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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">(5,10,15,20-Tetraphenylporphyrinato-κ<sup>4</sup><italic>N</italic>)zinc–18-crown-6 (1/1)</title><author><name sortKey="Denden, Zouhour" sort="Denden, Zouhour" uniqKey="Denden Z" first="Zouhour" last="Denden">Zouhour Denden</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author><author><name sortKey="Bel Haj Hassen, Leila" sort="Bel Haj Hassen, Leila" uniqKey="Bel Haj Hassen L" first="Leila" last="Bel Haj Hassen">Leila Bel Haj Hassen</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author><author><name sortKey="Belkhiria, Mohamed Salah" sort="Belkhiria, Mohamed Salah" uniqKey="Belkhiria M" first="Mohamed Salah" last="Belkhiria">Mohamed Salah Belkhiria</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author><author><name sortKey="Daran, Jean Claude" sort="Daran, Jean Claude" uniqKey="Daran J" first="Jean-Claude" last="Daran">Jean-Claude Daran</name><affiliation><nlm:aff id="b">Laboratoire de Chimie de Coordination, CNRS UPR 8241, 205 route de Norbonne, 31077 Toulouse, Cedex 04,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Nasri, Habib" sort="Nasri, Habib" uniqKey="Nasri H" first="Habib" last="Nasri">Habib Nasri</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">24109272</idno><idno type="pmc">3793685</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793685</idno><idno type="RBID">PMC:3793685</idno><idno type="doi">10.1107/S1600536813018126</idno><date when="2013">2013</date><idno type="wicri:Area/Pmc/Corpus">000373</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000373</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">(5,10,15,20-Tetraphenylporphyrinato-κ<sup>4</sup><italic>N</italic>)zinc–18-crown-6 (1/1)</title><author><name sortKey="Denden, Zouhour" sort="Denden, Zouhour" uniqKey="Denden Z" first="Zouhour" last="Denden">Zouhour Denden</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author><author><name sortKey="Bel Haj Hassen, Leila" sort="Bel Haj Hassen, Leila" uniqKey="Bel Haj Hassen L" first="Leila" last="Bel Haj Hassen">Leila Bel Haj Hassen</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author><author><name sortKey="Belkhiria, Mohamed Salah" sort="Belkhiria, Mohamed Salah" uniqKey="Belkhiria M" first="Mohamed Salah" last="Belkhiria">Mohamed Salah Belkhiria</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author><author><name sortKey="Daran, Jean Claude" sort="Daran, Jean Claude" uniqKey="Daran J" first="Jean-Claude" last="Daran">Jean-Claude Daran</name><affiliation><nlm:aff id="b">Laboratoire de Chimie de Coordination, CNRS UPR 8241, 205 route de Norbonne, 31077 Toulouse, Cedex 04,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Nasri, Habib" sort="Nasri, Habib" uniqKey="Nasri H" first="Habib" last="Nasri">Habib Nasri</name><affiliation><nlm:aff id="a">Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title><idno type="eISSN">1600-5368</idno><imprint><date when="2013">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the title compound, [Zn(C<sub>44</sub>H<sub>28</sub>N<sub>4</sub>)]·C<sub>12</sub>H<sub>24</sub>O<sub>6</sub>, the Zn<sup>II</sup> ion lies on an inversion center and the asymmetric unit contains one half of a Zn(TPP) complex (TPP = 5,10,15,20-tetraphenylporphyrin dianion) and one half of a centrosymmetric 18-crown-6 molecule. The Zn(TPP) complex exhibits a nearly planar conformation of the porphyrin core [maximum deviation = 0.106 (2) Å] with an average Zn—N distance of 2.047 (2) Å. The title compound is considered as a one-dimensional polymer along [010], in which the Zn(TPP) moiety is linked to the closest O atoms of two symmetry-related 18-crown-6 molecules with a Zn—O distance of 2.582 (1) Å, completing a distorted octahedral coordination environment of the metal ion. The chains are mainly sustained by weak C—H⋯π interactions. An ethylene group of the 18-crown-6 molecule is disordered over three sites with occupancies of 0.50, 0.25 and 0.25.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title></journal-title-group><issn pub-type="epub">1600-5368</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">24109272</article-id><article-id pub-id-type="pmc">3793685</article-id><article-id pub-id-type="publisher-id">hy2633</article-id><article-id pub-id-type="doi">10.1107/S1600536813018126</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536813018126</article-id><article-categories><subj-group subj-group-type="heading"><subject>Metal-Organic Papers</subject></subj-group></article-categories><title-group><article-title>(5,10,15,20-Tetraphenylporphyrinato-κ<sup>4</sup><italic>N</italic>)zinc–18-crown-6 (1/1)</article-title><alt-title><italic>[Zn(C<sub>44</sub>H<sub>28</sub>N<sub>4</sub>)]·C<sub>12</sub>H<sub>24</sub>O<sub>6</sub></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Denden</surname><given-names>Zouhour</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Bel Haj Hassen</surname><given-names>Leila</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Belkhiria</surname><given-names>Mohamed Salah</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Daran</surname><given-names>Jean-Claude</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Nasri</surname><given-names>Habib</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Laboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l’environnement, 5019 Monastir,<country>Tunisia</country></aff><aff id="b"><label>b</label>Laboratoire de Chimie de Coordination, CNRS UPR 8241, 205 route de Norbonne, 31077 Toulouse, Cedex 04,<country>France</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>hnasri1@gmail.com</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>8</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>10</day><month>7</month><year>2013</year></pub-date><pub-date pub-type="pmc-release"><day>10</day><month>7</month><year>2013</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>69</volume><issue>Pt 8</issue><issue-id pub-id-type="publisher-id">e130800</issue-id><fpage>m444</fpage><lpage>m445</lpage><history><date date-type="received"><day>25</day><month>6</month><year>2013</year></date><date date-type="accepted"><day>01</day><month>7</month><year>2013</year></date></history><permissions><copyright-statement>© Denden et al. 2013</copyright-statement><copyright-year>2013</copyright-year><license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p></license></permissions><self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536813018126">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>In the title compound, [Zn(C<sub>44</sub>H<sub>28</sub>N<sub>4</sub>)]·C<sub>12</sub>H<sub>24</sub>O<sub>6</sub>, the Zn<sup>II</sup> ion lies on an inversion center and the asymmetric unit contains one half of a Zn(TPP) complex (TPP = 5,10,15,20-tetraphenylporphyrin dianion) and one half of a centrosymmetric 18-crown-6 molecule. The Zn(TPP) complex exhibits a nearly planar conformation of the porphyrin core [maximum deviation = 0.106 (2) Å] with an average Zn—N distance of 2.047 (2) Å. The title compound is considered as a one-dimensional polymer along [010], in which the Zn(TPP) moiety is linked to the closest O atoms of two symmetry-related 18-crown-6 molecules with a Zn—O distance of 2.582 (1) Å, completing a distorted octahedral coordination environment of the metal ion. The chains are mainly sustained by weak C—H⋯π interactions. An ethylene group of the 18-crown-6 molecule is disordered over three sites with occupancies of 0.50, 0.25 and 0.25.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature
</title><p>For related structures, see: Cheng & Scheidt (1995<xref ref-type="bibr" rid="bb4"> ▶</xref>); Diskin-Posner <italic>et al.</italic> (1999<xref ref-type="bibr" rid="bb5"> ▶</xref>); Ezzayani <italic>et al.</italic> (2013<xref ref-type="bibr" rid="bb6"> ▶</xref>); Kojima <italic>et al.</italic> (2009<xref ref-type="bibr" rid="bb9"> ▶</xref>); Kumar <italic>et al.</italic> (1997<xref ref-type="bibr" rid="bb10"> ▶</xref>); Mansour <italic>et al.</italic> (2010<xref ref-type="bibr" rid="bb11"> ▶</xref>); Ricard <italic>et al.</italic> (2001<xref ref-type="bibr" rid="bb15"> ▶</xref>); Suijkerbuijk <italic>et al.</italic> (2007<xref ref-type="bibr" rid="bb17"> ▶</xref>); Toumi <italic>et al.</italic> (2013<xref ref-type="bibr" rid="bb18"> ▶</xref>). For the SIMU/ISOR restraints used in the refinement, see: McArdle (1995<xref ref-type="bibr" rid="bb12"> ▶</xref>). For a description of the Cambridge Strcutural Database, see: Allen (2002<xref ref-type="bibr" rid="bb1"> ▶</xref>). For the synthesis, see: Oberda <italic>et al.</italic> (2011<xref ref-type="bibr" rid="bb13"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-69-0m444-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec id="sec2"><title>Experimental
