/html/8/b/e/8be7286f-f12a-414e-b7ab-fff9366bd642/suppText.html
HTML | 1382 lines | 1138 code | 193 blank | 51 comment | 0 complexity | 2e8416bb63aecd74e5877f27698ddb10 MD5 | raw file
1<?xml version="1.0" encoding="UTF-8"?> 2<html cmlx:fileId="C:\Users\pm286\workspace\crystaleyeTestData\html\8\b\e\8be7286f-f12a-414e-b7ab-fff9366bd642\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) ? "https://ssl." : "http://www."); 25document.write(unescape("%3Cscript src='" + gaJsHost 26+ "google-analytics.com/ga.js' type='text/javascript'%3E%3C/script%3E")); 27</script> 28 29<script type="text/javascript"> 30var pageTracker = _gat._getTracker("UA-187984-3"); 31pageTracker._trackPageview(); 32</script> 33 34<link href="../../../../../styles/publcif.css" rel="stylesheet" type="text/css"/> 35</head> 36<body bgcolor="#FFFFFF" text="#000000"> 37<a id="top" name="top"/> 38<h1 class="suptitle">supplementary materials</h1> 39 40<br/> 41<div class="buttonlinks"><a href="./index.html" target="_parent"><img src="../../../../../graphics/htmlborder.gif" alt="HTML version" align="top" border="0"/></a><a href="./at2623.pdf"><img src="../../../../../graphics/pdfborder.gif" alt="pdf version" align="top" border="0"/></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?at2623sup1"><img src="../../../../../graphics/cifborder.gif" alt="cif file" align="top" border="0"/></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?at2623sup1&Qmime=cif"> 42<img src="../../../../../graphics/3dviewborder.gif" alt="3d view" align="top" border="0"/></a><a href="./at2623Isup2.hkl"><img src="../../../../../graphics/structurefactorsborder.gif" alt="structure factors" align="top" border="0"/></a><a href="./at2623sup0.html"><img src="../../../../../graphics/supplementarymaterialsborder.gif" alt="supplementary materials" align="top" border="0"/></a><a href="./at2623checkcif.html"><img src="../../../../../graphics/checkcifborder.gif" alt="CIF check report" align="top" border="0"/></a><a href="http://scripts.iucr.org/cgi-bin/citedin?at2623"><img src="../../../../../graphics/citedinborder.gif" alt="cited in" align="top" border="0"/></a><a href="http://scripts.iucr.org/cgi-bin/similar?wordList=iodobenzylidene%20or%20ethane%20or%20diamine&from=at2623"> 43<img src="../../../../../graphics/similarpapersborder.gif" alt="similar papers" align="top" border="0"/></a>�<a href="../../../../../../services/openaccess.html"><img src="../../../../../../logos/free.gif" alt="Open access" align="top" border="0"/></a></div> 44 45<div class="bibline"> 46<p><i>Acta Cryst.</i> (2008). E<b>64</b>, 47o1870-o1871����[ <a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536808027608">doi:10.1107/S1600536808027608</a> 48]</p> 49</div> 50 51<h3><span class="it"><i>N</i></span>,<span class="it"><i>N</i></span>'-Bis(2-iodobenzylidene)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>14</sub></span>I<span class="inf"><sub>2</sub></span>N<span class="inf"><sub>2</sub></span>, lies across a crystallographic 64inversion centre. An intramolecular C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif"/>I hydrogen bond forms a 65five-membered ring, producing an <span class="it"><i>S</i></span>(5) ring motif. The C=N bond is coplanar 66with the benzene ring and adopts a <span class="it"><i>trans</i></span> configuration. 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 I<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif"/>N 70[3.2096�(15)��] interaction, which is significantly 71shorter than the sum of the van der Waals radii of these atoms. In 72the crystal structure, molecules are linked into one-dimensional 73extended chains along the <span class="it"><i>c</i></span> axis and 74also into one-dimensional extended chains along the <span class="it"><i>b</i></span> axis through short intermolecular I<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif"/>N 75interactions, forming two-dimensional networks parallel to the 76<span class="it"><i>bc</i></span> plane.</p> 77</div> 78 79<!-- endabstractdiv --> 80<div class="contentslist"> 81<ul> 82<li class="comment"><a title="Comment" href="#comment">Comment</a></li> 83 84<li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li> 85 86<li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li> 87 88<li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li> 89 90<li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li> 91 92<li class="figures"><a title="Figures" href="#figures">Figures</a></li> 93 94<li><a title="(I)" href="#chemicalname1">N,N'-Bis(2-iodobenzylidene)ethane-1,2-diamine</a> 95 96 97<ul> 98<li><a title="Crystal data" href="#crystaldata1">Crystal 99data</a></li> 100 101<li><a title="Data collection" href="#datacollection1">Data 102collection</a></li> 103 104<li><a title="Refinement data" href="#refinementdata1">Refinement 105data</a></li> 106 107<li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li> 108 109<li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic 110coordinates</a></li> 111 112<li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li> 113 114<li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li> 115 116<li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 117 118<li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 119</ul> 120</li> 121 122<li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li> 123 124<li class="publreferences"><a title="References" href="#publreferences">References</a></li> 125</ul> 126</div> 127 128<!-- endcontentslistdiv --> 129<div class="comment"><a id="comment" name="comment"/> 130 131<div class="heading2">Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 132</div> 133 134<!-- endheading2div --> 135<p>Schiff bases are one of most prevalent mixed-donor ligands in 136the field of coordination chemistry. Schiff bases have been used 137widely as ligands in the formation of transition metal complexes. 