MersV1, Pmc, Corpus, bibRecord, 000A05

2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol

Identifieur interne : 000A05 ( Pmc/Corpus ); précédent : 000A04; suivant : 000A06

2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol

Auteurs : Ludovic Akonan ; Kouassi Yves Guillaume Molou ; Adjo Adohi-Krou ; Akoun Abou ; Abodou Jules Tenon

Source :

Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2010.

RBID : PMC:2979779

Abstract

In the title compound, C₁₀H₁₂N₂OS, the asymmetric unit consists of two independent molecules. In the crystal structure, molecules form R₄⁴(28) centrosymmetric tetramers via O—H⋯N hydrogen bonds. These tetramers are stacked along the c axis via C—H⋯O hydrogen bonds. C—H⋯π and π–π interactions are also present; in the latter, the centroid–centroid distances are 4.075 (1) and 3.719 (1) Å.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979779

DOI: 10.1107/S1600536810001960
PubMed: 21579857
PubMed Central: 2979779

Links to Exploration step

PMC:2979779

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol</title>
<author><name sortKey="Akonan, Ludovic" sort="Akonan, Ludovic" uniqKey="Akonan L" first="Ludovic" last="Akonan">Ludovic Akonan</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Molou, Kouassi Yves Guillaume" sort="Molou, Kouassi Yves Guillaume" uniqKey="Molou K" first="Kouassi Yves Guillaume" last="Molou">Kouassi Yves Guillaume Molou</name>
<affiliation><nlm:aff id="b">Laboratoire de Chimie Organique, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Adohi Krou, Adjo" sort="Adohi Krou, Adjo" uniqKey="Adohi Krou A" first="Adjo" last="Adohi-Krou">Adjo Adohi-Krou</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Abou, Akoun" sort="Abou, Akoun" uniqKey="Abou A" first="Akoun" last="Abou">Akoun Abou</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tenon, Abodou Jules" sort="Tenon, Abodou Jules" uniqKey="Tenon A" first="Abodou Jules" last="Tenon">Abodou Jules Tenon</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
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<date when="2010">2010</date>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol</title>
<author><name sortKey="Akonan, Ludovic" sort="Akonan, Ludovic" uniqKey="Akonan L" first="Ludovic" last="Akonan">Ludovic Akonan</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Molou, Kouassi Yves Guillaume" sort="Molou, Kouassi Yves Guillaume" uniqKey="Molou K" first="Kouassi Yves Guillaume" last="Molou">Kouassi Yves Guillaume Molou</name>
<affiliation><nlm:aff id="b">Laboratoire de Chimie Organique, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Adohi Krou, Adjo" sort="Adohi Krou, Adjo" uniqKey="Adohi Krou A" first="Adjo" last="Adohi-Krou">Adjo Adohi-Krou</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Abou, Akoun" sort="Abou, Akoun" uniqKey="Abou A" first="Akoun" last="Abou">Akoun Abou</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tenon, Abodou Jules" sort="Tenon, Abodou Jules" uniqKey="Tenon A" first="Abodou Jules" last="Tenon">Abodou Jules Tenon</name>
<affiliation><nlm:aff id="a">Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</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="2010">2010</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p>In the title compound, C<sub>10</sub>
H<sub>12</sub>
N<sub>2</sub>
OS, the asymmetric unit consists of two independent molecules. In the crystal structure, molecules form <italic>R</italic>
<sub>4</sub>
<sup>4</sup>
(28) centrosymmetric tetramers <italic>via</italic>
 O—H⋯N hydrogen bonds. These tetramers are stacked along the <italic>c</italic>
 axis <italic>via</italic>
 C—H⋯O hydrogen bonds. C—H⋯π and π–π interactions are also present; in the latter, the centroid–centroid distances are 4.075 (1) and 3.719 (1) Å.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
<biblStruct></biblStruct>
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</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
  <front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr 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">21579857</article-id>
<article-id pub-id-type="pmc">2979779</article-id>
<article-id pub-id-type="publisher-id">wn2372</article-id>
<article-id pub-id-type="doi">10.1107/S1600536810001960</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536810001960</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol</article-title>
<alt-title><italic>C<sub>10</sub>
H<sub>12</sub>
N<sub>2</sub>
OS</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Akonan</surname>
<given-names>Ludovic</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>Molou</surname>
<given-names>Kouassi Yves Guillaume</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Adohi-Krou</surname>
<given-names>Adjo</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Abou</surname>
<given-names>Akoun</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Tenon</surname>
<given-names>Abodou Jules</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<aff id="a"><label>a</label>
Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</aff>
<aff id="b"><label>b</label>
Laboratoire de Chimie Organique, UFR SSMT, Université de Cocody 22 BP 582 Abidjan 22,<country>Côte d’Ivoire</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>ludovic.akonan@gmail.com</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>2</month>
<year>2010</year>
</pub-date>
<pub-date pub-type="epub"><day>23</day>
<month>1</month>
<year>2010</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>23</day>
<month>1</month>
<year>2010</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the 
 							. </pmc-comment>
      <volume>66</volume>
<issue>Pt 2</issue>
<issue-id pub-id-type="publisher-id">e100200</issue-id>
<fpage>o442</fpage>
<lpage>o442</lpage>
<history><date date-type="received"><day>17</day>
<month>12</month>
<year>2009</year>
</date>
<date date-type="accepted"><day>15</day>
<month>1</month>
<year>2010</year>
</date>
</history>
<permissions><copyright-statement>© Akonan et al. 2010</copyright-statement>
<copyright-year>2010</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/S1600536810001960">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>In the title compound, C<sub>10</sub>
H<sub>12</sub>
N<sub>2</sub>
OS, the asymmetric unit consists of two independent molecules. In the crystal structure, molecules form <italic>R</italic>
<sub>4</sub>
<sup>4</sup>
(28) centrosymmetric tetramers <italic>via</italic>
 O—H⋯N hydrogen bonds. These tetramers are stacked along the <italic>c</italic>
 axis <italic>via</italic>
 C—H⋯O hydrogen bonds. C—H⋯π and π–π interactions are also present; in the latter, the centroid–centroid distances are 4.075 (1) and 3.719 (1) Å.</p>
</abstract>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature</title>
<p>For the biological activity of compounds having benzimidazole ring systems, and a related structure, see: Akkurt <italic>et al.</italic>
 (2006<xref ref-type="bibr" rid="bb1"> ▶</xref>
). For other studies of the biological activity of benzimidazoles, see: Küçükbay <italic>et al.</italic>
 (2003<xref ref-type="bibr" rid="bb7"> ▶</xref>
), (2004<xref ref-type="bibr" rid="bb6"> ▶</xref>
); Puratchikody <italic>et al.</italic>
 (2008<xref ref-type="bibr" rid="bb10"> ▶</xref>
). For hydrogen-bond graph sets, see: Bernstein <italic>et al.</italic>
 (1995<xref ref-type="bibr" rid="bb3"> ▶</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-66-0o442-scheme1.jpg" position="float"></graphic>
</chem-struct>
</p>
</sec>
<sec sec-type="" 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>C<sub>10</sub>
