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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Poly[[diaquabis(μ<sub>2</sub>
-4,4′-bipyridyl)cobalt(II)] dinitrate tetrahydrate]</title>
<author><name sortKey="Lehleh, Asma" sort="Lehleh, Asma" uniqKey="Lehleh A" first="Asma" last="Lehleh">Asma Lehleh</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Boutebdja, Mehdi" sort="Boutebdja, Mehdi" uniqKey="Boutebdja M" first="Mehdi" last="Boutebdja">Mehdi Boutebdja</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Beghidja, Adel" sort="Beghidja, Adel" uniqKey="Beghidja A" first="Adel" last="Beghidja">Adel Beghidja</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Beghidja, Chahrazed" sort="Beghidja, Chahrazed" uniqKey="Beghidja C" first="Chahrazed" last="Beghidja">Chahrazed Beghidja</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</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 (CHEMS), 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">23633984</idno>
<idno type="pmc">3629466</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629466</idno>
<idno type="RBID">PMC:3629466</idno>
<idno type="doi">10.1107/S1600536813005230</idno>
<date when="2013">2013</date>
<idno type="wicri:Area/Pmc/Corpus">000364</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000364</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Poly[[diaquabis(μ<sub>2</sub>
-4,4′-bipyridyl)cobalt(II)] dinitrate tetrahydrate]</title>
<author><name sortKey="Lehleh, Asma" sort="Lehleh, Asma" uniqKey="Lehleh A" first="Asma" last="Lehleh">Asma Lehleh</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Boutebdja, Mehdi" sort="Boutebdja, Mehdi" uniqKey="Boutebdja M" first="Mehdi" last="Boutebdja">Mehdi Boutebdja</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Beghidja, Adel" sort="Beghidja, Adel" uniqKey="Beghidja A" first="Adel" last="Beghidja">Adel Beghidja</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Beghidja, Chahrazed" sort="Beghidja, Chahrazed" uniqKey="Beghidja C" first="Chahrazed" last="Beghidja">Chahrazed Beghidja</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</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 (CHEMS), 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(C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
](NO<sub>3</sub>
)<sub>2</sub>
·4H<sub>2</sub>
O}<sub><italic>n</italic>
</sub>
, (C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
= 4,4′-bipyridine = 4,4′-bpy) is a layered coordination polymer built up from a cationic square grid extending in (101) enclosing uncoordinating nitrate ions and water molecules. The Co<sup>II</sup>
ion has site symmetry 2 and one of the 4,4′-bpy ligands is generated by twofold symmetry [two N atoms and two C atoms lie on the rotation axis and the dihedral angle between the pyridine rings is 45.66 (5)°]. The other 4,4′-bpy ligand is generated by a crystallographic inversion center. The Co<sup>II</sup>
ion exhibits a slightly distorted octahedral coordination geometry defined by two O atoms of two coordinating water molecules and four N atoms from four bridging 4,4′-bpy ligands. The structure is consolidated by O—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
</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">23633984</article-id>
<article-id pub-id-type="pmc">3629466</article-id>
<article-id pub-id-type="publisher-id">hb7035</article-id>
<article-id pub-id-type="doi">10.1107/S1600536813005230</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536813005230</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Metal-Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>Poly[[diaquabis(μ<sub>2</sub>
-4,4′-bipyridyl)cobalt(II)] dinitrate tetrahydrate]</article-title>
<alt-title><italic>[Co(C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
](NO<sub>3</sub>
)<sub>2</sub>
·4H<sub>2</sub>
O</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Lehleh</surname>
<given-names>Asma</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Boutebdja</surname>
<given-names>Mehdi</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Beghidja</surname>
<given-names>Adel</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>Beghidja</surname>
<given-names>Chahrazed</given-names>
</name>
<xref ref-type="aff" rid="a">a</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 (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine,<country>Algeria</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>a_beghidja@yahoo.fr</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>4</month>
<year>2013</year>
</pub-date>
<pub-date pub-type="epub"><day>02</day>
<month>3</month>
<year>2013</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>02</day>
<month>3</month>
<year>2013</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
. </pmc-comment>
<volume>69</volume>
<issue>Pt 4</issue>
<issue-id pub-id-type="publisher-id">e130400</issue-id>
<fpage>m177</fpage>
<lpage>m178</lpage>
<history><date date-type="received"><day>04</day>
<month>2</month>
<year>2013</year>
</date>
<date date-type="accepted"><day>23</day>
<month>2</month>
<year>2013</year>
</date>
</history>
<permissions><copyright-statement>© Lehleh 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/S1600536813005230">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>The title compound, {[Co(C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
](NO<sub>3</sub>
)<sub>2</sub>
·4H<sub>2</sub>
O}<sub><italic>n</italic>
</sub>
, (C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
= 4,4′-bipyridine = 4,4′-bpy) is a layered coordination polymer built up from a cationic square grid extending in (101) enclosing uncoordinating nitrate ions and water molecules. The Co<sup>II</sup>
ion has site symmetry 2 and one of the 4,4′-bpy ligands is generated by twofold symmetry [two N atoms and two C atoms lie on the rotation axis and the dihedral angle between the pyridine rings is 45.66 (5)°]. The other 4,4′-bpy ligand is generated by a crystallographic inversion center. The Co<sup>II</sup>
ion exhibits a slightly distorted octahedral coordination geometry defined by two O atoms of two coordinating water molecules and four N atoms from four bridging 4,4′-bpy ligands. The structure is consolidated by O—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds.</p>
</abstract>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature
</title>
<p>For related structures with 4,4′-bpy ligands, see: Aoyagi <italic>et al.</italic>
(2000<xref ref-type="bibr" rid="bb1"> ▶</xref>
); Felloni <italic>et al.</italic>
(2002<xref ref-type="bibr" rid="bb5"> ▶</xref>
); Jin <italic>et al.</italic>
(2006<xref ref-type="bibr" rid="bb6"> ▶</xref>
); Tong <italic>et al.</italic>
(2000<xref ref-type="bibr" rid="bb8"> ▶</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-69-0m177-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(C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
](NO<sub>3</sub>
)<sub>2</sub>
·4H<sub>2</sub>
O</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 603.41</p>
