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1<?xml version="1.0" encoding="UTF-8"?> 2<html cmlx:fileId="C:\Users\pm286\workspace\crystaleyeTestData\html\3\8\d\38d7f31c-b43e-44b7-a047-dbb5e465d903\suppText.html" xmlns:cmlx="http://www.xml-cml.org/schema/cmlx"> 3<head> 4<meta name="generator" content="HTML Tidy, see www.w3.org"/> 5<title>(IUCr) Crystallography Journals Online - supplementary 6material</title> 7<meta name="copyright" content="� International Union of Crystallography 2010"/> 8<style type="text/css"> 9 10 <!--/* <![CDATA[ */ 11 a {color:#000066; text-decoration: none;} 12 a:hover {color:#000000; text-decoration: underline;} 13 .bluetable {border: 2px solid #99ccff;} 14 .openurllink {position: absolute; right: 1.0em;} 15 h1, h2, h3 {margin-top: 0em; margin-bottom: 0.5em;padding: 0em;} 16 /* ]]> */--> 17</style> 18 19<script language="JavaScript" src="http://journals.iucr.org/javascript/scripts.js" type="text/javascript"> 20</script> 21 22<script type="text/javascript"> 23var gaJsHost = (("https:" == 24document.location.protocol) ? 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E<b>64</b>, 47o1941-o1942����[ <a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536808029000">doi:10.1107/S1600536808029000</a> 48]</p> 49</div> 50 51<h3><span class="it"><i>N</i></span>,<span class="it"><i>N</i></span>'-Bis(4-bromo-2-fluorobenzylidene)ethane-1,2-diamine</h3> 52 53<h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Fun,%20H.-K."> 54H.-K. Fun</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Kia,%20R."> 55R. Kia</a></h3> 56 57<div class="abstract"><a id="abstract" name="abstract"/> 58 59<div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 60</div> 61 62<!-- endheading2div --> 63<p>The molecule of the title Schiff base compound, C<span class="inf"><sub>16</sub></span>H<span class="inf"><sub>12</sub></span>Br<span class="inf"><sub>2</sub></span>F<span class="inf"><sub>2</sub></span>N<span class="inf"><sub>2</sub></span>, lies across a crystallographic 64inversion centre and adopts an <span class="it"><i>E</i></span> 65configuration with respect to the azomethine C=N bonds. The imino 66groups are coplanar with the aromatic rings. Within the molecule, 67the planar units are parallel, but extend in opposite directions 68from the dimethylene bridge. An interesting feature of the crystal 69structure is the short intermolecular Br<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif"/>F interactions 70[3.2347�(16)��, which is shorter than the sum of the 71van der Waals radii of these atoms]. These interactions link 72neighbouring molecules along the <span class="it"><i>c</i></span> 73axis. The crystal structure is further stabilized by intermolecular 74C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif"/>N hydrogen bonds.</p> 75</div> 76 77<!-- endabstractdiv --> 78<div class="contentslist"> 79<ul> 80<li class="comment"><a title="Comment" href="#comment">Comment</a></li> 81 82<li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li> 83 84<li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li> 85 86<li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li> 87 88<li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li> 89 90<li class="figures"><a title="Figures" href="#figures">Figures</a></li> 91 92<li><a title="(I)" href="#chemicalname1">N,N'-Bis(4-bromo-2-fluorobenzylidene)ethane-1,2-diamine</a> 93 94 95<ul> 96<li><a title="Crystal data" href="#crystaldata1">Crystal 97data</a></li> 98 99<li><a title="Data collection" href="#datacollection1">Data 100collection</a></li> 101 102<li><a title="Refinement data" href="#refinementdata1">Refinement 103data</a></li> 104 105<li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li> 106 107<li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic 108coordinates</a></li> 109 110<li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li> 111 112<li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li> 113 114<li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 115 116<li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 117</ul> 118</li> 119 120<li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li> 121 122<li class="publreferences"><a title="References" href="#publreferences">References</a></li> 123</ul> 124</div> 125 126<!-- endcontentslistdiv --> 127<div class="comment"><a id="comment" name="comment"/> 128 129<div class="heading2">Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 130</div> 131 132<!-- endheading2div --> 133<p>Schiff bases are one of most prevalent mixed-donor ligands in 134the field of coordination chemistry. There has been growing 135interest in Schiff base ligands, mainly because of their wide 136application in the field of biochemistry, synthesis, and catalysis 137(Pal <i>et al.</i>, 2005; Hou <i>et al.</i>, 2001; Ren <i>et 138al.</i>, 2002). Many Schiff base complexes have been structurally 139characterized, but only a relatively small number of free Schiff 140bases have been characterized (Calligaris & Randaccio, 1987). 141As an extension of our work (Fun & Kia 2008<i>a,b,c</i>; Fun 142<i>et al.</i>, 2008) on the structural characterization of Schiff 143base ligands, and the halogen-halogen interactions in the 144halogen-subtituated Schiff bases, the title compound (I), is 145reported here.</p> 146 147<p>The molecule of the title compound, (I), (Fig. 1), lies across a 148crystallographic inversion centre and adopts an <i>E</i> 149configuration with respect to the azomethine C<span style="font-family:Times">?</span>N bond. The bond lengths 150(Allen <i>et al.</i>, 1987) and angles are within normal ranges and 151are comparable with the related structures (Fun & Kia 1522008<i>a,b,c</i>; Fun <i>et al.</i>, 2008). The two planar units 153are parallel but extend in opposite directions from the dimethylene 154bridge. The interesting feature of the crystal structure is the 155short intermolecular Br���F interactions [symmetry 156code: 1 - <i>x</i>, -1/2 + <i>y</i>, 1/2 - <i>z</i>] with the 157distance of 3.2347�(16) �, which is shorter than the sum 158of the van der Waals radii of these atoms. The directionality of 159these interactions, C-<i>X</i>���<i>X</i>-C 160(<i>X</i> = halogens), has been attributed to anisotropic van der 161Waals radii for terminally bound halogens or ascribed to 162donor-acceptor interactions involving a lone pair donor orbital on 163one halogen and a C-<i>X</i> <span style="font-family:Times">?