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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 2008" /> 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 src="http://www.google-analytics.com/urchin.js" type="text/javascript"></script><script type="text/javascript"> 17_uacct = "UA-187984-3"; 18urchinTracker(); 19</script><link href="../../../../../styles/publcif.css" rel="stylesheet" type="text/css" /></head> 20<body bgcolor="#FFFFFF" text="#000000" > 21<a name="top"></a><h1 class="suptitle">supplementary materials</h1><br /><div class="buttonlinks"><a href="./index.html" target="_parent"><img src="../../../../../graphics/htmlborder.gif" alt="HTML version" align="top" border="0" /></a><a href="./at2619.pdf" ><img src="../../../../../graphics/pdfborder.gif" alt="pdf version" align="top" border="0" /></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?at2619sup1" ><img src="../../../../../graphics/cifborder.gif" alt="cif file" align="top" border="0" /></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?at2619sup1&Qmime=cif" ><img src="../../../../../graphics/3dviewborder.gif" alt="3d view" align="top" border="0" /></a><a href="./at2619Isup2.hkl" ><img src="../../../../../graphics/structurefactorsborder.gif" alt="structure factors" align="top" border="0" /></a><a href="./at2619sup0.html" ><img src="../../../../../graphics/supplementarymaterialsborder.gif" alt="supplementary materials" align="top" border="0" /></a><a href="./at2619checkcif.html" ><img src="../../../../../graphics/checkcifborder.gif" alt="CIF check report" align="top" border="0" /></a><a href="http://scripts.iucr.org/cgi-bin/similar?wordList=trifluoromethyl%20or%20hexahydropyrimidine&from=at2619" ><img src="../../../../../graphics/similarpapersborder.gif" alt="similar papers" align="top" border="0" /></a> <a href="../../../../../../services/openaccess.html"><img src="../../../../../../logos/free.gif" alt="Open access" align="top" border="0" /></a></div><p class="scheme"><img src="./at2619contents.gif" alt="at2619 scheme" /></p><div class="bibline"><p><i>Acta Cryst.</i> (2008). E<b>64</b>, o1840-o1841 [ <font size="2"><a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536808027232">doi:10.1107/S1600536808027232</a></font> ]</p></div> 22<h3>2-[2-Chloro-5-(trifluoromethyl)phenyl]hexahydropyrimidine monohydrate</h3><h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Fun,%20H.-K.">H.-K. Fun</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Kia,%20R.">R. Kia</a></h3> 23<div class="abstract"> 24<a name="abstract"></a> 25<div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 26</div> 27<!-- endheading2div --><p>The molecule of the title compound, C<span class="inf"><sub>11</sub></span>H<span class="inf"><sub>12</sub></span>ClF<span class="inf"><sub>3</sub></span>N<span class="inf"><sub>2</sub></span>·H<span class="inf"><sub>2</sub></span>O, is a substituted hexahydropyrimidine. There are two crystallographically independent molecules (<span class="it"><i>A</i></span> and <span class="it"><i>B</i></span>) and two water molecules in the asymmetric unit of the title compound. Intermolecular C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />Cl (× 2), C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />F, and C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />N (× 2) hydrogen bonds generate <span class="it"><i>S</i></span>(5) ring motifs. The dihedral angle between the two benzene rings is 8.17 (11)°. The F atoms in molecule <span class="it"><i>B</i></span> are disordered over four positions with refined site-occupancies of <span class="it"><i>ca</i></span> 0.35/0.19/0.29/0.17 for the four components. In the crystal structure, molecules are arranged into one-dimensional extended chains along the <span class="it"><i>c</i></span> axis and are further stacked along the <span class="it"><i>a</i></span> axis by directed four-membered O-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />O-H interactions, forming two-dimensional networks parallel to the <span class="it"><i>ac</i></span> plane. The short distances between the centroids of the benzene rings (3.8002-3.8327 Å) indicate the existence of <img alt="[pi]" border="0" src="/logos/entities/pi_rmgif.gif" />-<img alt="[pi]" border="0" src="/logos/entities/pi_rmgif.gif" /> interactions. In addition, the crystal structure is further stabilized by N-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />O, O-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />N (× 4), N-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />Cl and C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />O (× 2) hydrogen-bonding interactions.</p></div> 28<!