</list-item>
<list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-69-0m177-efi6.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
= 18.6093 (19) Å</p>
</list-item>
<list-item><p><italic>b</italic>
= 11.5447 (13) Å</p>
</list-item>
<list-item><p><italic>c</italic>
= 12.1216 (13) Å</p>
</list-item>
<list-item><p>β = 95.625 (4)°</p>
</list-item>
<list-item><p><italic>V</italic>
= 2591.7 (5) Å<sup>3</sup>
</p>
</list-item>
<list-item><p><italic>Z</italic>
= 4</p>
</list-item>
<list-item><p>Mo <italic>K</italic>
α radiation</p>
</list-item>
<list-item><p>μ = 0.74 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
= 296 K</p>
</list-item>
<list-item><p>0.15 × 0.12 × 0.10 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>18421 measured reflections</p>
</list-item>
<list-item><p>3942 independent reflections</p>
</list-item>
<list-item><p>3660 reflections with <italic>I</italic>
> 2σ(<italic>I</italic>
)</p>
</list-item>
<list-item><p><italic>R</italic>
<sub>int</sub>
= 0.016</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>
)] = 0.030</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.083</p>
</list-item>
<list-item><p><italic>S</italic>
= 1.05</p>
</list-item>
<list-item><p>3942 reflections</p>
</list-item>
<list-item><p>198 parameters</p>
</list-item>
<list-item><p>9 restraints</p>
</list-item>
<list-item><p>H atoms treated by a mixture of independent and constrained refinement</p>
</list-item>
<list-item><p>Δρ<sub>max</sub>
= 0.41 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
= −0.49 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
</sec>
<sec id="d5e740"><title></title>
<p>Data collection: <italic>APEX2</italic>
(Bruker, 2006<xref ref-type="bibr" rid="bb2"> ▶</xref>
); cell refinement: <italic>SAINT</italic>
(Bruker, 2006<xref ref-type="bibr" rid="bb2"> ▶</xref>
); data reduction: <italic>SAINT</italic>
; program(s) used to solve structure: <italic>SHELXS97</italic>
(Sheldrick, 2008<xref ref-type="bibr" rid="bb7"> ▶</xref>
); program(s) used to refine structure: <italic>SHELXL97</italic>
(Sheldrick, 2008<xref ref-type="bibr" rid="bb7"> ▶</xref>
); molecular graphics: <italic>ATOMS</italic>
(Dowty, 1995<xref ref-type="bibr" rid="bb3"> ▶</xref>
); software used to prepare material for publication: <italic>WinGX</italic>
(Farrugia, 2012<xref ref-type="bibr" rid="bb4"> ▶</xref>
).</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data"><media xlink:href="e-69-0m177-sup1.cif" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Crystal structure: contains datablock(s) global, I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536813005230/hb7035sup1.cif">10.1107/S1600536813005230/hb7035sup1.cif</ext-link>
</p>
<media xlink:href="e-69-0m177-sup1.cif" xlink:type="simple" id="d35e154" position="anchor" mimetype="text" mime-subtype="plain"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-69-0m177-Isup2.hkl" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536813005230/hb7035Isup2.hkl">10.1107/S1600536813005230/hb7035Isup2.hkl</ext-link>
</p>
<media xlink:href="e-69-0m177-Isup2.hkl" xlink:type="simple" id="d35e161" position="anchor" mimetype="text" mime-subtype="plain"></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?hb7035&file=hb7035sup0.html&mime=text/html"> crystallographic information</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?hb7035sup1&Qmime=cif">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hb7035&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?hb7035">HB7035</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>The authors thank the MESRS (Algeria) for financial support. AL thanks the DG–RSDT and ANDRU (Direction Générale de la Recherche Scientifique et du Développement Technologique et l’Agence Nationale pour le Développement de la Recherche Universitaire, Algeria) for support through the PNR project.</p>
</ack>
<app-group><app><title>supplementary crystallographic
information</title>
<sec id="comment"><title>Comment </title>
<p>The structure of (I) is a two dimensional layer with no interpenetration and no
enclathration of organic guest molecules. The Co<sup>II</sup>
atom being located on a
twofold crystallographic axis, has slightly distorted octahedral geometry,
being ligated by two aqua ligands [Co—O1w = 2.074 (10) Å] and four pyridil
groups from 4,4'-bpy ligands (Fig. 1), with a distance Co—N in the range of
2.1898 (13) - 2.2306 (14) Å which is almost similar to that observed in
{[{Co(H<sub>2</sub>
O)<sub>2</sub>
}(µ-4,4'-bpy)<sub>2</sub>
][NO<sub>3</sub>
]<sub>2</sub>
. 2(4,4'-bpy).2H<sub>2</sub>
O}<sub>n</sub>
;
{[{Co(H<sub>2</sub>
O)<sub>2</sub>
(4,4'-bpy)<sub>2</sub>
}(µ-4,4'-bpy)]. 1.5[NO<sub>3</sub>
].0.5OH.
2(4,4'-bpy).2.5H<sub>2</sub>
O}<sub>n</sub>
, Felloni <italic>et al.</italic>
(2002) and
{[Co(µ-4,4'-bpy)(4,4'-bpy)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
].(OH)<sub>3</sub>
.(NMe<sub>4</sub>
).4,4'-bpy.4H<sub>2</sub>
O}<sub>n</sub>
,
Jin <italic>et al.</italic>
(2006), these last act as a bidentate bridging
ligands
giving rise to a 2-D square grid sheet of (4,4) topology lying in the (101)
plane. The basal coordinated 4,4'-bpy is located on an inversion center, it is
planar with a 0° interplanar angle between the two pyridil rings, the same
thing is observed in {[Cd(4,4'-bpy)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
]. (NO<sub>3</sub>
)<sub>2</sub>
.4H<sub>2</sub>
O}<sub>n</sub>
,
Aoyagi <italic>et al.</italic>
(2000), whereas the axially one is nonplanar with
an
angle of 45.60° between the pyridil rings. The dihedral angle between the two
basal coordinated 4,4'-bpy molecules is 46.92°. Each layer features a
perfectly planar, though slightly distorted, square with Co(II) atom and
4,4'-bpy at each corner and side, respectively (<italic>cis</italic>
N—Co—N =
88.64 (2)°, 91.37 (2)°) (Fig. 2). The square cavity has dimensions of 11.54
× 11.59 Å, which are comparable to those of closely related compound
{[Cd(4,4'-bpy)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
].(NO<sub>3</sub>
)<sub>2</sub>
.2H<sub>2</sub>
O}<sub>n</sub>
, Tong <italic>et al.</italic>
(2000).
The nitrate ion and lattice water molecules are situated between the
coordination layers and form extensive hydrogen bonds among the aqua ligands,
4,4'-bpy, uncoordinated water molecules and nitrate ion, which extend the
two-dimensional coordination layers into a three-dimensional molecular network
(Fig. 3).</p>
</sec>
<sec id="experimental"><title>Experimental </title>
<p>A mixture of Co(NO<sub>3</sub>
)2. 6H<sub>2</sub>
O (0.291 g, 1 mmole), <italic>trans</italic>
-cinnamic acid
(0.148 g, 1 mmole), NaOH (0.04 g, 1 mmole) and 4,4'-bpy (0.156 g, 1 mmole)
were dissolved with 10 ml of mixed solution (MeOH/H<sub>2</sub>
O: 2/1) in a 20 ml
Teflon-lined stainless steel reactor and heated to 120°C for 24 h. The
reactor was cooled to room temperature over a period of 24 h, the reaction was
filtered. The orange filtrate was kept for several weeks at room temperature.
Orange crystals suitable for X-ray analysis were obtained.
