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E<b>65</b>, 49o592����[ <a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536809006060">doi:10.1107/S1600536809006060</a> 50]</p> 51</div> 52 53<h3>Pyrrolidinium chloride</h3> 54 55<h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Giglmeier,%20H."> 56H. Giglmeier</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Kerscher,%20T."> 57T. Kerscher</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Kl%26uuml;fers,%20P."> 58P. Kl�fers</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Mayer,%20P."> 59P. Mayer</a></h3> 60 61<div class="abstract"><a id="abstract" name="abstract"/> 62 63<div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 64</div> 65 66<!-- endheading2div --> 67<p>The title compound, C<span class="inf"><sub>4</sub></span>H<span class="inf"><sub>10</sub></span>N<span class="sup"><sup>+</sup></span>�Cl<span class="sup"><sup>-</sup></span>, was obtained as a decomposition 68product from 2,6-bis(pyrrolidinyl)pyridine. The anion lies on the 69same cristallographic mirror plane as the N atom of the cation, the 70complete cation being generated by mirror symmetry. The anions and 71cations are connected by N<span class="sup"><sup>+</sup></span>-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif"/>Cl<span class="sup"><sup>-</sup></span> hydrogen bonds into chains along 72[100]. The pyrrolidinium cation is puckered in an envelope 73conformation <span class="it"><i>E</i></span><span class="inf"><sub>N1</sub></span>.</p> 74</div> 75 76<!-- endabstractdiv --> 77<div class="contentslist"> 78<ul> 79<li class="comment"><a title="Comment" href="#comment">Comment</a></li> 80 81<li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li> 82 83<li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li> 84 85<li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li> 86 87<li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li> 88 89<li class="figures"><a title="Figures" href="#figures">Figures</a></li> 90 91<li><a title="(I)" href="#chemicalname1">Pyrrolidinium chloride</a> 92 93 94<ul> 95<li><a title="Crystal data" href="#crystaldata1">Crystal 96data</a></li> 97 98<li><a title="Data collection" href="#datacollection1">Data 99collection</a></li> 100 101<li><a title="Refinement data" href="#refinementdata1">Refinement 102data</a></li> 103 104<li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li> 105 106<li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic 107coordinates</a></li> 108 109<li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li> 110 111<li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li> 112 113<li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 114 115<li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li> 116</ul> 117</li> 118 119<li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li> 120 121<li class="publreferences"><a title="References" href="#publreferences">References</a></li> 122</ul> 123</div> 124 125<!-- endcontentslistdiv --> 126<div class="comment"><a id="comment" name="comment"/> 127 128<div class="heading2">Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 129</div> 130 131<!-- endheading2div --> 132<p>The title compound was obtained as a decomposition product. The 133organic salt is composed of the pyrrolidinium cation and a chloride 134anion (Fig. 1). The crystal packing is shown in Fig. 2. In the 135crystal, both H atoms bonded to N1 of the pyrrolidinium cation are 136involved in hydrogen bonds with chloride as acceptor. Both can be 137described according to graph set analysis with a 138D<sup>1</sup><sub>1</sub>(2) descriptor on the unitary level. This 139bonding pattern leads to chains along [1 0 0] which, starting from 140chloride, can be described according to graph set analysis with a 141C<sup>2</sup><sub>1</sub>(4) descriptor on the binary level. The 142hydrogen bonding pattern is shown in Fig. 3.</p> 143 144<p>The <i>C<sub>s</sub></i> symmetric five-membered pyrrolidinium 145ring can be described according to Cremer & Pople (1975) by the 146puckering parameters q<sub>2</sub> = 0.3061 � and <span style="font-family:Times">?