MersV1, Pmc, Corpus, bibRecord, 000A22

(Anthracen-9-ylmethyl)benzylammonium chloride

Identifieur interne : 000A22 ( Pmc/Corpus ); précédent : 000A21; suivant : 000A23

(Anthracen-9-ylmethyl)benzylammonium chloride

Auteurs : Jian-Rong Han ; Wei Wang ; Xiao-Li Zhen ; Xia Tian ; Shou-Xin Liu

Source :

Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2011.

RBID : PMC:3120425

Abstract

In the title compound, C₂₂H₂₀N⁺·Cl⁻, the anthracene system makes a dihedral angle of 72.65 (4)° with the benzene ring. The C—N—C—C torsion angles in the chain connecting the benzene ring and anthracene system are 52.24 (15) and −170.73 (11)°. The crystal structure is stabilized by intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds, which link the molecules into tetramers about inversion centers.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120425

DOI: 10.1107/S1600536811016837
PubMed: 21754851
PubMed Central: 3120425

Links to Exploration step

PMC:3120425

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">(Anthracen-9-ylmethyl)benzylammonium chloride</title>
<author><name sortKey="Han, Jian Rong" sort="Han, Jian Rong" uniqKey="Han J" first="Jian-Rong" last="Han">Jian-Rong Han</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Wang, Wei" sort="Wang, Wei" uniqKey="Wang W" first="Wei" last="Wang">Wei Wang</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zhen, Xiao Li" sort="Zhen, Xiao Li" uniqKey="Zhen X" first="Xiao-Li" last="Zhen">Xiao-Li Zhen</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tian, Xia" sort="Tian, Xia" uniqKey="Tian X" first="Xia" last="Tian">Xia Tian</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Liu, Shou Xin" sort="Liu, Shou Xin" uniqKey="Liu S" first="Shou-Xin" last="Liu">Shou-Xin Liu</name>
<affiliation><nlm:aff id="b">College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">21754851</idno>
<idno type="pmc">3120425</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120425</idno>
<idno type="RBID">PMC:3120425</idno>
<idno type="doi">10.1107/S1600536811016837</idno>
<date when="2011">2011</date>
<idno type="wicri:Area/Pmc/Corpus">000A22</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A22</idno>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">(Anthracen-9-ylmethyl)benzylammonium chloride</title>
<author><name sortKey="Han, Jian Rong" sort="Han, Jian Rong" uniqKey="Han J" first="Jian-Rong" last="Han">Jian-Rong Han</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Wang, Wei" sort="Wang, Wei" uniqKey="Wang W" first="Wei" last="Wang">Wei Wang</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zhen, Xiao Li" sort="Zhen, Xiao Li" uniqKey="Zhen X" first="Xiao-Li" last="Zhen">Xiao-Li Zhen</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tian, Xia" sort="Tian, Xia" uniqKey="Tian X" first="Xia" last="Tian">Xia Tian</name>
<affiliation><nlm:aff id="a">College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Liu, Shou Xin" sort="Liu, Shou Xin" uniqKey="Liu S" first="Shou-Xin" last="Liu">Shou-Xin Liu</name>
<affiliation><nlm:aff id="b">College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title>
<idno type="eISSN">1600-5368</idno>
<imprint><date when="2011">2011</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
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</teiHeader>
<front><div type="abstract" xml:lang="en"><p>In the title compound, C<sub>22</sub>
H<sub>20</sub>
N<sup>+</sup>
·Cl<sup>−</sup>
, the anthracene system makes a dihedral angle of 72.65 (4)° with the benzene ring. The C—N—C—C torsion angles in the chain connecting the benzene ring and anthracene system are 52.24 (15) and −170.73 (11)°. The crystal structure is stabilized by intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds, which link the molecules into tetramers about inversion centers.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
  <front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title>
</journal-title-group>
<issn pub-type="epub">1600-5368</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">21754851</article-id>
<article-id pub-id-type="pmc">3120425</article-id>
<article-id pub-id-type="publisher-id">pv2409</article-id>
<article-id pub-id-type="doi">10.1107/S1600536811016837</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536811016837</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>(Anthracen-9-ylmethyl)benzylammonium chloride</article-title>
<alt-title><italic>C<sub>22</sub>
H<sub>20</sub>
N<sup>+</sup>
·Cl<sup>−</sup>
</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Han</surname>
<given-names>Jian-Rong</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>Wang</surname>
<given-names>Wei</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhen</surname>
<given-names>Xiao-Li</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Tian</surname>
<given-names>Xia</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Liu</surname>
<given-names>Shou-Xin</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
<xref ref-type="author-notes" rid="aunote1">‡</xref>
</contrib>
<aff id="a"><label>a</label>
College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</aff>
<aff id="b"><label>b</label>
College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018,<country>People’s Republic of China</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>han_jianrong@126com</email>
</corresp>
<fn id="aunote1"><label>‡</label>
<p>Additional correspondence author, e-mail: chlsx@263.net.</p>
</fn>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>6</month>
<year>2011</year>
</pub-date>
<pub-date pub-type="epub"><day>20</day>
<month>5</month>
<year>2011</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>20</day>
<month>5</month>
<year>2011</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the 
 							. </pmc-comment>
      <volume>67</volume>
<issue>Pt 6</issue>
<issue-id pub-id-type="publisher-id">e110600</issue-id>
<fpage>o1482</fpage>
<lpage>o1482</lpage>
<history><date date-type="received"><day>11</day>
<month>4</month>
<year>2011</year>
</date>
<date date-type="accepted"><day>04</day>
<month>5</month>
<year>2011</year>
</date>
</history>
<permissions><copyright-statement>© Han et al. 2011</copyright-statement>
<copyright-year>2011</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
</license>
</permissions>
<self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536811016837">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>In the title compound, C<sub>22</sub>
H<sub>20</sub>
N<sup>+</sup>
·Cl<sup>−</sup>
