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1<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN" 2 "http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"><html> 3<head> 4<title>(IUCr) Crystallography Journals Online - supplementary material</title> 5<meta name="copyright" content="© International Union of Crystallography 2009" /> 6<style type="text/css"> 7 8 <!--/* <![CDATA[ */ 9 a {color:#000066; text-decoration: none;} 10 a:hover {color:#000000; text-decoration: underline;} 11 .bluetable {border: 2px solid #99ccff;} 12 .openurllink {position: absolute; right: 1.0em;} 13 h1, h2, h3 {margin-top: 0em; margin-bottom: 0.5em;padding: 0em;} 14 /* ]]> */--> 15</style> 16<script language="JavaScript" src="http://journals.iucr.org/javascript/scripts.js" type="text/javascript" ></script><script type="text/javascript"> 17var gaJsHost = (("https:" == 18document.location.protocol) ? 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E<b>65</b>, o739 [ <font size="2"><a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536809007430">doi:10.1107/S1600536809007430</a></font> ]</p></div> 28<h3>(<span class="it"><i>E</i></span>)-1-(4-Chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one</h3><h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Lei,%20X.">X. Lei</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Bai,%20X.">X. Bai</a></h3> 29<div class="abstract"> 30<a name="abstract"></a> 31<div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 32</div> 33<!-- endheading2div --><p>The title compound, C<span class="inf"><sub>17</sub></span>H<span class="inf"><sub>16</sub></span>ClNO, was synthesized using a solvent-free method by reaction of 4-(dimethylamino)benzaldehyde with 4-chloroacetophenone and NaOH. The chlorophenyl ring makes a dihedral angle of 18.1 (3)° with the central propenone unit, while the (dimethylamino)phenyl group is disordered over two orientations of equal occupancies, which make dihedral angles with the central propenone unit of 32.9 (3) and 57.4 (3)°, respectively.</p></div> 34<!-- endabstractdiv --> 35 36 37 38 39 40<div class="contentslist"> 41<ul> 42<li class="comment"><a title="Comment" href="#comment">Comment</a></li> 43<li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li> 44<li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li> 45<li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li> 46<li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li> 47<li class="figures"><a title="Figures" href="#figures">Figures</a></li> 48<li><a title="(I)" href="#chemicalname1">(<i>E</i>)-1-(4-Chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one </a><ul> 49<li><a title="Crystal data" href="#crystaldata1">Crystal data</a></li> 50<li><a title="Data collection" href="#datacollection1">Data collection</a></li> 51<li><a title="Refinement data" href="#refinementdata1">Refinement data</a></li> 52<li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li> 53<li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic coordinates</a></li> 54<li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li> 55<li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li> 56</ul></li> 57<li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li> 58<li class="publreferences"><a title="References" href="#publreferences">References</a></li> 59</ul> 60</div> 61<!-- endcontentslistdiv --> 62 63<div class="comment"> 64<a name="comment"></a> 65<div class="heading2"> 66Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 67</div> 68<!-- endheading2div --><p>This paper discloses a user-friendly, solvent-free protocol for the synthesis of 69chalcones, starting from the fragrant aldehydes and fragrant ketones in the 70presence of NaOH. The method can be considered to be a general route for 71chalcone synthesis, and the title compound was prepared in this way.</p><p>The bond lengths and angles of the molecule (Fig. 1) are normal and comparable 72to those observed in the related compound (Li <i>et al.</i>, 1992). The 73(dimethylamino)phenyl group exhibits rotational disorder, with one orientation 74including atoms C10, C11, C12, C13, C14 and C15, and another orientation 75including C10, C11', C12', C13, C14' and C15'. The refined site occupancy 76factors for the two orientations is 0.500 (5).</p> 77</div> 78<!-- endcommentdiv --> 79 80 81<div class="relatedliterature"> 82<a name="relatedliterature"></a> 83<div class="heading2"> 84Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 85</div> 86<!-- endheading2div --><p>For a related structure, see: Li <i>et al.</i> (1992).</p> 87</div> 88<!-- endrelatedliteraturediv --> 89 90 91<div class="experimental"> 92<a name="experimental"></a> 93<div class="heading2"> 94Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 95</div> 96<!-- endheading2div --><p>4-(Dimethylamino)benzaldehyde (0.5 mmol) and 4-chloroacetophenone (0.5 mmol), 97NaOH (0.5 mmol) were mixed in 50 ml flask under solvent-free conditions After 98stirring for 6 min at 373 K, the mixture was slowly solidified to give the 99title compound. Recrystallization from ethanol gave a yellow crystalline 100solid. Elemental analysis calculated: C 71.45, H 5.64, N 4.90%; found: C 10171.53, H 5.56, N 4.95%.</p> 102</div> 103<!