-- endabstractdiv --> 29 30 31 32 33 34<div class="contentslist"> 35<ul> 36<li class="comment"><a title="Comment" href="#comment">Comment</a></li> 37<li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li> 38<li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li> 39<li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li> 40<li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li> 41<li class="figures"><a title="Figures" href="#figures">Figures</a></li> 42<li><a title="(I)" href="#chemicalname1">2-[2-Chloro-5-(trifluoromethyl)phenyl]hexahydropyrimidine monohydrate </a><ul> 43<li><a title="Crystal data" href="#crystaldata1">Crystal data</a></li> 44<li><a title="Data collection" href="#datacollection1">Data collection</a></li> 45<li><a title="Refinement data" href="#refinementdata1">Refinement data</a></li> 46<li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li> 47<li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic coordinates</a></li> 48<li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li> 49<li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li> 50<li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 51<li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 52</ul></li> 53<li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li> 54<li class="publreferences"><a title="References" href="#publreferences">References</a></li> 55</ul> 56</div> 57<!-- endcontentslistdiv --> 58 59<div class="comment"> 60<a name="comment"></a> 61<div class="heading2"> 62Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 63</div> 64<!-- endheading2div --><p>Hexahydropyrimidines are prepared classically by condensations of substituted 65propane-1,3-diamines with aldehydes and ketones. Hexahydropyrimidines are 66biologically important. <i>N,N'</i>-Bisalkylhexahydro pyrimidines are 67effective against Ehrlich carcinoma, LK lymphoma, and Staphylococcus aureus. 68The hexahydropyrimidine skeleton occurs in alkaloids such as verbamethine and 69verbametrine. <i>N</i>-Substituted hexahydropyrimidines are synthetic 70intermediates for recently discovered spermidine-nitroimidazole drugs for the 71treatment of A549 lung carcinoma and structural units in new trypanothione 72reductase inhibiting ligands for the regulation of oxidative stress in 73parasitic cells. Benzo-fused hexahydropyrimidines or 741,2,3,4-tetrahydroquinazolines are potential <i>R</i>-adrenergic blockers and 75possess antiplatelet activity.</p><p>In the title compound (I) (Fig. 1), intramolecular C—H···Cl (<i>x</i> 2), 76C—H···F, and C—H···N (<i>x</i> 2) hydrogen bonds generate <i>S</i>(5) ring 77motifs (Bernstein <i>et al.</i>, 1995). The bond lengths and angles are 78within 79normal ranges (Allen <i>et al.</i>, 1987). There are two 80crystallographically 81independent molecules (A, and B) and two water molecules in the asymmetric 82unit of the title compound. The dihedral angle between the two benzene rings 83is 8.17 (11)°. The pyrimidine rings in molecules A and B adopt chair 84conformation with the puckering parameter (Cremer & Pople, 1975) 85Q=0.603 (3)°; 86<span style="font-family:Times">θ</span>=1.2 (3)°; <span style="font-family:Times">φ</span>=31 (9)° for ring A and Q=0.601 (3)°; <span style="font-family:Times">θ</span>=2.5 (3)°; <span style="font-family:Times">φ</span>=48 (6)° 87for ring B. The CF<sub>3</sub> fragment in molecule B, was disordered over four 88positions with the refined site-occupancies of 890.351 (7)/0.189 (5)/0.289 (9)/0.168 (6) for these four components, respectively. 90In the crystal structure, molecules are arranged into 1-D extended chains along 91the <i>c</i>-axis and are further stacked along the <i>a</i>-axis by directed 92four-membered O—H···O—H interactions to form 2-D networks which is 93parralell to <i>ac</i>-plane. The short distances between the centroids of the 94benzene rings prove an existence of <span style="font-family:Times">π</span>-<span style="font-family:Times">π</span> interactions with distances of 953.8002–3.8327 Å. In addition, the crystal structure is further stabilized 96by N—H···O, O—H···N (<i>x</i> 4), N—H···Cl, and C—H···O (<i>x</i> 2) 97hydrogen bonding interactions.</p> 98</div> 99<!-- endcommentdiv --> 100 101 102<div class="relatedliterature"> 103<a name="relatedliterature"></a> 104<div class="heading2"> 105Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 106</div> 107<!-- endheading2div --><p>For bond-lengts data, see: Allen <i>et al.</i> (1987). For hydrogen-bond 108motifs, 109see: Bernstein <i>et al.</i> (1995). For ring conformations, see: 110Cremer & 111Pople (1975). For related literature and properties, see, for example: 112Riebsomer & Morey (1950); Finch <i>et al.</i> (1952); Drandarov 113<i>et al.</i> 114(1999); Siddiqui <i>et al.</i> (1999); Horvath (1997); 115Katritzky <i>et al.</i> 116(2002).</p> 117</div> 118<!-- endrelatedliteraturediv --> 119 120 121<div class="experimental"> 122<a name="experimental"></a> 123<div class="heading2"> 124Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 125</div> 126<!-- endheading2div --><p>The title compound was synthesized based on the previous method (Finch <i>et 127al.</i>, 1952). Single crystals suitable for <i>X</i>-ray diffraction 128were 129obtained by evaporation of an ethanol solution at room temperature.</p> 130</div> 131<!-- endexperimentaldiv --> 132 133 134<div class="refinement"> 135<a name="refinement"></a> 136<div class="heading2"> 137Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 138</div> 139<!