Tetrakis(μ-2-phenylacetato-κ2O:O′)bis{[4-(dimethylamino)pyridine-κN1]cobalt(II)}
Identifieur interne : 000374 ( Pmc/Corpus ); précédent : 000373; suivant : 000375Tetrakis(μ-2-phenylacetato-κ2O:O′)bis{[4-(dimethylamino)pyridine-κN1]cobalt(II)}
Auteurs : Meriem Benslimane ; Yasmine Kheira Redjel ; Georges Dénès ; Hocine MerazigSource :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2013.
Abstract
The title compound, [Co2(C8H7O2)4(C7H10N2)2], crystallizes as a centrosymmetric dimer containing two CoII atoms bridged by four bidentate phenylacetate ligands in
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DOI: 10.1107/S1600536813023258
PubMed: 24427006
PubMed Central: 3884428
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PMC:3884428Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Tetrakis(μ-2-phenylacetato-κ<sup>2</sup><italic>O</italic>:<italic>O</italic>′)bis{[4-(dimethylamino)pyridine-κ<italic>N</italic><sup>1</sup>]cobalt(II)}</title><author><name sortKey="Benslimane, Meriem" sort="Benslimane, Meriem" uniqKey="Benslimane M" first="Meriem" last="Benslimane">Meriem Benslimane</name><affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Redjel, Yasmine Kheira" sort="Redjel, Yasmine Kheira" uniqKey="Redjel Y" first="Yasmine Kheira" last="Redjel">Yasmine Kheira Redjel</name><affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Denes, Georges" sort="Denes, Georges" uniqKey="Denes G" first="Georges" last="Dénès">Georges Dénès</name><affiliation><nlm:aff id="b">Department of Chemistry and Biochemistry, Concordia University, Montréal,<country>Canada</country></nlm:aff></affiliation></author><author><name sortKey="Merazig, Hocine" sort="Merazig, Hocine" uniqKey="Merazig H" first="Hocine" last="Merazig">Hocine Merazig</name><affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">24427006</idno><idno type="pmc">3884428</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884428</idno><idno type="RBID">PMC:3884428</idno><idno type="doi">10.1107/S1600536813023258</idno><date when="2013">2013</date><idno type="wicri:Area/Pmc/Corpus">000374</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000374</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Tetrakis(μ-2-phenylacetato-κ<sup>2</sup><italic>O</italic>:<italic>O</italic>′)bis{[4-(dimethylamino)pyridine-κ<italic>N</italic><sup>1</sup>]cobalt(II)}</title><author><name sortKey="Benslimane, Meriem" sort="Benslimane, Meriem" uniqKey="Benslimane M" first="Meriem" last="Benslimane">Meriem Benslimane</name><affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Redjel, Yasmine Kheira" sort="Redjel, Yasmine Kheira" uniqKey="Redjel Y" first="Yasmine Kheira" last="Redjel">Yasmine Kheira Redjel</name><affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></nlm:aff></affiliation></author><author><name sortKey="Denes, Georges" sort="Denes, Georges" uniqKey="Denes G" first="Georges" last="Dénès">Georges Dénès</name><affiliation><nlm:aff id="b">Department of Chemistry and Biochemistry, Concordia University, Montréal,<country>Canada</country></nlm:aff></affiliation></author><author><name sortKey="Merazig, Hocine" sort="Merazig, Hocine" uniqKey="Merazig H" first="Hocine" last="Merazig">Hocine Merazig</name><affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title><idno type="eISSN">1600-5368</idno><imprint><date when="2013">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The title compound, [Co<sub>2</sub>(C<sub>8</sub>H<sub>7</sub>O<sub>2</sub>)<sub>4</sub>(C<sub>7</sub>H<sub>10</sub>N<sub>2</sub>)<sub>2</sub>], crystallizes as a centrosymmetric dimer containing two Co<sup>II</sup> atoms bridged by four bidentate phenylacetate ligands in <italic>syn–syn</italic> bridging modes. Each Co<sup>II</sup> atom is five-coordinated by four O atoms from four different carboxylate ligands and the ring N atom of a 4-(dimethylamino)pyridine unit, generating a distorted square-pyramidal geometry in which the four O atoms form the basal plane and the N atom occupies the axial position. In the crystal, C—H⋯O interactions link the dinuclear complex molecules into a three-dimensional network.</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></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title></journal-title-group><issn pub-type="epub">1600-5368</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">24427006</article-id><article-id pub-id-type="pmc">3884428</article-id><article-id pub-id-type="publisher-id">lr2113</article-id><article-id pub-id-type="doi">10.1107/S1600536813023258</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536813023258</article-id><article-categories><subj-group subj-group-type="heading"><subject>Metal-Organic Papers</subject></subj-group></article-categories><title-group><article-title>Tetrakis(μ-2-phenylacetato-κ<sup>2</sup><italic>O</italic>:<italic>O</italic>′)bis{[4-(dimethylamino)pyridine-κ<italic>N</italic><sup>1</sup>]cobalt(II)}</article-title><alt-title><italic>[Co<sub>2</sub>(C<sub>8</sub>H<sub>7</sub>O<sub>2</sub>)<sub>4</sub>(C<sub>7</sub>H<sub>10</sub>N<sub>2</sub>)<sub>2</sub>]</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Benslimane</surname><given-names>Meriem</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>Redjel</surname><given-names>Yasmine Kheira</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Dénès</surname><given-names>Georges</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Merazig</surname><given-names>Hocine</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><aff id="a"><label>a</label>Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country></aff><aff id="b"><label>b</label>Department of Chemistry and Biochemistry, Concordia University, Montréal,<country>Canada</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>b_meriem80@yahoo.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>9</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>23</day><month>8</month><year>2013</year></pub-date><pub-date pub-type="pmc-release"><day>23</day><month>8</month><year>2013</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>69</volume><issue>Pt 9</issue><issue-id pub-id-type="publisher-id">e130900</issue-id><fpage>m517</fpage><lpage>m518</lpage><history><date date-type="received"><day>05</day><month>8</month><year>2013</year></date><date date-type="accepted"><day>19</day><month>8</month><year>2013</year></date></history><permissions><copyright-statement>© Benslimane et al. 2013</copyright-statement><copyright-year>2013</copyright-year><license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p></license></permissions><self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536813023258">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>The title compound, [Co<sub>2</sub>(C<sub>8</sub>H<sub>7</sub>O<sub>2</sub>)<sub>4</sub>(C<sub>7</sub>H<sub>10</sub>N<sub>2</sub>)<sub>2</sub>], crystallizes as a centrosymmetric dimer containing two Co<sup>II</sup> atoms bridged by four bidentate phenylacetate ligands in <italic>syn–syn</italic> bridging modes. Each Co<sup>II</sup> atom is five-coordinated by four O atoms from four different carboxylate ligands and the ring N atom of a 4-(dimethylamino)pyridine unit, generating a distorted square-pyramidal geometry in which the four O atoms form the basal plane and the N atom occupies the axial position. In the crystal, C—H⋯O interactions link the dinuclear complex molecules into a three-dimensional network.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature
</title><p>For properties of the 4-(dimethylamino)pyridine ligand as a homogeneous catalyst, see: Satgé <italic>et al.</italic> (2004<xref ref-type="bibr" rid="bb9"> ▶</xref>). For transition metal complexes of 4-(dimethylamino)pyridine which exhibit luminescence properties, see: Araki <italic>et al.</italic> (2005<xref ref-type="bibr" rid="bb2"> ▶</xref>). For biological and magnetic properties of carboxylic acid complexes of cobalt(II), see: Cotton <italic>et al.</italic> (1999<xref ref-type="bibr" rid="bb6"> ▶</xref>). For related centrosymmetric dinuclear cobalt(II) complexes bridged by carboxylates, see: Cui <italic>et al.</italic> (1999<xref ref-type="bibr" rid="bb7"> ▶</xref>); Catterick & Thornton (1977<xref ref-type="bibr" rid="bb5"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-69-0m517-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec id="sec2"><title>Experimental
</title><sec id="sec2.1"><title></title><sec id="sec2.1.1"><title>Crystal data
</title><p><list list-type="simple" id="l1"><list-item><p>[Co<sub>2</sub>(C<sub>8</sub>H<sub>7</sub>O<sub>2</sub>)<sub>4</sub>(C<sub>7</sub>H<sub>10</sub>N<sub>2</sub>)<sub>2</sub>]</p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 902.74</p></list-item><list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-69-0m517-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 8.107 (5) Å</p></list-item><list-item><p><italic>b</italic> = 11.043 (5) Å</p></list-item><list-item><p><italic>c</italic> = 12.573 (5) Å</p></list-item><list-item><p>α = 99.766 (5)°</p></list-item><list-item><p>β = 101.878 (5)°</p></list-item><list-item><p>γ = 105.335 (5)°</p></list-item><list-item><p><italic>V</italic> = 1031.9 (9) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 1</p></list-item><list-item><p>Mo <italic>K</italic>α radiation</p></list-item><list-item><p>μ = 0.86 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 150 K</p></list-item><list-item><p>0.15 × 0.10 × 0.01 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection
</title><p><list list-type="simple" id="l2"><list-item><p>Bruker APEXII CCD diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2012<xref ref-type="bibr" rid="bb3"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.902, <italic>T</italic><sub>max</sub> = 0.991</p></list-item><list-item><p>9238 measured reflections</p></list-item><list-item><p>3645 independent reflections</p></list-item><list-item><p>3352 reflections with <italic>I</italic> > 2σ(<italic>I</italic>))</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.019</p></list-item></list></p></sec><sec id="sec2.1.3"><title>Refinement
</title><p><list list-type="simple" id="l3"><list-item><p><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.025</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.060</p></list-item><list-item><p><italic>S</italic> = 1.05</p></list-item><list-item><p>3645 reflections</p></list-item><list-item><p>271 parameters</p></list-item><list-item><p>H-atom parameters constrained</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.25 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.24 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e549"><title></title><p>Data collection: <italic>APEX2</italic> (Bruker, 2012<xref ref-type="bibr" rid="bb3"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2012<xref ref-type="bibr" rid="bb3"> ▶</xref>); data reduction: <italic>SAINT</italic>; program(s) used to solve structure: <italic>SIR92</italic> (Altomare <italic>et al.</italic>, 1993<xref ref-type="bibr" rid="bb1"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb10"> ▶</xref>); molecular graphics: <italic>ORTEPIII</italic> (Burnett & Johnson, 1996<xref ref-type="bibr" rid="bb4"> ▶</xref>) and <italic>ORTEP-3 for Windows</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb8"> ▶</xref>); software used to prepare material for publication: <italic>SHELXL97</italic>.</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) global, I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536813023258/lr2113sup1.cif">10.1107/S1600536813023258/lr2113sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-69-0m517-sup1.cif" xlink:type="simple" id="d35e164" 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/S1600536813023258/lr2113Isup2.hkl">10.1107/S1600536813023258/lr2113Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-69-0m517-Isup2.hkl" xlink:type="simple" id="d35e171" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?lr2113&file=lr2113sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?lr2113sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?lr2113&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><fn-group><fn id="fnu1"><p>Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsup?lr2113">LR2113</ext-link>).</p></fn></fn-group><ack><p>This work was supported by the University of Constantine 1.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>1. Comment </title><p>The N-heteroaromatic ligand 4-(dimethylamino)pyridine (DMAP) finds use as a
homogeneous catalyst in cellulose acylation in the synthesis of biodegradable
plastics (Satgé <italic>et al.</italic>, 2004). DMAP is also known to form
transition
metal complexes which exhibit luminescence properties (Araki <italic>et al.</italic>,
2005). Our interest in cobalt(II) carboxylates with DMAP evolves from
their
catalytic activity. Moreover, carboxylic acid complexes of cobalt(II) have
properties of special interest in the fields of biology and magnetism (Cotton
<italic>et al.</italic>, 1999). The coordination chemistry of centrosymmetric
dinuclear
Co<sup>2+</sup> complexes bridged by carboxylates has been investigated (Cui <italic>et
al.</italic>, 1999, Catterick <italic>et al.</italic>, 1977). In order to
explore further the
coordination behaviour of the Co<sup>2+</sup> ion, the title complex, incorporating
phenylacetate and DMAP as co-ligand has been prepared and its crystal
structure is reported here.</p><p>The title molecule is a centrosymmetric dimer with four bidentate phenylacetate
groups as bridging ligands between two Co<sup>II</sup> centres, to each of which a DMAP
group is also coordinated, as shown in Fig. 1. The coordination geometry about
each Co atom is distorted square pyramidal, with four O atoms from four
different carboxylate ligands forming the basal plane and a pyridine N atom
occupying the axial position, where the most distorted angle is 101.39 (5)°
for O2<sup>i</sup>—Co—N2 [symmetry code: (i) -<italic>x</italic> + 1,-<italic>y</italic>,-<italic>z</italic>].
The interatomic distances of Co—O [2.0224 (12)–2.0628 (16) Å], Co—N2
[2.0460 (16) Å] and Co···Co [2.8019 (12) Å] agree well with the
related values recorded for the structures of the analogous pivalate (Cui
<italic>et al.</italic>, 1999) and benzoate (Catterick <italic>et al.</italic>,
1977). The Co(II)
atom is 0.2286 (2) Å from the mean plane formed by the four equatorial O
atoms. On the other hand, the coordinated N2 atom also lies in the same
direction, at a distance of 2.2643 (13) Å from the plane. The dihedral angles
between the mean planes through the C10—C15 and C18—C23 benzene rings and
the DMPA plane are 7.46 (9)° and 72.08 (9)°, respectively. The dihedral angle
between the planes trough Co1/O3/O4/C16/Co1<sup>i</sup>/O3<sup>i</sup>/O4<sup>i</sup>/C16<sup>i</sup> and
Co1/O1/O2/C8/Co1<sup>i</sup>/O1<sup>i</sup>/O2<sup>i</sup>/C8<sup>i</sup>[symmetry code:(i) 1 - <italic>x</italic>, -<italic>y</italic>,
-<italic>z</italic>] is 87.22 (4)°, which is close to the ideal value of
90°.
