/download/c27da460-5f54-4cbd-81ba-321e7c4a6bf5/at2619.html

https://bitbucket.org/petermr/crystaleyetestdata · HTML · 385 lines · 315 code · 38 blank · 32 comment · 0 complexity · b05401d4e0e43e2e736623325879892b MD5 · raw file

Large files are truncated click here to view the full file

    

  1. <!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN"
    2. 

  2.        "http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"><html>
    3. 

  3. <head>
    4. 

  4. <title>(IUCr) Crystallography Journals Online - supplementary material</title>
    5. 

  5. <meta name="copyright" content="&#169; International Union of Crystallography 2008" />
    6. 

  6. <style type="text/css">
    7. 

  7. 	
    8. 

  8.          <!--/* <![CDATA[ */
    9. 

  9. 	  a {color:#000066; text-decoration: none;}
    10. 

  10. 	  a:hover {color:#000000; text-decoration: underline;}
    11. 

  11.           .bluetable {border: 2px solid #99ccff;}
    12. 

  12.           .openurllink {position: absolute; right: 1.0em;} 
    13. 

  13.           h1, h2, h3 {margin-top: 0em; margin-bottom: 0.5em;padding: 0em;}
    14. 

  14.          /* ]]> */-->
    15. 

  15. </style>
    16. 

  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. 

  17. _uacct = "UA-187984-3";
    18. 

  18. urchinTracker();
    19. 

  19. </script><link href="../../../../../styles/publcif.css" rel="stylesheet" type="text/css" /></head>
    20. 

  20. <body bgcolor="#FFFFFF" text="#000000" >
    21. 

  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&amp;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&amp;from=at2619" ><img src="../../../../../graphics/similarpapersborder.gif" alt="similar papers" align="top" border="0" /></a>&nbsp;<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&nbsp;&nbsp;&nbsp;&nbsp;[ <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. 

  22. <h3>2-[2-Chloro-5-(trifluoromethyl)phenyl]hexahydropyrimidine monohydrate</h3><h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&amp;author_name=Fun,%20H.-K.">H.-K.  Fun</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&amp;author_name=Kia,%20R.">R.  Kia</a></h3>
    23. 

  23. <div class="abstract">
    24. 

  24. <a name="abstract"></a>
    25. 

  25. <div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    26. 

  26. </div>
    27. 

  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>&middot;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 (&times; 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 (&times; 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&nbsp;(11)&deg;. 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&nbsp;&Aring;) 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 (&times; 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 (&times; 2) hydrogen-bonding interactions.</p></div>
    28. 

  28. <!-- endabstractdiv -->
    29. 

  29. 

  30. 

  31. 

  32. 

  33. 

  34. <div class="contentslist">
    35. 

  35. <ul>
    36. 

  36. <li class="comment"><a title="Comment" href="#comment">Comment</a></li>
    37. 

  37. <li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li>
    38. 

  38. <li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li>
    39. 

  39. <li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li>
    40. 

  40. <li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li>
    41. 

  41. <li class="figures"><a title="Figures" href="#figures">Figures</a></li>
    42. 

  42. <li><a title="(I)" href="#chemicalname1">2-[2-Chloro-5-(trifluoromethyl)phenyl]hexahydropyrimidine monohydrate </a><ul>
    43. 

  43. <li><a title="Crystal data" href="#crystaldata1">Crystal data</a></li>
    44. 

  44. <li><a title="Data collection" href="#datacollection1">Data collection</a></li>
    45. 

  45. <li><a title="Refinement data" href="#refinementdata1">Refinement data</a></li>
    46. 

  46. <li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li>
    47. 

  47. <li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic coordinates</a></li>
    48. 

  48. <li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li>
    49. 

  49. <li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li>
    50. 

  50. <li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li>
    51. 

  51. <li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li>
    52. 

  52. </ul></li>
    53. 

  53. <li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li>
    54. 