-- endheading2div --><p>H atoms bound to the N atoms and water molecules were initially found from the 140difference Fourier map and refined freely with the parent atoms. The rest of 141the hydrogen atoms were positioned geometrically and refined as 142riding model with 143<i>U</i><sub>iso</sub>(H) = 1.2 <i>U</i><sub>eq</sub>(C). The disordered fluorine atoms of the 144CF<sub>3</sub> fragment in molecule B were refined isotropically using C—F bonds 145distance restraint of 1.300 (5). Their displacement parameters were restrained 146using rigid bond model.</p> 147</div> 148<!-- endrefinementdiv --> 149 150 151<div class="computingdetails"> 152<a name="computingdetails"></a> 153<div class="heading2"> 154Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 155</div> 156<!-- endheading2div --><p>Data collection: <i>APEX2</i> (Bruker, 2005); cell refinement: <i>APEX2</i>; data reduction: <i>SAINT</i> (Bruker, 2005); program(s) used to solve structure: <i>SHELXTL</i> (Sheldrick, 2008); program(s) used to refine structure: <i>SHELXTL</i> (Sheldrick, 2008); molecular graphics: <i>SHELXTL</i> (Sheldrick, 2008); software used to prepare material for publication: <i>SHELXTL</i> (Sheldrick, 2008) and <i>PLATON</i> (Spek, 2003).</p> 157</div> 158<!-- endcomputingdetailsdiv --> 159 160 161<div class="schemes"> 162<a href="./at2619scheme1.gif"></a> 163</div> 164<!-- endschemesdiv --> 165 166<div class="figures"> 167 168<div class="tablewrap"> 169<a name="figures"></a> 170<div class="heading2"> 171Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 172</div> 173<!-- endheading2div --><table style="table-layout:fixed" width="100%" class="nodecs"> 174<colgroup span="2"> 175<col width="110"></col> 176<col></col> 177</colgroup> 178<tr><td class="nodecs" align="center" width="110"> 179<a href="./at2619fig1.html"><img width="100" src="./at2619fig1thm.gif" alt="[Figure 1]" align="middle"/></a> 180</td><td class="nodecs" valign="middle" > 181<font size="2">Fig. 1. The molecular structure of (I), showing 40% probability displacement 182ellipsoids. For clarity, only hydrogen atoms of the water molecules and those 183H atoms involved in intramolecular and intermolecular interactions (shown as 184dashed lines) were drawn. Open bonds indicate the minor disordered component.</font> 185</td></tr> 186<tr><td class="nodecs" align="center" width="110"> 187<a href="./at2619fig2.html"><img width="100" src="./at2619fig2thm.gif" alt="[Figure 2]" align="middle"/></a> 188</td><td class="nodecs" valign="middle" > 189<font size="2">Fig. 2. The crystal packing of the major component of (I), viewed down the 190<i>a</i>-axis, showing 1-D extended 191chains along the <i>c</i>-axis and stacking of these chains along the 192<i>a</i>-axis. Intra and intermolecular interactions are shown as dashed 193lines.</font> 194</td></tr> 195<tr><td class="nodecs" align="center" width="110"> 196<a href="./at2619fig3.html"><img width="100" src="./at2619fig3thm.gif" alt="[Figure 3]" align="middle"/></a> 197</td><td class="nodecs" valign="middle" > 198<font size="2">Fig. 3. The crystal structure of the major component of (I), showing 1-D extended 199chains along the 200<i>a</i>-axis.</font> 201</td></tr> 202</table> 203</div> 204 205</div> 206<!-- endfiguresdiv --> 207 208<div class="datablock1"> 209 210 211<div class="heading2"> 212<a name="chemicalname1"></a>2-[2-Chloro-5-(trifluoromethyl)phenyl]hexahydropyrimidine monohydrate <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 213</div> 214<!-- endheading2div --> 215 216 217<div class="tablewrapcrystaldatalong"> 218<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"> 219<colgroup span="2"> 220<col width="50%"></col> 221<col width="50%"></col> 222</colgroup> 223<tr><td width="50%" class="tabledata" >C<sub>11</sub>H<sub>12</sub>Cl<sub>1</sub>F<sub>3</sub>N<sub>2</sub>·H<sub>2</sub>O<sub>1</sub></td><td width="50%" class="tabledata" ><i>F</i><sub>000</sub> = 1168</td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 282.69</td><td width="50%" class="tabledata" ><i>D</i><sub>x</sub> = 1.496 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 6400 reflections</td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 7.0745 (2) Å</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span> = 2.4–23.0º</td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 18.6119 (5) Å</td><td width="50%" class="tabledata" >µ = 0.33 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 19.0631 (5) Å</td><td width="50%" class="tabledata" ><i>T</i> = 100.0 (1) K</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">β</span> = 91.010 (2)º</td><td width="50%" class="tabledata" >Block, colourless</td></tr><tr><td width="50%" class="tabledata" ><i>V</i> = 2509.65 (12) Å<sup>3</sup></td><td width="50%" class="tabledata" >0.24 × 0.05 × 0.02 mm</td></tr><tr><td width="50%" class="tabledata" ><i>Z</i> = 8</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 224</div> 225<!