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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structure of <italic>cis</italic>
-tetraaquadichloridocobalt(II) sulfolane disolvate</title>
<author><name sortKey="Boudraa, Mhamed" sort="Boudraa, Mhamed" uniqKey="Boudraa M" first="Mhamed" last="Boudraa">Mhamed Boudraa</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Bouacida, Sofiane" sort="Bouacida, Sofiane" uniqKey="Bouacida S" first="Sofiane" last="Bouacida">Sofiane Bouacida</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<country>Algeria</country>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="b">Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Bouchareb, Hasna" sort="Bouchareb, Hasna" uniqKey="Bouchareb H" first="Hasna" last="Bouchareb">Hasna Bouchareb</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<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, Université Constantine 1, 25000 ,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Chtoun, El Hossain" sort="Chtoun, El Hossain" uniqKey="Chtoun E" first="El Hossain" last="Chtoun">El Hossain Chtoun</name>
<affiliation><nlm:aff id="c">Université Abdelmalek Essaadi, Faculté des Sciences, BP 2121 M’Hannech II, 93002 Tétouan,<country>Morocco</country>
</nlm:aff>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">25878832</idno>
<idno type="pmc">4384590</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4384590</idno>
<idno type="RBID">PMC:4384590</idno>
<idno type="doi">10.1107/S2056989014027753</idno>
<date when="2015">2015</date>
<idno type="wicri:Area/Pmc/Corpus">000048</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000048</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structure of <italic>cis</italic>
-tetraaquadichloridocobalt(II) sulfolane disolvate</title>
<author><name sortKey="Boudraa, Mhamed" sort="Boudraa, Mhamed" uniqKey="Boudraa M" first="Mhamed" last="Boudraa">Mhamed Boudraa</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Bouacida, Sofiane" sort="Bouacida, Sofiane" uniqKey="Bouacida S" first="Sofiane" last="Bouacida">Sofiane Bouacida</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<country>Algeria</country>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="b">Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Bouchareb, Hasna" sort="Bouchareb, Hasna" uniqKey="Bouchareb H" first="Hasna" last="Bouchareb">Hasna Bouchareb</name>
<affiliation><nlm:aff id="a">Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<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, Université Constantine 1, 25000 ,<country>Algeria</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Chtoun, El Hossain" sort="Chtoun, El Hossain" uniqKey="Chtoun E" first="El Hossain" last="Chtoun">El Hossain Chtoun</name>
<affiliation><nlm:aff id="c">Université Abdelmalek Essaadi, Faculté des Sciences, BP 2121 M’Hannech II, 93002 Tétouan,<country>Morocco</country>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title>
<idno type="eISSN">2056-9890</idno>
<imprint><date when="2015">2015</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p>In the title compound, [CoCl<sub>2</sub>
(H<sub>2</sub>
O)<sub>4</sub>
]·2C<sub>4</sub>
H<sub>8</sub>
SO<sub>2</sub>
, the Co<sup>II</sup>
cation is located on the twofold rotation axis and is coordinated by four water molecules and two adjacent chloride ligands in a slightly distorted octahedral coordination environment. The <italic>cisoid</italic>
angles are in the range 83.27 (5)–99.66 (2)°. The three <italic>transoid</italic>
angles deviate significantly from the ideal linear angle. The crystal packing can be described as a linear arrangement of complex units along <italic>c</italic>
formed by bifurcated O—H⋯Cl hydrogen bonds between two water molecules from one complex unit towards one chloride ligand of the neighbouring complex. Two solvent molecules per complex are attached to this infinite chain <italic>via</italic>
O—H⋯O hydrogen bonds in which water molecules act as the hydrogen-bond donor and sulfolane O atoms as the hydrogen-bond acceptor sites.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
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</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr E Crystallogr Commun</journal-id>
<journal-id journal-id-type="iso-abbrev">Acta Crystallogr E Crystallogr Commun</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Crystallographic Communications</journal-title>
</journal-title-group>
<issn pub-type="epub">2056-9890</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">25878832</article-id>
<article-id pub-id-type="pmc">4384590</article-id>
<article-id pub-id-type="publisher-id">im2458</article-id>
<article-id pub-id-type="doi">10.1107/S2056989014027753</article-id>
<article-id pub-id-type="coden">ACSECI</article-id>
<article-id pub-id-type="pii">S2056989014027753</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Data Reports</subject>
</subj-group>
</article-categories>
<title-group><article-title>Crystal structure of <italic>cis</italic>
-tetraaquadichloridocobalt(II) sulfolane disolvate</article-title>
<alt-title><italic>[CoCl<sub>2</sub>
(H<sub>2</sub>
O)<sub>4</sub>
]·2C<sub>4</sub>
H<sub>8</sub>
O<sub>2</sub>
S</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Boudraa</surname>