Note: the measured crystal is a fragment cut from a larger crystal.</p>
</sec>
<sec id="refinement"><title>Refinement </title>
<p>Water hydrogen atoms were tentatively found in the difference density Fourier
map and were refined with an isotropic displacement parameter 1.5 that of the
adjacent oxygen atom. The O—H distances were restrained to be 0.9 Å within
a standard deviation of 0.01 with <italic>U</italic>
<sub>iso</sub>
(H) = 1.5 <italic>U</italic>
<sub>eq</sub>
(O) and
the H···H contacts were restraint to 1.40 Å with a standard deviation of
0.02. A l l other Hydrogen atoms were placed in calculated positions with C
—H distances of 0.93–0.96 Å for aromatic H atoms with <italic>U</italic>
<sub>iso</sub>
(H)
=1.2 <italic>U</italic>
<sub>eq</sub>
(C).</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>View of a fragment of the title compound with displacement ellipsoids for non-H atoms are drawn at the 50% probability level. symmetry code: i = x,-1 + y,z; ii = x,1 + y,z; iii = 1 - x,-1 + y,1/2 - z; iv = 1 - x,y,1/2 - z; vi = 3/2 - x,1/2 - y,-z; vii = 1/2 + x,-1/2 - y,-1/2 + z; xii = 3/2 - x,1/2 - y,1/2 - z</p>
</caption>
<graphic xlink:href="e-69-0m177-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>ATOMS view of the square grids of the title compound</p>
</caption>
<graphic xlink:href="e-69-0m177-fig2"></graphic>
</fig>
<fig id="Fap3"><label>Fig. 3.</label>
<caption><p>Partial view of the crystal structure of the title compound showing the hydrogen bonds</p>
</caption>
<graphic xlink:href="e-69-0m177-fig3"></graphic>
</fig>
</sec>
<sec id="tablewrapcrystaldatalong"><title>Crystal data</title>
<table-wrap position="anchor" id="d1e333"><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(C<sub>10</sub>
H<sub>8</sub>
N<sub>2</sub>
)<sub>2</sub>
(H<sub>2</sub>
O)<sub>2</sub>
](NO<sub>3</sub>
)<sub>2</sub>
·4H<sub>2</sub>
O</td>
<td rowspan="1" colspan="1"><italic>Z</italic>
= 4</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 603.41</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 1252</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>C</italic>
2/<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Least Squares Treatment of 25 SET4 setting angles.</td>
</tr>
<tr><td rowspan="1" colspan="1">Hall symbol: -C 2yc</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
= 1.546 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
= 18.6093 (19) Å</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>b</italic>
= 11.5447 (13) Å</td>
<td rowspan="1" colspan="1">µ = 0.74 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
= 12.1216 (13) Å</td>
<td rowspan="1" colspan="1"><italic>T</italic>
= 296 K</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 95.625 (4)°</td>
<td rowspan="1" colspan="1">Block, orange</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
= 2591.7 (5) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.15 × 0.12 × 0.10 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapdatacollectionlong"><title>Data collection</title>
<table-wrap position="anchor" id="d1e471"><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">3660 reflections with <italic>I</italic>
> 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: sealed tube</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
= 0.016</td>
</tr>
<tr><td rowspan="1" colspan="1">Graphite monochromator</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
= 30.5°, θ<sub>min</sub>
= 3.7°</td>
</tr>
<tr><td rowspan="1" colspan="1">Detector resolution: 18.4 pixels mm<sup>-1</sup>
</td>
<td rowspan="1" colspan="1"><italic>h</italic>
= −26→26</td>
</tr>
<tr><td rowspan="1" colspan="1">φ and ω scans</td>
<td rowspan="1" colspan="1"><italic>k</italic>
= −16→12</td>
</tr>
<tr><td rowspan="1" colspan="1">18421 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
= −15→17</td>
</tr>
<tr><td rowspan="1" colspan="1">3942 independent reflections</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraprefinementdatalong"><title>Refinement</title>
<table-wrap position="anchor" id="d1e575"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
> 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.030</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.083</td>
<td rowspan="1" colspan="1"><italic>w</italic>
= 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0411<italic>P</italic>
)<sup>2</sup>
+ 2.4609<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>S</italic>
= 1.05</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
= 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1">3942 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
= 0.41 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">198 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
= −0.49 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">9 restraints</td>
<td rowspan="1" colspan="1">Extinction correction: <italic>SHELXL97</italic>
(Sheldrick, 2008), FC<sup>*</sup>
=KFC[1+0.001XFC<sup>2</sup>
Λ<sup>3</sup>
/SIN(2Θ)]<sup>-1/4</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1">Extinction coefficient: 0.0058 (4)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e756"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. Bond distances, angles <italic>etc</italic>
. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles</td>
</tr>
<tr><td rowspan="1" colspan="1">Refinement. Refinement on <italic>F</italic>
<sup>2</sup>
for ALL reflections except those flagged by the user
for potential systematic errors. Weighted <italic>R</italic>
-factors <italic>wR</italic>
and all
goodnesses 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 observed criterion of <italic>F</italic>
<sup>2</sup>
> σ(<italic>F</italic>
<sup>2</sup>
)
is used only for calculating -<italic>R</italic>
-factor-obs <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="d1e858"><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">0.50000</td>
<td rowspan="1" colspan="1">0.74238 (2)</td>
<td rowspan="1" colspan="1">0.75000</td>
<td rowspan="1" colspan="1">0.0160 (1)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1W</td>
<td rowspan="1" colspan="1">0.56526 (5)</td>
<td rowspan="1" colspan="1">0.74192 (8)</td>
<td rowspan="1" colspan="1">0.89887 (8)</td>
<td rowspan="1" colspan="1">0.0261 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.59538 (5)</td>
<td rowspan="1" colspan="1">0.74697 (8)</td>
<td rowspan="1" colspan="1">0.65303 (8)</td>
<td rowspan="1" colspan="1">0.0194 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.50000</td>
<td rowspan="1" colspan="1">0.93206 (11)</td>
<td rowspan="1" colspan="1">0.75000</td>
<td rowspan="1" colspan="1">0.0198 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.50000</td>
<td rowspan="1" colspan="1">1.54917 (12)</td>
<td rowspan="1" colspan="1">0.75000</td>
<td rowspan="1" colspan="1">0.0216 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.59232 (6)</td>
<td rowspan="1" colspan="1">0.70962 (12)</td>
<td rowspan="1" colspan="1">0.54799 (10)</td>
<td rowspan="1" colspan="1">0.0261 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.65075 (7)</td>