  54. <li class="publreferences"><a title="References" href="#publreferences">References</a></li>
    55. 

  55. </ul>
    56. 

  56. </div>
    57. 

  57. <!-- endcontentslistdiv -->
    58. 

  58. 

  59. <div class="comment">
    60. 

  60. <a name="comment"></a>
    61. 

  61. <div class="heading2">
    62. 

  62. Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    63. 

  63. </div>
    64. 

  64. <!-- endheading2div --><p>Hexahydropyrimidines are prepared classically by condensations of substituted
    65. 

  65. propane-1,3-diamines with aldehydes and ketones. Hexahydropyrimidines are
    66. 

  66. biologically important. <i>N,N'</i>-Bisalkylhexahydro pyrimidines are
    67. 

  67. effective against Ehrlich carcinoma, LK lymphoma, and Staphylococcus aureus.
    68. 

  68. The hexahydropyrimidine skeleton occurs in alkaloids such as verbamethine and
    69. 

  69. verbametrine. <i>N</i>-Substituted hexahydropyrimidines are synthetic
    70. 

  70. intermediates for recently discovered spermidine-nitroimidazole drugs for the
    71. 

  71. treatment of A549 lung carcinoma and structural units in new trypanothione
    72. 

  72. reductase inhibiting ligands for the regulation of oxidative stress in
    73. 

  73. parasitic cells. Benzo-fused hexahydropyrimidines or
    74. 

  74. 1,2,3,4-tetrahydroquinazolines are potential <i>R</i>-adrenergic blockers and
    75. 

  75. possess antiplatelet activity.</p><p>In the title compound (I) (Fig. 1), intramolecular C&#8212;H&#183;&#183;&#183;Cl (<i>x</i> 2),
    76. 

  76. C&#8212;H&#183;&#183;&#183;F, and C&#8212;H&#183;&#183;&#183;N (<i>x</i> 2) hydrogen bonds generate <i>S</i>(5) ring
    77. 

  77. motifs (Bernstein <i>et al.</i>, 1995). The bond lengths and angles are
    78. 

  78. within
    79. 

  79. normal ranges (Allen <i>et al.</i>, 1987). There are two
    80. 

  80. crystallographically
    81. 

  81. independent molecules (A, and B) and two water molecules in the asymmetric
    82. 

  82. unit of the title compound. The dihedral angle between the two benzene rings
    83. 

  83. is 8.17&#160;(11)&#176;. The pyrimidine rings in molecules A and B adopt chair
    84. 

  84. conformation with the puckering parameter (Cremer &amp; Pople, 1975)
    85. 

  85. Q=0.603&#160;(3)&#176;;
    86. 

  86. <span style="font-family:Times">&#952;</span>=1.2&#160;(3)&#176;; <span style="font-family:Times">&#966;</span>=31&#160;(9)&#176; for ring A and Q=0.601&#160;(3)&#176;; <span style="font-family:Times">&#952;</span>=2.5&#160;(3)&#176;; <span style="font-family:Times">&#966;</span>=48&#160;(6)&#176;
    87. 

  87. for ring B. The CF<sub>3</sub> fragment in molecule B, was disordered over four
    88. 

  88. positions with the refined site-occupancies of
    89. 

  89. 0.351&#160;(7)/0.189&#160;(5)/0.289&#160;(9)/0.168&#160;(6) for these four components, respectively.
    90. 

  90. In the crystal structure, molecules are arranged into 1-D extended chains along
    91. 

  91. the <i>c</i>-axis and are further stacked along the <i>a</i>-axis by directed
    92. 

  92. four-membered O&#8212;H&#183;&#183;&#183;O&#8212;H interactions to form 2-D networks which is
    93. 

  93. parralell to <i>ac</i>-plane. The short distances between the centroids of the
    94. 

  94. benzene rings prove an existence of <span style="font-family:Times">&#960;</span>-<span style="font-family:Times">&#960;</span> interactions with distances of
    95. 

