N-(4-Hydroxyphenethyl)acetamide
Identifieur interne : 000A15 ( Pmc/Corpus ); précédent : 000A14; suivant : 000A16N-(4-Hydroxyphenethyl)acetamide
Auteurs : Bo Wang ; Yun Chai ; Peizhen Tao ; Mingliang LiuSource :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2009.
Abstract
In the title compound, C10H13NO2, the occurrence of intermolecular N—H⋯O and O—H⋯O hydrogen bonds between the hydroxy and acetamido groups results in the formation of tetramers with an
Url:
DOI: 10.1107/S1600536809025409
PubMed: 21583495
PubMed Central: 2977160
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PMC:2977160Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en"><italic>N</italic>
-(4-Hydroxyphenethyl)acetamide</title>
<author><name sortKey="Wang, Bo" sort="Wang, Bo" uniqKey="Wang B" first="Bo" last="Wang">Bo Wang</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Chai, Yun" sort="Chai, Yun" uniqKey="Chai Y" first="Yun" last="Chai">Yun Chai</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tao, Peizhen" sort="Tao, Peizhen" uniqKey="Tao P" first="Peizhen" last="Tao">Peizhen Tao</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Liu, Mingliang" sort="Liu, Mingliang" uniqKey="Liu M" first="Mingliang" last="Liu">Mingliang Liu</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">21583495</idno>
<idno type="pmc">2977160</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977160</idno>
<idno type="RBID">PMC:2977160</idno>
<idno type="doi">10.1107/S1600536809025409</idno>
<date when="2009">2009</date>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main"><italic>N</italic>
-(4-Hydroxyphenethyl)acetamide</title>
<author><name sortKey="Wang, Bo" sort="Wang, Bo" uniqKey="Wang B" first="Bo" last="Wang">Bo Wang</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Chai, Yun" sort="Chai, Yun" uniqKey="Chai Y" first="Yun" last="Chai">Yun Chai</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tao, Peizhen" sort="Tao, Peizhen" uniqKey="Tao P" first="Peizhen" last="Tao">Peizhen Tao</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Liu, Mingliang" sort="Liu, Mingliang" uniqKey="Liu M" first="Mingliang" last="Liu">Mingliang Liu</name>
<affiliation><nlm:aff id="a">Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<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="2009">2009</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>13</sub>
NO<sub>2</sub>
, the occurrence of intermolecular N—H⋯O and O—H⋯O hydrogen bonds between the hydroxy and acetamido groups results in the formation of tetramers with an <italic>R</italic>
<sub>4</sub>
<sup>4</sup>
(25) graph-set motif. These tetramers are further assembled, building up a corrugated sheet parallel to (001).</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
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</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr 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">21583495</article-id>
<article-id pub-id-type="pmc">2977160</article-id>
<article-id pub-id-type="publisher-id">dn2469</article-id>
<article-id pub-id-type="doi">10.1107/S1600536809025409</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536809025409</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title><italic>N</italic>
-(4-Hydroxyphenethyl)acetamide</article-title>
<alt-title><italic>C<sub>10</sub>
H<sub>13</sub>
NO<sub>2</sub>
</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Wang</surname>
<given-names>Bo</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Chai</surname>
<given-names>Yun</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Tao</surname>
<given-names>Peizhen</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Liu</surname>
<given-names>Mingliang</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<aff id="a"><label>a</label>
Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050,<country>People’s Republic of China</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>lmllyx@yahoo.com.cn</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>8</month>
<year>2009</year>
</pub-date>
<pub-date pub-type="epub"><day>08</day>
<month>7</month>
<year>2009</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>08</day>
<month>7</month>
<year>2009</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
. </pmc-comment>
<volume>65</volume>
<issue>Pt 8</issue>
<issue-id pub-id-type="publisher-id">e090800</issue-id>
<fpage>o1789</fpage>
<lpage>o1789</lpage>
<history><date date-type="received"><day>22</day>
<month>6</month>
<year>2009</year>
</date>
<date date-type="accepted"><day>01</day>
<month>7</month>
<year>2009</year>
</date>
</history>