-- endtablewrapcrystaldatalongdiv --> 226 227<div class="tablewrapdatacollectionlong"> 228<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"> 229<colgroup span="2"> 230<col width="50%"></col> 231<col width="50%"></col> 232</colgroup> 233<tr><td width="50%" class="tabledata" >Bruker SMART APEXII CCD area-detector <br />diffractometer</td><td width="50%" class="tabledata" >7308 independent reflections</td></tr><tr><td width="50%" class="tabledata" >Radiation source: fine-focus sealed tube</td><td width="50%" class="tabledata" >4995 reflections with <i>I</i> > 2<span style="font-family:Times">σ</span>(<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> = 0.053</td></tr><tr><td width="50%" class="tabledata" ><i>T</i> = 100.0(1) K</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>max</sub> = 30.1º</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> = 2.1º</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: multi-scan<br />(SADABS; Bruker, 2005)</td><td width="50%" class="tabledata" ><i>h</i> = <span style="font-family:Times">−</span>9→9</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.924, <i>T</i><sub>max</sub> = 0.992</td><td width="50%" class="tabledata" ><i>k</i> = <span style="font-family:Times">−</span>26→20</td></tr><tr><td width="50%" class="tabledata" >30107 measured reflections</td><td width="50%" class="tabledata" ><i>l</i> = <span style="font-family:Times">−</span>16→26</td></tr></table><!-- endtabledatatable --> 234</div> 235<!-- endtablewrapdatacollectionlongdiv --> 236 237<div class="tablewraprefinementdatalong"> 238<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"> 239<colgroup span="2"> 240<col width="50%"></col> 241<col width="50%"></col> 242</colgroup> 243<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>)] = 0.064</td><td width="50%" class="tabledata" >H atoms treated by a mixture of<br /> independent and constrained refinement</td></tr><tr><td width="50%" class="tabledata" ><i>wR</i>(<i>F</i><sup>2</sup>) = 0.145</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>) + (0.0411<i>P</i>)<sup>2</sup> + 3.5237<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> = 1.08</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" >7308 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.61 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >379 parameters</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.60 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >41 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 --> 244</div> 245<!-- endtablewraprefinementdatalongdiv --> 246 247<div class="tablewrapcrystaldatashort"> 248<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"> 249<colgroup span="2"> 250<col width="50%"></col> 251<col width="50%"></col> 252</colgroup> 253<tr><td width="50%" class="tabledata" >C<sub>11</sub>H<sub>12</sub>Cl<sub>1</sub>F<sub>3</sub>N<sub>2</sub>·H<sub>2</sub>O<sub>1</sub></td><td width="50%" class="tabledata" ><i>V</i> = 2509.65 (12) Å<sup>3</sup></td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 282.69</td><td width="50%" class="tabledata" ><i>Z</i> = 8</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> = 7.0745 (2) Å</td><td width="50%" class="tabledata" >µ = 0.33 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 18.6119 (5) Å</td><td width="50%" class="tabledata" ><i>T</i> = 100.0 (1) K</td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 19.0631 (5) Å</td><td width="50%" class="tabledata" >0.24 × 0.05 × 0.02 mm</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">β</span> = 91.010 (2)º</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 254</div> 255<!-- endtablewrapcrystaldatashortdiv --> 256 257<div class="tablewrapdatacollectionshort"> 258<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"> 259<colgroup span="2"> 260<col width="50%"></col> 261<col width="50%"></col> 262</colgroup> 263<tr><td width="50%" class="tabledata" >Bruker SMART APEXII CCD area-detector <br />diffractometer</td><td width="50%" class="tabledata" >7308 independent reflections</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: multi-scan<br />(SADABS; Bruker, 2005)</td><td width="50%" class="tabledata" >4995 reflections with <i>I</i> > 2<span style="font-family:Times">σ</span>(<i>I</i>)</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.924, <i>T</i><sub>max</sub> = 0.992</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.053</td></tr><tr><td width="50%" class="tabledata" >30107 measured reflections</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 264</div> 265<!-- endtablewrapdatacollectionshortdiv --> 266 267<div class="tablewraprefinementdatashort"> 268<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"> 269<colgroup span="2"> 270<col width="50%"></col> 271<col width="50%"></col> 272</colgroup> 273<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>)] = 0.064</td><td width="50%" class="tabledata" >41 restraints</td></tr><tr><td width="50%" class="tabledata" ><i>wR</i>(<i>F</i><sup>2</sup>) = 0.145</td><td width="50%" class="tabledata" >H atoms treated by a mixture of<br /> independent and constrained refinement</td></tr><tr><td width="50%" class="tabledata" ><i>S</i> = 1.08</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.61 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >7308 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.60 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >379 parameters</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable --> 274</div> 275<!