</span><sup>*</sup> acceptor 164orbital on the other (Ramasubbu <i>et al.</i>, 1986; Brammer <i>et 165al.</i>, 2003). These interactions link neighbouring molecules 166along the <i>c</i>-axis (Fig. 2). The crystal structure is further 167stabilized by intermolecular C-H���N hydrogen bonds 168(Table 1).</p> 169</div> 170 171<!-- endcommentdiv --> 172<div class="relatedliterature"><a id="relatedliterature" name="relatedliterature"/> 173 174<div class="heading2">Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 175</div> 176 177<!-- endheading2div --> 178<p>For bond-length data, see: Allen <i>et al.</i> (1987). For 179halogen-halogen interactions, see: Ramasubbu <i>et al.</i> (1986); 180Brammer <i>et al.</i> (2003). For related structures, see, for 181example: Fun & Kia (2008<i>a</i>,<i>b</i>,<i>c</i>): Fun <i>et 182al.</i> (2008). For Schiff base complexes and their applications, 183see, for example: Pal <i>et al.</i> (2005); Calligaris & 184Randaccio, (1987); Hou <i>et al.</i> (2001); Ren <i>et al.</i> 185(2002).</p> 186</div> 187 188<!-- endrelatedliteraturediv --> 189<div class="experimental"><a id="experimental" name="experimental"/> 190 191<div class="heading2">Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 192</div> 193 194<!-- endheading2div --> 195<p>The synthetic method has been described earlier (Fun & Kia 1962008<i>a</i>). Single crystals suitable for <i>X</i>-ray 197diffraction were obtained by evaporation of an ethanol solution at 198room temperature.</p> 199</div> 200 201<!-- endexperimentaldiv --> 202<div class="refinement"><a id="refinement" name="refinement"/> 203 204<div class="heading2">Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 205</div> 206 207<!-- endheading2div --> 208<p>All of the hydrogen atoms were positioned geometrically with C-H 209= 0.93 or 0.97 � and refined in riding model with 210<i>U</i><sub>iso</sub> (H) = 1.2 <i>U</i><sub>eq</sub> (C). The 211highest peak is located 1.73 � from Br1 and the deepest hole 212is located 0.7 � from Br1.</p> 213</div> 214 215<!-- endrefinementdiv --> 216<div class="computingdetails"><a id="computingdetails" name="computingdetails"/> 217 218<div class="heading2">Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 219</div> 220 221<!-- endheading2div --> 222<p>Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 223(Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) 224used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used 225to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: 226SHELXTL (Sheldrick, 2008); software used to prepare material for 227publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).</p> 228</div> 229 230<!-- endcomputingdetailsdiv --> 231<div class="schemes"><a href="./at2629scheme1.gif"/></div> 232 233<!-- endschemesdiv --> 234<div class="figures"><a id="figures" name="figures"/> 235 236<div class="heading2">Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 237</div> 238 239<!-- endheading2div --> 240<table style="table-layout:fixed" width="100%" class="nodecs"> 241<colgroup span="2"> 242<col width="110"/> 243<col/></colgroup> 244 245<tr> 246<td class="nodecs" align="center" width="110"><a href="./at2629fig1.html"><img width="100" src="./at2629fig1thm.gif" alt="[Figure 1]" align="middle"/></a> </td> 247<td class="nodecs" valign="middle">Fig. 1. The molecular structure 248of (I) with atom labels and 50% probability ellipsoids for non-H 249atoms [symmetry code for A: -<i>x</i>, -<i>y</i>, -<i>z</i>. </td> 250</tr> 251 252<tr> 253<td class="nodecs" align="center" width="110"><a href="./at2629fig2.html"><img width="100" src="./at2629fig2thm.gif" alt="[Figure 2]" align="middle"/></a> </td> 254<td class="nodecs" valign="middle">Fig. 2. The crystal packing of 255(I), viewed down the <i>a</i>-axis, shows linking of molecules by 256Br���F contacts along the <i>c</i>-axis and the 257stacking of these molecules down the <i>a</i>-axis. Intermolecular 258interactions are shown as dashed lines. </td> 259</tr> 260</table> 261</div> 262 263<!-- endfiguresdiv --> 264<div class="datablock1"> 265<div class="heading2"><a id="chemicalname1" name="chemicalname1"/>N,N'-Bis(4-bromo-2-fluorobenzylidene)ethane-1,2-diamine 266<span class="toplink"><a class="buttons" href="#top">top</a></span> 267<!-- endtoplinkspan --> 268</div> 269 270<!-- endheading2div --> 271<div class="tablewrapcrystaldatalong"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span> 272<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 273<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 274<colgroup span="2"> 275<col width="50%"/> 276<col width="50%"/></colgroup> 277 278<tr> 279<td width="50%" class="tabledata"> 280C<sub>16</sub>H<sub>12</sub>Br<sub>2</sub>F<sub>2</sub>N<sub>2</sub></td> 281<td width="50%" class="tabledata"><i>F</i>(000) = 420</td> 282</tr> 283 284<tr> 285<td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> = 286430.10</td> 287<td width="50%" class="tabledata"><i>D</i><sub>x</sub> = 1.868 Mg 288m<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 289</tr> 290 291<tr> 292<td width="50%" class="tabledata">Monoclinic, 293<i>P</i>2<sub>1</sub>/<i>c</i></td> 294<td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span> radiation, <span style="font-family:Times">?