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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>, o197 [ <font size="2"><a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536808043201">doi:10.1107/S1600536808043201</a></font> ]</p></div> 28<h3>(<span class="it"><i>S</i></span>)-1-[3,5-Bis(trifluoromethyl)phenyl]-<span class="it"><i>N</i></span>-methylethylamine-(<span class="it"><i>R</i></span>)-2-hydroxybutanedioic acid (1/1)</h3><h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Zhu,%20H.-B.">H.-B. Zhu</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Ji,%20J.-F.">J.-F. Ji</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Wang,%20H.">H. Wang</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>In the title compound, C<span class="inf"><sub>11</sub></span>H<span class="inf"><sub>11</sub></span>F<span class="inf"><sub>6</sub></span>N·C<span class="inf"><sub>4</sub></span>H<span class="inf"><sub>6</sub></span>O<span class="inf"><sub>5</sub></span>, a key intermediate in the synthesis of the NK1 receptor antagonist of casopitant, the F atoms of the trifluoromethyl groups are disordered over two sites with equal occupancies. In the crystal, the components are linked by bifurcated N-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />(O,O) hydrogen bonds.</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>S</i>)-1-[3,5-Bis(trifluoromethyl)phenyl]-<i>N</i>-methylethylamine– 49(<i>R</i>)-2-hydroxybutanedioic acid (1/1) </a><ul> 50<li><a title="Crystal data" href="#crystaldata1">Crystal data</a></li> 51<li><a title="Data collection" href="#datacollection1">Data collection</a></li> 52<li><a title="Refinement data" href="#refinementdata1">Refinement data</a></li> 53<li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li> 54<li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic coordinates</a></li> 55<li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li> 56<li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li> 57<li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 58<li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 59</ul></li> 60<li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li> 61<li class="publreferences"><a title="References" href="#publreferences">References</a></li> 62</ul> 63</div> 64<!-- endcontentslistdiv --> 65 66<div class="comment"> 67<a name="comment"></a> 68<div class="heading2"> 69Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 70</div> 71<!-- endheading2div --><p>The title compound, C<sub>11</sub>H<sub>11</sub>F<sub>6</sub>N.C<sub>4</sub>H<sub>6</sub>O<sub>5</sub>, is a key intermediate 72for the synthesis of casopitant, which is an NK1 receptor antagonist 73(Humphrey, 2003) for the 74treatment of chemotheraphy-induced nausea and vomiting (CINV) (Lohr, 752008).</p><p>The molecular structure of the title compound is shown in Fig.1. The F atoms of 76the trifluoromethyl group are disordered over two sites in a 0.50:0.50 ratio. 77N—H···O hydrogen bonding interactions occur between (<i>S</i>)-1-(3, 785-bis(trifluoromethyl)-phenyl)ethylamine <i>N</i>-monomethyl and 79(<i>R</i>)-2-hydroxybutanedioic acid (Table 1).</p> 80</div> 81<!-- endcommentdiv --> 82 83 84<div class="relatedliterature"> 85<a name="relatedliterature"></a> 86<div class="heading2"> 87Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 88</div> 89<!-- endheading2div --><p>For the NK1 receptor antagonist, see: Humphrey (2003).</p> 90</div> 91<!-- endrelatedliteraturediv --> 92 93 94<div class="experimental"> 95<a name="experimental"></a> 96<div class="heading2"> 97Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 98</div> 99<!-- endheading2div --><p>To a solution of 3, 5-bis(trifluoromethyl)-phenyl)ethylamine 100<i>N</i>-monomethyl (2.71 g, 10 mmol) in EtOAc (25 ml), 101(<i>R</i>)-2-hydroxybutanedioic acid (1.34,10 mmol) was added portionwise. The 102suspension was stirred for 2h at 298 K, then for 3 h at 273 K. The suspension 103was filtered and the cake was washed with EtOAc (20 ml). The solid was dried 104under vacucum obtaining the crude title compound (1.48 g). Single crystal of 105the title compound suitable for X-ray diffraction was obtained by slow 106evaporation of the EtOAc solution of the title compound.</p> 107</div> 108<!-- endexperimentaldiv --> 109 110 111<div class="refinement"> 112<a name="refinement"></a> 113<div class="heading2"> 114Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 115</div> 116<!