<permissions><copyright-statement>© Wang et al. 2009</copyright-statement>
<copyright-year>2009</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/S1600536809025409">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>13</sub>
NO<sub>2</sub>
, the occurrence of intermolecular N—H⋯O and O—H⋯O hydrogen bonds between the hydroxy and acetamido groups results in the formation of tetramers with an <italic>R</italic>
<sub>4</sub>
<sup>4</sup>
(25) graph-set motif. These tetramers are further assembled, building up a corrugated sheet parallel to (001).</p>
</abstract>
</article-meta>
</front>
<body><sec id="sec1"><title>Related literature</title>
<p>For the biological activity of <italic>N</italic>
-(4-hydroxyphenethyl)acetamide, see: Garcez <italic>et al.</italic>
(2000<xref ref-type="bibr" rid="bb9"> ▶</xref>
); Montedoro <italic>et al.</italic>
(1993<xref ref-type="bibr" rid="bb10"> ▶</xref>
). For related structures, see: Chai <italic>et al.</italic>
(2009<xref ref-type="bibr" rid="bb6"> ▶</xref>
); Song <italic>et al.</italic>
(2008<xref ref-type="bibr" rid="bb13"> ▶</xref>
). For bond-length data, see: Allen <italic>et al.</italic>
(1987<xref ref-type="bibr" rid="bb1"> ▶</xref>
). For hydrogen-bond motifs, see: Bernstein <italic>et al.</italic>
(1995<xref ref-type="bibr" rid="bb2"> ▶</xref>
); Etter (1990<xref ref-type="bibr" rid="bb7"> ▶</xref>
)<chem-struct id="scheme1"><graphic xlink:href="e-65-o1789-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>13</sub>
NO<sub>2</sub>
</p>
</list-item>
<list-item><p><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 179.21</p>
</list-item>
<list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-65-o1789-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</p>
</list-item>
<list-item><p><italic>a</italic>
= 9.9206 (13) Å</p>
</list-item>
<list-item><p><italic>b</italic>
= 8.7861 (11) Å</p>
</list-item>
<list-item><p><italic>c</italic>
= 11.4943 (16) Å</p>
</list-item>
<list-item><p>β = 102.9980 (10)°</p>
</list-item>
<list-item><p><italic>V</italic>
= 976.2 (2) 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 = 0.09 mm<sup>−1</sup>
</p>
</list-item>
<list-item><p><italic>T</italic>
= 298 K</p>
</list-item>
<list-item><p>0.43 × 0.38 × 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>Bruker SMART CCD diffractometer</p>
</list-item>
<list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>
; Sheldrick, 2008<italic>a</italic>
<xref ref-type="bibr" rid="bb14"> ▶</xref>
) <italic>T</italic>
<sub>min</sub>
= 0.961, <italic>T</italic>
<sub>max</sub>
= 0.978</p>
</list-item>
<list-item><p>4753 measured reflections</p>
</list-item>
<list-item><p>1713 independent reflections</p>
</list-item>
<list-item><p>1196 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>
)] = 0.037</p>
</list-item>
<list-item><p><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.100</p>
</list-item>
<list-item><p><italic>S</italic>
= 1.05</p>
</list-item>
<list-item><p>1713 reflections</p>
</list-item>
<list-item><p>119 parameters</p>
</list-item>
<list-item><p>H-atom parameters constrained</p>
</list-item>
<list-item><p>Δρ<sub>max</sub>
= 0.16 e Å<sup>−3</sup>
</p>
</list-item>
<list-item><p>Δρ<sub>min</sub>
= −0.14 e Å<sup>−3</sup>
</p>
</list-item>
</list>
</p>
</sec>
</sec>
<sec id="d5e447"><title></title>
<p>Data collection: <italic>SMART</italic>
(Bruker, 1998<xref ref-type="bibr" rid="bb3"> ▶</xref>
); cell refinement: <italic>SAINT</italic>
(Bruker, 1999<xref ref-type="bibr" rid="bb4"> ▶</xref>
); data reduction: <italic>SAINT</italic>
; program(s) used to solve structure: <italic>SHELXS97</italic>
(Sheldrick, 2008<italic>b</italic>
<xref ref-type="bibr" rid="bb12"> ▶</xref>
); program(s) used to refine structure: <italic>SHELXL97</italic>
(Sheldrick, 2008<italic>b</italic>
<xref ref-type="bibr" rid="bb12"> ▶</xref>
); molecular graphics: <italic>ORTEPIII</italic>
(Burnett & Johnson, 1996<xref ref-type="bibr" rid="bb5"> ▶</xref>
), <italic>ORTEP-3 for Windows</italic>
(Farrugia, 1997<xref ref-type="bibr" rid="bb8"> ▶</xref>
) and <italic>CAMERON</italic>
(Pearce <italic>et al.</italic>
, 2000<xref ref-type="bibr" rid="bb11"> ▶</xref>
); software used to prepare material for publication: <italic>SHELXTL</italic>
(Sheldrick, 2008<italic>b</italic>
<xref ref-type="bibr" rid="bb12"> ▶</xref>
).</p>
</sec>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data" xlink:href="e-65-o1789-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/S1600536809025409/dn2469sup1.cif">10.1107/S1600536809025409/dn2469sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-65-o1789-sup1.cif" position="float" xlink:type="simple"></media>
</supplementary-material>
