1" colspan="1">0.000</td><td rowspan="1" colspan="1">0.0147 (4)</td><td rowspan="1" colspan="1">0.000</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0534 (12)</td><td rowspan="1" colspan="1">0.0569 (11)</td><td rowspan="1" colspan="1">0.0795 (16)</td><td rowspan="1" colspan="1">0.0011 (9)</td><td rowspan="1" colspan="1">0.0266 (11)</td><td rowspan="1" colspan="1">−0.0322 (11)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0638 (13)</td><td rowspan="1" colspan="1">0.1057 (17)</td><td rowspan="1" colspan="1">0.0562 (14)</td><td rowspan="1" colspan="1">−0.0388 (12)</td><td rowspan="1" colspan="1">−0.0109 (11)</td><td rowspan="1" colspan="1">0.0498 (12)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0682 (15)</td><td rowspan="1" colspan="1">0.146 (2)</td><td rowspan="1" colspan="1">0.0629 (16)</td><td rowspan="1" colspan="1">−0.0251 (15)</td><td rowspan="1" colspan="1">0.0010 (13)</td><td rowspan="1" colspan="1">0.0020 (15)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0285 (9)</td><td rowspan="1" colspan="1">0.0291 (9)</td><td rowspan="1" colspan="1">0.0254 (11)</td><td rowspan="1" colspan="1">−0.0028 (8)</td><td rowspan="1" colspan="1">0.0012 (8)</td><td rowspan="1" colspan="1">−0.0009 (8)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0323 (10)</td><td rowspan="1" colspan="1">0.0350 (10)</td><td rowspan="1" colspan="1">0.0276 (11)</td><td rowspan="1" colspan="1">−0.0087 (8)</td><td rowspan="1" colspan="1">0.0047 (8)</td><td rowspan="1" colspan="1">0.0016 (8)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0266 (9)</td><td rowspan="1" colspan="1">0.0248 (9)</td><td rowspan="1" colspan="1">0.0276 (11)</td><td rowspan="1" colspan="1">−0.0034 (7)</td><td rowspan="1" colspan="1">0.0005 (8)</td><td rowspan="1" colspan="1">−0.0003 (8)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0270 (10)</td><td rowspan="1" colspan="1">0.0284 (9)</td><td rowspan="1" colspan="1">0.0291 (11)</td><td rowspan="1" colspan="1">−0.0031 (8)</td><td rowspan="1" colspan="1">−0.0007 (8)</td><td rowspan="1" colspan="1">0.0026 (8)</td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.0343 (10)</td><td rowspan="1" colspan="1">0.0355 (10)</td><td rowspan="1" colspan="1">0.0272 (11)</td><td rowspan="1" colspan="1">−0.0066 (8)</td><td rowspan="1" colspan="1">0.0077 (9)</td><td rowspan="1" colspan="1">−0.0044 (8)</td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.0267 (9)</td><td rowspan="1" colspan="1">0.0274 (9)</td><td rowspan="1" colspan="1">0.0281 (11)</td><td rowspan="1" colspan="1">−0.0018 (7)</td><td rowspan="1" colspan="1">0.0037 (8)</td><td rowspan="1" colspan="1">0.0028 (8)</td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.0351 (11)</td><td rowspan="1" colspan="1">0.0390 (11)</td><td rowspan="1" colspan="1">0.0384 (13)</td><td rowspan="1" colspan="1">−0.0021 (9)</td><td rowspan="1" colspan="1">0.0121 (10)</td><td rowspan="1" colspan="1">−0.0002 (9)</td></tr><tr><td rowspan="1" colspan="1">N8</td><td rowspan="1" colspan="1">0.0339 (11)</td><td rowspan="1" colspan="1">0.0355 (11)</td><td rowspan="1" colspan="1">0.0522 (14)</td><td rowspan="1" colspan="1">−0.0056 (10)</td><td rowspan="1" colspan="1">0.0186 (10)</td><td rowspan="1" colspan="1">−0.0002 (10)</td></tr><tr><td rowspan="1" colspan="1">N9</td><td rowspan="1" colspan="1">0.0521 (15)</td><td rowspan="1" colspan="1">0.0533 (14)</td><td rowspan="1" colspan="1">0.114 (2)</td><td rowspan="1" colspan="1">0.0157 (13)</td><td rowspan="1" colspan="1">0.0311 (16)</td><td rowspan="1" colspan="1">0.0267 (15)</td></tr><tr><td rowspan="1" colspan="1">N10</td><td rowspan="1" colspan="1">0.0423 (12)</td><td rowspan="1" colspan="1">0.0517 (12)</td><td rowspan="1" colspan="1">0.0319 (12)</td><td rowspan="1" colspan="1">−0.0151 (10)</td><td rowspan="1" colspan="1">−0.0032 (10)</td><td rowspan="1" colspan="1">0.0126 (10)</td></tr><tr><td rowspan="1" colspan="1">N11</td><td rowspan="1" colspan="1">0.0403 (11)</td><td rowspan="1" colspan="1">0.0410 (11)</td><td rowspan="1" colspan="1">0.0293 (12)</td><td rowspan="1" colspan="1">−0.0046 (9)</td><td rowspan="1" colspan="1">−0.0040 (10)</td><td rowspan="1" colspan="1">−0.0013 (10)</td></tr><tr><td rowspan="1" colspan="1">N12</td><td rowspan="1" colspan="1">0.0860 (19)</td><td rowspan="1" colspan="1">0.102 (2)</td><td rowspan="1" colspan="1">0.0463 (16)</td><td rowspan="1" colspan="1">−0.0462 (17)</td><td rowspan="1" colspan="1">−0.0125 (14)</td><td rowspan="1" colspan="1">0.0355 (15)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0356 (13)</td><td rowspan="1" colspan="1">0.0394 (13)</td><td rowspan="1" colspan="1">0.0319 (14)</td><td rowspan="1" colspan="1">−0.0042 (10)</td><td rowspan="1" colspan="1">0.0025 (11)</td><td rowspan="1" colspan="1">−0.0033 (11)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0410 (14)</td><td rowspan="1" colspan="1">0.0396 (13)</td><td rowspan="1" colspan="1">0.0376 (15)</td><td rowspan="1" colspan="1">−0.0036 (11)</td><td rowspan="1" colspan="1">−0.0032 (12)</td><td rowspan="1" colspan="1">−0.0133 (11)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0437 (14)</td><td rowspan="1" colspan="1">0.0332 (12)</td><td rowspan="1" colspan="1">0.0483 (17)</td><td rowspan="1" colspan="1">−0.0081 (11)</td><td rowspan="1" colspan="1">−0.0124 (12)</td><td rowspan="1" colspan="1">−0.0067 (12)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0349 (13)</td><td rowspan="1" colspan="1">0.0337 (12)</td><td rowspan="1" colspan="1">0.0376 (15)</td><td rowspan="1" colspan="1">−0.0071 (10)</td><td rowspan="1" colspan="1">−0.0034 (11)</td><td rowspan="1" colspan="1">0.0039 (11)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0264 (11)</td><td rowspan="1" colspan="1">0.0271 (11)</td><td rowspan="1" colspan="1">0.0291 (13)</td><td rowspan="1" colspan="1">−0.0016 (9)</td><td rowspan="1" colspan="1">−0.0019 (10)</td><td rowspan="1" colspan="1">0.0010 (9)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0325 (12)</td><td rowspan="1" colspan="1">0.0269 (10)</td><td rowspan="1" colspan="1">0.0283 (13)</td><td rowspan="1" colspan="1">−0.0008 (10)</td><td