</span><sub>2</sub> = 180.0000. The 147closest pucker descriptor is an envelope <i>E</i><sub>N1</sub>.</p> 148</div> 149 150<!-- endcommentdiv --> 151<div class="relatedliterature"><a id="relatedliterature" name="relatedliterature"/> 152 153<div class="heading2">Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 154</div> 155 156<!-- endheading2div --> 157<p>For details of the synthesis of 2,6-bis(pyrrolidinyl)pyridine, 158see: Folmer-Anderson <i>et al.</i> (2005). For related structures 159containing the pyrrolidinium cation, see: Kashino <i>et al.</i> 160(1978); Moritani <i>et al.</i> (1987); Jakubas <i>et al.</i> 161(2005). For a description of the <i>E</i><sub>N1</sub> conformation 162of the five-membered ring, see: Cremer & Pople (1975).</p> 163</div> 164 165<!-- endrelatedliteraturediv --> 166<div class="experimental"><a id="experimental" name="experimental"/> 167 168<div class="heading2">Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 169</div> 170 171<!-- endheading2div --> 172<p>The title compound was obtained as decomposition product of 1732,6-bis(pyrrolidinyl)pyridine, which was synthesized according to 174Folmer-Anderson <i>et al.</i> (2005), after 4 months at room 175temperature.</p> 176</div> 177 178<!-- endexperimentaldiv --> 179<div class="refinement"><a id="refinement" name="refinement"/> 180 181<div class="heading2">Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 182</div> 183 184<!-- endheading2div --> 185<p>H atoms were placed in calculated positions (C-H = 0.99 �, 186N-H = 0.92 �) and were included in the refinement in the 187riding model approximation with <i>U</i><sub>iso</sub>(H) = 1.2 188<i>U</i><sub>eq</sub>(C/N).</p> 189</div> 190 191<!-- endrefinementdiv --> 192<div class="computingdetails"><a id="computingdetails" name="computingdetails"/> 193 194<div class="heading2">Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 195</div> 196 197<!-- endheading2div --> 198<p>Data collection: <i>COLLECT</i> (Nonius, 2004); cell refinement: 199<i>SCALEPACK</i> (Otwinowski & Minor, 1997); data reduction: 200<i>DENZO</i> and <i>SCALEPACK</i> (Otwinowski & Minor, 1997); 201program(s) used to solve structure: <i>SHELXS97</i> (Sheldrick, 2022008); program(s) used to refine structure: <i>SHELXL97</i> 203(Sheldrick, 2008); molecular graphics: <i>ORTEP-3</i> (Farrugia, 2041997); software used to prepare material for publication: 205<i>SHELXL97</i> (Sheldrick, 2008).</p> 206</div> 207 208<!-- endcomputingdetailsdiv --> 209<div class="schemes"><a href="./bi2348scheme1.gif"/></div> 210 211<!-- endschemesdiv --> 212<div class="figures"><a id="figures" name="figures"/> 213 214<div class="heading2">Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 215</div> 216 217<!-- endheading2div --> 218<table style="table-layout:fixed" width="100%" class="nodecs"> 219<colgroup span="2"> 220<col width="110"/> 221<col/></colgroup> 222 223<tr> 224<td class="nodecs" align="center" width="110"><a href="./bi2348fig1.html"><img width="100" src="./bi2348fig1thm.gif" alt="[Figure 1]" align="middle"/></a> </td> 225<td class="nodecs" valign="middle">Fig. 1. The molecular structure 226of the <i>C<sub>s</sub></i> symmetric title compound with 227anisotropic displacement ellipsoids drawn at 50% probability for 228non-H atoms. Symmetry code: (i) <i>x</i>, -<i>y</i> + 1/2, 229<i>z</i>. </td> 230</tr> 231 232<tr> 233<td class="nodecs" align="center" width="110"><a href="./bi2348fig2.html"><img width="100" src="./bi2348fig2thm.gif" alt="[Figure 2]" align="middle"/></a> </td> 234<td class="nodecs" valign="middle">Fig. 2. Packing of the title 235compound, viewed along [0 1 0]. </td> 236</tr> 237 238<tr> 239<td class="nodecs" align="center" width="110"><a href="./bi2348fig3.html"><img width="100" src="./bi2348fig3thm.gif" alt="[Figure 3]" align="middle"/></a> </td> 240<td class="nodecs" valign="middle">Fig. 3. N-H���Cl 241hydrogen bonds lead to chain-like structures in the crystal 242structure along [1 0 0], shown here normal to [0 1 0]. Symmetry 243codes: (i) <i>x</i> + 1/2, -<i>y</i> + 1/2, -<i>z</i> + 1/2; (ii) 244<i>x</i> - 1/2, -<i>y</i> + 1/2, -<i>z</i> + 1/2; (iii) <i>x</i> - 2451, <i>y</i>, <i>z</i>. </td> 246</tr> 247</table> 248</div> 249 250<!