-- endheading2div --><p>All H atoms were positoned geometrically and allowed to ride on their parent 117atoms, with C—H = 0.93Å for aromatic H atoms, 0.96Å for methyl H atoms, 1180.97Å for methylene H atoms, 0.98Å for methine H atoms and O—H = 0.82 Å, N—H = 0.86 Å, respectively. [<i>U</i><sub>iso</sub> (H) = 1.2<i>U</i><sub>eq</sub>(C) 119for aromatic, methylene and methine; <i>U</i><sub>iso</sub>(H) = 1.5 <i>U</i><sub>eq</sub>(C) 120for methyl, <i>U</i><sub>iso</sub>(H) = 1.2<i>U</i><sub>eq</sub>(N); <i>U</i><sub>iso</sub>(H) = 1.5 121<i>U</i><sub>eq</sub>(O).]</p> 122</div> 123<!-- endrefinementdiv --> 124 125 126<div class="computingdetails"> 127<a name="computingdetails"></a> 128<div class="heading2"> 129Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 130</div> 131<!-- endheading2div --><p>Data collection: <i>CAD-4 Software</i> (Enraf–Nonius,1989); cell refinement: <i>CAD-4 Software</i>; data reduction: <i>XCAD4</i> (Harms & Wocadlo, 1995); 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>SHELXL97</i> (Sheldrick, 2008).</p> 132</div> 133<!-- endcomputingdetailsdiv --> 134 135 136<div class="schemes"> 137<a href="./at2692scheme1.gif"></a> 138</div> 139<!-- endschemesdiv --> 140 141<div class="figures"> 142 143<div class="tablewrap"> 144<a name="figures"></a> 145<div class="heading2"> 146Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 147</div> 148<!-- endheading2div --><table style="table-layout:fixed" width="100%" class="nodecs"> 149<colgroup span="2"> 150<col width="110"></col> 151<col></col> 152</colgroup> 153<tr><td class="nodecs" align="center" width="110"> 154<a href="./at2692fig1.html"><img width="100" src="./at2692fig1thm.gif" alt="[Figure 1]" align="middle"/></a> 155</td><td class="nodecs" valign="middle" > 156<font size="2">Fig. 1. The molecular structure of the title compound, drawn with 30% probability 157ellipsoids.</font> 158</td></tr> 159</table> 160</div> 161 162</div> 163<!-- endfiguresdiv --> 164 165<div class="datablock1"> 166 167 168<div class="heading2"> 169<a name="chemicalname1"></a>(<i>S</i>)-1-[3,5-Bis(trifluoromethyl)phenyl]-<i>N</i>-methylethylamine– 170(<i>R</i>)-2-hydroxybutanedioic acid (1/1) <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 171</div> 172<!-- endheading2div --> 173 174 175<div class="tablewrapcrystaldatalong"> 176<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"> 177<colgroup span="2"> 178<col width="50%"></col> 179<col width="50%"></col> 180</colgroup> 181<tr><td width="50%" class="tabledata" >C<sub>11</sub>H<sub>11</sub>F<sub>6</sub>N·C<sub>4</sub>H<sub>6</sub>O<sub>5</sub></td><td width="50%" class="tabledata" ><i>F</i><sub>000</sub> = 416</td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 405.30</td><td width="50%" class="tabledata" ><i>D</i><sub>x</sub> = 1.480 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></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 2yb</td><td width="50%" class="tabledata" >Cell parameters from 25 reflections</td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 6.6770 (13) Å</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span> = 9–12º</td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 8.4510 (17) Å</td><td width="50%" class="tabledata" >µ = 0.15 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 16.366 (3) 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> = 100.05 (3)º</td><td width="50%" class="tabledata" >Needle, colourless</td></tr><tr><td width="50%" class="tabledata" ><i>V</i> = 909.3 (3) Å<sup>3</sup></td><td width="50%" class="tabledata" >0.30 × 0.10 × 0.10 mm</td></tr><tr><td width="50%" class="tabledata" ><i>Z</i> = 2</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 182</div> 183<!-- endtablewrapcrystaldatalongdiv --> 184 185<div class="tablewrapdatacollectionlong"> 186<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"> 187<colgroup span="2"> 188<col width="50%"></col> 189<col width="50%"></col> 190</colgroup> 191<tr><td width="50%" class="tabledata" >Enraf–Nonius CAD-4 <br />diffractometer</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.058</td></tr><tr><td width="50%" class="tabledata" >Radiation source: fine-focus sealed tube</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>max</sub> = 25.3º</td></tr><tr><td width="50%" class="tabledata" >Monochromator: graphite</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>min</sub> = 1.3º</td></tr><tr><td width="50%" class="tabledata" ><i>T</i> = 298 K</td><td width="50%" class="tabledata" ><i>h</i> = 0→7</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">ω</span>/2<span style="font-family:Times">θ</span> scans</td><td width="50%" class="tabledata" ><i>k</i> = 0→10</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: <span style="font-family:Times">ψ</span> scan<br />(North <i>et al.