<given-names>Mhamed</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Bouacida</surname>
<given-names>Sofiane</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
<xref ref-type="aff" rid="b">b</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Bouchareb</surname>
<given-names>Hasna</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>
<contrib contrib-type="author"><name><surname>Chtoun</surname>
<given-names>El Hossain</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<aff id="a"><label>a</label>
Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 ,<country>Algeria</country>
</aff>
<aff id="b"><label>b</label>
Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi,<country>Algeria</country>
</aff>
<aff id="c"><label>c</label>
Université Abdelmalek Essaadi, Faculté des Sciences, BP 2121 M’Hannech II, 93002 Tétouan,<country>Morocco</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>bouacida_sofiane@yahoo.fr</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>2</month>
<year>2015</year>
</pub-date>
<pub-date pub-type="epub"><day>03</day>
<month>1</month>
<year>2015</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>03</day>
<month>1</month>
<year>2015</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
. </pmc-comment>
<volume>71</volume>
<issue>Pt 2</issue>
<issue-id pub-id-type="publisher-id">e150200</issue-id>
<fpage>m16</fpage>
<lpage>m17</lpage>
<history><date date-type="received"><day>07</day>
<month>12</month>
<year>2014</year>
</date>
<date date-type="accepted"><day>19</day>
<month>12</month>
<year>2014</year>
</date>
</history>
<permissions><copyright-statement>© Boudraa et al. 2015</copyright-statement>
<copyright-year>2015</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/S2056989014027753">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>In the title compound, [CoCl<sub>2</sub>
(H<sub>2</sub>
O)<sub>4</sub>
]·2C<sub>4</sub>
H<sub>8</sub>
SO<sub>2</sub>
, the Co<sup>II</sup>
cation is located on the twofold rotation axis and is coordinated by four water molecules and two adjacent chloride ligands in a slightly distorted octahedral coordination environment. The <italic>cisoid</italic>
angles are in the range 83.27 (5)–99.66 (2)°. The three <italic>transoid</italic>
angles deviate significantly from the ideal linear angle. The crystal packing can be described as a linear arrangement of complex units along <italic>c</italic>
formed by bifurcated O—H⋯Cl hydrogen bonds between two water molecules from one complex unit towards one chloride ligand of the neighbouring complex. Two solvent molecules per complex are attached to this infinite chain <italic>via</italic>
O—H⋯O hydrogen bonds in which water molecules act as the hydrogen-bond donor and sulfolane O atoms as the hydrogen-bond acceptor sites.</p>
</abstract>
<kwd-group><kwd>crystal structure</kwd>
<kwd>cobalt(II) complex</kwd>
<kwd>sulfolane solvate</kwd>
</kwd-group>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature </title>
<p>For structures where the Co<sup>II</sup>
atom exhibits an octahedral geometry and is coordinated by water molecules, see: Waizumi <italic>et al.</italic>
(1990<xref ref-type="bibr" rid="bb12"> ▸</xref>
); Sarangarajan <italic>et al.</italic>
(2008<xref ref-type="bibr" rid="bb9"> ▸</xref>
). For potential applications of organic–inorganic hybrid compounds, see: Al-Ktaifani & Rukiah (2011<xref ref-type="bibr" rid="bb1"> ▸</xref>
). For related structures, see: Bouacida <italic>et al.</italic>
(2005<xref ref-type="bibr" rid="bb3"> ▸</xref>
, 2013<xref ref-type="bibr" rid="bb2"> ▸</xref>
); Sahbani <italic>et al.</italic>
(2014<xref ref-type="bibr" rid="bb8"> ▸</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-71-00m16-scheme1.jpg" position="float"></graphic>
</chem-struct>
</p>
</sec>
<sec id="sec2"><title>Experimental </title>
<sec id="sec2.1"><title>Crystal data </title>
<p><list list-type="simple" id="l1"><list-item><p>[CoCl<sub>2</sub>
(H<sub>2</sub>
O)<sub>4</sub>
]·2C<sub>4</sub>
H<sub>8</sub>
O<sub>2</sub>
S</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 442.22</p>
</list-item>
<list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-71-00m16-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
= 20.062 (2) Å</p>
</list-item>
<list-item><p><italic>b</italic>
= 9.4284 (10) Å</p>
</list-item>
<list-item><p><italic>c</italic>
= 10.5882 (13) Å</p>
</list-item>
<list-item><p>β = 118.734 (5)°</p>
</list-item>
<list-item><p><italic>V</italic>
= 1756.2 (3) 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 = 1.55 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
= 295 K</p>
</list-item>
<list-item><p>0.21 × 0.15 × 0.09 mm</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.2"><title>Data collection </title>
<p><list list-type="simple" id="l2"><list-item><p>Bruker APEXII diffractometer</p>
</list-item>
<list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>
; Sheldrick, 2002<xref ref-type="bibr" rid="bb10"> ▸</xref>
) <italic>T</italic>
<sub>min</sub>
= 0.649, <italic>T</italic>
<sub>max</sub>
= 0.748</p>
</list-item>
<list-item><p>20238 measured reflections</p>
</list-item>
<list-item><p>5090 independent reflections</p>
</list-item>
<list-item><p>3409 reflections with <italic>I</italic>
> 2σ(<italic>I</italic>