-- endexperimentaldiv --> 104 105 106<div class="refinement"> 107<a name="refinement"></a> 108<div class="heading2"> 109Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 110</div> 111<!-- endheading2div --><p>All H atoms were positioned geometrically and refined using a riding model with 112C—H = 0.93–0.96 Å and <i>U</i><sub>iso</sub>(H) = 1.2 or 1.5<i>U</i><sub>eq</sub>(C). The 113five-membered ring was treated as disordered between two orientations with 114site occupancy factors refined to 0.500 (5). The bonds N1—C16, N1—C16', 115N1—C17 and N1—C17' were restrained to be 1.47 (1)Å.</p> 116</div> 117<!-- endrefinementdiv --> 118 119 120<div class="computingdetails"> 121<a name="computingdetails"></a> 122<div class="heading2"> 123Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 124</div> 125<!-- endheading2div --><p>Data collection: <i>SMART</i> (Bruker, 1997); cell refinement: <i>SAINT</i> (Bruker, 1997); data reduction: <i>SAINT</i> (Bruker, 1997); program(s) used to solve structure: <i>SHELXS97</i> (Sheldrick, 2008); program(s) used to refine structure: <i>SHELXL97</i> (Sheldrick, 2008); molecular graphics: <i>SHELXTL</i> (Sheldrick, 2008); software used to prepare material for publication: <i>SHELXTL</i> (Sheldrick, 2008).</p> 126</div> 127<!-- endcomputingdetailsdiv --> 128 129 130<div class="schemes"> 131<a href="./bi2339scheme1.gif"></a> 132</div> 133<!-- endschemesdiv --> 134 135<div class="figures"> 136 137<div class="tablewrap"> 138<a name="figures"></a> 139<div class="heading2"> 140Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 141</div> 142<!-- endheading2div --><table style="table-layout:fixed" width="100%" class="nodecs"> 143<colgroup span="2"> 144<col width="110"></col> 145<col></col> 146</colgroup> 147<tr><td class="nodecs" align="center" width="110"> 148<a href="./bi2339fig1.html"><img width="100" src="./bi2339fig1thm.gif" alt="[Figure 1]" align="middle"/></a> 149</td><td class="nodecs" valign="middle" > 150<font size="2">Fig. 1. The molecular structure showing 30% probability displacement ellipsoids for 151non-H atoms.</font> 152</td></tr> 153</table> 154</div> 155 156</div> 157<!-- endfiguresdiv --> 158 159<div class="datablock1"> 160 161 162<div class="heading2"> 163<a name="chemicalname1"></a>(<i>E</i>)-1-(4-Chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 164</div> 165<!-- endheading2div --> 166 167 168<div class="tablewrapcrystaldatalong"> 169<a name="crystaldata1"></a><span class="heading3">Crystal data</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 170<colgroup span="2"> 171<col width="50%"></col> 172<col width="50%"></col> 173</colgroup> 174<tr><td width="50%" class="tabledata" >C<sub>17</sub>H<sub>16</sub>ClNO</td><td width="50%" class="tabledata" ><i>F</i><sub>000</sub> = 600</td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 285.76</td><td width="50%" class="tabledata" ><i>D</i><sub>x</sub> = 1.283 Mg m<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >Monoclinic, <i>P</i>2<sub>1</sub>/<i>c</i></td><td width="50%" class="tabledata" >Mo <i>K</i><span style="font-family:Times">α</span> radiation <br /><span style="font-family:Times">λ</span> = 0.71073 Å</td></tr><tr><td width="50%" class="tabledata" >Hall symbol: -P 2ybc</td><td width="50%" class="tabledata" >Cell parameters from 987 reflections</td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 16.792 (2) Å</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span> = 2.5–19.9º</td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 14.5602 (16) Å</td><td width="50%" class="tabledata" >µ = 0.25 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 6.1160 (8) Å</td><td width="50%" class="tabledata" ><i>T</i> = 298 K</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">β</span> = 98.333 (2)º</td><td width="50%" class="tabledata" >Needle, yellow</td></tr><tr><td width="50%" class="tabledata" ><i>V</i> = 1479.5 (3) Å<sup>3</sup></td><td width="50%" class="tabledata" >0.42 × 0.20 × 0.13 mm</td></tr><tr><td width="50%" class="tabledata" ><i>Z</i> = 4</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 175</div> 176<!-- endtablewrapcrystaldatalongdiv --> 177 178<div class="tablewrapdatacollectionlong"> 179<a name="datacollection1"></a><span class="heading3">Data collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 180<colgroup span="2"> 181<col width="50%"></col> 182<col width="50%"></col> 183</colgroup> 184<tr><td width="50%" class="tabledata" >Bruker SMART CCD <br />diffractometer</td><td width="50%" class="tabledata" >2605 independent reflections</td></tr><tr><td width="50%" class="tabledata" >Radiation source: fine-focus sealed tube</td><td width="50%" class="tabledata" >1066 reflections with <i>I</i> > 2˘<i>I</i>)</td></tr><tr><td width="50%" class="tabledata" >Monochromator: graphite</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.068</td></tr><tr><td width="50%" class="tabledata" ><i>T</i> = 298 K</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>max</sub> = 25.0º</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">φ</span> and <span style="font-family:Times">ω</span> scans</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>min</sub> = 1.9º</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: multi-scan<br />(SADABS; Sheldrick, 2003)</td><td width="50%" class="tabledata" ><i>h</i> = <span style="font-family:Times">−</span>19→19</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.901, <i>T</i><sub>max</sub> = 0.968</td><td width="50%" class="tabledata" ><i>k</i> = <span style="font-family:Times">−</span>17→12</td></tr><tr><td width="50%" class="tabledata" >7357 measured reflections</td><td width="50%" class="tabledata" ><i>l</i> = <span style="font-family:Times">−</span>7→7</td></tr></table><!