</i>, 1968)</td><td width="50%" class="tabledata" ><i>l</i> = <span style="font-family:Times">−</span>19→19</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.957, <i>T</i><sub>max</sub> = 0.985</td><td width="50%" class="tabledata" >3 standard reflections</td></tr><tr><td width="50%" class="tabledata" >1915 measured reflections</td><td width="50%" class="tabledata" > every 200 reflections</td></tr><tr><td width="50%" class="tabledata" >1757 independent reflections</td><td width="50%" class="tabledata" > intensity decay: 1%</td></tr><tr><td width="50%" class="tabledata" >1067 reflections with <i>I</i> > 2<span style="font-family:Times">σ</span>(<i>I</i>)</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 192</div> 193<!-- endtablewrapdatacollectionlongdiv --> 194 195<div class="tablewraprefinementdatalong"> 196<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"> 197<colgroup span="2"> 198<col width="50%"></col> 199<col width="50%"></col> 200</colgroup> 201<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>)] = 0.063</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>) = 0.154</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>) + (0.060<i>P</i>)<sup>2</sup> + 0.3<i>P</i>] <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> = 1.00</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" >1757 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.18 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >220 parameters</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.27 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >2 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 --> 202</div> 203<!-- endtablewraprefinementdatalongdiv --> 204 205<div class="tablewrapcrystaldatashort"> 206<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"> 207<colgroup span="2"> 208<col width="50%"></col> 209<col width="50%"></col> 210</colgroup> 211<tr><td width="50%" class="tabledata" >C<sub>11</sub>H<sub>11</sub>F<sub>6</sub>N·C<sub>4</sub>H<sub>6</sub>O<sub>5</sub></td><td width="50%" class="tabledata" ><i>V</i> = 909.3 (3) Å<sup>3</sup></td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 405.30</td><td width="50%" class="tabledata" ><i>Z</i> = 2</td></tr><tr><td width="50%" class="tabledata" >Monoclinic, <i>P</i>2<sub>1</sub></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> = 6.6770 (13) Å</td><td width="50%" class="tabledata" >µ = 0.15 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 8.4510 (17) Å</td><td width="50%" class="tabledata" ><i>T</i> = 298 K</td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 16.366 (3) Å</td><td width="50%" class="tabledata" >0.30 × 0.10 × 0.10 mm</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">β</span> = 100.05 (3)º</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 212</div> 213<!-- endtablewrapcrystaldatashortdiv --> 214 215<div class="tablewrapdatacollectionshort"> 216<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"> 217<colgroup span="2"> 218<col width="50%"></col> 219<col width="50%"></col> 220</colgroup> 221<tr><td width="50%" class="tabledata" >Enraf–Nonius CAD-4 <br />diffractometer</td><td width="50%" class="tabledata" >1067 reflections with <i>I</i> > 2<span style="font-family:Times">σ</span>(<i>I</i>)</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: <span style="font-family:Times">ψ</span> scan<br />(North <i>et al.</i>, 1968)</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.058</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.957, <i>T</i><sub>max</sub> = 0.985</td><td width="50%" class="tabledata" >3 standard reflections</td></tr><tr><td width="50%" class="tabledata" >1915 measured reflections</td><td width="50%" class="tabledata" > every 200 reflections</td></tr><tr><td width="50%" class="tabledata" >1757 independent reflections</td><td width="50%" class="tabledata" > intensity decay: 1%</td></tr></table><!-- endtabledatatable --> 222</div> 223<!-- endtablewrapdatacollectionshortdiv --> 224 225<div class="tablewraprefinementdatashort"> 226<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"> 227<colgroup span="2"> 228<col width="50%"></col> 229<col width="50%"></col> 230</colgroup> 231<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>)] = 0.063</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>) = 0.154</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.18 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" ><i>S</i> = 1.00</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.27 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >1757 reflections</td><td width="50%" class="tabledata" >Absolute structure: ?</td></tr><tr><td width="50%" class="tabledata" >220 parameters</td><td width="50%" class="tabledata" >Flack parameter: ?</td></tr><tr><td width="50%" class="tabledata" >2 restraints</td><td width="50%" class="tabledata" >Rogers parameter: ?</td></tr></table><!-- endtabledatatable --> 232</div> 233<!