</span> = 0.71073 �</td> 295</tr> 296 297<tr> 298<td width="50%" class="tabledata">Hall symbol: -P 2ybc</td> 299<td width="50%" class="tabledata">Cell parameters from 5643 300reflections</td> 301</tr> 302 303<tr> 304<td width="50%" class="tabledata"><i>a</i> = 4.1981 (1) �</td> 305<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 3.2-30.0�</td> 306</tr> 307 308<tr> 309<td width="50%" class="tabledata"><i>b</i> = 14.6190 (3) 310�</td> 311<td width="50%" class="tabledata">� = 5.32 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td> 312</tr> 313 314<tr> 315<td width="50%" class="tabledata"><i>c</i> = 12.8861 (3) 316�</td> 317<td width="50%" class="tabledata"><i>T</i> = 100 K</td> 318</tr> 319 320<tr> 321<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 104.751 (2)�</td> 322<td width="50%" class="tabledata">Needle, colourless</td> 323</tr> 324 325<tr> 326<td width="50%" class="tabledata"><i>V</i> = 764.78 (3) 327�<sup>3</sup></td> 328<td width="50%" class="tabledata">0.51 � 0.07 � 0.05 329mm</td> 330</tr> 331 332<tr> 333<td width="50%" class="tabledata"><i>Z</i> = 2</td> 334<td width="50%" class="tabledata"/> 335</tr> 336</table> 337 338<!-- endtabledatatable --> 339</div> 340 341<!-- endtablewrapcrystaldatalongdiv --> 342<div class="tablewrapdatacollectionlong"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data 343collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 344<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 345<colgroup span="2"> 346<col width="50%"/> 347<col width="50%"/></colgroup> 348 349<tr> 350<td width="50%" class="tabledata">Bruker SMART APEXII CCD 351area-detector<br/> 352diffractometer</td> 353<td width="50%" class="tabledata">2631 independent reflections</td> 354</tr> 355 356<tr> 357<td width="50%" class="tabledata">Radiation source: fine-focus 358sealed tube</td> 359<td width="50%" class="tabledata">1907 reflections with <i>I</i> 360> 2<span style="font-family:Times">?</span>(<i>I</i>)</td> 361</tr> 362 363<tr> 364<td width="50%" class="tabledata">graphite</td> 365<td width="50%" class="tabledata"><i>R</i><sub>int</sub> = 3660.050</td> 367</tr> 368 369<tr> 370<td width="50%" class="tabledata"><span style="font-family:Times">?</span> and <span style="font-family:Times">?</span> scans</td> 371<td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>max</sub> = 32.0�, 372<span style="font-family:Times">?</span><sub>min</sub> = 3732.2�</td> 374</tr> 375 376<tr> 377<td width="50%" class="tabledata">Absorption correction: 378multi-scan<br/> 379(SADABS; Bruker, 2005)</td> 380<td width="50%" class="tabledata"><i>h</i> = <span style="font-family:Times">?</span>6<span style="font-family:Times">?</span>6</td> 381</tr> 382 383<tr> 384<td width="50%" class="tabledata"><i>T</i><sub>min</sub> = 0.172, 385<i>T</i><sub>max</sub> = 0.770</td> 386<td width="50%" class="tabledata"><i>k</i> = <span style="font-family:Times">?</span>21<span style="font-family:Times">?</span>21</td> 387</tr> 388 389<tr> 390<td width="50%" class="tabledata">19361 measured reflections</td> 391<td width="50%" class="tabledata"><i>l</i> = <span style="font-family:Times">?</span>19<span style="font-family:Times">?</span>18</td> 392</tr> 393</table> 394 395<!-- endtabledatatable --> 396</div> 397 398<!-- endtablewrapdatacollectionlongdiv --> 399<div class="tablewraprefinementdatalong"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span> 400<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 401<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 402<colgroup span="2"> 403<col width="50%"/> 404<col width="50%"/></colgroup> 405 406<tr> 407<td width="50%" class="tabledata">Refinement on 408<i>F</i><sup>2</sup></td> 409<td width="50%" class="tabledata">Primary atom site location: 410structure-invariant direct methods</td> 411</tr> 412 413<tr> 414<td width="50%" class="tabledata">Least-squares matrix: full</td> 415<td width="50%" class="tabledata">Secondary atom site location: 416difference Fourier map</td> 417</tr> 418 419<tr> 420<td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup> 421> 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] = 4220.040</td> 423<td width="50%" class="tabledata">Hydrogen site location: inferred 424from neighbouring sites</td> 425</tr> 426 427<tr> 428<td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) = 4290.100</td> 430<td width="50%" class="tabledata">H-atom parameters 431constrained</td> 432</tr> 433 434<tr> 435<td width="50%" class="tabledata"><i>S</i> = 1.05</td> 436<td width="50%" class="tabledata"><i>w</i> = 1/[<span style="font-family:Times">?</span><sup>2</sup>(<i>F</i><sub>o</sub><sup> 4372</sup>) + (0.0539<i>P</i>)<sup>2</sup>]<br/> 438where <i>P</i> = (<i>F</i><sub>o</sub><sup>2</sup> + 4392<i>F</i><sub>c</sub><sup>2</sup>)/3</td> 440</tr> 441 442<tr> 443<td width="50%" class="tabledata">2631 reflections</td> 444<td width="50%" class="tabledata">(?/<span style="font-family:Times">?</span>)<sub>max</sub> < 4450.001</td> 446</tr> 447 448<tr> 449<td width="50%" class="tabledata">100 parameters</td> 450<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 1.40 e 451�<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 452</tr> 453 454<tr> 455<td width="50%" class="tabledata">0 restraints</td> 456<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>0.86 e �<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 457</tr> 458</table> 459 460<!-- endtabledatatable --> 461</div> 462 463<!-- endtablewraprefinementdatalongdiv --> 464<div class="tablewrapcrystaldatashort"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span> 465<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 466<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 467<colgroup span="2"> 468<col width="50%"/> 469<col width="50%"/></colgroup> 470 471<tr> 472<td width="50%" class="tabledata"> 473C<sub>16</sub>H<sub>12</sub>Br<sub>2</sub>F<sub>2</sub>N<sub>2</sub></td> 474<td width="50%" class="tabledata"><i>V</i> = 764.78 (3) 475�<sup>3</sup></td> 476</tr> 477 478<tr> 479<td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> = 480430.10</td> 481<td width="50%" class="tabledata"><i>Z</i> = 2</td> 482</tr> 483 484<tr> 485<td width="50%" class="tabledata">Monoclinic, 486<i>P</i>2<sub>1</sub>/<i>c</i></td> 487<td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span> radiation</td> 488</tr> 489 490<tr> 491<td width="50%" class="tabledata"><i>a</i> = 4.1981 (1) �</td> 492<td width="50%" class="tabledata">� = 5.32 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td> 493</tr> 494 495<tr> 496<td width="50%" class="tabledata"><i>b</i> = 14.6190 (3) 497�</td> 498<td width="50%" class="tabledata"><i>T</i> = 100 K</td> 499</tr> 500 501<tr> 502<td width="50%" class="tabledata"><i>c</i> = 12.8861 (3) 503�</td> 504<td width="50%" class="tabledata">0.51 � 0.07 � 0.05 505mm</td> 506</tr> 507 508<tr> 509<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 104.751 (2)�</td> 510<td width="50%" class="tabledata"/> 511</tr> 512</table> 513 514<!