-- endtabledatatable --> 185</div> 186<!-- endtablewrapdatacollectionlongdiv --> 187 188<div class="tablewraprefinementdatalong"> 189<a name="refinementdata1"></a><span class="heading3">Refinement</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 190<colgroup span="2"> 191<col width="50%"></col> 192<col width="50%"></col> 193</colgroup> 194<tr><td width="50%" class="tabledata" >Refinement on <i>F</i><sup>2</sup></td><td width="50%" class="tabledata" >Secondary atom site location: difference Fourier map</td></tr><tr><td width="50%" class="tabledata" >Least-squares matrix: full</td><td width="50%" class="tabledata" >Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td width="50%" class="tabledata" ><i>R</i>[<i>F</i><sup>2</sup> > 2<span style="font-family:Times">σ</span>(<i>F</i><sup>2</sup>)] = 0.059</td><td width="50%" class="tabledata" >H-atom parameters constrained</td></tr><tr><td width="50%" class="tabledata" ><i>wR</i>(<i>F</i><sup>2</sup>) = 0.170</td><td width="50%" class="tabledata" >  <i>w</i> = 1/[<span style="font-family:Times">σ</span><sup>2</sup>(<i>F</i><sub>o</sub><sup>2</sup>) + (0.0749<i>P</i>)<sup>2</sup>] <br />where <i>P</i> = (<i>F</i><sub>o</sub><sup>2</sup> + 2<i>F</i><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td width="50%" class="tabledata" ><i>S</i> = 0.90</td><td width="50%" class="tabledata" >(Δ/<span style="font-family:Times">σ</span>)<sub>max</sub> < 0.001</td></tr><tr><td width="50%" class="tabledata" >2605 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.16 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >237 parameters</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.12 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >4 restraints</td><td width="50%" class="tabledata" >Extinction correction: none</td></tr><tr><td width="50%" class="tabledata" >Primary atom site location: structure-invariant direct methods</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 195</div> 196<!-- endtablewraprefinementdatalongdiv --> 197 198<div class="tablewrapcrystaldatashort"> 199<a name="crystaldata1"></a><span class="heading3">Crystal data</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 200<colgroup span="2"> 201<col width="50%"></col> 202<col width="50%"></col> 203</colgroup> 204<tr><td width="50%" class="tabledata" >C<sub>17</sub>H<sub>16</sub>ClNO</td><td width="50%" class="tabledata" ><i>V</i> = 1479.5 (3) Å<sup>3</sup></td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 285.76</td><td width="50%" class="tabledata" ><i>Z</i> = 4</td></tr><tr><td width="50%" class="tabledata" >Monoclinic, <i>P</i>2<sub>1</sub>/<i>c</i></td><td width="50%" class="tabledata" >Mo <i>K</i><span style="font-family:Times">α</span></td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 16.792 (2) Å</td><td width="50%" class="tabledata" >µ = 0.25 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 14.5602 (16) Å</td><td width="50%" class="tabledata" ><i>T</i> = 298 K</td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 6.1160 (8) Å</td><td width="50%" class="tabledata" >0.42 × 0.20 × 0.13 mm</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">β</span> = 98.333 (2)º</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 205</div> 206<!-- endtablewrapcrystaldatashortdiv --> 207 208<div class="tablewrapdatacollectionshort"> 209<a name="datacollection1"></a><span class="heading3">Data collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 210<colgroup span="2"> 211<col width="50%"></col> 212<col width="50%"></col> 213</colgroup> 214<tr><td width="50%" class="tabledata" >Bruker SMART CCD <br />diffractometer</td><td width="50%" class="tabledata" >2605 independent reflections</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: multi-scan<br />(SADABS; Sheldrick, 2003)</td><td width="50%" class="tabledata" >1066 reflections with <i>I</i> > 2˘<i>I</i>)</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.901, <i>T</i><sub>max</sub> = 0.968</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.068</td></tr><tr><td width="50%" class="tabledata" >7357 measured reflections</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 215</div> 216<!-- endtablewrapdatacollectionshortdiv --> 217 218<div class="tablewraprefinementdatashort"> 219<a name="refinementdata1"></a><span class="heading3">Refinement</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 220<colgroup span="2"> 221<col width="50%"></col> 222<col width="50%"></col> 223</colgroup> 224<tr><td width="50%" class="tabledata" ><i>R</i>[<i>F</i><sup>2</sup> > 2<span style="font-family:Times">σ</span>(<i>F</i><sup>2</sup>)] = 0.059</td><td width="50%" class="tabledata" >4 restraints</td></tr><tr><td width="50%" class="tabledata" ><i>wR</i>(<i>F</i><sup>2</sup>) = 0.170</td><td width="50%" class="tabledata" >H-atom parameters constrained</td></tr><tr><td width="50%" class="tabledata" ><i>S</i> = 0.90</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.16 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >2605 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.12 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >237 parameters</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 225</div> 226<!