rowspan="1" colspan="1">−0.0003 (10)</td><td rowspan="1" colspan="1">−0.0008 (10)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0569 (16)</td><td rowspan="1" colspan="1">0.0452 (14)</td><td rowspan="1" colspan="1">0.0308 (14)</td><td rowspan="1" colspan="1">−0.0159 (12)</td><td rowspan="1" colspan="1">−0.0038 (12)</td><td rowspan="1" colspan="1">0.0051 (11)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.073 (2)</td><td rowspan="1" colspan="1">0.0597 (17)</td><td rowspan="1" colspan="1">0.0351 (16)</td><td rowspan="1" colspan="1">−0.0154 (15)</td><td rowspan="1" colspan="1">−0.0165 (15)</td><td rowspan="1" colspan="1">0.0079 (13)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0467 (15)</td><td rowspan="1" colspan="1">0.0543 (16)</td><td rowspan="1" colspan="1">0.0461 (18)</td><td rowspan="1" colspan="1">−0.0139 (13)</td><td rowspan="1" colspan="1">−0.0202 (13)</td><td rowspan="1" colspan="1">0.0050 (13)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0324 (12)</td><td rowspan="1" colspan="1">0.0359 (12)</td><td rowspan="1" colspan="1">0.0386 (15)</td><td rowspan="1" colspan="1">−0.0059 (10)</td><td rowspan="1" colspan="1">−0.0054 (11)</td><td rowspan="1" colspan="1">0.0029 (11)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0330 (12)</td><td rowspan="1" colspan="1">0.0379 (13)</td><td rowspan="1" colspan="1">0.0383 (15)</td><td rowspan="1" colspan="1">−0.0012 (11)</td><td rowspan="1" colspan="1">−0.0049 (11)</td><td rowspan="1" colspan="1">0.0044 (11)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0267 (12)</td><td rowspan="1" colspan="1">0.0571 (16)</td><td rowspan="1" colspan="1">0.0588 (19)</td><td rowspan="1" colspan="1">−0.0071 (12)</td><td rowspan="1" colspan="1">−0.0020 (12)</td><td rowspan="1" colspan="1">0.0002 (14)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0330 (15)</td><td rowspan="1" colspan="1">0.0762 (19)</td><td rowspan="1" colspan="1">0.068 (2)</td><td rowspan="1" colspan="1">−0.0085 (14)</td><td rowspan="1" colspan="1">0.0181 (15)</td><td rowspan="1" colspan="1">−0.0124 (17)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0375 (14)</td><td rowspan="1" colspan="1">0.0573 (16)</td><td rowspan="1" colspan="1">0.0538 (18)</td><td rowspan="1" colspan="1">−0.0063 (13)</td><td rowspan="1" colspan="1">0.0162 (13)</td><td rowspan="1" colspan="1">−0.0148 (14)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0298 (12)</td><td rowspan="1" colspan="1">0.0297 (11)</td><td rowspan="1" colspan="1">0.0376 (14)</td><td rowspan="1" colspan="1">−0.0027 (10)</td><td rowspan="1" colspan="1">0.0052 (11)</td><td rowspan="1" colspan="1">0.0022 (10)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0252 (11)</td><td rowspan="1" colspan="1">0.0265 (10)</td><td rowspan="1" colspan="1">0.0313 (13)</td><td rowspan="1" colspan="1">0.0023 (9)</td><td rowspan="1" colspan="1">0.0007 (10)</td><td rowspan="1" colspan="1">0.0020 (10)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0331 (12)</td><td rowspan="1" colspan="1">0.0321 (12)</td><td rowspan="1" colspan="1">0.0376 (15)</td><td rowspan="1" colspan="1">−0.0013 (10)</td><td rowspan="1" colspan="1">−0.0011 (11)</td><td rowspan="1" colspan="1">−0.0044 (11)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0304 (12)</td><td rowspan="1" colspan="1">0.0318 (12)</td><td rowspan="1" colspan="1">0.0522 (17)</td><td rowspan="1" colspan="1">−0.0077 (10)</td><td rowspan="1" colspan="1">−0.0040 (11)</td><td rowspan="1" colspan="1">−0.0017 (11)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.0333 (13)</td><td rowspan="1" colspan="1">0.0350 (13)</td><td rowspan="1" colspan="1">0.0452 (16)</td><td rowspan="1" colspan="1">−0.0067 (11)</td><td rowspan="1" colspan="1">0.0048 (12)</td><td rowspan="1" colspan="1">0.0056 (12)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.0291 (12)</td><td rowspan="1" colspan="1">0.0364 (12)</td><td rowspan="1" colspan="1">0.0339 (14)</td><td rowspan="1" colspan="1">−0.0034 (10)</td><td rowspan="1" colspan="1">0.0046 (10)</td><td rowspan="1" colspan="1">0.0037 (10)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1969"><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">Co1—N1</td><td rowspan="1" colspan="1">1.9534 (17)</td><td rowspan="1" colspan="1">C1—H1</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">Co1—N3</td><td rowspan="1" colspan="1">1.9680 (18)</td><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.387 (3)</td></tr><tr><td rowspan="1" colspan="1">Co1—N4</td><td rowspan="1" colspan="1">1.9699 (17)</td><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">Co1—N6</td><td rowspan="1" colspan="1">1.9533 (16)</td><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.360 (3)</td></tr><tr><td rowspan="1" colspan="1">Co1—N7</td><td rowspan="1" colspan="1">1.9334 (18)</td><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">Co1—N10</td><td rowspan="1" colspan="1">1.951 (2)</td><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.399 (3)</td></tr><tr><td rowspan="1" colspan="1">S1—O2</td><td rowspan="1" colspan="1">1.4544 (19)</td><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">S1—O2<sup>i</sup></td><td rowspan="1" colspan="1">1.4544 (19)</td><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.384 (3)</td></tr><tr><td rowspan="1" colspan="1">S1—O1<sup>i</sup></td><td rowspan="1" colspan="1">1.4559 (17)</td><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.365 (4)</td></tr><tr><td rowspan="1" colspan="1">S1—O1</td><td rowspan="1" colspan="1">1.4559 (17)</td><td rowspan="1" colspan="1">C7—H7</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">O3—H3A</td><td rowspan="1" colspan="1">0.8578</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.394 (4)</td></tr><tr><td rowspan="1" colspan="1">O3—H3B</td><td rowspan="1" colspan="1">0.8578</td><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C5</td><td rowspan="1" colspan="1">1.342 (3)</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.361 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.356 (3)</td><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N2—C6</td><td