H<sub>12</sub>
N<sub>2</sub>
OS</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 208.28</p>
</list-item>
<list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-66-0o442-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
 = 9.3235 (2) Å</p>
</list-item>
<list-item><p><italic>b</italic>
 = 9.7659 (2) Å</p>
</list-item>
<list-item><p><italic>c</italic>
 = 11.4588 (3) Å</p>
</list-item>
<list-item><p>α = 78.0849 (9)°</p>
</list-item>
<list-item><p>β = 88.9066 (8)°</p>
</list-item>
<list-item><p>γ = 88.1399 (9)°</p>
</list-item>
<list-item><p><italic>V</italic>
 = 1020.25 (4) Å<sup>3</sup>
</p>
</list-item>
<list-item><p><italic>Z</italic>
 = 4</p>
</list-item>
<list-item><p>Mo <italic>K</italic>
α radiation</p>
</list-item>
<list-item><p>μ = 0.29 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
 = 223 K</p>
</list-item>
<list-item><p>0.20 × 0.20 × 0.15 mm</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.1.2"><title>Data collection</title>
<p><list list-type="simple"><list-item><p>Nonius KappaCCD diffractometer</p>
</list-item>
<list-item><p>13769 measured reflections</p>
</list-item>
<list-item><p>5257 independent reflections</p>
</list-item>
<list-item><p>3996 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</p>
</list-item>
<list-item><p><italic>R</italic>
<sub>int</sub>
 = 0.036</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>
)] = 0.041</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.102</p>
</list-item>
<list-item><p><italic>S</italic>
 = 0.96</p>
</list-item>
<list-item><p>5242 reflections</p>
</list-item>
<list-item><p>261 parameters</p>
</list-item>
<list-item><p>H atoms treated by a mixture of independent and constrained refinement</p>
</list-item>
<list-item><p>Δρ<sub>max</sub>
 = 0.51 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
 = −0.32 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
</sec>
<sec id="d5e572"><title></title>
<p>Data collection: <italic>COLLECT</italic>
 (Nonius, 2001<xref ref-type="bibr" rid="bb8"> ▶</xref>
); cell refinement: <italic>DENZO</italic>
/<italic>SCALEPACK</italic>
 (Otwinowski & Minor, 1997<xref ref-type="bibr" rid="bb9"> ▶</xref>
); data reduction: <italic>DENZO</italic>
/<italic>SCALEPACK</italic>
; program(s) used to solve structure: <italic>SIR92</italic>
 (Altomare <italic>et al.</italic>
, 1994<xref ref-type="bibr" rid="bb2"> ▶</xref>
); program(s) used to refine structure: <italic>CRYSTALS</italic>
 (Betteridge <italic>et al.</italic>
, 2003<xref ref-type="bibr" rid="bb4"> ▶</xref>
); molecular graphics: <italic>ORTEP-3 for Windows</italic>
 (Farrugia, 1997<xref ref-type="bibr" rid="bb5"> ▶</xref>
) and <italic>PLATON</italic>
 (Spek, 2009<xref ref-type="bibr" rid="bb11"> ▶</xref>
); software used to prepare material for publication: <italic>CRYSTALS</italic>
.</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data" xlink:href="e-66-0o442-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablocks global, I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536810001960/wn2372sup1.cif">10.1107/S1600536810001960/wn2372sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-66-0o442-sup1.cif" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material content-type="local-data" xlink:href="e-66-0o442-Isup2.hkl" position="float" xlink:type="simple"><p>Structure factors: contains datablocks I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536810001960/wn2372Isup2.hkl">10.1107/S1600536810001960/wn2372Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-66-0o442-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?wn2372&file=wn2372sup0.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?wn2372sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?wn2372&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?wn2372">WN2372</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>We thank the Laboratoire de Physique des Interactions Ioniques et Spectropôle, Université de Provence, et Université Paul Cézanne, Faculté des Sciences et Techniques de Saint Jérôme, Marseilles, France, for the use of their diffractometer.</p>
</ack>
<app-group><app><title>supplementary crystallographic 
information</title>
<sec id="comment"><title>Comment </title>
<p>Numerous compounds having benzimidazole ring systems possess versatile
pharmacological activities such as antiviral, anthelmintic, spasmolytic,
antihypertensive and vasodilator (Akkurt <italic>et al.</italic>, 2006). It has
also been
reported that many benzimidazole derivatives have antimicrobial and antifungal
activities (Küçükbay <italic>et al.</italic>, 2003, 2004,
Puratchikody <italic>et
al.</italic>, 2008). Therefore, the synthesis of new benzimidazole
derivatives
is of considerable interest. In order to explore new benzimidazole
properties, the title compound has been synthesized and its crystal structure
determined.</p>
<p>The two independent molecules in the asymmetric unit of the title compound and
the atomic labeling scheme are shown in Fig.1. In this structure, the
nine-membered benzimidazole ring systems (N1A/C3A/N2A/C6A/C7A/C8A/C9A/C10A/C5A,
N1B/C3B/N2B/C6B/C7B/C8B/C9B/C10B/C5B) of both independent molecules are
essentially planar, the maximum deviation from planarity being, respectively,
0.016 (2) Å for atom C8A and 0.078 (16) Å for atom C3B.
These two ring systems make a dihedral angle of 73.95 (6)°.</p>
<p>In the crystal structure, we observe the formation of
<italic>R</italic>
<sub>4</sub>
<sup>4</sup>
(28) centrosymmetric tetramers (Bernstein <italic>et al.</italic>,
1995)
<italic>via</italic> O—H···N hydrogen bonds.
The tetramers are linked by two symmetric C—H···O hydrogen
bonds to form a zigzag infinite chain along the <italic>c</italic> axis.
The
supramolecular aggregation is completed by the presence of C—H···π
interactions (Table 1) and π–π stacking between two parallel imidazole
rings. The centroid···centroid distance of those rings,
<italic><italic>Cg</italic>
1</italic>
···<italic><italic>Cg</italic>
1</italic>
(1 - <italic>x</italic>
,1 - <italic>y</italic>
,1 - <italic>z</italic>)
and
<italic><italic>Cg</italic>
4</italic>
···<italic><italic>Cg</italic>
4</italic>
(-<italic>x</italic>
,2 - <italic>y</italic>
,-<italic>z</italic>)
are
4.075 (1) Å and 3.719 (1) Å, respectively  (Fig.3).</p>
</sec>
<sec id="experimental"><title>Experimental </title>
<p>2-Chloroethanol (1.6 ml, 24.4 mmol) and potasium carbonate (1.68 g, 12.2 mmol)
were added to 2-methylsulfanyl-1<italic>H</italic>-benzimidazole (1 g, 6.1 mmol) in
dimethyl sulfoxide (DMSO) (5 ml).
The reaction mixture was successively agitated
for 30 min at room temperature and at 323 K for 24 h.
50 ml of water was then added to the reaction mixture, and the products were
extracted with dichloromethane (3 × 50 ml). The combined organic
extracts were washed with brine (10 g of sodium chloride in 100 ml of water),
dried (Na<sub>2</sub>
SO<sub>4</sub>) and evaporated under reduced pressure.
The residue was
purified by column chromatography on silica gel (elution: hexane/ethyl acetate
(70:30, <italic>v</italic>
/<italic>v</italic>)) and the title compound resulted as a brown
powder (0.77 g, 61%) with a melting point of 409 K.
The brown powder was
dissolved in ethanol/hexane (3:1, <italic>v</italic>
/<italic>v</italic>) and, after four days,
brown crystals suitable for single-crystal X-ray diffraction analysis were
obtained.</p>
</sec>
<sec id="refinement"><title>Refinement </title>
<p>The H atoms bonded to O1A and O1B were located in a difference Fourier map;
their positional parameters and <italic>U</italic>