-- endtablewraprefinementdatashortdiv --> 227<div class="specialdetails"> 228 229<div class="tablewrap"> 230<a name="specialdetails1"></a><span class="heading3">Special details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 231<table style="table-layout:fixed" width="100%" class="tabledata"> 232<tr><td class="tabledata"><p><b>Geometry</b>. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) 233are estimated using the full covariance matrix. The cell e.s.d.'s are taken 234into account individually in the estimation of e.s.d.'s in distances, angles 235and torsion angles; correlations between e.s.d.'s in cell parameters are only 236used when they are defined by crystal symmetry. An approximate (isotropic) 237treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. 238planes.</p></td></tr> 239<tr><td class="tabledata"><p><b>Refinement</b>. Refinement of <i>F</i><sup>2</sup> against ALL reflections. The weighted <i>R</i>-factor 240<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, conventional 241<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for 242negative <i>F</i><sup>2</sup>. The threshold expression of <i>F</i><sup>2</sup> > 243<span style="font-family:Times">σ</span>(<i>F</i><sup>2</sup>) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>. 244and is not relevant to the choice of reflections for refinement. 245<i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically about twice as large 246as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be 247even larger.</p></td></tr></table> 248</div> 249 250</div> 251<!-- endspecialdetailsdiv --> 252 253<div class="tablewrapcoords"> 254<a name="fractionalatomiccoordinates1"></a> <span class="heading3">Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="100%" summary="" class="tabledata"><tr><td class="tabledata" > </td><td class="tabledata" ><i>x</i></td><td class="tabledata" ><i>y</i></td><td class="tabledata" ><i>z</i></td><td class="tabledata" ><i>U</i><sub>iso</sub>*/<i>U</i><sub>eq</sub></td><td class="tabledata" >Occ. (<1)</td></tr><tr><td class="tabledata" >Cl1</td><td class="tabledata" >1.12683 (6)</td><td class="tabledata" >0.14642 (9)</td><td class="tabledata" >1.2060 (3)</td><td class="tabledata" >0.1285 (7)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >N1</td><td class="tabledata" >0.34724 (18)</td><td class="tabledata" >0.1225 (2)</td><td class="tabledata" >0.8419 (7)</td><td class="tabledata" >0.0891 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O1</td><td class="tabledata" >0.80650 (17)</td><td class="tabledata" >0.1009 (2)</td><td class="tabledata" >0.4377 (6)</td><td class="tabledata" >0.1225 (12)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C1</td><td class="tabledata" >0.8071 (2)</td><td class="tabledata" >0.1135 (2)</td><td class="tabledata" >0.6344 (8)</td><td class="tabledata" >0.0739 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C2</td><td class="tabledata" >0.8853 (2)</td><td class="tabledata" >0.1192 (2)</td><td class="tabledata" >0.7831 (7)</td><td class="tabledata" >0.0683 (10)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C3</td><td class="tabledata" >0.8921 (2)</td><td class="tabledata" >0.1538 (2)</td><td class="tabledata" >0.9959 (7)</td><td class="tabledata" >0.0742 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H3</td><td class="tabledata" >0.8460</td><td class="tabledata" >0.1712</td><td class="tabledata" >1.0530</td><td class="tabledata" >0.089*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C4</td><td class="tabledata" >0.9663 (2)</td><td class="tabledata" >0.1627 (2)</td><td class="tabledata" >1.1247 (7)</td><td class="tabledata" >0.0801 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H4</td><td class="tabledata" >0.9701</td><td class="tabledata" >0.1868</td><td class="tabledata" >1.2666</td><td class="tabledata" >0.096*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C5</td><td class="tabledata" >1.0345 (2)</td><td class="tabledata" >0.1356 (3)</td><td class="tabledata" >1.0416 (9)</td><td class="tabledata" >0.0831 (12)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C6</td><td class="tabledata" >1.0292 (3)</td><td class="tabledata" >0.0990 (3)</td><td class="tabledata" >0.8348 (9)</td><td class="tabledata" >0.0889 (13)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H6</td><td class="tabledata" >1.0755</td><td class="tabledata" >0.0792</td><td class="tabledata" >0.7816</td><td class="tabledata" >0.107*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C7</td><td class="tabledata" >0.9552 (2)</td><td class="tabledata" >0.0914 (2)</td><td class="tabledata" >0.7048 (7)</td><td class="tabledata" >0.0792 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H7</td><td class="tabledata" >0.9520</td><td class="tabledata" >0.0673</td><td