)</p>
</list-item>
<list-item><p><italic>R</italic>
<sub>int</sub>
= 0.061</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.3"><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>
)] = 0.043</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.129</p>
</list-item>
<list-item><p><italic>S</italic>
= 1.01</p>
</list-item>
<list-item><p>5090 reflections</p>
</list-item>
<list-item><p>108 parameters</p>
</list-item>
<list-item><p>4 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>
= 0.90 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
= −1.44 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
<sec id="d5e540"><title></title>
<p>Data collection: <italic>APEX2</italic>
(Bruker, 2011<xref ref-type="bibr" rid="bb5"> ▸</xref>
); cell refinement: <italic>SAINT</italic>
(Bruker, 2011<xref ref-type="bibr" rid="bb5"> ▸</xref>
); data reduction: <italic>SAINT</italic>
; program(s) used to solve structure: <italic>SIR2002</italic>
(Burla <italic>et al.</italic>
, 2005<xref ref-type="bibr" rid="bb6"> ▸</xref>
); program(s) used to refine structure: <italic>SHELXL97</italic>
(Sheldrick, 2008<xref ref-type="bibr" rid="bb11"> ▸</xref>
); molecular graphics: <italic>ORTEP-3 for Windows</italic>
(Farrugia, 2012<xref ref-type="bibr" rid="bb7"> ▸</xref>
) and <italic>DIAMOND</italic>
(Brandenburg & Berndt, 2001<xref ref-type="bibr" rid="bb4"> ▸</xref>
); software used to prepare material for publication: <italic>WinGX</italic>
(Farrugia, 2012<xref ref-type="bibr" rid="bb7"> ▸</xref>
).</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S2056989014027753/im2458sup1.cif">10.1107/S2056989014027753/im2458sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-71-00m16-sup1.cif" xlink:type="simple" id="d36e159" 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/S2056989014027753/im2458Isup2.hkl">10.1107/S2056989014027753/im2458Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-71-00m16-Isup2.hkl" xlink:type="simple" id="d36e166" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-71-00m16-fig1.tif"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S2056989014027753/im2458fig1.tif">10.1107/S2056989014027753/im2458fig1.tif</ext-link>
</p>
<p>Molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. Only the asymmetric unit is labelled. H atoms are represented as small spheres of arbitrary radii.</p>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-71-00m16-fig2.tif"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>c . DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S2056989014027753/im2458fig2.tif">10.1107/S2056989014027753/im2458fig2.tif</ext-link>
</p>
<p>Packing diagram of (I) showing the infinite chains of complex units and solvent molecule along the <italic>c</italic>
axis.</p>
</supplementary-material>
<supplementary-material content-type="local-data"><p>CCDC reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1040554">1040554</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?im2458&file=im2458sup0.html&mime=text/html"> crystallographic information</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?im2458sup1&Qmime=cif">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?im2458&checkcif=yes">checkCIF report</ext-link>
</p>
</supplementary-material>
</sec>
</body>
<back><fn-group><fn id="fnu1"><p>Supporting information for this paper is available from the IUCr electronic archives (Reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsup?im2458">IM2458</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>Thanks are due to MESRS and ATRST (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique et l’Agence Thématique de Recherche en Sciences et Technologie - Algérie) for financial support <italic>via</italic>
the PNR programme.</p>
</ack>
<app-group><app><title>supplementary crystallographic
information</title>
<sec id="comment"><title>S1. Comment </title>
<p>Organic-inorganic hybrid salts have received considerable attention because of
their potential applications in analytical, material and supramolecular
chemistry (Al-Ktaifani <italic>et al.</italic>
, 2011; Bouacida <italic>et al.</italic>
2005, 2013;
Sahbani <italic>et al.</italic>
, 2014). In this work, we report the preparation
and the
structural investigation of [Co(H<sub>2</sub>
O)<sub>4</sub>
Cl<sub>2</sub>
] × 2 C<sub>4</sub>
H<sub>8</sub>
SO<sub>2</sub>
. Since
the central cobalt the Co<sup>II</sup>
cation is located on the twofold rotation axis
the asymmetric unit of (I) consists of one one half of the complex unit and
one molecule of sulfolane (Figure 1).</p>
<p>The structure of the compound consists of discrete tetraaquadichlorocobalt(II)
complexes stacked in chains parallel to the <italic>c</italic>
axis. The Co<sup>II</sup>
cation
is coordinated by four water molecules and two adjacent chloride ligands in a
slightly distorted octahedral geometry. The two Co—Cl distances are 2.510 (6) Å and the Co—O distances are between 2.165 (3) and 2.243 (3) Å in good
agreement with that found in mineral compound CoCl<sub>2</sub>
O<sub>4</sub>
H<sub>8</sub>
(Waizumi <italic>et
al.</italic>
, 1990) and in the coordination compound
[CoCl<sub>2</sub>
(H<sub>2</sub>
O)<sub>4</sub>
]C<sub>4</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
(Sarangarajan <italic>et al.</italic>
, 2008).