<sub>iso</sub> were refined freely.
Other H atoms
were placed at calculated positions, with C—H = 0.95 Å and refined using a
riding model, with <italic>U</italic>
<sub>iso</sub>
(H) constrained to be 1.2<italic>U</italic>
<sub>eq</sub>
(C).</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>The structure of the asymmetric unit of the title compound, showing the atomic labeling scheme, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.</p>
</caption>
<graphic xlink:href="e-66-0o442-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>Crystal packing, viewed down the a axis, showing the zigzag infinite chain of cyclic tetramers along the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonds have been omitted for clarity.</p>
</caption>
<graphic xlink:href="e-66-0o442-fig2"></graphic>
</fig>
<fig id="Fap3"><label>Fig. 3.</label>
<caption><p>Crystal packing, showing the π–π and C—H···π stacking interactions. The yellow dots are the centroids of benzene and imidazole rings. H atoms not involved in C—H···π interactions have been omitted for clarity.</p>
</caption>
<graphic xlink:href="e-66-0o442-fig3"></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">C<sub>10</sub>
H<sub>12</sub>
N<sub>2</sub>
OS</td>
<td rowspan="1" colspan="1"><italic>Z</italic>
 = 4</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 208.28</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 440</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>
 = 1.356 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">Melting point: 409 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
 = 9.3235 (2) Å</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 9.7659 (2) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 13769 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 11.4588 (3) Å</td>
<td rowspan="1" colspan="1">θ = 2–29°</td>
</tr>
<tr><td rowspan="1" colspan="1">α = 78.0849 (9)°</td>
<td rowspan="1" colspan="1">µ = 0.28 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 88.9066 (8)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 223 K</td>
</tr>
<tr><td rowspan="1" colspan="1">γ = 88.1399 (9)°</td>
<td rowspan="1" colspan="1">Prism, brown</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 1020.25 (4)  Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.20 × 0.20 × 0.15 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapdatacollectionlong"><title>Data collection</title>
<table-wrap position="anchor" id="d1e371"><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">Nonius KappaCCD diffractometer</td>
<td rowspan="1" colspan="1">3996 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.036</td>
</tr>
<tr><td rowspan="1" colspan="1">graphite</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 29.1°, θ<sub>min</sub>
 = 1.8°</td>
</tr>
<tr><td rowspan="1" colspan="1">φ and ω scans</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −12→12</td>
</tr>
<tr><td rowspan="1" colspan="1">13769 measured reflections</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −12→12</td>
</tr>
<tr><td rowspan="1" colspan="1">5257 independent reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −15→15</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraprefinementdatalong"><title>Refinement</title>
<table-wrap position="anchor" id="d1e469"><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>
)] = 0.041</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>
) = 0.102</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 0.96</td>
<td rowspan="1" colspan="1">  Method =  Modified Sheldrick 
<italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sup>2</sup>
)  +  (0.04<italic>P</italic>
)<sup>2</sup>
  +  0.62<italic>P</italic>
],  where <italic>P</italic>
 = [max(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
,0)  +  2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
]/3</td>
</tr>
<tr><td rowspan="1" colspan="1">5242 reflections</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 = 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1">261 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.51 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>
 = −0.32 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">88 constraints</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e629"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Experimental. <sup>1</sup>
H NMR (DMSO-d<sub>6</sub>
, 300 MHz, p.p.m.) δ: 2.71 (s, 3H, CH<sub>3</sub>); 3.68–3.74 (m
2H, CH<sub>2</sub>
O, J<sub>CH2—CH2</sub>
 = 5.7 Hz and J<sub>CH2—OH</sub> = 5.4 Hz); 4.17 (t, 2H,
CH<sub>2</sub>
N, J<sub>CH2—CH2</sub>
 = 5.7 Hz); 5.00 (t, 1H, OH, J<sub>CH2—OH</sub> = 5.4 Hz);
7.13–7.17 and 7.46–7.55 (m, 4H, C<sub>6</sub>
H<sub>4</sub>
). <sup>13</sup>
C NMR (DMSO-d<sub>6</sub>, 300 MHz,
p.p.m.) δ: 14.35 (CH<sub>3</sub>
); 46.25 (CH<sub>2</sub>N); 59.14 (CH2O); 109.75, 117.31,
121.14, 121.21, 136.75, 142.92 (C<sub>6</sub>
H<sub>5</sub>
); 152.48 (C═N).</td>
</tr>
<tr><td rowspan="1" colspan="1">Refinement. The 15 reflections 1 0 0; -1 1 0; 0 1 0; 1 1 0; -1 - 1 1; 0 - 1 1; 1 - 1 1; -1 0
1; 0 0 1; 1 0 1; -1 1 1; 0 1 1; 1 1 1; 0 0 2; 0 1 2 have been measured with
too low intensities. It might be caused by some systematical error, probably
by shielding by a beam stop of these diffractions. They were not used in the
refinement.</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="d1e718"><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">S1A</td>
<td rowspan="1" colspan="1">0.49131 (5)</td>
<td rowspan="1" colspan="1">0.82212 (5)</td>
<td rowspan="1" colspan="1">0.49825 (4)</td>
<td rowspan="1" colspan="1">0.0390</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3A</td>
<td rowspan="1" colspan="1">0.42886 (16)</td>
<td rowspan="1" colspan="1">0.69994 (15)</td>
<td rowspan="1" colspan="1">0.42198 (14)</td>
<td rowspan="1" colspan="1">0.0286</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1A</td>
<td rowspan="1" colspan="1">0.28691 (13)</td>
<td rowspan="1" colspan="1">0.66663 (13)</td>
<td rowspan="1" colspan="1">0.43140 (12)</td>
<td rowspan="1" colspan="1">0.0286</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5A</td>
<td rowspan="1" colspan="1">0.26838 (17)</td>
<td rowspan="1" colspan="1">0.57367 (15)</td>
<td rowspan="1" colspan="1">0.35708 (15)</td>
<td rowspan="1" colspan="1">0.0298</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6A</td>
<td rowspan="1" colspan="1">0.40349 (17)</td>
<td rowspan="1" colspan="1">0.55494 (15)</td>
<td rowspan="1" colspan="1">0.30706 (15)</td>
<td rowspan="1" colspan="1">0.0309</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2A</td>
<td rowspan="1" colspan="1">0.50366 (14)</td>
<td rowspan="1" colspan="1">0.63619 (13)</td>
<td rowspan="1" colspan="1">0.34868 (12)</td>
<td rowspan="1" colspan="1">0.0309</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7A</td>
<td rowspan="1" colspan="1">0.4221 (2)</td>
<td rowspan="1" colspan="1">0.46382 (18)</td>
<td rowspan="1" colspan="1">0.22858 (18)</td>
<td rowspan="1" colspan="1">0.0430</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8A</td>
<td rowspan="1" colspan="1">0.3031 (2)</td>
<td rowspan="1" colspan="1">0.39422 (19)</td>
<td rowspan="1" colspan="1">0.20412 (19)</td>
<td rowspan="1" colspan="1">0.0507</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9A</td>
<td rowspan="1" colspan="1">0.1686 (2)</td>
<td rowspan="1" colspan="1">0.41504 (19)</td>
<td rowspan="1" colspan="1">0.25355 (19)</td>
<td rowspan="1" colspan="1">0.0481</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10A</td>
<td rowspan="1" colspan="1">0.14723 (19)</td>