-- endtabledatatable --> 515</div> 516 517<!-- endtablewrapcrystaldatashortdiv --> 518<div class="tablewrapdatacollectionshort"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data 519collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 520<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 521<colgroup span="2"> 522<col width="50%"/> 523<col width="50%"/></colgroup> 524 525<tr> 526<td width="50%" class="tabledata">Bruker SMART APEXII CCD 527area-detector<br/> 528diffractometer</td> 529<td width="50%" class="tabledata">2631 independent reflections</td> 530</tr> 531 532<tr> 533<td width="50%" class="tabledata">Absorption correction: 534multi-scan<br/> 535(SADABS; Bruker, 2005)</td> 536<td width="50%" class="tabledata">1907 reflections with <i>I</i> 537> 2<span style="font-family:Times">?</span>(<i>I</i>)</td> 538</tr> 539 540<tr> 541<td width="50%" class="tabledata"><i>T</i><sub>min</sub> = 0.172, 542<i>T</i><sub>max</sub> = 0.770</td> 543<td width="50%" class="tabledata"><i>R</i><sub>int</sub> = 5440.050</td> 545</tr> 546 547<tr> 548<td width="50%" class="tabledata">19361 measured reflections</td> 549<td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>max</sub> = 55032.0�</td> 551</tr> 552</table> 553 554<!-- endtabledatatable --> 555</div> 556 557<!-- endtablewrapdatacollectionshortdiv --> 558<div class="tablewraprefinementdatashort"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span> 559<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 560<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 561<colgroup span="2"> 562<col width="50%"/> 563<col width="50%"/></colgroup> 564 565<tr> 566<td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup> 567> 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] = 5680.040</td> 569<td width="50%" class="tabledata">H-atom parameters 570constrained</td> 571</tr> 572 573<tr> 574<td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) = 5750.100</td> 576<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 1.40 e 577�<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 578</tr> 579 580<tr> 581<td width="50%" class="tabledata"><i>S</i> = 1.05</td> 582<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>0.86 e �<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 583</tr> 584 585<tr> 586<td width="50%" class="tabledata">2631 reflections</td> 587<td width="50%" class="tabledata">Absolute structure: ?</td> 588</tr> 589 590<tr> 591<td width="50%" class="tabledata">100 parameters</td> 592<td width="50%" class="tabledata">Flack parameter: ?</td> 593</tr> 594 595<tr> 596<td width="50%" class="tabledata">0 restraints</td> 597<td width="50%" class="tabledata">Rogers parameter: ?</td> 598</tr> 599</table> 600 601<!-- endtabledatatable --> 602</div> 603 604<!-- endtablewraprefinementdatashortdiv --> 605<div class="specialdetails"><a id="specialdetails1" name="specialdetails1"/><span class="heading3">Special 606details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 607<table style="table-layout:fixed" width="100%" class="tabledata"> 608<tr> 609<td class="tabledata"> 610<p><b>Geometry</b>. All e.s.d.'s (except the e.s.d. in the 611dihedral angle between two l.s. planes) are estimated using the 612full covariance matrix. The cell e.s.d.'s are taken into 613account individually in the estimation of e.s.d.'s in 614distances, angles and torsion angles; correlations between 615e.s.d.'s in cell parameters are only used when they are defined 616by crystal symmetry. An approximate (isotropic) treatment of cell 617e.s.d.'s is used for estimating e.s.d.'s involving l.s. 618planes.</p> 619</td> 620</tr> 621 622<tr> 623<td class="tabledata"> 624<p><b>Refinement</b>. Refinement of <i>F</i><sup>2</sup> against 625ALL reflections. The weighted <i>R</i>-factor <i>wR</i> and 626goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, 627conventional <i>R</i>-factors <i>R</i> are based on <i>F</i>, with 628<i>F</i> set to zero for negative <i>F</i><sup>2</sup>. The 629threshold expression of <i>F</i><sup>2</sup> > <span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>) is 630used only for calculating <i>R</i>-factors(gt) <i>etc</i>. and is 631not relevant to the choice of reflections for refinement. 632<i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically 633about twice as large as those based on <i>F</i>, and <i>R</i>- 634factors based on ALL data will be even larger.</p> 635</td> 636</tr> 637</table> 638</div> 639 640<!-- endspecialdetailsdiv --> 641<div class="tablewrapcoords"><a id="fractionalatomiccoordinates1" name="fractionalatomiccoordinates1"/> <span class="heading3">Fractional atomic coordinates and isotropic or 642equivalent isotropic displacement parameters 643(�<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span> 644<!-- endtoplinkspan --> 645<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 646<tr> 647<td class="tabledata"/> 648<td class="tabledata"><i>x</i></td> 649<td class="tabledata"><i>y</i></td> 650<td class="tabledata"><i>z</i></td> 651<td class="tabledata"> 652<i>U</i><sub>iso</sub>*/<i>U</i><sub>eq</sub></td> 653<td class="tabledata"/> 654</tr> 655 656<tr> 657<td class="tabledata">Br1</td> 658<td class="tabledata"><span style="font-family:Times">?</span>0.74079 (7)</td> 659<td class="tabledata"><span style="font-family:Times">?</span>0.51485 (2)</td> 660<td class="tabledata">0.18481 (2)</td> 661<td class="tabledata">0.02329 (11)</td> 662<td class="tabledata"/> 663</tr> 664 665<tr> 666<td class="tabledata">F1</td> 667<td class="tabledata"><span style="font-family:Times">?</span>0.0347 (4)</td> 668<td class="tabledata"><span style="font-family:Times">?