Cisoid
angles around Co atom are in the range of 83.27 (5)° to 99.66 (2)°. In the
organic molecule, the S atom is tetrahedrally coordinated by two O and two C
atoms. The three bonds C—C are in the range 1.516 (2)–1,531 (3) Å. In the
crystal, molecules are linked by O—H···O and O—H···Cl hydrogen bonds
forming chains along [001] (Figure 2). The crystal packing can be described as
a linear arrangement of complex units along <italic>c</italic>
formed by bifurcated
O–H···Cl hydrogen bonds between two water molecules from one complex unit
towards one chloride ligand of the neighboring complex. Two solvent molecules
per complex are attached to this infinite chain via O–H···O hydrogen bonds in
which water molecules act as the hydrogen bond donor and sulfolane oxygen
atoms as the hydrogen bond acceptor sites.</p>
</sec>
<sec id="experimental"><title>S2. Experimental </title>
<p>A solution of CoCl<sub>2</sub>
× 2 H<sub>2</sub>
O (34 mg, 0.2 mmol) in water (10 ml) was
added dropwise to a solution of sulfolane (24 mg, 0.2 mmol) in water (10 ml).
The mixture was then refluxed with stirring for 3 h and the resulting solution
was left to stand at room temperature. After several days, blue crystals were
obtained and dried under vacuum (yield: 55%).</p>
</sec>
<sec id="refinement"><title>S3. Refinement </title>
<p>All non-H atoms were refined with anisotropic displacement parameters.
Approximate positions for all H atoms were first obtained from the difference
electron density map. However, the H atoms were situated into idealized
positions and the H-atoms have been refined within the riding atom
approximation with C—H = 0.93 Å and <italic>U</italic>
<sub>iso</sub>
= 1.2<italic>U</italic>
<sub>eq</sub>
(C)
except for H atoms of water molecules, which were refined isotropically using
the following restraints: O—H = 0.84 (2) Å, H···H = 1.45 (2) Å and
<italic>U</italic>
<sub>iso</sub>
= 1.5<italic>U</italic>
<sub>eq</sub>
(O).</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>Molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. Only the asymmetric unit is labelled. H atoms are represented as small spheres of arbitrary radii.</p>
</caption>
<graphic xlink:href="e-71-00m16-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>Packing diagram of (I) showing the infinite chains of complex units and solvent molecule along the c axis.</p>
</caption>
<graphic xlink:href="e-71-00m16-fig2"></graphic>
</fig>
</sec>
<sec id="tablewrapcrystaldatalong"><title>Crystal data</title>
<table-wrap position="anchor" id="d1e215"><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">[CoCl<sub>2</sub>
(H<sub>2</sub>
O)<sub>4</sub>
]·2C<sub>4</sub>
H<sub>8</sub>
O<sub>2</sub>
S</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 916</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 442.22</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
= 1.673 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>C</italic>
2/<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1">Hall symbol: -C 2yc</td>
<td rowspan="1" colspan="1">Cell parameters from 5148 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
= 20.062 (2) Å</td>
<td rowspan="1" colspan="1">θ = 2.5–35.1°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
= 9.4284 (10) Å</td>
<td rowspan="1" colspan="1">µ = 1.55 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
= 10.5882 (13) Å</td>
<td rowspan="1" colspan="1"><italic>T</italic>
= 295 K</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 118.734 (5)°</td>
<td rowspan="1" colspan="1">Prism, blue</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
= 1756.2 (3) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.21 × 0.15 × 0.09 mm</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
= 4</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapdatacollectionlong"><title>Data collection</title>
<table-wrap position="anchor" id="d1e350"><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 diffractometer</td>
<td rowspan="1" colspan="1">5090 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: sealed tube</td>
<td rowspan="1" colspan="1">3409 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>
= 0.061</td>
</tr>
<tr><td rowspan="1" colspan="1">φ and ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
= 39.0°, θ<sub>min</sub>
= 2.3°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>
; Sheldrick, 2002)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
= −34→35</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
= 0.649, <italic>T</italic>
<sub>max</sub>
= 0.748</td>
<td rowspan="1" colspan="1"><italic>k</italic>
= −16→16</td>
</tr>
<tr><td rowspan="1" colspan="1">20238 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
= −18→14</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraprefinementdatalong"><title>Refinement</title>
<table-wrap position="anchor" id="d1e467"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
> 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.043</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.129</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