138Many such complexes have been structurally characterized, but only 139a relatively small number of free Schiff base ligands have been 140characterized (Calligaris & Randaccio, 1987). There has been 141growing interest in Schiff base ligands, mainly because of their 142wide application in the field of biochemistry, synthesis, and 143catalysis (Pal <i>et al.</i>, 2005; Hou <i>et al.</i>, 2001; Ren 144<i>et al.</i>, 2002). As an extension of our work (Fun, Kia & 145Kargar 2008; Fun, Kargar & Kia 2008; Fun, Mirkhani <i>et 146al.</i> 2008) on the structural characterization of Schiff base 147compounds, the title compound (I), is reported here.</p> 148 149<p>The molecule of the title compound, (I), (Fig. 1), lies across a 150crystallographic inversion centre. The bond lengths and angles are 151within normal ranges (Allen <i>et al.</i>,1987). An intramolecular 152C-H���I hydrogen bond (Brammer <i>et al.</i> 2001) 153forms a five-membered ring, producing an <i>S</i>(5) ring motif 154(Bernstein <i>et al.</i>, 1995) (Table 1). The asymmetric unit of 155the compound is composed of one-half of the molecule. The C<span style="font-family:Times">?</span>N bond is coplanar with the 156benzene ring and adopts a <i>trans</i> configuration. Within the 157molecule, the planar units are parallel, but extend in opposite 158directions from the methylene bridge. The interesting feature of 159the crystal structure is the short I���N 160[3.2096�(15) �] interactions (Lommerse <i>et al.</i> 1611996), which is significantly shorter than the sum of the van der 162Waals radii of the relevant atoms. In the crystal structure, 163molecules are linked into 1-D extended chains along the <i>c</i> 164axis and are also into 1-D extended chains along the <i>b</i> axis 165through short intermolecular I���N interactions 166forming 2-D networks (Fig. 2 & 3) which are parallel to the 167<i>bc</i> plane.</p> 168</div> 169 170<!-- endcommentdiv --> 171<div class="relatedliterature"><a id="relatedliterature" name="relatedliterature"/> 172 173<div class="heading2">Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 174</div> 175 176<!-- endheading2div --> 177<p>For bond-length data, see: Allen <i>et al.</i> (1987). For 178hydrogen-bond motifs, see: Bernstein <i>et al.</i> (1995). For the 179hydrogen bond capability of halogens, see: Brammer <i>et al.</i> 180(2001). For halogen-electronegative atom interactions, see: 181Lommerse <i>et al.</i> (1996). For related structures, see, for 182example: Fun, Kia & Kargar (2008); Fun, Kargar & Kia 183(2008); Fun, Mirkhani <i>et al.</i> (2008); Calligaris & 184Randaccio, (1987). For information on Schiff base lignads and their 185complexes and their applications, see, for example: Pal <i>et 186al.</i> (2005); Hou <i>et al.</i> (2001); Ren <i>et al.</i> 187(2002).</p> 188</div> 189 190<!-- endrelatedliteraturediv --> 191<div class="experimental"><a id="experimental" name="experimental"/> 192 193<div class="heading2">Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 194</div> 195 196<!-- endheading2div --> 197<p>The synthetic method has been described earlier (Fun, Kia & 198Kargar <i>et al.</i>, 2008). Single crystals suitable for 199<i>X</i>-ray diffraction were obtained by evaporation of an ethanol 200solution at room temperature.</p> 201</div> 202 203<!-- endexperimentaldiv --> 204<div class="refinement"><a id="refinement" name="refinement"/> 205 206<div class="heading2">Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 207</div> 208 209<!-- endheading2div --> 210<p>All of the H atoms were located from the difference Fourier map 211and freely refined. The highest peak is located 0.61 � from C5 212and the deepest hole is located 0.63 � from I1.</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="./at2623scheme1.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="./at2623fig1.html"><img width="100" src="./at2623fig1thm.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>, 1 - <i>y</i>, -<i>z</i>]. 250</td> 251</tr> 252 253<tr> 254<td class="nodecs" align="center" width="110"><a href="./at2623fig2.html"><img width="100" src="./at2623fig2thm.gif" alt="[Figure 2]" align="middle"/></a> </td> 255<td class="nodecs" valign="middle">Fig. 2. The crystal packing of 256(I), viewed down the <i>b</i> axis, showing 1-D extended chains 257along the <i>c</i> axis. Intra- and intermolecular interactions are 258shown as dashed lines. </td> 259</tr> 260 261<tr> 262<td class="nodecs" align="center" width="110"><a href="./at2623fig3.html"><img width="100" src="./at2623fig3thm.gif" alt="[Figure 3]" align="middle"/></a> </td> 263<td class="nodecs" valign="middle">Fig. 3. The crystal packing of 264(I), viewed down the <i>c</i>-axis showing 1-D extended chains 265along the <i>b</i>-axis. Intra and intermolecular interactions are 266shown as dashed lines. </td> 267</tr> 268</table> 269</div> 270 271<!-- endfiguresdiv --> 272<div class="datablock1"> 273<div class="heading2"><a id="chemicalname1" name="chemicalname1"/>N,N'-Bis(2-iodobenzylidene)ethane-1,2-diamine 274<span class="toplink"><a class="buttons" href="#top">top</a></span> 275<!-- endtoplinkspan --> 276</div> 277 278<!