</title><sec id="sec2.1"><title></title><sec id="sec2.1.1"><title>Crystal data
</title><p><list list-type="simple" id="l1"><list-item><p>[Zn(C<sub>44</sub>H<sub>28</sub>N<sub>4</sub>)]·C<sub>12</sub>H<sub>24</sub>O<sub>6</sub></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 942.39</p></list-item><list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-69-0m444-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 10.2170 (3) Å</p></list-item><list-item><p><italic>b</italic> = 11.1190 (4) Å</p></list-item><list-item><p><italic>c</italic> = 11.8243 (3) Å</p></list-item><list-item><p>α = 104.384 (3)°</p></list-item><list-item><p>β = 105.912 (3)°</p></list-item><list-item><p>γ = 108.096 (3)°</p></list-item><list-item><p><italic>V</italic> = 1143.23 (8) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 1</p></list-item><list-item><p>Mo <italic>K</italic>α radiation</p></list-item><list-item><p>μ = 0.60 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 180 K</p></list-item><list-item><p>0.48 × 0.45 × 0.33 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection
</title><p><list list-type="simple" id="l2"><list-item><p>Oxford Diffraction Xcalibur diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>CrysAlis RED</italic>; Oxford Diffraction, 2010<xref ref-type="bibr" rid="bb14"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.918, <italic>T</italic><sub>max</sub> = 1.000</p></list-item><list-item><p>22963 measured reflections</p></list-item><list-item><p>4503 independent reflections</p></list-item><list-item><p>3774 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.023</p></list-item></list></p></sec><sec id="sec2.1.3"><title>Refinement
</title><p><list list-type="simple" id="l3"><list-item><p><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.039</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.108</p></list-item><list-item><p><italic>S</italic> = 1.07</p></list-item><list-item><p>4503 reflections</p></list-item><list-item><p>310 parameters</p></list-item><list-item><p>30 restraints</p></list-item><list-item><p>H-atom parameters constrained</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.95 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.67 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e558"><title></title><p>Data collection: <italic>CrysAlis CCD</italic> (Oxford Diffraction, 2010<xref ref-type="bibr" rid="bb14"> ▶</xref>); cell refinement: <italic>CrysAlis RED</italic> (Oxford Diffraction, 2010<xref ref-type="bibr" rid="bb14"> ▶</xref>); data reduction: <italic>CrysAlis RED</italic>; program(s) used to solve structure: <italic>SIR2004</italic> (Burla <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb2"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb16"> ▶</xref>); molecular graphics: <italic>ORTEPIII</italic> (Burnett & Johnson, 1996<xref ref-type="bibr" rid="bb3"> ▶</xref>) and <italic>ORTEP-3 for Windows</italic> (Farrugia, 2012)<xref ref-type="bibr" rid="bb7"> ▶</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="loca-data"><p>Crystal structure: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536813018126/hy2633sup1.cif">10.1107/S1600536813018126/hy2633sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-69-0m444-sup1.cif" xlink:type="simple" id="d35e153" position="anchor"></media></supplementary-material><supplementary-material content-type="loca-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536813018126/hy2633Isup2.hkl">10.1107/S1600536813018126/hy2633Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-69-0m444-Isup2.hkl" xlink:type="simple" id="d35e160" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?hy2633&file=hy2633sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?hy2633sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hy2633&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><fn-group><fn id="fnu1"><p>Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsup?hy2633">HY2633</ext-link>).</p></fn></fn-group><ack><p>The authors gratefully acknowledge financial support from the Ministry of Higher Education and Scientific Research of Tunisia.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>In continuation of our research on the crystal structures of metalloporphyrins
resulting from the interactions of porphyrin complexes type [<italic>M</italic><sup>II</sup>(TPP)]
(TPP is a dianion of 5,10,15,20-tetraphenylporphyrin and <italic>M</italic> is a metal)
with 18-crown-6 (18-C-6), we recently reported the
molecular structures of three metalloporphyrines involving 18-C-6. The
first one is (tetraphenylporphyrinato)cobalt(II)-18-C-6 with the
formula [Co<sup>II</sup>(TPP)].(18-C-6) (Mansour <italic>et al.</italic>, 2010) and the
second
structure concerns the coordination complex
diaqua(tetraphenylporphyrinato)magnesium(II)-18-C-6 with the formula
[Mg(TPP)(H<sub>2</sub>O)<sub>2</sub>].(18-C-6) (Ezzayani <italic>et al.</italic>, 2013). The third
metalloporphyrin-18-C-6 derivative is the [Cd(TPP)(H<sub>2</sub>O)].(18-C-6)
species (Toumi <italic>et al.</italic>, 2013).
By the other hand a search of Cambridge Structural Database (CSD, version 5.34;
Allen, 2002) reveals only two zinc–porphyrin structures involving
18-C-6
molecules, with the same formula [Zn(TPP)(H<sub>2</sub>O)].(18-C-6)
[CSD refcodes: ZOLXUT (Cheng & Scheidt, 1995), and XIYGAN
(Diskin-Posner <italic>et al.</italic>, 1999)].
The average equatorial Zn—N distance equal to 2.071 (1) Å lies in the
range [2.035 (2)–2.081 (5) Å] of related porphyrin species, <italic>i.e.</italic>[Zn(TPP)(H<sub>2</sub>O)<sub>2</sub>] (Suijkerbuijk <italic>et al.</italic>, 2007) and
[Zn(TPP)(4-pyridinamine)] (Kojima <italic>et al.</italic>, 2009).
In order to gain more insight into the
interactions of 18-C-6 with zinc–porphyrin complexes, we report herein
the synthesis and crystal structure of the title compound,
[Zn(TPP)].(18-C-6).</p><p>In the title compound, two symmetry-related 18-C-6 molecules are weakly
bonded to the Zn<sup>II</sup> ion <italic>via</italic> the O1 atom with a distance of
2.582 (1) Å (Fig. 1). It is noteworthy that the Zn—O bond length values
for metalloporphyrin type [Zn(porph)(O<italic>R</italic>)]
(<italic>R</italic> = an alkyl or aryl group) are within the large range
[2.147 (5)–2.708 (2) Å] [CSD refcodes: BOQPIG (Ricard <italic>et al.</italic>,
2001),
and GETGER (Kumar <italic>et al.</italic>, 1997)]. Consequently,
we can consider that for the title compound, the 18-C-6 molecule is
weakly coordinated to the central metal.
We noticed the striking resemblance of the title compound and
the related compound [Co<sup>II</sup>(TPP)].(18-C-6): (i) the two structures are
isomorphs and they have the
space group <italic>P</italic>1 and the cell parameters are very close; (ii) the
Co—O(18-C-6) distance [2.533 (2) Å] is quite close to the value
of the title compound.
The porphyrin core presents a nearly planar conformation with
maximum and minimum deviations from the C<sub>20</sub>N<sub>4</sub> least-squares plane of 0.106
(2) and 0.000 (2) Å for C10 and C3 atoms, respectively, while the Zn<sup>II</sup>ion is at 0.05 (1) Å from the plane.</p><p>The crystal structure of the title compound resembles to one-dimensional
coordination polymer, where each [Zn(TPP)] moiety is linked to two
symmetry-related 18-C-6 molecules through the O1 and O1<sup>i</sup> atoms
(symmetry code: (i) 2-x, -y, 1-z) (Fig. 2). These chains are mainly
sustained by weak C—H···π interactions (Table 1).</p></sec><sec id="experimental"><title>Experimental </title><p>The reaction of the Zn(TPP) complex (15 mg, 0.022 mmol)
(Oberda <italic>et al.</italic>, 2011) with an excess of 18-C-6 (80 mg, 0.302 mmol)
in 15 ml of chlorobenzene at room temperature yielded after two hours
a red-purple solution. Crystals of the title compound were obtained
by diffusion of hexane into the chlorobenzene solution.</p></sec><sec id="refinement"><title>Refinement </title><p>All H atoms were placed in geometrically idealized positions and
refined as riding atoms, with C—H = 0.93 (aromatic) and 0.97 (CH<sub>2</sub>) Å
and with <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C).