Nonclassical C—H···O hydrogen bonds (Table 1) occur in the structure,
which link adjacent complex molecule into a three-dimensional network , Fig. 2
and Fig. 3.</p></sec><sec id="experimental"><title>2. Experimental </title><p>CoCl<sub>2.</sub>2H<sub>2</sub>O (0.116 g,1 mmol) was dissolved in methanol (10 ml). To this
solution, phenyacetic acid (C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>COOH; 0.136 g, 1 mmol) was added and
the mixture was stirred for <italic>ca</italic> 10 min to obtain a bleu solution.
4-(Dimethylamino)pyridine (0.122 g, 1 mmol) was added and the mixture was
stirred for an additional 2 h. Single crystals suitable for X-ray diffraction
were obtained from a methanol solution of the title complex by slow
evaporation.</p></sec><sec id="refinement"><title>3. Refinement </title><p>The C-bound H atoms were included in calculated positions, with C—H = 0.93 Å (aromatic), 0.96 Å (methyl), 0.97 Å(aliphatic) and refined using a
riding model, with <italic>U</italic><sub>iso</sub>(H) = 1.5<italic>U</italic><sub>eq</sub>(C) for the methyl groups
and 1.2<italic>U</italic><sub>eq</sub>(C) for the remainder.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Symmetry code, (i):1 - x, -y, -z.</p></caption><graphic xlink:href="e-69-0m517-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines. Symmetry code, (ii): x, y, 1 + z.</p></caption><graphic xlink:href="e-69-0m517-fig2"></graphic></fig><fig id="Fap3"><label>Fig. 3.</label><caption><p>The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.Symmetry code, (iii):2 - x, -y, -z.</p></caption><graphic xlink:href="e-69-0m517-fig3"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e260"><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<sub>2</sub>(C<sub>8</sub>H<sub>7</sub>O<sub>2</sub>)<sub>4</sub>(C<sub>7</sub>H<sub>10</sub>N<sub>2</sub>)<sub>2</sub>]</td><td rowspan="1" colspan="1"><italic>Z</italic> = 1</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 902.74</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 470</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.453 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 1</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> = 8.107 (5) Å</td><td rowspan="1" colspan="1">Cell parameters from 4872 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.043 (5) Å</td><td rowspan="1" colspan="1">θ = 2.3–25°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.573 (5) Å</td><td rowspan="1" colspan="1">µ = 0.86 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">α = 99.766 (5)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 150 K</td></tr><tr><td rowspan="1" colspan="1">β = 101.878 (5)°</td><td rowspan="1" colspan="1">Box, blue</td></tr><tr><td rowspan="1" colspan="1">γ = 105.335 (5)°</td><td rowspan="1" colspan="1">0.15 × 0.1 × 0.01 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1031.9 (9) Å<sup>3</sup></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e413"><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">3645 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">3352 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> = 0.019</td></tr><tr><td rowspan="1" colspan="1">ω and φ scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 25.0°, θ<sub>min</sub> = 2.7°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2012)</td><td rowspan="1" colspan="1"><italic>h</italic> = −9→9</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.902, <italic>T</italic><sub>max</sub> = 0.991</td><td rowspan="1" colspan="1"><italic>k</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1">9238 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −14→14</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e530"><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">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.025</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0206<italic>P</italic>)<sup>2</sup> + 0.6871<italic>P</italic>] where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.060</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.05</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.25 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">3645 reflections</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.24 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">271 parameters</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e682"><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><tr><td rowspan="1" colspan="1">Refinement. Refinement of <italic>F</italic><sup>2</sup> against ALL reflections. The weighted <italic>R</italic>-factor
<italic>wR</italic> and goodness of fit <italic>S</italic> are based on <italic>F</italic><sup>2</sup>, conventional
<italic>R</italic>-factors <italic>R</italic> are based on <italic>F</italic>, with <italic>F</italic> set to zero for
negative <italic>F</italic><sup>2</sup>. The threshold expression of <italic>F</italic><sup>2</sup> >
σ(<italic>F</italic><sup>2</sup>) is used only for calculating <italic>R</italic>-factors(gt) <italic>etc</italic>.
and is not relevant to the choice of reflections for refinement.
<italic>R</italic>-factors based on <italic>F</italic><sup>2</sup> are statistically about twice as large
as those based on <italic>F</italic>, and <italic>R</italic>- factors based on ALL data will be
even larger.</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="d1e781"><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">0.56888 (3)</td><td rowspan="1" colspan="1">0.01135 (2)</td><td rowspan="1" colspan="1">0.114253 (18)</td><td rowspan="1" colspan="1">0.01603 (8)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.70384 (17)</td><td rowspan="1" colspan="1">0.18802 (11)</td><td rowspan="1" colspan="1">0.09742 (10)</td><td rowspan="1" colspan="1">0.0256 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.75242 (16)</td><td rowspan="1" colspan="1">−0.06983 (12)</td><td rowspan="1" colspan="1">0.07678 (10)</td><td rowspan="1" colspan="1">0.0241 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.59969 (17)</td><td rowspan="1" colspan="1">0.17191 (12)</td><td rowspan="1" colspan="1">−0.08452 (10)</td><td rowspan="1" colspan="1">0.0248 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.64516 (17)</td><td rowspan="1" colspan="1">−0.08060 (13)</td><td rowspan="1" colspan="1">−0.10383 (10)</td><td rowspan="1" colspan="1">0.0277 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.7414 (2)</td><td rowspan="1" colspan="1">0.15583 (15)</td><td rowspan="1" colspan="1">0.63408 (12)</td><td rowspan="1" colspan="1">0.0259 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.64381 (19)</td><td rowspan="1" colspan="1">0.06270 (13)</td><td rowspan="1" colspan="1">0.28539 (11)</td><td rowspan="1" colspan="1">0.0178 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.7997 (2)</td><td rowspan="1" colspan="1">0.46694 (16)</td><td rowspan="1" colspan="1">0.12315 (14)</td><td rowspan="1" colspan="1">0.0192 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.7158 (2)</td><td rowspan="1" colspan="1">−0.00546 (16)</td><td rowspan="1" colspan="1">0.34964 (14)</td><td rowspan="1" colspan="1">0.0197 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.7415</td><td rowspan="1" colspan="1">−0.0764</td><td rowspan="1" colspan="1">0.3139</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.7164 (3)</td><td rowspan="1" colspan="1">0.55861 (17)</td><td rowspan="1" colspan="1">0.10444 (16)</td><td rowspan="1" colspan="1">0.0256 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">0.6661</td><td rowspan="1" colspan="1">0.5599</td><td rowspan="1" colspan="1">0.0313</td><td rowspan="1" colspan="1">0.031*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.7158 (2)</td><td rowspan="1" colspan="1">0.12779 (17)</td><td rowspan="1" colspan="1">0.52207 (14)</td><td rowspan="1" colspan="1">0.0195 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.8183 (2)</td><td rowspan="1" colspan="1">−0.25048 (16)</td><td rowspan="1" colspan="1">−0.17600 (14)</td><td rowspan="1" colspan="1">0.0181 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.7818 (3)</td><td rowspan="1" colspan="1">0.64805 (18)</td><td rowspan="1" colspan="1">0.30092 (16)</td><td rowspan="1" colspan="1">0.0302 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.7766</td><td rowspan="1" colspan="1">0.7085</td><td rowspan="1" colspan="1">0.3603</td><td rowspan="1" colspan="1">0.036*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.8651 (2)</td><td rowspan="1" colspan="1">−0.18185 (17)</td><td rowspan="1" colspan="1">−0.05447 (14)</td><td rowspan="1" colspan="1">0.0205 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17A</td><td rowspan="1" colspan="1">0.9855</td><td rowspan="1" colspan="1">−0.1236</td><td rowspan="1" colspan="1">−0.0338</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17B</td><td rowspan="1" colspan="1">0.8624</td><td rowspan="1" colspan="1">−0.2454</td><td rowspan="1" colspan="1">−0.0097</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.9124 (2)</td><td rowspan="1" colspan="1">−0.20046 (17)</td><td rowspan="1" colspan="1">−0.24739 (15)</td><td rowspan="1" colspan="1">0.0222 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H23</td><td rowspan="1" colspan="1">1.0052</td><td rowspan="1" colspan="1">−0.1233</td><td rowspan="1" colspan="1">−0.2202</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.7540 (2)</td><td rowspan="1" colspan="1">0.02208 (17)</td><td rowspan="1" colspan="1">0.46401 (14)</td><td rowspan="1" colspan="1">0.0216 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.8051</td><td rowspan="1" colspan="1">−0.0289</td><td rowspan="1" colspan="1">0.5033</td><td rowspan="1" colspan="1">0.026*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.6790 (2)</td><td rowspan="1" colspan="1">−0.36483 (17)</td><td rowspan="1" colspan="1">−0.21909 (15)</td><td rowspan="1" colspan="1">0.0245 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">0.6135</td><td rowspan="1" colspan="1">−0.399</td><td rowspan="1" colspan="1">−0.1724</td><td rowspan="1" colspan="1">0.029*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.8102 (3)</td><td rowspan="1" colspan="1">0.37074 (16)</td><td rowspan="1" colspan="1">0.02588 (15)</td><td rowspan="1" colspan="1">0.0236 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9A</td><td rowspan="1" colspan="1">0.9324</td><td rowspan="1" colspan="1">0.3717</td><td rowspan="1" colspan="1">0.0358</td><td rowspan="1" colspan="1">0.028*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9B</td><td rowspan="1" colspan="1">0.7754</td><td rowspan="1" colspan="1">0.3982</td><td rowspan="1" colspan="1">−0.0424</td><td rowspan="1" colspan="1">0.028*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.8655 (3)</td><td rowspan="1" colspan="1">0.55707 (19)</td><td rowspan="1" colspan="1">0.32101 (16)</td><td rowspan="1" colspan="1">0.0311 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">0.9163</td><td rowspan="1" colspan="1">0.5563</td><td rowspan="1" colspan="1">0.3942</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.6139 (2)</td><td rowspan="1" colspan="1">0.16674 (17)</td><td rowspan="1" colspan="1">0.34079 (14)</td><td rowspan="1" colspan="1">0.0228 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.568</td><td rowspan="1" colspan="1">0.2179</td><td rowspan="1" colspan="1">0.299</td><td rowspan="1" colspan="1">0.027*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.8741 (2)</td><td rowspan="1" colspan="1">0.46726 (18)</td><td rowspan="1" colspan="1">0.23306 (15)</td><td rowspan="1" colspan="1">0.0267 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.9303</td><td rowspan="1" colspan="1">0.4063</td><td rowspan="1" colspan="1">0.2476</td><td rowspan="1" colspan="1">0.032*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.6466 (2)</td><td rowspan="1" colspan="1">0.20198 (17)</td><td rowspan="1" colspan="1">0.45452 (15)</td><td rowspan="1" colspan="1">0.0246 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.6231</td><td rowspan="1" colspan="1">0.2753</td><td rowspan="1" colspan="1">0.4876</td><td rowspan="1" colspan="1">0.029*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.8696 (3)</td><td rowspan="1" colspan="1">−0.26441 (19)</td><td rowspan="1" colspan="1">−0.35918 (15)</td><td rowspan="1" colspan="1">0.0274 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H22</td><td rowspan="1" colspan="1">0.934</td><td rowspan="1" colspan="1">−0.23</td><td rowspan="1" colspan="1">−0.4062</td><td rowspan="1" colspan="1">0.033*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.7435 (2)</td><td rowspan="1" colspan="1">−0.10501 (16)</td><td rowspan="1" colspan="1">−0.02568 (14)</td><td rowspan="1" colspan="1">0.0180 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.6361 (3)</td><td rowspan="1" colspan="1">−0.42857 (18)</td><td rowspan="1" colspan="1">−0.33028 (16)</td><td rowspan="1" colspan="1">0.0291 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H20</td><td rowspan="1" colspan="1">0.5425</td><td rowspan="1" colspan="1">−0.5053</td><td rowspan="1" colspan="1">−0.3579</td><td rowspan="1" colspan="1">0.035*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.7061 (3)</td><td rowspan="1" colspan="1">0.64871 (18)</td><td rowspan="1" colspan="1">0.19226 (17)</td><td rowspan="1" colspan="1">0.0322 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.6487</td><td rowspan="1" colspan="1">0.7091</td><td rowspan="1" colspan="1">0.178</td><td rowspan="1" colspan="1">0.039*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.6943 (2)</td><td rowspan="1" colspan="1">0.23260 (16)</td><td rowspan="1" colspan="1">0.01192 (14)</td><td rowspan="1" colspan="1">0.0186 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.8177 (3)</td><td rowspan="1" colspan="1">0.0810 (2)</td><td rowspan="1" colspan="1">0.70317 (16)</td><td rowspan="1" colspan="1">0.0328 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7A</td><td rowspan="1" colspan="1">0.8256</td><td rowspan="1" colspan="1">0.1152</td><td rowspan="1" colspan="1">0.7802</td><td rowspan="1" colspan="1">0.049*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7B</td><td rowspan="1" colspan="1">0.9341</td><td rowspan="1" colspan="1">0.0858</td><td rowspan="1" colspan="1">0.6946</td><td rowspan="1" colspan="1">0.049*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7C</td><td rowspan="1" colspan="1">0.7438</td><td rowspan="1" colspan="1">−0.0076</td><td rowspan="1" colspan="1">0.6804</td><td rowspan="1" colspan="1">0.049*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.7319 (3)</td><td rowspan="1" colspan="1">−0.37875 (19)</td><td rowspan="1" colspan="1">−0.40079 (15)</td><td rowspan="1" colspan="1">0.0292 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H21</td><td rowspan="1" colspan="1">0.7037</td><td rowspan="1" colspan="1">−0.4219</td><td rowspan="1" colspan="1">−0.4756</td><td rowspan="1" colspan="1">0.035*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.6940 (3)</td><td rowspan="1" colspan="1">0.2633 (2)</td><td rowspan="1" colspan="1">0.68950 (16)</td><td rowspan="1" colspan="1">0.0353 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6A</td><td rowspan="1" colspan="1">0.721</td><td rowspan="1" colspan="1">0.2693</td><td rowspan="1" colspan="1">0.7686</td><td rowspan="1" colspan="1">0.053*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6B</td><td rowspan="1" colspan="1">0.5694</td><td rowspan="1" colspan="1">0.2493</td><td rowspan="1" colspan="1">0.6611</td><td rowspan="1" colspan="1">0.053*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6C</td><td rowspan="1" colspan="1">0.7601</td><td rowspan="1" colspan="1">0.3421</td><td rowspan="1" colspan="1">0.6754</td><td rowspan="1" colspan="1">0.053*</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="d1e1548"><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">0.02007 (13)</td><td rowspan="1" colspan="1">0.01633 (13)</td><td rowspan="1" colspan="1">0.01213 (12)</td><td rowspan="1" colspan="1">0.00678 (9)</td><td rowspan="1" colspan="1">0.00475 (9)</td><td rowspan="1" colspan="1">0.00211 (9)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0329 (7)</td><td rowspan="1" colspan="1">0.0188 (6)</td><td rowspan="1" colspan="1">0.0213 (7)</td><td rowspan="1" colspan="1">0.0030 (5)</td><td rowspan="1" colspan="1">0.0044 (6)</td><td rowspan="1" colspan="1">0.0066 (5)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0262 (7)</td><td rowspan="1" colspan="1">0.0258 (7)</td><td rowspan="1" colspan="1">0.0218 (7)</td><td rowspan="1" colspan="1">0.0115 (5)</td><td rowspan="1" colspan="1">0.0093 (5)</td><td rowspan="1" colspan="1">0.0010 (5)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0293 (7)</td><td rowspan="1" colspan="1">0.0213 (6)</td><td rowspan="1" colspan="1">0.0190 (6)</td><td rowspan="1" colspan="1">0.0020 (5)</td><td rowspan="1" colspan="1">0.0056 (6)</td><td rowspan="1" colspan="1">0.0022 (5)</td></tr><tr><td rowspan="1" colspan="1">O4</td><td rowspan="1" colspan="1">0.0278 (7)</td><td rowspan="1" colspan="1">0.0354 (8)</td><td rowspan="1" colspan="1">0.0261 (7)</td><td rowspan="1" colspan="1">0.0202 (6)</td><td rowspan="1" colspan="1">0.0074 (6)</td><td rowspan="1" colspan="1">0.0073 (6)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0366 (9)</td><td rowspan="1" colspan="1">0.0275 (8)</td><td rowspan="1" colspan="1">0.0140 (7)</td><td rowspan="1" colspan="1">0.0111 (7)</td><td rowspan="1" colspan="1">0.0067 (7)</td><td rowspan="1" colspan="1">0.0044 (6)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0212 (7)</td><td rowspan="1" colspan="1">0.0178 (7)</td><td rowspan="1" colspan="1">0.0146 (7)</td><td rowspan="1" colspan="1">0.0072 (6)</td><td rowspan="1" colspan="1">0.0048 (6)</td><td rowspan="1" colspan="1">0.0029 (6)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0187 (9)</td><td rowspan="1" colspan="1">0.0152 (8)</td><td rowspan="1" colspan="1">0.0212 (9)</td><td rowspan="1" colspan="1">0.0001 (7)</td><td rowspan="1" colspan="1">0.0075 (7)</td><td rowspan="1" colspan="1">0.0034 (7)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0234 (9)</td><td rowspan="1" colspan="1">0.0163 (8)</td><td rowspan="1" colspan="1">0.0209 (9)</td><td rowspan="1" colspan="1">0.0086 (7)</td><td rowspan="1" colspan="1">0.0065 (7)</td><td rowspan="1" colspan="1">0.0030 (7)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0319 (10)</td><td rowspan="1" colspan="1">0.0201 (9)</td><td rowspan="1" colspan="1">0.0238 (9)</td><td rowspan="1" colspan="1">0.0060 (8)</td><td rowspan="1" colspan="1">0.0054 (8)</td><td rowspan="1" colspan="1">0.0080 (8)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0196 (9)</td><td rowspan="1" colspan="1">0.0213 (9)</td><td rowspan="1" colspan="1">0.0160 (8)</td><td rowspan="1" colspan="1">0.0035 (7)</td><td rowspan="1" colspan="1">0.0054 (7)</td><td rowspan="1" colspan="1">0.0040 (7)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0181 (8)</td><td rowspan="1" colspan="1">0.0187 (9)</td><td rowspan="1" colspan="1">0.0209 (9)</td><td rowspan="1" colspan="1">0.0111 (7)</td><td rowspan="1" colspan="1">0.0059 (7)</td><td rowspan="1" colspan="1">0.0041 (7)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0418 (12)</td><td rowspan="1" colspan="1">0.0204 (9)</td><td rowspan="1" colspan="1">0.0283 (10)</td><td rowspan="1" colspan="1">0.0084 (9)</td><td rowspan="1" colspan="1">0.0156 (9)</td><td rowspan="1" colspan="1">0.0003 (8)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0190 (9)</td><td rowspan="1" colspan="1">0.0212 (9)</td><td rowspan="1" colspan="1">0.0213 (9)</td><td rowspan="1" colspan="1">0.0081 (7)</td><td rowspan="1" colspan="1">0.0052 (7)</td><td rowspan="1" colspan="1">0.0023 (7)</td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.0182 (9)</td><td rowspan="1" colspan="1">0.0231 (9)</td><td rowspan="1" colspan="1">0.0252 (9)</td><td rowspan="1" colspan="1">0.0068 (7)</td><td rowspan="1" colspan="1">0.0047 (7)</td><td rowspan="1" colspan="1">0.0066 (8)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0265 (10)</td><td rowspan="1" colspan="1">0.0217 (9)</td><td rowspan="1" colspan="1">0.0196 (9)</td><td rowspan="1" colspan="1">0.0109 (8)</td><td rowspan="1" colspan="1">0.0055 (7)</td><td rowspan="1" colspan="1">0.0085 (7)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.0248 (10)</td><td rowspan="1" colspan="1">0.0238 (9)</td><td rowspan="1" colspan="1">0.0256 (10)</td><td rowspan="1" colspan="1">0.0062 (8)</td><td rowspan="1" colspan="1">0.0090 (8)</td><td rowspan="1" colspan="1">0.0068 (8)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0301 (10)</td><td rowspan="1" colspan="1">0.0185 (9)</td><td rowspan="1" colspan="1">0.0221 (9)</td><td rowspan="1" colspan="1">0.0041 (8)</td><td rowspan="1" colspan="1">0.0114 (8)</td><td rowspan="1" colspan="1">0.0047 (7)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0390 (12)</td><td rowspan="1" colspan="1">0.0316 (11)</td><td rowspan="1" colspan="1">0.0200 (9)</td><td rowspan="1" colspan="1">0.0107 (9)</td><td rowspan="1" colspan="1">0.0046 (9)</td><td rowspan="1" colspan="1">0.0034 (8)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0330 (10)</td><td rowspan="1" colspan="1">0.0216 (9)</td><td rowspan="1" colspan="1">0.0180 (9)</td><td rowspan="1" colspan="1">0.0151 (8)</td><td rowspan="1" colspan="1">0.0061 (8)</td><td rowspan="1" colspan="1">0.0057 (7)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0289 (10)</td><td rowspan="1" colspan="1">0.0255 (10)</td><td rowspan="1" colspan="1">0.0270 (10)</td><td rowspan="1" colspan="1">0.0132 (8)</td><td rowspan="1" colspan="1">0.0043 (8)</td><td rowspan="1" colspan="1">0.0059 (8)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0346 (11)</td><td rowspan="1" colspan="1">0.0213 (9)</td><td rowspan="1" colspan="1">0.0199 (9)</td><td rowspan="1" colspan="1">0.0144 (8)</td><td rowspan="1" colspan="1">0.0069 (8)</td><td rowspan="1" colspan="1">0.0016 (7)</td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.0283 (10)</td><td rowspan="1" colspan="1">0.0366 (11)</td><td rowspan="1" colspan="1">0.0224 (10)</td><td rowspan="1" colspan="1">0.0131 (9)</td><td rowspan="1" colspan="1">0.0097 (8)</td><td rowspan="1" colspan="1">0.0117 (8)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0165 (8)</td><td rowspan="1" colspan="1">0.0139 (8)</td><td rowspan="1" colspan="1">0.0234 (9)</td><td rowspan="1" colspan="1">0.0029 (7)</td><td rowspan="1" colspan="1">0.0081 (7)</td><td rowspan="1" colspan="1">0.0030 (7)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.0277 (10)</td><td rowspan="1" colspan="1">0.0222 (9)</td><td rowspan="1" colspan="1">0.0285 (10)</td><td rowspan="1" colspan="1">0.0035 (8)</td><td rowspan="1" colspan="1">0.0000 (8)</td><td rowspan="1" colspan="1">−0.0017 (8)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0420 (12)</td><td rowspan="1" colspan="1">0.0205 (10)</td><td rowspan="1" colspan="1">0.0393 (12)</td><td rowspan="1" colspan="1">0.0154 (9)</td><td rowspan="1" colspan="1">0.0124 (10)</td><td rowspan="1" colspan="1">0.0098 (9)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0189 (9)</td><td rowspan="1" colspan="1">0.0179 (9)</td><td rowspan="1" colspan="1">0.0208 (9)</td><td rowspan="1" colspan="1">0.0070 (7)</td><td rowspan="1" colspan="1">0.0089 (7)</td><td rowspan="1" colspan="1">0.0026 (7)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0410 (12)</td><td rowspan="1" colspan="1">0.0410 (12)</td><td rowspan="1" colspan="1">0.0191 (10)</td><td rowspan="1" colspan="1">0.0146 (10)</td><td rowspan="1" colspan="1">0.0071 (9)</td><td rowspan="1" colspan="1">0.0124 (9)</td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.0347 (11)</td><td rowspan="1" colspan="1">0.0350 (11)</td><td rowspan="1" colspan="1">0.0169 (9)</td><td rowspan="1" colspan="1">0.0160 (9)</td><td rowspan="1" colspan="1">0.0022 (8)</td><td rowspan="1" colspan="1">0.0006 (8)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0547 (14)</td><td rowspan="1" colspan="1">0.0327 (11)</td><td rowspan="1" colspan="1">0.0196 (10)</td><td rowspan="1" colspan="1">0.0140 (10)</td><td rowspan="1" colspan="1">0.0148 (9)</td><td rowspan="1" colspan="1">0.0022 (8)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e2046"><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—O3</td><td rowspan="1" colspan="1">2.0224 (15)</td><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">Co1—O1</td><td rowspan="1" colspan="1">2.0382 (14)</td><td rowspan="1" colspan="1">C17—C16</td><td rowspan="1" colspan="1">1.519 (2)</td></tr><tr><td rowspan="1" colspan="1">Co1—O2<sup>i</sup></td><td rowspan="1" colspan="1">2.0429 (15)</td><td rowspan="1" colspan="1">C17—H17A</td><td rowspan="1" colspan="1">0.97</td></tr><tr><td rowspan="1" colspan="1">Co1—N2</td><td rowspan="1" colspan="1">2.0460 (16)</td><td rowspan="1" colspan="1">C17—H17B</td><td rowspan="1" colspan="1">0.97</td></tr><tr><td rowspan="1" colspan="1">Co1—O4<sup>i</sup></td><td rowspan="1" colspan="1">2.0628 (16)</td><td rowspan="1" colspan="1">C23—C22</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">Co1—Co1<sup>i</sup></td><td rowspan="1" colspan="1">2.8020 (12)</td><td rowspan="1" colspan="1">C23—H23</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">O1—C8</td><td rowspan="1" colspan="1">1.253 (2)</td><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">O3—C16</td><td rowspan="1" colspan="1">1.262 (2)</td><td rowspan="1" colspan="1">C19—C20</td><td rowspan="1" colspan="1">1.381 (3)</td></tr><tr><td rowspan="1" colspan="1">O2—C8</td><td rowspan="1" colspan="1">1.256 (2)</td><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">O2—Co1<sup>i</sup></td><td rowspan="1" colspan="1">2.0429 (15)</td><td rowspan="1" colspan="1">C9—C8</td><td rowspan="1" colspan="1">1.524 (2)</td></tr><tr><td rowspan="1" colspan="1">O4—C16</td><td rowspan="1" colspan="1">1.247 (2)</td><td rowspan="1" colspan="1">C9—H9A</td><td rowspan="1" colspan="1">0.97</td></tr><tr><td rowspan="1" colspan="1">O4—Co1<sup>i</sup></td><td rowspan="1" colspan="1">2.0628 (16)</td><td rowspan="1" colspan="1">C9—H9B</td><td rowspan="1" colspan="1">0.97</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.349 (2)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.381 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C6</td><td rowspan="1" colspan="1">1.453 (2)</td><td rowspan="1" colspan="1">C14—H14</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">N1—C7</td><td rowspan="1" colspan="1">1.454 (2)</td><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.366 (2)</td></tr><tr><td rowspan="1" colspan="1">N2—C3</td><td rowspan="1" colspan="1">1.343 (2)</td><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">N2—C4</td><td rowspan="1" colspan="1">1.345 (2)</td><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.383 (3)</td><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C10—C15</td><td rowspan="1" colspan="1">1.388 (3)</td><td rowspan="1" colspan="1">C22—C21</td><td rowspan="1" colspan="1">1.380 (3)</td></tr><tr><td rowspan="1" colspan="1">C10—C9</td><td rowspan="1" colspan="1">1.510 (2)</td><td rowspan="1" colspan="1">C22—H22</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C3—C2</td><td rowspan="1" colspan="1">1.369 (2)</td><td rowspan="1" colspan="1">C20—C21</td><td rowspan="1" colspan="1">1.384 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">C20—H20</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.387 (3)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">C7—H7A</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.410 (2)</td><td rowspan="1" colspan="1">C7—H7B</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C1—C5</td><td rowspan="1" colspan="1">1.411 (2)</td><td rowspan="1" colspan="1">C7—H7C</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C18—C23</td><td rowspan="1" colspan="1">1.386 (2)</td><td rowspan="1" colspan="1">C21—H21</td><td rowspan="1" colspan="1">0.93</td></tr><tr><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.388 (3)</td><td rowspan="1" colspan="1">C6—H6A</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C18—C17</td><td rowspan="1" colspan="1">1.506 (2)</td><td rowspan="1" colspan="1">C6—H6B</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C13—C12</td><td rowspan="1" colspan="1">1.380 (3)</td><td rowspan="1" colspan="1">C6—H6C</td><td rowspan="1" colspan="1">0.96</td></tr><tr><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.382 (3)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3—Co1—O1</td><td rowspan="1" colspan="1">93.27 (6)</td><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">O3—Co1—O2<sup>i</sup></td><td rowspan="1" colspan="1">87.33 (6)</td><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">O1—Co1—O2<sup>i</sup></td><td rowspan="1" colspan="1">163.77 (5)</td><td rowspan="1" colspan="1">C20—C19—C18</td><td rowspan="1" colspan="1">120.91 (17)</td></tr><tr><td rowspan="1" colspan="1">O3—Co1—N2</td><td rowspan="1" colspan="1">102.92 (6)</td><td rowspan="1" colspan="1">C20—C19—H19</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">O1—Co1—N2</td><td rowspan="1" colspan="1">94.29 (5)</td><td rowspan="1" colspan="1">C18—C19—H19</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">O2<sup>i</sup>—Co1—N2</td><td rowspan="1" colspan="1">101.39 (5)</td><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">114.21 (14)</td></tr><tr><td rowspan="1" colspan="1">O3—Co1—O4<sup>i</sup></td><td rowspan="1" colspan="1">163.73 (5)</td><td rowspan="1" colspan="1">C10—C9—H9A</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">O1—Co1—O4<sup>i</sup></td><td rowspan="1" colspan="1">85.64 (6)</td><td rowspan="1" colspan="1">C8—C9—H9A</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">O2<sup>i</sup>—Co1—O4<sup>i</sup></td><td rowspan="1" colspan="1">89.27 (7)</td><td rowspan="1" colspan="1">C10—C9—H9B</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">N2—Co1—O4<sup>i</sup></td><td rowspan="1" colspan="1">93.35 (5)</td><td rowspan="1" colspan="1">C8—C9—H9B</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">O3—Co1—Co1<sup>i</sup></td><td rowspan="1" colspan="1">89.34 (4)</td><td rowspan="1" colspan="1">H9A—C9—H9B</td><td rowspan="1" colspan="1">107.6</td></tr><tr><td rowspan="1" colspan="1">O1—Co1—Co1<sup>i</sup></td><td rowspan="1" colspan="1">79.04 (4)</td><td rowspan="1" colspan="1">C15—C14—C13</td><td rowspan="1" colspan="1">120.40 (18)</td></tr><tr><td rowspan="1" colspan="1">O2<sup>i</sup>—Co1—Co1<sup>i</sup></td><td rowspan="1" colspan="1">84.75 (4)</td><td rowspan="1" colspan="1">C15—C14—H14</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">N2—Co1—Co1<sup>i</sup></td><td rowspan="1" colspan="1">166.44 (4)</td><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">O4<sup>i</sup>—Co1—Co1<sup>i</sup></td><td rowspan="1" colspan="1">74.50 (4)</td><td rowspan="1" colspan="1">N2—C4—C5</td><td rowspan="1" colspan="1">124.16 (16)</td></tr><tr><td rowspan="1" colspan="1">C8—O1—Co1</td><td rowspan="1" colspan="1">129.17 (11)</td><td rowspan="1" colspan="1">N2—C4—H4</td><td rowspan="1" colspan="1">117.9</td></tr><tr><td rowspan="1" colspan="1">C16—O3—Co1</td><td rowspan="1" colspan="1">116.62 (11)</td><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">117.9</td></tr><tr><td rowspan="1" colspan="1">C8—O2—Co1<sup>i</sup></td><td rowspan="1" colspan="1">121.65 (11)</td><td rowspan="1" colspan="1">C14—C15—C10</td><td rowspan="1" colspan="1">120.78 (17)</td></tr><tr><td rowspan="1" colspan="1">C16—O4—Co1<sup>i</sup></td><td rowspan="1" colspan="1">133.30 (12)</td><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C6</td><td rowspan="1" colspan="1">120.56 (16)</td><td rowspan="1" colspan="1">C10—C15—H15</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C7</td><td rowspan="1" colspan="1">121.55 (16)</td><td rowspan="1" colspan="1">C4—C5—C1</td><td rowspan="1" colspan="1">120.39 (16)</td></tr><tr><td rowspan="1" colspan="1">C6—N1—C7</td><td rowspan="1" colspan="1">117.89 (15)</td><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C3—N2—C4</td><td rowspan="1" colspan="1">115.61 (15)</td><td rowspan="1" colspan="1">C1—C5—H5</td><td rowspan="1" colspan="1">119.8</td></tr><tr><td rowspan="1" colspan="1">C3—N2—Co1</td><td rowspan="1" colspan="1">124.00 (11)</td><td rowspan="1" colspan="1">C21—C22—C23</td><td rowspan="1" colspan="1">120.28 (18)</td></tr><tr><td rowspan="1" colspan="1">C4—N2—Co1</td><td rowspan="1" colspan="1">120.31 (11)</td><td rowspan="1" colspan="1">C21—C22—H22</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C11—C10—C15</td><td rowspan="1" colspan="1">118.12 (17)</td><td rowspan="1" colspan="1">C23—C22—H22</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C11—C10—C9</td><td rowspan="1" colspan="1">120.35 (16)</td><td rowspan="1" colspan="1">O4—C16—O3</td><td rowspan="1" colspan="1">125.35 (16)</td></tr><tr><td rowspan="1" colspan="1">C15—C10—C9</td><td rowspan="1" colspan="1">121.52 (16)</td><td rowspan="1" colspan="1">O4—C16—C17</td><td rowspan="1" colspan="1">118.12 (15)</td></tr><tr><td rowspan="1" colspan="1">N2—C3—C2</td><td rowspan="1" colspan="1">124.67 (16)</td><td rowspan="1" colspan="1">O3—C16—C17</td><td