class="tabledata" >0.5629</td><td class="tabledata" >0.095*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C8</td><td class="tabledata" >0.7314 (2)</td><td class="tabledata" >0.1221 (2)</td><td class="tabledata" >0.7236 (7)</td><td class="tabledata" >0.0754 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8</td><td class="tabledata" >0.7343</td><td class="tabledata" >0.1272</td><td class="tabledata" >0.8762</td><td class="tabledata" >0.090*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C9</td><td class="tabledata" >0.6615 (2)</td><td class="tabledata" >0.1233 (3)</td><td class="tabledata" >0.6088 (7)</td><td class="tabledata" >0.0872 (12)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9</td><td class="tabledata" >0.6617</td><td class="tabledata" >0.1225</td><td class="tabledata" >0.4568</td><td class="tabledata" >0.105*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C10</td><td class="tabledata" >0.5811 (2)</td><td class="tabledata" >0.1255 (3)</td><td class="tabledata" >0.6741 (6)</td><td class="tabledata" >0.0639 (9)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C11</td><td class="tabledata" >0.5655 (5)</td><td class="tabledata" >0.0979 (6)</td><td class="tabledata" >0.8724 (14)</td><td class="tabledata" >0.055 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H11</td><td class="tabledata" >0.6076</td><td class="tabledata" >0.0821</td><td class="tabledata" >0.9821</td><td class="tabledata" >0.065*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C12</td><td class="tabledata" >0.4860 (5)</td><td class="tabledata" >0.0928 (6)</td><td class="tabledata" >0.9147 (13)</td><td class="tabledata" >0.059 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H12</td><td class="tabledata" >0.4773</td><td class="tabledata" >0.0651</td><td class="tabledata" >1.0463</td><td class="tabledata" >0.070*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C13</td><td class="tabledata" >0.4234 (2)</td><td class="tabledata" >0.1232 (2)</td><td class="tabledata" >0.7863 (7)</td><td class="tabledata" >0.0639 (10)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C14</td><td class="tabledata" >0.4419 (4)</td><td class="tabledata" >0.1658 (5)</td><td class="tabledata" >0.5679 (11)</td><td class="tabledata" >0.057 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H14</td><td class="tabledata" >0.4007</td><td class="tabledata" >0.1885</td><td class="tabledata" >0.4641</td><td class="tabledata" >0.068*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C15</td><td class="tabledata" >0.5208 (4)</td><td class="tabledata" >0.1695 (5)</td><td class="tabledata" >0.5295 (12)</td><td class="tabledata" >0.059 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H15</td><td class="tabledata" >0.5339</td><td class="tabledata" >0.2012</td><td class="tabledata" >0.4075</td><td class="tabledata" >0.070*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C16</td><td class="tabledata" >0.2783 (5)</td><td class="tabledata" >0.0794 (8)</td><td class="tabledata" >0.7432 (18)</td><td class="tabledata" >0.103 (4)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H16A</td><td class="tabledata" >0.2583</td><td class="tabledata" >0.1102</td><td class="tabledata" >0.6074</td><td class="tabledata" >0.154*</td><td class="tabledata" >0.510 (7)</td></tr><tr><td class="tabledata" >H16B</td><td class="tabledata" >0.2383</td><td class="tabledata" >0.0815</td><td class="tabledata" >0.8404</td><td class="tabledata" >0.154*</td><td class="tabledata" >0.510 (7)</td></tr><tr><td class="tabledata" >H16C</td><td class="tabledata" >0.2902</td><td class="tabledata" >0.0166</td><td class="tabledata" >0.7128</td><td class="tabledata" >0.154*</td><td class="tabledata" >0.510 (7)</td></tr><tr><td class="tabledata" >C17</td><td class="tabledata" >0.3364 (5)</td><td class="tabledata" >0.1683 (7)</td><td class="tabledata" >1.0661 (13)</td><td class="tabledata" >0.106 (4)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H17A</td><td class="tabledata" >0.3811</td><td class="tabledata" >0.1526</td><td class="tabledata" >1.1758</td><td class="tabledata" >0.158*</td><td class="tabledata" >0.510 (7)</td></tr><tr><td class="tabledata" >H17B</td><td class="tabledata" >0.2874</td><td class="tabledata" >0.1466</td><td class="tabledata" >1.1123</td><td class="tabledata" >0.158*</td><td class="tabledata" >0.510 (7)</td></tr><tr><td class="tabledata" >H17C</td><td class="tabledata" >0.3338</td><td class="tabledata" >0.2337</td><td class="tabledata" >1.0483</td><td class="tabledata" >0.158*</td><td class="tabledata" >0.510 (7)</td></tr><tr><td class="tabledata" >C11'</td><td class="tabledata" >0.5658 (5)</td><td class="tabledata" >0.1596 (6)</td><td class="tabledata" >0.8637 (16)</td><td class="tabledata" >0.060 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H11'</td><td class="tabledata" >0.6089</td><td class="tabledata" >0.1842</td><td class="tabledata" >0.9581</td><td class="tabledata" >0.073*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C12'</td><td class="tabledata" >0.4923 (4)</td><td class="tabledata" >0.1618 (6)</td><td class="tabledata" >0.9327 (12)</td><td class="tabledata" >0.060 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H12'</td><td