rowspan="1" colspan="1">1.378 (3)</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N2—C5</td><td rowspan="1" colspan="1">1.382 (3)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.358 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—H2N</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N3—C6</td><td rowspan="1" colspan="1">1.346 (3)</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.378 (4)</td></tr><tr><td rowspan="1" colspan="1">N3—C10</td><td rowspan="1" colspan="1">1.361 (3)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N4—C15</td><td rowspan="1" colspan="1">1.336 (3)</td><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.364 (4)</td></tr><tr><td rowspan="1" colspan="1">N4—C11</td><td rowspan="1" colspan="1">1.359 (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">N5—C16</td><td rowspan="1" colspan="1">1.378 (2)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.396 (3)</td></tr><tr><td rowspan="1" colspan="1">N5—C15</td><td rowspan="1" colspan="1">1.379 (3)</td><td rowspan="1" colspan="1">C14—H14</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N5—H5N</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C16—C17</td><td rowspan="1" colspan="1">1.402 (3)</td></tr><tr><td rowspan="1" colspan="1">N6—C16</td><td rowspan="1" colspan="1">1.347 (3)</td><td rowspan="1" colspan="1">C17—C18</td><td rowspan="1" colspan="1">1.369 (3)</td></tr><tr><td rowspan="1" colspan="1">N6—C20</td><td rowspan="1" colspan="1">1.364 (3)</td><td rowspan="1" colspan="1">C17—H17</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N7—N8</td><td rowspan="1" colspan="1">1.208 (3)</td><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.382 (3)</td></tr><tr><td rowspan="1" colspan="1">N8—N9</td><td rowspan="1" colspan="1">1.142 (3)</td><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N10—N11</td><td rowspan="1" colspan="1">1.181 (2)</td><td rowspan="1" colspan="1">C19—C20</td><td rowspan="1" colspan="1">1.364 (3)</td></tr><tr><td rowspan="1" colspan="1">N11—N12</td><td rowspan="1" colspan="1">1.148 (3)</td><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.365 (3)</td><td rowspan="1" colspan="1">C20—H20</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1—Co1—N3</td><td rowspan="1" colspan="1">86.48 (7)</td><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">121.0</td></tr><tr><td rowspan="1" colspan="1">N1—Co1—N4</td><td rowspan="1" colspan="1">91.77 (7)</td><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">121.0</td></tr><tr><td rowspan="1" colspan="1">N1—Co1—N6</td><td rowspan="1" colspan="1">176.36 (8)</td><td rowspan="1" colspan="1">C4—C3—C2</td><td rowspan="1" colspan="1">120.1 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—Co1—N7</td><td rowspan="1" colspan="1">90.68 (7)</td><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">N1—Co1—N10</td><td rowspan="1" colspan="1">89.46 (8)</td><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">N3—Co1—N4</td><td rowspan="1" colspan="1">92.28 (7)</td><td rowspan="1" colspan="1">C3—C4—C5</td><td rowspan="1" colspan="1">118.9 (2)</td></tr><tr><td rowspan="1" colspan="1">N3—Co1—N6</td><td rowspan="1" colspan="1">89.89 (7)</td><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">120.6</td></tr><tr><td rowspan="1" colspan="1">N3—Co1—N7</td><td rowspan="1" colspan="1">93.31 (8)</td><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">120.6</td></tr><tr><td rowspan="1" colspan="1">N3—Co1—N10</td><td rowspan="1" colspan="1">175.02 (7)</td><td rowspan="1" colspan="1">N1—C5—C4</td><td rowspan="1" colspan="1">121.6 (2)</td></tr><tr><td rowspan="1" colspan="1">N4—Co1—N6</td><td rowspan="1" colspan="1">88.08 (7)</td><td rowspan="1" colspan="1">N2—C5—C4</td><td rowspan="1" colspan="1">119.04 (19)</td></tr><tr><td rowspan="1" colspan="1">N4—Co1—N7</td><td rowspan="1" colspan="1">174.02 (8)</td><td rowspan="1" colspan="1">N3—C6—C7</td><td rowspan="1" colspan="1">121.6 (2)</td></tr><tr><td rowspan="1" colspan="1">N4—Co1—N10</td><td rowspan="1" colspan="1">84.97 (8)</td><td rowspan="1" colspan="1">N2—C6—C7</td><td rowspan="1" colspan="1">119.27 (19)</td></tr><tr><td rowspan="1" colspan="1">N6—Co1—N7</td><td rowspan="1" colspan="1">89.82 (7)</td><td rowspan="1" colspan="1">C8—C7—C6</td><td rowspan="1" colspan="1">119.7 (2)</td></tr><tr><td rowspan="1" colspan="1">N6—Co1—N10</td><td rowspan="1" colspan="1">94.15 (8)</td><td rowspan="1" colspan="1">C8—C7—H7</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">N7—Co1—N10</td><td rowspan="1" colspan="1">89.61 (9)</td><td rowspan="1" colspan="1">C6—C7—H7</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">N7—N8—N9</td><td rowspan="1" colspan="1">175.7 (2)</td><td rowspan="1" colspan="1">C7—C8—C9</td><td rowspan="1" colspan="1">119.1 (3)</td></tr><tr><td rowspan="1" colspan="1">N10—N11—N12</td><td rowspan="1" colspan="1">175.3 (3)</td><td rowspan="1" colspan="1">C7—C8—H8</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">Co1—N7—N8</td><td rowspan="1" colspan="1">122.05 (15)</td><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">Co1—N10—N11</td><td rowspan="1" colspan="1">126.09 (17)</td><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">118.4 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—N2—C6</td><td rowspan="1" colspan="1">123.44 (17)</td><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">120.8</td></tr><tr><td rowspan="1" colspan="1">C15—N5—C16</td><td rowspan="1" colspan="1">125.87 (19)</td><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">120.8</td></tr><tr><td rowspan="1" colspan="1">N1—C5—N2</td><td rowspan="1" colspan="1">119.38 (18)</td><td rowspan="1" colspan="1">C9—C10—N3</td><td rowspan="1" colspan="1">123.1 (2)</td></tr><tr><td rowspan="1" colspan="1">N2—C6—N3</td><td rowspan="1" colspan="1">119.1 (2)</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">N4—C15—N5</td><td rowspan="1" colspan="1">119.30 (18)</td><td rowspan="1" colspan="1">N3—C10—H10</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">N5—C16—N6</td><td rowspan="1" colspan="1">120.16 (18)</td><td rowspan="1" colspan="1">C12—C11—N4</td><td rowspan="1" colspan="1">123.