= 1.01</td>
<td rowspan="1" colspan="1"><italic>w</italic>
= 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0666<italic>P</italic>
)<sup>2</sup>
] where <italic>P</italic>
= (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
+ 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1">5090 reflections</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
= 0.007</td>
</tr>
<tr><td rowspan="1" colspan="1">108 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
= 0.90 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">4 restraints</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
= −1.44 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e622"><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="d1e721"><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">0.5</td>
<td rowspan="1" colspan="1">0.47467 (3)</td>
<td rowspan="1" colspan="1">0.25</td>
<td rowspan="1" colspan="1">0.01473 (8)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.76287 (2)</td>
<td rowspan="1" colspan="1">0.53220 (4)</td>
<td rowspan="1" colspan="1">0.58938 (4)</td>
<td rowspan="1" colspan="1">0.01334 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">Cl1</td>
<td rowspan="1" colspan="1">0.43290 (2)</td>
<td rowspan="1" colspan="1">0.30294 (4)</td>
<td rowspan="1" colspan="1">0.04608 (4)</td>
<td rowspan="1" colspan="1">0.01647 (9)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1W</td>
<td rowspan="1" colspan="1">0.59916 (7)</td>
<td rowspan="1" colspan="1">0.49821 (15)</td>
<td rowspan="1" colspan="1">0.22088 (14)</td>
<td rowspan="1" colspan="1">0.0177 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1W</td>
<td rowspan="1" colspan="1">0.5953 (15)</td>
<td rowspan="1" colspan="1">0.556 (2)</td>
<td rowspan="1" colspan="1">0.168 (2)</td>
<td rowspan="1" colspan="1">0.027*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2W</td>
<td rowspan="1" colspan="1">0.6412 (11)</td>
<td rowspan="1" colspan="1">0.483 (3)</td>
<td rowspan="1" colspan="1">0.288 (2)</td>
<td rowspan="1" colspan="1">0.027*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2W</td>
<td rowspan="1" colspan="1">0.54617 (7)</td>
<td rowspan="1" colspan="1">0.65037 (13)</td>
<td rowspan="1" colspan="1">0.41295 (13)</td>
<td rowspan="1" colspan="1">0.0155 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3W</td>
<td rowspan="1" colspan="1">0.5200 (12)</td>
<td rowspan="1" colspan="1">0.669 (3)</td>
<td rowspan="1" colspan="1">0.452 (2)</td>
<td rowspan="1" colspan="1">0.023*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4W</td>
<td rowspan="1" colspan="1">0.5887 (12)</td>
<td rowspan="1" colspan="1">0.631 (3)</td>
<td rowspan="1" colspan="1">0.467 (3)</td>
<td rowspan="1" colspan="1">0.023*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.90875 (11)</td>
<td rowspan="1" colspan="1">0.5145 (2)</td>
<td rowspan="1" colspan="1">0.7520 (3)</td>
<td rowspan="1" colspan="1">0.0298 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3A</td>
<td rowspan="1" colspan="1">0.955</td>
<td rowspan="1" colspan="1">0.5538</td>
<td rowspan="1" colspan="1">0.8296</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3B</td>
<td rowspan="1" colspan="1">0.9206</td>
<td rowspan="1" colspan="1">0.4724</td>
<td rowspan="1" colspan="1">0.6815</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.84886 (10)</td>
<td rowspan="1" colspan="1">0.6288 (2)</td>
<td rowspan="1" colspan="1">0.6830 (2)</td>
<td rowspan="1" colspan="1">0.0240 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4A</td>
<td rowspan="1" colspan="1">0.8584</td>
<td rowspan="1" colspan="1">0.686</td>
<td rowspan="1" colspan="1">0.6172</td>
<td rowspan="1" colspan="1">0.029*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4B</td>
<td rowspan="1" colspan="1">0.8475</td>
<td rowspan="1" colspan="1">0.69</td>
<td rowspan="1" colspan="1">0.7554</td>
<td rowspan="1" colspan="1">0.029*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.79391 (13)</td>
<td rowspan="1" colspan="1">0.3742 (2)</td>
<td rowspan="1" colspan="1">0.6942 (2)</td>
<td rowspan="1" colspan="1">0.0293 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1A</td>
<td rowspan="1" colspan="1">0.7618</td>
<td rowspan="1" colspan="1">0.3529</td>
<td rowspan="1" colspan="1">0.737</td>
<td rowspan="1" colspan="1">0.035*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1B</td>
<td rowspan="1" colspan="1">0.7924</td>
<td rowspan="1" colspan="1">0.2945</td>
<td rowspan="1" colspan="1">0.635</td>
<td rowspan="1" colspan="1">0.035*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.87487 (14)</td>
<td rowspan="1" colspan="1">0.4035 (3)</td>
<td rowspan="1" colspan="1">0.8102 (3)</td>
<td rowspan="1" colspan="1">0.0386 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2A</td>
<td rowspan="1" colspan="1">0.9047</td>
<td rowspan="1" colspan="1">0.317</td>
<td rowspan="1" colspan="1">0.8342</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2B</td>