, the anthracene system makes a dihedral angle of 72.65 (4)° with the benzene ring. The C—N—C—C torsion angles in the chain connecting the benzene ring and anthracene system are 52.24 (15) and −170.73 (11)°. The crystal structure is stabilized by intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds, which link the molecules into tetramers about inversion centers.</p>
</abstract>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature</title>
<p>For the synthesis and structures of related compounds, see: Ashton <italic>et al.</italic>
 (1997<xref ref-type="bibr" rid="bb1"> ▶</xref>
). For formation of rotaxanes from <italic>sec</italic>
-ammonium salts and crown ethers, see: Nakazono <italic>et al.</italic>
 (2008<xref ref-type="bibr" rid="bb2"> ▶</xref>
).<chem-struct id="scheme1"><graphic xlink:href="e-67-o1482-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>22</sub>
H<sub>20</sub>
N<sup>+</sup>
·Cl<sup>−</sup>
</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 333.84</p>
</list-item>
<list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-67-o1482-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
 = 6.7457 (13) Å</p>
</list-item>
<list-item><p><italic>b</italic>
 = 10.761 (2) Å</p>
</list-item>
<list-item><p><italic>c</italic>
 = 13.033 (3) Å</p>
</list-item>
<list-item><p>α = 94.45 (3)°</p>
</list-item>
<list-item><p>β = 104.84 (3)°</p>
</list-item>
<list-item><p>γ = 104.48 (3)°</p>
</list-item>
<list-item><p><italic>V</italic>
 = 875.3 (3) Å<sup>3</sup>
</p>
</list-item>
<list-item><p><italic>Z</italic>
 = 2</p>
</list-item>
<list-item><p>Mo <italic>K</italic>
α radiation</p>
</list-item>
<list-item><p>μ = 0.22 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
 = 113 K</p>
</list-item>
<list-item><p>0.28 × 0.24 × 0.20 mm</p>
</list-item>
</list>
</p>
</sec>
<sec id="sec2.1.2"><title>Data collection</title>
<p><list list-type="simple"><list-item><p>Rigaku Saturn CCD area-detector diffractometer</p>
</list-item>
<list-item><p>Absorption correction: multi-scan (<italic>CrystalClear</italic>
; Rigaku/MSC, 2005<xref ref-type="bibr" rid="bb3"> ▶</xref>
) <italic>T</italic>
<sub>min</sub>
 = 0.941, <italic>T</italic>
<sub>max</sub>
 = 0.957</p>
</list-item>
<list-item><p>5882 measured reflections</p>
</list-item>
<list-item><p>3048 independent reflections</p>
</list-item>
<list-item><p>2342 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</p>
</list-item>
<list-item><p><italic>R</italic>
<sub>int</sub>
 = 0.027</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>
)] = 0.031</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.088</p>
</list-item>
<list-item><p><italic>S</italic>
 = 1.04</p>
</list-item>
<list-item><p>3048 reflections</p>
</list-item>
<list-item><p>226 parameters</p>
</list-item>
<list-item><p>3 restraints</p>
</list-item>
<list-item><p>H atoms treated by a mixture of independent and constrained refinement</p>
</list-item>
<list-item><p>Δρ<sub>max</sub>
 = 0.20 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
 = −0.21 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
</sec>
<sec id="d5e457"><title></title>
<p>Data collection: <italic>CrystalClear</italic>
 (Rigaku/MSC, 2005<xref ref-type="bibr" rid="bb3"> ▶</xref>
); cell refinement: <italic>CrystalClear</italic>
; data reduction: <italic>CrystalClear</italic>
; program(s) used to solve structure: <italic>SHELXS97</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb4"> ▶</xref>
); program(s) used to refine structure: <italic>SHELXL97</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb4"> ▶</xref>
); molecular graphics: <italic>SHELXTL</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb4"> ▶</xref>
); software used to prepare material for publication: <italic>SHELXTL</italic>
.</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data" xlink:href="e-67-o1482-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablocks I, global. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536811016837/pv2409sup1.cif">10.1107/S1600536811016837/pv2409sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-67-o1482-sup1.cif" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material content-type="local-data" xlink:href="e-67-o1482-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/S1600536811016837/pv2409Isup2.hkl">10.1107/S1600536811016837/pv2409Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-67-o1482-Isup2.hkl" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material content-type="local-data" xlink:href="e-67-o1482-Isup3.cml" mimetype="chemical" mime-subtype="x-cml" position="float" xlink:type="simple"><p>Supplementary material file. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536811016837/pv2409Isup3.cml">10.1107/S1600536811016837/pv2409Isup3.cml</ext-link>
</p>
</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?pv2409&file=pv2409sup0.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?pv2409sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?pv2409&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?pv2409">PV2409</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>We are grateful for financial support from the Hebei Natural Science Fundation (No. B2009000670) and the Foundation of the Education Department of Hebei Province (grant No. 2009117), People’s Republic of China.</p>
</ack>
<app-group><app><title>supplementary crystallographic 
information</title>
<sec id="comment"><title>Comment </title>
<p>Sec-ammonium salts and crown ethers combine well to yield a stable
pseudorotaxanes as a precursor of rotaxanes (Nakazono <italic>et al.</italic>,
2008). (9-Anthracenyl) benzylammonium hexafluorophosphate and aromatic
crown ethers give hydrogen-bonded complexes pseudorotaxane-like geometries
(Ashton <italic>et al.</italic>, 1997). In this paper we report the synthesis and
crystal strucure of (9-anthracenyl) benzyl ammonium chloride.</p>
<p>In the title compound (Fig. 1), anthracene ring makes a dihedral angle of
72.65 (4)° with benzene ring. The torsion angles in the chain connecting
the benzene and the anthracene rings, (C15/N1—C16/C17 and (C16/N1—C15/C14)
are 52.24 (15) ° and -170.73 (11)°, respectively. In the crystal structure,
the crystal packing is stabilized by intermolecular N1—H1A···Cl1 and
C16—H16A···Cl1 hydrogen bonds which link the molecules into tetramers
about inversion centers (Table 1 and Fig. 2).</p>
</sec>
<sec id="experimental"><title>Experimental </title>
<p>A mixture of 9-anthracenealdehyde (6.18 g, 30 mmol) and benzylamine (3.86 g,
36 mmol) and molecular Sieve in toluene (200 mL) was heated under reflux with
stirring in a water divider for 10 h. After the reaction mixture had
cooled down to room temperature, the solvent was removed in vacuo to give the
imine. The solid was dissolved in hot MeOH (150 mL), followed by drop-wise
addition of NaBH<sub>4</sub> (5.70 g, 150 mmol) and heating under reflux with stirring