class="tabledata" >0.4859</td><td class="tabledata" >0.1870</td><td class="tabledata" >1.0688</td><td class="tabledata" >0.072*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C14'</td><td class="tabledata" >0.4368 (4)</td><td class="tabledata" >0.0774 (5)</td><td class="tabledata" >0.6145 (12)</td><td class="tabledata" >0.059 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H14'</td><td class="tabledata" >0.3949</td><td class="tabledata" >0.0445</td><td class="tabledata" >0.5344</td><td class="tabledata" >0.070*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C15'</td><td class="tabledata" >0.5112 (4)</td><td class="tabledata" >0.0760 (5)</td><td class="tabledata" >0.5472 (12)</td><td class="tabledata" >0.064 (2)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H15'</td><td class="tabledata" >0.5184</td><td class="tabledata" >0.0436</td><td class="tabledata" >0.4203</td><td class="tabledata" >0.076*</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >C16'</td><td class="tabledata" >0.2804 (4)</td><td class="tabledata" >0.1498 (7)</td><td class="tabledata" >0.6472 (14)</td><td class="tabledata" >0.090 (3)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H16D</td><td class="tabledata" >0.2919</td><td class="tabledata" >0.2095</td><td class="tabledata" >0.5931</td><td class="tabledata" >0.135*</td><td class="tabledata" >0.490 (7)</td></tr><tr><td class="tabledata" >H16E</td><td class="tabledata" >0.2290</td><td class="tabledata" >0.1509</td><td class="tabledata" >0.6988</td><td class="tabledata" >0.135*</td><td class="tabledata" >0.490 (7)</td></tr><tr><td class="tabledata" >H16F</td><td class="tabledata" >0.2791</td><td class="tabledata" >0.1056</td><td class="tabledata" >0.5302</td><td class="tabledata" >0.135*</td><td class="tabledata" >0.490 (7)</td></tr><tr><td class="tabledata" >C17'</td><td class="tabledata" >0.3231 (5)</td><td class="tabledata" >0.0619 (6)</td><td class="tabledata" >0.9866 (13)</td><td class="tabledata" >0.079 (3)</td><td class="tabledata" >0.500 (5)</td></tr><tr><td class="tabledata" >H17D</td><td class="tabledata" >0.3431</td><td class="tabledata" >0.0019</td><td class="tabledata" >0.9590</td><td class="tabledata" >0.119*</td><td class="tabledata" >0.490 (7)</td></tr><tr><td class="tabledata" >H17E</td><td class="tabledata" >0.2654</td><td class="tabledata" >0.0604</td><td class="tabledata" >0.9688</td><td class="tabledata" >0.119*</td><td class="tabledata" >0.490 (7)</td></tr><tr><td class="tabledata" >H17F</td><td class="tabledata" >0.3437</td><td class="tabledata" >0.0804</td><td class="tabledata" >1.1347</td><td class="tabledata" >0.119*</td><td class="tabledata" >0.490 (7)</td></tr></table> 255</div> 256<!-- endtablewrapcoordsdiv --> 257<div class="tablewrapadps"> 258<a name="atomicdisplacement1"></a> <span class="heading3">Atomic displacement parameters (Å<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="100%" summary="" class="tabledata"><tr><td class="tabledata" > </td><td class="tabledata" ><i>U</i><sup>11</sup></td><td class="tabledata" ><i>U</i><sup>22</sup></td><td class="tabledata" ><i>U</i><sup>33</sup></td><td class="tabledata" ><i>U</i><sup>12</sup></td><td class="tabledata" ><i>U</i><sup>13</sup></td><td class="tabledata" ><i>U</i><sup>23</sup></td></tr><tr><td class="tabledata" >Cl1</td><td class="tabledata" >0.0640 (8)</td><td class="tabledata" >0.1472 (12)</td><td class="tabledata" >0.1697 (14)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0010 (6)</td><td class="tabledata" >0.0012 (8)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0022 (9)</td></tr><tr><td class="tabledata" >N1</td><td class="tabledata" >0.053 (2)</td><td class="tabledata" >0.084 (2)</td><td class="tabledata" >0.132 (3)</td><td class="tabledata" >0.0039 (18)</td><td class="tabledata" >0.021 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.008 (3)</td></tr><tr><td class="tabledata" >O1</td><td class="tabledata" >0.085 (2)</td><td class="tabledata" >0.211 (4)</td><td class="tabledata" >0.078 (2)</td><td class="tabledata" >0.001 (2)</td><td class="tabledata" >0.0324 (18)</td><td class="tabledata" >0.006 (2)</td></tr><tr><td class="tabledata" >C1</td><td class="tabledata" >0.069 (3)</td><td class="tabledata" >0.072 (3)</td><td class="tabledata" >0.087 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0025 (19)</td><td class="tabledata" >0.033 (2)</td><td class="tabledata" >0.000 (2)</td></tr><tr><td class="tabledata" >C2</td><td class="tabledata" >0.061 (2)</td><td class="tabledata" >0.061 (2)</td><td class="tabledata" >0.089 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0045 (18)</td><td class="tabledata" >0.032 (2)</td><td class="tabledata" >0.003 (2)</td></tr><tr><td class="tabledata" >C3</td><td class="tabledata" >0.059 (3)</td><td class="tabledata" >0.080 (3)</td><td class="tabledata" >0.087 (3)</td><td class="tabledata" >0.0014 (18)</td><td class="tabledata" >0.024 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.003 (2)</td></tr><tr><td class="tabledata" >C4</td><td class="tabledata" >0.074 (3)</td><td class="tabledata" >0.075 (3)</td><td class="tabledata" >0.094 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.001 (2)</td><td class="tabledata" >0.022 