-- endheading2div --> 279<div class="tablewrapcrystaldatalong"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span> 280<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 281<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 282<colgroup span="2"> 283<col width="50%"/> 284<col width="50%"/></colgroup> 285 286<tr> 287<td width="50%" class="tabledata"> 288C<sub>16</sub>H<sub>14</sub>I<sub>2</sub>N<sub>2</sub></td> 289<td width="50%" class="tabledata"><i>F</i>(000) = 460</td> 290</tr> 291 292<tr> 293<td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> = 294488.09</td> 295<td width="50%" class="tabledata"><i>D</i><sub>x</sub> = 1.993 Mg 296m<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 297</tr> 298 299<tr> 300<td width="50%" class="tabledata">Monoclinic, 301<i>P</i>2<sub>1</sub>/<i>c</i></td> 302<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> 303</tr> 304 305<tr> 306<td width="50%" class="tabledata">Hall symbol: -P 2ybc</td> 307<td width="50%" class="tabledata">Cell parameters from 7125 308reflections</td> 309</tr> 310 311<tr> 312<td width="50%" class="tabledata"><i>a</i> = 12.1820 (4) 313�</td> 314<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 2.8-38.9�</td> 315</tr> 316 317<tr> 318<td width="50%" class="tabledata"><i>b</i> = 4.5978 (1) �</td> 319<td width="50%" class="tabledata">� = 3.86 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td> 320</tr> 321 322<tr> 323<td width="50%" class="tabledata"><i>c</i> = 14.5664 (4) 324�</td> 325<td width="50%" class="tabledata"><i>T</i> = 100 K</td> 326</tr> 327 328<tr> 329<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 94.424 (2)�</td> 330<td width="50%" class="tabledata">Plate, colourless</td> 331</tr> 332 333<tr> 334<td width="50%" class="tabledata"><i>V</i> = 813.44 (4) 335�<sup>3</sup></td> 336<td width="50%" class="tabledata">0.51 � 0.14 � 0.02 337mm</td> 338</tr> 339 340<tr> 341<td width="50%" class="tabledata"><i>Z</i> = 2</td> 342<td width="50%" class="tabledata"/> 343</tr> 344</table> 345 346<!-- endtabledatatable --> 347</div> 348 349<!-- endtablewrapcrystaldatalongdiv --> 350<div class="tablewrapdatacollectionlong"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data 351collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 352<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 353<colgroup span="2"> 354<col width="50%"/> 355<col width="50%"/></colgroup> 356 357<tr> 358<td width="50%" class="tabledata">Bruker SMART APEXII CCD 359area-detector<br/> 360diffractometer</td> 361<td width="50%" class="tabledata">4235 independent reflections</td> 362</tr> 363 364<tr> 365<td width="50%" class="tabledata">Radiation source: fine-focus 366sealed tube</td> 367<td width="50%" class="tabledata">3466 reflections with <i>I</i> 368> 2<span style="font-family:Times">?</span>(<i>I</i>)</td> 369</tr> 370 371<tr> 372<td width="50%" class="tabledata">graphite</td> 373<td width="50%" class="tabledata"><i>R</i><sub>int</sub> = 3740.044</td> 375</tr> 376 377<tr> 378<td width="50%" class="tabledata"><span style="font-family:Times">?</span> and <span style="font-family:Times">?</span> scans</td> 379<td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>max</sub> = 37.5�, 380<span style="font-family:Times">?</span><sub>min</sub> = 3811.7�</td> 382</tr> 383 384<tr> 385<td width="50%" class="tabledata">Absorption correction: 386multi-scan<br/> 387(SADABS; Bruker, 2005)</td> 388<td width="50%" class="tabledata"><i>h</i> = <span style="font-family:Times">?</span>19<span style="font-family:Times">?</span>20</td> 389</tr> 390 391<tr> 392<td width="50%" class="tabledata"><i>T</i><sub>min</sub> = 0.244, 393<i>T</i><sub>max</sub> = 0.917</td> 394<td width="50%" class="tabledata"><i>k</i> = <span style="font-family:Times">?</span>7<span style="font-family:Times">?</span>7</td> 395</tr> 396 397<tr> 398<td width="50%" class="tabledata">24819 measured reflections</td> 399<td width="50%" class="tabledata"><i>l</i> = <span style="font-family:Times">?</span>24<span style="font-family:Times">?</span>24</td> 400</tr> 401</table> 402 403<!-- endtabledatatable --> 404</div> 405 406<!-- endtablewrapdatacollectionlongdiv --> 407<div class="tablewraprefinementdatalong"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span> 408<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 409<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 410<colgroup span="2"> 411<col width="50%"/> 412<col width="50%"/></colgroup> 413 414<tr> 415<td width="50%" class="tabledata">Refinement on 416<i>F</i><sup>2</sup></td> 417<td width="50%" class="tabledata">Primary atom site location: 418structure-invariant direct methods</td> 419</tr> 420 421<tr> 422<td width="50%" class="tabledata">Least-squares matrix: full</td> 423<td width="50%" class="tabledata">Secondary atom site location: 424difference Fourier map</td> 425</tr> 426 427<tr> 428<td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup> 429> 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] = 4300.031</td> 431<td width="50%" class="tabledata">Hydrogen site location: inferred 432from neighbouring sites</td> 433</tr> 434 435<tr> 436<td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) = 4370.074</td> 438<td width="50%" class="tabledata">All H-atom parameters 439refined</td> 440</tr> 441 442<tr> 443<td width="50%" class="tabledata"><i>S</i> = 1.16</td> 444<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> 4452</sup>) + (0.0295<i>P</i>)<sup>2</sup> + 0.1458<i>P</i>]<br/> 446where <i>P</i> = (<i>F</i><sub>o</sub><sup>2</sup> + 4472<i>F</i><sub>c</sub><sup>2</sup>)/3</td> 448</tr> 449 450<tr> 451<td width="50%" class="tabledata">4235 reflections</td> 452<td width="50%" class="tabledata">(?/<span style="font-family:Times">?</span>)<sub>max</sub> = 0.001</td> 453</tr> 454 455<tr> 456<td width="50%" class="tabledata">115 parameters</td> 457<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 1.89 e 458�<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 459</tr> 460 461<tr> 462<td width="50%" class="tabledata">0 restraints</td> 463<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>1.74 e �<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 464</tr> 465</table> 466 467<!-- endtabledatatable --> 468</div> 469 470<!