for 8 h. The reaction mixture was then allowed to cool down to room
temperature, and concentrated HCl was added (pH<2). After evaporation of the
solvent, the residue was suspended in H<sub>2</sub>O (70 mL) and extracted with
CH<sub>2</sub>
Cl<sub>2</sub> (4 × 50 mL). The combined extracts were washed with 5% aqueous
NaHCO<sub>3</sub>
 (2× 70 mL) and H<sub>2</sub>
O (70 mL) and then dried (MgSO<sub>4</sub>). Removal
of the solvent in vacuo afforded the (9-anthracenyl)benzyl amine
which was treated according to literature (Ashton <italic>et al.</italic>, 1997)
to
prepare the title compound. Pale yellow single crystals of the title compound
suitable for X-ray analysis were obtained by slow evaporation of an methnol
solution.</p>
</sec>
<sec id="refinement"><title>Refinement </title>
<p>The H atoms were included at calculated positions with C—H = 0.93 and
0.97 Å for aryl and methylene type H-atoms, respectively, and
refined in a riding mode with <italic>U</italic>
<sub>iso</sub>
(H) = 1.2<italic>U</italic>
<sub>eq</sub>(C). The
amino H-atoms were located from a difference Fourier map and were allowed
to refine freely.</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>The molecular structure of the title complex, with 50% probablity ellipsoids.</p>
</caption>
<graphic xlink:href="e-67-o1482-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>Unit cell packing of the title complex, showing hydrogen bonded tetramers.</p>
</caption>
<graphic xlink:href="e-67-o1482-fig2"></graphic>
</fig>
</sec>
<sec id="tablewrapcrystaldatalong"><title>Crystal data</title>
<table-wrap position="anchor" id="d1e138"><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>22</sub>
H<sub>20</sub>
N<sup>+</sup>
·Cl<sup>−</sup>
</td>
<td rowspan="1" colspan="1"><italic>Z</italic>
 = 2</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
 = 333.84</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 352</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>
 = 1.267 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>
 = 6.7457 (13) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 2756 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
 = 10.761 (2) Å</td>
<td rowspan="1" colspan="1">θ = 2.4–27.9°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
 = 13.033 (3) Å</td>
<td rowspan="1" colspan="1">µ = 0.22 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">α = 94.45 (3)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
 = 113 K</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 104.84 (3)°</td>
<td rowspan="1" colspan="1">Block, yellow</td>
</tr>
<tr><td rowspan="1" colspan="1">γ = 104.48 (3)°</td>
<td rowspan="1" colspan="1">0.28 × 0.24 × 0.20 mm</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
 = 875.3 (3)  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="d1e275"><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">Rigaku Saturn CCD area-detector diffractometer</td>
<td rowspan="1" colspan="1">3048 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: rotating anode</td>
<td rowspan="1" colspan="1">2342 reflections with <italic>I</italic>
 > 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">confocal</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
 = 0.027</td>
</tr>
<tr><td rowspan="1" colspan="1">Detector resolution: 7.31 pixels mm<sup>-1</sup>
</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
 = 25.0°, θ<sub>min</sub>
 = 2.4°</td>
</tr>
<tr><td rowspan="1" colspan="1">ω and φ scans</td>
<td rowspan="1" colspan="1"><italic>h</italic>
 = −8→8</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>CrystalClear</italic>
; Rigaku/MSC, 2005)</td>
<td rowspan="1" colspan="1"><italic>k</italic>
 = −12→10</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
 = 0.941, <italic>T</italic>
<sub>max</sub>
 = 0.957</td>
<td rowspan="1" colspan="1"><italic>l</italic>
 = −15→15</td>
</tr>
<tr><td rowspan="1" colspan="1">5882 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="d1e398"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.031</td>
<td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.088</td>
<td rowspan="1" colspan="1"><italic>w</italic>
 = 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0502<italic>P</italic>
)<sup>2</sup>
]  where <italic>P</italic>
 = (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
 + 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
 = 1.04</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
 = 0.002</td>
</tr>
<tr><td rowspan="1" colspan="1">3048 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
 = 0.20 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">226 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
 = −0.21 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">3 restraints</td>
<td rowspan="1" colspan="1">Extinction correction: <italic>SHELXL97</italic>
 (Sheldrick, 2008), Fc<sup>*</sup>
=kFc[1+0.001xFc<sup>2</sup>
λ<sup>3</sup>
/sin(2θ)]<sup>-1/4</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1">Extinction coefficient: 0.152 (9)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e576"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.</td>
</tr>
<tr><td rowspan="1" colspan="1">Refinement. Refinement of <italic>F</italic>
<sup>2</sup>
 against ALL reflections. The weighted <italic>R</italic>-factor
<italic>wR</italic>
 and goodness of fit <italic>S</italic>
 are based on <italic>F</italic>
<sup>2</sup>, conventional
<italic>R</italic>
-factors <italic>R</italic>
 are based on <italic>F</italic>
, with <italic>F</italic> set to zero for
negative <italic>F</italic>
<sup>2</sup>
. The threshold expression of <italic>F</italic>
<sup>2</sup> >
σ(<italic>F</italic>
<sup>2</sup>
) is used only for calculating <italic>R</italic>
-factors(gt) <italic>etc</italic>.
and is not relevant to the choice of reflections for refinement.
<italic>R</italic>
-factors based on <italic>F</italic>
<sup>2</sup> are statistically about twice as large
as those based on <italic>F</italic>
, and <italic>R</italic>- factors based on ALL data will be
even larger.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapcoords"><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e675"><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">Cl1</td>
<td rowspan="1" colspan="1">0.17351 (5)</td>
<td rowspan="1" colspan="1">0.42040 (4)</td>
<td rowspan="1" colspan="1">0.40032 (3)</td>
<td rowspan="1" colspan="1">0.02288 (15)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.38238 (18)</td>
<td rowspan="1" colspan="1">0.52936 (11)</td>
<td rowspan="1" colspan="1">0.64009 (9)</td>
<td rowspan="1" colspan="1">0.0139 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.1631 (2)</td>