-- endtablewraprefinementdatashortdiv --> 276<div class="specialdetails"> 277 278<div class="tablewrap"> 279<a name="specialdetails1"></a><span class="heading3">Special details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 280<table style="table-layout:fixed" width="100%" class="tabledata"> 281<tr><td class="tabledata"><p><b>Experimental</b>. The low-temperature data was collected with the Oxford Cyrosystem Cobra 282low-temperature attachment.</p></td></tr> 283<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) 284are estimated using the full covariance matrix. The cell e.s.d.'s are taken 285into account individually in the estimation of e.s.d.'s in distances, angles 286and torsion angles; correlations between e.s.d.'s in cell parameters are only 287used when they are defined by crystal symmetry. An approximate (isotropic) 288treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. 289planes.</p></td></tr> 290<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 291<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, conventional 292<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for 293negative <i>F</i><sup>2</sup>. The threshold expression of <i>F</i><sup>2</sup> > 294<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>. 295and is not relevant to the choice of reflections for refinement. 296<i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically about twice as large 297as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be 298even larger.</p></td></tr></table> 299</div> 300 301</div> 302<!-- endspecialdetailsdiv --> 303 304<div class="tablewrapcoords"> 305<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" >Cl1A</td><td class="tabledata" >0.20441 (9)</td><td class="tabledata" >0.10260 (4)</td><td class="tabledata" >0.33890 (4)</td><td class="tabledata" >0.02426 (16)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >F1A</td><td class="tabledata" >0.1451 (3)</td><td class="tabledata" >0.40379 (9)</td><td class="tabledata" >0.52585 (9)</td><td class="tabledata" >0.0364 (4)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >F2A</td><td class="tabledata" >0.0671 (3)</td><td class="tabledata" >0.44306 (10)</td><td class="tabledata" >0.42408 (11)</td><td class="tabledata" >0.0431 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >F3A</td><td class="tabledata" >0.3579 (2)</td><td class="tabledata" >0.43149 (10)</td><td class="tabledata" >0.45284 (10)</td><td class="tabledata" >0.0382 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >N1A</td><td class="tabledata" >0.0590 (3)</td><td class="tabledata" >0.15070 (12)</td><td class="tabledata" >0.56007 (12)</td><td class="tabledata" >0.0182 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >N2A</td><td class="tabledata" >0.3521 (3)</td><td class="tabledata" >0.10898 (12)</td><td class="tabledata" >0.51715 (12)</td><td class="tabledata" >0.0182 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C1A</td><td class="tabledata" >0.1928 (3)</td><td class="tabledata" >0.18840 (15)</td><td class="tabledata" >0.37603 (14)</td><td class="tabledata" >0.0195 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C2A</td><td class="tabledata" >0.2034 (3)</td><td class="tabledata" >0.24683 (16)</td><td class="tabledata" >0.33062 (14)</td><td class="tabledata" >0.0226 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2AA</td><td class="tabledata" >0.2129</td><td class="tabledata" >0.2397</td><td class="tabledata" >0.2825</td><td class="tabledata" >0.027*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C3A</td><td class="tabledata" >0.1998 (3)</td><td class="tabledata" >0.31528 (16)</td><td class="tabledata" >0.35780 (14)</td><td class="tabledata" >0.0227 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H3AA</td><td class="tabledata" >0.2056</td><td class="tabledata" >0.3548</td><td class="tabledata" >0.3280</td><td class="tabledata" >0.027*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C4A</td><td class="tabledata" >0.1874 (3)</td><td class="tabledata" >0.32524 (14)</td><td class="tabledata" >0.42968 (14)</td><td class="tabledata" >0.0193 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C5A</td><td class="tabledata" >0.1752 (3)</td><td class="tabledata" >0.26648 (14)</td><td class="tabledata" >0.47436 (14)</td><td class="tabledata" >0.0169 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H5AA</td><td class="tabledata" >0.1667</td><td class="tabledata" >0.2739</td><td class="tabledata" >0.5224</td><td class="tabledata" >0.020*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C6A</td><td class="tabledata" >0.1758 (3)</td><td class="tabledata" >0.19653 (14)</td><td class="tabledata" >0.44817 (13)</td><td class="tabledata" >0.0163 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C7A</td><td class="tabledata" >0.1603 (3)</td><td class="tabledata" >0.13238 (14)</td><td class="tabledata" >0.49649 (13)</td><td class="tabledata" >0.0176 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H7AA</td><td class="tabledata" >0.0946</td><td class="tabledata" >0.0932</td><td class="tabledata" >0.4719</td><td class="tabledata" >0.021*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C8A</td><td