<td rowspan="1" colspan="1">0.8752</td>
<td rowspan="1" colspan="1">0.4386</td>
<td rowspan="1" colspan="1">0.8966</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O12</td>
<td rowspan="1" colspan="1">0.70254 (8)</td>
<td rowspan="1" colspan="1">0.60180 (16)</td>
<td rowspan="1" colspan="1">0.60336 (16)</td>
<td rowspan="1" colspan="1">0.0245 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O11</td>
<td rowspan="1" colspan="1">0.74827 (8)</td>
<td rowspan="1" colspan="1">0.50189 (17)</td>
<td rowspan="1" colspan="1">0.44424 (16)</td>
<td rowspan="1" colspan="1">0.0273 (3)</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="d1e1036"><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">0.01483 (14)</td>
<td rowspan="1" colspan="1">0.01815 (15)</td>
<td rowspan="1" colspan="1">0.01223 (15)</td>
<td rowspan="1" colspan="1">0</td>
<td rowspan="1" colspan="1">0.00731 (12)</td>
<td rowspan="1" colspan="1">0</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.01081 (15)</td>
<td rowspan="1" colspan="1">0.01611 (17)</td>
<td rowspan="1" colspan="1">0.01057 (17)</td>
<td rowspan="1" colspan="1">−0.00112 (12)</td>
<td rowspan="1" colspan="1">0.00313 (13)</td>
<td rowspan="1" colspan="1">0.00104 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">Cl1</td>
<td rowspan="1" colspan="1">0.02063 (18)</td>
<td rowspan="1" colspan="1">0.01729 (17)</td>
<td rowspan="1" colspan="1">0.01137 (16)</td>
<td rowspan="1" colspan="1">−0.00469 (13)</td>
<td rowspan="1" colspan="1">0.00760 (14)</td>
<td rowspan="1" colspan="1">−0.00251 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W</td>
<td rowspan="1" colspan="1">0.0121 (5)</td>
<td rowspan="1" colspan="1">0.0302 (7)</td>
<td rowspan="1" colspan="1">0.0117 (5)</td>
<td rowspan="1" colspan="1">0.0022 (4)</td>
<td rowspan="1" colspan="1">0.0064 (4)</td>
<td rowspan="1" colspan="1">0.0051 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W</td>
<td rowspan="1" colspan="1">0.0149 (5)</td>
<td rowspan="1" colspan="1">0.0186 (5)</td>
<td rowspan="1" colspan="1">0.0130 (5)</td>
<td rowspan="1" colspan="1">−0.0020 (4)</td>
<td rowspan="1" colspan="1">0.0067 (4)</td>
<td rowspan="1" colspan="1">−0.0022 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0136 (7)</td>
<td rowspan="1" colspan="1">0.0444 (12)</td>
<td rowspan="1" colspan="1">0.0283 (11)</td>
<td rowspan="1" colspan="1">0.0051 (7)</td>
<td rowspan="1" colspan="1">0.0074 (7)</td>
<td rowspan="1" colspan="1">−0.0038 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0173 (7)</td>
<td rowspan="1" colspan="1">0.0219 (8)</td>
<td rowspan="1" colspan="1">0.0277 (9)</td>
<td rowspan="1" colspan="1">−0.0067 (6)</td>
<td rowspan="1" colspan="1">0.0068 (7)</td>
<td rowspan="1" colspan="1">−0.0036 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0397 (12)</td>
<td rowspan="1" colspan="1">0.0158 (8)</td>
<td rowspan="1" colspan="1">0.0332 (11)</td>
<td rowspan="1" colspan="1">0.0009 (7)</td>
<td rowspan="1" colspan="1">0.0182 (10)</td>
<td rowspan="1" colspan="1">0.0080 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0326 (11)</td>
<td rowspan="1" colspan="1">0.0517 (14)</td>
<td rowspan="1" colspan="1">0.0278 (11)</td>
<td rowspan="1" colspan="1">0.0189 (10)</td>
<td rowspan="1" colspan="1">0.0115 (9)</td>
<td rowspan="1" colspan="1">0.0219 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">O12</td>
<td rowspan="1" colspan="1">0.0160 (6)</td>
<td rowspan="1" colspan="1">0.0326 (7)</td>
<td rowspan="1" colspan="1">0.0230 (7)</td>
<td rowspan="1" colspan="1">0.0034 (5)</td>
<td rowspan="1" colspan="1">0.0079 (5)</td>
<td rowspan="1" colspan="1">−0.0044 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O11</td>
<td rowspan="1" colspan="1">0.0188 (6)</td>
<td rowspan="1" colspan="1">0.0506 (9)</td>
<td rowspan="1" colspan="1">0.0112 (6)</td>
<td rowspan="1" colspan="1">−0.0003 (6)</td>
<td rowspan="1" colspan="1">0.0060 (5)</td>
<td rowspan="1" colspan="1">−0.0021 (6)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e1268"><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">2.1660 (13)</td>
<td rowspan="1" colspan="1">O2W—H4W</td>
<td rowspan="1" colspan="1">0.79 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O1W<sup>i</sup>
</td>
<td rowspan="1" colspan="1">2.1660 (13)</td>
<td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.515 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O2W</td>
<td rowspan="1" colspan="1">2.2455 (12)</td>
<td rowspan="1" colspan="1">C3—C2</td>
<td rowspan="1" colspan="1">1.529 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O2W<sup>i</sup>
</td>
<td rowspan="1" colspan="1">2.2455 (12)</td>
<td rowspan="1" colspan="1">C3—H3A</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—Cl1</td>
<td rowspan="1" colspan="1">2.5102 (5)</td>
<td rowspan="1" colspan="1">C3—H3B</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">2.5102 (5)</td>
<td rowspan="1" colspan="1">C4—H4A</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—O12</td>