<supplementary-material content-type="local-data" xlink:href="e-65-o1789-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/S1600536809025409/dn2469Isup2.hkl">10.1107/S1600536809025409/dn2469Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-65-o1789-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?dn2469&file=dn2469sup0.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?dn2469sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?dn2469&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?dn2469">DN2469</ext-link>
).</p>
</fn>
</fn-group>
<ack><p>This work was supported by the IMB Research Foundation. The authors thank Dr Daqi Wang for useful discussions.</p>
</ack>
<app-group><app><title>supplementary crystallographic
information</title>
<sec id="comment"><title>Comment </title>
<p><italic>N</italic>
-(4-Hydroxyphenethyl)acetamide displays various biological activities
(Garcez <italic>et al.</italic>
, 2000; Montedoro <italic>et al.</italic>
, 1993;
Allen <italic>et
al.</italic>
, 1987), we report herein the crystal structure of the title
compound.</p>
<p>In the molecule of the title compound (Fig 1), all of the bond lengths and
angles are within normal ranges. the occurrence of intermolecular N–H···O and
O–H···O hydrogen bonds between the hydroxy and acetamido groups results in
the formation of tetramers with a <italic>R</italic>
<sub>4</sub>
<sup>4</sup>
(25) graph set motif (Etter,
1990; Bernstein <italic>et al.</italic>
, 1995). These tetrameric motifs
are further
assemble to build up a corrugated sheet parallel to the (0 0 1) plane (Table
1, Fig. 2).</p>
<p>The bond lengths and bond angles agree with the values observed in related
structures (Chai <italic>et al.</italic>
, 2009; Song <italic>et al.</italic>
,
2008).</p>
</sec>
<sec id="experimental"><title>Experimental </title>
<p>The title compound was separated from fermentation liquor as a white solid.
Single crystals suitable for X-ray analysis were obtained by slow evaporation
of a methanol/water solution(2:1 <italic>v</italic>
/<italic>v</italic>
). <sup>1</sup>
H NMR (DMSO-d<sub>6</sub>
, δ):
9.14 (1<italic>H</italic>
, s, OH), 7.84 (1<italic>H</italic>
, br, NH), 6.96 (2<italic>H</italic>
, d,
PhH<sub>2</sub>
), 6.66 (2<italic>H</italic>
, d, PhH<sub>2</sub>
), 3.14–3.19 (2<italic>H</italic>
, m, CH<sub>2</sub>
),
2.49–2.57 (2<italic>H</italic>
, m, CH<sub>2</sub>
), 1.77 (3<italic>H</italic>
, s, CH<sub>3</sub>
). MS(FAB,
m/<italic>z</italic>
): 180 (<italic>M</italic>
+H)<sup>+</sup>
.</p>
</sec>
<sec id="refinement"><title>Refinement </title>
<p>All H atom were placed at calculated positions, with C—H = 0.96–0.97 Å and
N—H = 0.86 Å, and were included in the final cycles of refinement using a
riding model, with <italic>U</italic>
<sub>iso</sub>
(H) = 1.2 <italic>U</italic>
<sub>eq</sub>
(C,<italic>N</italic>
) or 1.5
<italic>U</italic>
<sub>eq</sub>
(methyl C). The H of the methyl group were statistically
disordered over two positions.</p>
</sec>
<sec id="figures"><title>Figures</title>
<fig id="Fap1"><label>Fig. 1.</label>
<caption><p>Molecular structure of (I) with the atos labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are rpresented as small spheres of arbitrary radii.</p>
</caption>
<graphic xlink:href="e-65-o1789-fig1"></graphic>
</fig>
<fig id="Fap2"><label>Fig. 2.</label>
<caption><p>Partial packing view showing the corrugated sheet and the R44(25) graph set motif.</p>
</caption>
<graphic xlink:href="e-65-o1789-fig2"></graphic>
</fig>
</sec>
<sec id="tablewrapcrystaldatalong"><title>Crystal data</title>
<table-wrap position="anchor" id="d1e214"><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>13</sub>
NO<sub>2</sub>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 384</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 179.21</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
= 1.219 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1">Hall symbol: -P 2ybc</td>
<td rowspan="1" colspan="1">Cell parameters from 1622 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
= 9.9206 (13) Å</td>
<td rowspan="1" colspan="1">θ = 3.0–26.2°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
= 8.7861 (11) Å</td>
<td rowspan="1" colspan="1">µ = 0.09 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
= 11.4943 (16) Å</td>
<td rowspan="1" colspan="1"><italic>T</italic>
= 298 K</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 102.998 (1)°</td>
<td rowspan="1" colspan="1">Block, colorless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
= 976.2 (2) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.43 × 0.38 × 0.20 mm</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