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.003 (2)</td></tr><tr><td class="tabledata" >C5</td><td class="tabledata" >0.060 (3)</td><td class="tabledata" >0.074 (3)</td><td class="tabledata" >0.118 (4)</td><td class="tabledata" >0.003 (2)</td><td class="tabledata" >0.023 (3)</td><td class="tabledata" >0.007 (3)</td></tr><tr><td class="tabledata" >C6</td><td class="tabledata" >0.071 (3)</td><td class="tabledata" >0.084 (3)</td><td class="tabledata" >0.120 (4)</td><td class="tabledata" >0.003 (2)</td><td class="tabledata" >0.043 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.005 (3)</td></tr><tr><td class="tabledata" >C7</td><td class="tabledata" >0.074 (3)</td><td class="tabledata" >0.074 (3)</td><td class="tabledata" >0.097 (3)</td><td class="tabledata" >0.001 (2)</td><td class="tabledata" >0.037 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.007 (2)</td></tr><tr><td class="tabledata" >C8</td><td class="tabledata" >0.062 (2)</td><td class="tabledata" >0.090 (3)</td><td class="tabledata" >0.077 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.010 (2)</td><td class="tabledata" >0.021 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.015 (2)</td></tr><tr><td class="tabledata" >C9</td><td class="tabledata" >0.071 (3)</td><td class="tabledata" >0.130 (3)</td><td class="tabledata" >0.063 (3)</td><td class="tabledata" >0.021 (2)</td><td class="tabledata" >0.018 (2)</td><td class="tabledata" >0.019 (2)</td></tr><tr><td class="tabledata" >C10</td><td class="tabledata" >0.058 (2)</td><td class="tabledata" >0.075 (2)</td><td class="tabledata" >0.059 (3)</td><td class="tabledata" >0.007 (2)</td><td class="tabledata" >0.0076 (19)</td><td class="tabledata" >0.001 (2)</td></tr><tr><td class="tabledata" >C11</td><td class="tabledata" >0.050 (5)</td><td class="tabledata" >0.057 (5)</td><td class="tabledata" >0.056 (6)</td><td class="tabledata" >0.007 (4)</td><td class="tabledata" >0.003 (4)</td><td class="tabledata" >0.004 (5)</td></tr><tr><td class="tabledata" >C12</td><td class="tabledata" >0.069 (6)</td><td class="tabledata" >0.057 (5)</td><td class="tabledata" >0.052 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.006 (5)</td><td class="tabledata" >0.013 (4)</td><td class="tabledata" >0.000 (4)</td></tr><tr><td class="tabledata" >C13</td><td class="tabledata" >0.050 (2)</td><td class="tabledata" >0.054 (2)</td><td class="tabledata" >0.087 (3)</td><td class="tabledata" >0.0039 (19)</td><td class="tabledata" >0.005 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.008 (2)</td></tr><tr><td class="tabledata" >C14</td><td class="tabledata" >0.057 (5)</td><td class="tabledata" >0.051 (5)</td><td class="tabledata" >0.058 (5)</td><td class="tabledata" >0.002 (3)</td><td class="tabledata" >0.000 (3)</td><td class="tabledata" >0.008 (3)</td></tr><tr><td class="tabledata" >C15</td><td class="tabledata" >0.066 (5)</td><td class="tabledata" >0.053 (5)</td><td class="tabledata" >0.058 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.007 (4)</td><td class="tabledata" >0.012 (4)</td><td class="tabledata" >0.003 (3)</td></tr><tr><td class="tabledata" >C16</td><td class="tabledata" >0.076 (6)</td><td class="tabledata" >0.114 (8)</td><td class="tabledata" >0.118 (10)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.024 (6)</td><td class="tabledata" >0.015 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.030 (7)</td></tr><tr><td class="tabledata" >C17</td><td class="tabledata" >0.071 (6)</td><td class="tabledata" >0.151 (9)</td><td class="tabledata" >0.098 (8)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.002 (5)</td><td class="tabledata" >0.025 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.002 (6)</td></tr><tr><td class="tabledata" >C11'</td><td class="tabledata" >0.053 (5)</td><td class="tabledata" >0.058 (6)</td><td class="tabledata" >0.067 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.005 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.001 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.012 (5)</td></tr><tr><td class="tabledata" >C12'</td><td class="tabledata" >0.058 (5)</td><td class="tabledata" >0.072 (6)</td><td class="tabledata" >0.051 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.008 (5)</td><td class="tabledata" >0.011 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.008 (4)</td></tr><tr><td class="tabledata" >C14'</td><td class="tabledata" >0.047 (4)</td><td class="tabledata" >0.060 (6)</td><td class="tabledata" >0.067 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.005 (3)</td><td class="tabledata" >0.000 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.011 (4)</td></tr><tr><td class="tabledata" >C15'</td><td class="tabledata" >0.067 (5)</td><td class="tabledata" >0.064 (6)</td><td class="tabledata" >0.060 (5)</td><td class="tabledata" >0.005 (4)</td><td class="tabledata" >0.008 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.006 (4)</td></tr><tr><td class="tabledata" >C16'</td><td class="tabledata" >0.049 (5)</td><td class="tabledata" >0.111 (8)</td><td class="tabledata" >0.105 (8)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.001 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.001 (5)</td><td class="tabledata" >0.014 (6)</td></tr><tr><td class="tabledata" >C17'</td><td class="tabledata" >0.076 (5)</td><td class="tabledata" >0.094 (7)</td><td class="tabledata" >0.071 (7)</td><td class="tabledata" >0.011 (5)</td><td class="tabledata" >0.023 (5)</td><td class="tabledata" >0.011 (5)</td></tr></table> 259</div> 260<!