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—N1—Co1</td><td rowspan="1" colspan="1">120.94 (14)</td><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">C6—N3—Co1</td><td rowspan="1" colspan="1">120.49 (14)</td><td rowspan="1" colspan="1">N4—C11—H11</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">C15—N4—Co1</td><td rowspan="1" colspan="1">122.47 (15)</td><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">118.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C16—N6—Co1</td><td rowspan="1" colspan="1">121.35 (13)</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">120.9</td></tr><tr><td rowspan="1" colspan="1">O2—S1—O2<sup>i</sup></td><td rowspan="1" colspan="1">109.6 (2)</td><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">120.9</td></tr><tr><td rowspan="1" colspan="1">O2—S1—O1<sup>i</sup></td><td rowspan="1" colspan="1">107.60 (11)</td><td rowspan="1" colspan="1">C14—C13—C12</td><td rowspan="1" colspan="1">120.1 (2)</td></tr><tr><td rowspan="1" colspan="1">O2<sup>i</sup>—S1—O1<sup>i</sup></td><td rowspan="1" colspan="1">110.20 (12)</td><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">O2—S1—O1</td><td rowspan="1" colspan="1">110.20 (12)</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">O2<sup>i</sup>—S1—O1</td><td rowspan="1" colspan="1">107.60 (11)</td><td rowspan="1" colspan="1">C13—C14—C15</td><td rowspan="1" colspan="1">118.7 (2)</td></tr><tr><td rowspan="1" colspan="1">O1<sup>i</sup>—S1—O1</td><td rowspan="1" colspan="1">111.63 (15)</td><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">120.7</td></tr><tr><td rowspan="1" colspan="1">H3A—O3—H3B</td><td rowspan="1" colspan="1">103.8</td><td rowspan="1" colspan="1">C15—C14—H14</td><td rowspan="1" colspan="1">120.7</td></tr><tr><td rowspan="1" colspan="1">C5—N1—C1</td><td rowspan="1" colspan="1">117.87 (18)</td><td rowspan="1" colspan="1">N4—C15—C14</td><td rowspan="1" colspan="1">121.9 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—Co1</td><td rowspan="1" colspan="1">121.02 (14)</td><td rowspan="1" colspan="1">N5—C15—C14</td><td rowspan="1" colspan="1">118.8 (2)</td></tr><tr><td rowspan="1" colspan="1">C6—N2—H2N</td><td rowspan="1" colspan="1">118.3</td><td rowspan="1" colspan="1">N6—C16—C17</td><td rowspan="1" colspan="1">121.85 (19)</td></tr><tr><td rowspan="1" colspan="1">C5—N2—H2N</td><td rowspan="1" colspan="1">118.3</td><td rowspan="1" colspan="1">N5—C16—C17</td><td rowspan="1" colspan="1">117.99 (19)</td></tr><tr><td rowspan="1" colspan="1">C6—N3—C10</td><td rowspan="1" colspan="1">117.6 (2)</td><td rowspan="1" colspan="1">C18—C17—C16</td><td rowspan="1" colspan="1">119.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C10—N3—Co1</td><td rowspan="1" colspan="1">121.60 (14)</td><td rowspan="1" colspan="1">C18—C17—H17</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">C15—N4—C11</td><td rowspan="1" colspan="1">117.58 (18)</td><td rowspan="1" colspan="1">C16—C17—H17</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">C11—N4—Co1</td><td rowspan="1" colspan="1">119.71 (15)</td><td rowspan="1" colspan="1">C17—C18—C19</td><td rowspan="1" colspan="1">119.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C16—N5—H5N</td><td rowspan="1" colspan="1">117.1</td><td rowspan="1" colspan="1">C17—C18—H18</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">C15—N5—H5N</td><td rowspan="1" colspan="1">117.1</td><td rowspan="1" colspan="1">C19—C18—H18</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">C16—N6—C20</td><td rowspan="1" colspan="1">117.15 (18)</td><td rowspan="1" colspan="1">C20—C19—C18</td><td rowspan="1" colspan="1">119.1 (2)</td></tr><tr><td rowspan="1" colspan="1">C20—N6—Co1</td><td rowspan="1" colspan="1">120.92 (15)</td><td rowspan="1" colspan="1">C20—C19—H19</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">123.1 (2)</td><td rowspan="1" colspan="1">C18—C19—H19</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">N1—C1—H1</td><td rowspan="1" colspan="1">118.4</td><td rowspan="1" colspan="1">C19—C20—N6</td><td rowspan="1" colspan="1">123.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—H1</td><td rowspan="1" colspan="1">118.4</td><td rowspan="1" colspan="1">C19—C20—H20</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3</td><td rowspan="1" colspan="1">118.1 (2)</td><td rowspan="1" colspan="1">N6—C20—H20</td><td rowspan="1" colspan="1">118.4</td></tr></table></table-wrap><p>Symmetry code: (i) −<italic>x</italic>+1, <italic>y</italic>, −<italic>z</italic>+1/2.</p></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e2780"><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">O3—H3<italic>B</italic>···N12<sup>ii</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.24</td><td rowspan="1" colspan="1">3.095 (4)</td><td rowspan="1" colspan="1">173</td></tr><tr><td rowspan="1" colspan="1">O3—H3<italic>A</italic>···O2<sup>iii</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.02</td><td rowspan="1" colspan="1">2.832 (3)</td><td rowspan="1" colspan="1">158</td></tr><tr><td rowspan="1" colspan="1">N2—H2<italic>N</italic>···O2<sup>iv</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">1.94</td><td rowspan="1" colspan="1">2.708 (2)</td><td rowspan="1" colspan="1">147</td></tr><tr><td rowspan="1" colspan="1">N5—H5<italic>N</italic>···O1</td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.08</td><td rowspan="1" colspan="1">2.742 (2)</td><td rowspan="1" colspan="1">134</td></tr><tr><td rowspan="1" colspan="1">C4—H4···O2<sup>iv</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.67</td><td rowspan="1" colspan="1">3.346 (3)</td><td rowspan="1" colspan="1">130</td></tr><tr><td rowspan="1" colspan="1">C10—H10···O3</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.51</td><td rowspan="1" colspan="1">3.203 (3)</td><td rowspan="1" colspan="1">131</td></tr><tr><td rowspan="1" colspan="1">C11—H11···N10</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.55</td><td rowspan="1" colspan="1">2.911 (3)</td><td rowspan="1" colspan="1">104</td></tr><tr><td