-- endtablewraprefinementdatashortdiv --> 234<div class="specialdetails"> 235 236<div class="tablewrap"> 237<a name="specialdetails1"></a><span class="heading3">Special details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 238<table style="table-layout:fixed" width="100%" class="tabledata"> 239<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) 240are estimated using the full covariance matrix. The cell e.s.d.'s are taken 241into account individually in the estimation of e.s.d.'s in distances, angles 242and torsion angles; correlations between e.s.d.'s in cell parameters are only 243used when they are defined by crystal symmetry. An approximate (isotropic) 244treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. 245planes.</p></td></tr> 246<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 247<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, conventional 248<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for 249negative <i>F</i><sup>2</sup>. The threshold expression of <i>F</i><sup>2</sup> > 250<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>. 251and is not relevant to the choice of reflections for refinement. 252<i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically about twice as large 253as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be 254even larger.</p></td></tr></table> 255</div> 256 257</div> 258<!-- endspecialdetailsdiv --> 259 260<div class="tablewrapcoords"> 261<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" >F1</td><td class="tabledata" >0.9058 (17)</td><td class="tabledata" >0.4852 (16)</td><td class="tabledata" >0.9973 (8)</td><td class="tabledata" >0.112</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F3</td><td class="tabledata" >0.9270 (13)</td><td class="tabledata" >0.6270 (13)</td><td class="tabledata" >0.8772 (6)</td><td class="tabledata" >0.083</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F2</td><td class="tabledata" >1.0892 (15)</td><td class="tabledata" >0.4013 (14)</td><td class="tabledata" >0.9084 (6)</td><td class="tabledata" >0.101</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F1'</td><td class="tabledata" >0.7985 (16)</td><td class="tabledata" >0.6070 (16)</td><td class="tabledata" >0.9651 (7)</td><td class="tabledata" >0.111</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F2'</td><td class="tabledata" >1.000 (2)</td><td class="tabledata" >0.4376 (16)</td><td class="tabledata" >0.9758 (7)</td><td class="tabledata" >0.111</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F3'</td><td class="tabledata" >0.9991 (17)</td><td class="tabledata" >0.5461 (16)</td><td class="tabledata" >0.8769 (7)</td><td class="tabledata" >0.115</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F4</td><td class="tabledata" >0.5055 (13)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0158 (14)</td><td class="tabledata" >0.9651 (7)</td><td class="tabledata" >0.085</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F5</td><td class="tabledata" >0.3781 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0926 (12)</td><td class="tabledata" >0.8429 (6)</td><td class="tabledata" >0.080</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F6</td><td class="tabledata" >0.6975 (13)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0918 (12)</td><td class="tabledata" >0.8664 (6)</td><td class="tabledata" >0.078</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F4'</td><td class="tabledata" >0.5831 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0443 (15)</td><td class="tabledata" >0.9665 (8)</td><td class="tabledata" >0.097</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F5'</td><td class="tabledata" >0.3083 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0556 (14)</td><td class="tabledata" >0.8707 (6)</td><td class="tabledata" >0.095</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >F6'</td><td class="tabledata" >0.6174 (16)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1374 (14)</td><td class="tabledata" >0.8609 (7)</td><td class="tabledata" >0.093</td><td class="tabledata" >0.50</td></tr><tr><td class="tabledata" >N</td><td class="tabledata" >0.3387 (7)</td><td class="tabledata" >0.3503 (6)</td><td class="tabledata" >0.6045 (3)</td><td class="tabledata" >0.0464 (12)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H0A</td><td class="tabledata" >0.2534</td><td class="tabledata" >0.2888</td><td class="tabledata" >0.5744</td><td class="tabledata" >0.056*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C1</td><td class="tabledata" >0.8859 (12)</td><td class="tabledata" >0.4933 (11)</td><td class="tabledata" >0.9164 (5)</td><td class="tabledata" >0.081</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C2</td><td