  95. 3.8002&#8211;3.8327 &#197;. In addition, the crystal structure is further stabilized
    96. 

  96. by N&#8212;H&#183;&#183;&#183;O, O&#8212;H&#183;&#183;&#183;N (<i>x</i> 4), N&#8212;H&#183;&#183;&#183;Cl, and C&#8212;H&#183;&#183;&#183;O (<i>x</i> 2)
    97. 

  97. hydrogen bonding interactions.</p>
    98. 

  98. </div>
    99. 

  99. <!-- endcommentdiv -->
    100. 

  100. 

  101. 

  102. <div class="relatedliterature">
    103. 

  103. <a name="relatedliterature"></a>
    104. 

  104. <div class="heading2">
    105. 

  105. Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    106. 

  106. </div>
    107. 

  107. <!-- endheading2div --><p>For bond-lengts data, see: Allen <i>et al.</i> (1987). For hydrogen-bond
    108. 

  108. motifs,
    109. 

  109. see: Bernstein <i>et al.</i> (1995). For ring conformations, see:
    110. 

  110. Cremer &amp;
    111. 

  111. Pople (1975). For related literature and properties, see, for example:
    112. 

  112. Riebsomer &amp; Morey (1950); Finch <i>et al.</i> (1952); Drandarov
    113. 

  113. <i>et al.</i>
    114. 

  114. (1999); Siddiqui <i>et al.</i> (1999); Horvath (1997);
    115. 

  115. Katritzky <i>et al.</i>
    116. 

  116. (2002).</p>
    117. 

  117. </div>
    118. 

  118. <!-- endrelatedliteraturediv -->
    119. 

  119. 

  120. 

  121. <div class="experimental">
    122. 

  122. <a name="experimental"></a>
    123. 

  123. <div class="heading2">
    124. 

  124. Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    125. 

  125. </div>
    126. 

  126. <!-- endheading2div --><p>The title compound was synthesized based on the previous method (Finch <i>et
    127. 

  127. al.</i>, 1952). Single crystals suitable for <i>X</i>-ray diffraction
    128. 

  128. were
    129. 

  129. obtained by evaporation of an ethanol solution at room temperature.</p>
    130. 

  130. </div>
    131. 

  131. <!-- endexperimentaldiv -->
    132. 

  132. 

  133. 

  134. <div class="refinement">
    135. 

  135. <a name="refinement"></a>
    136. 

  136. <div class="heading2">
    137. 

  137. Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    138. 

  138. </div>
    139. 

  139. <!-- endheading2div --><p>H atoms bound to the N atoms and water molecules were initially found from the
    140. 

  140. difference Fourier map and refined freely with the parent atoms. The rest of
    141. 

  141. the hydrogen atoms were positioned geometrically and refined as 
    142. 

  142. riding model with
    143. 

  143. <i>U</i><sub>iso</sub>(H) = 1.2 <i>U</i><sub>eq</sub>(C). The disordered fluorine atoms of the
    144. 

  144. CF<sub>3</sub> fragment in molecule B were refined isotropically using C&#8212;F bonds
    145. 

  145. distance restraint of 1.300&#160;(5). Their displacement parameters were restrained
    146. 

  146. using rigid bond model.</p>
    147. 

  147. </div>
    148. 

  148. <!-- endrefinementdiv -->
    149. 

  149. 

  150. 

  151. <div class="computingdetails">
    152. 

  152. <a name="computingdetails"></a>
    153. 

  153. <div class="heading2">
    154. 

  154. Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    155. 

  155. </div>
    156. 

  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. 

  157. </div>
    158. 

  158. <!-- endcomputingdetailsdiv -->
    159. 

  159. 

  160. 

  161. <div class="schemes">
    162. 

  162. <a href="./at2619scheme1.gif"></a>
    163. 

  163. </div>
    164. 

