trans-Diaquabis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole]nickel(II) bis(tetrafluoridoborate)
Identifieur interne : 000029 ( Pmc/Corpus ); précédent : 000028; suivant : 000030trans-Diaquabis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole]nickel(II) bis(tetrafluoridoborate)
Auteurs : Fouad Bentiss ; Frédéric Capet ; Michel Lagrenée ; Mohamed Saadi ; Lahcen El AmmariSource :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2011.
Abstract
The bidentate 1,3,4-thiadiazole ligand, namely, 2,5-bis(2-pyridyl)-1,3,4-thiadiazole (denoted
Url:
DOI: 10.1107/S1600536811026420
PubMed: 22090840
PubMed Central: 3212138
Links to Exploration step
PMC:3212138Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en"><italic>trans</italic>-Diaquabis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole]nickel(II) bis(tetrafluoridoborate)</title><author><name sortKey="Bentiss, Fouad" sort="Bentiss, Fouad" uniqKey="Bentiss F" first="Fouad" last="Bentiss">Fouad Bentiss</name><affiliation><nlm:aff id="a">Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Capet, Frederic" sort="Capet, Frederic" uniqKey="Capet F" first="Frédéric" last="Capet">Frédéric Capet</name><affiliation><nlm:aff id="b">Unité de Catalyse et de Chimie du Solide (UCCS), CNRS UMR 8181, ENSCL, BP 90108, F-59652 Villeneuve d’Ascq Cedex, France, Université Lille Nord de France, F-59000 Lille,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Lagrenee, Michel" sort="Lagrenee, Michel" uniqKey="Lagrenee M" first="Michel" last="Lagrenée">Michel Lagrenée</name><affiliation><nlm:aff id="b">Unité de Catalyse et de Chimie du Solide (UCCS), CNRS UMR 8181, ENSCL, BP 90108, F-59652 Villeneuve d’Ascq Cedex, France, Université Lille Nord de France, F-59000 Lille,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Saadi, Mohamed" sort="Saadi, Mohamed" uniqKey="Saadi M" first="Mohamed" last="Saadi">Mohamed Saadi</name><affiliation><nlm:aff id="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="El Ammari, Lahcen" sort="El Ammari, Lahcen" uniqKey="El Ammari L" first="Lahcen" last="El Ammari">Lahcen El Ammari</name><affiliation><nlm:aff id="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">22090840</idno><idno type="pmc">3212138</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3212138</idno><idno type="RBID">PMC:3212138</idno><idno type="doi">10.1107/S1600536811026420</idno><date when="2011">2011</date><idno type="wicri:Area/Pmc/Corpus">000029</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000029</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main"><italic>trans</italic>-Diaquabis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole]nickel(II) bis(tetrafluoridoborate)</title><author><name sortKey="Bentiss, Fouad" sort="Bentiss, Fouad" uniqKey="Bentiss F" first="Fouad" last="Bentiss">Fouad Bentiss</name><affiliation><nlm:aff id="a">Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Capet, Frederic" sort="Capet, Frederic" uniqKey="Capet F" first="Frédéric" last="Capet">Frédéric Capet</name><affiliation><nlm:aff id="b">Unité de Catalyse et de Chimie du Solide (UCCS), CNRS UMR 8181, ENSCL, BP 90108, F-59652 Villeneuve d’Ascq Cedex, France, Université Lille Nord de France, F-59000 Lille,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Lagrenee, Michel" sort="Lagrenee, Michel" uniqKey="Lagrenee M" first="Michel" last="Lagrenée">Michel Lagrenée</name><affiliation><nlm:aff id="b">Unité de Catalyse et de Chimie du Solide (UCCS), CNRS UMR 8181, ENSCL, BP 90108, F-59652 Villeneuve d’Ascq Cedex, France, Université Lille Nord de France, F-59000 Lille,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Saadi, Mohamed" sort="Saadi, Mohamed" uniqKey="Saadi M" first="Mohamed" last="Saadi">Mohamed Saadi</name><affiliation><nlm:aff id="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="El Ammari, Lahcen" sort="El Ammari, Lahcen" uniqKey="El Ammari L" first="Lahcen" last="El Ammari">Lahcen El Ammari</name><affiliation><nlm:aff id="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</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="2011">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The bidentate 1,3,4-thiadiazole ligand, namely, 2,5-bis(2-pyridyl)-1,3,4-thiadiazole (denoted <italic>L</italic>), untested as a polydentate ligand, has been found to form the monomeric title complex, [Ni(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>](BF<sub>4</sub>)<sub>2</sub>. The complex shows an octahedral environment of the nickel cation in which the Ni<sup>2+</sup> ion is located on a center of symmetry, linked to two ligands and two water molecules. In this 1:2 complex (one metal for two organic ligands) each thiadiazole ligand uses one pyridyl and one thiadiazole N atom for chelate binding. In the second pyridyl substituent, the N atom is oriented towards the same direction as the S atom of the 1,3,4-thiadiazole ring. The mean plane of the thiadiazole and pyridyl rings linked to the nickel cation forms a dihedral angle with the other pyridine ring of 18.63 (8)°. The tetrafluoridoborate ions can be regarded as free anions in the crystal lattice. Nevertheless, they are involved in an infinite two-dimensional network parallel to (<inline-formula><inline-graphic xlink:href="e-67-m1052-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>01) through O—H⋯F hydrogen bonds.