<td rowspan="1" colspan="1">0.71019 (13)</td>
<td rowspan="1" colspan="1">0.48560 (10)</td>
<td rowspan="1" colspan="1">0.0286 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.71766 (6)</td>
<td rowspan="1" colspan="1">0.75068 (9)</td>
<td rowspan="1" colspan="1">0.53140 (10)</td>
<td rowspan="1" colspan="1">0.0196 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.72032 (7)</td>
<td rowspan="1" colspan="1">0.79164 (13)</td>
<td rowspan="1" colspan="1">0.63952 (11)</td>
<td rowspan="1" colspan="1">0.0289 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.65925 (7)</td>
<td rowspan="1" colspan="1">0.78805 (12)</td>
<td rowspan="1" colspan="1">0.69653 (11)</td>
<td rowspan="1" colspan="1">0.0282 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.48157 (7)</td>
<td rowspan="1" colspan="1">0.99302 (10)</td>
<td rowspan="1" colspan="1">0.83731 (10)</td>
<td rowspan="1" colspan="1">0.0229 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.48067 (7)</td>
<td rowspan="1" colspan="1">1.11296 (10)</td>
<td rowspan="1" colspan="1">0.84048 (10)</td>
<td rowspan="1" colspan="1">0.0237 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.50000</td>
<td rowspan="1" colspan="1">1.17564 (13)</td>
<td rowspan="1" colspan="1">0.75000</td>
<td rowspan="1" colspan="1">0.0189 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.50000</td>
<td rowspan="1" colspan="1">1.30435 (13)</td>
<td rowspan="1" colspan="1">0.75000</td>
<td rowspan="1" colspan="1">0.0191 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.55676 (7)</td>
<td rowspan="1" colspan="1">1.36752 (10)</td>
<td rowspan="1" colspan="1">0.71325 (11)</td>
<td rowspan="1" colspan="1">0.0266 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.55528 (7)</td>
<td rowspan="1" colspan="1">1.48777 (10)</td>
<td rowspan="1" colspan="1">0.71687 (12)</td>
<td rowspan="1" colspan="1">0.0277 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.73251 (11)</td>
<td rowspan="1" colspan="1">1.0878 (2)</td>
<td rowspan="1" colspan="1">0.67235 (12)</td>
<td rowspan="1" colspan="1">0.0843 (7)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.67234 (8)</td>
<td rowspan="1" colspan="1">1.07423 (15)</td>
<td rowspan="1" colspan="1">0.81345 (14)</td>
<td rowspan="1" colspan="1">0.0629 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.77569 (8)</td>
<td rowspan="1" colspan="1">0.99156 (14)</td>
<td rowspan="1" colspan="1">0.81568 (13)</td>
<td rowspan="1" colspan="1">0.0614 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.72726 (8)</td>
<td rowspan="1" colspan="1">1.05039 (14)</td>
<td rowspan="1" colspan="1">0.76769 (11)</td>
<td rowspan="1" colspan="1">0.0436 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2W</td>
<td rowspan="1" colspan="1">0.63340 (8)</td>
<td rowspan="1" colspan="1">1.06829 (14)</td>
<td rowspan="1" colspan="1">0.48099 (11)</td>
<td rowspan="1" colspan="1">0.0546 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3W</td>
<td rowspan="1" colspan="1">0.84438 (9)</td>
<td rowspan="1" colspan="1">1.06853 (16)</td>
<td rowspan="1" colspan="1">0.53876 (15)</td>
<td rowspan="1" colspan="1">0.0701 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1</td>
<td rowspan="1" colspan="1">0.54840</td>
<td rowspan="1" colspan="1">0.68170</td>
<td rowspan="1" colspan="1">0.51520</td>
<td rowspan="1" colspan="1">0.0310*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2</td>
<td rowspan="1" colspan="1">0.64530</td>
<td rowspan="1" colspan="1">0.68350</td>
<td rowspan="1" colspan="1">0.41290</td>
<td rowspan="1" colspan="1">0.0340*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4</td>
<td rowspan="1" colspan="1">0.76320</td>
<td rowspan="1" colspan="1">0.82160</td>
<td rowspan="1" colspan="1">0.67380</td>
<td rowspan="1" colspan="1">0.0350*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H5</td>
<td rowspan="1" colspan="1">0.66290</td>
<td rowspan="1" colspan="1">0.81570</td>
<td rowspan="1" colspan="1">0.76890</td>
<td rowspan="1" colspan="1">0.0340*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H6</td>
<td rowspan="1" colspan="1">0.46880</td>
<td rowspan="1" colspan="1">0.95260</td>
<td rowspan="1" colspan="1">0.89880</td>
<td rowspan="1" colspan="1">0.0280*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7</td>
<td rowspan="1" colspan="1">0.46720</td>
<td rowspan="1" colspan="1">1.15130</td>
<td rowspan="1" colspan="1">0.90270</td>
<td rowspan="1" colspan="1">0.0280*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10</td>
<td rowspan="1" colspan="1">0.59550</td>
<td rowspan="1" colspan="1">1.32940</td>
<td rowspan="1" colspan="1">0.68640</td>
<td rowspan="1" colspan="1">0.0320*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11</td>
<td rowspan="1" colspan="1">0.59480</td>
<td rowspan="1" colspan="1">1.52800</td>
<td rowspan="1" colspan="1">0.69510</td>
<td rowspan="1" colspan="1">0.0330*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H12</td>
<td rowspan="1" colspan="1">0.5930 (7)</td>
<td rowspan="1" colspan="1">0.6840 (9)</td>
<td rowspan="1" colspan="1">0.9229 (13)</td>
<td rowspan="1" colspan="1">0.0240*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H13</td>
<td rowspan="1" colspan="1">0.5878 (8)</td>
<td rowspan="1" colspan="1">0.8051 (9)</td>
<td rowspan="1" colspan="1">0.9250 (13)</td>
<td rowspan="1" colspan="1">0.0240*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H14</td>
<td rowspan="1" colspan="1">0.6676 (7)</td>
<td rowspan="1" colspan="1">1.0786 (14)</td>
<td rowspan="1" colspan="1">0.5353 (10)</td>
<td rowspan="1" colspan="1">0.0240*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15</td>
<td rowspan="1" colspan="1">0.6542 (8)</td>
<td rowspan="1" colspan="1">1.0272 (13)</td>
<td rowspan="1" colspan="1">0.4316 (10)</td>
<td rowspan="1" colspan="1">0.0240*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16</td>
<td rowspan="1" colspan="1">0.8124 (7)</td>
<td rowspan="1" colspan="1">1.0682 (15)</td>
<td rowspan="1" colspan="1">0.5868 (10)</td>
<td rowspan="1" colspan="1">0.0240*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H17</td>
<td rowspan="1" colspan="1">0.8192 (8)</td>
<td rowspan="1" colspan="1">1.0679 (15)</td>
<td rowspan="1" colspan="1">0.4727 (8)</td>
<td rowspan="1" colspan="1">0.0240*</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="d1e1329"><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">0.0164 (1)</td>
<td rowspan="1" colspan="1">0.0132 (1)</td>
<td rowspan="1" colspan="1">0.0193 (1)</td>
<td rowspan="1" colspan="1">0.0000</td>
<td rowspan="1" colspan="1">0.0057 (1)</td>
<td rowspan="1" colspan="1">0.0000</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W</td>
<td rowspan="1" colspan="1">0.0236 (4)</td>
<td rowspan="1" colspan="1">0.0290 (5)</td>
<td rowspan="1" colspan="1">0.0255 (4)</td>
<td rowspan="1" colspan="1">0.0002 (3)</td>
<td rowspan="1" colspan="1">0.0014 (3)</td>
<td rowspan="1" colspan="1">0.0015 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0188 (4)</td>
<td rowspan="1" colspan="1">0.0167 (4)</td>