<td rowspan="1" colspan="1">0.21072 (14)</td>
<td rowspan="1" colspan="1">0.67206 (11)</td>
<td rowspan="1" colspan="1">0.0184 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">−0.0472 (2)</td>
<td rowspan="1" colspan="1">0.21057 (16)</td>
<td rowspan="1" colspan="1">0.61273 (12)</td>
<td rowspan="1" colspan="1">0.0242 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2</td>
<td rowspan="1" colspan="1">−0.0774</td>
<td rowspan="1" colspan="1">0.2890</td>
<td rowspan="1" colspan="1">0.6018</td>
<td rowspan="1" colspan="1">0.029*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">−0.2034 (3)</td>
<td rowspan="1" colspan="1">0.09727 (16)</td>
<td rowspan="1" colspan="1">0.57217 (13)</td>
<td rowspan="1" colspan="1">0.0305 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3</td>
<td rowspan="1" colspan="1">−0.3391</td>
<td rowspan="1" colspan="1">0.0995</td>
<td rowspan="1" colspan="1">0.5340</td>
<td rowspan="1" colspan="1">0.037*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">−0.1629 (3)</td>
<td rowspan="1" colspan="1">−0.02440 (17)</td>
<td rowspan="1" colspan="1">0.58713 (13)</td>
<td rowspan="1" colspan="1">0.0341 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4</td>
<td rowspan="1" colspan="1">−0.2721</td>
<td rowspan="1" colspan="1">−0.1009</td>
<td rowspan="1" colspan="1">0.5597</td>
<td rowspan="1" colspan="1">0.041*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0344 (3)</td>
<td rowspan="1" colspan="1">−0.02903 (16)</td>
<td rowspan="1" colspan="1">0.64127 (12)</td>
<td rowspan="1" colspan="1">0.0305 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H5</td>
<td rowspan="1" colspan="1">0.0595</td>
<td rowspan="1" colspan="1">−0.1091</td>
<td rowspan="1" colspan="1">0.6505</td>
<td rowspan="1" colspan="1">0.037*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.2045 (3)</td>
<td rowspan="1" colspan="1">0.08678 (15)</td>
<td rowspan="1" colspan="1">0.68441 (12)</td>
<td rowspan="1" colspan="1">0.0227 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.4101 (3)</td>
<td rowspan="1" colspan="1">0.08322 (16)</td>
<td rowspan="1" colspan="1">0.73768 (12)</td>
<td rowspan="1" colspan="1">0.0262 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7</td>
<td rowspan="1" colspan="1">0.4365</td>
<td rowspan="1" colspan="1">0.0029</td>
<td rowspan="1" colspan="1">0.7438</td>
<td rowspan="1" colspan="1">0.031*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.5764 (2)</td>
<td rowspan="1" colspan="1">0.19449 (15)</td>
<td rowspan="1" colspan="1">0.78173 (11)</td>
<td rowspan="1" colspan="1">0.0223 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.7883 (3)</td>
<td rowspan="1" colspan="1">0.18991 (18)</td>
<td rowspan="1" colspan="1">0.83401 (12)</td>
<td rowspan="1" colspan="1">0.0299 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9</td>
<td rowspan="1" colspan="1">0.8163</td>
<td rowspan="1" colspan="1">0.1098</td>
<td rowspan="1" colspan="1">0.8382</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.9485 (3)</td>
<td rowspan="1" colspan="1">0.29980 (18)</td>
<td rowspan="1" colspan="1">0.87736 (12)</td>
<td rowspan="1" colspan="1">0.0315 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10</td>
<td rowspan="1" colspan="1">1.0853</td>
<td rowspan="1" colspan="1">0.2948</td>
<td rowspan="1" colspan="1">0.9103</td>
<td rowspan="1" colspan="1">0.038*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.9084 (2)</td>
<td rowspan="1" colspan="1">0.42185 (17)</td>
<td rowspan="1" colspan="1">0.87262 (11)</td>
<td rowspan="1" colspan="1">0.0273 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11</td>
<td rowspan="1" colspan="1">1.0193</td>
<td rowspan="1" colspan="1">0.4969</td>
<td rowspan="1" colspan="1">0.9030</td>
<td rowspan="1" colspan="1">0.033*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.7099 (2)</td>
<td rowspan="1" colspan="1">0.43137 (16)</td>
<td rowspan="1" colspan="1">0.82427 (11)</td>
<td rowspan="1" colspan="1">0.0221 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H12</td>
<td rowspan="1" colspan="1">0.6871</td>
<td rowspan="1" colspan="1">0.5130</td>
<td rowspan="1" colspan="1">0.8231</td>
<td rowspan="1" colspan="1">0.026*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.5357 (2)</td>
<td rowspan="1" colspan="1">0.31906 (15)</td>
<td rowspan="1" colspan="1">0.77525 (11)</td>
<td rowspan="1" colspan="1">0.0188 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.3287 (2)</td>
<td rowspan="1" colspan="1">0.32511 (14)</td>
<td rowspan="1" colspan="1">0.72005 (11)</td>
<td rowspan="1" colspan="1">0.0170 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.2884 (2)</td>
<td rowspan="1" colspan="1">0.45631 (14)</td>
<td rowspan="1" colspan="1">0.71774 (11)</td>
<td rowspan="1" colspan="1">0.0167 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15A</td>
<td rowspan="1" colspan="1">0.1356</td>
<td rowspan="1" colspan="1">0.4454</td>
<td rowspan="1" colspan="1">0.6977</td>
<td rowspan="1" colspan="1">0.020*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15B</td>
<td rowspan="1" colspan="1">0.3499</td>
<td rowspan="1" colspan="1">0.5065</td>
<td rowspan="1" colspan="1">0.7891</td>
<td rowspan="1" colspan="1">0.020*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.3787 (2)</td>
<td rowspan="1" colspan="1">0.66897 (14)</td>
<td rowspan="1" colspan="1">0.64641 (11)</td>
<td rowspan="1" colspan="1">0.0159 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16A</td>
<td rowspan="1" colspan="1">0.2322</td>
<td rowspan="1" colspan="1">0.6725</td>
<td rowspan="1" colspan="1">0.6209</td>
<td rowspan="1" colspan="1">0.019*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H16B</td>
<td rowspan="1" colspan="1">0.4571</td>
<td rowspan="1" colspan="1">0.7116</td>
<td rowspan="1" colspan="1">0.6000</td>
<td rowspan="1" colspan="1">0.019*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.4765 (2)</td>
<td rowspan="1" colspan="1">0.74042 (14)</td>
<td rowspan="1" colspan="1">0.75999 (11)</td>
<td rowspan="1" colspan="1">0.0160 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.3455 (2)</td>
<td rowspan="1" colspan="1">0.75556 (14)</td>
<td rowspan="1" colspan="1">0.82421 (12)</td>
<td rowspan="1" colspan="1">0.0214 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H18</td>
<td rowspan="1" colspan="1">0.1978</td>
<td rowspan="1" colspan="1">0.7247</td>
<td rowspan="1" colspan="1">0.7963</td>
<td rowspan="1" colspan="1">0.026*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.4352 (3)</td>
<td rowspan="1" colspan="1">0.81680 (15)</td>
<td rowspan="1" colspan="1">0.93001 (12)</td>
<td rowspan="1" colspan="1">0.0277 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19</td>
<td rowspan="1" colspan="1">0.3472</td>