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></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="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">22090840</article-id><article-id pub-id-type="pmc">3212138</article-id><article-id pub-id-type="publisher-id">dn2703</article-id><article-id pub-id-type="doi">10.1107/S1600536811026420</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536811026420</article-id><article-categories><subj-group subj-group-type="heading"><subject>Metal-Organic Papers</subject></subj-group></article-categories><title-group><article-title><italic>trans</italic>-Diaquabis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole]nickel(II) bis(tetrafluoridoborate)</article-title><alt-title><italic>[Ni(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>](BF<sub>4</sub>)<sub>2</sub></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Bentiss</surname><given-names>Fouad</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>Capet</surname><given-names>Frédéric</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Lagrenée</surname><given-names>Michel</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Saadi</surname><given-names>Mohamed</given-names></name><xref ref-type="aff" rid="c">c</xref></contrib><contrib contrib-type="author"><name><surname>El Ammari</surname><given-names>Lahcen</given-names></name><xref ref-type="aff" rid="c">c</xref></contrib><aff id="a"><label>a</label>Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></aff><aff id="b"><label>b</label>Unité de Catalyse et de Chimie du Solide (UCCS), CNRS UMR 8181, ENSCL, BP 90108, F-59652 Villeneuve d’Ascq Cedex, France, Université Lille Nord de France, F-59000 Lille,<country>France</country></aff><aff id="c"><label>c</label>Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>f_bentiss@yahoo.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>8</month><year>2011</year></pub-date><pub-date pub-type="epub"><day>09</day><month>7</month><year>2011</year></pub-date><pub-date pub-type="pmc-release"><day>09</day><month>7</month><year>2011</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>67</volume><issue>Pt 8</issue><issue-id pub-id-type="publisher-id">e110800</issue-id><fpage>m1052</fpage><lpage>m1053</lpage><history><date date-type="received"><day>30</day><month>6</month><year>2011</year></date><date date-type="accepted"><day>03</day><month>7</month><year>2011</year></date></history><permissions><copyright-statement>© Bentiss et al. 2011</copyright-statement><copyright-year>2011</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/S1600536811026420">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>The bidentate 1,3,4-thiadiazole ligand, namely, 2,5-bis(2-pyridyl)-1,3,4-thiadiazole (denoted <italic>L</italic>), untested as a polydentate ligand, has been found to form the monomeric title complex, [Ni(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>](BF<sub>4</sub>)<sub>2</sub>. The complex shows an octahedral environment of the nickel cation in which the Ni<sup>2+</sup> ion is located on a center of symmetry, linked to two ligands and two water molecules. In this 1:2 complex (one metal for two organic ligands) each thiadiazole ligand uses one pyridyl and one thiadiazole N atom for chelate binding. In the second pyridyl substituent, the N atom is oriented towards the same direction as the S atom of the 1,3,4-thiadiazole ring. The mean plane of the thiadiazole and pyridyl rings linked to the nickel cation forms a dihedral angle with the other pyridine ring of 18.63 (8)°. The tetrafluoridoborate ions can be regarded as free anions in the crystal lattice. Nevertheless, they are involved in an infinite two-dimensional network parallel to (<inline-formula><inline-graphic xlink:href="e-67-m1052-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>01) through O—H⋯F hydrogen bonds.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature</title><p>For Ni<sup>II</sup> and Cu<sup>II</sup> complexes containing a five azide ring, see: Keij <italic>et al.</italic> (1984<xref ref-type="bibr" rid="bb8"> ▶</xref>). For background to similar structures, see: Bentiss <italic>et al.</italic> (2002<xref ref-type="bibr" rid="bb3"> ▶</xref>, 2004<xref ref-type="bibr" rid="bb2"> ▶</xref>, 2011<xref ref-type="bibr" rid="bb1"> ▶</xref>); Zheng <italic>et al.</italic> (2006<xref ref-type="bibr" rid="bb11"> ▶</xref>). For an improved synthesis of the ligand, see: Lebrini <italic>et al.</italic> (2005<xref ref-type="bibr" rid="bb9"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-67-m1052-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"><list-item><p>[Ni(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>](BF<sub>4</sub>)<sub>2</sub></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 748.93</p></list-item><list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-67-m1052-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 10.8164 (15) Å</p></list-item><list-item><p><italic>b</italic> = 11.0126 (13) Å</p></list-item><list-item><p><italic>c</italic> = 13.2333 (16) Å</p></list-item><list-item><p>β = 101.455 (6)°</p></list-item><list-item><p><italic>V</italic> = 1544.9 (3) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 2</p></list-item><list-item><p>Mo <italic>K</italic>α radiation</p></list-item><list-item><p>μ = 0.85 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 100 K</p></list-item><list-item><p>0.26 × 0.21 × 0.13 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection</title><p><list list-type="simple"><list-item><p>Bruker X8 APEXII CCD area-detector diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2005<xref ref-type="bibr" rid="bb4"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.809, <italic>T</italic><sub>max</sub> = 0.898</p></list-item><list-item><p>28021 measured reflections</p></list-item><list-item><p>3120 independent reflections</p></list-item><list-item><p>2729 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.035</p></list-item></list></p></sec><sec id="sec2.1.3"><title>Refinement</title><p><list list-type="simple"><list-item><p><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.029</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.073</p></list-item><list-item><p><italic>S</italic> = 1.05</p></list-item><list-item><p>3120 reflections</p></list-item><list-item><p>214 parameters</p></list-item><list-item><p>H-atom parameters constrained</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.60 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.40 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e505"><title></title><p>Data collection: <italic>APEX2</italic> (Bruker, 2005<xref ref-type="bibr" rid="bb4"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2005<xref ref-type="bibr" rid="bb4"> ▶</xref>); data reduction: <italic>SAINT</italic>; program(s) used to solve structure: <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb10"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb10"> ▶</xref>); molecular graphics: <italic>ORTEPIII</italic> (Burnett & Johnson, 1996<xref ref-type="bibr" rid="bb5"> ▶</xref>) and <italic>ORTEP-3 for Windows</italic> (Farrugia, 1997<xref ref-type="bibr" rid="bb6"> ▶</xref>); software used to prepare material for publication: <italic>WinGX</italic> (Farrugia, 1999<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" xlink:href="e-67-m1052-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablock(s) I, global. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536811026420/dn2703sup1.cif">10.1107/S1600536811026420/dn2703sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-67-m1052-sup1.cif" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material content-type="local-data" xlink:href="e-67-m1052-Isup2.hkl" position="float" xlink:type="simple"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536811026420/dn2703Isup2.hkl">10.1107/S1600536811026420/dn2703Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-67-m1052-Isup2.hkl" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material position="float" xlink:type="simple"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?dn2703&file=dn2703sup0.html&mime=text/html" xlink:type="simple"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?dn2703sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?dn2703&checkcif=yes" xlink:type="simple">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?dn2703">DN2703</ext-link>).</p></fn></fn-group><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>With ligands containing a five azide ring, 3 d transition metals such as Ni<sup>II</sup>and Cu<sup>II</sup> have a tendency to form mono or polynuclear species (Keij <italic>et
al.</italic>, 1984). The dinuclear species are of interest due to their
potential
magnetic coupling. The unpaired 3 d electrons being potentially coupled
<italic>via</italic> the intermediary of the bridging azide ligands. The ligands related
to the 1,2-diazoles with <italic>o</italic>-pyridine substitution at the 3 and 5
positions, such as 2,5-bis(2-pyridyl)-1,3,4 oxadiazole and thiadiazole, have
been of interest for such applications. Indeed, 2,5-bis(2-pyridyl)
-1,3,4-thiadiazole can be used as a molecular architect with transition metals
in association with anionic Ni-ligands. In the resulting di and mononuclear
complexes, a variety of coordination modes have been observed, of which the
dinuclear (N`N``, N2, N``) bridging, the dinuclear (N`N``, N2, N``)2 double
bridging and the monoclear (N`,<italic>N</italic>`)2 coordination mode are the most
common and the most important ones (Scheme 1), the latter mode, the
<italic>trans</italic> type is exclusively observed for featuring octahedral complexes.</p><p>The structures of monomeric complexes of the neutral 2,5-bis(2-pyridyl)-1,
3,4-thiadiazole derivative with divalent Zn (tetrachloride and perchlorate),
Co (nitrate, perchlorate and tetrafluoborate), Ni (perchlorate), and Cu
(nitrate, perchlorate) have been previously reported (Bentiss <italic>et al.</italic>,
2002; Bentiss <italic>et al.</italic>,2004; Zheng <italic>et al.</italic>2006; Bentiss <italic>et
al.</italic>, 2011). We report here the synthesis and the single-crystal
structure
of the new monomeric complexe formed by 2,5-bis(2-pyridyl)-1,3,4-thiadiazole
with nickel tetrafluoroborate as counter ions.</p><p>The complexe shows an almost regular octahedral environment of the nickel
cation in wich Ni<sup>2+</sup> is located at a center of symmetry, and linked to two
ligand and two water molecules as shown in Fig.1. As a matter of fact, the
nickel coordination sphere is achieved by interaction with the nitrogen atom
of a single pyridyl ring and with the near nitrogen of the azide group with
Ni—N distances in the range of 2.052 (2)—2.132 (2) Å. Moreover, the water
molecules are found in axial positions at distances and angles of Ni—O
2.120 (2) Å and all N—Ni—O angles being close to 90 °.</p><p>The dihedral angle between the thiadiazole and the pyridyl rings linked to the
nickel cation is in the range of 4.16 (9)°. The mean plane of the two
preceding cycles forms a dihedral angle with the
(N4—C8—C9—C10—C11—C12) other pyridine ring of 18.63 (8)°. The
counter ion, BF<sub>4</sub><sup>-</sup> is involved in an infinite two-dimensional network of
O—H···F hydrogen bonds parallel to the (-1 0 1) plane (Table 1, Fig.1).</p></sec><sec id="experimental"><title>Experimental </title><p>2,5-Bis(2-pyridyl)-1,3,4-thiadiazole ligand (noted <italic>L</italic>) was synthesized as
described previously by Lebrini <italic>et al.</italic>, 2005. Ni(BF<sub>4</sub>)<sub>2</sub>6H<sub>2</sub>O
(1.5 mmol, 0.51 g) in 8 ml of water was added to (0.42 mmol, 0.1 g) of <italic>L</italic>(bptd ligand) dissolved in 8 ml of ethanol. The solution was filtered and
after 24 h, the colorless compound crystallized at room temperature. Crystals
were washed with water and dried under vacuum. Yield: 51%. Anal. Calc. for
C<sub>24</sub>H<sub>20</sub>B<sub>2</sub>F<sub>8</sub>N<sub>8</sub>NiO<sub>2</sub>S<sub>2</sub>: C, 38.44; H, 2.67; N, 14.95; S, 8.56; F,
20.29%. Found: C, 38.52; H, 2.75; N, 14.90; S, 8.53; F, 20.27%.</p></sec><sec id="refinement"><title>Refinement </title><p>H atoms attached to carbon were located in a difference map but introduced in
calculated position and treated as riding with C—H = 0.95 Å for the
aromatic CH, with <italic>U</italic><sub>iso</sub>(H) = 1.2 <italic>U</italic><sub>eq</sub> (aromatic). The O-bound
H atom were initially located in a difference map and refined with O—H
distance restraints of 0.86 (1). In the the last cycles of refinement, they are
treated as riding on their parent O atoms with <italic>U</italic><sub>iso</sub>(H) set to