class="tabledata" >0.5244 (14)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0104 (14)</td><td class="tabledata" >0.8816 (5)</td><td class="tabledata" >0.094 (3)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C3</td><td class="tabledata" >0.5326 (11)</td><td class="tabledata" >0.1454 (10)</td><td class="tabledata" >0.8548 (4)</td><td class="tabledata" >0.063 (2)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C4</td><td class="tabledata" >0.4157 (10)</td><td class="tabledata" >0.2037 (8)</td><td class="tabledata" >0.7869 (4)</td><td class="tabledata" >0.0543 (17)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H4A</td><td class="tabledata" >0.3136</td><td class="tabledata" >0.1408</td><td class="tabledata" >0.7574</td><td class="tabledata" >0.065*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C5</td><td class="tabledata" >0.4445 (9)</td><td class="tabledata" >0.3611 (9)</td><td class="tabledata" >0.7587 (4)</td><td class="tabledata" >0.0527 (16)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C6</td><td class="tabledata" >0.5931 (11)</td><td class="tabledata" >0.4465 (10)</td><td class="tabledata" >0.8000 (4)</td><td class="tabledata" >0.072 (2)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H6A</td><td class="tabledata" >0.6137</td><td class="tabledata" >0.5488</td><td class="tabledata" >0.7821</td><td class="tabledata" >0.087*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C7</td><td class="tabledata" >0.7249 (13)</td><td class="tabledata" >0.3856 (12)</td><td class="tabledata" >0.8723 (5)</td><td class="tabledata" >0.080 (2)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C8</td><td class="tabledata" >0.6962 (12)</td><td class="tabledata" >0.2426 (12)</td><td class="tabledata" >0.8978 (5)</td><td class="tabledata" >0.079 (3)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8A</td><td class="tabledata" >0.7817</td><td class="tabledata" >0.2026</td><td class="tabledata" >0.9441</td><td class="tabledata" >0.095*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C9</td><td class="tabledata" >0.3017 (8)</td><td class="tabledata" >0.4239 (8)</td><td class="tabledata" >0.6855 (3)</td><td class="tabledata" >0.0482 (15)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9A</td><td class="tabledata" >0.3274</td><td class="tabledata" >0.5377</td><td class="tabledata" >0.6823</td><td class="tabledata" >0.058*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C10</td><td class="tabledata" >0.0783 (9)</td><td class="tabledata" >0.4033 (9)</td><td class="tabledata" >0.6903 (4)</td><td class="tabledata" >0.0646 (19)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10A</td><td class="tabledata" >0.0507</td><td class="tabledata" >0.4508</td><td class="tabledata" >0.7405</td><td class="tabledata" >0.097*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10B</td><td class="tabledata" >0.0461</td><td class="tabledata" >0.2926</td><td class="tabledata" >0.6902</td><td class="tabledata" >0.097*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10C</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0033</td><td class="tabledata" >0.4535</td><td class="tabledata" >0.6433</td><td class="tabledata" >0.097*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C11</td><td class="tabledata" >0.5373 (9)</td><td class="tabledata" >0.3961 (9)</td><td class="tabledata" >0.5832 (4)</td><td class="tabledata" >0.0606 (18)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H11A</td><td class="tabledata" >0.5542</td><td class="tabledata" >0.3455</td><td class="tabledata" >0.5323</td><td class="tabledata" >0.091*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H11B</td><td class="tabledata" >0.6447</td><td class="tabledata" >0.3636</td><td class="tabledata" >0.6269</td><td class="tabledata" >0.091*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H11C</td><td class="tabledata" >0.5419</td><td class="tabledata" >0.5088</td><td class="tabledata" >0.5766</td><td class="tabledata" >0.091*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O1</td><td class="tabledata" >0.6777 (8)</td><td class="tabledata" >0.0742 (7)</td><td class="tabledata" >0.6474 (4)</td><td class="tabledata" >0.0869 (18)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O2</td><td class="tabledata" >0.5220 (7)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1471 (5)</td><td class="tabledata" >0.6689 (3)</td><td class="tabledata" >0.0652 (13)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2A</td><td class="tabledata" >0.4226</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0912</td><td class="tabledata" >0.6526</td><td class="tabledata" >0.098*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O3</td><td class="tabledata" >0.8263 