-- endtablewraprefinementdatalongdiv --> 471<div class="tablewrapcrystaldatashort"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span> 472<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 473<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 474<colgroup span="2"> 475<col width="50%"/> 476<col width="50%"/></colgroup> 477 478<tr> 479<td width="50%" class="tabledata"> 480C<sub>16</sub>H<sub>14</sub>I<sub>2</sub>N<sub>2</sub></td> 481<td width="50%" class="tabledata"><i>V</i> = 813.44 (4) 482�<sup>3</sup></td> 483</tr> 484 485<tr> 486<td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> = 487488.09</td> 488<td width="50%" class="tabledata"><i>Z</i> = 2</td> 489</tr> 490 491<tr> 492<td width="50%" class="tabledata">Monoclinic, 493<i>P</i>2<sub>1</sub>/<i>c</i></td> 494<td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span> radiation</td> 495</tr> 496 497<tr> 498<td width="50%" class="tabledata"><i>a</i> = 12.1820 (4) 499�</td> 500<td width="50%" class="tabledata">� = 3.86 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td> 501</tr> 502 503<tr> 504<td width="50%" class="tabledata"><i>b</i> = 4.5978 (1) �</td> 505<td width="50%" class="tabledata"><i>T</i> = 100 K</td> 506</tr> 507 508<tr> 509<td width="50%" class="tabledata"><i>c</i> = 14.5664 (4) 510�</td> 511<td width="50%" class="tabledata">0.51 � 0.14 � 0.02 512mm</td> 513</tr> 514 515<tr> 516<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 94.424 (2)�</td> 517<td width="50%" class="tabledata"/> 518</tr> 519</table> 520 521<!-- endtabledatatable --> 522</div> 523 524<!-- endtablewrapcrystaldatashortdiv --> 525<div class="tablewrapdatacollectionshort"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data 526collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 527<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 528<colgroup span="2"> 529<col width="50%"/> 530<col width="50%"/></colgroup> 531 532<tr> 533<td width="50%" class="tabledata">Bruker SMART APEXII CCD 534area-detector<br/> 535diffractometer</td> 536<td width="50%" class="tabledata">4235 independent reflections</td> 537</tr> 538 539<tr> 540<td width="50%" class="tabledata">Absorption correction: 541multi-scan<br/> 542(SADABS; Bruker, 2005)</td> 543<td width="50%" class="tabledata">3466 reflections with <i>I</i> 544> 2<span style="font-family:Times">?</span>(<i>I</i>)</td> 545</tr> 546 547<tr> 548<td width="50%" class="tabledata"><i>T</i><sub>min</sub> = 0.244, 549<i>T</i><sub>max</sub> = 0.917</td> 550<td width="50%" class="tabledata"><i>R</i><sub>int</sub> = 5510.044</td> 552</tr> 553 554<tr> 555<td width="50%" class="tabledata">24819 measured reflections</td> 556<td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>max</sub> = 55737.5�</td> 558</tr> 559</table> 560 561<!-- endtabledatatable --> 562</div> 563 564<!-- endtablewrapdatacollectionshortdiv --> 565<div class="tablewraprefinementdatashort"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span> 566<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 567<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 568<colgroup span="2"> 569<col width="50%"/> 570<col width="50%"/></colgroup> 571 572<tr> 573<td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup> 574> 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] = 5750.031</td> 576<td width="50%" class="tabledata">All H-atom parameters 577refined</td> 578</tr> 579 580<tr> 581<td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) = 5820.074</td> 583<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 1.89 e 584�<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 585</tr> 586 587<tr> 588<td width="50%" class="tabledata"><i>S</i> = 1.16</td> 589<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>1.74 e �<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 590</tr> 591 592<tr> 593<td width="50%" class="tabledata">4235 reflections</td> 594<td width="50%" class="tabledata">Absolute structure: ?</td> 595</tr> 596 597<tr> 598<td width="50%" class="tabledata">115 parameters</td> 599<td width="50%" class="tabledata">Flack parameter: ?</td> 600</tr> 601 602<tr> 603<td width="50%" class="tabledata">0 restraints</td> 604<td width="50%" class="tabledata">Rogers parameter: ?</td> 605</tr> 606</table> 607 608<!-- endtabledatatable --> 609</div> 610 611<!-- endtablewraprefinementdatashortdiv --> 612<div class="specialdetails"><a id="specialdetails1" name="specialdetails1"/><span class="heading3">Special 613details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 614<table style="table-layout:fixed" width="100%" class="tabledata"> 615<tr> 616<td class="tabledata"> 617<p><b>Experimental</b>. The low-temperature data was collected with 618the Oxford Cyrosystem Cobra low-temperature attachment.</p> 619</td> 620</tr> 621 622<tr> 623<td class="tabledata"> 624<p><b>Geometry</b>. All e.s.d.'s (except the e.s.d. in the 625dihedral angle between two l.s. planes) are estimated using the 626full covariance matrix. The cell e.s.d.'s are taken into 627account individually in the estimation of e.s.d.'s in 628distances, angles and torsion angles; correlations between 629e.s.d.'s in cell parameters are only used when they are defined 630by crystal symmetry. An approximate (isotropic) treatment of cell 631e.s.d.'s is used for estimating e.s.d.'s involving l.s. 632planes.</p> 633</td> 634</tr> 635 636<tr> 637<td class="tabledata"> 638<p><b>Refinement</b>. Refinement of <i>F</i><sup>2</sup> against 639ALL reflections. The weighted <i>R</i>-factor <i>wR</i> and 640goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, 641conventional <i>R</i>-factors <i>R</i> are based on <i>F</i>, with 642<i>F</i> set to zero for negative <i>F</i><sup>2</sup>. The 643threshold expression of <i>F</i><sup>2</sup> > <span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>) is 644used only for calculating <i>R</i>-factors(gt) <i>etc</i>. and is 645not relevant to the choice of reflections for refinement. 646<i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically 647about twice as large as those based on <i>F</i>, and <i>R</i>- 648factors based on ALL data will be even larger.</p> 649</td> 650</tr> 651</table> 652</div> 653 654<!