1.2<italic>U</italic><sub>eq</sub>(O).</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>Plot of the crystal structure showing the molecules linked to the nickel cation and the counter ions, BF4-, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles. Hydrogen bonds are shown as dashed lines.</p></caption><graphic xlink:href="e-67-m1052-fig1"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e203"><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">[Ni(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>](BF<sub>4</sub>)<sub>2</sub></td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 756</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 748.93</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.610 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>n</italic></td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 2yn</td><td rowspan="1" colspan="1">Cell parameters from 3120 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 10.8164 (15) Å</td><td rowspan="1" colspan="1">θ = 2.7–26.3°</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.0126 (13) Å</td><td rowspan="1" colspan="1">µ = 0.85 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 13.2333 (16) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 100 K</td></tr><tr><td rowspan="1" colspan="1">β = 101.455 (6)°</td><td rowspan="1" colspan="1">Prism, colourless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1544.9 (3) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.26 × 0.21 × 0.13 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e346"><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 X8 APEXII CCD area-detector diffractometer</td><td rowspan="1" colspan="1">3120 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">2729 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">graphite</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.035</td></tr><tr><td rowspan="1" colspan="1">φ and ω scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 26.3°, θ<sub>min</sub> = 2.7°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2005)</td><td rowspan="1" colspan="1"><italic>h</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.809, <italic>T</italic><sub>max</sub> = 0.898</td><td rowspan="1" colspan="1"><italic>k</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1">28021 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −16→16</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e463"><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>)] = 0.029</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>) = 0.073</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.05</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0302<italic>P</italic>)<sup>2</sup> + 1.3259<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">3120 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">214 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.60 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">0 restraints</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.40 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="d1e620"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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> >
2σ(<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="d1e719"><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">B1</td><td rowspan="1" colspan="1">0.5722 (2)</td><td rowspan="1" colspan="1">0.6450 (2)</td><td rowspan="1" colspan="1">0.25602 (17)</td><td rowspan="1" colspan="1">0.0236 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">F1</td><td rowspan="1" colspan="1">0.67390 (15)</td><td rowspan="1" colspan="1">0.59474 (18)</td><td rowspan="1" colspan="1">0.32316 (11)</td><td rowspan="1" colspan="1">0.0707 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">F2</td><td rowspan="1" colspan="1">0.58436 (11)</td><td rowspan="1" colspan="1">0.62341 (12)</td><td rowspan="1" colspan="1">0.15219 (9)</td><td rowspan="1" colspan="1">0.0362 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">F3</td><td rowspan="1" colspan="1">0.46260 (14)</td><td rowspan="1" colspan="1">0.59379 (14)</td><td rowspan="1" colspan="1">0.27433 (14)</td><td rowspan="1" colspan="1">0.0583 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">F4</td><td rowspan="1" colspan="1">0.56853 (15)</td><td rowspan="1" colspan="1">0.77036 (12)</td><td rowspan="1" colspan="1">0.27479 (11)</td><td rowspan="1" colspan="1">0.0494 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.40875 (16)</td><td rowspan="1" colspan="1">0.75569 (16)</td><td rowspan="1" colspan="1">−0.02295 (14)</td><td rowspan="1" colspan="1">0.0202 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.47768 (16)</td><td rowspan="1" colspan="1">1.25248 (17)</td><td rowspan="1" colspan="1">0.06948 (13)</td><td rowspan="1" colspan="1">0.0200 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.43547 (18)</td><td rowspan="1" colspan="1">1.35965 (17)</td><td rowspan="1" colspan="1">0.10676 (14)</td><td rowspan="1" colspan="1">0.0236 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.4806</td><td rowspan="1" colspan="1">1.4333</td><td rowspan="1" colspan="1">0.1048</td><td rowspan="1" colspan="1">0.028*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.32542 (18)</td><td rowspan="1" colspan="1">1.35711 (18)</td><td rowspan="1" colspan="1">0.14729 (15)</td><td rowspan="1" colspan="1">0.0258 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.2940</td><td rowspan="1" colspan="1">1.4292</td><td rowspan="1" colspan="1">0.1726</td><td rowspan="1" colspan="1">0.031*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.26311 (18)</td><td rowspan="1" colspan="1">1.24770 (18)</td><td rowspan="1" colspan="1">0.14982 (15)</td><td rowspan="1" colspan="1">0.0265 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.1883</td><td rowspan="1" colspan="1">1.2433</td><td rowspan="1" colspan="1">0.1770</td><td rowspan="1" colspan="1">0.032*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.31231 (18)</td><td rowspan="1" colspan="1">1.14360 (18)</td><td rowspan="1" colspan="1">0.11167 (15)</td><td rowspan="1" colspan="1">0.0248 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6</td><td rowspan="1" colspan="1">0.2696</td><td rowspan="1" colspan="1">1.0686</td><td rowspan="1" colspan="1">0.1144</td><td rowspan="1" colspan="1">0.030*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.22180 (17)</td><td rowspan="1" colspan="1">0.74859 (17)</td><td rowspan="1" colspan="1">0.04687 (14)</td><td rowspan="1" colspan="1">0.0210 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.10347 (17)</td><td rowspan="1" colspan="1">0.71642 (18)</td><td rowspan="1" colspan="1">0.08024 (14)</td><td rowspan="1" colspan="1">0.0222 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.01756 (18)</td><td rowspan="1" colspan="1">0.80507 (19)</td><td rowspan="1" colspan="1">0.09554 (16)</td><td rowspan="1" colspan="1">0.0296 