An ethylene group of the 18-C-6 molecule is disordered
over three sites with occupancies of 0.50, 0.25 and 0.25. The anisotropic
ellipsoids of the atoms O3, C27A and C28A of the 18-C-6 molecule were
elongated, so the SIMU/ISOR restraints (McArdle, 1995) and EADP
constraint commands in the <italic>SHELXL97</italic> software (Sheldrick, 2008)
were used .</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. H atoms have been omitted for clarity. [Symmtry codes: (i) -x+2, -y, -z+1; (ii) -x+2, -y-1, -z+1.]</p></caption><graphic xlink:href="e-69-0m444-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>A drawing showing the one-dimensional structure of the title compound. H atoms have been omitted for clarity. [Symmetry code: (i) 2-x, -y, 1-z.]</p></caption><graphic xlink:href="e-69-0m444-fig2"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e236"><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">[Zn(C<sub>44</sub>H<sub>28</sub>N<sub>4</sub>)]·C<sub>12</sub>H<sub>24</sub>O<sub>6</sub></td><td rowspan="1" colspan="1"><italic>Z</italic> = 1</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 942.39</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 494</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.369 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 1</td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 10.2170 (3) Å</td><td rowspan="1" colspan="1">Cell parameters from 13909 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.1190 (4) Å</td><td rowspan="1" colspan="1">θ = 3.3–29.1°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 11.8243 (3) Å</td><td rowspan="1" colspan="1">µ = 0.60 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">α = 104.384 (3)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 180 K</td></tr><tr><td rowspan="1" colspan="1">β = 105.912 (3)°</td><td rowspan="1" colspan="1">Block, violet</td></tr><tr><td rowspan="1" colspan="1">γ = 108.096 (3)°</td><td rowspan="1" colspan="1">0.48 × 0.45 × 0.33 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1143.23 (8) Å<sup>3</sup></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e379"><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">Oxford Diffraction Xcalibur diffractometer</td><td rowspan="1" colspan="1">4503 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">3774 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> = 0.023</td></tr><tr><td rowspan="1" colspan="1">Detector resolution: 16.1978 pixels mm<sup>-1</sup></td><td rowspan="1" colspan="1">θ<sub>max</sub> = 26.0°, θ<sub>min</sub> = 3.3°</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1"><italic>h</italic> = −12→12</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>CrysAlis RED</italic>; Oxford Diffraction, 2010)</td><td rowspan="1" colspan="1"><italic>k</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.918, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>l</italic> = −14→14</td></tr><tr><td rowspan="1" colspan="1">22963 measured reflections</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e499"><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>)] = 0.039</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>) = 0.108</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.07</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0591<italic>P</italic>)<sup>2</sup> + 0.5621<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">4503 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">310 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.95 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">30 restraints</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.67 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="d1e657"><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="d1e756"><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">Occ. (<1)</td></tr><tr><td rowspan="1" colspan="1">Zn</td><td rowspan="1" colspan="1">1.0000</td><td rowspan="1" colspan="1">0.0000</td><td rowspan="1" colspan="1">0.5000</td><td rowspan="1" colspan="1">0.03274 (14)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">1.11054 (18)</td><td rowspan="1" colspan="1">−0.01373 (18)</td><td rowspan="1" colspan="1">0.66650 (15)</td><td rowspan="1" colspan="1">0.0230 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.79951 (17)</td><td rowspan="1" colspan="1">−0.10495 (17)</td><td rowspan="1" colspan="1">0.50470 (15)</td><td rowspan="1" colspan="1">0.0213 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">1.2617 (2)</td><td rowspan="1" colspan="1">0.0346 (2)</td><td rowspan="1" colspan="1">0.72913 (18)</td><td rowspan="1" colspan="1">0.0219 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">1.2919 (2)</td><td rowspan="1" colspan="1">−0.0065 (2)</td><td rowspan="1" colspan="1">0.83665 (19)</td><td rowspan="1" colspan="1">0.0248 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">1.3854</td><td rowspan="1" colspan="1">0.0140</td><td rowspan="1" colspan="1">0.8949</td><td rowspan="1" colspan="1">0.030*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">1.1598 (2)</td><td rowspan="1" colspan="1">−0.0801 (2)</td><td rowspan="1" colspan="1">0.83723 (18)</td><td rowspan="1" colspan="1">0.0243 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">1.1450</td><td rowspan="1" colspan="1">−0.1199</td><td rowspan="1" colspan="1">0.8958</td><td rowspan="1" colspan="1">0.029*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">1.0454 (2)</td><td rowspan="1" colspan="1">−0.0857 (2)</td><td rowspan="1" colspan="1">0.72994 (18)</td><td rowspan="1" colspan="1">0.0215 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.8921 (2)</td><td rowspan="1" colspan="1">−0.1589 (2)</td><td rowspan="1" colspan="1">0.69362 (18)</td><td rowspan="1" colspan="1">0.0214 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.7795 (2)</td><td rowspan="1" colspan="1">−0.1682 (2)</td><td rowspan="1" colspan="1">0.58835 (18)</td><td rowspan="1" colspan="1">0.0217 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.6231 (2)</td><td rowspan="1" colspan="1">−0.2468 (2)</td><td rowspan="1" colspan="1">0.5519 (2)</td><td rowspan="1" colspan="1">0.0274 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.5805</td><td rowspan="1" colspan="1">−0.2996</td><td rowspan="1" colspan="1">0.5927</td><td rowspan="1" colspan="1">0.033*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.5497 (2)</td><td rowspan="1" colspan="1">−0.2298 (2)</td><td rowspan="1" colspan="1">0.4477 (2)</td><td rowspan="1" colspan="1">0.0270 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">0.4471</td><td rowspan="1" colspan="1">−0.2677</td><td rowspan="1" colspan="1">0.4038</td><td rowspan="1" colspan="1">0.032*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.6606 (2)</td><td rowspan="1" colspan="1">−0.1415 (2)</td><td rowspan="1" colspan="1">0.41709 (18)</td><td rowspan="1" colspan="1">0.0215 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">1.3700 (2)</td><td rowspan="1" colspan="1">0.1076 (2)</td><td rowspan="1" colspan="1">0.69132 (18)</td><td rowspan="1" colspan="1">0.0221 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.8443 (2)</td><td rowspan="1" colspan="1">−0.2378 (2)</td><td rowspan="1" colspan="1">0.77232 (18)</td><td rowspan="1" colspan="1">0.0218 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.8211 (3)</td><td rowspan="1" colspan="1">−0.3733 (2)</td><td rowspan="1" colspan="1">0.7389 (2)</td><td rowspan="1" colspan="1">0.0355 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.8369</td><td rowspan="1" colspan="1">−0.4151</td><td rowspan="1" colspan="1">0.6684</td><td rowspan="1" colspan="1">0.043*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.7744 (3)</td><td rowspan="1" colspan="1">−0.4473 (2)</td><td rowspan="1" colspan="1">0.8098 (2)</td><td rowspan="1" colspan="1">0.0382 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.7593</td><td rowspan="1" colspan="1">−0.5383</td><td rowspan="1" colspan="1">0.7867</td><td rowspan="1" colspan="1">0.046*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.7504 (2)</td><td rowspan="1" colspan="1">−0.3870 (2)</td><td rowspan="1" colspan="1">0.9138 (2)</td><td rowspan="1" colspan="1">0.0318 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">0.7190</td><td rowspan="1" colspan="1">−0.4368</td><td rowspan="1" colspan="1">0.9611</td><td rowspan="1" colspan="1">0.038*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.7733 (3)</td><td rowspan="1" colspan="1">−0.2519 (2)</td><td rowspan="1" colspan="1">0.9478 (2)</td><td rowspan="1" colspan="1">0.0338 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.7569</td><td rowspan="1" colspan="1">−0.2105</td><td