<td rowspan="1" colspan="1">0.8261</td>
<td rowspan="1" colspan="1">0.9729</td>
<td rowspan="1" colspan="1">0.033*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">0.6531 (3)</td>
<td rowspan="1" colspan="1">0.86365 (16)</td>
<td rowspan="1" colspan="1">0.97157 (13)</td>
<td rowspan="1" colspan="1">0.0300 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20</td>
<td rowspan="1" colspan="1">0.7122</td>
<td rowspan="1" colspan="1">0.9046</td>
<td rowspan="1" colspan="1">1.0424</td>
<td rowspan="1" colspan="1">0.036*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.7851 (3)</td>
<td rowspan="1" colspan="1">0.84988 (15)</td>
<td rowspan="1" colspan="1">0.90801 (12)</td>
<td rowspan="1" colspan="1">0.0254 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21</td>
<td rowspan="1" colspan="1">0.9326</td>
<td rowspan="1" colspan="1">0.8817</td>
<td rowspan="1" colspan="1">0.9360</td>
<td rowspan="1" colspan="1">0.030*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.6962 (2)</td>
<td rowspan="1" colspan="1">0.78841 (14)</td>
<td rowspan="1" colspan="1">0.80265 (11)</td>
<td rowspan="1" colspan="1">0.0194 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22</td>
<td rowspan="1" colspan="1">0.7848</td>
<td rowspan="1" colspan="1">0.7793</td>
<td rowspan="1" colspan="1">0.7601</td>
<td rowspan="1" colspan="1">0.023*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1A</td>
<td rowspan="1" colspan="1">0.5219 (14)</td>
<td rowspan="1" colspan="1">0.5298 (15)</td>
<td rowspan="1" colspan="1">0.6487 (11)</td>
<td rowspan="1" colspan="1">0.027 (4)*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1B</td>
<td rowspan="1" colspan="1">0.3065 (17)</td>
<td rowspan="1" colspan="1">0.4908 (14)</td>
<td rowspan="1" colspan="1">0.5707 (8)</td>
<td rowspan="1" colspan="1">0.018 (4)*</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="d1e1263"><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">Cl1</td>
<td rowspan="1" colspan="1">0.0145 (2)</td>
<td rowspan="1" colspan="1">0.0350 (3)</td>
<td rowspan="1" colspan="1">0.0170 (2)</td>
<td rowspan="1" colspan="1">0.00489 (17)</td>
<td rowspan="1" colspan="1">0.00408 (14)</td>
<td rowspan="1" colspan="1">−0.00094 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0128 (6)</td>
<td rowspan="1" colspan="1">0.0149 (7)</td>
<td rowspan="1" colspan="1">0.0127 (6)</td>
<td rowspan="1" colspan="1">0.0023 (5)</td>
<td rowspan="1" colspan="1">0.0032 (5)</td>
<td rowspan="1" colspan="1">0.0016 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0249 (8)</td>
<td rowspan="1" colspan="1">0.0171 (8)</td>
<td rowspan="1" colspan="1">0.0153 (7)</td>
<td rowspan="1" colspan="1">0.0035 (7)</td>
<td rowspan="1" colspan="1">0.0110 (6)</td>
<td rowspan="1" colspan="1">0.0039 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0265 (9)</td>
<td rowspan="1" colspan="1">0.0237 (9)</td>
<td rowspan="1" colspan="1">0.0219 (8)</td>
<td rowspan="1" colspan="1">0.0031 (7)</td>
<td rowspan="1" colspan="1">0.0102 (7)</td>
<td rowspan="1" colspan="1">0.0024 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0249 (9)</td>
<td rowspan="1" colspan="1">0.0339 (11)</td>
<td rowspan="1" colspan="1">0.0270 (9)</td>
<td rowspan="1" colspan="1">−0.0032 (8)</td>
<td rowspan="1" colspan="1">0.0090 (7)</td>
<td rowspan="1" colspan="1">0.0034 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0413 (11)</td>
<td rowspan="1" colspan="1">0.0230 (9)</td>
<td rowspan="1" colspan="1">0.0302 (9)</td>
<td rowspan="1" colspan="1">−0.0108 (8)</td>
<td rowspan="1" colspan="1">0.0172 (8)</td>
<td rowspan="1" colspan="1">0.0002 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0479 (11)</td>
<td rowspan="1" colspan="1">0.0167 (9)</td>
<td rowspan="1" colspan="1">0.0285 (9)</td>
<td rowspan="1" colspan="1">0.0017 (8)</td>
<td rowspan="1" colspan="1">0.0208 (8)</td>
<td rowspan="1" colspan="1">0.0045 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0365 (10)</td>
<td rowspan="1" colspan="1">0.0161 (8)</td>
<td rowspan="1" colspan="1">0.0194 (8)</td>
<td rowspan="1" colspan="1">0.0044 (7)</td>
<td rowspan="1" colspan="1">0.0171 (7)</td>
<td rowspan="1" colspan="1">0.0039 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0434 (10)</td>
<td rowspan="1" colspan="1">0.0212 (9)</td>
<td rowspan="1" colspan="1">0.0259 (8)</td>
<td rowspan="1" colspan="1">0.0176 (8)</td>
<td rowspan="1" colspan="1">0.0201 (8)</td>
<td rowspan="1" colspan="1">0.0109 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0321 (9)</td>
<td rowspan="1" colspan="1">0.0257 (9)</td>
<td rowspan="1" colspan="1">0.0171 (7)</td>
<td rowspan="1" colspan="1">0.0140 (8)</td>
<td rowspan="1" colspan="1">0.0138 (7)</td>
<td rowspan="1" colspan="1">0.0085 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0413 (10)</td>
<td rowspan="1" colspan="1">0.0403 (11)</td>
<td rowspan="1" colspan="1">0.0247 (9)</td>
<td rowspan="1" colspan="1">0.0288 (9)</td>
<td rowspan="1" colspan="1">0.0174 (8)</td>
<td rowspan="1" colspan="1">0.0174 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0261 (9)</td>
<td rowspan="1" colspan="1">0.0532 (12)</td>
<td rowspan="1" colspan="1">0.0221 (8)</td>
<td rowspan="1" colspan="1">0.0187 (9)</td>
<td rowspan="1" colspan="1">0.0089 (7)</td>
<td rowspan="1" colspan="1">0.0148 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.0264 (9)</td>
<td rowspan="1" colspan="1">0.0391 (10)</td>
<td rowspan="1" colspan="1">0.0164 (8)</td>
<td rowspan="1" colspan="1">0.0077 (8)</td>
<td rowspan="1" colspan="1">0.0065 (7)</td>
<td rowspan="1" colspan="1">0.0068 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.0253 (8)</td>
<td rowspan="1" colspan="1">0.0254 (9)</td>
<td rowspan="1" colspan="1">0.0164 (7)</td>
<td rowspan="1" colspan="1">0.0073 (7)</td>
<td rowspan="1" colspan="1">0.0069 (6)</td>
<td rowspan="1" colspan="1">0.0048 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.0251 (8)</td>
<td rowspan="1" colspan="1">0.0225 (8)</td>
<td rowspan="1" colspan="1">0.0138 (7)</td>
<td rowspan="1" colspan="1">0.0095 (7)</td>
<td rowspan="1" colspan="1">0.0107 (6)</td>
<td rowspan="1" colspan="1">0.0056 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.0226 (8)</td>
<td rowspan="1" colspan="1">0.0167 (8)</td>
<td rowspan="1" colspan="1">0.0157 (7)</td>
<td rowspan="1" colspan="1">0.0061 (6)</td>
<td rowspan="1" colspan="1">0.0111 (6)</td>
<td rowspan="1" colspan="1">0.0039 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0176 (8)</td>
<td rowspan="1" colspan="1">0.0164 (8)</td>
<td rowspan="1" colspan="1">0.0173 (7)</td>
<td rowspan="1" colspan="1">0.0041 (6)</td>
<td rowspan="1" colspan="1">0.0075 (6)</td>
<td rowspan="1" colspan="1">0.0033 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.0159 (7)</td>