= 4</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapdatacollectionlong"><title>Data collection</title>
<table-wrap position="anchor" id="d1e341"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Bruker SMART CCD diffractometer</td>
<td rowspan="1" colspan="1">1713 independent reflections</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td>
<td rowspan="1" colspan="1">1196 reflections with <italic>I</italic>
> 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">graphite</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
= 0.027</td>
</tr>
<tr><td rowspan="1" colspan="1">φ and ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
= 25.0°, θ<sub>min</sub>
= 2.1°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>
; Sheldrick, 2008)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
= −7→11</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
= 0.961, <italic>T</italic>
<sub>max</sub>
= 0.978</td>
<td rowspan="1" colspan="1"><italic>k</italic>
= −9→10</td>
</tr>
<tr><td rowspan="1" colspan="1">4753 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
= −13→13</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewraprefinementdatalong"><title>Refinement</title>
<table-wrap position="anchor" id="d1e458"><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>
)] = 0.037</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>
) = 0.100</td>
<td rowspan="1" colspan="1">H-atom parameters constrained</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
= 1.05</td>
<td rowspan="1" colspan="1"><italic>w</italic>
= 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0387<italic>P</italic>
)<sup>2</sup>
+ 0.1837<italic>P</italic>
] where <italic>P</italic>
= (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
+ 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1">1713 reflections</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
< 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1">119 parameters</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
= 0.16 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>
= −0.14 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="specialdetails"><title>Special details</title>
<table-wrap position="anchor" id="d1e615"><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="d1e714"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1">Occ. (<1)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.15094 (14)</td>
<td rowspan="1" colspan="1">0.38049 (16)</td>
<td rowspan="1" colspan="1">0.35383 (14)</td>
<td rowspan="1" colspan="1">0.0553 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1</td>
<td rowspan="1" colspan="1">0.1936</td>
<td rowspan="1" colspan="1">0.4303</td>
<td rowspan="1" colspan="1">0.3086</td>
<td rowspan="1" colspan="1">0.066*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.72697 (12)</td>
<td rowspan="1" colspan="1">0.10975 (15)</td>
<td rowspan="1" colspan="1">0.27285 (11)</td>
<td rowspan="1" colspan="1">0.0598 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H1A</td>
<td rowspan="1" colspan="1">0.7957</td>
<td rowspan="1" colspan="1">0.1586</td>
<td rowspan="1" colspan="1">0.3049</td>
<td rowspan="1" colspan="1">0.090*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">−0.04072 (13)</td>
<td rowspan="1" colspan="1">0.25522 (17)</td>
<td rowspan="1" colspan="1">0.36772 (12)</td>
<td rowspan="1" colspan="1">0.0724 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.40477 (16)</td>
<td rowspan="1" colspan="1">0.18477 (19)</td>
<td rowspan="1" colspan="1">0.44391 (14)</td>
<td rowspan="1" colspan="1">0.0444 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.39022 (17)</td>
<td rowspan="1" colspan="1">0.09127 (19)</td>
<td rowspan="1" colspan="1">0.34533 (15)</td>
<td rowspan="1" colspan="1">0.0516 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H2</td>
<td rowspan="1" colspan="1">0.3057</td>
<td rowspan="1" colspan="1">0.0435</td>
<td rowspan="1" colspan="1">0.3162</td>
<td rowspan="1" colspan="1">0.062*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.49703 (18)</td>
<td rowspan="1" colspan="1">0.0664 (2)</td>
<td rowspan="1" colspan="1">0.28865 (16)</td>
<td rowspan="1" colspan="1">0.0516 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H3</td>
<td rowspan="1" colspan="1">0.4843</td>
<td rowspan="1" colspan="1">0.0024</td>
<td rowspan="1" colspan="1">0.2226</td>
<td rowspan="1" colspan="1">0.062*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.62273 (16)</td>
<td rowspan="1" colspan="1">0.13710 (18)</td>
<td rowspan="1" colspan="1">0.33044 (14)</td>
<td rowspan="1" colspan="1">0.0430 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.64007 (17)</td>