</span>0.22639 (11)</td> 669<td class="tabledata">0.31348 (12)</td> 670<td class="tabledata">0.0267 (4)</td> 671<td class="tabledata"/> 672</tr> 673 674<tr> 675<td class="tabledata">N1</td> 676<td class="tabledata"><span style="font-family:Times">?</span>0.0960 (6)</td> 677<td class="tabledata"><span style="font-family:Times">?</span>0.12204 (15)</td> 678<td class="tabledata">0.01873 (19)</td> 679<td class="tabledata">0.0192 (5)</td> 680<td class="tabledata"/> 681</tr> 682 683<tr> 684<td class="tabledata">C1</td> 685<td class="tabledata"><span style="font-family:Times">?</span>0.2112 (7)</td> 686<td class="tabledata"><span style="font-family:Times">?</span>0.27577 (19)</td> 687<td class="tabledata">0.2280 (2)</td> 688<td class="tabledata">0.0199 (5)</td> 689<td class="tabledata"/> 690</tr> 691 692<tr> 693<td class="tabledata">C2</td> 694<td class="tabledata"><span style="font-family:Times">?</span>0.3675 (7)</td> 695<td class="tabledata"><span style="font-family:Times">?</span>0.35336 (19)</td> 696<td class="tabledata">0.2493 (2)</td> 697<td class="tabledata">0.0206 (6)</td> 698<td class="tabledata"/> 699</tr> 700 701<tr> 702<td class="tabledata">H2A</td> 703<td class="tabledata"><span style="font-family:Times">?</span>0.3576</td> 704<td class="tabledata"><span style="font-family:Times">?</span>0.3716</td> 705<td class="tabledata">0.3192</td> 706<td class="tabledata">0.025*</td> 707<td class="tabledata"/> 708</tr> 709 710<tr> 711<td class="tabledata">C3</td> 712<td class="tabledata"><span style="font-family:Times">?</span>0.5404 (7)</td> 713<td class="tabledata"><span style="font-family:Times">?</span>0.40314 (18)</td> 714<td class="tabledata">0.1619 (2)</td> 715<td class="tabledata">0.0181 (5)</td> 716<td class="tabledata"/> 717</tr> 718 719<tr> 720<td class="tabledata">C4</td> 721<td class="tabledata"><span style="font-family:Times">?</span>0.5632 (7)</td> 722<td class="tabledata"><span style="font-family:Times">?</span>0.37558 (19)</td> 723<td class="tabledata">0.0569 (2)</td> 724<td class="tabledata">0.0215 (6)</td> 725<td class="tabledata"/> 726</tr> 727 728<tr> 729<td class="tabledata">H4A</td> 730<td class="tabledata"><span style="font-family:Times">?</span>0.6819</td> 731<td class="tabledata"><span style="font-family:Times">?</span>0.4099</td> 732<td class="tabledata"><span style="font-family:Times">?</span>0.0009</td> 733<td class="tabledata">0.026*</td> 734<td class="tabledata"/> 735</tr> 736 737<tr> 738<td class="tabledata">C5</td> 739<td class="tabledata"><span style="font-family:Times">?</span>0.4047 (7)</td> 740<td class="tabledata"><span style="font-family:Times">?</span>0.29567 (19)</td> 741<td class="tabledata">0.0405 (2)</td> 742<td class="tabledata">0.0208 (6)</td> 743<td class="tabledata"/> 744</tr> 745 746<tr> 747<td class="tabledata">H5A</td> 748<td class="tabledata"><span style="font-family:Times">?</span>0.4212</td> 749<td class="tabledata"><span style="font-family:Times">?</span>0.2761</td> 750<td class="tabledata"><span style="font-family:Times">?</span>0.0293</td> 751<td class="tabledata">0.025*</td> 752<td class="tabledata"/> 753</tr> 754 755<tr> 756<td class="tabledata">C6</td> 757<td class="tabledata"><span style="font-family:Times">?</span>0.2210 (6)</td> 758<td class="tabledata"><span style="font-family:Times">?</span>0.24370 (18)</td> 759<td class="tabledata">0.1260 (2)</td> 760<td class="tabledata">0.0174 (5)</td> 761<td class="tabledata"/> 762</tr> 763 764<tr> 765<td class="tabledata">C7</td> 766<td class="tabledata"><span style="font-family:Times">?</span>0.0381 (6)</td> 767<td class="tabledata"><span style="font-family:Times">?</span>0.16150 (18)</td> 768<td class="tabledata">0.1090 (2)</td> 769<td class="tabledata">0.0182 (5)</td> 770<td class="tabledata"/> 771</tr> 772 773<tr> 774<td class="tabledata">H7A</td> 775<td class="tabledata">0.1239</td> 776<td class="tabledata"><span style="font-family:Times">?</span>0.1380</td> 777<td class="tabledata">0.1659</td> 778<td class="tabledata">0.022*</td> 779<td class="tabledata"/> 780</tr> 781 782<tr> 783<td class="tabledata">C8</td> 784<td class="tabledata">0.1076 (7)</td> 785<td class="tabledata"><span style="font-family:Times">?</span>0.04254 (19)</td> 786<td class="tabledata">0.0114 (2)</td> 787<td class="tabledata">0.0208 (5)</td> 788<td class="tabledata"/> 789</tr> 790 791<tr> 792<td class="tabledata">H8A</td> 793<td class="tabledata">0.2171</td> 794<td class="tabledata"><span style="font-family:Times">?</span>0.0516</td> 795<td class="tabledata"><span style="font-family:Times">?</span>0.0456</td> 796<td class="tabledata">0.025*</td> 797<td class="tabledata"/> 798</tr> 799 800<tr> 801<td class="tabledata">H8B</td> 802<td class="tabledata">0.2750</td> 803<td class="tabledata"><span style="font-family:Times">?</span>0.0349</td> 804<td class="tabledata">0.0783</td> 805<td class="tabledata">0.025*</td> 806<td class="tabledata"/> 807</tr> 808</table> 809</div> 810 811<!-- endtablewrapcoordsdiv --> 812<div class="tablewrapadps"><a id="atomicdisplacement1" name="atomicdisplacement1"/> <span class="heading3">Atomic 813displacement parameters (�<sup>2</sup>)</span> 814<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 815<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 816<tr> 817<td class="tabledata"/> 818<td class="tabledata"><i>U</i><sup>11</sup></td> 819<td class="tabledata"><i>U</i><sup>22</sup></td> 820<td class="tabledata"><i>U</i><sup>33</sup></td> 821<td class="tabledata"><i>U</i><sup>12</sup></td> 822<td class="tabledata"><i>U</i><sup>13</sup></td> 823<td class="tabledata"><i>U</i><sup>23</sup></td> 824</tr> 825 826<tr> 827<td class="tabledata">Br1</td> 828<td class="tabledata">0.02442 (16)</td> 829<td class="tabledata">0.01848 (15)</td> 830<td class="tabledata">0.02622 (17)</td> 831<td class="tabledata"><span style="font-family:Times">?</span>0.00289 (11)</td> 832<td class="tabledata">0.00507 (11)</td> 833<td class="tabledata">0.00316 (11)</td> 834</tr> 835 836<tr> 837<td class="tabledata">F1</td> 838<td class="tabledata">0.0383 (10)</td> 839<td class="tabledata">0.0214 (9)</td> 840<td class="tabledata">0.0173 (8)</td> 841<td class="tabledata"><span style="font-family:Times">?