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">0.0335</td><td rowspan="1" colspan="1">0.8887</td><td rowspan="1" colspan="1">0.0859</td><td rowspan="1" colspan="1">0.036*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">−0.09264 (19)</td><td rowspan="1" colspan="1">0.7670 (2)</td><td rowspan="1" colspan="1">0.12544 (17)</td><td rowspan="1" colspan="1">0.0342 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">−0.1541</td><td rowspan="1" colspan="1">0.8246</td><td rowspan="1" colspan="1">0.1364</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">−0.11154 (19)</td><td rowspan="1" colspan="1">0.6445 (2)</td><td rowspan="1" colspan="1">0.13902 (16)</td><td rowspan="1" colspan="1">0.0329 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">−0.1862</td><td rowspan="1" colspan="1">0.6166</td><td rowspan="1" colspan="1">0.1591</td><td rowspan="1" colspan="1">0.040*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">−0.0195 (2)</td><td rowspan="1" colspan="1">0.5627 (2)</td><td rowspan="1" colspan="1">0.12282 (16)</td><td rowspan="1" colspan="1">0.0310 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">−0.0326</td><td rowspan="1" colspan="1">0.4787</td><td rowspan="1" colspan="1">0.1334</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Ni1</td><td rowspan="1" colspan="1">0.5000</td><td rowspan="1" colspan="1">1.0000</td><td rowspan="1" colspan="1">0.0000</td><td rowspan="1" colspan="1">0.01936 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.41765 (14)</td><td rowspan="1" colspan="1">1.14452 (14)</td><td rowspan="1" colspan="1">0.07112 (12)</td><td rowspan="1" colspan="1">0.0218 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.38061 (14)</td><td rowspan="1" colspan="1">0.85992 (14)</td><td rowspan="1" colspan="1">0.01661 (12)</td><td rowspan="1" colspan="1">0.0210 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.27253 (14)</td><td rowspan="1" colspan="1">0.85652 (14)</td><td rowspan="1" colspan="1">0.05732 (12)</td><td rowspan="1" colspan="1">0.0226 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.08724 (15)</td><td rowspan="1" colspan="1">0.59655 (15)</td><td rowspan="1" colspan="1">0.09286 (13)</td><td rowspan="1" colspan="1">0.0260 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.61598 (13)</td><td rowspan="1" colspan="1">0.95553 (13)</td><td rowspan="1" colspan="1">0.14395 (11)</td><td rowspan="1" colspan="1">0.0307 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1W</td><td rowspan="1" colspan="1">0.6844</td><td rowspan="1" colspan="1">0.9932</td><td rowspan="1" colspan="1">0.1692</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2W</td><td rowspan="1" colspan="1">0.6090</td><td rowspan="1" colspan="1">0.9007</td><td rowspan="1" colspan="1">0.1886</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.30384 (4)</td><td rowspan="1" colspan="1">0.64191 (4)</td><td rowspan="1" colspan="1">−0.01275 (4)</td><td rowspan="1" colspan="1">0.02147 (12)</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="d1e1182"><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">B1</td><td rowspan="1" colspan="1">0.0194 (10)</td><td rowspan="1" colspan="1">0.0233 (11)</td><td rowspan="1" colspan="1">0.0268 (11)</td><td rowspan="1" colspan="1">0.0023 (8)</td><td rowspan="1" colspan="1">0.0017 (8)</td><td rowspan="1" colspan="1">0.0008 (9)</td></tr><tr><td rowspan="1" colspan="1">F1</td><td rowspan="1" colspan="1">0.0620 (10)</td><td rowspan="1" colspan="1">0.1029 (14)</td><td rowspan="1" colspan="1">0.0388 (8)</td><td rowspan="1" colspan="1">0.0561 (10)</td><td rowspan="1" colspan="1">−0.0106 (7)</td><td rowspan="1" colspan="1">−0.0066 (9)</td></tr><tr><td rowspan="1" colspan="1">F2</td><td rowspan="1" colspan="1">0.0351 (7)</td><td rowspan="1" colspan="1">0.0440 (8)</td><td rowspan="1" colspan="1">0.0285 (6)</td><td rowspan="1" colspan="1">−0.0059 (6)</td><td rowspan="1" colspan="1">0.0039 (5)</td><td rowspan="1" colspan="1">−0.0035 (6)</td></tr><tr><td rowspan="1" colspan="1">F3</td><td rowspan="1" colspan="1">0.0514 (9)</td><td rowspan="1" colspan="1">0.0459 (9)</td><td rowspan="1" colspan="1">0.0907 (12)</td><td rowspan="1" colspan="1">−0.0177 (7)</td><td rowspan="1" colspan="1">0.0457 (9)</td><td rowspan="1" colspan="1">−0.0236 (8)</td></tr><tr><td rowspan="1" colspan="1">F4</td><td rowspan="1" colspan="1">0.0759 (10)</td><td rowspan="1" colspan="1">0.0240 (7)</td><td rowspan="1" colspan="1">0.0503 (8)</td><td rowspan="1" colspan="1">−0.0093 (7)</td><td rowspan="1" colspan="1">0.0178 (7)</td><td rowspan="1" colspan="1">−0.0030 (6)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0189 (9)</td><td rowspan="1" colspan="1">0.0170 (9)</td><td rowspan="1" colspan="1">0.0231 (9)</td><td rowspan="1" colspan="1">−0.0021 (7)</td><td rowspan="1" colspan="1">0.0004 (7)</td><td rowspan="1" colspan="1">0.0028 (7)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0188 (9)</td><td rowspan="1" colspan="1">0.0196 (9)</td><td rowspan="1" colspan="1">0.0203 (8)</td><td rowspan="1" colspan="1">−0.0010 (7)</td><td rowspan="1" colspan="1">0.0005 (7)</td><td rowspan="1" colspan="1">0.0021 (7)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0248 (10)</td><td rowspan="1" colspan="1">0.0184 (9)</td><td rowspan="1" colspan="1">0.0270 (10)</td><td rowspan="1" colspan="1">−0.0014 (7)</td><td rowspan="1" colspan="1">0.0034 (8)</td><td rowspan="1" colspan="1">0.0006 (8)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0283 (10)</td><td rowspan="1" colspan="1">0.0214 (10)</td><td rowspan="1" colspan="1">0.0283 (10)</td><td rowspan="1" colspan="1">0.0025 (8)</td><td rowspan="1" colspan="1">0.0073 (8)</td><td rowspan="1" colspan="1">−0.0018 (8)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0248 (10)</td><td rowspan="1" colspan="1">0.0258 (10)</td><td rowspan="1" colspan="1">0.0302 (10)</td><td rowspan="1" colspan="1">−0.0003 (8)</td><td rowspan="1" colspan="1">0.0090 (8)</td><td rowspan="1" colspan="1">0.0004 (8)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0243 (9)</td><td rowspan="1" colspan="1">0.0213 (10)</td><td rowspan="1" colspan="1">0.0297 (10)</td><td rowspan="1" colspan="1">−0.0038 (8)</td><td rowspan="1" colspan="1">0.0078 (8)</td><td rowspan="1" colspan="1">0.0001 (8)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0197 (9)</td><td rowspan="1" colspan="1">0.0197 (9)</td><td rowspan="1" colspan="1">0.0226 (9)</td><td rowspan="1" colspan="1">0.0002 (7)</td><td rowspan="1" colspan="1">0.0015 (7)</td><td rowspan="1" colspan="1">0.0009 (7)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0194 (9)</td><td rowspan="1" colspan="1">0.0246 (10)</td><td rowspan="1" colspan="1">0.0218 (9)</td><td rowspan="1" colspan="1">−0.0032 (8)</td><td rowspan="1" colspan="1">0.0020 (7)</td><td rowspan="1" colspan="1">−0.0011 (8)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0247 (10)</td><td rowspan="1" colspan="1">0.0270 (11)</td><td rowspan="1" colspan="1">0.0362 (11)</td><td rowspan="1" colspan="1">0.0009 (8)</td><td rowspan="1" colspan="1">0.0040 (8)</td><td rowspan="1" colspan="1">−0.0007 (9)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0246 (10)</td><td rowspan="1" colspan="1">0.0425 (13)</td><td rowspan="1" colspan="1">0.0365 (11)</td><td rowspan="1" colspan="1">0.0058 (9)</td><td rowspan="1" colspan="1">0.0086 (9)</td><td rowspan="1" colspan="1">−0.0034 (10)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0244 (10)</td><td rowspan="1" colspan="1">0.0476 (14)</td><td rowspan="1" colspan="1">0.0295 (10)</td><td rowspan="1" colspan="1">−0.0075 (9)</td><td rowspan="1" colspan="1">0.0116 (8)</td><td rowspan="1" colspan="1">−0.0016 (10)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0337 (11)</td><td rowspan="1" colspan="1">0.0290 (11)</td><td rowspan="1" colspan="1">0.0331 (11)</td><td rowspan="1" colspan="1">−0.0092 (9)</td><td rowspan="1" colspan="1">0.0131 (9)</td><td rowspan="1" colspan="1">0.0009 (9)</td></tr><tr><td rowspan="1" colspan="1">Ni1</td><td rowspan="1" colspan="1">0.01766 (17)</td><td rowspan="1" colspan="1">0.01400 (17)</td><td rowspan="1" colspan="1">0.02659 (18)</td><td rowspan="1" colspan="1">−0.00261 (13)</td><td rowspan="1" colspan="1">0.00479 (13)</td><td rowspan="1" colspan="1">−0.00057 (13)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0205 (8)</td><td rowspan="1" colspan="1">0.0182 (8)</td><td rowspan="1" colspan="1">0.0264 (8)</td><td rowspan="1" colspan="1">−0.0019 (6)</td><td rowspan="1" colspan="1">0.0039 (6)</td><td rowspan="1" colspan="1">0.0009 (6)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0186 (7)</td><td rowspan="1" colspan="1">0.0179 (8)</td><td rowspan="1" colspan="1">0.0267 (8)</td><td rowspan="1" colspan="1">−0.0013 (6)</td><td rowspan="1" colspan="1">0.0048 (6)</td><td rowspan="1" colspan="1">0.0000 (6)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0193 (8)</td><td rowspan="1" colspan="1">0.0208 (8)</td><td rowspan="1" colspan="1">0.0282 (8)</td><td rowspan="1" colspan="1">−0.0032 (6)</td><td rowspan="1" colspan="1">0.0056 (6)</td><td rowspan="1" colspan="1">0.0012 (7)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0267 (8)</td><td rowspan="1" colspan="1">0.0233 (9)</td><td rowspan="1" colspan="1">0.0299 (8)</td><td rowspan="1" colspan="1">−0.0047 (7)</td><td rowspan="1" colspan="1">0.0099 (7)</td><td rowspan="1" colspan="1">−0.0014 (7)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0270 (7)</td><td rowspan="1" colspan="1">0.0276 (8)</td><td rowspan="1" colspan="1">0.0337 (8)</td><td rowspan="1" colspan="1">−0.0075 (6)</td><td rowspan="1" colspan="1">−0.0030 (6)</td><td rowspan="1" colspan="1">0.0064 (6)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.0188 (2)</td><td rowspan="1" colspan="1">0.0158 (2)</td><td rowspan="1" colspan="1">0.0299 (2)</td><td rowspan="1" colspan="1">−0.00252 (17)</td><td rowspan="1" colspan="1">0.00479 (18)</td><td rowspan="1" colspan="1">0.00033 (18)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title><table-wrap position="anchor" id="d1e1651"><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">B1—F3</td><td rowspan="1" colspan="1">1.377 (3)</td><td rowspan="1" colspan="1">C7—S1</td><td rowspan="1" colspan="1">1.7517 (19)</td></tr><tr><td rowspan="1" colspan="1">B1—F1</td><td rowspan="1" colspan="1">1.385 (3)</td><td rowspan="1" colspan="1">C8—N4</td><td rowspan="1" colspan="1">1.346 (3)</td></tr><tr><td rowspan="1" colspan="1">B1—F4</td><td rowspan="1" colspan="1">1.404 (3)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.390 (3)</td></tr><tr><td rowspan="1" colspan="1">B1—F2</td><td rowspan="1" colspan="1">1.426 (2)</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.393 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—N2</td><td rowspan="1" colspan="1">1.322 (2)</td><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C1—C2<sup>i</sup></td><td rowspan="1" colspan="1">1.482 (2)</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.382 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—S1</td><td rowspan="1" colspan="1">1.7137 (18)</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C2—N1</td><td rowspan="1" colspan="1">1.357 (2)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.391 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.391 (3)</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C2—C1<sup>i</sup></td><td rowspan="1" colspan="1">1.482 (2)</td><td rowspan="1" colspan="1">C12—N4</td><td rowspan="1" colspan="1">1.345 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.400 (3)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">Ni1—N2</td><td rowspan="1" colspan="1">2.0515 (15)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.384 (3)</td><td rowspan="1" colspan="1">Ni1—N2<sup>i</sup></td><td rowspan="1" colspan="1">2.0515 (15)</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">Ni1—O1<sup>i</sup></td><td rowspan="1" colspan="1">2.1197 (14)</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.400 (3)</td><td rowspan="1" colspan="1">Ni1—O1</td><td rowspan="1" colspan="1">2.1197 (14)</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">Ni1—N1<sup>i</sup></td><td rowspan="1" colspan="1">2.1320 (16)</td></tr><tr><td rowspan="1" colspan="1">C6—N1</td><td rowspan="1" colspan="1">1.352 (2)</td><td rowspan="1" colspan="1">Ni1—N1</td><td rowspan="1" colspan="1">2.1320 (16)</td></tr><tr><td rowspan="1" colspan="1">C6—H6</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N2—N3</td><td rowspan="1" colspan="1">1.381 (2)</td></tr><tr><td rowspan="1" colspan="1">C7—N3</td><td