<td rowspan="1" colspan="1">1.4456 (14)</td>
<td rowspan="1" colspan="1">C4—H4B</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—O11</td>
<td rowspan="1" colspan="1">1.4478 (16)</td>
<td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.518 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C4</td>
<td rowspan="1" colspan="1">1.7730 (18)</td>
<td rowspan="1" colspan="1">C1—H1A</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1</td>
<td rowspan="1" colspan="1">1.7820 (19)</td>
<td rowspan="1" colspan="1">C1—H1B</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—H1W</td>
<td rowspan="1" colspan="1">0.758 (16)</td>
<td rowspan="1" colspan="1">C2—H2A</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—H2W</td>
<td rowspan="1" colspan="1">0.812 (17)</td>
<td rowspan="1" colspan="1">C2—H2B</td>
<td rowspan="1" colspan="1">0.97</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W—H3W</td>
<td rowspan="1" colspan="1">0.830 (16)</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—O1W<sup>i</sup>
</td>
<td rowspan="1" colspan="1">168.24 (8)</td>
<td rowspan="1" colspan="1">H3W—O2W—H4W</td>
<td rowspan="1" colspan="1">115 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—O2W</td>
<td rowspan="1" colspan="1">88.05 (5)</td>
<td rowspan="1" colspan="1">C4—C3—C2</td>
<td rowspan="1" colspan="1">106.16 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>i</sup>
—Co1—O2W</td>
<td rowspan="1" colspan="1">83.27 (5)</td>
<td rowspan="1" colspan="1">C4—C3—H3A</td>
<td rowspan="1" colspan="1">110.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—O2W<sup>i</sup>
</td>
<td rowspan="1" colspan="1">83.27 (5)</td>
<td rowspan="1" colspan="1">C2—C3—H3A</td>
<td rowspan="1" colspan="1">110.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>i</sup>
—Co1—O2W<sup>i</sup>
</td>
<td rowspan="1" colspan="1">88.05 (5)</td>
<td rowspan="1" colspan="1">C4—C3—H3B</td>
<td rowspan="1" colspan="1">110.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W—Co1—O2W<sup>i</sup>
</td>
<td rowspan="1" colspan="1">84.92 (7)</td>
<td rowspan="1" colspan="1">C2—C3—H3B</td>
<td rowspan="1" colspan="1">110.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—Cl1</td>
<td rowspan="1" colspan="1">95.34 (4)</td>
<td rowspan="1" colspan="1">H3A—C3—H3B</td>
<td rowspan="1" colspan="1">108.7</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>i</sup>
—Co1—Cl1</td>
<td rowspan="1" colspan="1">92.24 (4)</td>
<td rowspan="1" colspan="1">C3—C4—S1</td>
<td rowspan="1" colspan="1">103.73 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W—Co1—Cl1</td>
<td rowspan="1" colspan="1">171.61 (4)</td>
<td rowspan="1" colspan="1">C3—C4—H4A</td>
<td rowspan="1" colspan="1">111</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W<sup>i</sup>
—Co1—Cl1</td>
<td rowspan="1" colspan="1">87.85 (3)</td>
<td rowspan="1" colspan="1">S1—C4—H4A</td>
<td rowspan="1" colspan="1">111</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W—Co1—Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">92.24 (4)</td>
<td rowspan="1" colspan="1">C3—C4—H4B</td>
<td rowspan="1" colspan="1">111</td>
</tr>
<tr><td rowspan="1" colspan="1">O1W<sup>i</sup>
—Co1—Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">95.34 (4)</td>
<td rowspan="1" colspan="1">S1—C4—H4B</td>
<td rowspan="1" colspan="1">111</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W—Co1—Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">87.85 (3)</td>
<td rowspan="1" colspan="1">H4A—C4—H4B</td>
<td rowspan="1" colspan="1">109</td>
</tr>
<tr><td rowspan="1" colspan="1">O2W<sup>i</sup>
—Co1—Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">171.61 (4)</td>
<td rowspan="1" colspan="1">C2—C1—S1</td>
<td rowspan="1" colspan="1">105.63 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">Cl1—Co1—Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">99.66 (2)</td>
<td rowspan="1" colspan="1">C2—C1—H1A</td>
<td rowspan="1" colspan="1">110.6</td>
</tr>
<tr><td rowspan="1" colspan="1">O12—S1—O11</td>
<td rowspan="1" colspan="1">116.50 (9)</td>
<td rowspan="1" colspan="1">S1—C1—H1A</td>
<td rowspan="1" colspan="1">110.6</td>
</tr>
<tr><td rowspan="1" colspan="1">O12—S1—C4</td>
<td rowspan="1" colspan="1">110.32 (9)</td>
<td rowspan="1" colspan="1">C2—C1—H1B</td>
<td rowspan="1" colspan="1">110.6</td>
</tr>
<tr><td rowspan="1" colspan="1">O11—S1—C4</td>
<td rowspan="1" colspan="1">109.92 (10)</td>
<td rowspan="1" colspan="1">S1—C1—H1B</td>
<td rowspan="1" colspan="1">110.6</td>
</tr>
<tr><td rowspan="1" colspan="1">O12—S1—C1</td>
<td rowspan="1" colspan="1">112.01 (10)</td>
<td rowspan="1" colspan="1">H1A—C1—H1B</td>
<td rowspan="1" colspan="1">108.7</td>
</tr>
<tr><td rowspan="1" colspan="1">O11—S1—C1</td>
<td rowspan="1" colspan="1">109.14 (10)</td>
<td rowspan="1" colspan="1">C1—C2—C3</td>
<td rowspan="1" colspan="1">107.97 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—S1—C1</td>
<td rowspan="1" colspan="1">97.26 (10)</td>
<td rowspan="1" colspan="1">C1—C2—H2A</td>