<td rowspan="1" colspan="1">0.50586 (17)</td>
<td rowspan="1" colspan="1">0.33090 (17)</td>
<td rowspan="1" colspan="1">0.0386</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2A</td>
<td rowspan="1" colspan="1">0.17826 (17)</td>
<td rowspan="1" colspan="1">0.70834 (17)</td>
<td rowspan="1" colspan="1">0.51181 (15)</td>
<td rowspan="1" colspan="1">0.0336</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1A</td>
<td rowspan="1" colspan="1">0.07853 (17)</td>
<td rowspan="1" colspan="1">0.82574 (17)</td>
<td rowspan="1" colspan="1">0.45194 (16)</td>
<td rowspan="1" colspan="1">0.0354</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1A</td>
<td rowspan="1" colspan="1">0.15279 (14)</td>
<td rowspan="1" colspan="1">0.95034 (13)</td>
<td rowspan="1" colspan="1">0.41601 (12)</td>
<td rowspan="1" colspan="1">0.0405</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4A</td>
<td rowspan="1" colspan="1">0.67938 (19)</td>
<td rowspan="1" colspan="1">0.8087 (2)</td>
<td rowspan="1" colspan="1">0.4688 (2)</td>
<td rowspan="1" colspan="1">0.0463</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1B</td>
<td rowspan="1" colspan="1">0.34070 (5)</td>
<td rowspan="1" colspan="1">1.07040 (5)</td>
<td rowspan="1" colspan="1">0.04701 (4)</td>
<td rowspan="1" colspan="1">0.0402</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3B</td>
<td rowspan="1" colspan="1">0.16057 (17)</td>
<td rowspan="1" colspan="1">1.10450 (15)</td>
<td rowspan="1" colspan="1">0.07442 (14)</td>
<td rowspan="1" colspan="1">0.0299</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2B</td>
<td rowspan="1" colspan="1">0.09036 (15)</td>
<td rowspan="1" colspan="1">1.06622 (14)</td>
<td rowspan="1" colspan="1">0.17658 (12)</td>
<td rowspan="1" colspan="1">0.0325</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6B</td>
<td rowspan="1" colspan="1">−0.04765 (17)</td>
<td rowspan="1" colspan="1">1.12427 (16)</td>
<td rowspan="1" colspan="1">0.15371 (14)</td>
<td rowspan="1" colspan="1">0.0307</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5B</td>
<td rowspan="1" colspan="1">−0.05673 (17)</td>
<td rowspan="1" colspan="1">1.19801 (16)</td>
<td rowspan="1" colspan="1">0.03565 (14)</td>
<td rowspan="1" colspan="1">0.0306</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1B</td>
<td rowspan="1" colspan="1">0.07856 (14)</td>
<td rowspan="1" colspan="1">1.18307 (13)</td>
<td rowspan="1" colspan="1">−0.01412 (12)</td>
<td rowspan="1" colspan="1">0.0313</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2B</td>
<td rowspan="1" colspan="1">0.12112 (19)</td>
<td rowspan="1" colspan="1">1.23474 (17)</td>
<td rowspan="1" colspan="1">−0.13814 (14)</td>
<td rowspan="1" colspan="1">0.0357</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1B</td>
<td rowspan="1" colspan="1">0.1892 (2)</td>
<td rowspan="1" colspan="1">1.37598 (19)</td>
<td rowspan="1" colspan="1">−0.15947 (16)</td>
<td rowspan="1" colspan="1">0.0419</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1B</td>
<td rowspan="1" colspan="1">0.21179 (14)</td>
<td rowspan="1" colspan="1">1.42576 (15)</td>
<td rowspan="1" colspan="1">−0.28301 (12)</td>
<td rowspan="1" colspan="1">0.0521</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10B</td>
<td rowspan="1" colspan="1">−0.18151 (19)</td>
<td rowspan="1" colspan="1">1.26805 (18)</td>
<td rowspan="1" colspan="1">−0.01093 (16)</td>
<td rowspan="1" colspan="1">0.0395</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9B</td>
<td rowspan="1" colspan="1">−0.2986 (2)</td>
<td rowspan="1" colspan="1">1.2612 (2)</td>
<td rowspan="1" colspan="1">0.06571 (18)</td>
<td rowspan="1" colspan="1">0.0458</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8B</td>
<td rowspan="1" colspan="1">−0.2918 (2)</td>
<td rowspan="1" colspan="1">1.1879 (2)</td>
<td rowspan="1" colspan="1">0.18335 (18)</td>
<td rowspan="1" colspan="1">0.0449</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7B</td>
<td rowspan="1" colspan="1">−0.16712 (19)</td>
<td rowspan="1" colspan="1">1.11853 (18)</td>
<td rowspan="1" colspan="1">0.22973 (16)</td>
<td rowspan="1" colspan="1">0.0381</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4B</td>
<td rowspan="1" colspan="1">0.3871 (2)</td>
<td rowspan="1" colspan="1">0.9554 (2)</td>
<td rowspan="1" colspan="1">0.18458 (19)</td>
<td rowspan="1" colspan="1">0.0578</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1B</td>
<td rowspan="1" colspan="1">0.305 (3)</td>
<td rowspan="1" colspan="1">1.398 (3)</td>
<td rowspan="1" colspan="1">−0.306 (3)</td>
<td rowspan="1" colspan="1">0.091 (9)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1A</td>
<td rowspan="1" colspan="1">0.136 (3)</td>
<td rowspan="1" colspan="1">0.992 (3)</td>
<td rowspan="1" colspan="1">0.329 (3)</td>
<td rowspan="1" colspan="1">0.094 (9)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.0555</td>
<td rowspan="1" colspan="1">0.5211</td>
<td rowspan="1" colspan="1">0.3642</td>
<td rowspan="1" colspan="1">0.0468*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">0.0895</td>
<td rowspan="1" colspan="1">0.3657</td>
<td rowspan="1" colspan="1">0.2337</td>
<td rowspan="1" colspan="1">0.0576*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.3134</td>
<td rowspan="1" colspan="1">0.3303</td>
<td rowspan="1" colspan="1">0.1520</td>
<td rowspan="1" colspan="1">0.0612*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7A</td>
<td rowspan="1" colspan="1">0.5130</td>
<td rowspan="1" colspan="1">0.4501</td>
<td rowspan="1" colspan="1">0.1934</td>
<td rowspan="1" colspan="1">0.0516*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">−0.1862</td>
<td rowspan="1" colspan="1">1.3181</td>
<td rowspan="1" colspan="1">−0.0913</td>
<td rowspan="1" colspan="1">0.0468*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9B</td>
<td rowspan="1" colspan="1">−0.3860</td>
<td rowspan="1" colspan="1">1.3078</td>
<td rowspan="1" colspan="1">0.0373</td>
<td rowspan="1" colspan="1">0.0552*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">−0.3748</td>
<td rowspan="1" colspan="1">1.1855</td>
<td rowspan="1" colspan="1">0.2331</td>
<td rowspan="1" colspan="1">0.0540*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7B</td>
<td rowspan="1" colspan="1">−0.1630</td>
<td rowspan="1" colspan="1">1.0688</td>
<td rowspan="1" colspan="1">0.3102</td>
<td rowspan="1" colspan="1">0.0456*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H41A</td>
<td rowspan="1" colspan="1">0.7284</td>
<td rowspan="1" colspan="1">0.8715</td>
<td rowspan="1" colspan="1">0.5062</td>
<td rowspan="1" colspan="1">0.0552*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H42A</td>
<td rowspan="1" colspan="1">0.6966</td>
<td rowspan="1" colspan="1">0.8319</td>
<td rowspan="1" colspan="1">0.3851</td>
<td rowspan="1" colspan="1">0.0552*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H43A</td>
<td rowspan="1" colspan="1">0.7132</td>
<td rowspan="1" colspan="1">0.7157</td>
<td rowspan="1" colspan="1">0.4993</td>
<td rowspan="1" colspan="1">0.0552*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H41B</td>
<td rowspan="1" colspan="1">0.4855</td>
<td rowspan="1" colspan="1">0.9276</td>
<td rowspan="1" colspan="1">0.1822</td>
<td rowspan="1" colspan="1">0.0696*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H42B</td>
<td rowspan="1" colspan="1">0.3707</td>
<td rowspan="1" colspan="1">1.0025</td>
<td rowspan="1" colspan="1">0.2486</td>
<td rowspan="1" colspan="1">0.0681*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H43B</td>
<td rowspan="1" colspan="1">0.3296</td>
<td rowspan="1" colspan="1">0.8751</td>