<td rowspan="1" colspan="1">0.0240 (5)</td>
<td rowspan="1" colspan="1">−0.0001 (3)</td>
<td rowspan="1" colspan="1">0.0084 (3)</td>
<td rowspan="1" colspan="1">−0.0002 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.0233 (6)</td>
<td rowspan="1" colspan="1">0.0136 (5)</td>
<td rowspan="1" colspan="1">0.0232 (6)</td>
<td rowspan="1" colspan="1">0.0000</td>
<td rowspan="1" colspan="1">0.0060 (5)</td>
<td rowspan="1" colspan="1">0.0000</td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.0222 (6)</td>
<td rowspan="1" colspan="1">0.0148 (6)</td>
<td rowspan="1" colspan="1">0.0282 (7)</td>
<td rowspan="1" colspan="1">0.0000</td>
<td rowspan="1" colspan="1">0.0046 (5)</td>
<td rowspan="1" colspan="1">0.0000</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0183 (5)</td>
<td rowspan="1" colspan="1">0.0369 (6)</td>
<td rowspan="1" colspan="1">0.0238 (5)</td>
<td rowspan="1" colspan="1">−0.0031 (4)</td>
<td rowspan="1" colspan="1">0.0053 (4)</td>
<td rowspan="1" colspan="1">−0.0024 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0208 (5)</td>
<td rowspan="1" colspan="1">0.0456 (7)</td>
<td rowspan="1" colspan="1">0.0203 (5)</td>
<td rowspan="1" colspan="1">−0.0038 (5)</td>
<td rowspan="1" colspan="1">0.0062 (4)</td>
<td rowspan="1" colspan="1">−0.0054 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0175 (5)</td>
<td rowspan="1" colspan="1">0.0210 (5)</td>
<td rowspan="1" colspan="1">0.0215 (5)</td>
<td rowspan="1" colspan="1">−0.0001 (4)</td>
<td rowspan="1" colspan="1">0.0075 (4)</td>
<td rowspan="1" colspan="1">−0.0002 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0213 (5)</td>
<td rowspan="1" colspan="1">0.0377 (7)</td>
<td rowspan="1" colspan="1">0.0291 (6)</td>
<td rowspan="1" colspan="1">−0.0080 (5)</td>
<td rowspan="1" colspan="1">0.0095 (4)</td>
<td rowspan="1" colspan="1">−0.0131 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0246 (5)</td>
<td rowspan="1" colspan="1">0.0341 (6)</td>
<td rowspan="1" colspan="1">0.0278 (6)</td>
<td rowspan="1" colspan="1">−0.0069 (5)</td>
<td rowspan="1" colspan="1">0.0116 (4)</td>
<td rowspan="1" colspan="1">−0.0125 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0321 (6)</td>
<td rowspan="1" colspan="1">0.0160 (5)</td>
<td rowspan="1" colspan="1">0.0219 (5)</td>
<td rowspan="1" colspan="1">−0.0013 (4)</td>
<td rowspan="1" colspan="1">0.0090 (4)</td>
<td rowspan="1" colspan="1">0.0009 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0344 (6)</td>
<td rowspan="1" colspan="1">0.0160 (5)</td>
<td rowspan="1" colspan="1">0.0220 (5)</td>
<td rowspan="1" colspan="1">−0.0016 (4)</td>
<td rowspan="1" colspan="1">0.0099 (4)</td>
<td rowspan="1" colspan="1">−0.0022 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0210 (6)</td>
<td rowspan="1" colspan="1">0.0135 (6)</td>
<td rowspan="1" colspan="1">0.0227 (7)</td>
<td rowspan="1" colspan="1">0.0000</td>
<td rowspan="1" colspan="1">0.0042 (5)</td>
<td rowspan="1" colspan="1">0.0000</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0232 (7)</td>
<td rowspan="1" colspan="1">0.0132 (6)</td>
<td rowspan="1" colspan="1">0.0211 (6)</td>
<td rowspan="1" colspan="1">0.0000</td>
<td rowspan="1" colspan="1">0.0032 (5)</td>
<td rowspan="1" colspan="1">0.0000</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0257 (5)</td>
<td rowspan="1" colspan="1">0.0161 (5)</td>
<td rowspan="1" colspan="1">0.0401 (7)</td>
<td rowspan="1" colspan="1">0.0027 (4)</td>
<td rowspan="1" colspan="1">0.0136 (5)</td>
<td rowspan="1" colspan="1">0.0021 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.0256 (5)</td>
<td rowspan="1" colspan="1">0.0168 (5)</td>
<td rowspan="1" colspan="1">0.0428 (7)</td>
<td rowspan="1" colspan="1">−0.0001 (4)</td>
<td rowspan="1" colspan="1">0.0133 (5)</td>
<td rowspan="1" colspan="1">0.0036 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0952 (13)</td>
<td rowspan="1" colspan="1">0.1202 (16)</td>
<td rowspan="1" colspan="1">0.0372 (7)</td>
<td rowspan="1" colspan="1">−0.0386 (12)</td>
<td rowspan="1" colspan="1">0.0056 (7)</td>
<td rowspan="1" colspan="1">0.0049 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0435 (7)</td>
<td rowspan="1" colspan="1">0.0741 (10)</td>
<td rowspan="1" colspan="1">0.0729 (10)</td>
<td rowspan="1" colspan="1">−0.0014 (7)</td>
<td rowspan="1" colspan="1">0.0144 (6)</td>
<td rowspan="1" colspan="1">0.0011 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.0455 (7)</td>
<td rowspan="1" colspan="1">0.0733 (10)</td>
<td rowspan="1" colspan="1">0.0632 (9)</td>
<td rowspan="1" colspan="1">0.0023 (7)</td>
<td rowspan="1" colspan="1">−0.0057 (6)</td>
<td rowspan="1" colspan="1">−0.0158 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.0410 (7)</td>
<td rowspan="1" colspan="1">0.0553 (8)</td>
<td rowspan="1" colspan="1">0.0341 (6)</td>
<td rowspan="1" colspan="1">−0.0193 (6)</td>
<td rowspan="1" colspan="1">0.0017 (5)</td>
<td rowspan="1" colspan="1">−0.0078 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W</td>
<td rowspan="1" colspan="1">0.0554 (8)</td>
<td rowspan="1" colspan="1">0.0676 (9)</td>
<td rowspan="1" colspan="1">0.0402 (6)</td>
<td rowspan="1" colspan="1">0.0282 (7)</td>
<td rowspan="1" colspan="1">0.0015 (5)</td>
<td rowspan="1" colspan="1">0.0039 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3W</td>
<td rowspan="1" colspan="1">0.0645 (10)</td>
<td rowspan="1" colspan="1">0.0731 (11)</td>
<td rowspan="1" colspan="1">0.0726 (11)</td>
<td rowspan="1" colspan="1">−0.0275 (8)</td>
<td rowspan="1" colspan="1">0.0065 (8)</td>
<td rowspan="1" colspan="1">−0.0237 (9)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e1754"><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—O1W</td>
<td rowspan="1" colspan="1">2.0741 (10)</td>
<td rowspan="1" colspan="1">N3—C11</td>
<td rowspan="1" colspan="1">1.3428 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N1</td>
<td rowspan="1" colspan="1">2.2235 (10)</td>
<td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.3840 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N2</td>
<td rowspan="1" colspan="1">2.1898 (13)</td>
<td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.3934 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">2.2306 (14)</td>
<td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.3896 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O1W<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">2.0741 (10)</td>
<td rowspan="1" colspan="1">C3—C3<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">1.4860 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">2.2235 (10)</td>
<td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.3874 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—H13</td>
<td rowspan="1" colspan="1">0.884 (12)</td>
<td rowspan="1" colspan="1">C6—C7</td>
<td rowspan="1" colspan="1">1.3854 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—H12</td>
<td rowspan="1" colspan="1">0.877 (12)</td>
<td rowspan="1" colspan="1">C7—C8</td>
<td rowspan="1" colspan="1">1.3904 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—N4</td>