-- endspecialdetailsdiv --> 655<div class="tablewrapcoords"><a id="fractionalatomiccoordinates1" name="fractionalatomiccoordinates1"/> <span class="heading3">Fractional atomic coordinates and isotropic or 656equivalent isotropic displacement parameters 657(�<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span> 658<!-- endtoplinkspan --> 659<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 660<tr> 661<td class="tabledata"/> 662<td class="tabledata"><i>x</i></td> 663<td class="tabledata"><i>y</i></td> 664<td class="tabledata"><i>z</i></td> 665<td class="tabledata"> 666<i>U</i><sub>iso</sub>*/<i>U</i><sub>eq</sub></td> 667<td class="tabledata"/> 668</tr> 669 670<tr> 671<td class="tabledata">I1</td> 672<td class="tabledata">0.219874 (11)</td> 673<td class="tabledata">0.02241 (3)</td> 674<td class="tabledata">0.328844 (8)</td> 675<td class="tabledata">0.01748 (5)</td> 676<td class="tabledata"/> 677</tr> 678 679<tr> 680<td class="tabledata">N1</td> 681<td class="tabledata">0.14038 (12)</td> 682<td class="tabledata">0.3597 (4)</td> 683<td class="tabledata">0.03053 (10)</td> 684<td class="tabledata">0.0158 (3)</td> 685<td class="tabledata"/> 686</tr> 687 688<tr> 689<td class="tabledata">C1</td> 690<td class="tabledata">0.29294 (15)</td> 691<td class="tabledata"><span style="font-family:Times">?</span>0.0875 (4)</td> 692<td class="tabledata">0.20654 (12)</td> 693<td class="tabledata">0.0146 (3)</td> 694<td class="tabledata"/> 695</tr> 696 697<tr> 698<td class="tabledata">C2</td> 699<td class="tabledata">0.37697 (15)</td> 700<td class="tabledata"><span style="font-family:Times">?</span>0.2923 (4)</td> 701<td class="tabledata">0.21484 (12)</td> 702<td class="tabledata">0.0167 (3)</td> 703<td class="tabledata"/> 704</tr> 705 706<tr> 707<td class="tabledata">C3</td> 708<td class="tabledata">0.43327 (16)</td> 709<td class="tabledata"><span style="font-family:Times">?</span>0.3648 (5)</td> 710<td class="tabledata">0.13879 (12)</td> 711<td class="tabledata">0.0178 (3)</td> 712<td class="tabledata"/> 713</tr> 714 715<tr> 716<td class="tabledata">C4</td> 717<td class="tabledata">0.40419 (16)</td> 718<td class="tabledata"><span style="font-family:Times">?</span>0.2345 (5)</td> 719<td class="tabledata">0.05442 (13)</td> 720<td class="tabledata">0.0185 (4)</td> 721<td class="tabledata"/> 722</tr> 723 724<tr> 725<td class="tabledata">C5</td> 726<td class="tabledata">0.32010 (17)</td> 727<td class="tabledata"><span style="font-family:Times">?</span>0.0341 (4)</td> 728<td class="tabledata">0.04599 (13)</td> 729<td class="tabledata">0.0160 (3)</td> 730<td class="tabledata"/> 731</tr> 732 733<tr> 734<td class="tabledata">H5</td> 735<td class="tabledata">0.2813</td> 736<td class="tabledata"><span style="font-family:Times">?</span>0.0060</td> 737<td class="tabledata"><span style="font-family:Times">?</span>0.0162</td> 738<td class="tabledata">0.019*</td> 739<td class="tabledata"/> 740</tr> 741 742<tr> 743<td class="tabledata">C6</td> 744<td class="tabledata">0.26222 (16)</td> 745<td class="tabledata">0.0456 (4)</td> 746<td class="tabledata">0.12178 (13)</td> 747<td class="tabledata">0.0135 (3)</td> 748<td class="tabledata"/> 749</tr> 750 751<tr> 752<td class="tabledata">C7</td> 753<td class="tabledata">0.17398 (15)</td> 754<td class="tabledata">0.2630 (4)</td> 755<td class="tabledata">0.10940 (12)</td> 756<td class="tabledata">0.0147 (3)</td> 757<td class="tabledata"/> 758</tr> 759 760<tr> 761<td class="tabledata">C8</td> 762<td class="tabledata">0.05021 (16)</td> 763<td class="tabledata">0.5681 (4)</td> 764<td class="tabledata">0.02623 (13)</td> 765<td class="tabledata">0.0160 (3)</td> 766<td class="tabledata"/> 767</tr> 768 769<tr> 770<td class="tabledata">H8B</td> 771<td class="tabledata">0.0723 (18)</td> 772<td class="tabledata">0.725 (5)</td> 773<td class="tabledata"><span style="font-family:Times">?</span>0.0044 (15)</td> 774<td class="tabledata">0.016 (6)*</td> 775<td class="tabledata"/> 776</tr> 777 778<tr> 779<td class="tabledata">H4</td> 780<td class="tabledata">0.4465 (18)</td> 781<td class="tabledata"><span style="font-family:Times">?</span>0.278 (5)</td> 782<td class="tabledata">0.0004 (15)</td> 783<td class="tabledata">0.017 (6)*</td> 784<td class="tabledata"/> 785</tr> 786 787<tr> 788<td class="tabledata">H8A</td> 789<td class="tabledata">0.0293 (19)</td> 790<td class="tabledata">0.629 (6)</td> 791<td class="tabledata">0.0866 (16)</td> 792<td class="tabledata">0.021 (6)*</td> 793<td class="tabledata"/> 794</tr> 795 796<tr> 797<td class="tabledata">H2</td> 798<td class="tabledata">0.3998 (18)</td> 799<td class="tabledata"><span style="font-family:Times">?</span>0.387 (6)</td> 800<td class="tabledata">0.2766 (16)</td> 801<td class="tabledata">0.015 (6)*</td> 802<td class="tabledata"/> 803</tr> 804 805<tr> 806<td class="tabledata">H7</td> 807<td class="tabledata">0.144 (2)</td> 808<td class="tabledata">0.323 (7)</td> 809<td class="tabledata">0.1634 (18)</td> 810<td class="tabledata">0.034 (7)*</td> 811<td class="tabledata"/> 812</tr> 813 814<tr> 815<td class="tabledata">H3</td> 816<td class="tabledata">0.488 (3)</td> 817<td class="tabledata"><span style="font-family:Times">?</span>0.507 (5)</td> 818<td class="tabledata">0.148 (2)</td> 819<td class="tabledata">0.031 (9)*</td> 820<td class="tabledata"/> 821</tr> 822</table> 823</div> 824 825<!