rowspan="1" colspan="1">1.0181</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.8207 (2)</td><td rowspan="1" colspan="1">−0.1776 (2)</td><td rowspan="1" colspan="1">0.8774 (2)</td><td rowspan="1" colspan="1">0.0288 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.8366</td><td rowspan="1" colspan="1">−0.0864</td><td rowspan="1" colspan="1">0.9013</td><td rowspan="1" colspan="1">0.035*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">1.5297 (2)</td><td rowspan="1" colspan="1">0.1524 (2)</td><td rowspan="1" colspan="1">0.77206 (18)</td><td rowspan="1" colspan="1">0.0228 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">1.6208 (2)</td><td rowspan="1" colspan="1">0.1016 (2)</td><td rowspan="1" colspan="1">0.7256 (2)</td><td rowspan="1" colspan="1">0.0303 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">1.5813</td><td rowspan="1" colspan="1">0.0383</td><td rowspan="1" colspan="1">0.6437</td><td rowspan="1" colspan="1">0.036*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">1.7692 (3)</td><td rowspan="1" colspan="1">0.1441 (3)</td><td rowspan="1" colspan="1">0.7995 (2)</td><td rowspan="1" colspan="1">0.0373 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">1.8287</td><td rowspan="1" colspan="1">0.1094</td><td rowspan="1" colspan="1">0.7672</td><td rowspan="1" colspan="1">0.045*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">1.8297 (2)</td><td rowspan="1" colspan="1">0.2382 (3)</td><td rowspan="1" colspan="1">0.9214 (2)</td><td rowspan="1" colspan="1">0.0366 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H20</td><td rowspan="1" colspan="1">1.9298</td><td rowspan="1" colspan="1">0.2674</td><td rowspan="1" colspan="1">0.9706</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">1.7406 (2)</td><td rowspan="1" colspan="1">0.2884 (2)</td><td rowspan="1" colspan="1">0.9696 (2)</td><td rowspan="1" colspan="1">0.0337 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H21</td><td rowspan="1" colspan="1">1.7805</td><td rowspan="1" colspan="1">0.3507</td><td rowspan="1" colspan="1">1.0519</td><td rowspan="1" colspan="1">0.040*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">1.59147 (13)</td><td rowspan="1" colspan="1">0.24577 (12)</td><td rowspan="1" colspan="1">0.89529 (11)</td><td rowspan="1" colspan="1">0.0270 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H22</td><td rowspan="1" colspan="1">1.5321</td><td rowspan="1" colspan="1">0.2801</td><td rowspan="1" colspan="1">0.9283</td><td rowspan="1" colspan="1">0.032*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.99283 (13)</td><td rowspan="1" colspan="1">−0.23197 (12)</td><td rowspan="1" colspan="1">0.38069 (11)</td><td rowspan="1" colspan="1">0.0414 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.88485 (13)</td><td rowspan="1" colspan="1">−0.30609 (12)</td><td rowspan="1" colspan="1">0.25589 (11)</td><td rowspan="1" colspan="1">0.0415 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H23A</td><td rowspan="1" colspan="1">0.9247</td><td rowspan="1" colspan="1">−0.3582</td><td rowspan="1" colspan="1">0.2072</td><td rowspan="1" colspan="1">0.050*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H23B</td><td rowspan="1" colspan="1">0.8669</td><td rowspan="1" colspan="1">−0.2424</td><td rowspan="1" colspan="1">0.2171</td><td rowspan="1" colspan="1">0.050*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C24</td><td rowspan="1" colspan="1">0.7397 (3)</td><td rowspan="1" colspan="1">−0.4009 (3)</td><td rowspan="1" colspan="1">0.2491 (2)</td><td rowspan="1" colspan="1">0.0423 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H24A</td><td rowspan="1" colspan="1">0.7125</td><td rowspan="1" colspan="1">−0.3563</td><td rowspan="1" colspan="1">0.3149</td><td rowspan="1" colspan="1">0.051*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H24B</td><td rowspan="1" colspan="1">0.6622</td><td rowspan="1" colspan="1">−0.4252</td><td rowspan="1" colspan="1">0.1681</td><td rowspan="1" colspan="1">0.051*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.7523 (2)</td><td rowspan="1" colspan="1">−0.51824 (18)</td><td rowspan="1" colspan="1">0.26441 (18)</td><td rowspan="1" colspan="1">0.0450 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.6304 (3)</td><td rowspan="1" colspan="1">−0.6046 (3)</td><td rowspan="1" colspan="1">0.2816 (3)</td><td rowspan="1" colspan="1">0.0473 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25A</td><td rowspan="1" colspan="1">0.5470</td><td rowspan="1" colspan="1">−0.6566</td><td rowspan="1" colspan="1">0.2012</td><td rowspan="1" colspan="1">0.057*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25B</td><td rowspan="1" colspan="1">0.5991</td><td rowspan="1" colspan="1">−0.5509</td><td rowspan="1" colspan="1">0.3380</td><td rowspan="1" colspan="1">0.057*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C26</td><td rowspan="1" colspan="1">0.6787 (3)</td><td rowspan="1" colspan="1">−0.6981 (3)</td><td rowspan="1" colspan="1">0.3367 (3)</td><td rowspan="1" colspan="1">0.0510 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H26A</td><td rowspan="1" colspan="1">0.5923</td><td rowspan="1" colspan="1">−0.7734</td><td rowspan="1" colspan="1">0.3282</td><td rowspan="1" colspan="1">0.061*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H26B</td><td rowspan="1" colspan="1">0.7329</td><td rowspan="1" colspan="1">−0.7344</td><td rowspan="1" colspan="1">0.2921</td><td rowspan="1" colspan="1">0.061*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.7692 (2)</td><td rowspan="1" colspan="1">−0.6263 (2)</td><td rowspan="1" colspan="1">0.4630 (2)</td><td rowspan="1" colspan="1">0.0602 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C27A</td><td rowspan="1" colspan="1">0.9180 (7)</td><td rowspan="1" colspan="1">−0.6327 (7)</td><td rowspan="1" colspan="1">0.5200 (6)</td><td rowspan="1" colspan="1">0.0541 (7)</td><td rowspan="1" colspan="1">0.50</td></tr><tr><td rowspan="1" colspan="1">H27A</td><td rowspan="1" colspan="1">0.9569</td><td rowspan="1" colspan="1">−0.6576</td><td rowspan="1" colspan="1">0.4558</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1">0.50</td></tr><tr><td rowspan="1" colspan="1">H27B</td><td rowspan="1" colspan="1">0.9902</td><td rowspan="1" colspan="1">−0.5461</td><td rowspan="1" colspan="1">0.5848</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1">0.50</td></tr><tr><td rowspan="1" colspan="1">C28A</td><td rowspan="1" colspan="1">0.8820 (7)</td><td rowspan="1" colspan="1">−0.7408 (7)</td><td rowspan="1" colspan="1">0.5755 (6)</td><td rowspan="1" colspan="1">0.0492 (8)</td><td rowspan="1" colspan="1">0.50</td></tr><tr><td rowspan="1" colspan="1">H28A</td><td rowspan="1" colspan="1">0.8521</td><td rowspan="1" colspan="1">−0.7103</td><td rowspan="1" colspan="1">0.6447</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1">0.50</td></tr><tr><td rowspan="1" colspan="1">H28B</td><td rowspan="1" colspan="1">0.7999</td><td rowspan="1" colspan="1">−0.8229</td><td rowspan="1" colspan="1">0.5118</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1">0.50</td></tr><tr><td rowspan="1" colspan="1">C27B</td><td rowspan="1" colspan="1">0.8033 (15)</td><td rowspan="1" colspan="1">−0.7226 (13)</td><td rowspan="1" colspan="1">0.5251 (14)</td><td rowspan="1" colspan="1">0.0541 (7)</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H27C</td><td rowspan="1" colspan="1">0.7839</td><td rowspan="1" colspan="1">−0.7096</td><td rowspan="1" colspan="1">0.6022</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H27D</td><td rowspan="1" colspan="1">0.7453</td><td rowspan="1" colspan="1">−0.8165</td><td rowspan="1" colspan="1">0.4685</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">C28B</td><td rowspan="1" colspan="1">0.9557 (13)</td><td rowspan="1" colspan="1">−0.6854 (13)</td><td rowspan="1" colspan="1">0.5508 (13)</td><td rowspan="1" colspan="1">0.0492 (8)</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H28C</td><td rowspan="1" colspan="1">1.0109</td><td rowspan="1" colspan="1">−0.5895</td><td rowspan="1" colspan="1">0.6021</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H28D</td><td rowspan="1" colspan="1">0.9724</td><td rowspan="1" colspan="1">−0.7018</td><td rowspan="1" colspan="1">0.4725</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">C27C</td><td rowspan="1" colspan="1">0.8191 (15)</td><td rowspan="1" colspan="1">−0.7395 (13)</td><td rowspan="1" colspan="1">0.4715 (13)</td><td rowspan="1" colspan="1">0.0541 (7)</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H27E</td><td rowspan="1" colspan="1">0.7387</td><td rowspan="1" colspan="1">−0.8215</td><td rowspan="1" colspan="1">0.4604</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H27F</td><td