-- endfiguresdiv --> 251<div class="datablock1"> 252<div class="heading2"><a id="chemicalname1" name="chemicalname1"/>Pyrrolidinium chloride <span class="toplink"><a class="buttons" href="#top">top</a></span> 253<!-- endtoplinkspan --> 254</div> 255 256<!-- endheading2div --> 257<div class="tablewrapcrystaldatalong"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span> 258<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 259<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 260<colgroup span="2"> 261<col width="50%"/> 262<col width="50%"/></colgroup> 263 264<tr> 265<td width="50%" class="tabledata"> 266C<sub>4</sub>H<sub>10</sub>N<sup>+</sup>�Cl<sup>-</sup></td> 267<td width="50%" class="tabledata"><i>F</i><sub>000</sub> = 232</td> 268</tr> 269 270<tr> 271<td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> = 272107.58</td> 273<td width="50%" class="tabledata"><i>D</i><sub>x</sub> = 1.146 Mg 274m<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 275</tr> 276 277<tr> 278<td width="50%" class="tabledata">Orthorhombic, 279<i>P</i><i>n</i><i>m</i><i>a</i></td> 280<td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span> radiation<br/> 281<span style="font-family:Times">?</span> = 0.71073 �</td> 282</tr> 283 284<tr> 285<td width="50%" class="tabledata">Hall symbol: -P 2ac 2n</td> 286<td width="50%" class="tabledata">Cell parameters from 2321 287reflections</td> 288</tr> 289 290<tr> 291<td width="50%" class="tabledata"><i>a</i> = 7.4429 (4) �</td> 292<td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 3.1-27.5�</td> 293</tr> 294 295<tr> 296<td width="50%" class="tabledata"><i>b</i> = 9.4104 (5) �</td> 297<td width="50%" class="tabledata">� = 0.48 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td> 298</tr> 299 300<tr> 301<td width="50%" class="tabledata"><i>c</i> = 8.9021 (4) �</td> 302<td width="50%" class="tabledata"><i>T</i> = 200 K</td> 303</tr> 304 305<tr> 306<td width="50%" class="tabledata"><i>V</i> = 623.51 (5) 307�<sup>3</sup></td> 308<td width="50%" class="tabledata">Block, colourless</td> 309</tr> 310 311<tr> 312<td width="50%" class="tabledata"><i>Z</i> = 4</td> 313<td width="50%" class="tabledata">0.22 � 0.13 � 0.12 314mm</td> 315</tr> 316</table> 317 318<!-- endtabledatatable --> 319</div> 320 321<!-- endtablewrapcrystaldatalongdiv --> 322<div class="tablewrapdatacollectionlong"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data 323collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 324<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 325<colgroup span="2"> 326<col width="50%"/> 327<col width="50%"/></colgroup> 328 329<tr> 330<td width="50%" class="tabledata">Nonius KappaCCD<br/> 331diffractometer</td> 332<td width="50%" class="tabledata">608 reflections with <i>I</i> 333> 2<span style="font-family:Times">?</span>(<i>I</i>)</td> 334</tr> 335 336<tr> 337<td width="50%" class="tabledata">Radiation source: rotating 338anode</td> 339<td width="50%" class="tabledata"><i>R</i><sub>int</sub> = 3400.037</td> 341</tr> 342 343<tr> 344<td width="50%" class="tabledata">Monochromator: MONTEL, graded 345multilayered X-ray optics</td> 346<td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>max</sub> = 34727.5�</td> 348</tr> 349 350<tr> 351<td width="50%" class="tabledata"><i>T</i> = 200 K</td> 352<td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>min</sub> = 3533.2�</td> 354</tr> 355 356<tr> 357<td width="50%" class="tabledata"><span style="font-family:Times">?</span> and <span style="font-family:Times">?</span> scans</td> 358<td width="50%" class="tabledata"><i>h</i> = <span style="font-family:Times">?</span>8?9</td> 359</tr> 360 361<tr> 362<td width="50%" class="tabledata">Absorption correction: none</td> 363<td width="50%" class="tabledata"><i>k</i> = <span style="font-family:Times">?