  164. <!-- endschemesdiv -->
    165. 

  165. 

  166. <div class="figures">
    167. 

  167. 

  168. <div class="tablewrap">
    169. 

  169. <a name="figures"></a>
    170. 

  170. <div class="heading2">
    171. 

  171. Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
    172. 

  172. </div>
    173. 

  173. <!-- endheading2div --><table style="table-layout:fixed" width="100%" class="nodecs">
    174. 

  174. <colgroup span="2">
    175. 

  175. <col width="110"></col>
    176. 

  176. <col></col>
    177. 

  177. </colgroup>
    178. 

  178. <tr><td class="nodecs" align="center" width="110">
    179. 

  179. <a href="./at2619fig1.html"><img width="100" src="./at2619fig1thm.gif" alt="[Figure 1]" align="middle"/></a>
    180. 

  180. </td><td class="nodecs" valign="middle" >
    181. 

  181. <font size="2">Fig. 1.  The molecular structure of (I), showing 40% probability displacement
    182. 

  182. ellipsoids. For clarity, only hydrogen atoms of the water molecules and those
    183. 

  183. H atoms involved in intramolecular and intermolecular interactions (shown as
    184. 

  184. dashed lines) were drawn. Open bonds indicate the minor disordered component.</font>
    185. 

  185. </td></tr>
    186. 

  186. <tr><td class="nodecs" align="center" width="110">
    187. 

  187. <a href="./at2619fig2.html"><img width="100" src="./at2619fig2thm.gif" alt="[Figure 2]" align="middle"/></a>
    188. 

  188. </td><td class="nodecs" valign="middle" >
    189. 

  189. <font size="2">Fig. 2.  The crystal packing of the major component of (I), viewed down the
    190. 

  190. <i>a</i>-axis, showing 1-D extended
    191. 

  191. chains along the <i>c</i>-axis and stacking of these chains along the
    192. 

  192. <i>a</i>-axis. Intra and intermolecular interactions are shown as dashed
    193. 

  193. lines.</font>
    194. 

  194. </td></tr>
    195. 

  195. <tr><td class="nodecs" align="center" width="110">
    196. 

  196. <a href="./at2619fig3.html"><img width="100" src="./at2619fig3thm.gif" alt="[Figure 3]" align="middle"/></a>
    197. 

  197. </td><td class="nodecs" valign="middle" >
    198. 

  198. <font size="2">Fig. 3.  The crystal structure of the major component of (I), showing 1-D extended
    199. 

  199. chains along the
    200. 

  200. <i>a</i>-axis.</font>
    201. 

  201. </td></tr>
    202. 

  202. </table>
    203. 

  203. </div>
    204. 

  204. 

  205. </div>
    206. 

  206. <!-- endfiguresdiv -->
    207. 

  207. 

  208. <div class="datablock1">
    209. 

  209. 

  210. 

  211. <div class="heading2">
    212. 

  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. 

  213. </div>
    214. 

  214. <!-- endheading2div -->
    215. 

  215. 

  216. 

  217. <div class="tablewrapcrystaldatalong">
    218. 

  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. 

  219. <colgroup span="2">
    220. 

  220. <col width="50%"></col>
    221. 

  221. <col width="50%"></col>
    222. 

  222. </colgroup>
    223. 

  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>&#183;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>&#8722;</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">&#945;</span> radiation <br /><span style="font-family:Times">&#955;</span> = 0.71073 &#197;</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) &#197;</td><td width="50%" class="tabledata" ><span style="font-family:Times">&#952;</span> = 2.4&#8211;23.0&#186;</td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 18.6119 (5) &#197;</td><td width="50%" class="tabledata" >&#181; = 0.33 mm<span style="font-family:Times"><sup>&#8722;</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 19.0631 (5) &#197;</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">&#946;</span> = 91.010 (2)&#186;</td><td width="50%" class="tabledata" >Block, colourless</td></tr><tr><td width="50%" class="tabledata" ><i>V</i> = 2509.65 (12)  &#197;<sup>3</sup></td><td width="50%" class="tabledata" >0.24 &#215; 0.05 &#215; 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. 