class="tabledata" >0.0401 (4)</td><td class="tabledata" >0.08749 (15)</td><td class="tabledata" >0.60549 (14)</td><td class="tabledata" >0.0234 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8AA</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0277</td><td class="tabledata" >0.0498</td><td class="tabledata" >0.5805</td><td class="tabledata" >0.028*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8AB</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0309</td><td class="tabledata" >0.1000</td><td class="tabledata" >0.6468</td><td class="tabledata" >0.028*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C9A</td><td class="tabledata" >0.2355 (4)</td><td class="tabledata" >0.06120 (16)</td><td class="tabledata" >0.62705 (15)</td><td class="tabledata" >0.0246 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9AA</td><td class="tabledata" >0.2249</td><td class="tabledata" >0.0184</td><td class="tabledata" >0.6558</td><td class="tabledata" >0.030*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9AB</td><td class="tabledata" >0.3003</td><td class="tabledata" >0.0979</td><td class="tabledata" >0.6545</td><td class="tabledata" >0.030*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C10A</td><td class="tabledata" >0.3474 (4)</td><td class="tabledata" >0.04425 (15)</td><td class="tabledata" >0.56176 (15)</td><td class="tabledata" >0.0240 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10A</td><td class="tabledata" >0.4751</td><td class="tabledata" >0.0300</td><td class="tabledata" >0.5749</td><td class="tabledata" >0.029*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10B</td><td class="tabledata" >0.2883</td><td class="tabledata" >0.0049</td><td class="tabledata" >0.5362</td><td class="tabledata" >0.029*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C11A</td><td class="tabledata" >0.1886 (4)</td><td class="tabledata" >0.40020 (15)</td><td class="tabledata" >0.45793 (15)</td><td class="tabledata" >0.0224 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >Cl1B</td><td class="tabledata" >0.70385 (9)</td><td class="tabledata" >0.13065 (3)</td><td class="tabledata" >0.38275 (3)</td><td class="tabledata" >0.02102 (15)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C11B</td><td class="tabledata" >0.6923 (5)</td><td class="tabledata" >0.43786 (17)</td><td class="tabledata" >0.29294 (17)</td><td class="tabledata" >0.0364 (8)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >F4</td><td class="tabledata" >0.5910 (12)</td><td class="tabledata" >0.4539 (3)</td><td class="tabledata" >0.2403 (5)</td><td class="tabledata" >0.0226 (12)*</td><td class="tabledata" >0.351 (7)</td></tr><tr><td class="tabledata" >F5</td><td class="tabledata" >0.6856 (18)</td><td class="tabledata" >0.4849 (5)</td><td class="tabledata" >0.3431 (5)</td><td class="tabledata" >0.0241 (10)*</td><td class="tabledata" >0.351 (7)</td></tr><tr><td class="tabledata" >F6</td><td class="tabledata" >0.8935 (10)</td><td class="tabledata" >0.4523 (3)</td><td class="tabledata" >0.2682 (4)</td><td class="tabledata" >0.0163 (15)*</td><td class="tabledata" >0.351 (7)</td></tr><tr><td class="tabledata" >F4B</td><td class="tabledata" >0.7521 (16)</td><td class="tabledata" >0.4863 (4)</td><td class="tabledata" >0.3361 (5)</td><td class="tabledata" >0.0226 (12)*</td><td class="tabledata" >0.189 (5)</td></tr><tr><td class="tabledata" >F5B</td><td class="tabledata" >0.716 (2)</td><td class="tabledata" >0.4505 (6)</td><td class="tabledata" >0.2289 (7)</td><td class="tabledata" >0.041 (4)*</td><td class="tabledata" >0.189 (5)</td></tr><tr><td class="tabledata" >F6B</td><td class="tabledata" >0.4747 (12)</td><td class="tabledata" >0.4605 (4)</td><td class="tabledata" >0.2919 (6)</td><td class="tabledata" >0.021 (2)*</td><td class="tabledata" >0.189 (5)</td></tr><tr><td class="tabledata" >F4C</td><td class="tabledata" >0.8220 (14)</td><td class="tabledata" >0.4554 (3)</td><td class="tabledata" >0.2541 (5)</td><td class="tabledata" >0.025 (2)*</td><td class="tabledata" >0.288 (9)</td></tr><tr><td class="tabledata" >F5C</td><td class="tabledata" >0.6978 (15)</td><td class="tabledata" >0.4818 (5)</td><td class="tabledata" >0.3569 (5)</td><td class="tabledata" >0.0241 (10)*</td><td class="tabledata" >0.288 (9)</td></tr><tr><td class="tabledata" >F6C</td><td class="tabledata" >0.5245 (14)</td><td class="tabledata" >0.4566 (3)</td><td class="tabledata" >0.2635 (5)</td><td class="tabledata" >0.027 (2)*</td><td class="tabledata" >0.288 (9)</td></tr><tr><td class="tabledata" >F4D</td><td class="tabledata" >0.639 (2)</td><td class="tabledata" >0.4462 (6)</td><td class="tabledata" >0.2155 (8)</td><td class="tabledata" >0.0226 (12)*</td><td class="tabledata" >0.167 (6)</td></tr><tr><td class="tabledata" >F5D</td><td class="tabledata" >0.619 (2)</td><td class="tabledata" >0.4824 (6)</td><td class="tabledata" >0.3297 (7)</td><td class="tabledata" >0.0241 (10)*</td><td class="tabledata" >0.167 (6)</td></tr><tr><td class="tabledata" >F6D</td><td class="tabledata" >0.866 (2)</td><td class="tabledata" >0.4612 (8)</td><td class="tabledata" >0.2826 (8)</td><td class="tabledata" >0.029 (4)*</td><td class="tabledata" >0.167 (6)</td></tr><tr><td class="tabledata" >N1B</td><td class="tabledata" >0.8534 (3)</td><td class="tabledata" >0.15394 (12)</td><td class="tabledata" >0.20979 (12)</td><td class="tabledata" >0.0178 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >N2B</td><td class="tabledata" >0.5654 (3)</td><td class="tabledata" >0.20191 (12)</td><td class="tabledata" >0.16508 (12)</td><td class="tabledata" >0.0189 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C1B</td><td class="tabledata" >0.6915 (3)</td><td class="tabledata" >0.21978 (14)</td><td class="tabledata" >0.35477 (14)</td><td class="tabledata" >0.0183 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C2B</td><td class="tabledata" >0.6998 (3)</td><td class="tabledata" >0.27234 (15)</td><td class="tabledata" >0.40623 (14)</td><td class="tabledata" >0.0200 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2BA</td><td class="tabledata" >0.7062</td><td class="tabledata" >0.2599</td><td class="tabledata" >0.4535</td><td class="tabledata" >0.024*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C3B</td><td class="tabledata" >0.6985 (4)</td><td class="tabledata" >0.34360 (15)</td><td class="tabledata" >0.38604 (15)</td><td class="tabledata" >0.0230 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H3BA</td><td class="tabledata" >0.7045</td><td class="tabledata" >0.3797</td><td class="tabledata" >0.4197</td><td class="tabledata" >0.028*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C4B</td><td class="tabledata" >0.6883 (4)</td><td class="tabledata" >0.36098 (15)</td><td class="tabledata" >0.31531 (15)</td><td class="tabledata" >0.0226 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C5B</td><td class="tabledata" >0.6763 (3)</td><td class="tabledata" >0.30779 (14)</td><td class="tabledata" >0.26472 (14)</td><td class="tabledata" >0.0204 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H5BA</td><td class="tabledata" >0.6687</td><td class="tabledata" >0.3205</td><td class="tabledata" >0.2176</td><td class="tabledata" >0.024*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C6B</td><td class="tabledata" >0.6756 (3)</td><td class="tabledata" >0.23534 (14)</td><td class="tabledata" >0.28350 (13)</td><td class="tabledata" >0.0167 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C7B</td><td class="tabledata" >0.6615 (3)</td><td class="tabledata" >0.17660 (14)</td><td class="tabledata" >0.22863 (14)</td><td class="tabledata" >0.0181 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H7BA</td><td class="tabledata" >0.5927</td><td class="tabledata" >0.1355</td><td class="tabledata" >0.2477</td><td class="tabledata" >0.022*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C8B</td><td class="tabledata" >0.8473 (4)</td><td class="tabledata" >0.09305 (15)</td><td class="tabledata" >0.16030 (15)</td><td class="tabledata" >0.0241 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8BA</td><td class="tabledata" >0.7840</td><td class="tabledata" >0.0524</td><td class="tabledata" >0.1814</td><td class="tabledata" >0.029*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8BB</td><td class="tabledata" >0.9748</td><td class="tabledata" >0.0785</td><td class="tabledata" >0.1488</td><td class="tabledata" >0.029*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C9B</td><td class="tabledata" >0.7411 (4)</td><td class="tabledata" >0.11657 (15)</td><td class="tabledata" >0.09448 (15)</td><td class="tabledata" >0.0243 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9BA</td><td class="tabledata" >0.8109</td><td class="tabledata" >0.1544</td><td class="tabledata" >0.0714</td><td class="tabledata" >0.029*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9BB</td><td class="tabledata" >0.7294</td><td class="tabledata" >0.0764</td><td class="tabledata" >0.0623</td><td class="tabledata" >0.029*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C10B</td><td class="tabledata" >0.5465 (4)</td><td class="tabledata" >0.14364 (15)</td><td class="tabledata" >0.11302 (16)</td><td class="tabledata" >0.0251 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10C</td><td class="tabledata" >0.4817</td><td class="tabledata" >0.1613</td><td class="tabledata" >0.0712</td><td class="tabledata" >0.030*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H10D</td><td class="tabledata" >0.4723</td><td class="tabledata" >0.1047</td><td class="tabledata" >0.1322</td><td class="tabledata" >0.030*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O1W</td><td class="tabledata" >0.3328 (3)</td><td class="tabledata" >0.80736 (12)</td><td class="tabledata" >0.43314 (11)</td><td class="tabledata" >0.0258 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O2W</td><td class="tabledata" >0.1595 (3)</td><td class="tabledata" >0.24257 (12)</td><td class="tabledata" >0.16075 (11)</td><td class="tabledata" >0.0240 (4)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H1NA</td><td class="tabledata" ><span style="font-family:Times">−</span>0.054 (5)</td><td class="tabledata" >0.1675 (17)</td><td class="tabledata" >0.5461 (17)</td><td class="tabledata" >0.034 (9)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2NA</td><td