<td rowspan="1" colspan="1">0.1961</td>
<td rowspan="1" colspan="1">0.0681*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.0039</td>
<td rowspan="1" colspan="1">0.8396</td>
<td rowspan="1" colspan="1">0.5063</td>
<td rowspan="1" colspan="1">0.0420*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H12A</td>
<td rowspan="1" colspan="1">0.0383</td>
<td rowspan="1" colspan="1">0.8011</td>
<td rowspan="1" colspan="1">0.3838</td>
<td rowspan="1" colspan="1">0.0420*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21A</td>
<td rowspan="1" colspan="1">0.2257</td>
<td rowspan="1" colspan="1">0.7382</td>
<td rowspan="1" colspan="1">0.5744</td>
<td rowspan="1" colspan="1">0.0408*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22A</td>
<td rowspan="1" colspan="1">0.1226</td>
<td rowspan="1" colspan="1">0.6293</td>
<td rowspan="1" colspan="1">0.5442</td>
<td rowspan="1" colspan="1">0.0408*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21B</td>
<td rowspan="1" colspan="1">0.0383</td>
<td rowspan="1" colspan="1">1.2421</td>
<td rowspan="1" colspan="1">−0.1863</td>
<td rowspan="1" colspan="1">0.0432*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22B</td>
<td rowspan="1" colspan="1">0.1881</td>
<td rowspan="1" colspan="1">1.1693</td>
<td rowspan="1" colspan="1">−0.1609</td>
<td rowspan="1" colspan="1">0.0432*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11B</td>
<td rowspan="1" colspan="1">0.1277</td>
<td rowspan="1" colspan="1">1.4401</td>
<td rowspan="1" colspan="1">−0.1289</td>
<td rowspan="1" colspan="1">0.0504*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H12B</td>
<td rowspan="1" colspan="1">0.2787</td>
<td rowspan="1" colspan="1">1.3675</td>
<td rowspan="1" colspan="1">−0.1200</td>
<td rowspan="1" colspan="1">0.0504*</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="d1e1424"><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">S1A</td>
<td rowspan="1" colspan="1">0.0358 (2)</td>
<td rowspan="1" colspan="1">0.0417 (2)</td>
<td rowspan="1" colspan="1">0.0440 (3)</td>
<td rowspan="1" colspan="1">−0.00593 (17)</td>
<td rowspan="1" colspan="1">−0.00121 (18)</td>
<td rowspan="1" colspan="1">−0.01874 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A</td>
<td rowspan="1" colspan="1">0.0264 (7)</td>
<td rowspan="1" colspan="1">0.0263 (7)</td>
<td rowspan="1" colspan="1">0.0320 (8)</td>
<td rowspan="1" colspan="1">−0.0010 (5)</td>
<td rowspan="1" colspan="1">−0.0012 (6)</td>
<td rowspan="1" colspan="1">−0.0030 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A</td>
<td rowspan="1" colspan="1">0.0250 (6)</td>
<td rowspan="1" colspan="1">0.0282 (6)</td>
<td rowspan="1" colspan="1">0.0324 (7)</td>
<td rowspan="1" colspan="1">−0.0025 (5)</td>
<td rowspan="1" colspan="1">0.0027 (5)</td>
<td rowspan="1" colspan="1">−0.0059 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A</td>
<td rowspan="1" colspan="1">0.0301 (8)</td>
<td rowspan="1" colspan="1">0.0237 (7)</td>
<td rowspan="1" colspan="1">0.0345 (8)</td>
<td rowspan="1" colspan="1">−0.0019 (6)</td>
<td rowspan="1" colspan="1">−0.0017 (6)</td>
<td rowspan="1" colspan="1">−0.0030 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A</td>
<td rowspan="1" colspan="1">0.0304 (8)</td>
<td rowspan="1" colspan="1">0.0254 (7)</td>
<td rowspan="1" colspan="1">0.0370 (9)</td>
<td rowspan="1" colspan="1">0.0010 (6)</td>
<td rowspan="1" colspan="1">−0.0024 (6)</td>
<td rowspan="1" colspan="1">−0.0067 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2A</td>
<td rowspan="1" colspan="1">0.0258 (6)</td>
<td rowspan="1" colspan="1">0.0304 (7)</td>
<td rowspan="1" colspan="1">0.0371 (7)</td>
<td rowspan="1" colspan="1">0.0003 (5)</td>
<td rowspan="1" colspan="1">0.0009 (5)</td>
<td rowspan="1" colspan="1">−0.0085 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7A</td>
<td rowspan="1" colspan="1">0.0469 (10)</td>
<td rowspan="1" colspan="1">0.0357 (9)</td>
<td rowspan="1" colspan="1">0.0496 (11)</td>
<td rowspan="1" colspan="1">0.0062 (7)</td>
<td rowspan="1" colspan="1">−0.0007 (8)</td>
<td rowspan="1" colspan="1">−0.0174 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8A</td>
<td rowspan="1" colspan="1">0.0676 (14)</td>
<td rowspan="1" colspan="1">0.0342 (9)</td>
<td rowspan="1" colspan="1">0.0557 (12)</td>
<td rowspan="1" colspan="1">0.0016 (9)</td>
<td rowspan="1" colspan="1">−0.0119 (10)</td>
<td rowspan="1" colspan="1">−0.0213 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9A</td>
<td rowspan="1" colspan="1">0.0518 (11)</td>
<td rowspan="1" colspan="1">0.0344 (9)</td>
<td rowspan="1" colspan="1">0.0596 (12)</td>
<td rowspan="1" colspan="1">−0.0108 (8)</td>
<td rowspan="1" colspan="1">−0.0156 (10)</td>
<td rowspan="1" colspan="1">−0.0107 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10A</td>
<td rowspan="1" colspan="1">0.0331 (8)</td>
<td rowspan="1" colspan="1">0.0319 (8)</td>
<td rowspan="1" colspan="1">0.0487 (10)</td>
<td rowspan="1" colspan="1">−0.0086 (6)</td>
<td rowspan="1" colspan="1">−0.0055 (7)</td>
<td rowspan="1" colspan="1">−0.0017 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A</td>
<td rowspan="1" colspan="1">0.0312 (8)</td>
<td rowspan="1" colspan="1">0.0368 (8)</td>
<td rowspan="1" colspan="1">0.0311 (8)</td>
<td rowspan="1" colspan="1">−0.0020 (6)</td>
<td rowspan="1" colspan="1">0.0077 (7)</td>
<td rowspan="1" colspan="1">−0.0034 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A</td>
<td rowspan="1" colspan="1">0.0288 (8)</td>
<td rowspan="1" colspan="1">0.0419 (9)</td>
<td rowspan="1" colspan="1">0.0362 (9)</td>
<td rowspan="1" colspan="1">0.0013 (6)</td>
<td rowspan="1" colspan="1">0.0049 (7)</td>
<td rowspan="1" colspan="1">−0.0107 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1A</td>
<td rowspan="1" colspan="1">0.0449 (7)</td>
<td rowspan="1" colspan="1">0.0375 (6)</td>
<td rowspan="1" colspan="1">0.0389 (7)</td>
<td rowspan="1" colspan="1">−0.0012 (5)</td>
<td rowspan="1" colspan="1">−0.0030 (6)</td>
<td rowspan="1" colspan="1">−0.0068 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A</td>
<td rowspan="1" colspan="1">0.0330 (9)</td>
<td rowspan="1" colspan="1">0.0471 (10)</td>
<td rowspan="1" colspan="1">0.0608 (13)</td>
<td rowspan="1" colspan="1">−0.0082 (7)</td>
<td rowspan="1" colspan="1">−0.0080 (8)</td>
<td rowspan="1" colspan="1">−0.0140 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1B</td>
<td rowspan="1" colspan="1">0.0384 (2)</td>
<td rowspan="1" colspan="1">0.0427 (2)</td>
<td rowspan="1" colspan="1">0.0365 (2)</td>
<td rowspan="1" colspan="1">0.00559 (17)</td>
<td rowspan="1" colspan="1">0.00863 (18)</td>
<td rowspan="1" colspan="1">−0.00300 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3B</td>
<td rowspan="1" colspan="1">0.0355 (8)</td>
<td rowspan="1" colspan="1">0.0259 (7)</td>
<td rowspan="1" colspan="1">0.0286 (8)</td>
<td rowspan="1" colspan="1">−0.0031 (6)</td>
<td rowspan="1" colspan="1">0.0039 (6)</td>
<td rowspan="1" colspan="1">−0.0065 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2B</td>
<td rowspan="1" colspan="1">0.0381 (7)</td>
<td rowspan="1" colspan="1">0.0304 (7)</td>
<td rowspan="1" colspan="1">0.0284 (7)</td>
<td rowspan="1" colspan="1">−0.0011 (5)</td>
<td rowspan="1" colspan="1">0.0044 (6)</td>
<td rowspan="1" colspan="1">−0.0051 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6B</td>
<td rowspan="1" colspan="1">0.0365 (8)</td>
<td rowspan="1" colspan="1">0.0270 (7)</td>
<td rowspan="1" colspan="1">0.0296 (8)</td>
<td rowspan="1" colspan="1">−0.0048 (6)</td>
<td rowspan="1" colspan="1">0.0043 (6)</td>
<td rowspan="1" colspan="1">−0.0079 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5B</td>