rowspan="1" colspan="1">0.8663</td><td rowspan="1" colspan="1">−0.7600</td><td rowspan="1" colspan="1">0.4127</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">C28C</td><td rowspan="1" colspan="1">0.9287 (15)</td><td rowspan="1" colspan="1">−0.6667 (14)</td><td rowspan="1" colspan="1">0.6059 (12)</td><td rowspan="1" colspan="1">0.0492 (8)</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H28E</td><td rowspan="1" colspan="1">0.8790</td><td rowspan="1" colspan="1">−0.6567</td><td rowspan="1" colspan="1">0.6645</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1">0.25</td></tr><tr><td rowspan="1" colspan="1">H28F</td><td rowspan="1" colspan="1">0.9991</td><td rowspan="1" colspan="1">−0.5779</td><td rowspan="1" colspan="1">0.6184</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1">0.25</td></tr></table></table-wrap></sec><sec id="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e1796"><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">Zn</td><td rowspan="1" colspan="1">0.01801 (19)</td><td rowspan="1" colspan="1">0.0560 (3)</td><td rowspan="1" colspan="1">0.0266 (2)</td><td rowspan="1" colspan="1">0.00947 (17)</td><td rowspan="1" colspan="1">0.00743 (14)</td><td rowspan="1" colspan="1">0.02734 (18)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0178 (8)</td><td rowspan="1" colspan="1">0.0310 (9)</td><td rowspan="1" colspan="1">0.0204 (8)</td><td rowspan="1" colspan="1">0.0074 (7)</td><td rowspan="1" colspan="1">0.0065 (7)</td><td rowspan="1" colspan="1">0.0138 (7)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0182 (8)</td><td rowspan="1" colspan="1">0.0277 (9)</td><td rowspan="1" colspan="1">0.0180 (8)</td><td rowspan="1" colspan="1">0.0078 (7)</td><td rowspan="1" colspan="1">0.0058 (6)</td><td rowspan="1" colspan="1">0.0116 (7)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0206 (9)</td><td rowspan="1" colspan="1">0.0250 (10)</td><td rowspan="1" colspan="1">0.0183 (9)</td><td rowspan="1" colspan="1">0.0085 (8)</td><td rowspan="1" colspan="1">0.0049 (8)</td><td rowspan="1" colspan="1">0.0089 (8)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0232 (10)</td><td rowspan="1" colspan="1">0.0294 (11)</td><td rowspan="1" colspan="1">0.0200 (10)</td><td rowspan="1" colspan="1">0.0106 (9)</td><td rowspan="1" colspan="1">0.0040 (8)</td><td rowspan="1" colspan="1">0.0110 (8)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0257 (10)</td><td rowspan="1" colspan="1">0.0285 (11)</td><td rowspan="1" colspan="1">0.0191 (9)</td><td rowspan="1" colspan="1">0.0102 (9)</td><td rowspan="1" colspan="1">0.0066 (8)</td><td rowspan="1" colspan="1">0.0125 (8)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0234 (10)</td><td rowspan="1" colspan="1">0.0252 (10)</td><td rowspan="1" colspan="1">0.0176 (9)</td><td rowspan="1" colspan="1">0.0098 (8)</td><td rowspan="1" colspan="1">0.0080 (8)</td><td rowspan="1" colspan="1">0.0103 (8)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0249 (10)</td><td rowspan="1" colspan="1">0.0227 (10)</td><td rowspan="1" colspan="1">0.0185 (9)</td><td rowspan="1" colspan="1">0.0091 (8)</td><td rowspan="1" colspan="1">0.0105 (8)</td><td rowspan="1" colspan="1">0.0091 (8)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0217 (10)</td><td rowspan="1" colspan="1">0.0245 (10)</td><td rowspan="1" colspan="1">0.0198 (9)</td><td rowspan="1" colspan="1">0.0076 (8)</td><td rowspan="1" colspan="1">0.0101 (8)</td><td rowspan="1" colspan="1">0.0096 (8)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0226 (10)</td><td rowspan="1" colspan="1">0.0338 (12)</td><td rowspan="1" colspan="1">0.0268 (11)</td><td rowspan="1" colspan="1">0.0072 (9)</td><td rowspan="1" colspan="1">0.0112 (9)</td><td rowspan="1" colspan="1">0.0158 (9)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0188 (10)</td><td rowspan="1" colspan="1">0.0318 (11)</td><td rowspan="1" colspan="1">0.0272 (11)</td><td rowspan="1" colspan="1">0.0057 (9)</td><td rowspan="1" colspan="1">0.0078 (8)</td><td rowspan="1" colspan="1">0.0127 (9)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0184 (9)</td><td rowspan="1" colspan="1">0.0255 (10)</td><td rowspan="1" colspan="1">0.0198 (9)</td><td rowspan="1" colspan="1">0.0077 (8)</td><td rowspan="1" colspan="1">0.0070 (8)</td><td rowspan="1" colspan="1">0.0091 (8)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0199 (9)</td><td rowspan="1" colspan="1">0.0244 (10)</td><td rowspan="1" colspan="1">0.0201 (9)</td><td rowspan="1" colspan="1">0.0088 (8)</td><td rowspan="1" colspan="1">0.0054 (8)</td><td rowspan="1" colspan="1">0.0082 (8)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0181 (9)</td><td rowspan="1" colspan="1">0.0258 (10)</td><td rowspan="1" colspan="1">0.0194 (9)</td><td rowspan="1" colspan="1">0.0054 (8)</td><td rowspan="1" colspan="1">0.0055 (8)</td><td rowspan="1" colspan="1">0.0113 (8)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0522 (15)</td><td rowspan="1" colspan="1">0.0290 (12)</td><td rowspan="1" colspan="1">0.0245 (11)</td><td rowspan="1" colspan="1">0.0139 (11)</td><td rowspan="1" colspan="1">0.0175 (10)</td><td rowspan="1" colspan="1">0.0089 (9)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0504 (15)</td><td rowspan="1" colspan="1">0.0233 (11)</td><td rowspan="1" colspan="1">0.0313 (12)</td><td rowspan="1" colspan="1">0.0065 (11)</td><td rowspan="1" colspan="1">0.0106 (11)</td><td rowspan="1" colspan="1">0.0109 (10)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0276 (11)</td><td rowspan="1" colspan="1">0.0368 (13)</td><td rowspan="1" colspan="1">0.0288 (11)</td><td rowspan="1" colspan="1">0.0050 (10)</td><td rowspan="1" colspan="1">0.0084 (9)</td><td rowspan="1" colspan="1">0.0213 (10)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0431 (13)</td><td rowspan="1" colspan="1">0.0442 (14)</td><td rowspan="1" colspan="1">0.0296 (11)</td><td rowspan="1" colspan="1">0.0230 (11)</td><td rowspan="1" colspan="1">0.0229 (10)</td><td rowspan="1" colspan="1">0.0214 (10)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0379 (12)</td><td rowspan="1" colspan="1">0.0288 (11)</td><td rowspan="1" colspan="1">0.0281 (11)</td><td rowspan="1" colspan="1">0.0163 (10)</td><td rowspan="1" colspan="1">0.0170 (9)</td><td rowspan="1" colspan="1">0.0152 (9)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0202 (10)</td><td rowspan="1" colspan="1">0.0256 (10)</td><td rowspan="1" colspan="1">0.0225 (10)</td><td rowspan="1" colspan="1">0.0072 (8)</td><td rowspan="1" colspan="1">0.0060 (8)</td><td rowspan="1" colspan="1">0.0137 (8)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0275 (11)</td><td rowspan="1" colspan="1">0.0339 (12)</td><td rowspan="1" colspan="1">0.0295 (11)</td><td rowspan="1" colspan="1">0.0125 (10)</td><td rowspan="1" colspan="1">0.0107 (9)</td><td rowspan="1" colspan="1">0.0116 (9)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.0259 (11)</td><td rowspan="1" colspan="1">0.0465 (14)</td><td rowspan="1" colspan="1">0.0495 (14)</td><td rowspan="1" colspan="1">0.0193 (11)</td><td rowspan="1" colspan="1">0.0167 (11)</td><td rowspan="1" colspan="1">0.0254 (12)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.0182 (10)</td><td rowspan="1" colspan="1">0.0450 (14)</td><td rowspan="1" colspan="1">0.0424 (13)</td><td rowspan="1" colspan="1">0.0069 (10)</td><td rowspan="1" colspan="1">0.0018 (9)</td><td rowspan="1" colspan="1">0.0274 (11)</td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.0298 (12)</td><td rowspan="1" colspan="1">0.0333 (12)</td><td rowspan="1" colspan="1">0.0255 (11)</td><td rowspan="1" colspan="1">0.0041 (10)</td><td rowspan="1" colspan="1">0.0001 (9)</td><td rowspan="1" colspan="1">0.0134 (9)</td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.0256 (10)</td><td rowspan="1" colspan="1">0.0277 (11)</td><td rowspan="1" colspan="1">0.0254 (10)</td><td rowspan="1" colspan="1">0.0092 (9)</td><td rowspan="1" colspan="1">0.0071 (8)</td><td rowspan="1" colspan="1">0.0110 (9)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0372 (9)</td><td rowspan="1" colspan="1">0.0465 (10)</td><td rowspan="1" colspan="1">0.0370 (9)</td><td rowspan="1" colspan="1">0.0164 (8)</td><td rowspan="1" colspan="1">0.0067 (7)</td><td rowspan="1" colspan="1">0.0185 (8)</td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.0559 (16)</td><td rowspan="1" colspan="1">0.0368 (13)</td><td rowspan="1" colspan="1">0.0301 (12)</td><td rowspan="1" colspan="1">0.0170 (12)</td><td rowspan="1" colspan="1">0.0140 (11)</td><td rowspan="1" colspan="1">0.0145 (10)</td></tr><tr><td rowspan="1" colspan="1">C24</td><td rowspan="1" colspan="1">0.0449 (14)</td><td rowspan="1" colspan="1">0.0412 (14)</td><td rowspan="1" colspan="1">0.0350 (13)</td><td rowspan="1" colspan="1">0.0208 (12)</td><td rowspan="1" colspan="1">0.0062 (11)</td><td rowspan="1" colspan="1">0.0106 (11)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0465 (10)</td><td rowspan="1" colspan="1">0.0412 (10)</td><td rowspan="1" colspan="1">0.0627 (12)</td><td rowspan="1" colspan="1">0.0218 (9)</td><td rowspan="1" colspan="1">0.0329 (9)</td><td rowspan="1" colspan="1">0.0252 (9)</td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.0296 (12)</td><td rowspan="1" colspan="1">0.0583 (17)</td><td rowspan="1" colspan="1">0.0482 (15)</td><td rowspan="1" colspan="1">0.0101 (12)</td><td rowspan="1" colspan="1">0.0137 (11)</td><td rowspan="1" colspan="1">0.0212 (13)</td></tr><tr><td rowspan="1" colspan="1">C26</td><td rowspan="1" colspan="1">0.0595 (18)</td><td rowspan="1" colspan="1">0.0364 (14)</td><td rowspan="1" colspan="1">0.0672 (19)</td><td rowspan="1" colspan="1">0.0201 (13)</td><td rowspan="1" colspan="1">0.0383 (16)</td><td rowspan="1" colspan="1">0.0188 (13)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0635 (8)</td><td rowspan="1" colspan="1">0.0611 (8)</td><td rowspan="1" colspan="1">0.0590 (8)</td><td rowspan="1" colspan="1">0.0356 (6)</td><td rowspan="1" colspan="1">0.0160 (6)</td><td rowspan="1" colspan="1">0.0219 (6)</td></tr><tr><td rowspan="1" colspan="1">C27A</td><td rowspan="1" colspan="1">0.0561 (9)</td><td rowspan="1" colspan="1">0.0546 (9)</td><td rowspan="1" colspan="1">0.0546 (9)</td><td rowspan="1" colspan="1">0.0271 (7)</td><td rowspan="1" colspan="1">0.0179 (7)</td><td rowspan="1" colspan="1">0.0225 (7)</td></tr><tr><td rowspan="1" colspan="1">C28A</td><td rowspan="1" colspan="1">0.0508 (10)</td><td rowspan="1" colspan="1">0.0514 (10)</td><td rowspan="1" colspan="1">0.0503 (10)</td><td rowspan="1" colspan="1">0.0242 (8)</td><td rowspan="1" colspan="1">0.0202 (7)</td><td rowspan="1" colspan="1">0.0213 (8)</td></tr><tr><td rowspan="1" colspan="1">C27B</td><td rowspan="1" colspan="1">0.0561 (9)</td><td rowspan="1" colspan="1">0.0546 (9)</td><td rowspan="1" colspan="1">0.0546 (9)</td><td rowspan="1" colspan="1">0.0271 (7)</td><td rowspan="1" colspan="1">0.0179 (7)</td><td rowspan="1" colspan="1">0.0225 (7)</td></tr><tr><td rowspan="1" colspan="1">C28B</td><td rowspan="1" colspan="1">0.0508 (10)</td><td rowspan="1" colspan="1">0.0514 (10)</td><td rowspan="1" colspan="1">0.0503 (10)</td><td rowspan="1" colspan="1">0.0242 (8)</td><td rowspan="1" colspan="1">0.0202 (7)</td><td rowspan="1" colspan="1">0.0213 (8)</td></tr><tr><td rowspan="1" colspan="1">C27C</td><td rowspan="1" colspan="1">0.0561 (9)</td><td rowspan="1" colspan="1">0.0546 (9)</td><td rowspan="1" colspan="1">0.0546 (9)</td><td rowspan="1" colspan="1">0.0271 (7)</td><td rowspan="1" colspan="1">0.0179 (7)</td><td rowspan="1" colspan="1">0.0225 (7)</td></tr><tr><td rowspan="1" colspan="1">C28C</td><td rowspan="1" colspan="1">0.0508 (10)</td><td rowspan="1" colspan="1">0.0514 (10)</td><td rowspan="1" colspan="1">0.0503 (10)</td><td rowspan="1" colspan="1">0.0242 (8)</td><td rowspan="1" colspan="1">0.0202 (7)</td><td rowspan="1" colspan="1">0.0213 (8)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e2413"><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">Zn—N2</td><td rowspan="1" colspan="1">2.0421 (16)</td><td rowspan="1" colspan="1">C21—C22</td><td rowspan="1" colspan="1">1.389 (2)</td></tr><tr><td rowspan="1" colspan="1">Zn—N1</td><td rowspan="1" colspan="1">2.0524 (16)</td><td rowspan="1" colspan="1">C21—H21</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.372 (2)</td><td rowspan="1" colspan="1">C22—H22</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C4</td><td rowspan="1" colspan="1">1.374 (2)</td><td rowspan="1" colspan="1">O1—C28A<sup>ii</sup></td><td rowspan="1" colspan="1">1.397 (6)</td></tr><tr><td rowspan="1" colspan="1">N2—C9</td><td rowspan="1" colspan="1">1.371 (2)</td><td rowspan="1" colspan="1">O1—C23</td><td rowspan="1" colspan="1">1.4185</td></tr><tr><td rowspan="1" colspan="1">N2—C6</td><td rowspan="1" colspan="1">1.372 (2)</td><td rowspan="1" colspan="1">O1—C28B<sup>ii</sup></td><td rowspan="1" colspan="1">1.487 (13)</td></tr><tr><td rowspan="1" colspan="1">C1—C10</td><td rowspan="1" colspan="1">1.405 (3)</td><td rowspan="1" colspan="1">O1—C28C<sup>ii</sup></td><td rowspan="1" colspan="1">1.587 (12)</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.443 (3)</td><td rowspan="1" colspan="1">C23—C24</td><td rowspan="1" colspan="1">1.496 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.347 (3)</td><td rowspan="1" colspan="1">C23—H23A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C23—H23B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.443 (3)</td><td rowspan="1" colspan="1">C24—O2</td><td rowspan="1" colspan="1">1.400 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C24—H24A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.402 (3)</td><td rowspan="1" colspan="1">C24—H24B</td><td rowspan="1" colspan="1">0.9700</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">O2—C25</td><td rowspan="1" colspan="1">1.417 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C11</td><td rowspan="1" colspan="1">1.504 (3)</td><td rowspan="1" colspan="1">C25—C26</td><td rowspan="1" colspan="1">1.492 (4)</td></tr><tr><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.439 (3)</td><td rowspan="1" colspan="1">C25—H25A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.346 (3)</td><td rowspan="1" colspan="1">C25—H25B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C7—H7</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C26—O3</td><td rowspan="1" colspan="1">1.384 (4)</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.445 (3)</td><td rowspan="1" colspan="1">C26—H26A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C26—H26B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C9—C10<sup>i</sup></td><td rowspan="1" colspan="1">1.406 (3)</td><td rowspan="1" colspan="1">O3—C27C</td><td rowspan="1" colspan="1">1.513 (12)</td></tr><tr><td rowspan="1" colspan="1">C10—C9<sup>i</sup></td><td rowspan="1" colspan="1">1.406 (3)</td><td rowspan="1" colspan="1">O3—C27B</td><td rowspan="1" colspan="1">1.513 (13)</td></tr><tr><td rowspan="1" colspan="1">C10—C17</td><td rowspan="1" colspan="1">1.493 (3)</td><td rowspan="1" colspan="1">O3—C27A</td><td rowspan="1" colspan="1">1.517 (6)</td></tr><tr><td rowspan="1" colspan="1">C11—C16</td><td rowspan="1" colspan="1">1.379 (3)</td><td rowspan="1" colspan="1">C27A—C28A</td><td rowspan="1" colspan="1">1.504 (9)</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.384 (3)</td><td rowspan="1" colspan="1">C27A—H27A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.388 (3)</td><td rowspan="1" colspan="1">C27A—H27B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C28A—O1<sup>ii</sup></td><td rowspan="1" colspan="1">1.397 (6)</td></tr><tr><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.370 (3)</td><td rowspan="1" colspan="1">C28A—H28A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C28A—H28B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.380 (3)</td><td rowspan="1" colspan="1">C27B—C28B</td><td rowspan="1" colspan="1">1.403 (18)</td></tr><tr><td rowspan="1" colspan="1">C14—H14</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C27B—H27C</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.386 (3)</td><td rowspan="1" colspan="1">C27B—H27D</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C28B—O1<sup>ii</sup></td><td rowspan="1" colspan="1">1.487 (12)</td></tr><tr><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C28B—H28C</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C17—C22</td><td rowspan="1" colspan="1">1.392 (2)</td><td rowspan="1" colspan="1">C28B—H28D</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C17—C18</td><td rowspan="1" colspan="1">1.393 (3)</td><td rowspan="1" colspan="1">C27C—C28C</td><td rowspan="1" colspan="1">1.502 (18)</td></tr><tr><td rowspan="1" colspan="1">C18—C19</td><td rowspan="1" colspan="1">1.382 (3)</td><td rowspan="1" colspan="1">C27C—H27E</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C27C—H27F</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C19—C20</td><td rowspan="1" colspan="1">1.383 (4)</td><td rowspan="1" colspan="1">C28C—O1<sup>ii</sup></td><td rowspan="1" colspan="1">1.587 (12)</td></tr><tr><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C28C—H28E</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C20—C21</td><td rowspan="1" colspan="1">1.381 (4)</td><td rowspan="1" colspan="1">C28C—H28F</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C20—H20</td><td rowspan="1" colspan="1">0.9300</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">N2—Zn—N2<sup>i</sup></td><td rowspan="1" colspan="1">180.0</td><td rowspan="1" colspan="1">C20—C21—H21</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">N2—Zn—N1<sup>i</sup></td><td rowspan="1" colspan="1">89.28 (6)</td><td rowspan="1" colspan="1">C22—C21—H21</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">N2<sup>i</sup>—Zn—N1<sup>i</sup></td><td rowspan="1" colspan="1">90.72 (6)</td><td rowspan="1" colspan="1">C21—C22—C17</td><td rowspan="1" colspan="1">120.83 (16)</td></tr><tr><td rowspan="1" colspan="1">N2—Zn—N1</td><td rowspan="1" colspan="1">90.72 (6)</td><td rowspan="1" colspan="1">C21—C22—H22</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">N2<sup>i</sup>—Zn—N1</td><td rowspan="1" colspan="1">89.28 (6)</td><td rowspan="1" colspan="1">C17—C22—H22</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">N1<sup>i</sup>—Zn—N1</td><td rowspan="1" colspan="1">180.0</td><td rowspan="1" colspan="1">C28A<sup>ii</sup>—O1—C23</td><td rowspan="1" colspan="1">121.