</span>12?12</td> 364</tr> 365 366<tr> 367<td width="50%" class="tabledata">4239 measured reflections</td> 368<td width="50%" class="tabledata"><i>l</i> = <span style="font-family:Times">?</span>11?10</td> 369</tr> 370 371<tr> 372<td width="50%" class="tabledata">756 independent reflections</td> 373<td width="50%" class="tabledata"/> 374</tr> 375</table> 376 377<!-- endtabledatatable --> 378</div> 379 380<!-- endtablewrapdatacollectionlongdiv --> 381<div class="tablewraprefinementdatalong"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span> 382<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 383<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 384<colgroup span="2"> 385<col width="50%"/> 386<col width="50%"/></colgroup> 387 388<tr> 389<td width="50%" class="tabledata">Refinement on 390<i>F</i><sup>2</sup></td> 391<td width="50%" class="tabledata">Secondary atom site location: 392difference Fourier map</td> 393</tr> 394 395<tr> 396<td width="50%" class="tabledata">Least-squares matrix: full</td> 397<td width="50%" class="tabledata">Hydrogen site location: inferred 398from neighbouring sites</td> 399</tr> 400 401<tr> 402<td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup> 403> 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] = 4040.040</td> 405<td width="50%" class="tabledata">H-atom parameters 406constrained</td> 407</tr> 408 409<tr> 410<td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) = 4110.120</td> 412<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> 4132</sup>) + (0.0625<i>P</i>)<sup>2</sup> + 0.1854<i>P</i>]<br/> 414where <i>P</i> = (<i>F</i><sub>o</sub><sup>2</sup> + 4152<i>F</i><sub>c</sub><sup>2</sup>)/3</td> 416</tr> 417 418<tr> 419<td width="50%" class="tabledata"><i>S</i> = 1.07</td> 420<td width="50%" class="tabledata">(?/<span style="font-family:Times">?</span>)<sub>max</sub> < 4210.001</td> 422</tr> 423 424<tr> 425<td width="50%" class="tabledata">756 reflections</td> 426<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 0.21 e 427�<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 428</tr> 429 430<tr> 431<td width="50%" class="tabledata">31 parameters</td> 432<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>0.23 e �<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 433</tr> 434 435<tr> 436<td width="50%" class="tabledata">Primary atom site location: 437structure-invariant direct methods</td> 438<td width="50%" class="tabledata">Extinction correction: none</td> 439</tr> 440</table> 441 442<!-- endtabledatatable --> 443</div> 444 445<!-- endtablewraprefinementdatalongdiv --> 446<div class="tablewrapcrystaldatashort"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span> 447<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 448<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 449<colgroup span="2"> 450<col width="50%"/> 451<col width="50%"/></colgroup> 452 453<tr> 454<td width="50%" class="tabledata"> 455C<sub>4</sub>H<sub>10</sub>N<sup>+</sup>�Cl<sup>-</sup></td> 456<td width="50%" class="tabledata"><i>V</i> = 623.51 (5) 457�<sup>3</sup></td> 458</tr> 459 460<tr> 461<td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> = 462107.58</td> 463<td width="50%" class="tabledata"><i>Z</i> = 4</td> 464</tr> 465 466<tr> 467<td width="50%" class="tabledata">Orthorhombic, 468<i>P</i><i>n</i><i>m</i><i>a</i></td> 469<td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span></td> 470</tr> 471 472<tr> 473<td width="50%" class="tabledata"><i>a</i> = 7.4429 (4) �</td> 474<td width="50%" class="tabledata">� = 0.48 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td> 475</tr> 476 477<tr> 478<td width="50%" class="tabledata"><i>b</i> = 9.4104 (5) �</td> 479<td width="50%" class="tabledata"><i>T</i> = 200 K</td> 480</tr> 481 482<tr> 483<td width="50%" class="tabledata"><i>c</i> = 8.9021 (4) �</td> 484<td width="50%" class="tabledata">0.22 � 0.13 � 0.12 485mm</td> 486</tr> 487</table> 488 489<!-- endtabledatatable --> 490</div> 491 492<!