<td rowspan="1" colspan="1">0.0341 (8)</td>
<td rowspan="1" colspan="1">0.0292 (7)</td>
<td rowspan="1" colspan="1">0.0292 (8)</td>
<td rowspan="1" colspan="1">−0.0060 (6)</td>
<td rowspan="1" colspan="1">0.0040 (6)</td>
<td rowspan="1" colspan="1">−0.0072 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1B</td>
<td rowspan="1" colspan="1">0.0349 (7)</td>
<td rowspan="1" colspan="1">0.0315 (7)</td>
<td rowspan="1" colspan="1">0.0263 (7)</td>
<td rowspan="1" colspan="1">−0.0031 (5)</td>
<td rowspan="1" colspan="1">0.0037 (5)</td>
<td rowspan="1" colspan="1">−0.0036 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2B</td>
<td rowspan="1" colspan="1">0.0414 (9)</td>
<td rowspan="1" colspan="1">0.0400 (9)</td>
<td rowspan="1" colspan="1">0.0245 (8)</td>
<td rowspan="1" colspan="1">−0.0014 (7)</td>
<td rowspan="1" colspan="1">0.0047 (7)</td>
<td rowspan="1" colspan="1">−0.0041 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1B</td>
<td rowspan="1" colspan="1">0.0409 (10)</td>
<td rowspan="1" colspan="1">0.0404 (9)</td>
<td rowspan="1" colspan="1">0.0397 (10)</td>
<td rowspan="1" colspan="1">−0.0038 (7)</td>
<td rowspan="1" colspan="1">0.0071 (8)</td>
<td rowspan="1" colspan="1">0.0021 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1B</td>
<td rowspan="1" colspan="1">0.0349 (7)</td>
<td rowspan="1" colspan="1">0.0628 (9)</td>
<td rowspan="1" colspan="1">0.0443 (8)</td>
<td rowspan="1" colspan="1">0.0089 (6)</td>
<td rowspan="1" colspan="1">0.0116 (6)</td>
<td rowspan="1" colspan="1">0.0195 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10B</td>
<td rowspan="1" colspan="1">0.0398 (9)</td>
<td rowspan="1" colspan="1">0.0407 (9)</td>
<td rowspan="1" colspan="1">0.0367 (9)</td>
<td rowspan="1" colspan="1">−0.0002 (7)</td>
<td rowspan="1" colspan="1">−0.0023 (7)</td>
<td rowspan="1" colspan="1">−0.0052 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9B</td>
<td rowspan="1" colspan="1">0.0358 (9)</td>
<td rowspan="1" colspan="1">0.0508 (11)</td>
<td rowspan="1" colspan="1">0.0519 (12)</td>
<td rowspan="1" colspan="1">0.0036 (8)</td>
<td rowspan="1" colspan="1">0.0000 (8)</td>
<td rowspan="1" colspan="1">−0.0137 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8B</td>
<td rowspan="1" colspan="1">0.0390 (10)</td>
<td rowspan="1" colspan="1">0.0491 (10)</td>
<td rowspan="1" colspan="1">0.0491 (11)</td>
<td rowspan="1" colspan="1">−0.0024 (8)</td>
<td rowspan="1" colspan="1">0.0116 (8)</td>
<td rowspan="1" colspan="1">−0.0170 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7B</td>
<td rowspan="1" colspan="1">0.0433 (10)</td>
<td rowspan="1" colspan="1">0.0378 (9)</td>
<td rowspan="1" colspan="1">0.0336 (9)</td>
<td rowspan="1" colspan="1">−0.0055 (7)</td>
<td rowspan="1" colspan="1">0.0104 (7)</td>
<td rowspan="1" colspan="1">−0.0088 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B</td>
<td rowspan="1" colspan="1">0.0442 (11)</td>
<td rowspan="1" colspan="1">0.0745 (14)</td>
<td rowspan="1" colspan="1">0.0448 (12)</td>
<td rowspan="1" colspan="1">0.0157 (10)</td>
<td rowspan="1" colspan="1">0.0037 (9)</td>
<td rowspan="1" colspan="1">0.0072 (10)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title>
<table-wrap position="anchor" id="d1e2001"><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">S1A—C3A</td>
<td rowspan="1" colspan="1">1.7383 (16)</td>
<td rowspan="1" colspan="1">S1B—C3B</td>
<td rowspan="1" colspan="1">1.7369 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1A—C4A</td>
<td rowspan="1" colspan="1">1.7851 (19)</td>
<td rowspan="1" colspan="1">S1B—C4B</td>
<td rowspan="1" colspan="1">1.788 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—N1A</td>
<td rowspan="1" colspan="1">1.3700 (19)</td>
<td rowspan="1" colspan="1">C3B—N2B</td>
<td rowspan="1" colspan="1">1.321 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—N2A</td>
<td rowspan="1" colspan="1">1.321 (2)</td>
<td rowspan="1" colspan="1">C3B—N1B</td>
<td rowspan="1" colspan="1">1.368 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C5A</td>
<td rowspan="1" colspan="1">1.384 (2)</td>
<td rowspan="1" colspan="1">N2B—C6B</td>
<td rowspan="1" colspan="1">1.396 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C2A</td>
<td rowspan="1" colspan="1">1.461 (2)</td>
<td rowspan="1" colspan="1">C6B—C5B</td>
<td rowspan="1" colspan="1">1.398 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—C6A</td>
<td rowspan="1" colspan="1">1.396 (2)</td>
<td rowspan="1" colspan="1">C6B—C7B</td>
<td rowspan="1" colspan="1">1.396 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—C10A</td>
<td rowspan="1" colspan="1">1.396 (2)</td>
<td rowspan="1" colspan="1">C5B—N1B</td>
<td rowspan="1" colspan="1">1.390 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A—N2A</td>
<td rowspan="1" colspan="1">1.397 (2)</td>
<td rowspan="1" colspan="1">C5B—C10B</td>
<td rowspan="1" colspan="1">1.388 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A—C7A</td>
<td rowspan="1" colspan="1">1.395 (2)</td>
<td rowspan="1" colspan="1">N1B—C2B</td>
<td rowspan="1" colspan="1">1.458 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7A—C8A</td>
<td rowspan="1" colspan="1">1.382 (3)</td>
<td rowspan="1" colspan="1">C2B—C1B</td>
<td rowspan="1" colspan="1">1.509 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7A—H7A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C2B—H21B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C8A—C9A</td>
<td rowspan="1" colspan="1">1.392 (3)</td>
<td rowspan="1" colspan="1">C2B—H22B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C8A—H8A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C1B—O1B</td>
<td rowspan="1" colspan="1">1.413 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9A—C10A</td>
<td rowspan="1" colspan="1">1.385 (3)</td>
<td rowspan="1" colspan="1">C1B—H11B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C9A—H9A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C1B—H12B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C10A—H10A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">O1B—H1B</td>
<td rowspan="1" colspan="1">0.95 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A—C1A</td>
<td rowspan="1" colspan="1">1.510 (2)</td>
<td rowspan="1" colspan="1">C10B—C9B</td>
<td rowspan="1" colspan="1">1.382 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A—H21A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C10B—H10B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A—H22A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C9B—C8B</td>
<td rowspan="1" colspan="1">1.391 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A—O1A</td>
<td rowspan="1" colspan="1">1.402 (2)</td>
<td rowspan="1" colspan="1">C9B—H9B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A—H11A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C8B—C7B</td>
<td rowspan="1" colspan="1">1.385 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A—H12A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C8B—H8B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">O1A—H1A</td>
<td rowspan="1" colspan="1">1.01 (3)</td>
<td rowspan="1" colspan="1">C7B—H7B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H41A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C4B—H41B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H42A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C4B—H42B</td>
<td rowspan="1" colspan="1">0.950</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H43A</td>
<td rowspan="1" colspan="1">0.950</td>
<td rowspan="1" colspan="1">C4B—H43B</td>