-- endtablewrapcoordsdiv --> 826<div class="tablewrapadps"><a id="atomicdisplacement1" name="atomicdisplacement1"/> <span class="heading3">Atomic 827displacement parameters (�<sup>2</sup>)</span> 828<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 829<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 830<tr> 831<td class="tabledata"/> 832<td class="tabledata"><i>U</i><sup>11</sup></td> 833<td class="tabledata"><i>U</i><sup>22</sup></td> 834<td class="tabledata"><i>U</i><sup>33</sup></td> 835<td class="tabledata"><i>U</i><sup>12</sup></td> 836<td class="tabledata"><i>U</i><sup>13</sup></td> 837<td class="tabledata"><i>U</i><sup>23</sup></td> 838</tr> 839 840<tr> 841<td class="tabledata">I1</td> 842<td class="tabledata">0.02070 (7)</td> 843<td class="tabledata">0.01995 (7)</td> 844<td class="tabledata">0.01214 (6)</td> 845<td class="tabledata">0.00044 (4)</td> 846<td class="tabledata">0.00353 (4)</td> 847<td class="tabledata">0.00024 (4)</td> 848</tr> 849 850<tr> 851<td class="tabledata">N1</td> 852<td class="tabledata">0.0157 (7)</td> 853<td class="tabledata">0.0154 (8)</td> 854<td class="tabledata">0.0163 (6)</td> 855<td class="tabledata">0.0034 (6)</td> 856<td class="tabledata">0.0008 (5)</td> 857<td class="tabledata">0.0003 (5)</td> 858</tr> 859 860<tr> 861<td class="tabledata">C1</td> 862<td class="tabledata">0.0162 (8)</td> 863<td class="tabledata">0.0149 (8)</td> 864<td class="tabledata">0.0127 (7)</td> 865<td class="tabledata"><span style="font-family:Times">?</span>0.0002 (6)</td> 866<td class="tabledata">0.0015 (6)</td> 867<td class="tabledata"><span style="font-family:Times">?</span>0.0012 (6)</td> 868</tr> 869 870<tr> 871<td class="tabledata">C2</td> 872<td class="tabledata">0.0184 (8)</td> 873<td class="tabledata">0.0151 (8)</td> 874<td class="tabledata">0.0160 (7)</td> 875<td class="tabledata">0.0003 (7)</td> 876<td class="tabledata"><span style="font-family:Times">?</span>0.0026 (6)</td> 877<td class="tabledata">0.0001 (6)</td> 878</tr> 879 880<tr> 881<td class="tabledata">C3</td> 882<td class="tabledata">0.0155 (8)</td> 883<td class="tabledata">0.0175 (9)</td> 884<td class="tabledata">0.0201 (8)</td> 885<td class="tabledata">0.0046 (7)</td> 886<td class="tabledata"><span style="font-family:Times">?</span>0.0003 (6)</td> 887<td class="tabledata"><span style="font-family:Times">?</span>0.0004 (7)</td> 888</tr> 889 890<tr> 891<td class="tabledata">C4</td> 892<td class="tabledata">0.0192 (8)</td> 893<td class="tabledata">0.0187 (9)</td> 894<td class="tabledata">0.0178 (8)</td> 895<td class="tabledata">0.0049 (7)</td> 896<td class="tabledata">0.0033 (6)</td> 897<td class="tabledata"><span style="font-family:Times">?</span>0.0019 (6)</td> 898</tr> 899 900<tr> 901<td class="tabledata">C5</td> 902<td class="tabledata">0.0188 (8)</td> 903<td class="tabledata">0.0161 (8)</td> 904<td class="tabledata">0.0132 (7)</td> 905<td class="tabledata">0.0018 (6)</td> 906<td class="tabledata">0.0028 (6)</td> 907<td class="tabledata"><span style="font-family:Times">?</span>0.0030 (6)</td> 908</tr> 909 910<tr> 911<td class="tabledata">C6</td> 912<td class="tabledata">0.0151 (8)</td> 913<td class="tabledata">0.0132 (8)</td> 914<td class="tabledata">0.0123 (7)</td> 915<td class="tabledata">0.0001 (6)</td> 916<td class="tabledata">0.0011 (6)</td> 917<td class="tabledata"><span style="font-family:Times">?</span>0.0011 (6)</td> 918</tr> 919 920<tr> 921<td class="tabledata">C7</td> 922<td class="tabledata">0.0147 (7)</td> 923<td class="tabledata">0.0129 (8)</td> 924<td class="tabledata">0.0168 (7)</td> 925<td class="tabledata">0.0008 (6)</td> 926<td class="tabledata">0.0021 (6)</td> 927<td class="tabledata"><span style="font-family:Times">?</span>0.0011 (6)</td> 928</tr> 929 930<tr> 931<td class="tabledata">C8</td> 932<td class="tabledata">0.0151 (8)</td> 933<td class="tabledata">0.0149 (8)</td> 934<td class="tabledata">0.0178 (8)</td> 935<td class="tabledata">0.0038 (6)</td> 936<td class="tabledata">0.0009 (6)</td> 937<td class="tabledata">0.0002 (6)</td> 938</tr> 939</table> 940</div> 941 942<!-- endtablewrapadpsdiv --> 943<div class="tablewrapgeomlong"><a id="geometricparameters1" name="geometricparameters1"/> <span class="heading3">Geometric 944parameters (�, �)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span> 945<!-- endtoplinkspan --><!-- startgeom --> 946<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 947<colgroup span="4"> 948<col width="30%"/> 949<col width="20%"/> 950<col width="30%"/> 951<col width="20%"/></colgroup> 952 953<tr> 954<td width="30%" class="tabledata">I1-C1</td> 955<td width="20%" class="tabledata">2.1133�(17)</td> 956<td width="30%" class="tabledata">C4-C5</td> 957<td width="20%" class="tabledata">1.376�(3)</td> 958</tr> 959 960<tr> 961<td width="30%" class="tabledata">N1-C7</td> 962<td width="20%" class="tabledata">1.270�(2)</td> 963<td width="30%" class="tabledata">C4-H4</td> 964<td width="20%" class="tabledata">0.99�(2)</td> 965</tr> 966 967<tr> 968<td width="30%" class="tabledata">N1-C8</td> 969<td width="20%" class="tabledata">1.455�(2)</td> 970<td width="30%" class="tabledata">C5-C6</td> 971<td width="20%" class="tabledata">1.404�(3)</td> 972</tr> 973 974<tr> 975<td width="30%" class="tabledata">C1-C2</td> 976<td width="20%" class="tabledata">1.389�(3)</td> 977<td width="30%" class="tabledata">C5-H5</td> 978<td width="20%" class="tabledata">0.9975</td> 979</tr> 980 981<tr> 982<td width="30%" class="tabledata">C1-C6</td> 983<td width="20%" class="tabledata">1.403�(3)</td> 984<td width="30%" class="tabledata">C6-C7</td> 985<td width="20%" class="tabledata">1.469�(3)</td> 986</tr> 987 988<tr> 989<td width="30%" class="tabledata">C2-C3</td> 990<td width="20%" class="tabledata">1.388�(3)</td> 991<td width="30%" class="tabledata">C7-H7</td> 992<td width="20%" class="tabledata">0.93�(3)</td> 993</tr> 994 995<tr> 996<td width="30%" class="tabledata">C2-H2</td> 997<td width="20%" class="tabledata">1.02�(2)</td> 998<td width="30%" class="tabledata">C8-C8<sup>i</sup></td> 999<td width="20%" class="tabledata">1.526�(4)</td> 1000</tr> 1001 1002<tr> 1003<td width="30%" class="tabledata">C3-C4</td> 1004<td width="20%" class="tabledata">1.388�(3)</td> 1005<td width="30%" class="tabledata">C8-H8B</td> 1006<td width="20%" class="tabledata">0.90�(2)</td> 1007</tr> 1008 1009<tr> 1010<td width="30%" class="tabledata">C3-H3</td> 1011<td width="20%" class="tabledata">0.94�(3)</td> 1012<td width="30%" class="tabledata">C8-H8A</td> 