<td rowspan="1" colspan="1">1.247 (2)</td>
<td rowspan="1" colspan="1">C8—C9</td>
<td rowspan="1" colspan="1">1.486 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—N4</td>
<td rowspan="1" colspan="1">1.241 (2)</td>
<td rowspan="1" colspan="1">C9—C10<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">1.3922 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—N4</td>
<td rowspan="1" colspan="1">1.229 (2)</td>
<td rowspan="1" colspan="1">C9—C10</td>
<td rowspan="1" colspan="1">1.3922 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W—H14</td>
<td rowspan="1" colspan="1">0.878 (13)</td>
<td rowspan="1" colspan="1">C10—C11</td>
<td rowspan="1" colspan="1">1.3893 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W—H15</td>
<td rowspan="1" colspan="1">0.882 (14)</td>
<td rowspan="1" colspan="1">C1—H1</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">O3W—H17</td>
<td rowspan="1" colspan="1">0.887 (11)</td>
<td rowspan="1" colspan="1">C2—H2</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">O3W—H16</td>
<td rowspan="1" colspan="1">0.873 (13)</td>
<td rowspan="1" colspan="1">C4—H4</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C1</td>
<td rowspan="1" colspan="1">1.3402 (16)</td>
<td rowspan="1" colspan="1">C5—H5</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C5</td>
<td rowspan="1" colspan="1">1.3390 (16)</td>
<td rowspan="1" colspan="1">C6—H6</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">1.3432 (14)</td>
<td rowspan="1" colspan="1">C7—H7</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C6</td>
<td rowspan="1" colspan="1">1.3432 (14)</td>
<td rowspan="1" colspan="1">C10—H10</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N3—C11<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">1.3428 (15)</td>
<td rowspan="1" colspan="1">C11—H11</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">O1W—Co1—N1</td>
<td rowspan="1" colspan="1">91.74 (4)</td>
<td rowspan="1" colspan="1">C1—C2—C3</td>
<td rowspan="1" colspan="1">120.21 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—N2</td>
<td rowspan="1" colspan="1">90.15 (3)</td>
<td rowspan="1" colspan="1">C2—C3—C4</td>
<td rowspan="1" colspan="1">115.96 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—N3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">89.85 (3)</td>
<td rowspan="1" colspan="1">C2—C3—C3<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">121.97 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—O1W<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">179.71 (4)</td>
<td rowspan="1" colspan="1">C3<sup>iii</sup>
—C3—C4</td>
<td rowspan="1" colspan="1">122.07 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—N1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">88.27 (4)</td>
<td rowspan="1" colspan="1">C3—C4—C5</td>
<td rowspan="1" colspan="1">120.29 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—Co1—N2</td>
<td rowspan="1" colspan="1">88.64 (2)</td>
<td rowspan="1" colspan="1">N1—C5—C4</td>
<td rowspan="1" colspan="1">123.59 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—Co1—N3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">91.37 (2)</td>
<td rowspan="1" colspan="1">N2—C6—C7</td>
<td rowspan="1" colspan="1">123.39 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N1</td>
<td rowspan="1" colspan="1">88.27 (4)</td>
<td rowspan="1" colspan="1">C6—C7—C8</td>
<td rowspan="1" colspan="1">119.57 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—Co1—N1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">177.27 (4)</td>
<td rowspan="1" colspan="1">C7—C8—C9</td>
<td rowspan="1" colspan="1">121.36 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—Co1—N3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">180.00</td>
<td rowspan="1" colspan="1">C7<sup>ii</sup>
—C8—C9</td>
<td rowspan="1" colspan="1">121.36 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N2</td>
<td rowspan="1" colspan="1">90.15 (3)</td>
<td rowspan="1" colspan="1">C7—C8—C7<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">117.28 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1<sup>ii</sup>
—Co1—N2</td>
<td rowspan="1" colspan="1">88.64 (2)</td>
<td rowspan="1" colspan="1">C8—C9—C10<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">121.59 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">89.85 (3)</td>
<td rowspan="1" colspan="1">C8—C9—C10</td>
<td rowspan="1" colspan="1">121.59 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1<sup>ii</sup>
—Co1—N3<sup>i</sup>
</td>
<td rowspan="1" colspan="1">91.37 (2)</td>
<td rowspan="1" colspan="1">C10—C9—C10<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">116.82 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">91.74 (4)</td>
<td rowspan="1" colspan="1">C9—C10—C11</td>
<td rowspan="1" colspan="1">119.69 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">H12—O1W—H13</td>
<td rowspan="1" colspan="1">105.5 (12)</td>
<td rowspan="1" colspan="1">N3—C11—C10</td>
<td rowspan="1" colspan="1">123.72 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O1W—H12</td>
<td rowspan="1" colspan="1">124.5 (9)</td>
<td rowspan="1" colspan="1">N1—C1—H1</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O1W—H13</td>
<td rowspan="1" colspan="1">121.8 (9)</td>
<td rowspan="1" colspan="1">C2—C1—H1</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">H14—O2W—H15</td>
<td rowspan="1" colspan="1">104.3 (13)</td>
<td rowspan="1" colspan="1">C1—C2—H2</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">H16—O3W—H17</td>
<td rowspan="1" colspan="1">105.5 (12)</td>
<td rowspan="1" colspan="1">C3—C2—H2</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N1—C5</td>
<td rowspan="1" colspan="1">121.61 (8)</td>
<td rowspan="1" colspan="1">C5—C4—H4</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N1—C1</td>
<td rowspan="1" colspan="1">122.19 (7)</td>
<td rowspan="1" colspan="1">C3—C4—H4</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—N1—C5</td>
<td rowspan="1" colspan="1">116.20 (10)</td>
<td rowspan="1" colspan="1">C4—C5—H5</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N2—C6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">121.60 (7)</td>
<td rowspan="1" colspan="1">N1—C5—H5</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—N2—C6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">116.81 (12)</td>
<td rowspan="1" colspan="1">N2—C6—H6</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N2—C6</td>
<td rowspan="1" colspan="1">121.60 (7)</td>
<td rowspan="1" colspan="1">C7—C6—H6</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—N3—C11<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">116.27 (12)</td>
<td rowspan="1" colspan="1">C6—C7—H7</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1<sup>iv</sup>
—N3—C11<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">121.86 (7)</td>
<td rowspan="1" colspan="1">C8—C7—H7</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1<sup>iv</sup>
—N3—C11</td>
<td rowspan="1" colspan="1">121.86 (7)</td>
<td rowspan="1" colspan="1">C11—C10—H10</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—N4—O2</td>