  224. </div>
    225. 

  225. <!-- endtablewrapcrystaldatalongdiv -->
    226. 

  226. 

  227. <div class="tablewrapdatacollectionlong">
    228. 

  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. 

  229. <colgroup span="2">
    230. 

  230. <col width="50%"></col>
    231. 

  231. <col width="50%"></col>
    232. 

  232. </colgroup>
    233. 

  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">&#963;</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">&#952;</span><sub>max</sub> = 30.1&#186;</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">&#966;</span> and <span style="font-family:Times">&#969;</span> scans</td><td width="50%" class="tabledata" ><span style="font-family:Times">&#952;</span><sub>min</sub> = 2.1&#186;</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">&#8722;</span>9&#8594;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">&#8722;</span>26&#8594;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">&#8722;</span>16&#8594;26</td></tr></table><!-- endtabledatatable -->
    234. 

  234. </div>
    235. 

  235. <!-- endtablewrapdatacollectionlongdiv -->
    236. 

  236. 

  237. <div class="tablewraprefinementdatalong">
    238. 

  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. 

  239. <colgroup span="2">
    240. 

  240. <col width="50%"></col>
    241. 

  241. <col width="50%"></col>
    242. 

  242. </colgroup>
    243. 

  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">&#963;</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" >&#160;   <i>w</i> = 1/[<span style="font-family:Times">&#963;</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" >(&#916;/<span style="font-family:Times">&#963;</span>)<sub>max</sub> &lt; 0.001</td></tr><tr><td width="50%" class="tabledata" >7308 reflections</td><td width="50%" class="tabledata" >&#916;<span style="font-family:Times">&#961;</span><sub>max</sub> = 0.61 e &#197;<span style="font-family:Times"><sup>&#8722;</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >379 parameters</td><td width="50%" class="tabledata" >&#916;<span style="font-family:Times">&#961;</span><sub>min</sub> = <span style="font-family:Times">&#8722;</span>0.60 e &#197;<span style="font-family:Times"><sup>&#8722;</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. 

  244. </div>
    245. 

  245. <!-- endtablewraprefinementdatalongdiv -->
    246. 

  246. 

  247. <div class="tablewrapcrystaldatashort">
    248. 

  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. 

  249. <colgroup span="2">
    250. 

  250. <col width="50%"></col>
    251. 

  251. <col width="50%"></col>
    252. 

  252. </colgroup>
    253. 

  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>&#183;H<sub>2</sub>O<sub>1</sub></td><td width="50%" class="tabledata" ><i>V</i> = 2509.65 (12)  &#197;<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">&#945;</span></td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 7.0745 (2) &#197;</td><td width="50%" class="tabledata" >&#181; = 0.33 mm<span style="font-family:Times"><sup>&#8722;</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 18.6119 (5) &#197;</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) &#197;</td><td width="50%" class="tabledata" >0.24 &#215; 0.05 &#215; 0.02 mm</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">&#946;</span> = 91.010 (2)&#186;</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable -->
    254. 

  254. </div>
    255. 

  255. <!-- endtablewrapcrystaldatashortdiv -->
    256. 

  256. 

  257. <div class="tablewrapdatacollectionshort">
    258. 

  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. 

  259. <colgroup span="2">
    260. 

  260. <col width="50%"></col>
    261. 

  261. <col width="50%"></col>
    262. 

  262. </colgroup>
    263. 

  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">&#963;</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. 

  264. </div>
    265. 

  265. <!-- endtablewrapdatacollectionshortdiv -->
    266. 

  266. 

  267. <div class="tablewraprefinementdatashort">
    268. 

  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. 