1013<td width="20%" class="tabledata">0.98�(2)</td> 1014</tr> 1015 1016<tr> 1017<td width="25%" class="tabledata"/> 1018<td width="25%" class="tabledata"/> 1019<td width="25%" class="tabledata"/> 1020<td width="25%" class="tabledata"/> 1021</tr> 1022 1023<tr> 1024<td width="30%" class="tabledata">C7-N1-C8</td> 1025<td width="20%" class="tabledata">117.33�(16)</td> 1026<td width="30%" class="tabledata">C4-C5-H5</td> 1027<td width="20%" class="tabledata">117.7</td> 1028</tr> 1029 1030<tr> 1031<td width="30%" class="tabledata">C2-C1-C6</td> 1032<td width="20%" class="tabledata">121.13�(17)</td> 1033<td width="30%" class="tabledata">C6-C5-H5</td> 1034<td width="20%" class="tabledata">116.7</td> 1035</tr> 1036 1037<tr> 1038<td width="30%" class="tabledata">C2-C1-I1</td> 1039<td width="20%" class="tabledata">116.36�(13)</td> 1040<td width="30%" class="tabledata">C1-C6-C5</td> 1041<td width="20%" class="tabledata">117.54�(18)</td> 1042</tr> 1043 1044<tr> 1045<td width="30%" class="tabledata">C6-C1-I1</td> 1046<td width="20%" class="tabledata">122.46�(14)</td> 1047<td width="30%" class="tabledata">C1-C6-C7</td> 1048<td width="20%" class="tabledata">123.23�(17)</td> 1049</tr> 1050 1051<tr> 1052<td width="30%" class="tabledata">C3-C2-C1</td> 1053<td width="20%" class="tabledata">119.97�(17)</td> 1054<td width="30%" class="tabledata">C5-C6-C7</td> 1055<td width="20%" class="tabledata">119.23�(17)</td> 1056</tr> 1057 1058<tr> 1059<td width="30%" class="tabledata">C3-C2-H2</td> 1060<td width="20%" class="tabledata">118.9�(13)</td> 1061<td width="30%" class="tabledata">N1-C7-C6</td> 1062<td width="20%" class="tabledata">122.09�(17)</td> 1063</tr> 1064 1065<tr> 1066<td width="30%" class="tabledata">C1-C2-H2</td> 1067<td width="20%" class="tabledata">121.1�(13)</td> 1068<td width="30%" class="tabledata">N1-C7-H7</td> 1069<td width="20%" class="tabledata">122.8�(17)</td> 1070</tr> 1071 1072<tr> 1073<td width="30%" class="tabledata">C2-C3-C4</td> 1074<td width="20%" class="tabledata">119.67�(18)</td> 1075<td width="30%" class="tabledata">C6-C7-H7</td> 1076<td width="20%" class="tabledata">115.1�(17)</td> 1077</tr> 1078 1079<tr> 1080<td width="30%" class="tabledata">C2-C3-H3</td> 1081<td width="20%" class="tabledata">116�(2)</td> 1082<td width="30%" class="tabledata">N1-C8-C8<sup>i</sup></td> 1083<td width="20%" class="tabledata">108.9�(2)</td> 1084</tr> 1085 1086<tr> 1087<td width="30%" class="tabledata">C4-C3-H3</td> 1088<td width="20%" class="tabledata">124�(2)</td> 1089<td width="30%" class="tabledata">N1-C8-H8B</td> 1090<td width="20%" class="tabledata">107.1�(14)</td> 1091</tr> 1092 1093<tr> 1094<td width="30%" class="tabledata">C5-C4-C3</td> 1095<td width="20%" class="tabledata">120.34�(18)</td> 1096<td width="30%" class="tabledata">C8<sup>i</sup>-C8-H8B</td> 1097<td width="20%" class="tabledata">109.9�(14)</td> 1098</tr> 1099 1100<tr> 1101<td width="30%" class="tabledata">C5-C4-H4</td> 1102<td width="20%" class="tabledata">119.5�(13)</td> 1103<td width="30%" class="tabledata">N1-C8-H8A</td> 1104<td width="20%" class="tabledata">113.6�(15)</td> 1105</tr> 1106 1107<tr> 1108<td width="30%" class="tabledata">C3-C4-H4</td> 1109<td width="20%" class="tabledata">120.1�(13)</td> 1110<td width="30%" class="tabledata">C8<sup>i</sup>-C8-H8A</td> 1111<td width="20%" class="tabledata">108.3�(14)</td> 1112</tr> 1113 1114<tr> 1115<td width="30%" class="tabledata">C4-C5-C6</td> 1116<td width="20%" class="tabledata">121.35�(18)</td> 1117<td width="30%" class="tabledata">H8B-C8-H8A</td> 1118<td width="20%" class="tabledata">109�(2)</td> 1119</tr> 1120 1121<tr> 1122<td width="25%" class="tabledata"/> 1123<td width="25%" class="tabledata"/> 1124<td width="25%" class="tabledata"/> 1125<td width="25%" class="tabledata"/> 1126</tr> 1127 1128<tr> 1129<td width="30%" class="tabledata">C6-C1-C2-C3</td> 1130<td width="20%" class="tabledata">1.1�(3)</td> 1131<td width="30%" class="tabledata">I1-C1-C6-C7</td> 1132<td width="20%" class="tabledata"><span style="font-family:Times">?</span>2.6�(3)</td> 1133</tr> 1134 1135<tr> 1136<td width="30%" class="tabledata">I1-C1-C2-C3</td> 1137<td width="20%" class="tabledata"><span style="font-family:Times">?</span>176.50�(15)</td> 1138<td width="30%" class="tabledata">C4-C5-C6-C1</td> 1139<td width="20%" class="tabledata"><span style="font-family:Times">?</span>0.2�(3)</td> 1140</tr> 1141 1142<tr> 1143<td width="30%" class="tabledata">C1-C2-C3-C4</td> 1144<td width="20%" class="tabledata"><span style="font-family:Times">?</span>0.9�(3)</td> 1145<td width="30%" class="tabledata">C4-C5-C6-C7</td> 1146<td width="20%" class="tabledata">179.31�(18)</td> 1147</tr> 1148 1149<tr> 1150<td width="30%" class="tabledata">C2-C3-C4-C5</td> 1151<td width="20%" class="tabledata">0.1�(3)</td> 1152<td width="30%" class="tabledata">C8-N1-C7-C6</td> 1153<td width="20%" class="tabledata">178.18�(17)</td> 1154</tr> 1155 1156<tr> 1157<td width="30%" class="tabledata">C3-C4-C5-C6</td> 1158<td width="20%" class="tabledata">0.5�(3)</td> 1159<td width="30%" class="tabledata">C1-C6-C7-N1</td> 1160<td width="20%" class="tabledata"><span style="font-family:Times">?</span>173.04�(19)</td> 1161</tr> 1162 1163<tr> 1164<td width="30%" class="tabledata">C2-C1-C6-C5</td> 1165<td width="20%" class="tabledata"><span style="font-family:Times">?</span>0.5�(3)</td> 1166<td width="30%" class="tabledata">C5-C6-C7-N1</td> 1167<td width="20%" class="tabledata">7.4�(3)</td> 1168</tr> 1169 1170<tr> 1171<td width="30%" class="tabledata">I1-C1-C6-C5</td> 1172<td width="20%" class="tabledata">176.90�(13)</td> 1173<td width="30%" class="tabledata">C7-N1-C8-C8<sup>i</sup></td> 1174<td width="20%" class="tabledata"><span style="font-family:Times">?