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—C4</td><td rowspan="1" colspan="1">106.75 (16)</td><td rowspan="1" colspan="1">C23—O1—C28B<sup>ii</sup></td><td rowspan="1" colspan="1">115.6 (5)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—Zn</td><td rowspan="1" colspan="1">127.32 (13)</td><td rowspan="1" colspan="1">C23—O1—C28C<sup>ii</sup></td><td rowspan="1" colspan="1">99.7 (5)</td></tr><tr><td rowspan="1" colspan="1">C4—N1—Zn</td><td rowspan="1" colspan="1">125.65 (13)</td><td rowspan="1" colspan="1">O1—C23—C24</td><td rowspan="1" colspan="1">113.75 (11)</td></tr><tr><td rowspan="1" colspan="1">C9—N2—C6</td><td rowspan="1" colspan="1">106.67 (16)</td><td rowspan="1" colspan="1">O1—C23—H23A</td><td rowspan="1" colspan="1">108.8</td></tr><tr><td rowspan="1" colspan="1">C9—N2—Zn</td><td rowspan="1" colspan="1">127.28 (13)</td><td rowspan="1" colspan="1">C24—C23—H23A</td><td rowspan="1" colspan="1">108.8</td></tr><tr><td rowspan="1" colspan="1">C6—N2—Zn</td><td rowspan="1" colspan="1">125.51 (13)</td><td rowspan="1" colspan="1">O1—C23—H23B</td><td rowspan="1" colspan="1">108.8</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C10</td><td rowspan="1" colspan="1">125.32 (18)</td><td rowspan="1" colspan="1">C24—C23—H23B</td><td rowspan="1" colspan="1">108.8</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">109.25 (17)</td><td rowspan="1" colspan="1">H23A—C23—H23B</td><td rowspan="1" colspan="1">107.7</td></tr><tr><td rowspan="1" colspan="1">C10—C1—C2</td><td rowspan="1" colspan="1">125.37 (18)</td><td rowspan="1" colspan="1">O2—C24—C23</td><td rowspan="1" colspan="1">109.77 (19)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">107.45 (17)</td><td rowspan="1" colspan="1">O2—C24—H24A</td><td rowspan="1" colspan="1">109.7</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">126.3</td><td rowspan="1" colspan="1">C23—C24—H24A</td><td rowspan="1" colspan="1">109.7</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">126.3</td><td rowspan="1" colspan="1">O2—C24—H24B</td><td rowspan="1" colspan="1">109.7</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">107.10 (17)</td><td rowspan="1" colspan="1">C23—C24—H24B</td><td rowspan="1" colspan="1">109.7</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">126.5</td><td rowspan="1" colspan="1">H24A—C24—H24B</td><td rowspan="1" colspan="1">108.2</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">126.5</td><td rowspan="1" colspan="1">C24—O2—C25</td><td rowspan="1" colspan="1">114.6 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—C4—C5</td><td rowspan="1" colspan="1">125.70 (17)</td><td rowspan="1" colspan="1">O2—C25—C26</td><td rowspan="1" colspan="1">108.3 (2)</td></tr><tr><td rowspan="1" colspan="1">N1—C4—C3</td><td rowspan="1" colspan="1">109.43 (17)</td><td rowspan="1" colspan="1">O2—C25—H25A</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">124.81 (18)</td><td rowspan="1" colspan="1">C26—C25—H25A</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">125.74 (18)</td><td rowspan="1" colspan="1">O2—C25—H25B</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C11</td><td rowspan="1" colspan="1">116.99 (17)</td><td rowspan="1" colspan="1">C26—C25—H25B</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C11</td><td rowspan="1" colspan="1">117.24 (17)</td><td rowspan="1" colspan="1">H25A—C25—H25B</td><td rowspan="1" colspan="1">108.4</td></tr><tr><td rowspan="1" colspan="1">N2—C6—C5</td><td rowspan="1" colspan="1">126.10 (18)</td><td rowspan="1" colspan="1">O3—C26—C25</td><td rowspan="1" colspan="1">108.8 (2)</td></tr><tr><td rowspan="1" colspan="1">N2—C6—C7</td><td rowspan="1" colspan="1">109.46 (17)</td><td rowspan="1" colspan="1">O3—C26—H26A</td><td rowspan="1" colspan="1">109.9</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C7</td><td rowspan="1" colspan="1">124.44 (18)</td><td rowspan="1" colspan="1">C25—C26—H26A</td><td rowspan="1" colspan="1">109.9</td></tr><tr><td rowspan="1" colspan="1">C8—C7—C6</td><td rowspan="1" colspan="1">107.41 (18)</td><td rowspan="1" colspan="1">O3—C26—H26B</td><td rowspan="1" colspan="1">109.9</td></tr><tr><td rowspan="1" colspan="1">C8—C7—H7</td><td rowspan="1" colspan="1">126.3</td><td rowspan="1" colspan="1">C25—C26—H26B</td><td rowspan="1" colspan="1">109.9</td></tr><tr><td rowspan="1" colspan="1">C6—C7—H7</td><td rowspan="1" colspan="1">126.3</td><td rowspan="1" colspan="1">H26A—C26—H26B</td><td rowspan="1" colspan="1">108.3</td></tr><tr><td rowspan="1" colspan="1">C7—C8—C9</td><td rowspan="1" colspan="1">107.03 (18)</td><td rowspan="1" colspan="1">C26—O3—C27C</td><td rowspan="1" colspan="1">91.8 (5)</td></tr><tr><td rowspan="1" colspan="1">C7—C8—H8</td><td rowspan="1" colspan="1">126.5</td><td rowspan="1" colspan="1">C26—O3—C27B</td><td rowspan="1" colspan="1">109.8 (6)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">126.5</td><td rowspan="1" colspan="1">C26—O3—C27A</td><td rowspan="1" colspan="1">121.5 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—C9—C10<sup>i</sup></td><td rowspan="1" colspan="1">125.72 (18)</td><td rowspan="1" colspan="1">C28A—C27A—O3</td><td rowspan="1" colspan="1">103.6 (5)</td></tr><tr><td rowspan="1" colspan="1">N2—C9—C8</td><td rowspan="1" colspan="1">109.42 (17)</td><td rowspan="1" colspan="1">C28A—C27A—H27A</td><td rowspan="1" colspan="1">111.0</td></tr><tr><td rowspan="1" colspan="1">C10<sup>i</sup>—C9—C8</td><td rowspan="1" colspan="1">124.69 (18)</td><td rowspan="1" colspan="1">O3—C27A—H27A</td><td rowspan="1" colspan="1">111.0</td></tr><tr><td rowspan="1" colspan="1">C1—C10—C9<sup>i</sup></td><td rowspan="1" colspan="1">124.99 (18)</td><td rowspan="1" colspan="1">C28A—C27A—H27B</td><td rowspan="1" colspan="1">111.0</td></tr><tr><td rowspan="1" colspan="1">C1—C10—C17</td><td rowspan="1" colspan="1">117.65 (17)</td><td rowspan="1" colspan="1">O3—C27A—H27B</td><td rowspan="1" colspan="1">111.0</td></tr><tr><td rowspan="1" colspan="1">C9<sup>i</sup>—C10—C17</td><td rowspan="1" colspan="1">117.36 (18)</td><td rowspan="1" colspan="1">H27A—C27A—H27B</td><td rowspan="1" colspan="1">109.0</td></tr><tr><td rowspan="1" colspan="1">C16—C11—C12</td><td rowspan="1" colspan="1">118.84 (19)</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28A—C27A</td><td rowspan="1" colspan="1">109.5 (5)</td></tr><tr><td rowspan="1" colspan="1">C16—C11—C5</td><td rowspan="1" colspan="1">120.98 (18)</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28A—H28A</td><td rowspan="1" colspan="1">109.8</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C5</td><td rowspan="1" colspan="1">120.17 (18)</td><td rowspan="1" colspan="1">C27A—C28A—H28A</td><td rowspan="1" colspan="1">109.8</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C13</td><td rowspan="1" colspan="1">120.5 (2)</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28A—H28B</td><td rowspan="1" colspan="1">109.8</td></tr><tr><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">C27A—C28A—H28B</td><td rowspan="1" colspan="1">109.8</td></tr><tr><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">H28A—C28A—H28B</td><td rowspan="1" colspan="1">108.2</td></tr><tr><td rowspan="1" colspan="1">C14—C13—C12</td><td rowspan="1" colspan="1">120.3 (2)</td><td rowspan="1" colspan="1">C28B—C27B—O3</td><td rowspan="1" colspan="1">102.5 (10)</td></tr><tr><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">C28B—C27B—H27C</td><td rowspan="1" colspan="1">111.3</td></tr><tr><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">O3—C27B—H27C</td><td rowspan="1" colspan="1">111.3</td></tr><tr><td rowspan="1" colspan="1">C13—C14—C15</td><td