</span>0.0032 (7)</td> 842<td class="tabledata">0.0014 (7)</td> 843<td class="tabledata"><span style="font-family:Times">?</span>0.0029 (6)</td> 844</tr> 845 846<tr> 847<td class="tabledata">N1</td> 848<td class="tabledata">0.0213 (11)</td> 849<td class="tabledata">0.0165 (11)</td> 850<td class="tabledata">0.0209 (11)</td> 851<td class="tabledata"><span style="font-family:Times">?</span>0.0001 (9)</td> 852<td class="tabledata">0.0072 (9)</td> 853<td class="tabledata">0.0004 (9)</td> 854</tr> 855 856<tr> 857<td class="tabledata">C1</td> 858<td class="tabledata">0.0220 (13)</td> 859<td class="tabledata">0.0195 (14)</td> 860<td class="tabledata">0.0163 (12)</td> 861<td class="tabledata">0.0024 (10)</td> 862<td class="tabledata">0.0015 (10)</td> 863<td class="tabledata"><span style="font-family:Times">?</span>0.0035 (10)</td> 864</tr> 865 866<tr> 867<td class="tabledata">C2</td> 868<td class="tabledata">0.0261 (14)</td> 869<td class="tabledata">0.0187 (13)</td> 870<td class="tabledata">0.0168 (13)</td> 871<td class="tabledata">0.0035 (10)</td> 872<td class="tabledata">0.0051 (11)</td> 873<td class="tabledata">0.0018 (10)</td> 874</tr> 875 876<tr> 877<td class="tabledata">C3</td> 878<td class="tabledata">0.0191 (12)</td> 879<td class="tabledata">0.0153 (12)</td> 880<td class="tabledata">0.0209 (13)</td> 881<td class="tabledata"><span style="font-family:Times">?</span>0.0006 (9)</td> 882<td class="tabledata">0.0066 (10)</td> 883<td class="tabledata">0.0012 (10)</td> 884</tr> 885 886<tr> 887<td class="tabledata">C4</td> 888<td class="tabledata">0.0221 (13)</td> 889<td class="tabledata">0.0231 (14)</td> 890<td class="tabledata">0.0187 (13)</td> 891<td class="tabledata"><span style="font-family:Times">?</span>0.0001 (11)</td> 892<td class="tabledata">0.0042 (11)</td> 893<td class="tabledata"><span style="font-family:Times">?</span>0.0006 (11)</td> 894</tr> 895 896<tr> 897<td class="tabledata">C5</td> 898<td class="tabledata">0.0231 (13)</td> 899<td class="tabledata">0.0197 (13)</td> 900<td class="tabledata">0.0185 (13)</td> 901<td class="tabledata">0.0003 (10)</td> 902<td class="tabledata">0.0034 (11)</td> 903<td class="tabledata">0.0022 (10)</td> 904</tr> 905 906<tr> 907<td class="tabledata">C6</td> 908<td class="tabledata">0.0192 (13)</td> 909<td class="tabledata">0.0142 (12)</td> 910<td class="tabledata">0.0196 (13)</td> 911<td class="tabledata">0.0031 (9)</td> 912<td class="tabledata">0.0064 (10)</td> 913<td class="tabledata">0.0015 (10)</td> 914</tr> 915 916<tr> 917<td class="tabledata">C7</td> 918<td class="tabledata">0.0182 (12)</td> 919<td class="tabledata">0.0151 (12)</td> 920<td class="tabledata">0.0210 (13)</td> 921<td class="tabledata">0.0016 (9)</td> 922<td class="tabledata">0.0042 (10)</td> 923<td class="tabledata"><span style="font-family:Times">?</span>0.0022 (10)</td> 924</tr> 925 926<tr> 927<td class="tabledata">C8</td> 928<td class="tabledata">0.0178 (12)</td> 929<td class="tabledata">0.0194 (12)</td> 930<td class="tabledata">0.0251 (14)</td> 931<td class="tabledata"><span style="font-family:Times">?</span>0.0027 (10)</td> 932<td class="tabledata">0.0055 (10)</td> 933<td class="tabledata"><span style="font-family:Times">?</span>0.0026 (11)</td> 934</tr> 935</table> 936</div> 937 938<!-- endtablewrapadpsdiv --> 939<div class="tablewrapgeomlong"><a id="geometricparameters1" name="geometricparameters1"/> <span class="heading3">Geometric 940parameters (�, �)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span> 941<!-- endtoplinkspan --><!-- startgeom --> 942<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 943<colgroup span="4"> 944<col width="30%"/> 945<col width="20%"/> 946<col width="30%"/> 947<col width="20%"/></colgroup> 948 949<tr> 950<td width="30%" class="tabledata">Br1-C3</td> 951<td width="20%" class="tabledata">1.895�(3)</td> 952<td width="30%" class="tabledata">C4-C5</td> 953<td width="20%" class="tabledata">1.387�(4)</td> 954</tr> 955 956<tr> 957<td width="30%" class="tabledata">F1-C1</td> 958<td width="20%" class="tabledata">1.366�(3)</td> 959<td width="30%" class="tabledata">C4-H4A</td> 960<td width="20%" class="tabledata">0.9300</td> 961</tr> 962 963<tr> 964<td width="30%" class="tabledata">N1-C7</td> 965<td width="20%" class="tabledata">1.265�(3)</td> 966<td width="30%" class="tabledata">C5-C6</td> 967<td width="20%" class="tabledata">1.398�(4)</td> 968</tr> 969 970<tr> 971<td width="30%" class="tabledata">N1-C8</td> 972<td width="20%" class="tabledata">1.460�(4)</td> 973<td width="30%" class="tabledata">C5-H5A</td> 974<td width="20%" class="tabledata">0.9300</td> 975</tr> 976 977<tr> 978<td width="30%" class="tabledata">C1-C2</td> 979<td width="20%" class="tabledata">1.373�(4)</td> 980<td width="30%" class="tabledata">C6-C7</td> 981<td width="20%" class="tabledata">1.472�(4)</td> 982</tr> 983 984<tr> 985<td width="30%" class="tabledata">C1-C6</td> 986<td width="20%" class="tabledata">1.387�(4)</td> 987<td width="30%" class="tabledata">C7-H7A</td> 988<td width="20%" class="tabledata">0.9300</td> 989</tr> 990 991<tr> 992<td width="30%" class="tabledata">C2-C3</td> 993<td width="20%" class="tabledata">1.382�(4)</td> 994<td width="30%" class="tabledata">C8-C8<sup>i</sup></td> 995<td width="20%" class="tabledata">1.521�(6)</td> 996</tr> 997 998<tr> 999<td width="30%" class="tabledata">C2-H2A</td> 1000<td width="20%" class="tabledata">0.9300</td> 1001<td width="30%" class="tabledata">C8-H8A</td> 1002<td width="20%" class="tabledata">0.9700</td> 1003</tr> 1004 1005<tr> 1006<td width="30%" class="tabledata">C3-C4</td> 1007<td width="20%" class="tabledata">1.391�(4)</td> 1008<td width="30%" class="tabledata">C8-H8B</td> 1009<td width="20%" class="tabledata">0.9700</td> 1010</tr> 1011 1012<tr> 1013<td width="25%" class="tabledata"/> 1014<td width="25%" class="tabledata"/> 1015<td width="25%" class="tabledata"/> 1016<td width="25%" class="tabledata"/> 1017</tr> 1018 1019<tr> 1020<td width="30%" class="tabledata">C7-N1-C8</td> 1021<td width="20%" class="tabledata">116.3�(2)</td> 1022<td width="30%" class="tabledata">C4-C5-H5A</td> 