<td rowspan="1" colspan="1">110.1</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O1W—H1W</td>
<td rowspan="1" colspan="1">114 (2)</td>
<td rowspan="1" colspan="1">C3—C2—H2A</td>
<td rowspan="1" colspan="1">110.1</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O1W—H2W</td>
<td rowspan="1" colspan="1">120 (2)</td>
<td rowspan="1" colspan="1">C1—C2—H2B</td>
<td rowspan="1" colspan="1">110.1</td>
</tr>
<tr><td rowspan="1" colspan="1">H1W—O1W—H2W</td>
<td rowspan="1" colspan="1">118 (3)</td>
<td rowspan="1" colspan="1">C3—C2—H2B</td>
<td rowspan="1" colspan="1">110.1</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O2W—H3W</td>
<td rowspan="1" colspan="1">114.7 (17)</td>
<td rowspan="1" colspan="1">H2A—C2—H2B</td>
<td rowspan="1" colspan="1">108.4</td>
</tr>
<tr><td rowspan="1" colspan="1">Co1—O2W—H4W</td>
<td rowspan="1" colspan="1">106.8 (18)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4—S1</td>
<td rowspan="1" colspan="1">−42.0 (2)</td>
<td rowspan="1" colspan="1">O11—S1—C1—C2</td>
<td rowspan="1" colspan="1">115.94 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">O12—S1—C4—C3</td>
<td rowspan="1" colspan="1">140.20 (15)</td>
<td rowspan="1" colspan="1">C4—S1—C1—C2</td>
<td rowspan="1" colspan="1">1.88 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">O11—S1—C4—C3</td>
<td rowspan="1" colspan="1">−89.99 (17)</td>
<td rowspan="1" colspan="1">S1—C1—C2—C3</td>
<td rowspan="1" colspan="1">−27.0 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—S1—C4—C3</td>
<td rowspan="1" colspan="1">23.45 (17)</td>
<td rowspan="1" colspan="1">C4—C3—C2—C1</td>
<td rowspan="1" colspan="1">45.6 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O12—S1—C1—C2</td>
<td rowspan="1" colspan="1">−113.53 (17)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
<p>Symmetry code: (i) −<italic>x</italic>
+1, <italic>y</italic>
, −<italic>z</italic>
+1/2.</p>
</sec>
<sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title>
<table-wrap position="anchor" id="d1e1755"><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>
—H1<italic>W</italic>
···Cl1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.77 (3)</td>
<td rowspan="1" colspan="1">2.44 (3)</td>
<td rowspan="1" colspan="1">3.1885 (15)</td>
<td rowspan="1" colspan="1">165 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1<italic>W</italic>
—H2<italic>W</italic>
···O11</td>
<td rowspan="1" colspan="1">0.81 (2)</td>
<td rowspan="1" colspan="1">1.99 (2)</td>
<td rowspan="1" colspan="1">2.782 (2)</td>
<td rowspan="1" colspan="1">165 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2<italic>W</italic>
—H3<italic>W</italic>
···Cl1<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">0.83 (2)</td>
<td rowspan="1" colspan="1">2.41 (2)</td>
<td rowspan="1" colspan="1">3.2289 (16)</td>
<td rowspan="1" colspan="1">171 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2<italic>W</italic>
—H4<italic>W</italic>
···O12</td>
<td rowspan="1" colspan="1">0.79 (3)</td>
<td rowspan="1" colspan="1">2.05 (3)</td>
<td rowspan="1" colspan="1">2.835 (2)</td>
<td rowspan="1" colspan="1">174 (3)</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (ii) −<italic>x</italic>
+1, −<italic>y</italic>
+1, −<italic>z</italic>
; (iii) <italic>x</italic>
, −<italic>y</italic>
+1, <italic>z</italic>
+1/2.</p>
</sec>
</app>
</app-group>
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</back>
<floats-group><table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (, )</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>
H1<italic>W</italic>
Cl1<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.77(3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.44(3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.1885(15)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">165(3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1<italic>W</italic>
H2<italic>W</italic>
O11</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.81(2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.99(2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.782(2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">165(2)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O2<italic>W</italic>
H3<italic>W</italic>
Cl1<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.83(2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.41(2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.2289(16)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">171(2)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O2<italic>W</italic>
H4<italic>W</italic>
O12</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.79(3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.05(3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.835(2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">174(3)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-71-00m16-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-71-00m16-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>
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