<td rowspan="1" colspan="1">0.23153 (18)</td>
<td rowspan="1" colspan="1">0.42830 (14)</td>
<td rowspan="1" colspan="1">0.0462 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H5</td>
<td rowspan="1" colspan="1">0.7244</td>
<td rowspan="1" colspan="1">0.2800</td>
<td rowspan="1" colspan="1">0.4568</td>
<td rowspan="1" colspan="1">0.055*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.53229 (17)</td>
<td rowspan="1" colspan="1">0.25403 (19)</td>
<td rowspan="1" colspan="1">0.48397 (15)</td>
<td rowspan="1" colspan="1">0.0493 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H6</td>
<td rowspan="1" colspan="1">0.5455</td>
<td rowspan="1" colspan="1">0.3175</td>
<td rowspan="1" colspan="1">0.5503</td>
<td rowspan="1" colspan="1">0.059*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.28890 (18)</td>
<td rowspan="1" colspan="1">0.2102 (2)</td>
<td rowspan="1" colspan="1">0.50690 (16)</td>
<td rowspan="1" colspan="1">0.0542 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7A</td>
<td rowspan="1" colspan="1">0.3257</td>
<td rowspan="1" colspan="1">0.2034</td>
<td rowspan="1" colspan="1">0.5924</td>
<td rowspan="1" colspan="1">0.065*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7B</td>
<td rowspan="1" colspan="1">0.2210</td>
<td rowspan="1" colspan="1">0.1299</td>
<td rowspan="1" colspan="1">0.4845</td>
<td rowspan="1" colspan="1">0.065*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.21757 (18)</td>
<td rowspan="1" colspan="1">0.3629 (2)</td>
<td rowspan="1" colspan="1">0.47851 (17)</td>
<td rowspan="1" colspan="1">0.0562 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.1488</td>
<td rowspan="1" colspan="1">0.3745</td>
<td rowspan="1" colspan="1">0.5260</td>
<td rowspan="1" colspan="1">0.067*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8B</td>
<td rowspan="1" colspan="1">0.2854</td>
<td rowspan="1" colspan="1">0.4434</td>
<td rowspan="1" colspan="1">0.5012</td>
<td rowspan="1" colspan="1">0.067*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.02736 (18)</td>
<td rowspan="1" colspan="1">0.3236 (2)</td>
<td rowspan="1" colspan="1">0.30588 (17)</td>
<td rowspan="1" colspan="1">0.0545 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">−0.0253 (2)</td>
<td rowspan="1" colspan="1">0.3440 (3)</td>
<td rowspan="1" colspan="1">0.17442 (18)</td>
<td rowspan="1" colspan="1">0.0790 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.0416</td>
<td rowspan="1" colspan="1">0.3994</td>
<td rowspan="1" colspan="1">0.1425</td>
<td rowspan="1" colspan="1">0.119*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">H10B</td>
<td rowspan="1" colspan="1">−0.1108</td>
<td rowspan="1" colspan="1">0.3995</td>
<td rowspan="1" colspan="1">0.1597</td>
<td rowspan="1" colspan="1">0.119*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">H10C</td>
<td rowspan="1" colspan="1">−0.0404</td>
<td rowspan="1" colspan="1">0.2461</td>
<td rowspan="1" colspan="1">0.1366</td>
<td rowspan="1" colspan="1">0.119*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">H10D</td>
<td rowspan="1" colspan="1">−0.1146</td>
<td rowspan="1" colspan="1">0.2973</td>
<td rowspan="1" colspan="1">0.1501</td>
<td rowspan="1" colspan="1">0.119*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">H10E</td>
<td rowspan="1" colspan="1">0.0377</td>
<td rowspan="1" colspan="1">0.2972</td>
<td rowspan="1" colspan="1">0.1329</td>
<td rowspan="1" colspan="1">0.119*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
<tr><td rowspan="1" colspan="1">H10F</td>
<td rowspan="1" colspan="1">−0.0326</td>
<td rowspan="1" colspan="1">0.4506</td>
<td rowspan="1" colspan="1">0.1559</td>
<td rowspan="1" colspan="1">0.119*</td>
<td rowspan="1" colspan="1">0.50</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e1119"><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">N1</td>
<td rowspan="1" colspan="1">0.0394 (8)</td>
<td rowspan="1" colspan="1">0.0592 (9)</td>
<td rowspan="1" colspan="1">0.0710 (10)</td>
<td rowspan="1" colspan="1">0.0001 (7)</td>
<td rowspan="1" colspan="1">0.0200 (7)</td>
<td rowspan="1" colspan="1">0.0143 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0472 (7)</td>
<td rowspan="1" colspan="1">0.0672 (9)</td>
<td rowspan="1" colspan="1">0.0692 (9)</td>
<td rowspan="1" colspan="1">−0.0047 (6)</td>
<td rowspan="1" colspan="1">0.0223 (6)</td>
<td rowspan="1" colspan="1">−0.0153 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0500 (8)</td>
<td rowspan="1" colspan="1">0.0981 (11)</td>
<td rowspan="1" colspan="1">0.0736 (9)</td>
<td rowspan="1" colspan="1">−0.0201 (7)</td>
<td rowspan="1" colspan="1">0.0232 (7)</td>