<td rowspan="1" colspan="1">0.0143 (8)</td>
<td rowspan="1" colspan="1">0.0189 (7)</td>
<td rowspan="1" colspan="1">0.0049 (6)</td>
<td rowspan="1" colspan="1">0.0056 (6)</td>
<td rowspan="1" colspan="1">0.0059 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.0197 (8)</td>
<td rowspan="1" colspan="1">0.0097 (7)</td>
<td rowspan="1" colspan="1">0.0197 (7)</td>
<td rowspan="1" colspan="1">0.0051 (6)</td>
<td rowspan="1" colspan="1">0.0056 (6)</td>
<td rowspan="1" colspan="1">0.0053 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.0231 (8)</td>
<td rowspan="1" colspan="1">0.0166 (8)</td>
<td rowspan="1" colspan="1">0.0277 (8)</td>
<td rowspan="1" colspan="1">0.0078 (7)</td>
<td rowspan="1" colspan="1">0.0099 (7)</td>
<td rowspan="1" colspan="1">0.0057 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.0395 (10)</td>
<td rowspan="1" colspan="1">0.0256 (9)</td>
<td rowspan="1" colspan="1">0.0255 (8)</td>
<td rowspan="1" colspan="1">0.0147 (8)</td>
<td rowspan="1" colspan="1">0.0168 (7)</td>
<td rowspan="1" colspan="1">0.0038 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">0.0439 (10)</td>
<td rowspan="1" colspan="1">0.0219 (9)</td>
<td rowspan="1" colspan="1">0.0211 (8)</td>
<td rowspan="1" colspan="1">0.0095 (8)</td>
<td rowspan="1" colspan="1">0.0049 (7)</td>
<td rowspan="1" colspan="1">−0.0015 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.0251 (8)</td>
<td rowspan="1" colspan="1">0.0180 (8)</td>
<td rowspan="1" colspan="1">0.0269 (8)</td>
<td rowspan="1" colspan="1">0.0029 (7)</td>
<td rowspan="1" colspan="1">0.0006 (7)</td>
<td rowspan="1" colspan="1">0.0008 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.0216 (8)</td>
<td rowspan="1" colspan="1">0.0148 (8)</td>
<td rowspan="1" colspan="1">0.0224 (8)</td>
<td rowspan="1" colspan="1">0.0046 (6)</td>
<td rowspan="1" colspan="1">0.0079 (6)</td>
<td rowspan="1" colspan="1">0.0031 (6)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title>
<table-wrap position="anchor" id="d1e1678"><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">N1—C15</td>
<td rowspan="1" colspan="1">1.4990 (17)</td>
<td rowspan="1" colspan="1">C10—H10</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C16</td>
<td rowspan="1" colspan="1">1.5051 (18)</td>
<td rowspan="1" colspan="1">C11—C12</td>
<td rowspan="1" colspan="1">1.359 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1A</td>
<td rowspan="1" colspan="1">0.917 (8)</td>
<td rowspan="1" colspan="1">C11—H11</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1B</td>
<td rowspan="1" colspan="1">0.922 (8)</td>
<td rowspan="1" colspan="1">C12—C13</td>
<td rowspan="1" colspan="1">1.426 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C14</td>
<td rowspan="1" colspan="1">1.410 (2)</td>
<td rowspan="1" colspan="1">C12—H12</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.431 (2)</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.418 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.442 (2)</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.504 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.360 (2)</td>
<td rowspan="1" colspan="1">C15—H15A</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">C15—H15B</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.421 (2)</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.512 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C16—H16A</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.352 (2)</td>
<td rowspan="1" colspan="1">C16—H16B</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C17—C22</td>
<td rowspan="1" colspan="1">1.386 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.425 (2)</td>
<td rowspan="1" colspan="1">C17—C18</td>
<td rowspan="1" colspan="1">1.3922 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—H5</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C18—C19</td>
<td rowspan="1" colspan="1">1.391 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C7</td>
<td rowspan="1" colspan="1">1.394 (2)</td>
<td rowspan="1" colspan="1">C18—H18</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8</td>
<td rowspan="1" colspan="1">1.383 (2)</td>
<td rowspan="1" colspan="1">C19—C20</td>
<td rowspan="1" colspan="1">1.374 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—H7</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C19—H19</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C9</td>
<td rowspan="1" colspan="1">1.432 (2)</td>
<td rowspan="1" colspan="1">C20—C21</td>
<td rowspan="1" colspan="1">1.388 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C13</td>
<td rowspan="1" colspan="1">1.438 (2)</td>
<td rowspan="1" colspan="1">C20—H20</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C10</td>
<td rowspan="1" colspan="1">1.353 (2)</td>
<td rowspan="1" colspan="1">C21—C22</td>
<td rowspan="1" colspan="1">1.386 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—H9</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C21—H21</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C11</td>
<td rowspan="1" colspan="1">1.408 (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"></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">C15—N1—C16</td>
<td rowspan="1" colspan="1">114.67 (10)</td>
<td rowspan="1" colspan="1">C11—C12—C13</td>
<td rowspan="1" colspan="1">121.55 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15—N1—H1A</td>
<td rowspan="1" colspan="1">112.3 (10)</td>
<td rowspan="1" colspan="1">C11—C12—H12</td>
<td rowspan="1" colspan="1">119.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C16—N1—H1A</td>
<td rowspan="1" colspan="1">106.5 (10)</td>
<td rowspan="1" colspan="1">C13—C12—H12</td>
<td rowspan="1" colspan="1">119.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C15—N1—H1B</td>
<td rowspan="1" colspan="1">109.8 (9)</td>
<td rowspan="1" colspan="1">C14—C13—C12</td>
<td rowspan="1" colspan="1">123.26 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16—N1—H1B</td>
<td rowspan="1" colspan="1">106.0 (9)</td>
<td rowspan="1" colspan="1">C14—C13—C8</td>
<td rowspan="1" colspan="1">119.31 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">H1A—N1—H1B</td>
<td rowspan="1" colspan="1">107.2 (9)</td>
<td rowspan="1" colspan="1">C12—C13—C8</td>
<td rowspan="1" colspan="1">117.42 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14—C1—C2</td>
<td rowspan="1" colspan="1">123.40 (14)</td>
<td rowspan="1" colspan="1">C1—C14—C13</td>
<td rowspan="1" colspan="1">120.77 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14—C1—C6</td>
<td rowspan="1" colspan="1">118.93 (14)</td>
<td rowspan="1" colspan="1">C1—C14—C15</td>
<td rowspan="1" colspan="1">120.96 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6</td>