<td rowspan="1" colspan="1">118.72 (17)</td>
<td rowspan="1" colspan="1">C9—C10—H10</td>
<td rowspan="1" colspan="1">120.00</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—N4—O3</td>
<td rowspan="1" colspan="1">120.61 (15)</td>
<td rowspan="1" colspan="1">C10—C11—H11</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—N4—O3</td>
<td rowspan="1" colspan="1">120.67 (17)</td>
<td rowspan="1" colspan="1">N3—C11—H11</td>
<td rowspan="1" colspan="1">118.00</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C1—C2</td>
<td rowspan="1" colspan="1">123.72 (11)</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">O1W—Co1—N1—C1</td>
<td rowspan="1" colspan="1">156.61 (10)</td>
<td rowspan="1" colspan="1">C11<sup>ii</sup>
—N3—C11—C10</td>
<td rowspan="1" colspan="1">1.48 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—Co1—N1—C1</td>
<td rowspan="1" colspan="1">−113.29 (9)</td>
<td rowspan="1" colspan="1">N1—C1—C2—C3</td>
<td rowspan="1" colspan="1">0.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3<sup>i</sup>
—Co1—N1—C1</td>
<td rowspan="1" colspan="1">66.72 (9)</td>
<td rowspan="1" colspan="1">C1—C2—C3—C4</td>
<td rowspan="1" colspan="1">−1.58 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N1—C1</td>
<td rowspan="1" colspan="1">−23.10 (10)</td>
<td rowspan="1" colspan="1">C1—C2—C3—C3<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">178.01 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—N1—C5</td>
<td rowspan="1" colspan="1">−23.77 (10)</td>
<td rowspan="1" colspan="1">C4—C3—C3<sup>iii</sup>
—C2<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">−0.44 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—Co1—N1—C5</td>
<td rowspan="1" colspan="1">66.34 (9)</td>
<td rowspan="1" colspan="1">C2—C3—C4—C5</td>
<td rowspan="1" colspan="1">1.63 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3<sup>i</sup>
—Co1—N1—C5</td>
<td rowspan="1" colspan="1">−113.66 (9)</td>
<td rowspan="1" colspan="1">C3<sup>iii</sup>
—C3—C4—C5</td>
<td rowspan="1" colspan="1">−177.96 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N1—C5</td>
<td rowspan="1" colspan="1">156.53 (10)</td>
<td rowspan="1" colspan="1">C2—C3—C3<sup>iii</sup>
—C2<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">−179.98 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—N2—C6</td>
<td rowspan="1" colspan="1">−53.00 (7)</td>
<td rowspan="1" colspan="1">C2—C3—C3<sup>iii</sup>
—C4<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">0.44 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—Co1—N2—C6</td>
<td rowspan="1" colspan="1">−144.74 (7)</td>
<td rowspan="1" colspan="1">C4—C3—C3<sup>iii</sup>
—C4<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">−179.98 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>ii</sup>
—Co1—N2—C6</td>
<td rowspan="1" colspan="1">127.00 (7)</td>
<td rowspan="1" colspan="1">C3—C4—C5—N1</td>
<td rowspan="1" colspan="1">−0.4 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1<sup>ii</sup>
—Co1—N2—C6</td>
<td rowspan="1" colspan="1">35.27 (7)</td>
<td rowspan="1" colspan="1">N2—C6—C7—C8</td>
<td rowspan="1" colspan="1">−0.39 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—N2—C6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">127.00 (7)</td>
<td rowspan="1" colspan="1">C6—C7—C8—C9</td>
<td rowspan="1" colspan="1">−179.82 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—Co1—N2—C6<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">35.27 (7)</td>
<td rowspan="1" colspan="1">C6—C7—C8—C7<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.18 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N1—C1—C2</td>
<td rowspan="1" colspan="1">−179.36 (10)</td>
<td rowspan="1" colspan="1">C7—C8—C9—C10<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">−44.87 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—N1—C1—C2</td>
<td rowspan="1" colspan="1">1.00 (19)</td>
<td rowspan="1" colspan="1">C7<sup>ii</sup>
—C8—C9—C10</td>
<td rowspan="1" colspan="1">−44.87 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N1—C5—C4</td>
<td rowspan="1" colspan="1">179.41 (11)</td>
<td rowspan="1" colspan="1">C7—C8—C9—C10</td>
<td rowspan="1" colspan="1">135.13 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—N1—C5—C4</td>
<td rowspan="1" colspan="1">−0.95 (19)</td>
<td rowspan="1" colspan="1">C8—C9—C10—C11</td>
<td rowspan="1" colspan="1">−178.64 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—N2—C6—C7</td>
<td rowspan="1" colspan="1">−179.80 (9)</td>
<td rowspan="1" colspan="1">C10<sup>ii</sup>
—C9—C10—C11</td>
<td rowspan="1" colspan="1">1.36 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6<sup>ii</sup>
—N2—C6—C7</td>
<td rowspan="1" colspan="1">0.20 (15)</td>
<td rowspan="1" colspan="1">C9—C10—C11—N3</td>
<td rowspan="1" colspan="1">−2.9 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1<sup>iv</sup>
—N3—C11—C10</td>
<td rowspan="1" colspan="1">−178.53 (10)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) <italic>x</italic>
, <italic>y</italic>
−1, <italic>z</italic>
; (ii) −<italic>x</italic>
+1, <italic>y</italic>
, −<italic>z</italic>
+3/2; (iii) −<italic>x</italic>
+3/2, −<italic>y</italic>
+3/2, −<italic>z</italic>
+1; (iv) <italic>x</italic>
, <italic>y</italic>
+1, <italic>z</italic>
.</p>
</sec>
<sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e2690"><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">O1<italic>W</italic>
—H12···O3<italic>W</italic>
<sup>v</sup>
</td>
<td rowspan="1" colspan="1">0.877 (12)</td>
<td rowspan="1" colspan="1">1.801 (12)</td>
<td rowspan="1" colspan="1">2.675 (2)</td>
<td rowspan="1" colspan="1">174.2 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1<italic>W</italic>
—H13···O2<italic>W</italic>
<sup>vi</sup>
</td>
<td rowspan="1" colspan="1">0.884 (12)</td>
<td rowspan="1" colspan="1">1.790 (12)</td>
<td rowspan="1" colspan="1">2.6744 (18)</td>
<td rowspan="1" colspan="1">178.7 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2<italic>W</italic>
—H14···O1</td>
<td rowspan="1" colspan="1">0.878 (13)</td>
<td rowspan="1" colspan="1">1.959 (12)</td>
<td rowspan="1" colspan="1">2.827 (2)</td>
<td rowspan="1" colspan="1">170.1 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2<italic>W</italic>
—H15···O2<sup>vii</sup>
</td>
<td rowspan="1" colspan="1">0.882 (14)</td>
<td rowspan="1" colspan="1">1.906 (14)</td>
<td rowspan="1" colspan="1">2.765 (2)</td>
<td rowspan="1" colspan="1">164.2 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3<italic>W</italic>
—H16···O1</td>
<td rowspan="1" colspan="1">0.873 (13)</td>
<td rowspan="1" colspan="1">1.908 (13)</td>
<td rowspan="1" colspan="1">2.769 (3)</td>
<td rowspan="1" colspan="1">168.9 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3<italic>W</italic>
—H17···O3<sup>vii</sup>
</td>
<td rowspan="1" colspan="1">0.887 (11)</td>
<td rowspan="1" colspan="1">2.109 (11)</td>
<td rowspan="1" colspan="1">2.958 (2)</td>
<td rowspan="1" colspan="1">159.9 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—H1···O1<italic>W</italic>