<td rowspan="1" colspan="1">0.0017 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0399 (9)</td>
<td rowspan="1" colspan="1">0.0478 (9)</td>
<td rowspan="1" colspan="1">0.0461 (10)</td>
<td rowspan="1" colspan="1">0.0014 (8)</td>
<td rowspan="1" colspan="1">0.0112 (7)</td>
<td rowspan="1" colspan="1">0.0084 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0393 (10)</td>
<td rowspan="1" colspan="1">0.0572 (11)</td>
<td rowspan="1" colspan="1">0.0565 (11)</td>
<td rowspan="1" colspan="1">−0.0115 (8)</td>
<td rowspan="1" colspan="1">0.0069 (8)</td>
<td rowspan="1" colspan="1">0.0006 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0503 (10)</td>
<td rowspan="1" colspan="1">0.0547 (11)</td>
<td rowspan="1" colspan="1">0.0492 (10)</td>
<td rowspan="1" colspan="1">−0.0075 (9)</td>
<td rowspan="1" colspan="1">0.0102 (8)</td>
<td rowspan="1" colspan="1">−0.0085 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0383 (9)</td>
<td rowspan="1" colspan="1">0.0445 (9)</td>
<td rowspan="1" colspan="1">0.0473 (10)</td>
<td rowspan="1" colspan="1">0.0017 (7)</td>
<td rowspan="1" colspan="1">0.0119 (7)</td>
<td rowspan="1" colspan="1">0.0022 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0348 (9)</td>
<td rowspan="1" colspan="1">0.0495 (10)</td>
<td rowspan="1" colspan="1">0.0521 (10)</td>
<td rowspan="1" colspan="1">−0.0034 (7)</td>
<td rowspan="1" colspan="1">0.0050 (7)</td>
<td rowspan="1" colspan="1">−0.0044 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0450 (10)</td>
<td rowspan="1" colspan="1">0.0542 (11)</td>
<td rowspan="1" colspan="1">0.0484 (10)</td>
<td rowspan="1" colspan="1">−0.0013 (8)</td>
<td rowspan="1" colspan="1">0.0096 (8)</td>
<td rowspan="1" colspan="1">−0.0073 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0475 (10)</td>
<td rowspan="1" colspan="1">0.0627 (12)</td>
<td rowspan="1" colspan="1">0.0545 (11)</td>
<td rowspan="1" colspan="1">−0.0009 (9)</td>
<td rowspan="1" colspan="1">0.0157 (8)</td>
<td rowspan="1" colspan="1">0.0079 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0439 (10)</td>
<td rowspan="1" colspan="1">0.0601 (12)</td>
<td rowspan="1" colspan="1">0.0682 (12)</td>
<td rowspan="1" colspan="1">−0.0054 (9)</td>
<td rowspan="1" colspan="1">0.0201 (9)</td>
<td rowspan="1" colspan="1">−0.0046 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0422 (10)</td>
<td rowspan="1" colspan="1">0.0601 (11)</td>
<td rowspan="1" colspan="1">0.0651 (12)</td>
<td rowspan="1" colspan="1">0.0080 (9)</td>
<td rowspan="1" colspan="1">0.0202 (9)</td>
<td rowspan="1" colspan="1">0.0039 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0602 (13)</td>
<td rowspan="1" colspan="1">0.1059 (18)</td>
<td rowspan="1" colspan="1">0.0711 (14)</td>
<td rowspan="1" colspan="1">0.0112 (12)</td>
<td rowspan="1" colspan="1">0.0150 (11)</td>
<td rowspan="1" colspan="1">0.0090 (13)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title>
<table-wrap position="anchor" id="d1e1386"><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—C9</td>
<td rowspan="1" colspan="1">1.324 (2)</td>
<td rowspan="1" colspan="1">C5—H5</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C8</td>
<td rowspan="1" colspan="1">1.445 (2)</td>
<td rowspan="1" colspan="1">C6—H6</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—H1</td>
<td rowspan="1" colspan="1">0.8600</td>
<td rowspan="1" colspan="1">C7—C8</td>
<td rowspan="1" colspan="1">1.518 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C4</td>
<td rowspan="1" colspan="1">1.3686 (19)</td>
<td rowspan="1" colspan="1">C7—H7A</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—H1A</td>
<td rowspan="1" colspan="1">0.8200</td>
<td rowspan="1" colspan="1">C7—H7B</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C9</td>
<td rowspan="1" colspan="1">1.240 (2)</td>
<td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2</td>
<td rowspan="1" colspan="1">1.381 (2)</td>
<td rowspan="1" colspan="1">C8—H8B</td>
<td rowspan="1" colspan="1">0.9700</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6</td>
<td rowspan="1" colspan="1">1.386 (2)</td>
<td rowspan="1" colspan="1">C9—C10</td>
<td rowspan="1" colspan="1">1.494 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C7</td>
<td rowspan="1" colspan="1">1.507 (2)</td>
<td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.380 (2)</td>
<td rowspan="1" colspan="1">C10—H10B</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—H2</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C10—H10C</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.379 (2)</td>