rowspan="1" colspan="1">C14—H14···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.49</td><td rowspan="1" colspan="1">3.399 (3)</td><td rowspan="1" colspan="1">165</td></tr><tr><td rowspan="1" colspan="1">C17—H17···O1</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.56</td><td rowspan="1" colspan="1">3.261 (3)</td><td rowspan="1" colspan="1">132</td></tr><tr><td rowspan="1" colspan="1">C20—H20···N7</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.42</td><td rowspan="1" colspan="1">2.837 (3)</td><td rowspan="1" colspan="1">107</td></tr><tr><td rowspan="1" colspan="1">C20—H20···N11</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.60</td><td rowspan="1" colspan="1">3.101 (3)</td><td rowspan="1" colspan="1">114</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+1, <italic>y</italic>, −<italic>z</italic>+1/2; (ii) −<italic>x</italic>+3/2, −<italic>y</italic>+1/2, −<italic>z</italic>; (iii) <italic>x</italic>+1/2, <italic>y</italic>−1/2, <italic>z</italic>; (iv) <italic>x</italic>, <italic>y</italic>−1, <italic>z</italic>.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Barbour, L. 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[Symmetry code: (iv) −<italic>x</italic> + 1, <italic>y</italic>, −<italic>z</italic> + <inline-formula><inline-graphic xlink:href="e-72-00470-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.]</p></caption><graphic xlink:href="e-72-00470-fig1"></graphic></fig><fig id="fig2" position="float"><label>Figure 2</label><caption><p>Conformations of dpa. <italic>Cis</italic> and <italic>trans</italic> refer to the relation of the pyridyl N atoms to the amine N atom.</p></caption><graphic xlink:href="e-72-00470-fig2"></graphic></fig><fig id="fig3" position="float"><label>Figure 3</label><caption><p>Possible coordination modes of dpa involving only pyridyl N atoms. Only modes <bold>I</bold>–<bold>II</bold> and <bold>IV</bold>–<bold>VI</bold> are observed with transition metals.</p></caption><graphic xlink:href="e-72-00470-fig3"></graphic></fig><fig id="fig4" position="float"><label>Figure 4</label><caption><p>The sulfate anions, highlighted in space-filling mode, are sandwiched between two symmetry related layers of complex cations and water molecules.</p></caption><graphic xlink:href="e-72-00470-fig4"></graphic></fig><fig id="fig5" position="float"><label>Figure 5</label><caption><p>Extensive C—H⋯O, N—H⋯O, and O—H⋯O hydrogen bonding, represented by dashed red lines, links the anions, complex cations, and water molecules into sheets parallel to the <italic>ab</italic> plane. For clarity, the pyridine C and H atoms not involved in hydrogen-bonding interactions have been omitted, and only the N atom coordinating to the Co<sup>III</sup> cation is shown for the azide anions. [Symmetry codes: (iv) −<italic>x</italic> + 1, <italic>y</italic>, −<italic>z</italic> + <inline-formula><inline-graphic xlink:href="e-72-00470-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (v) −<italic>x</italic> + <inline-formula><inline-graphic xlink:href="e-72-00470-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>, <italic>y</italic> + <inline-formula><inline-graphic xlink:href="e-72-00470-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>, −<italic>z</italic> + <inline-formula><inline-graphic xlink:href="e-72-00470-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (vi) −<italic>x</italic> + 1, <italic>y</italic> + 1, −<italic>z</italic> + <inline-formula><inline-graphic xlink:href="e-72-00470-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.]</p></caption><graphic xlink:href="e-72-00470-fig5"></graphic></fig><fig id="fig6" position="float"><label>Figure 6</label><caption><p>The two-dimensional supramolecular sheets that lie parallel to the <italic>ab</italic> plane are linked <italic>via</italic> O—H⋯N interactions, represented by dashed blue lines, between the water molecules of one sheet and azide anions of another sheet to form a three-dimensional supramolecular framework. The discussed C—H⋯N hydrogen bonds between neighboring dpa ligands and azide anions within the coordination sphere of the Co<sup>III</sup> cation are represented by dashed yellow lines, and the C—H⋯O, N—H⋯O, and O—H⋯O hydrogen bonds linking the anions, complex cations, and water molecules into sheets are represented by dashed red lines. For clarity hydrogen atoms not involved in hydrogen-bonding interactions have been omitted.</p></caption><graphic xlink:href="e-72-00470-fig6"></graphic></fig><fig id="fig7" position="float"><label>Figure 7</label><caption><p>Scatter plot of py<sub>cent</sub>—N<sub>a</sub>—py<sub>cent</sub> angles <italic>versus</italic> N<sub>py</sub>—<italic>M</italic>—N<sub>py</sub> bite angles for all transition metal complexes reported to the CSD with dpa in coordination mode <bold>VI</bold>. Blue dots represent all complexes with dpa coordinating in bonding mode <bold>VI</bold> to a transition metal. Red dots represent compounds where the metal has a coordination environment similar to the title compound: two dpa in bonding mode <bold>VI</bold> and two terminal azide anions. Black dots represent the title compound.</p></caption><graphic xlink:href="e-72-00470-fig7"></graphic></fig><fig id="fig8" position="float"><label>Figure 8</label><caption><p>Scatter plot of the folding angles about N<sub>a</sub>—<italic>M versus</italic> N<sub>py</sub>—<italic>M</italic>—N<sub>py</sub> bite angles for all transition metal complexes reported to the CSD with dpa in coordination mode <bold>VI</bold>. Blue dots represent all complexes with dpa coordinating in bonding mode <bold>VI</bold> to a transition metal. Red dots represent compounds where the metal has a coordination environment similar to the title compound: two dpa in bonding mode <bold>VI</bold> and two terminal azide anions. Black dots represent the title compound.