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.2740 (5)</td><td class="tabledata" >0.5576 (3)</td><td class="tabledata" >0.0579 (12)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H3A</td><td class="tabledata" >0.8825</td><td class="tabledata" ><span style="font-family:Times">−</span>0.3437</td><td class="tabledata" >0.5351</td><td class="tabledata" >0.087*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O4</td><td class="tabledata" >1.1965 (6)</td><td class="tabledata" >0.0264 (5)</td><td class="tabledata" >0.6157 (3)</td><td class="tabledata" >0.0540 (11)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O5</td><td class="tabledata" >0.9516 (7)</td><td class="tabledata" >0.0076 (6)</td><td class="tabledata" >0.5086 (3)</td><td class="tabledata" >0.0678 (15)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H5A</td><td class="tabledata" >1.0184</td><td class="tabledata" >0.0743</td><td class="tabledata" >0.4888</td><td class="tabledata" >0.102*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C12</td><td class="tabledata" >0.6858 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0671 (9)</td><td class="tabledata" >0.6676 (4)</td><td class="tabledata" >0.0551 (17)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C13</td><td class="tabledata" >0.8797 (9)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1508 (8)</td><td class="tabledata" >0.6891 (4)</td><td class="tabledata" >0.0522 (15)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H13A</td><td class="tabledata" >0.8587</td><td class="tabledata" ><span style="font-family:Times">−</span>0.2481</td><td class="tabledata" >0.7179</td><td class="tabledata" >0.063*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H13B</td><td class="tabledata" >0.9744</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0857</td><td class="tabledata" >0.7265</td><td class="tabledata" >0.063*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C14</td><td class="tabledata" >0.9715 (8)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1898 (7)</td><td class="tabledata" >0.6122 (3)</td><td class="tabledata" >0.0428 (14)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H14A</td><td class="tabledata" >1.0894</td><td class="tabledata" ><span style="font-family:Times">−</span>0.2588</td><td class="tabledata" >0.6292</td><td class="tabledata" >0.051*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C15</td><td class="tabledata" >1.0461 (9)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0360 (7)</td><td class="tabledata" >0.5766 (4)</td><td class="tabledata" >0.0464 (15)</td><td class="tabledata" ></td></tr></table> 262</div> 263<!-- endtablewrapcoordsdiv --> 264<div class="tablewrapadps"> 265<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" >F1</td><td class="tabledata" >0.112</td><td class="tabledata" >0.112</td><td class="tabledata" >0.112</td><td class="tabledata" >0.000</td><td class="tabledata" >0.020</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F3</td><td class="tabledata" >0.083</td><td class="tabledata" >0.083</td><td class="tabledata" >0.083</td><td class="tabledata" >0.000</td><td class="tabledata" >0.015</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F2</td><td class="tabledata" >0.101</td><td class="tabledata" >0.101</td><td class="tabledata" >0.101</td><td class="tabledata" >0.000</td><td class="tabledata" >0.018</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F1'</td><td class="tabledata" >0.111</td><td class="tabledata" >0.111</td><td class="tabledata" >0.111</td><td class="tabledata" >0.000</td><td class="tabledata" >0.019</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F2'</td><td class="tabledata" >0.111</td><td class="tabledata" >0.111</td><td class="tabledata" >0.111</td><td class="tabledata" >0.000</td><td class="tabledata" >0.019</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F3'</td><td class="tabledata" >0.115</td><td class="tabledata" >0.115</td><td class="tabledata" >0.115</td><td class="tabledata" >0.000</td><td class="tabledata" >0.020</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F4</td><td class="tabledata" >0.085</td><td class="tabledata" >0.085</td><td class="tabledata" >0.085</td><td class="tabledata" >0.000</td><td class="tabledata" >0.015</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F5</td><td class="tabledata" >0.080</td><td class="tabledata" >0.080</td><td class="tabledata" >0.080</td><td class="tabledata" >0.000</td><td class="tabledata" >0.014</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F6</td><td class="tabledata" >0.078</td><td class="tabledata" >0.078</td><td class="tabledata" >0.078</td><td class="tabledata" >0.000</td><td