<td rowspan="1" colspan="1">C10—H10D</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—H3</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C10—H10E</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.377 (2)</td>
<td rowspan="1" colspan="1">C10—H10F</td>
<td rowspan="1" colspan="1">0.9600</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.378 (2)</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9—N1—C8</td>
<td rowspan="1" colspan="1">123.14 (15)</td>
<td rowspan="1" colspan="1">N1—C8—H8A</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—N1—H1</td>
<td rowspan="1" colspan="1">118.4</td>
<td rowspan="1" colspan="1">C7—C8—H8A</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—N1—H1</td>
<td rowspan="1" colspan="1">118.4</td>
<td rowspan="1" colspan="1">N1—C8—H8B</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—O1—H1A</td>
<td rowspan="1" colspan="1">109.5</td>
<td rowspan="1" colspan="1">C7—C8—H8B</td>
<td rowspan="1" colspan="1">108.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C6</td>
<td rowspan="1" colspan="1">116.94 (15)</td>
<td rowspan="1" colspan="1">H8A—C8—H8B</td>
<td rowspan="1" colspan="1">107.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C1—C7</td>
<td rowspan="1" colspan="1">122.18 (15)</td>
<td rowspan="1" colspan="1">O2—C9—N1</td>
<td rowspan="1" colspan="1">121.13 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C1—C7</td>
<td rowspan="1" colspan="1">120.88 (15)</td>
<td rowspan="1" colspan="1">O2—C9—C10</td>
<td rowspan="1" colspan="1">121.75 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—C1</td>
<td rowspan="1" colspan="1">122.12 (16)</td>
<td rowspan="1" colspan="1">N1—C9—C10</td>
<td rowspan="1" colspan="1">117.12 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2—H2</td>
<td rowspan="1" colspan="1">118.9</td>
<td rowspan="1" colspan="1">C9—C10—H10A</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C2—H2</td>
<td rowspan="1" colspan="1">118.9</td>
<td rowspan="1" colspan="1">C9—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—C2</td>
<td rowspan="1" colspan="1">119.64 (16)</td>
<td rowspan="1" colspan="1">H10A—C10—H10B</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—H3</td>
<td rowspan="1" colspan="1">120.2</td>
<td rowspan="1" colspan="1">C9—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—H3</td>
<td rowspan="1" colspan="1">120.2</td>
<td rowspan="1" colspan="1">H10A—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C4—C5</td>
<td rowspan="1" colspan="1">122.12 (14)</td>
<td rowspan="1" colspan="1">H10B—C10—H10C</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C4—C3</td>
<td rowspan="1" colspan="1">118.36 (15)</td>
<td rowspan="1" colspan="1">C9—C10—H10D</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—C3</td>
<td rowspan="1" colspan="1">119.52 (15)</td>
<td rowspan="1" colspan="1">H10A—C10—H10D</td>
<td rowspan="1" colspan="1">141.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6</td>
<td rowspan="1" colspan="1">119.89 (15)</td>
<td rowspan="1" colspan="1">H10B—C10—H10D</td>
<td rowspan="1" colspan="1">56.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—H5</td>
<td rowspan="1" colspan="1">120.1</td>
<td rowspan="1" colspan="1">H10C—C10—H10D</td>
<td rowspan="1" colspan="1">56.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C5—H5</td>
<td rowspan="1" colspan="1">120.1</td>
<td rowspan="1" colspan="1">C9—C10—H10E</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—C1</td>
<td rowspan="1" colspan="1">121.89 (16)</td>
<td rowspan="1" colspan="1">H10A—C10—H10E</td>
<td rowspan="1" colspan="1">56.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6—H6</td>
<td rowspan="1" colspan="1">119.1</td>
<td rowspan="1" colspan="1">H10B—C10—H10E</td>
<td rowspan="1" colspan="1">141.1</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C6—H6</td>
<td rowspan="1" colspan="1">119.1</td>
<td rowspan="1" colspan="1">H10C—C10—H10E</td>
<td rowspan="1" colspan="1">56.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C7—C8</td>
<td rowspan="1" colspan="1">113.41 (14)</td>
<td rowspan="1" colspan="1">H10D—C10—H10E</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C7—H7A</td>
<td rowspan="1" colspan="1">108.9</td>
<td rowspan="1" colspan="1">C9—C10—H10F</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C7—H7A</td>
<td rowspan="1" colspan="1">108.9</td>
<td rowspan="1" colspan="1">H10A—C10—H10F</td>
<td rowspan="1" colspan="1">56.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—C7—H7B</td>
<td rowspan="1" colspan="1">108.9</td>
<td rowspan="1" colspan="1">H10B—C10—H10F</td>
<td rowspan="1" colspan="1">56.3</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C7—H7B</td>
<td rowspan="1" colspan="1">108.9</td>