<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.93</td>
<td rowspan="1" colspan="1">2.54</td>
<td rowspan="1" colspan="1">3.0860 (15)</td>
<td rowspan="1" colspan="1">117</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11···N1<sup>iv</sup>
</td>
<td rowspan="1" colspan="1">0.93</td>
<td rowspan="1" colspan="1">2.58</td>
<td rowspan="1" colspan="1">3.1974 (15)</td>
<td rowspan="1" colspan="1">124</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—H11···O3<sup>viii</sup>
</td>
<td rowspan="1" colspan="1">0.93</td>
<td rowspan="1" colspan="1">2.46</td>
<td rowspan="1" colspan="1">3.209 (2)</td>
<td rowspan="1" colspan="1">137</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (ii) −<italic>x</italic>
+1, <italic>y</italic>
, −<italic>z</italic>
+3/2; (iv) <italic>x</italic>
, <italic>y</italic>
+1, <italic>z</italic>
; (v) −<italic>x</italic>
+3/2, <italic>y</italic>
−1/2, −<italic>z</italic>
+3/2; (vi) <italic>x</italic>
, −<italic>y</italic>
+2, <italic>z</italic>
+1/2; (vii) <italic>x</italic>
, −<italic>y</italic>
+2, <italic>z</italic>
−1/2; (viii) −<italic>x</italic>
+3/2, <italic>y</italic>
+1/2, −<italic>z</italic>
+3/2.</p>
</sec>
</app>
</app-group>
<ref-list><title>References</title>
<ref id="bb1"><mixed-citation publication-type="other">Aoyagi, M., Biradha, K. & Fujita, M. (2000). <italic>Bull. Chem. Soc. Jpn</italic>
, <bold>73</bold>
, 1369–1373.</mixed-citation>
</ref>
<ref id="bb2"><mixed-citation publication-type="other">Bruker (2006). <italic>APEX2</italic>
and <italic>SAINT</italic>
Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation>
</ref>
<ref id="bb3"><mixed-citation publication-type="other">Dowty, E. (1995). <italic>ATOMS</italic>
Shape Software, Kingsport, Tennessee, USA.</mixed-citation>
</ref>
<ref id="bb4"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic>
<bold>45</bold>
, 849–854.</mixed-citation>
</ref>
<ref id="bb5"><mixed-citation publication-type="other">Felloni, M., Blake, A. J., Champness, N. R., Hubbertey, P., Wilson, C. & Schröder, M. (2002). <italic>J. Supramol. Chem.</italic>
<bold>2</bold>
, 163–174.</mixed-citation>
</ref>
<ref id="bb6"><mixed-citation publication-type="other">Jin, J., Niu, S. Y., Yang, G. D. & Ye, L. (2006). <italic>Z. Anorg. Allg. Chem.</italic>
<bold>632</bold>
, 2350–2354.</mixed-citation>
</ref>
<ref id="bb7"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic>
A<bold>64</bold>
, 112–122.</mixed-citation>
</ref>
<ref id="bb8"><mixed-citation publication-type="other">Tong, M.-L., Zheng, S.-L. & Chen, X.-M. (2000). <italic>Polyhedron</italic>
, <bold>19</bold>
, 1809–1814.</mixed-citation>
</ref>
</ref-list>
</back>
<floats-group><table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Selected bond lengths (Å)</title>
</caption>
<table frame="hsides" rules="groups"><tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Co1—O1<italic>W</italic>
</td>
<td style="" rowspan="1" colspan="1" align="char" valign="top">2.0741 (10)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Co1—N1</td>
<td style="" rowspan="1" colspan="1" align="char" valign="top">2.2235 (10)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Co1—N2</td>
<td style="" rowspan="1" colspan="1" align="char" valign="top">2.1898 (13)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Co1—N3<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="char" valign="top">2.2306 (14)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table2" position="float"><label>Table 2</label>
<caption><title>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">O1<italic>W</italic>
—H12⋯O3<italic>W</italic>
<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.877 (12)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.801 (12)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.675 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">174.2 (14)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1<italic>W</italic>
—H13⋯O2<italic>W</italic>
<sup>iii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.884 (12)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.790 (12)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.6744 (18)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">178.7 (16)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O2<italic>W</italic>
—H14⋯O1</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.878 (13)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.959 (12)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.827 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">170.1 (13)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O2<italic>W</italic>
—H15⋯O2<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.882 (14)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.906 (14)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.765 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">164.2 (14)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O3<italic>W</italic>
—H16⋯O1</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.873 (13)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.908 (13)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.769 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">168.9 (14)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O3<italic>W</italic>
—H17⋯O3<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.887 (11)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.109 (11)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.958 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">159.9 (15)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C1—H1⋯O1<italic>W</italic>
<sup>v</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">2.54</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.0860 (15)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">117</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C11—H11⋯N1<sup>vi</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">3.1974 (15)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">124</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C11—H11⋯O3<sup>vii</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">2.46</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.209 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">137</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (ii) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi8.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iii) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi9.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iv) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi10.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (v) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi11.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (vi) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi12.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (vii) <inline-formula><inline-graphic xlink:href="e-69-0m177-efi13.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>
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