</span>114.6�(2)</td> 1175</tr> 1176 1177<tr> 1178<td width="30%" class="tabledata">C2-C1-C6-C7</td> 1179<td width="20%" class="tabledata">179.94�(17)</td> 1180<td width="30%" class="tabledata"/> 1181<td width="20%" class="tabledata"/> 1182</tr> 1183</table> 1184 1185<table style="table-layout:fixed" width="100%" class="noborder"> 1186<tr> 1187<td class="tabledata">Symmetry codes: (i) ?<i>x</i>, 1188?<i>y</i>+1, ?<i>z</i>.</td> 1189</tr> 1190</table> 1191</div> 1192 1193<!-- endtablewrapgeomlongdiv --> 1194<div class="tablewraphbondslong"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3">Hydrogen-bond geometry (�, �)</span> 1195<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1196<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 1197<colgroup span="5"> 1198<col width="40%"/> 1199<col width="15%"/> 1200<col width="15%"/> 1201<col width="15%"/> 1202<col width="15%"/></colgroup> 1203 1204<tr> 1205<td width="40%" class="tabledata"> 1206<i>D</i>-H���<i>A</i></td> 1207<td width="15%" class="tabledata"><i>D</i>-H</td> 1208<td width="15%" class="tabledata">H���<i>A</i></td> 1209<td width="15%" class="tabledata"> 1210<i>D</i>���<i>A</i></td> 1211<td width="15%" class="tabledata"> 1212<i>D</i>-H���<i>A</i></td> 1213</tr> 1214 1215<tr> 1216<td width="40%" class="tabledata">C7-H7���I1</td> 1217<td width="15%" class="tabledata">0.93�(3)</td> 1218<td width="15%" class="tabledata">2.87�(3)</td> 1219<td width="15%" class="tabledata">3.3880�(18)</td> 1220<td width="15%" class="tabledata">116�(2)</td> 1221</tr> 1222</table> 1223</div> 1224 1225<!-- endtablewraphbondslongdiv --><!-- endcoord --><!-- endadp --> 1226<!-- startgeom --><!-- endgeom --> 1227<div class="tablewraphbondsshort"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3"><span class="tablenum"><b>Table 1</b></span><br/> 1228Hydrogen-bond geometry (�, �)</span> 1229<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1230<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 1231<colgroup span="5"> 1232<col width="40%"/> 1233<col width="15%"/> 1234<col width="15%"/> 1235<col width="15%"/> 1236<col width="15%"/></colgroup> 1237 1238<tr> 1239<td width="40%" class="tabledata"> 1240<i>D</i>-H���<i>A</i></td> 1241<td width="15%" class="tabledata"><i>D</i>-H</td> 1242<td width="15%" class="tabledata">H���<i>A</i></td> 1243<td width="15%" class="tabledata"> 1244<i>D</i>���<i>A</i></td> 1245<td width="15%" class="tabledata"> 1246<i>D</i>-H���<i>A</i></td> 1247</tr> 1248 1249<tr> 1250<td width="40%" class="tabledata">C7-H7���I1</td> 1251<td width="15%" class="tabledata">0.93�(3)</td> 1252<td width="15%" class="tabledata">2.87�(3)</td> 1253<td width="15%" class="tabledata">3.3880�(18)</td> 1254<td width="15%" class="tabledata">116�(2)</td> 1255</tr> 1256</table> 1257</div> 1258 1259<!-- endtablewraphbondsshortdiv --> 1260</div> 1261 1262<!-- enddatablockdiv --><a id="extratables" name="extratables"/> 1263 1264 1265<div class="acknowledgements"><a id="acknowledgements" name="acknowledgements"/> 1266 1267<div class="heading2">Acknowledgements <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1268</div> 1269 1270<!-- endheading2div --> 1271<p>HKF and RK thank the Malaysian Government and Universiti Sains 1272Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK 1273thanks Universiti Sains Malaysia for a post-doctoral research 1274fellowship.</p> 1275</div> 1276 1277<!-- endacknowledgementsdiv --> 1278<div class="references"><a id="references" name="references"/><a class="buttons" title="link to reference list" href="./at2623bdy.html#References">references</a></div> 1279 1280<!-- endreferencesdiv --> 1281<div class="publreferences"><a id="publreferences" name="publreferences"/> 1282 1283<div class="heading2">References <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1284</div> 1285 1286<!-- endheading2div --> 1287<p>Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. 1288G. & Taylor, R. (1987). <i>J. Chem. Soc. Perkin Trans. 2</i>, 1289pp. S1-S19.<br/> 1290<br/> 1291Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). 1292<i>Angew. Chem. Int. Ed. Engl.</i> <b>34</b>, 1555-1573.<br/> 1293<br/> 1294Brammer, L., Bruton, E. A. & Sherwood, P. (2001). <i>Cryst. 1295Growth Des.</i> <b>1</b>, 277-290.<br/> 1296<br/> 1297Bruker (2005). <i>APEX2</i>, <i>SAINT</i> and <i>SADABS</i>. Bruker 1298AXS Inc., Madison, Wisconsin, USA.<br/> 1299<br/> 1300Calligaris, M. & Randaccio, L. (1987). <i>Comprehensive 1301Coordination Chemistry</i>, Vol. 2, edited by G. Wilkinson, pp. 1302715-738. London: Pergamon.<br/> 1303<br/> 1304Fun, H.-K., Kargar, H. & Kia, R. (2008). <i>Acta Cryst.</i> 1305E<b>64</b>, o1308.<br/> 1306<br/> 1307Fun, H.-K., Kia, R. & Kargar, H. (2008). <i>Acta Cryst.</i> 1308E<b>64</b>, o1335.<br/> 1309<br/> 1310Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008). 1311<i>Acta Cryst.</i> E<b>64</b>, o1471.<br/> 1312<br/> 1313Hou, B., Friedman, N., Ruhman, S., Sheves, M. & Ottolenghi, M. 1314(2001). <i>J. Phys. Chem. B</i>, <b>105</b>, 7042-7048.<br/> 1315<br/> 1316Lommerse, J. P. M., Stone, A. J., Taylor, R. & Allen, F. H. 1317(1996). <i>J. Am. Chem. Soc.</i> <b>118</b>, 3108-3116.<br/> 1318<br/> 1319Pal, S., Barik, A. K., Gupta, S., Hazra, A., Kar, S. K., Peng, 1320S.-M., Lee, G.-H., Butcher, R. J., El Fallah, M. S. & Ribas, J. 1321(2005). <i>Inorg. Chem.</i> <b>44</b>, 3880-3889.<br/> 1322<br/> 1323Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., 1324McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). 1325<i>J. Med. Chem.</i> <b>45</b>, 410-419.<br/> 1326<br/> 1327Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>, 1328112-122.<br/> 1329<br/> 1330Spek, A. L. (2003). <i>J. Appl. Cryst.</i> <b>36</b>, 7-13.<br/> 1331<br/> 1332</p> 1333</div> 1334 1335<!-- endpublreferencesdiv --> 1336<br/> 1337<br/> 1338<br/> 1339<br/> 1340<br/> 1341<br/> 1342<br/> 1343<br/> 1344<br/> 1345<br/> 1346<br/> 1347<br/> 1348<br/> 1349<br/> 1350<br/> 1351<br/> 1352<br/> 1353<br/> 1354<br/> 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</body> 1382</html>