</p></caption><graphic xlink:href="e-72-00470-fig8"></graphic></fig><fig id="fig9" position="float"><label>Figure 9</label><caption><p>Scatter plot of the folding angles about N<sub>a</sub>—<italic>M versus</italic> mean <italic>M</italic>—N<sub>py</sub> bond length for all transition metal complexes reported to the CSD with dpa in coordination mode <bold>VI</bold>. Blue dots represent all complexes with dpa coordinating in bonding mode <bold>VI</bold> to a transition metal. Red dots represent compounds where the metal has a coordination environment similar to the title compound: two dpa in bonding mode <bold>VI</bold> and two terminal azide anions. Black dots represent the title compound.</p></caption><graphic xlink:href="e-72-00470-fig9"></graphic></fig><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Selected geometric parameters (Å, °)</title></caption><table frame="hsides" rules="groups"><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">Co1—N1</td><td rowspan="1" colspan="1" align="char" valign="top">1.9534 (17)</td><td rowspan="1" colspan="1" align="left" valign="top">Co1—N10</td><td rowspan="1" colspan="1" align="char" valign="top">1.951 (2)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Co1—N3</td><td rowspan="1" colspan="1" align="char" valign="top">1.9680 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">N7—N8</td><td rowspan="1" colspan="1" align="char" valign="top">1.208 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Co1—N4</td><td rowspan="1" colspan="1" align="char" valign="top">1.9699 (17)</td><td rowspan="1" colspan="1" align="left" valign="top">N8—N9</td><td rowspan="1" colspan="1" align="char" valign="top">1.142 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Co1—N6</td><td rowspan="1" colspan="1" align="char" valign="top">1.9533 (16)</td><td rowspan="1" colspan="1" align="left" valign="top">N10—N11</td><td rowspan="1" colspan="1" align="char" valign="top">1.181 (2)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Co1—N7</td><td rowspan="1" colspan="1" align="char" valign="top">1.9334 (18)</td><td rowspan="1" colspan="1" align="left" valign="top">N11—N12</td><td rowspan="1" colspan="1" align="char" valign="top">1.148 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="char" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="char" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—Co1—N3</td><td rowspan="1" colspan="1" align="char" valign="top">86.48 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">N7—N8—N9</td><td rowspan="1" colspan="1" align="char" valign="top">175.7 (2)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—Co1—N4</td><td rowspan="1" colspan="1" align="char" valign="top">91.77 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">N10—N11—N12</td><td rowspan="1" colspan="1" align="char" valign="top">175.3 (3)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—Co1—N6</td><td rowspan="1" colspan="1" align="char" valign="top">176.36 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">Co1—N7—N8</td><td rowspan="1" colspan="1" align="char" valign="top">122.05 (15)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—Co1—N7</td><td rowspan="1" colspan="1" align="char" valign="top">90.68 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">Co1—N10—N11</td><td rowspan="1" colspan="1" align="char" valign="top">126.09 (17)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—Co1—N10</td><td rowspan="1" colspan="1" align="char" valign="top">89.46 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">C5—N2—C6</td><td rowspan="1" colspan="1" align="char" valign="top">123.44 (17)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3—Co1—N4</td><td rowspan="1" colspan="1" align="char" valign="top">92.28 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">C15—N5—C16</td><td rowspan="1" colspan="1" align="char" valign="top">125.87 (19)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3—Co1—N6</td><td rowspan="1" colspan="1" align="char" valign="top">89.89 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">N1—C5—N2</td><td rowspan="1" colspan="1" align="char" valign="top">119.38 (18)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3—Co1—N7</td><td rowspan="1" colspan="1" align="char" valign="top">93.31 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">N2—C6—N3</td><td rowspan="1" colspan="1" align="char" valign="top">119.1 (2)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3—Co1—N10</td><td rowspan="1" colspan="1" align="char" valign="top">175.02 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">N4—C15—N5</td><td rowspan="1" colspan="1" align="char" valign="top">119.30 (18)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N4—Co1—N6</td><td rowspan="1" colspan="1" align="char" valign="top">88.08 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">N5—C16—N6</td><td rowspan="1" colspan="1" align="char" valign="top">120.16 (18)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N4—Co1—N7</td><td rowspan="1" colspan="1" align="char" valign="top">174.02 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">C5—N1—Co1</td><td rowspan="1" colspan="1" align="char" valign="top">120.94 (14)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N4—Co1—N10</td><td rowspan="1" colspan="1" align="char" valign="top">84.97 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">C6—N3—Co1</td><td rowspan="1" colspan="1" align="char" valign="top">120.49 (14)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N6—Co1—N7</td><td rowspan="1" colspan="1" align="char" valign="top">89.82 (7)</td><td rowspan="1" colspan="1" align="left" valign="top">C15—N4—Co1</td><td rowspan="1" colspan="1" align="char" valign="top">122.47 (15)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N6—Co1—N10</td><td rowspan="1" colspan="1" align="char" valign="top">94.15 (8)</td><td rowspan="1" colspan="1" align="left" valign="top">C16—N6—Co1</td><td rowspan="1" colspan="1" align="char" valign="top">121.35 (13)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N7—Co1—N10</td><td rowspan="1" colspan="1" align="char" valign="top">89.61 (9)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="char" valign="top"> </td></tr></tbody></table></table-wrap><table-wrap id="table2" position="float"><label>Table 