<td rowspan="1" colspan="1">H10C—C10—H10F</td>
<td rowspan="1" colspan="1">141.1</td>
</tr>
<tr><td rowspan="1" colspan="1">H7A—C7—H7B</td>
<td rowspan="1" colspan="1">107.7</td>
<td rowspan="1" colspan="1">H10D—C10—H10F</td>
<td rowspan="1" colspan="1">109.5</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C8—C7</td>
<td rowspan="1" colspan="1">113.25 (15)</td>
<td rowspan="1" colspan="1">H10E—C10—H10F</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="d1e1805"><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—H1···O1<sup>i</sup>
</td>
<td rowspan="1" colspan="1">0.86</td>
<td rowspan="1" colspan="1">2.08</td>
<td rowspan="1" colspan="1">2.9048 (18)</td>
<td rowspan="1" colspan="1">161</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—H1A···O2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1">0.82</td>
<td rowspan="1" colspan="1">1.83</td>
<td rowspan="1" colspan="1">2.6464 (17)</td>
<td rowspan="1" colspan="1">174</td>
</tr>
</table>
</table-wrap>
<p>Symmetry codes: (i) −<italic>x</italic>
+1, <italic>y</italic>
+1/2, −<italic>z</italic>
+1/2; (ii) <italic>x</italic>
+1, <italic>y</italic>
, <italic>z</italic>
.</p>
</sec>
</app>
</app-group>
<ref-list><title>References</title>
<ref id="bb1"><mixed-citation publication-type="other">Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). <italic>J. Chem. Soc. Perkin Trans. 2</italic>
, pp. S1–19.</mixed-citation>
</ref>
<ref id="bb2"><mixed-citation publication-type="other">Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). <italic>Angew. Chem. Int. Ed. Engl.</italic>
<bold>34</bold>
, 1555–1573.</mixed-citation>
</ref>
<ref id="bb3"><mixed-citation publication-type="other">Bruker (1998). <italic>SMART</italic>
Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation>
</ref>
<ref id="bb4"><mixed-citation publication-type="other">Bruker (1999). <italic>SAINT</italic>
Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation>
</ref>
<ref id="bb5"><mixed-citation publication-type="other">Burnett, M. N. & Johnson, C. K. (1996). <italic>ORTEPIII</italic>
Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.</mixed-citation>
</ref>
<ref id="bb6"><mixed-citation publication-type="other">Chai, Y., Wan, Z.-L., Guo, H.-Y. & Liu, M.-L. (2009). <italic>Acta Cryst.</italic>
E<bold>65</bold>
, o282.</mixed-citation>
</ref>
<ref id="bb7"><mixed-citation publication-type="other">Etter, M. C. (1990). <italic>Acc. Chem. Res.</italic>
<bold>23</bold>
, 120–126.</mixed-citation>
</ref>
<ref id="bb8"><mixed-citation publication-type="other">Farrugia, L. J. (1997). <italic>J. Appl. Cryst.</italic>
<bold>30</bold>
, 565.</mixed-citation>
</ref>
<ref id="bb9"><mixed-citation publication-type="other">Garcez, W. S., Martins, D. & Garcez, F. R. (2000). <italic>J. Agric. Food Chem.</italic>
<bold>48</bold>
, 3662–3665.</mixed-citation>
</ref>
<ref id="bb10"><mixed-citation publication-type="other">Montedoro, G., Servili, M. & Baldioli, M. (1993). <italic>J. Agric. Food Chem.</italic>
<bold>41</bold>
, 2228–2234.</mixed-citation>
</ref>
<ref id="bb11"><mixed-citation publication-type="other">Pearce, L., Prout, C. K. & Watkin, D. J. (2000). <italic>CAMERON</italic>
Chemical Crystallography Laboratory, University of Oxford, England.</mixed-citation>
</ref>
<ref id="bb14"><mixed-citation publication-type="other">Sheldrick, G. M. (2008<italic>a</italic>
). <italic>SADABS.</italic>
University of Göttingen, Germany.</mixed-citation>
</ref>
<ref id="bb12"><mixed-citation publication-type="other">Sheldrick, G. M. (2008<italic>b</italic>
). <italic>Acta Cryst.</italic>
A<bold>64</bold>
, 112–122.</mixed-citation>
</ref>
<ref id="bb13"><mixed-citation publication-type="other">Song, W.-L., Wang, D., Li, X.-H. & Wang, D.-C. (2008). <italic>Acta Cryst.</italic>
E<bold>64</bold>
, o785.</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⋯O1<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.86</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.08</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.9048 (18)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">161</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1—H1<italic>A</italic>
⋯O2<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.82</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.83</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.6464 (17)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">174</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-65-o1789-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-65-o1789-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>
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