  269. <colgroup span="2">
    270. 

  270. <col width="50%"></col>
    271. 

  271. <col width="50%"></col>
    272. 

  272. </colgroup>
    273. 

  273. <tr><td width="50%" class="tabledata" ><i>R</i>[<i>F</i><sup>2</sup> > 2<span style="font-family:Times">&#963;</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" >&#916;<span style="font-family:Times">&#961;</span><sub>max</sub> = 0.61 e &#197;<span style="font-family:Times"><sup>&#8722;</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >7308 reflections</td><td width="50%" class="tabledata" >&#916;<span style="font-family:Times">&#961;</span><sub>min</sub> = <span style="font-family:Times">&#8722;</span>0.60 e &#197;<span style="font-family:Times"><sup>&#8722;</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. 

  274. </div>
    275. 

  275. <!-- endtablewraprefinementdatashortdiv -->
    276. 

  276. <div class="specialdetails">
    277. 

  277. 

  278. <div class="tablewrap">
    279. 

  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. 

  280. <table style="table-layout:fixed" width="100%" class="tabledata">
    281. 

  281. <tr><td class="tabledata"><p><b>Experimental</b>. The low-temperature data was collected with the Oxford Cyrosystem Cobra
    282. 

  282. low-temperature attachment.</p></td></tr>
    283. 

  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)
    284. 

  284. are estimated using the full covariance matrix. The cell e.s.d.'s are taken
    285. 

  285. into account individually in the estimation of e.s.d.'s in distances, angles
    286. 

  286. and torsion angles; correlations between e.s.d.'s in cell parameters are only
    287. 

  287. used when they are defined by crystal symmetry. An approximate (isotropic)
    288. 

  288. treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
    289. 

  289. planes.</p></td></tr>
    290. 

  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. 

  291. <i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, conventional
    292. 

  292. <i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
    293. 

  293. negative <i>F</i><sup>2</sup>. The threshold expression of <i>F</i><sup>2</sup> >
    294. 

  294. <span style="font-family:Times">&#963;</span>(<i>F</i><sup>2</sup>) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
    295. 

  295. and is not relevant to the choice of reflections for refinement.
    296. 

  296. <i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically about twice as large
    297. 

  297. as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
    298. 

  298. even larger.</p></td></tr></table>
    299. 

  299. </div>
    300. 

  300. 

  301. </div>
    302. 

  302. <!-- endspecialdetailsdiv -->
    303. 

  303. 

  304. <div class="tablewrapcoords">
    305. 

  305. <a name="fractionalatomiccoordinates1"></a> <span class="heading3">Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (&#197;<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. (&lt;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">&#8722;</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">&#8722;</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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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&#160;(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">&#8722;</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. 

  306. </div>
    307. 

  307. <!-- endtablewrapcoordsdiv -->
    308. 

  308. <div class="tablewrapadps">
    309. 

  309. <a name="atomicdisplacement1"></a> <span class="heading3">Atomic displacement parameters (&#197;<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">&#8722;</span>0.0001 (2)</td><td class="tabledata" ><span style="font-family:Times">&#8722;</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">&#8722;</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">&#8722;</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">&#8722;</span>0.0107 (7)</td><td class="tabledata" >0.0116 (8)</td><td class="tabledata" ><span style="font-family:Times">&#8722;</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">&#8722;</span>0.0012 (10)</td><td class="tabledata" ><span style="font-family:Times">&#8722;</span>0.0013 (9)</td><td class="tabledata" ><span style="font-family:Times">&#8722;</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">&#8722;</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">&#8722;</span>0.0020 (10)</td><td class="tabledata" ><span style="font-family:Times">&#8722;</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">&#8722;</span>0.0007 (9)</td><td class="tabledata" ><span style="font-family:Times">&#8722;</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">&#8722;</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">&#8722;</span>0.0020 (9)</td><td class="tabledata" ><sp…
    310.