-- endtablewrapcrystaldatashortdiv --> 493<div class="tablewrapdatacollectionshort"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data 494collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 495<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 496<colgroup span="2"> 497<col width="50%"/> 498<col width="50%"/></colgroup> 499 500<tr> 501<td width="50%" class="tabledata">Nonius KappaCCD<br/> 502diffractometer</td> 503<td width="50%" class="tabledata">756 independent reflections</td> 504</tr> 505 506<tr> 507<td width="50%" class="tabledata">Absorption correction: none</td> 508<td width="50%" class="tabledata">608 reflections with <i>I</i> 509> 2<span style="font-family:Times">?</span>(<i>I</i>)</td> 510</tr> 511 512<tr> 513<td width="50%" class="tabledata">4239 measured reflections</td> 514<td width="50%" class="tabledata"><i>R</i><sub>int</sub> = 5150.037</td> 516</tr> 517</table> 518 519<!-- endtabledatatable --> 520</div> 521 522<!-- endtablewrapdatacollectionshortdiv --> 523<div class="tablewraprefinementdatashort"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span> 524<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 525<table style="table-layout:fixed" width="80%" summary="" class="tabledata"> 526<colgroup span="2"> 527<col width="50%"/> 528<col width="50%"/></colgroup> 529 530<tr> 531<td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup> 532> 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] = 5330.040</td> 534<td width="50%" class="tabledata">31 parameters</td> 535</tr> 536 537<tr> 538<td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) = 5390.120</td> 540<td width="50%" class="tabledata">H-atom parameters 541constrained</td> 542</tr> 543 544<tr> 545<td width="50%" class="tabledata"><i>S</i> = 1.07</td> 546<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 0.21 e 547�<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 548</tr> 549 550<tr> 551<td width="50%" class="tabledata">756 reflections</td> 552<td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>0.23 e �<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td> 553</tr> 554</table> 555 556<!-- endtabledatatable --> 557</div> 558 559<!-- endtablewraprefinementdatashortdiv --> 560<div class="specialdetails"><a id="specialdetails1" name="specialdetails1"/><span class="heading3">Special 561details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 562<table style="table-layout:fixed" width="100%" class="tabledata"> 563<tr> 564<td class="tabledata"> 565<p><b>Refinement</b>. Hydrogen atoms were placed in calculated 566positions (C-H 0.99 � for methylene C atoms and N-H 0.92 567� for N atoms) and were included in the refinement in the 568riding model approximation with U(H) set to 1.2 569<i>U</i><sub>eq</sub>(C) for C atoms and 1.2 570<i>U</i><sub>eq</sub>(N) for N atoms.</p> 571</td> 572</tr> 573</table> 574</div> 575 576<!-- endspecialdetailsdiv --> 577<div class="tablewrapcoords"><a id="fractionalatomiccoordinates1" name="fractionalatomiccoordinates1"/> <span class="heading3">Fractional atomic coordinates and isotropic or 578equivalent isotropic displacement parameters 579(�<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span> 580<!-- endtoplinkspan --> 581<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 582<tr> 583<td class="tabledata"/> 584<td class="tabledata"><i>x</i></td> 585<td class="tabledata"><i>y</i></td> 586<td class="tabledata"><i>z</i></td> 587<td class="tabledata"> 588<i>U</i><sub>iso</sub>*/<i>U</i><sub>eq</sub></td> 589<td class="tabledata"/> 590</tr> 591 592<tr> 593<td class="tabledata">N1</td> 594<td class="tabledata">0.2072 (3)</td> 595<td class="tabledata">0.2500</td> 596<td class="tabledata">0.3955 (3)</td> 597<td class="tabledata">0.0473 (6)</td> 598<td class="tabledata"/> 599</tr> 600 601<tr> 602<td class="tabledata">H101</td> 603<td class="tabledata">0.2341</td> 604<td class="tabledata">0.2500</td> 605<td class="tabledata">0.2946</td> 606<td class="tabledata">0.057*</td> 607<td class="tabledata"/> 608</tr> 609 610<tr> 611<td class="tabledata">H102</td> 612<td