rowspan="1" colspan="1">119.6 (2)</td><td rowspan="1" colspan="1">C28B—C27B—H27D</td><td rowspan="1" colspan="1">111.3</td></tr><tr><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">120.2</td><td rowspan="1" colspan="1">O3—C27B—H27D</td><td rowspan="1" colspan="1">111.3</td></tr><tr><td rowspan="1" colspan="1">C15—C14—H14</td><td rowspan="1" colspan="1">120.2</td><td rowspan="1" colspan="1">H27C—C27B—H27D</td><td rowspan="1" colspan="1">109.2</td></tr><tr><td rowspan="1" colspan="1">C14—C15—C16</td><td rowspan="1" colspan="1">120.2 (2)</td><td rowspan="1" colspan="1">C27B—C28B—O1<sup>ii</sup></td><td rowspan="1" colspan="1">108.4 (10)</td></tr><tr><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C27B—C28B—H28C</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28B—H28C</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C11—C16—C15</td><td rowspan="1" colspan="1">120.6 (2)</td><td rowspan="1" colspan="1">C27B—C28B—H28D</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C11—C16—H16</td><td rowspan="1" colspan="1">119.7</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28B—H28D</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">119.7</td><td rowspan="1" colspan="1">H28C—C28B—H28D</td><td rowspan="1" colspan="1">108.4</td></tr><tr><td rowspan="1" colspan="1">C22—C17—C18</td><td rowspan="1" colspan="1">118.35 (17)</td><td rowspan="1" colspan="1">C28C—C27C—O3</td><td rowspan="1" colspan="1">96.2 (9)</td></tr><tr><td rowspan="1" colspan="1">C22—C17—C10</td><td rowspan="1" colspan="1">121.02 (17)</td><td rowspan="1" colspan="1">C28C—C27C—H27E</td><td rowspan="1" colspan="1">112.5</td></tr><tr><td rowspan="1" colspan="1">C18—C17—C10</td><td rowspan="1" colspan="1">120.63 (18)</td><td rowspan="1" colspan="1">O3—C27C—H27E</td><td rowspan="1" colspan="1">112.5</td></tr><tr><td rowspan="1" colspan="1">C19—C18—C17</td><td rowspan="1" colspan="1">120.8 (2)</td><td rowspan="1" colspan="1">C28C—C27C—H27F</td><td rowspan="1" colspan="1">112.5</td></tr><tr><td rowspan="1" colspan="1">C19—C18—H18</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">O3—C27C—H27F</td><td rowspan="1" colspan="1">112.5</td></tr><tr><td rowspan="1" colspan="1">C17—C18—H18</td><td rowspan="1" colspan="1">119.6</td><td rowspan="1" colspan="1">H27E—C27C—H27F</td><td rowspan="1" colspan="1">110.0</td></tr><tr><td rowspan="1" colspan="1">C18—C19—C20</td><td rowspan="1" colspan="1">120.3 (2)</td><td rowspan="1" colspan="1">C27C—C28C—O1<sup>ii</sup></td><td rowspan="1" colspan="1">100.7 (9)</td></tr><tr><td rowspan="1" colspan="1">C18—C19—H19</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C27C—C28C—H28E</td><td rowspan="1" colspan="1">111.6</td></tr><tr><td rowspan="1" colspan="1">C20—C19—H19</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28C—H28E</td><td rowspan="1" colspan="1">111.6</td></tr><tr><td rowspan="1" colspan="1">C21—C20—C19</td><td rowspan="1" colspan="1">119.7 (2)</td><td rowspan="1" colspan="1">C27C—C28C—H28F</td><td rowspan="1" colspan="1">111.6</td></tr><tr><td rowspan="1" colspan="1">C21—C20—H20</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">O1<sup>ii</sup>—C28C—H28F</td><td rowspan="1" colspan="1">111.6</td></tr><tr><td rowspan="1" colspan="1">C19—C20—H20</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">H28E—C28C—H28F</td><td rowspan="1" colspan="1">109.4</td></tr><tr><td rowspan="1" colspan="1">C20—C21—C22</td><td rowspan="1" colspan="1">120.0 (2)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+2, −<italic>y</italic>, −<italic>z</italic>+1; (ii) −<italic>x</italic>+2, −<italic>y</italic>−1, −<italic>z</italic>+1.</p></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><p>Cg1, Cg2 and Cg3 are the centroids of the N1/C1–C4,
N2/C6–C9 and C11–C16 rings, respectively.</p><table-wrap position="anchor" id="d1e3590"><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">C15—H15···<italic>Cg</italic>1<sup>iii</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.98</td><td rowspan="1" colspan="1">3.824 (2)</td><td rowspan="1" colspan="1">152</td></tr><tr><td rowspan="1" colspan="1">C20—H20···<italic>Cg</italic>3<sup>iv</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.84</td><td rowspan="1" colspan="1">3.746 (2)</td><td rowspan="1" colspan="1">164</td></tr><tr><td rowspan="1" colspan="1">C24—H24<italic>A</italic>···<italic>Cg</italic>2</td><td rowspan="1" colspan="1">0.97</td><td rowspan="1" colspan="1">2.73</td><td rowspan="1" colspan="1">3.686 (3)</td><td rowspan="1" colspan="1">167</td></tr></table></table-wrap><p>Symmetry codes: (iii) −<italic>x</italic>+2, −<italic>y</italic>, −<italic>z</italic>+2; (iv) −<italic>x</italic>+3, −<italic>y</italic>, −<italic>z</italic>+2.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Allen, F. H. (2002). <italic>Acta Cryst.</italic> B<bold>58</bold>, 380–388.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). <italic>J. Appl. Cryst.</italic><bold>38</bold>, 381–388.</mixed-citation></ref><ref id="bb3"><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="bb4"><mixed-citation publication-type="other">Cheng, B. & Scheidt, W. R. (1995). <italic>Inorg. Chim. Acta</italic>, <bold>237</bold>, 5–11.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Diskin-Posner, Y., Kumar, R. K. & Goldberg, I. (1999). <italic>New J. Chem.</italic><bold>23</bold>, 885–890.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Ezzayani, K., Nasri, S., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2013). <italic>Acta Cryst.</italic> E<bold>69</bold>, m114–m115.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Kojima, T., Nakanishi, T., Honda, T., Harada, R., Shiro, M. & Fukuzumi, S. (2009). <italic>Eur. J. Inorg. Chem.</italic> pp. 727–734.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Kumar, R. K., Goldborth, A. & Goldberg, I. (1997). <italic>Z. Kristallogr. New Cryst. Struct.</italic><bold>212</bold>, 383–384.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Mansour, A., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2010). <italic>Acta Cryst.</italic> E<bold>66</bold>, m509–m510.</mixed-citation></ref><ref id="bb12"><mixed-citation publication-type="other">McArdle, P. (1995). <italic>J. Appl. Cryst.</italic><bold>28</bold>, 65.</mixed-citation></ref><ref id="bb13"><mixed-citation publication-type="other">Oberda, K., Deperasińska, I., Nizhnik, Y., Jerzykiewicz, L. & Szemik-Hojniak, A. (2011). <italic>Polyhedron</italic>, <bold>30</bold>, 2391–2399.</mixed-citation></ref><ref id="bb14"><mixed-citation publication-type="other">Oxford Diffraction (2010). <italic>CrystAlis CCD</italic> and <italic>CrysAlis RED</italic> Oxford Diffraction Ltd, Yarnton, England.</mixed-citation></ref><ref id="bb15"><mixed-citation publication-type="other">Ricard, D., Richard, P. & Boitrel, B. (2001). <italic>Acta Cryst.</italic> E<bold>57</bold>, m404–m406.</mixed-citation></ref><ref id="bb16"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb17"><mixed-citation publication-type="other">Suijkerbuijk, B. M. J. M., Tooke, D. M., Spek, A. L., Van Koten, G. & Gebbink, R. J. M. K. (2007). <italic>Chem. Asian J.</italic><bold>2</bold>, 889–903.</mixed-citation></ref><ref id="bb18"><mixed-citation publication-type="other">Toumi, H., Belghith, Y., Daran, J.-C. & Nasri, H. (2013). <italic>Acta Cryst.</italic> E<bold>69</bold>, m354–m355.</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><p><italic>Cg</italic>1, <italic>Cg</italic>2 and <italic>Cg</italic>3 are the centroids of the N1/C1–C4, N2/C6–C9 and C11–C16 rings, respectively.</p></caption><table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><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">C15—H15⋯<italic>Cg</italic>1<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.98</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.824 (2)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">152</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C20—H20⋯<italic>Cg</italic>3<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.746 (2)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">164</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C24—H24<italic>A</italic>⋯<italic>Cg</italic>2</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.97</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.73</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.686 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">167</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-69-0m444-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-69-0m444-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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