-- endtablewrapadpsdiv --> 261<div class="tablewrapgeomlong"> 262<a name="geometricparameters1"></a> <span class="heading3">Geometric parameters (Å, °)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><!-- startgeom --><table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 263<colgroup span="4"> 264<col width="30%"></col> 265<col width="20%"></col> 266<col width="30%"></col> 267<col width="20%"></col> 268</colgroup> 269<tr><td width="30%" class="tabledata" >Cl1—C5</td><td width="20%" class="tabledata" >1.729 (4)</td><td width="30%" class="tabledata" >C11—H11</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >N1—C17'</td><td width="20%" class="tabledata" >1.353 (7)</td><td width="30%" class="tabledata" >C12—C13</td><td width="20%" class="tabledata" >1.296 (8)</td></tr><tr><td width="30%" class="tabledata" >N1—C13</td><td width="20%" class="tabledata" >1.370 (4)</td><td width="30%" class="tabledata" >C12—H12</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >N1—C16</td><td width="20%" class="tabledata" >1.377 (7)</td><td width="30%" class="tabledata" >C13—C14'</td><td width="20%" class="tabledata" >1.292 (7)</td></tr><tr><td width="30%" class="tabledata" >N1—C17</td><td width="20%" class="tabledata" >1.559 (7)</td><td width="30%" class="tabledata" >C13—C12'</td><td width="20%" class="tabledata" >1.468 (8)</td></tr><tr><td width="30%" class="tabledata" >N1—C16'</td><td width="20%" class="tabledata" >1.565 (7)</td><td width="30%" class="tabledata" >C13—C14</td><td width="20%" class="tabledata" >1.545 (8)</td></tr><tr><td width="30%" class="tabledata" >O1—C1</td><td width="20%" class="tabledata" >1.215 (4)</td><td width="30%" class="tabledata" >C14—C15</td><td width="20%" class="tabledata" >1.379 (8)</td></tr><tr><td width="30%" class="tabledata" >C1—C8</td><td width="20%" class="tabledata" >1.460 (5)</td><td width="30%" class="tabledata" >C14—H14</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >C1—C2</td><td width="20%" class="tabledata" >1.486 (5)</td><td width="30%" class="tabledata" >C15—H15</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >C2—C3</td><td width="20%" class="tabledata" >1.385 (5)</td><td width="30%" class="tabledata" >C16—H16A</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C2—C7</td><td width="20%" class="tabledata" >1.391 (4)</td><td width="30%" class="tabledata" >C16—H16B</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C3—C4</td><td width="20%" class="tabledata" >1.379 (5)</td><td width="30%" class="tabledata" >C16—H16C</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C3—H3</td><td width="20%" class="tabledata" >0.930</td><td width="30%" class="tabledata" >C17—H17A</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C4—C5</td><td width="20%" class="tabledata" >1.376 (5)</td><td width="30%" class="tabledata" >C17—H17B</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C4—H4</td><td width="20%" class="tabledata" >0.930</td><td width="30%" class="tabledata" >C17—H17C</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C5—C6</td><td width="20%" class="tabledata" >1.364 (5)</td><td width="30%" class="tabledata" >C11'—C12'</td><td width="20%" class="tabledata" >1.362 (10)</td></tr><tr><td width="30%" class="tabledata" >C6—C7</td><td width="20%" class="tabledata" >1.380 (5)</td><td width="30%" class="tabledata" >C11'—H11'</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >C6—H6</td><td width="20%" class="tabledata" >0.930</td><td width="30%" class="tabledata" >C12'—H12'</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >C7—H7</td><td width="20%" class="tabledata" >0.930</td><td width="30%" class="tabledata" >C14'—C15'</td><td width="20%" class="tabledata" >1.372 (9)</td></tr><tr><td width="30%" class="tabledata" >C8—C9</td><td width="20%" class="tabledata" >1.278 (5)</td><td width="30%" class="tabledata" >C14'—H14'</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >C8—H8</td><td width="20%" class="tabledata" >0.930</td><td width="30%" class="tabledata" >C15'—H15'</td><td width="20%" class="tabledata" >0.930</td></tr><tr><td width="30%" class="tabledata" >C9—C10</td><td width="20%" class="tabledata" >1.463 (5)</td><td width="30%" class="tabledata" >C16'—H16D</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C9—H9</td><td width="20%" class="tabledata" >0.930</td><td width="30%" class="tabledata" >C16'—H16E</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C10—C11'</td><td width="20%" class="tabledata" >1.320 (9)</td><td width="30%" class="tabledata" >C16'—H16F</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C10—C11</td><td width="20%" class="tabledata" >1.339 (9)</td><td width="30%" class="tabledata" >C17'—H17D</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabledata" >C10—C15</td><td width="20%" class="tabledata" >1.399 (8)</td><td width="30%" class="tabledata" >C17'—H17E</td><td width="20%" class="tabledata" >0.960</td></tr><tr><td width="30%" class="tabl…
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