class="tabledata" >0.410 (5)</td><td class="tabledata" >0.0988 (19)</td><td class="tabledata" >0.478 (2)</td><td class="tabledata" >0.046 (11)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H1NB</td><td class="tabledata" >0.908 (4)</td><td class="tabledata" >0.1397 (17)</td><td class="tabledata" >0.2501 (17)</td><td class="tabledata" >0.029 (9)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2NB</td><td class="tabledata" >0.457 (5)</td><td class="tabledata" >0.2150 (17)</td><td class="tabledata" >0.1772 (16)</td><td class="tabledata" >0.028 (8)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H1W1</td><td class="tabledata" >0.370 (5)</td><td class="tabledata" >0.777 (2)</td><td class="tabledata" >0.402 (2)</td><td class="tabledata" >0.053 (12)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2W1</td><td class="tabledata" >0.440 (5)</td><td class="tabledata" >0.8277 (19)</td><td class="tabledata" >0.4430 (18)</td><td class="tabledata" >0.037 (10)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H1W2</td><td class="tabledata" >0.056 (5)</td><td class="tabledata" >0.2231 (18)</td><td class="tabledata" >0.1680 (18)</td><td class="tabledata" >0.035 (9)*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2W2</td><td class="tabledata" >0.131 (5)</td><td class="tabledata" >0.277 (2)</td><td class="tabledata" >0.1315 (19)</td><td class="tabledata" >0.043 (11)*</td><td class="tabledata" ></td></tr></table> 306</div> 307<!-- endtablewrapcoordsdiv --> 308<div class="tablewrapadps"> 309<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" >Cl1A</td><td class="tabledata" >0.0223 (3)</td><td class="tabledata" >0.0306 (4)</td><td class="tabledata" >0.0199 (3)</td><td class="tabledata" >0.0021 (3)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0001 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0072 (3)</td></tr><tr><td class="tabledata" >F1A</td><td class="tabledata" >0.0535 (11)</td><td class="tabledata" >0.0211 (9)</td><td class="tabledata" >0.0352 (11)</td><td class="tabledata" >0.0018 (8)</td><td class="tabledata" >0.0155 (9)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0009 (8)</td></tr><tr><td class="tabledata" >F2A</td><td class="tabledata" >0.0460 (11)</td><td class="tabledata" >0.0220 (10)</td><td class="tabledata" >0.0606 (14)</td><td class="tabledata" >0.0058 (8)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0230 (10)</td><td class="tabledata" >0.0078 (9)</td></tr><tr><td class="tabledata" >F3A</td><td class="tabledata" >0.0254 (9)</td><td class="tabledata" >0.0295 (10)</td><td class="tabledata" >0.0599 (13)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0107 (7)</td><td class="tabledata" >0.0116 (8)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0090 (9)</td></tr><tr><td class="tabledata" >N1A</td><td class="tabledata" >0.0174 (10)</td><td class="tabledata" >0.0182 (12)</td><td class="tabledata" >0.0192 (11)</td><td class="tabledata" >0.0007 (8)</td><td class="tabledata" >0.0042 (8)</td><td class="tabledata" >0.0018 (9)</td></tr><tr><td class="tabledata" >N2A</td><td class="tabledata" >0.0168 (10)</td><td class="tabledata" >0.0200 (12)</td><td class="tabledata" >0.0180 (12)</td><td class="tabledata" >0.0028 (8)</td><td class="tabledata" >0.0025 (8)</td><td class="tabledata" >0.0027 (9)</td></tr><tr><td class="tabledata" >C1A</td><td class="tabledata" >0.0153 (11)</td><td class="tabledata" >0.0243 (14)</td><td class="tabledata" >0.0188 (13)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0012 (10)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0013 (9)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0022 (11)</td></tr><tr><td class="tabledata" >C2A</td><td class="tabledata" >0.0179 (12)</td><td class="tabledata" >0.0352 (17)</td><td class="tabledata" >0.0146 (13)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0008 (11)</td><td class="tabledata" >0.0013 (10)</td><td class="tabledata" >0.0029 (12)</td></tr><tr><td class="tabledata" >C3A</td><td class="tabledata" >0.0185 (12)</td><td class="tabledata" >0.0286 (16)</td><td class="tabledata" >0.0209 (14)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0020 (10)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0018 (10)</td><td class="tabledata" >0.0100 (12)</td></tr><tr><td class="tabledata" >C4A</td><td class="tabledata" >0.0142 (11)</td><td class="tabledata" >0.0205 (14)</td><td class="tabledata" >0.0232 (14)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0007 (9)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0007 (10)</td><td class="tabledata" >0.0047 (11)</td></tr><tr><td class="tabledata" >C5A</td><td class="tabledata" >0.0152 (11)</td><td class="tabledata" >0.0205 (14)</td><td class="tabledata" >0.0150 (12)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0008 (9)</td><td class="tabledata" >0.0007 (9)</td><td class="tabledata" >0.0005 (10)</td></tr><tr><td class="tabledata" >C6A</td><td class="tabledata" >0.0141 (11)</td><td class="tabledata" >0.0192 (13)</td><td class="tabledata" >0.0155 (12)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0020 (9)</td><td class="tabledata" ><sp…
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