rowspan="1" colspan="1">1.305 (2)</td><td rowspan="1" colspan="1">O1—H1W</td><td rowspan="1" colspan="1">0.8564</td></tr><tr><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.478 (2)</td><td rowspan="1" colspan="1">O1—H2W</td><td rowspan="1" colspan="1">0.8588</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">F3—B1—F1</td><td rowspan="1" colspan="1">108.98 (19)</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">120.4</td></tr><tr><td rowspan="1" colspan="1">F3—B1—F4</td><td rowspan="1" colspan="1">108.44 (17)</td><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">118.91 (18)</td></tr><tr><td rowspan="1" colspan="1">F1—B1—F4</td><td rowspan="1" colspan="1">109.02 (18)</td><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">F3—B1—F2</td><td rowspan="1" colspan="1">110.41 (17)</td><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">F1—B1—F2</td><td rowspan="1" colspan="1">109.73 (17)</td><td rowspan="1" colspan="1">N4—C12—C11</td><td rowspan="1" colspan="1">123.3 (2)</td></tr><tr><td rowspan="1" colspan="1">F4—B1—F2</td><td rowspan="1" colspan="1">110.22 (17)</td><td rowspan="1" colspan="1">N4—C12—H12</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">N2—C1—C2<sup>i</sup></td><td rowspan="1" colspan="1">119.49 (16)</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">118.4</td></tr><tr><td rowspan="1" colspan="1">N2—C1—S1</td><td rowspan="1" colspan="1">113.30 (13)</td><td rowspan="1" colspan="1">N2—Ni1—N2<sup>i</sup></td><td rowspan="1" colspan="1">180.00 (9)</td></tr><tr><td rowspan="1" colspan="1">C2<sup>i</sup>—C1—S1</td><td rowspan="1" colspan="1">127.21 (14)</td><td rowspan="1" colspan="1">N2—Ni1—O1<sup>i</sup></td><td rowspan="1" colspan="1">89.84 (6)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—C3</td><td rowspan="1" colspan="1">123.10 (16)</td><td rowspan="1" colspan="1">N2<sup>i</sup>—Ni1—O1<sup>i</sup></td><td rowspan="1" colspan="1">90.16 (6)</td></tr><tr><td rowspan="1" colspan="1">N1—C2—C1<sup>i</sup></td><td rowspan="1" colspan="1">113.09 (16)</td><td rowspan="1" colspan="1">N2—Ni1—O1</td><td rowspan="1" colspan="1">90.16 (6)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1<sup>i</sup></td><td rowspan="1" colspan="1">123.81 (16)</td><td rowspan="1" colspan="1">N2<sup>i</sup>—Ni1—O1</td><td rowspan="1" colspan="1">89.84 (6)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">118.89 (17)</td><td rowspan="1" colspan="1">O1<sup>i</sup>—Ni1—O1</td><td rowspan="1" colspan="1">180.00 (8)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">N2—Ni1—N1<sup>i</sup></td><td rowspan="1" colspan="1">79.22 (6)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">N2<sup>i</sup>—Ni1—N1<sup>i</sup></td><td rowspan="1" colspan="1">100.78 (6)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">118.81 (18)</td><td rowspan="1" colspan="1">O1<sup>i</sup>—Ni1—N1<sup>i</sup></td><td rowspan="1" colspan="1">90.02 (6)</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">O1—Ni1—N1<sup>i</sup></td><td rowspan="1" colspan="1">89.98 (6)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">N2—Ni1—N1</td><td rowspan="1" colspan="1">100.78 (6)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6</td><td rowspan="1" colspan="1">118.84 (17)</td><td rowspan="1" colspan="1">N2<sup>i</sup>—Ni1—N1</td><td rowspan="1" colspan="1">79.22 (6)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">O1<sup>i</sup>—Ni1—N1</td><td rowspan="1" colspan="1">89.98 (6)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">120.6</td><td rowspan="1" colspan="1">O1—Ni1—N1</td><td rowspan="1" colspan="1">90.02 (6)</td></tr><tr><td rowspan="1" colspan="1">N1—C6—C5</td><td rowspan="1" colspan="1">123.20 (17)</td><td rowspan="1" colspan="1">N1<sup>i</sup>—Ni1—N1</td><td rowspan="1" colspan="1">180.0</td></tr><tr><td rowspan="1" colspan="1">N1—C6—H6</td><td rowspan="1" colspan="1">118.4</td><td rowspan="1" colspan="1">C6—N1—C2</td><td rowspan="1" colspan="1">117.16 (16)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—H6</td><td rowspan="1" colspan="1">118.4</td><td rowspan="1" colspan="1">C6—N1—Ni1</td><td rowspan="1" colspan="1">128.93 (13)</td></tr><tr><td rowspan="1" colspan="1">N3—C7—C8</td><td rowspan="1" colspan="1">123.90 (17)</td><td rowspan="1" colspan="1">C2—N1—Ni1</td><td rowspan="1" colspan="1">113.82 (12)</td></tr><tr><td rowspan="1" colspan="1">N3—C7—S1</td><td rowspan="1" colspan="1">114.75 (13)</td><td rowspan="1" colspan="1">C1—N2—N3</td><td rowspan="1" colspan="1">114.22 (15)</td></tr><tr><td rowspan="1" colspan="1">C8—C7—S1</td><td rowspan="1" colspan="1">121.34 (14)</td><td rowspan="1" colspan="1">C1—N2—Ni1</td><td rowspan="1" colspan="1">114.28 (12)</td></tr><tr><td rowspan="1" colspan="1">N4—C8—C9</td><td rowspan="1" colspan="1">124.27 (17)</td><td rowspan="1" colspan="1">N3—N2—Ni1</td><td rowspan="1" colspan="1">131.42 (12)</td></tr><tr><td rowspan="1" colspan="1">N4—C8—C7</td><td rowspan="1" colspan="1">114.47 (16)</td><td rowspan="1" colspan="1">C7—N3—N2</td><td rowspan="1" colspan="1">110.73 (15)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C7</td><td rowspan="1" colspan="1">121.26 (17)</td><td rowspan="1" colspan="1">C12—N4—C8</td><td rowspan="1" colspan="1">116.68 (17)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10</td><td rowspan="1" colspan="1">117.7 (2)</td><td rowspan="1" colspan="1">Ni1—O1—H1W</td><td rowspan="1" colspan="1">123.4</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">121.2</td><td rowspan="1" colspan="1">Ni1—O1—H2W</td><td rowspan="1" colspan="1">131.6</td></tr><tr><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">121.2</td><td rowspan="1" colspan="1">H1W—O1—H2W</td><td rowspan="1" colspan="1">105.0</td></tr><tr><td rowspan="1" colspan="1">C11—C10—C9</td><td rowspan="1" colspan="1">119.2 (2)</td><td rowspan="1" colspan="1">C1—S1—C7</td><td rowspan="1" colspan="1">87.00 (9)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">120.4</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">N1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.5 (3)</td><td rowspan="1" colspan="1">C3—C2—N1—Ni1</td><td rowspan="1" colspan="1">176.49 (14)</td></tr><tr><td rowspan="1" colspan="1">C1<sup>i</sup>—C2—C3—C4</td><td rowspan="1" colspan="1">178.72 (17)</td><td rowspan="1" colspan="1">C1<sup>i</sup>—C2—N1—Ni1</td><td rowspan="1" colspan="1">−2.83 (19)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">0.7 (3)</td><td rowspan="1" colspan="1">C2<sup>i</sup>—C1—N2—N3</td><td rowspan="1" colspan="1">179.76 (15)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">−0.1 (3)</td><td rowspan="1" colspan="1">S1—C1—N2—N3</td><td rowspan="1" colspan="1">−0.4 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—N1</td><td rowspan="1" colspan="1">−0.7 (3)</td><td rowspan="1" colspan="1">C2<sup>i</sup>—C1—N2—Ni1</td><td rowspan="1" colspan="1">2.7 (2)</td></tr><tr><td rowspan="1" colspan="1">N3—C7—C8—N4</td><td rowspan="1" colspan="1">−160.31 (18)</td><td rowspan="1" colspan="1">S1—C1—N2—Ni1</td><td rowspan="1" colspan="1">−177.46 (8)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—C8—N4</td><td rowspan="1" colspan="1">20.7 (2)</td><td rowspan="1" colspan="1">C8—C7—N3—N2</td><td rowspan="1" colspan="1">−178.38 (16)</td></tr><tr><td rowspan="1" colspan="1">N3—C7—C8—C9</td><td rowspan="1" colspan="1">20.3 (3)</td><td rowspan="1" colspan="1">S1—C7—N3—N2</td><td rowspan="1" colspan="1">0.6 (2)</td></tr><tr><td rowspan="1" colspan="1">S1—C7—C8—C9</td><td rowspan="1" colspan="1">−158.62 (15)</td><td rowspan="1" colspan="1">C1—N2—N3—C7</td><td rowspan="1" colspan="1">−0.1 (2)</td></tr><tr><td rowspan="1" colspan="1">N4—C8—C9—C10</td><td rowspan="1" colspan="1">−0.3 (3)</td><td rowspan="1" colspan="1">Ni1—N2—N3—C7</td><td rowspan="1" colspan="1">176.26 (13)</td></tr><tr><td rowspan="1" colspan="1">C7—C8—C9—C10</td><td rowspan="1" colspan="1">179.01 (18)</td><td rowspan="1" colspan="1">C11—C12—N4—C8</td><td rowspan="1" colspan="1">1.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">0.3 (3)</td><td rowspan="1" colspan="1">C9—C8—N4—C12</td><td rowspan="1" colspan="1">−0.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">0.3 (3)</td><td rowspan="1" colspan="1">C7—C8—N4—C12</td><td rowspan="1" colspan="1">−179.74 (17)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12—N4</td><td rowspan="1" colspan="1">−1.0 (3)</td><td rowspan="1" colspan="1">N2—C1—S1—C7</td><td rowspan="1" colspan="1">0.63 (14)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—N1—C2</td><td rowspan="1" colspan="1">0.9 (3)</td><td rowspan="1" colspan="1">C2<sup>i</sup>—C1—S1—C7</td><td rowspan="1" colspan="1">−179.58 (17)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—N1—Ni1</td><td rowspan="1" colspan="1">−175.27 (14)</td><td rowspan="1" colspan="1">N3—C7—S1—C1</td><td rowspan="1" colspan="1">−0.72 (15)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—N1—C6</td><td rowspan="1" colspan="1">−0.2 (3)</td><td rowspan="1" colspan="1">C8—C7—S1—C1</td><td rowspan="1" colspan="1">178.31 (16)</td></tr><tr><td rowspan="1" colspan="1">C1<sup>i</sup>—C2—N1—C6</td><td rowspan="1" colspan="1">−179.56 (16)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+1, −<italic>y</italic>+2, −<italic>z</italic>.</p></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title><table-wrap position="anchor" id="d1e2462"><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—H1W···F1<sup>ii</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">1.88</td><td rowspan="1" colspan="1">2.704 (2)</td><td rowspan="1" colspan="1">160.</td></tr><tr><td rowspan="1" colspan="1">O1—H2W···F4</td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">1.94</td><td rowspan="1" colspan="1">2.7880 (19)</td><td rowspan="1" colspan="1">171.</td></tr></table></table-wrap><p>Symmetry codes: (ii) −<italic>x</italic>+3/2, <italic>y</italic>+1/2, −<italic>z</italic>+1/2.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Bentiss, F., Capet, F., Lagrenée, M., Saadi, M. & El Ammari, L. (2011). <italic>Acta Cryst.</italic> E<bold>67</bold>, m834–m835.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Bentiss, F., Lagrenée, M., Vezin, H., Wignacourt, J. P. & Holt, E. M. (2004). <italic>Polyhedron</italic>, <bold>23</bold>, 1903–1907.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Bentiss, F., Lagrenée, M., Wignacourt, J. P. & Holt, E. M. (2002). <italic>Polyhedron</italic>, <bold>21</bold>, 403–408.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Bruker (2005). <italic>APEX2</italic>, <italic>SAINT</italic> and <italic>SADABS</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Burnett, M. N. & Johnson, C. K. (1996). <italic>ORTEPIII</italic> Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Farrugia, L. J. (1997). <italic>J. Appl. Cryst.</italic>
<bold>30</bold>, 565.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Farrugia, L. J. (1999). <italic>J. Appl. Cryst.</italic>
<bold>32</bold>, 837–838.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Keij, F. S., de Graaff, R. A. G., Haasnoot, J. G. & Reedijk, J. (1984). <italic>J. Chem. Soc. Dalton Trans.</italic> pp. 2093–2097.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Lebrini, M., Bentiss, F. & Lagrenée, M. (2005). <italic>J. Heterocycl. Chem.</italic>
<bold>42</bold>, 991–994.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Zheng, X.-F., Wan, X.-S., Liu, W., Niu, C.-Y. & Kou, C.-H. (2006). <italic>Z. Kristallogr.</italic>
<bold>221</bold>, 543–544.</mixed-citation></ref></ref-list></back><floats-group><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (Å, °)</title></caption><table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th></tr></thead><tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1—H1<italic>W</italic>⋯F1<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.86</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.88</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.704 (2)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">160</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1—H2<italic>W</italic>⋯F4</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.86</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.94</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.7880 (19)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">171</td></tr></tbody></table><table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-67-m1052-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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