class="tabledata" >0.014</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F4'</td><td class="tabledata" >0.097</td><td class="tabledata" >0.097</td><td class="tabledata" >0.097</td><td class="tabledata" >0.000</td><td class="tabledata" >0.017</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F5'</td><td class="tabledata" >0.095</td><td class="tabledata" >0.095</td><td class="tabledata" >0.095</td><td class="tabledata" >0.000</td><td class="tabledata" >0.017</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >F6'</td><td class="tabledata" >0.093</td><td class="tabledata" >0.093</td><td class="tabledata" >0.093</td><td class="tabledata" >0.000</td><td class="tabledata" >0.016</td><td class="tabledata" >0.000</td></tr><tr><td class="tabledata" >N</td><td class="tabledata" >0.050 (3)</td><td class="tabledata" >0.044 (3)</td><td class="tabledata" >0.047 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.015 (3)</td><td class="tabledata" >0.010 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.004 (3)</td></tr><tr><td class="tabledata" >C1</td><td class="tabledata" >0.072</td><td class="tabledata" >0.100</td><td class="tabledata" >0.067</td><td class="tabledata" ><span style="font-family:Times">−</span>0.033</td><td class="tabledata" ><span style="font-family:Times">−</span>0.003</td><td class="tabledata" >0.033</td></tr><tr><td class="tabledata" >C2</td><td class="tabledata" >0.097 (7)</td><td class="tabledata" >0.114 (8)</td><td class="tabledata" >0.069 (6)</td><td class="tabledata" >0.014 (7)</td><td class="tabledata" >0.012 (5)</td><td class="tabledata" >0.000 (6)</td></tr><tr><td class="tabledata" >C3</td><td class="tabledata" >0.063 (4)</td><td class="tabledata" >0.065 (5)</td><td class="tabledata" >0.059 (4)</td><td class="tabledata" >0.016 (4)</td><td class="tabledata" >0.005 (4)</td><td class="tabledata" >0.000 (4)</td></tr><tr><td class="tabledata" >C4</td><td class="tabledata" >0.055 (4)</td><td class="tabledata" >0.058 (4)</td><td class="tabledata" >0.048 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.002 (4)</td><td class="tabledata" >0.002 (3)</td><td class="tabledata" >0.002 (3)</td></tr><tr><td class="tabledata" >C5</td><td class="tabledata" >0.053 (4)</td><td class="tabledata" >0.065 (5)</td><td class="tabledata" >0.042 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.004 (4)</td><td class="tabledata" >0.013 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.002 (3)</td></tr><tr><td class="tabledata" >C6</td><td class="tabledata" >0.075 (5)</td><td class="tabledata" >0.084 (6)</td><td class="tabledata" >0.055 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.014 (5)</td><td class="tabledata" >0.003 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.012 (4)</td></tr><tr><td class="tabledata" >C7</td><td class="tabledata" >0.068 (5)</td><td class="tabledata" >0.076 (6)</td><td class="tabledata" >0.089 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.003 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.006 (4)</td><td class="tabledata" >0.001 (5)</td></tr><tr><td class="tabledata" >C8</td><td class="tabledata" >0.068 (5)</td><td class="tabledata" >0.102 (7)</td><td class="tabledata" >0.061 (5)</td><td class="tabledata" >0.000 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.007 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.014 (5)</td></tr><tr><td class="tabledata" >C9</td><td class="tabledata" >0.053 (3)</td><td class="tabledata" >0.045 (3)</td><td class="tabledata" >0.045 (3)</td><td class="tabledata" >0.009 (3)</td><td class="tabledata" >0.003 (3)</td><td class="tabledata" >0.007 (3)</td></tr><tr><td class="tabledata" >C10</td><td class="tabledata" >0.054 (4)</td><td class="tabledata" >0.069 (5)</td><td class="tabledata" >0.073 (4)</td><td class="tabledata" >0.005 (4)</td><td class="tabledata" >0.017 (3)</td><td class="tabledata" >0.014 (4)</td></tr><tr><td class="tabledata" >C11</td><td class="tabledata" >0.047 (3)</td><td class="tabledata" >0.062 (4)</td><td class="tabledata" >0.072 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.015 (3)</td><td class="tabledata" >0.010 (3)</td><td class="tabledata" >0.003 (4)</td></tr><tr><td class="tabledata" >O1</td><td class="tabledata" >0.081 (4)</td><td class="tabledata" >0.067 (4)</td><td class="tabledata" >0.120 (5)</td><td class="tabledata" >0.011 (3)</td><td class="tabledata" >0.037 (3)</td><td class="tabledata" >0.010 (4)</td></tr><tr><td class="tabledata" >O2</td><td class="tabledata" >0.068 (3)</td><td class="tabledata" >0.053 (3)</td><td class="tabledata" >0.074 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.002 (3)</td><td class="tabledata" >0.009 (2)</td><td class="tabledata" >0.002 (3)</td></tr><tr><td class="tabledata" >O3</td><td class="tabledata" >0.059 (3)</td><td class="tabledata" >0.043 (2)</td><td class="tabledata" >0.074 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.012 (2)</td><td class="tabledata" >0.018 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.011 (2)</td></tr><tr><td class="tabledata" >O4</td><td class="tabledata" >0.046 (2)</td><td class="tabledata" >0.053 (3)</td><td class="tabledata" >0.062 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.011 (2)</td><td class="tabledata" >0.009 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.002 (2)</td></tr><tr><td class="tabledata" >O5</td><td class="tabledata" >0.082 (3)</td><td class="tabledata" >0.066 (3)</td><td class="tabledata" >0.052 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.022 (3)</td><td class="tabledata" >0.003 (2)</td><td class="tabledata" >0.015 (3)</td></tr><tr><td class="tabledata" >C12</td><td class="tabledata" >0.062 (4)</td><td class="tabledata" >0.061 (4)</td><td class="tabledata" >0.046 (4)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.003 (4)</td><td class="tabledata" >0.022 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.005 (3)</td></tr><tr><td class="tabledata" >C13</td><td class="tabledata" >0.060 (4)</td><td class="tabledata" >0.051 (4)</td><td class="tabledata" >0.048 (3)</td><td class="tabledata" >0.005 (4)</td><td class="tabledata" >0.016 (3)</td><td class="tabledata" >0.003 (3)</td></tr><tr><td class="tabledata" >C14</td><td class="tabledata" >0.041 (3)</td><td class="tabledata" >0.048 (4)</td><td class="tabledata" >0.042 (3)</td><td class="tabledata" >0.007 (3)</td><td class="tabledata" >0.014 (3)</td><td class="tabledata" >0.006 (3)</td></tr><tr><td class="tabledata" >C15</td><td class="tabledata" >0.046 (3)</td><td class="tabledata" >0.036 (3)</td><td class="tabledata" >0.061 (4)</td><td class="tabledata" >0.005 (3)</td><td class="tabledata" >0.020 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.004 (3)</td></tr></table> 266</div> 267<!-- endtablewrapadpsdiv --> 268<div class="tablewrapgeomlong"> 269<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"> 270<colgroup span="4"> 271<col width="30%"></col> 272<col width="20%"></col> 273<col width="30%"></col> 274<col width="20%"></col> 275</colgroup> 276<tr><td width="30%" class="tabledata" >F1—C1</td><td width="20%" class="tabledata" >1.309 (14)</td><td width="30%" class="tabledata" >C7—C8</td><td width="20%" class="tabledata" >1.304 (13)</td></tr><tr><td width="30%" class="tabledata" >F3—C1</td><td width="20%" class="tabledata" >1.352 (13)</td><td width="30%" class="tabledata" >C8—H8A</td><td width="20%" class="tabledata" >0.9300</td></tr><tr><td width="30%" class="tabledata" >F2—C1</td><td width="20%" class="tabledata" >1.589 (14)</td><td width="30%" class="tabledata" >C9—C10</td><td width="20%" class="tabledata" >1.517 (8)</td></tr><tr><td width="30%" class="tabledata" >F1'—C1</td><td width="20%" class="tabledata" >1.436 (13)</td><td width="30%" class="tabledata" >C9—H9A</td><td width="20%" class="tabledata" >0.9800</td></tr><tr><td width="30%" class="tabledata" >F2'—C1</td><td width="20%" class="tabledata" >1.219 (13)</td><td width="30%" class="tabledata" >C10—H10A</td><td width="20%" class="tabledata" >0.9600</td></tr><tr><td width="30%" class="tabledata" >F3'—C1</td><td width="20%" class="tabledata" >1.167 (12)</td><td width="30%" class="tabledata" >C10—H10B</td><td width="20%" class="tabledata" >0.9600</td></tr><tr><td width="30%" class="tabledata" >F4—C2</td><td width="20%" class="tabledata" >1.395 (13)</td><td width="30%" class="tabledata" >C10—H10C</td><td width="20%" class="tabledata" >0.9600</td></tr><tr><td width="30%" class="tabledata" >F5—C2</td><td width="20%" class="tabledata" >1.274 (12)</td><td width="30%" class="tabledata" >C11—H11A</td><td width="20%" class="tabledata" >0.9600</td></tr><tr><td width="30%" class="tabledata" >F6—C2</td><td width="20%" class="tabledata" >1.404 (11)</td><td width="30%" class="tabledata" >C11—H11B</td><td width="20%" class="tabledata" >0.9600</td></tr><tr><td width="30%" class="tabledata" >F4'—C2</td><td width="20%" class="tabledata" >1.405 (14)</td><td width="30%" class="tabledata" >C11—H11C</td><td width="20%" class="tabledata" >0.9600</td></tr><tr><td width="30%" class="tabledata" >F5'—C2</td><td width="20%" class="tabledata" >1.474 (13)</td><td width="30%" class="tabledata" >O1—C12</td><td width="20%" class="tabledata" >1.237 (9)</td></tr><tr><td width="30%" class="tabledata" >F6'—C2</td><td width="20%" class="tabledata" >1.313 (15)</td><td width="30%" class="tabledata" >O2—C12</td><td width="20%" class="tabledata" >1.290 (8)</td></tr><tr><td width="30%" class="tabledata" >N—C11</td><t…
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