2</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">O3—H3<italic>B</italic>⋯N12<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">2.24</td><td rowspan="1" colspan="1" align="left" valign="top">3.095 (4)</td><td rowspan="1" colspan="1" align="left" valign="top">173</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">O3—H3<italic>A</italic>⋯O2<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">2.02</td><td rowspan="1" colspan="1" align="left" valign="top">2.832 (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>N</italic>⋯O2<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">1.94</td><td rowspan="1" colspan="1" align="left" valign="top">2.708 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">147</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N5—H5<italic>N</italic>⋯O1</td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">2.08</td><td rowspan="1" colspan="1" align="left" valign="top">2.742 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">134</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C4—H4⋯O2<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.67</td><td rowspan="1" colspan="1" align="left" valign="top">3.346 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">130</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C10—H10⋯O3</td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.51</td><td rowspan="1" colspan="1" align="left" valign="top">3.203 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">131</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C11—H11⋯N10</td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.55</td><td rowspan="1" colspan="1" align="left" valign="top">2.911 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">104</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C14—H14⋯O1<sup>iv</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.49</td><td rowspan="1" colspan="1" align="left" valign="top">3.399 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">165</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C17—H17⋯O1</td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.56</td><td rowspan="1" colspan="1" align="left" valign="top">3.261 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">132</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C20—H20⋯N7</td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.42</td><td rowspan="1" colspan="1" align="left" valign="top">2.837 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">107</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C20—H20⋯N11</td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.60</td><td rowspan="1" colspan="1" align="left" valign="top">3.101 (3)</td><td rowspan="1" colspan="1" align="left" valign="top">114</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-72-00470-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-72-00470-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-72-00470-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iv) <inline-formula><inline-graphic xlink:href="e-72-00470-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap><table-wrap id="table3" position="float"><label>Table 3</label><caption><title>Deviations of atoms from the least-squares planes and angle between planes (Å, °)</title><p>Note: (*) an atom that was not used to define the plane.</p></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">Atom</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Plane 1<sup><italic>a</italic></sup></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Plane 2<sup><italic>b</italic></sup></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Plane 3<sup><italic>c</italic></sup></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Plane 4<sup><italic>d</italic></sup></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Plane 5<sup><italic>e</italic></sup></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">Plane 6<sup><italic>f</italic></sup></th></tr></thead><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">Co1</td><td rowspan="1" colspan="1" align="left" valign="top">−0.1338 (10)</td><td rowspan="1" colspan="1" align="left" valign="top">−0.1647 (11)</td><td rowspan="1" colspan="1" align="left" valign="top">0.1345 (11)</td><td rowspan="1" colspan="1" align="left" valign="top">0.1699 (11)</td><td rowspan="1" colspan="1" align="left" valign="top">−0.8678 (25)*</td><td rowspan="1" colspan="1" align="left" valign="top">0.7703 (27)*</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1</td><td rowspan="1" colspan="1" align="left" valign="top">0.0362 (16)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0061 (9)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N2</td><td rowspan="1" colspan="1" align="left" valign="top">0.1351 (14)</td><td rowspan="1" colspan="1" align="left" valign="top">0.1438 (13)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.3360 (28)*</td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N3</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0556 (14)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0061 (9)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N4</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0521 (16)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0091 (10)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N5</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0985 (14)</td><td rowspan="1" colspan="1" align="left" valign="top">−0.1311 (14)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.2776 (29)*</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N6</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0726 (16)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0091 (9)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C1</td><td rowspan="1" colspan="1" align="left" valign="top">0.0931 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C2</td><td rowspan="1" colspan="1" align="left" valign="top">0.0613 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C3</td><td rowspan="1" colspan="1" align="left" valign="top">−0.0736 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C4</td><td rowspan="1" colspan="1" align="left" valign="top">−0.1218 