1023<td width="20%" class="tabledata">119.1</td> 1024</tr> 1025 1026<tr> 1027<td width="30%" class="tabledata">F1-C1-C2</td> 1028<td width="20%" class="tabledata">117.7�(2)</td> 1029<td width="30%" class="tabledata">C6-C5-H5A</td> 1030<td width="20%" class="tabledata">119.1</td> 1031</tr> 1032 1033<tr> 1034<td width="30%" class="tabledata">F1-C1-C6</td> 1035<td width="20%" class="tabledata">117.7�(2)</td> 1036<td width="30%" class="tabledata">C1-C6-C5</td> 1037<td width="20%" class="tabledata">116.2�(2)</td> 1038</tr> 1039 1040<tr> 1041<td width="30%" class="tabledata">C2-C1-C6</td> 1042<td width="20%" class="tabledata">124.6�(3)</td> 1043<td width="30%" class="tabledata">C1-C6-C7</td> 1044<td width="20%" class="tabledata">121.8�(2)</td> 1045</tr> 1046 1047<tr> 1048<td width="30%" class="tabledata">C1-C2-C3</td> 1049<td width="20%" class="tabledata">116.8�(3)</td> 1050<td width="30%" class="tabledata">C5-C6-C7</td> 1051<td width="20%" class="tabledata">122.0�(2)</td> 1052</tr> 1053 1054<tr> 1055<td width="30%" class="tabledata">C1-C2-H2A</td> 1056<td width="20%" class="tabledata">121.6</td> 1057<td width="30%" class="tabledata">N1-C7-C6</td> 1058<td width="20%" class="tabledata">121.6�(2)</td> 1059</tr> 1060 1061<tr> 1062<td width="30%" class="tabledata">C3-C2-H2A</td> 1063<td width="20%" class="tabledata">121.6</td> 1064<td width="30%" class="tabledata">N1-C7-H7A</td> 1065<td width="20%" class="tabledata">119.2</td> 1066</tr> 1067 1068<tr> 1069<td width="30%" class="tabledata">C2-C3-C4</td> 1070<td width="20%" class="tabledata">122.2�(2)</td> 1071<td width="30%" class="tabledata">C6-C7-H7A</td> 1072<td width="20%" class="tabledata">119.2</td> 1073</tr> 1074 1075<tr> 1076<td width="30%" class="tabledata">C2-C3-Br1</td> 1077<td width="20%" class="tabledata">119.2�(2)</td> 1078<td width="30%" class="tabledata">N1-C8-C8<sup>i</sup></td> 1079<td width="20%" class="tabledata">109.6�(3)</td> 1080</tr> 1081 1082<tr> 1083<td width="30%" class="tabledata">C4-C3-Br1</td> 1084<td width="20%" class="tabledata">118.6�(2)</td> 1085<td width="30%" class="tabledata">N1-C8-H8A</td> 1086<td width="20%" class="tabledata">109.8</td> 1087</tr> 1088 1089<tr> 1090<td width="30%" class="tabledata">C5-C4-C3</td> 1091<td width="20%" class="tabledata">118.4�(3)</td> 1092<td width="30%" class="tabledata">C8<sup>i</sup>-C8-H8A</td> 1093<td width="20%" class="tabledata">109.8</td> 1094</tr> 1095 1096<tr> 1097<td width="30%" class="tabledata">C5-C4-H4A</td> 1098<td width="20%" class="tabledata">120.8</td> 1099<td width="30%" class="tabledata">N1-C8-H8B</td> 1100<td width="20%" class="tabledata">109.8</td> 1101</tr> 1102 1103<tr> 1104<td width="30%" class="tabledata">C3-C4-H4A</td> 1105<td width="20%" class="tabledata">120.8</td> 1106<td width="30%" class="tabledata">C8<sup>i</sup>-C8-H8B</td> 1107<td width="20%" class="tabledata">109.8</td> 1108</tr> 1109 1110<tr> 1111<td width="30%" class="tabledata">C4-C5-C6</td> 1112<td width="20%" class="tabledata">121.9�(3)</td> 1113<td width="30%" class="tabledata">H8A-C8-H8B</td> 1114<td width="20%" class="tabledata">108.2</td> 1115</tr> 1116 1117<tr> 1118<td width="25%" class="tabledata"/> 1119<td width="25%" class="tabledata"/> 1120<td width="25%" class="tabledata"/> 1121<td width="25%" class="tabledata"/> 1122</tr> 1123 1124<tr> 1125<td width="30%" class="tabledata">F1-C1-C2-C3</td> 1126<td width="20%" class="tabledata"><span style="font-family:Times">?</span>179.0�(2)</td> 1127<td width="30%" class="tabledata">F1-C1-C6-C7</td> 1128<td width="20%" class="tabledata">2.4�(4)</td> 1129</tr> 1130 1131<tr> 1132<td width="30%" class="tabledata">C6-C1-C2-C3</td> 1133<td width="20%" class="tabledata">1.3�(4)</td> 1134<td width="30%" class="tabledata">C2-C1-C6-C7</td> 1135<td width="20%" class="tabledata"><span style="font-family:Times">?</span>177.9�(3)</td> 1136</tr> 1137 1138<tr> 1139<td width="30%" class="tabledata">C1-C2-C3-C4</td> 1140<td width="20%" class="tabledata"><span style="font-family:Times">?</span>1.5�(4)</td> 1141<td width="30%" class="tabledata">C4-C5-C6-C1</td> 1142<td width="20%" class="tabledata"><span style="font-family:Times">?</span>1.1�(4)</td> 1143</tr> 1144 1145<tr> 1146<td width="30%" class="tabledata">C1-C2-C3-Br1</td> 1147<td width="20%" class="tabledata">176.3�(2)</td> 1148<td width="30%" class="tabledata">C4-C5-C6-C7</td> 1149<td width="20%" class="tabledata">176.7�(3)</td> 1150</tr> 1151 1152<tr> 1153<td width="30%" class="tabledata">C2-C3-C4-C5</td> 1154<td width="20%" class="tabledata">0.4�(4)</td> 1155<td width="30%" class="tabledata">C8-N1-C7-C6</td> 1156<td width="20%" class="tabledata"><span style="font-family:Times">?</span>178.5�(2)</td> 1157</tr> 1158 1159<tr> 1160<td width="30%" class="tabledata">Br1-C3-C4-C5</td> 1161<td width="20%" class="tabledata"><span style="font-family:Times">?</span>177.4�(2)</td> 1162<td width="30%" class="tabledata">C1-C6-C7-N1</td> 1163<td width="20%" class="tabledata"><span style="font-family:Times">?</span>165.9�(3)</td> 1164</tr> 1165 1166<tr> 1167<td width="30%" class="tabledata">C3-C4-C5-C6</td> 1168<td width="20%" class="tabledata">1.0�(4)</td> 1169<td width="30%" class="tabledata">C5-C6-C7-N1</td> 1170<td width="20%" class="tabledata">16.4�(4)</td> 1171</tr> 1172 1173<tr> 1174<td width="30%" class="tabledata">F1-C1-C6-C5</td> 1175<td width="20%" class="tabledata"><span style="font-family:Times">?</span>179.8�(2)</td> 1176<td width="30%" class="tabledata">C7-N1-C8-C8<sup>i</sup></td> 1177<td width="20%" class="tabledata"><span style="font-family:Times">?</span>115.8�(3)</td> 1178</tr> 1179 1180<tr> 1181<td width="30%" class="tabledata">C2-C1-C6-C5</td> 1182<td width="20%" class="tabledata"><span style="font-family:Times">?</span>0.1�(4)</td> 1183<td width="30%" class="tabledata"/> 1184<td width="20%" class="tabledata"/> 1185</tr> 1186</table> 1187 1188<table style="table-layout:fixed" width="100%" class="noborder"> 1189<tr> 1190<td class="tabledata">Symmetry codes: (i) ?<i>x</i>, 1191?<i>y</i>, ?<i>z</i>.</td> 1192</tr> 1193</table> 1194</div> 1195 1196<!