rowspan="1" colspan="1">116.52 (15)</td></tr><tr><td rowspan="1" colspan="1">N2—C3—H3</td><td rowspan="1" colspan="1">117.7</td><td rowspan="1" colspan="1">C19—C20—C21</td><td rowspan="1" colspan="1">120.23 (18)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">117.7</td><td rowspan="1" colspan="1">C19—C20—H20</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">121.52 (18)</td><td rowspan="1" colspan="1">C21—C20—H20</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">119.2</td><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">119.52 (18)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">119.2</td><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">120.2</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">122.71 (16)</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">120.2</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C5</td><td rowspan="1" colspan="1">122.05 (16)</td><td rowspan="1" colspan="1">O1—C8—O2</td><td rowspan="1" colspan="1">125.30 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C5</td><td rowspan="1" colspan="1">115.23 (16)</td><td rowspan="1" colspan="1">O1—C8—C9</td><td rowspan="1" colspan="1">117.19 (15)</td></tr><tr><td rowspan="1" colspan="1">C23—C18—C19</td><td rowspan="1" colspan="1">118.53 (16)</td><td rowspan="1" colspan="1">O2—C8—C9</td><td rowspan="1" colspan="1">117.50 (15)</td></tr><tr><td rowspan="1" colspan="1">C23—C18—C17</td><td rowspan="1" colspan="1">120.81 (16)</td><td rowspan="1" colspan="1">N1—C7—H7A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C19—C18—C17</td><td rowspan="1" colspan="1">120.66 (16)</td><td rowspan="1" colspan="1">N1—C7—H7B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C13—C14</td><td rowspan="1" colspan="1">119.66 (18)</td><td rowspan="1" colspan="1">H7A—C7—H7B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">120.2</td><td rowspan="1" colspan="1">N1—C7—H7C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">120.2</td><td rowspan="1" colspan="1">H7A—C7—H7C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C18—C17—C16</td><td rowspan="1" colspan="1">114.52 (14)</td><td rowspan="1" colspan="1">H7B—C7—H7C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C18—C17—H17A</td><td rowspan="1" colspan="1">108.6</td><td rowspan="1" colspan="1">C22—C21—C20</td><td rowspan="1" colspan="1">119.40 (17)</td></tr><tr><td rowspan="1" colspan="1">C16—C17—H17A</td><td rowspan="1" colspan="1">108.6</td><td rowspan="1" colspan="1">C22—C21—H21</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C18—C17—H17B</td><td rowspan="1" colspan="1">108.6</td><td rowspan="1" colspan="1">C20—C21—H21</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C16—C17—H17B</td><td rowspan="1" colspan="1">108.6</td><td rowspan="1" colspan="1">N1—C6—H6A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">H17A—C17—H17B</td><td rowspan="1" colspan="1">107.6</td><td rowspan="1" colspan="1">N1—C6—H6B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C18—C23—C22</td><td rowspan="1" colspan="1">120.65 (17)</td><td rowspan="1" colspan="1">H6A—C6—H6B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C18—C23—H23</td><td rowspan="1" colspan="1">119.7</td><td rowspan="1" colspan="1">N1—C6—H6C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C22—C23—H23</td><td rowspan="1" colspan="1">119.7</td><td rowspan="1" colspan="1">H6A—C6—H6C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">119.85 (16)</td><td rowspan="1" colspan="1">H6B—C6—H6C</td><td rowspan="1" colspan="1">109.5</td></tr></table></table-wrap><p>Symmetry code: (i) −<italic>x</italic>+1, −<italic>y</italic>, −<italic>z</italic>.</p></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e2895"><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">C6—H6<italic>A</italic>···O2<sup>ii</sup></td><td rowspan="1" colspan="1">0.96</td><td rowspan="1" colspan="1">2.53</td><td rowspan="1" colspan="1">3.337 (3)</td><td rowspan="1" colspan="1">142</td></tr><tr><td rowspan="1" colspan="1">C23—H23···O3<sup>iii</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.58</td><td rowspan="1" colspan="1">3.469 (3)</td><td rowspan="1" colspan="1">159</td></tr></table></table-wrap><p>Symmetry codes: (ii) <italic>x</italic>, <italic>y</italic>, <italic>z</italic>+1; (iii) −<italic>x</italic>+2, −<italic>y</italic>, −<italic>z</italic>.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). <italic>J. Appl. Cryst.</italic><bold>26</bold>, 343–350.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Araki, H., Tsuge, K., Sasaki, Y., Ishizaka, S. & Kitamura, N. (2005). <italic>Inorg. Chem.</italic><bold>44</bold>, 9667–9675.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Bruker (2012). <italic>APEX2</italic>, <italic>SAINT</italic> and <italic>SADABS</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Burnett, M. N. & Johnson, C. K. (1996). <italic>ORTEPIII</italic> Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Catterick, J. & Thornton, P. (1977). <italic>Adv. Inorg. Chem. Radiochem.</italic><bold>20</bold>, 291–362.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Cotton, F. A., Wilkinson, G., Murillo, C. A. & Bochmann, M. (1999). <italic>Advanced Inorganic Chemistry</italic>, 6th ed. Singapore: John Wiley & Sons.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Cui, Y., Long, D. L., Huang, X. Y., Zheng, F. K., Chen, W. D. & Huang, J. S. (1999). <italic>Chin. J. Struct. Chem.</italic><bold>19</bold>, 9–13.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Satgé, C., Granet, R., Verneuil, B., Branland, P. & Krausz, P. (2004). <italic>C. R. Chim.</italic><bold>7</bold>, 135–142.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref></ref-list></back><floats-group><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (Å, °)</title></caption><table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th></tr></thead><tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C6—H6<italic>A</italic>⋯O2<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.96</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.53</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.337 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">142</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C23—H23⋯O3<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.58</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.469 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">159</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-69-0m517-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-69-0m517-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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