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C5</td><td rowspan="1" colspan="1" align="left" valign="top">0.0036 (14)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0067 (10)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C6</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0126 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0067 (10)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C7</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.1227 (20)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C8</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.1026 (22)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C9</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0577 (20)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C10</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.1204 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C11</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.1083 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C12</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0322 (20)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C13</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0909 (23)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C14</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0806 (22)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C15</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0150 (20)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0101 (11)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C16</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0248 (19)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.0101 (11)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C17</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.1239 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C18</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">0.1050 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C19</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.0558 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C20</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">−0.1144 (18)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">Angle Between planes (°)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">Plane 1</td><td rowspan="1" colspan="1" align="left" valign="top">Plane 3</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Plane 2</td><td rowspan="1" colspan="1" align="left" valign="top">46.18 (5)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Plane 4</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top">37.400 (6)</td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td><td rowspan="1" colspan="1" align="left" valign="top"> </td></tr></tbody></table><table-wrap-foot><p>Least-squares planes (<italic>x</italic>, <italic>y</italic>, <italic>z</italic> in crystal coordinates) and r.m.s. deviation of fitted atoms (<italic>a</italic>) 17.6944 (0.0050) <italic>x</italic> − 3.3356 (0.0034) <italic>y</italic> + 6.4703 (0.0175) <italic>z</italic> = 11.4816 (0.0019); 0.0936. (<italic>b</italic>) 10.8385 (0.0107) <italic>x</italic> − 6.6693 (0.0036) <italic>y</italic> − 9.4426 (0.0122) <italic>z</italic> = 5.6865 (0.0073); 0.1087. (<italic>c</italic>) 3.1401 (0.0101) <italic>x</italic> − 6.8035 (0.0036) <italic>y</italic> + 16.3074 (0.0138) <italic>z</italic> = 2.5612 (0.0063); 0.0853. (<italic>d</italic>) 14.1733 (0.0085) <italic>x</italic> − 4.0917 (0.0033) <italic>y</italic> + 13.8837 (0.0152) <italic>z</italic> = 9.4863 (0.0050): 0.1087. (<italic>e</italic>) 14.7476 (0.0151) <italic>x</italic> − 5.8441 (0.0074) <italic>y</italic> − 0.5348 (0.0288) <italic>z</italic> = 9.6107 (0.0074); 0.0064. (<italic>f</italic>) 9.4731 (0.0138) <italic>x</italic> − 6.0570 (0.0073) <italic>y</italic> + 14.4127 (0.0340) <italic>z</italic> = 5.8151 (0.0082); 0.0096.</p></table-wrap-foot></table-wrap><table-wrap id="table4" position="float"><label>Table 4</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">[Co(N<sub>3</sub>)<sub>2</sub>(C<sub>10</sub>H<sub>9</sub>N<sub>3</sub>)<sub>2</sub>]<sub>2</sub>SO<sub>4</sub>·2H<sub>2</sub>O</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">1102.88</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>C</italic>2/<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">293</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">19.9014 (4), 8.7044 (2), 27.1181 (5)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">β (°)</td><td rowspan="1" colspan="1" align="left" valign="top">90.753 (1)</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">4697.25 (17)</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">0.83</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">0.26 × 0.17 × 0.09</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 APEXII CCD</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, 2009<xref ref-type="bibr" rid="bb6"> ▸</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">0.808, 0.875</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">50250, 6893, 3940</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">0.096</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">0.705</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">0.043, 0.094, 0.90</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">6893</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">331</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-atom parameters constrained</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">0.49, −0.52</td></tr></tbody></table><table-wrap-foot><p>Computer programs: <italic>APEX2</italic> and <italic>SAINT</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb6"> ▸</xref>), <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb30"> ▸</xref>), <italic>SHELXL2014</italic> (Sheldrick, 2015<xref ref-type="bibr" rid="bb31"> ▸</xref>) and <italic>X-SEED</italic> (Barbour, 2001<xref ref-type="bibr" rid="bb1"> ▸</xref>).</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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