<td rowspan="1" colspan="1">0.950</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">C3A—S1A—C4A</td>
<td rowspan="1" colspan="1">100.28 (8)</td>
<td rowspan="1" colspan="1">C3B—S1B—C4B</td>
<td rowspan="1" colspan="1">100.22 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1A—C3A—N1A</td>
<td rowspan="1" colspan="1">119.56 (12)</td>
<td rowspan="1" colspan="1">S1B—C3B—N2B</td>
<td rowspan="1" colspan="1">126.69 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1A—C3A—N2A</td>
<td rowspan="1" colspan="1">126.71 (12)</td>
<td rowspan="1" colspan="1">S1B—C3B—N1B</td>
<td rowspan="1" colspan="1">119.73 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C3A—N2A</td>
<td rowspan="1" colspan="1">113.67 (14)</td>
<td rowspan="1" colspan="1">N2B—C3B—N1B</td>
<td rowspan="1" colspan="1">113.53 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—N1A—C5A</td>
<td rowspan="1" colspan="1">106.27 (13)</td>
<td rowspan="1" colspan="1">C3B—N2B—C6B</td>
<td rowspan="1" colspan="1">104.41 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3A—N1A—C2A</td>
<td rowspan="1" colspan="1">127.66 (14)</td>
<td rowspan="1" colspan="1">N2B—C6B—C5B</td>
<td rowspan="1" colspan="1">110.28 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—N1A—C2A</td>
<td rowspan="1" colspan="1">125.82 (13)</td>
<td rowspan="1" colspan="1">N2B—C6B—C7B</td>
<td rowspan="1" colspan="1">129.65 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C5A—C6A</td>
<td rowspan="1" colspan="1">105.66 (13)</td>
<td rowspan="1" colspan="1">C5B—C6B—C7B</td>
<td rowspan="1" colspan="1">120.07 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C5A—C10A</td>
<td rowspan="1" colspan="1">131.55 (15)</td>
<td rowspan="1" colspan="1">C6B—C5B—N1B</td>
<td rowspan="1" colspan="1">105.33 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A—C5A—C10A</td>
<td rowspan="1" colspan="1">122.79 (15)</td>
<td rowspan="1" colspan="1">C6B—C5B—C10B</td>
<td rowspan="1" colspan="1">122.56 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—C6A—N2A</td>
<td rowspan="1" colspan="1">110.23 (13)</td>
<td rowspan="1" colspan="1">N1B—C5B—C10B</td>
<td rowspan="1" colspan="1">132.10 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—C6A—C7A</td>
<td rowspan="1" colspan="1">120.05 (15)</td>
<td rowspan="1" colspan="1">C5B—N1B—C3B</td>
<td rowspan="1" colspan="1">106.45 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2A—C6A—C7A</td>
<td rowspan="1" colspan="1">129.72 (15)</td>
<td rowspan="1" colspan="1">C5B—N1B—C2B</td>
<td rowspan="1" colspan="1">126.32 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A—N2A—C3A</td>
<td rowspan="1" colspan="1">104.17 (13)</td>
<td rowspan="1" colspan="1">C3B—N1B—C2B</td>
<td rowspan="1" colspan="1">127.15 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A—C7A—C8A</td>
<td rowspan="1" colspan="1">117.44 (17)</td>
<td rowspan="1" colspan="1">N1B—C2B—C1B</td>
<td rowspan="1" colspan="1">113.41 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6A—C7A—H7A</td>
<td rowspan="1" colspan="1">120.6</td>
<td rowspan="1" colspan="1">N1B—C2B—H21B</td>
<td rowspan="1" colspan="1">108.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8A—C7A—H7A</td>
<td rowspan="1" colspan="1">122.0</td>
<td rowspan="1" colspan="1">C1B—C2B—H21B</td>
<td rowspan="1" colspan="1">108.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C7A—C8A—C9A</td>
<td rowspan="1" colspan="1">121.94 (17)</td>
<td rowspan="1" colspan="1">N1B—C2B—H22B</td>
<td rowspan="1" colspan="1">108.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C7A—C8A—H8A</td>
<td rowspan="1" colspan="1">119.0</td>
<td rowspan="1" colspan="1">C1B—C2B—H22B</td>
<td rowspan="1" colspan="1">108.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C9A—C8A—H8A</td>
<td rowspan="1" colspan="1">119.0</td>
<td rowspan="1" colspan="1">H21B—C2B—H22B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8A—C9A—C10A</td>
<td rowspan="1" colspan="1">121.66 (17)</td>
<td rowspan="1" colspan="1">C2B—C1B—O1B</td>
<td rowspan="1" colspan="1">109.85 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8A—C9A—H9A</td>
<td rowspan="1" colspan="1">119.2</td>
<td rowspan="1" colspan="1">C2B—C1B—H11B</td>
<td rowspan="1" colspan="1">109.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C10A—C9A—H9A</td>
<td rowspan="1" colspan="1">119.2</td>
<td rowspan="1" colspan="1">O1B—C1B—H11B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—C10A—C9A</td>
<td rowspan="1" colspan="1">116.10 (17)</td>
<td rowspan="1" colspan="1">C2B—C1B—H12B</td>
<td rowspan="1" colspan="1">109.4</td>
</tr>
<tr><td rowspan="1" colspan="1">C5A—C10A—H10A</td>
<td rowspan="1" colspan="1">122.0</td>
<td rowspan="1" colspan="1">O1B—C1B—H12B</td>
<td rowspan="1" colspan="1">109.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C9A—C10A—H10A</td>
<td rowspan="1" colspan="1">121.9</td>
<td rowspan="1" colspan="1">H11B—C1B—H12B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C2A—C1A</td>
<td rowspan="1" colspan="1">113.63 (13)</td>
<td rowspan="1" colspan="1">C1B—O1B—H1B</td>
<td rowspan="1" colspan="1">110.3 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C2A—H21A</td>
<td rowspan="1" colspan="1">108.4</td>
<td rowspan="1" colspan="1">C5B—C10B—C9B</td>
<td rowspan="1" colspan="1">116.51 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A—C2A—H21A</td>
<td rowspan="1" colspan="1">108.3</td>
<td rowspan="1" colspan="1">C5B—C10B—H10B</td>
<td rowspan="1" colspan="1">121.8</td>
</tr>
<tr><td rowspan="1" colspan="1">N1A—C2A—H22A</td>
<td rowspan="1" colspan="1">108.5</td>
<td rowspan="1" colspan="1">C9B—C10B—H10B</td>
<td rowspan="1" colspan="1">121.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A—C2A—H22A</td>
<td rowspan="1" colspan="1">108.5</td>
<td rowspan="1" colspan="1">C10B—C9B—C8B</td>
<td rowspan="1" colspan="1">121.79 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">H21A—C2A—H22A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C10B—C9B—H9B</td>
<td rowspan="1" colspan="1">119.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A—C1A—O1A</td>
<td rowspan="1" colspan="1">110.78 (13)</td>
<td rowspan="1" colspan="1">C8B—C9B—H9B</td>
<td rowspan="1" colspan="1">119.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A—C1A—H11A</td>
<td rowspan="1" colspan="1">109.2</td>
<td rowspan="1" colspan="1">C9B—C8B—C7B</td>
<td rowspan="1" colspan="1">121.60 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1A—C1A—H11A</td>
<td rowspan="1" colspan="1">109.2</td>
<td rowspan="1" colspan="1">C9B—C8B—H8B</td>
<td rowspan="1" colspan="1">119.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C2A—C1A—H12A</td>
<td rowspan="1" colspan="1">109.1</td>
<td rowspan="1" colspan="1">C7B—C8B—H8B</td>
<td rowspan="1" colspan="1">119.2</td>
</tr>
<tr><td rowspan="1" colspan="1">O1A—C1A—H12A</td>
<td rowspan="1" colspan="1">109.0</td>
<td rowspan="1" colspan="1">C6B—C7B—C8B</td>
<td rowspan="1" colspan="1">117.47 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">H11A—C1A—H12A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C6B—C7B—H7B</td>
<td rowspan="1" colspan="1">121.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C1A—O1A—H1A</td>
<td rowspan="1" colspan="1">110.8 (16)</td>
<td rowspan="1" colspan="1">C8B—C7B—H7B</td>
<td rowspan="1" colspan="1">121.3</td>
</tr>
<tr><td rowspan="1" colspan="1">S1A—C4A—H41A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">S1B—C4B—H41B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">S1A—C4A—H42A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">S1B—C4B—H42B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H41A—C4A—H42A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H41B—C4B—H42B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">S1A—C4A—H43A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">S1B—C4B—H43B</td>