<td rowspan="1" colspan="1">117.67 (14)</td>
<td rowspan="1" colspan="1">C13—C14—C15</td>
<td rowspan="1" colspan="1">118.23 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—C1</td>
<td rowspan="1" colspan="1">120.89 (16)</td>
<td rowspan="1" colspan="1">N1—C15—C14</td>
<td rowspan="1" colspan="1">112.01 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—H2</td>
<td rowspan="1" colspan="1">119.6</td>
<td rowspan="1" colspan="1">N1—C15—H15A</td>
<td rowspan="1" colspan="1">109.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—H2</td>
<td rowspan="1" colspan="1">119.6</td>
<td rowspan="1" colspan="1">C14—C15—H15A</td>
<td rowspan="1" colspan="1">109.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4</td>
<td rowspan="1" colspan="1">121.11 (16)</td>
<td rowspan="1" colspan="1">N1—C15—H15B</td>
<td rowspan="1" colspan="1">109.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3</td>
<td rowspan="1" colspan="1">119.4</td>
<td rowspan="1" colspan="1">C14—C15—H15B</td>
<td rowspan="1" colspan="1">109.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3</td>
<td rowspan="1" colspan="1">119.4</td>
<td rowspan="1" colspan="1">H15A—C15—H15B</td>
<td rowspan="1" colspan="1">107.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—C3</td>
<td rowspan="1" colspan="1">120.06 (16)</td>
<td rowspan="1" colspan="1">N1—C16—C17</td>
<td rowspan="1" colspan="1">111.53 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—H4</td>
<td rowspan="1" colspan="1">120.0</td>
<td rowspan="1" colspan="1">N1—C16—H16A</td>
<td rowspan="1" colspan="1">109.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4</td>
<td rowspan="1" colspan="1">120.0</td>
<td rowspan="1" colspan="1">C17—C16—H16A</td>
<td rowspan="1" colspan="1">109.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6</td>
<td rowspan="1" colspan="1">121.12 (16)</td>
<td rowspan="1" colspan="1">N1—C16—H16B</td>
<td rowspan="1" colspan="1">109.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—H5</td>
<td rowspan="1" colspan="1">119.4</td>
<td rowspan="1" colspan="1">C17—C16—H16B</td>
<td rowspan="1" colspan="1">109.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—H5</td>
<td rowspan="1" colspan="1">119.4</td>
<td rowspan="1" colspan="1">H16A—C16—H16B</td>
<td rowspan="1" colspan="1">108.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C6—C5</td>
<td rowspan="1" colspan="1">121.68 (15)</td>
<td rowspan="1" colspan="1">C22—C17—C18</td>
<td rowspan="1" colspan="1">119.11 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C6—C1</td>
<td rowspan="1" colspan="1">119.21 (15)</td>
<td rowspan="1" colspan="1">C22—C17—C16</td>
<td rowspan="1" colspan="1">120.99 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—C1</td>
<td rowspan="1" colspan="1">119.11 (15)</td>
<td rowspan="1" colspan="1">C18—C17—C16</td>
<td rowspan="1" colspan="1">119.88 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C7—C6</td>
<td rowspan="1" colspan="1">122.54 (15)</td>
<td rowspan="1" colspan="1">C19—C18—C17</td>
<td rowspan="1" colspan="1">120.05 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C7—H7</td>
<td rowspan="1" colspan="1">118.7</td>
<td rowspan="1" colspan="1">C19—C18—H18</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C7—H7</td>
<td rowspan="1" colspan="1">118.7</td>
<td rowspan="1" colspan="1">C17—C18—H18</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8—C9</td>
<td rowspan="1" colspan="1">122.15 (15)</td>
<td rowspan="1" colspan="1">C20—C19—C18</td>
<td rowspan="1" colspan="1">120.37 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8—C13</td>
<td rowspan="1" colspan="1">119.11 (14)</td>
<td rowspan="1" colspan="1">C20—C19—H19</td>
<td rowspan="1" colspan="1">119.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C8—C13</td>
<td rowspan="1" colspan="1">118.74 (15)</td>
<td rowspan="1" colspan="1">C18—C19—H19</td>
<td rowspan="1" colspan="1">119.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C9—C8</td>
<td rowspan="1" colspan="1">121.28 (16)</td>
<td rowspan="1" colspan="1">C19—C20—C21</td>
<td rowspan="1" colspan="1">120.05 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C9—H9</td>
<td rowspan="1" colspan="1">119.4</td>
<td rowspan="1" colspan="1">C19—C20—H20</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C9—H9</td>
<td rowspan="1" colspan="1">119.4</td>
<td rowspan="1" colspan="1">C21—C20—H20</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C10—C11</td>
<td rowspan="1" colspan="1">120.10 (15)</td>
<td rowspan="1" colspan="1">C22—C21—C20</td>
<td rowspan="1" colspan="1">119.72 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C10—H10</td>
<td rowspan="1" colspan="1">119.9</td>
<td rowspan="1" colspan="1">C22—C21—H21</td>
<td rowspan="1" colspan="1">120.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C10—H10</td>
<td rowspan="1" colspan="1">119.9</td>
<td rowspan="1" colspan="1">C20—C21—H21</td>
<td rowspan="1" colspan="1">120.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C12—C11—C10</td>
<td rowspan="1" colspan="1">120.87 (16)</td>
<td rowspan="1" colspan="1">C17—C22—C21</td>
<td rowspan="1" colspan="1">120.71 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12—C11—H11</td>
<td rowspan="1" colspan="1">119.6</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">C10—C11—H11</td>
<td rowspan="1" colspan="1">119.6</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"></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">C14—C1—C2—C3</td>
<td rowspan="1" colspan="1">−177.07 (13)</td>
<td rowspan="1" colspan="1">C7—C8—C13—C12</td>
<td rowspan="1" colspan="1">178.28 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td>
<td rowspan="1" colspan="1">1.8 (2)</td>
<td rowspan="1" colspan="1">C9—C8—C13—C12</td>
<td rowspan="1" colspan="1">−1.57 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td>
<td rowspan="1" colspan="1">−0.1 (2)</td>
<td rowspan="1" colspan="1">C2—C1—C14—C13</td>
<td rowspan="1" colspan="1">−178.15 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td>
<td rowspan="1" colspan="1">−0.9 (2)</td>
<td rowspan="1" colspan="1">C6—C1—C14—C13</td>
<td rowspan="1" colspan="1">3.01 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td>
<td rowspan="1" colspan="1">0.2 (2)</td>
<td rowspan="1" colspan="1">C2—C1—C14—C15</td>
<td rowspan="1" colspan="1">4.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6—C7</td>
<td rowspan="1" colspan="1">−178.11 (14)</td>
<td rowspan="1" colspan="1">C6—C1—C14—C15</td>
<td rowspan="1" colspan="1">−174.63 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td>
<td rowspan="1" colspan="1">1.5 (2)</td>
<td rowspan="1" colspan="1">C12—C13—C14—C1</td>
<td rowspan="1" colspan="1">179.28 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14—C1—C6—C7</td>