-- endtablewrapgeomlongdiv --> 1197<div class="tablewraphbondslong"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3">Hydrogen-bond geometry (�, �)</span> 1198<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1199<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 1200<colgroup span="5"> 1201<col width="40%"/> 1202<col width="15%"/> 1203<col width="15%"/> 1204<col width="15%"/> 1205<col width="15%"/></colgroup> 1206 1207<tr> 1208<td width="40%" class="tabledata"> 1209<i>D</i>-H���<i>A</i></td> 1210<td width="15%" class="tabledata"><i>D</i>-H</td> 1211<td width="15%" class="tabledata">H���<i>A</i></td> 1212<td width="15%" class="tabledata"> 1213<i>D</i>���<i>A</i></td> 1214<td width="15%" class="tabledata"> 1215<i>D</i>-H���<i>A</i></td> 1216</tr> 1217 1218<tr> 1219<td width="40%" class="tabledata"> 1220C2-H2A���N1<sup>ii</sup></td> 1221<td width="15%" class="tabledata">0.93</td> 1222<td width="15%" class="tabledata">2.53</td> 1223<td width="15%" class="tabledata">3.386�(3)</td> 1224<td width="15%" class="tabledata">154.</td> 1225</tr> 1226</table> 1227 1228<table style="table-layout:fixed" width="100%" class="noborder"> 1229<tr> 1230<td class="tabledata">Symmetry codes: (ii) <i>x</i>, 1231?<i>y</i>?1/2, <i>z</i>+1/2.</td> 1232</tr> 1233</table> 1234</div> 1235 1236<!-- endtablewraphbondslongdiv --><!-- endcoord --><!-- endadp --> 1237<!-- startgeom --><!-- endgeom --> 1238<div class="tablewraphbondsshort"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3"><span class="tablenum"><b>Table 1</b></span><br/> 1239Hydrogen-bond geometry (�, �)</span> 1240<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1241<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 1242<colgroup span="5"> 1243<col width="40%"/> 1244<col width="15%"/> 1245<col width="15%"/> 1246<col width="15%"/> 1247<col width="15%"/></colgroup> 1248 1249<tr> 1250<td width="40%" class="tabledata"> 1251<i>D</i>-H���<i>A</i></td> 1252<td width="15%" class="tabledata"><i>D</i>-H</td> 1253<td width="15%" class="tabledata">H���<i>A</i></td> 1254<td width="15%" class="tabledata"> 1255<i>D</i>���<i>A</i></td> 1256<td width="15%" class="tabledata"> 1257<i>D</i>-H���<i>A</i></td> 1258</tr> 1259 1260<tr> 1261<td width="40%" class="tabledata"> 1262C2-H2A���N1<sup>i</sup></td> 1263<td width="15%" class="tabledata">0.93</td> 1264<td width="15%" class="tabledata">2.53</td> 1265<td width="15%" class="tabledata">3.386�(3)</td> 1266<td width="15%" class="tabledata">154.</td> 1267</tr> 1268</table> 1269 1270<table style="table-layout:fixed" width="100%" class="noborder"> 1271<tr> 1272<td class="tabledata">Symmetry codes: (i) <i>x</i>, 1273?<i>y</i>?1/2, <i>z</i>+1/2.</td> 1274</tr> 1275</table> 1276</div> 1277 1278<!-- endtablewraphbondsshortdiv --> 1279</div> 1280 1281<!-- enddatablockdiv --><a id="extratables" name="extratables"/> 1282 1283 1284<div class="acknowledgements"><a id="acknowledgements" name="acknowledgements"/> 1285 1286<div class="heading2">Acknowledgements <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1287</div> 1288 1289<!-- endheading2div --> 1290<p>HKF and RK thank the Malaysian Government and Universiti Sains 1291Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK 1292thanks Universiti Sains Malaysia for the award of a post-doctoral 1293research fellowship.</p> 1294</div> 1295 1296<!-- endacknowledgementsdiv --> 1297<div class="references"><a id="references" name="references"/><a class="buttons" title="link to reference list" href="./at2629bdy.html#References">references</a></div> 1298 1299<!-- endreferencesdiv --> 1300<div class="publreferences"><a id="publreferences" name="publreferences"/> 1301 1302<div class="heading2">References <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1303</div> 1304 1305<!-- endheading2div --> 1306<p>Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. 1307G. & Taylor, R. (1987). <i>J. Chem. Soc. Perkin Trans. 2</i>, 1308pp. S1-S19.<br/> 1309<br/> 1310Brammer, L., Espallargas, M. E. & Adams, H. (2003). 1311<i>CrystEngComm</i>, <b>5</b>, 343-345.<br/> 1312<br/> 1313Bruker (2005). <i>APEX2</i>, <i>SAINT</i> and <i>SADABS</i>. Bruker 1314AXS Inc., Madison, Wisconsin, USA.<br/> 1315<br/> 1316Calligaris, M. & Randaccio, L. (1987). <i>Comprehensive 1317Coordination Chemistry</i>, Vol. 2, edited by G. Wilkinson, pp. 1318715-738. London: Pergamon.<br/> 1319<br/> 1320Fun, H.-K., Kargar, H. & Kia, R. (2008). <i>Acta Cryst.</i> 1321E<b>64</b>, o1894.<br/> 1322<br/> 1323Fun, H.-K. & Kia, R. (2008<i>a</i>). <i>Acta Cryst.</i> 1324E<b>64</b>, o1722-o1723.<br/> 1325<br/> 1326Fun, H.-K. & Kia, R. (2008<i>b</i>). <i>Acta Cryst.</i> 1327E<b>64</b>, o1870-o1871.<br/> 1328<br/> 1329Fun, H.-K. & Kia, R. (2008<i>c</i>). <i>Acta Cryst.</i>, 1330E<b>64</b>, submitted <b>[CV2444]</b>.<br/> 1331<br/> 1332Hou, B., Friedman, N., Ruhman, S., Sheves, M. & Ottolenghi, M. 1333(2001). <i>J. Phys. Chem. B</i>, <b>105</b>, 7042-7048.<br/> 1334<br/> 1335Pal, S., Barik, A. K., Gupta, S., Hazra, A., Kar, S. K., Peng, 1336S.-M., Lee, G.-H., Butcher, R. J., El Fallah, M. S. & Ribas, J. 1337(2005). <i>Inorg. Chem.</i> <b>44</b>, 3880-3889.<br/> 1338<br/> 1339Ramasubbu, N., Parthasathy, R. & Murry-Rust, P. (1986). <i>J. 1340Am. Chem. Soc.</i> <b>108</b>, 4308-4314.<br/> 1341<br/> 1342Ren, S., wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., 1343McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). 1344<i>J. Med. Chem.</i> <b>45</b>, 410-419.<br/> 1345<br/> 1346Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>, 1347112-122.<br/> 1348<br/> 1349Spek, A. L. (2003). <i>J. Appl. Cryst.</i> <b>36</b>, 7-13.<br/> 1350<br/> 1351</p> 1352</div> 1353 1354<!-- endpublreferencesdiv --> 1355<br/> 1356<br/> 1357<br/> 1358<br/> 1359<br/> 1360<br/> 1361<br/> 1362<br/> 1363<br/> 1364<br/> 1365<br/> 1366<br/> 1367<br/> 1368<br/> 1369<br/> 1370<br/> 1371<br/> 1372<br/> 1373<br/> 1374<br/> 1375<br/> 1376<br/> 1377<br/> 1378<br/> 1379<br/> 1380<br/> 1381<br/> 1382<br/> 1383<br/> 1384<br/> 1385<br/> 1386<br/> 1387<br/> 1388<br/> 1389<br/> 1390<br/> 1391<br/> 1392<br/> 1393<br/> 1394<br/> 1395<br/> 1396<br/> 1397<br/> 1398<br/> 1399<br/> 1400</body> 1401</html>