<td rowspan="1" colspan="1">109.4</td>
</tr>
<tr><td rowspan="1" colspan="1">H41A—C4A—H43A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H41B—C4B—H43B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">H42A—C4A—H43A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">H42B—C4B—H43B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title>
<table-wrap position="anchor" id="d1e2676"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1"><italic>Cg</italic>
1 and <italic>Cg</italic>2 are the centroids of the N1A-C3A-N2A-C6A-C5A
and C5A—C10A rings, respectively.</td>
</tr>
</table>
</table-wrap>
<table-wrap position="anchor" id="d1e2685"><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">O1B—H1B···N2A<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.95 (3)</td>
<td rowspan="1" colspan="1">1.88 (3)</td>
<td rowspan="1" colspan="1">2.825 (3)</td>
<td rowspan="1" colspan="1">174 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1A—H1A···N2B</td>
<td rowspan="1" colspan="1">1.01 (3)</td>
<td rowspan="1" colspan="1">1.80 (3)</td>
<td rowspan="1" colspan="1">2.808 (3)</td>
<td rowspan="1" colspan="1">175 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H41A···O1A<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.95</td>
<td rowspan="1" colspan="1">2.42</td>
<td rowspan="1" colspan="1">3.366 (3)</td>
<td rowspan="1" colspan="1">174</td>
</tr>
<tr><td rowspan="1" colspan="1">C4A—H43A···<italic>Cg</italic>
2<sup>iii</sup>
</td>
<td rowspan="1" colspan="1">0.95</td>
<td rowspan="1" colspan="1">2.86</td>
<td rowspan="1" colspan="1">3.627 (2)</td>
<td rowspan="1" colspan="1">139</td>
</tr>
<tr><td rowspan="1" colspan="1">C4B—H43B···<italic>Cg</italic>
1</td>
<td rowspan="1" colspan="1">0.95</td>
<td rowspan="1" colspan="1">2.86</td>
<td rowspan="1" colspan="1">3.486 (2)</td>
<td rowspan="1" colspan="1">125</td>
</tr>
<tr><td rowspan="1" colspan="1">C10B—H10B···<italic>Cg</italic>
2<sup>iv</sup>
</td>
<td rowspan="1" colspan="1">0.95</td>
<td rowspan="1" colspan="1">2.74</td>
<td rowspan="1" colspan="1">3.631 (2)</td>
<td rowspan="1" colspan="1">157</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) −<italic>x</italic>
+1, −<italic>y</italic>
+2, −<italic>z</italic>
; (ii) −<italic>x</italic>
+1, −<italic>y</italic>
+2, −<italic>z</italic>
+1; (iii) −<italic>x</italic>
+1, −<italic>y</italic>
+1, −<italic>z</italic>
+1;  (iv) −<italic>x</italic>
, −<italic>y</italic>
+2, −<italic>z</italic>
.</p>
</sec>
</app>
</app-group>
<ref-list><title>References</title>
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 E<bold>62</bold>
, o185–o187.</mixed-citation>
</ref>
<ref id="bb2"><mixed-citation publication-type="other">Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). <italic>J. Appl. Cryst.</italic>
<bold>27</bold>
, 435.</mixed-citation>
</ref>
<ref id="bb3"><mixed-citation publication-type="other">Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). <italic>Angew. Chem. Int. Ed. Engl.</italic>
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, 1555–1573.</mixed-citation>
</ref>
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<bold>36</bold>
, 1487.</mixed-citation>
</ref>
<ref id="bb5"><mixed-citation publication-type="other">Farrugia, L. J. (1997). <italic>J. Appl. Cryst.</italic>
<bold>30</bold>
, 565.</mixed-citation>
</ref>
<ref id="bb6"><mixed-citation publication-type="other">Küçükbay, H., Durmaz, R., Okuyucu, N., Günal, S. & Kazaz, C. (2004). <italic>Arzneim. Forsch. (Drug Res.)</italic>
, <bold>54</bold>
, 64–68.</mixed-citation>
</ref>
<ref id="bb7"><mixed-citation publication-type="other">Küçükbay, H., Durmaz, R., Orhan, E. & Günal, S. (2003). <italic>Il Farmaco</italic>
, <bold>58</bold>
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</ref>
<ref id="bb8"><mixed-citation publication-type="other">Nonius (2001). <italic>COLLECT</italic>
 Nonius BV, Delft, The Netherlands.</mixed-citation>
</ref>
<ref id="bb9"><mixed-citation publication-type="other">Otwinowski, Z. & Minor, W. (1997). <italic>Methods in Enzymology</italic>
, Vol. 276, <italic>Macromolecular Crystallography</italic>
, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.</mixed-citation>
</ref>
<ref id="bb10"><mixed-citation publication-type="other">Puratchikody, A., Nagalakshmi, G. & Doble, M. (2008). <italic>Chem. Pharm. Bull.</italic>
<bold>56</bold>
, 273–281.</mixed-citation>
</ref>
<ref id="bb11"><mixed-citation publication-type="other">Spek, A. L. (2009). <italic>Acta Cryst.</italic>
 D<bold>65</bold>
, 148–155.</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 and <italic>Cg</italic>
2 are the centroids of the N1<italic>A</italic>
-C3<italic>A</italic>
-N2<italic>A</italic>
-C6<italic>A</italic>
-C5<italic>A</italic>
 and C5<italic>A</italic>
—C10<italic>A</italic>
 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">O1<italic>B</italic>
—H1<italic>B</italic>
⋯N2<italic>A</italic>
<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.95 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.88 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.825 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">174 (3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1<italic>A</italic>
—H1<italic>A</italic>
⋯N2<italic>B</italic>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.01 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.80 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.808 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">175 (3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C4<italic>A</italic>
—H41<italic>A</italic>
⋯O1<italic>A</italic>
<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.42</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.366 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">174</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C4<italic>A</italic>
—H43<italic>A</italic>
⋯<italic>Cg</italic>
2<sup>iii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.86</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.627 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">139</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C4<italic>B</italic>
—H43<italic>B</italic>
⋯<italic>Cg</italic>
1</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.86</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.486 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">125</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C10<italic>B</italic>
—H10<italic>B</italic>
⋯<italic>Cg</italic>
2<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.74</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.631 (2)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">157</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-66-0o442-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-66-0o442-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iii) <inline-formula><inline-graphic xlink:href="e-66-0o442-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iv) <inline-formula><inline-graphic xlink:href="e-66-0o442-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>

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2-[2-(Methyl­sulfan­yl)benzimidazol-1-yl]ethanol

2-[2-(Methyl­sulfan­yl)benzimidazol-1-yl]ethanol

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2-[2-(Methylsulfanyl)benzimidazol-1-yl]ethanol

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