<td rowspan="1" colspan="1">−3.89 (19)</td>
<td rowspan="1" colspan="1">C8—C13—C14—C1</td>
<td rowspan="1" colspan="1">0.21 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—C7</td>
<td rowspan="1" colspan="1">177.20 (12)</td>
<td rowspan="1" colspan="1">C12—C13—C14—C15</td>
<td rowspan="1" colspan="1">−3.02 (19)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14—C1—C6—C5</td>
<td rowspan="1" colspan="1">176.47 (12)</td>
<td rowspan="1" colspan="1">C8—C13—C14—C15</td>
<td rowspan="1" colspan="1">177.92 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td>
<td rowspan="1" colspan="1">−2.44 (19)</td>
<td rowspan="1" colspan="1">C16—N1—C15—C14</td>
<td rowspan="1" colspan="1">−170.73 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—C7—C8</td>
<td rowspan="1" colspan="1">−178.83 (13)</td>
<td rowspan="1" colspan="1">C1—C14—C15—N1</td>
<td rowspan="1" colspan="1">−106.13 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—C7—C8</td>
<td rowspan="1" colspan="1">1.5 (2)</td>
<td rowspan="1" colspan="1">C13—C14—C15—N1</td>
<td rowspan="1" colspan="1">76.17 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C7—C8—C9</td>
<td rowspan="1" colspan="1">−178.44 (13)</td>
<td rowspan="1" colspan="1">C15—N1—C16—C17</td>
<td rowspan="1" colspan="1">52.24 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C7—C8—C13</td>
<td rowspan="1" colspan="1">1.7 (2)</td>
<td rowspan="1" colspan="1">N1—C16—C17—C22</td>
<td rowspan="1" colspan="1">81.05 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8—C9—C10</td>
<td rowspan="1" colspan="1">−179.48 (14)</td>
<td rowspan="1" colspan="1">N1—C16—C17—C18</td>
<td rowspan="1" colspan="1">−97.18 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13—C8—C9—C10</td>
<td rowspan="1" colspan="1">0.4 (2)</td>
<td rowspan="1" colspan="1">C22—C17—C18—C19</td>
<td rowspan="1" colspan="1">−0.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C9—C10—C11</td>
<td rowspan="1" colspan="1">0.6 (2)</td>
<td rowspan="1" colspan="1">C16—C17—C18—C19</td>
<td rowspan="1" colspan="1">177.52 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C10—C11—C12</td>
<td rowspan="1" colspan="1">−0.4 (2)</td>
<td rowspan="1" colspan="1">C17—C18—C19—C20</td>
<td rowspan="1" colspan="1">0.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C11—C12—C13</td>
<td rowspan="1" colspan="1">−0.9 (2)</td>
<td rowspan="1" colspan="1">C18—C19—C20—C21</td>
<td rowspan="1" colspan="1">−0.1 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C12—C13—C14</td>
<td rowspan="1" colspan="1">−177.20 (13)</td>
<td rowspan="1" colspan="1">C19—C20—C21—C22</td>
<td rowspan="1" colspan="1">−0.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C12—C13—C8</td>
<td rowspan="1" colspan="1">1.9 (2)</td>
<td rowspan="1" colspan="1">C18—C17—C22—C21</td>
<td rowspan="1" colspan="1">0.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8—C13—C14</td>
<td rowspan="1" colspan="1">−2.6 (2)</td>
<td rowspan="1" colspan="1">C16—C17—C22—C21</td>
<td rowspan="1" colspan="1">−177.76 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C8—C13—C14</td>
<td rowspan="1" colspan="1">177.55 (11)</td>
<td rowspan="1" colspan="1">C20—C21—C22—C17</td>
<td rowspan="1" colspan="1">0.0 (2)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title>
<table-wrap position="anchor" id="d1e2534"><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">N1—H1A···Cl1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.92 (1)</td>
<td rowspan="1" colspan="1">2.26 (1)</td>
<td rowspan="1" colspan="1">3.0963 (13)</td>
<td rowspan="1" colspan="1">152 (1)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1B···Cl1</td>
<td rowspan="1" colspan="1">0.92 (1)</td>
<td rowspan="1" colspan="1">2.17 (1)</td>
<td rowspan="1" colspan="1">3.0781 (16)</td>
<td rowspan="1" colspan="1">170 (1)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16—H16A···Cl1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.97</td>
<td rowspan="1" colspan="1">2.60</td>
<td rowspan="1" colspan="1">3.4824 (16)</td>
<td rowspan="1" colspan="1">151</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) −<italic>x</italic>
+1, −<italic>y</italic>
+1, −<italic>z</italic>
+1; (ii) −<italic>x</italic>
, −<italic>y</italic>
+1, −<italic>z</italic>
+1.</p>
</sec>
</app>
</app-group>
<ref-list><title>References</title>
<ref id="bb1"><mixed-citation publication-type="other">Ashton, P. R., Ballardini, R., Balzani, V., Marcos, G.-L., Lawrence, S. M., Victoria, M.-D., Montalti, M., Piersanti, A., Prodi, L., Stoddart, J. F. & Williams, D. (1997). <italic>J. Am. Chem. Soc.</italic> 
               <bold>119</bold>
, 10641–10651.</mixed-citation>
</ref>
<ref id="bb2"><mixed-citation publication-type="other">Nakazono, K., Kuwata, S. & Takata, T. (2008). <italic>Tetrahedron Lett.</italic> 
               <bold>49</bold>
, 2397–2400.</mixed-citation>
</ref>
<ref id="bb3"><mixed-citation publication-type="other">Rigaku/MSC (2005). <italic>CrystalClear</italic>
 Rigaku/MSC Inc., The Woodlands, Texas, USA.</mixed-citation>
</ref>
<ref id="bb4"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic>
 A<bold>64</bold>
, 112–122.</mixed-citation>
</ref>
</ref-list>
</back>
<floats-group><table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (Å, °)</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>A</italic>
⋯Cl1<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.92 (1)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.26 (1)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.0963 (13)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">152 (1)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>B</italic>
⋯Cl1</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.92 (1)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.17 (1)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.0781 (16)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">170 (1)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C16—H16<italic>A</italic>
⋯Cl1<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.97</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.60</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.4824 (16)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">151</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-67-o1482-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-67-o1482-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>

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(Anthracen-9-ylmeth­yl)benzyl­ammonium chloride

(Anthracen-9-ylmeth­yl)benzyl­ammonium chloride

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(Anthracen-9-ylmethyl)benzylammonium chloride

(Anthracen-9-ylmethyl)benzylammonium chloride