class="tabledata">0.0843</td> 613<td class="tabledata">0.2500</td> 614<td class="tabledata">0.4065</td> 615<td class="tabledata">0.057*</td> 616<td class="tabledata"/> 617</tr> 618 619<tr> 620<td class="tabledata">C1</td> 621<td class="tabledata">0.3204 (4)</td> 622<td class="tabledata">0.1712 (3)</td> 623<td class="tabledata">0.6283 (3)</td> 624<td class="tabledata">0.0781 (8)</td> 625<td class="tabledata"/> 626</tr> 627 628<tr> 629<td class="tabledata">H11</td> 630<td class="tabledata">0.2249</td> 631<td class="tabledata">0.1348</td> 632<td class="tabledata">0.6954</td> 633<td class="tabledata">0.094*</td> 634<td class="tabledata"/> 635</tr> 636 637<tr> 638<td class="tabledata">H12</td> 639<td class="tabledata">0.4376</td> 640<td class="tabledata">0.1348</td> 641<td class="tabledata">0.6641</td> 642<td class="tabledata">0.094*</td> 643<td class="tabledata"/> 644</tr> 645 646<tr> 647<td class="tabledata">C2</td> 648<td class="tabledata">0.2871 (3)</td> 649<td class="tabledata">0.1242 (2)</td> 650<td class="tabledata">0.4702 (3)</td> 651<td class="tabledata">0.0623 (6)</td> 652<td class="tabledata"/> 653</tr> 654 655<tr> 656<td class="tabledata">H21</td> 657<td class="tabledata">0.4009</td> 658<td class="tabledata">0.0963</td> 659<td class="tabledata">0.4208</td> 660<td class="tabledata">0.075*</td> 661<td class="tabledata"/> 662</tr> 663 664<tr> 665<td class="tabledata">H22</td> 666<td class="tabledata">0.2032</td> 667<td class="tabledata">0.0427</td> 668<td class="tabledata">0.4677</td> 669<td class="tabledata">0.075*</td> 670<td class="tabledata"/> 671</tr> 672 673<tr> 674<td class="tabledata">Cl1</td> 675<td class="tabledata">0.29515 (8)</td> 676<td class="tabledata">0.2500</td> 677<td class="tabledata">0.05610 (7)</td> 678<td class="tabledata">0.0488 (3)</td> 679<td class="tabledata"/> 680</tr> 681</table> 682</div> 683 684<!-- endtablewrapcoordsdiv --> 685<div class="tablewrapadps"><a id="atomicdisplacement1" name="atomicdisplacement1"/> <span class="heading3">Atomic 686displacement parameters (�<sup>2</sup>)</span> 687<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 688<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 689<tr> 690<td class="tabledata"/> 691<td class="tabledata"><i>U</i><sup>11</sup></td> 692<td class="tabledata"><i>U</i><sup>22</sup></td> 693<td class="tabledata"><i>U</i><sup>33</sup></td> 694<td class="tabledata"><i>U</i><sup>12</sup></td> 695<td class="tabledata"><i>U</i><sup>13</sup></td> 696<td class="tabledata"><i>U</i><sup>23</sup></td> 697</tr> 698 699<tr> 700<td class="tabledata">N1</td> 701<td class="tabledata">0.0466 (12)</td> 702<td class="tabledata">0.0500 (13)</td> 703<td class="tabledata">0.0452 (12)</td> 704<td class="tabledata">0.000</td> 705<td class="tabledata"><span style="font-family:Times">?</span>0.0007 (10)</td> 706<td class="tabledata">0.000</td> 707</tr> 708 709<tr> 710<td class="tabledata">C1</td> 711<td class="tabledata">0.102 (2)</td> 712<td class="tabledata">0.0775 (16)</td> 713<td class="tabledata">0.0553 (14)</td> 714<td class="tabledata">0.0109 (14)</td> 715<td class="tabledata"><span style="font-family:Times">?</span>0.0060 (13)</td> 716<td class="tabledata">0.0106 (12)</td> 717</tr> 718 719<tr> 720<td class="tabledata">C2</td> 721<td class="tabledata">0.0803 (16)</td> 722<td class="tabledata">0.0411 (11)</td> 723<td class="tabledata">0.0657 (14)</td> 724<td class="tabledata">0.0045 (10)</td> 725<td class="tabledata">0.0013 (11)</td> 726<td class="tabledata">0.0050 (9)</td> 727</tr> 728 729<tr> 730<td class="tabledata">Cl1</td> 731<td class="tabledata">0.0477 (4)</td> 732<td class="tabledata">0.0528 (4)</td> 733<td class="tabledata">0.0459 (4)</td> 734<td class="tabledata">0.000</td> 735<td class="tabledata"><span style="font-family:Times">?</span>0.0020 (3)</td> 736<td class="tabledata">0.000</td> 737</tr> 738</table> 739</div> 740 741<!-- endtablewrapadpsdiv --> 742<div class="tablewrapgeomlong"><a id="geometricparameters1" name="geometricparameters1"/> <span class="heading3">Geometric 743parameters (�, �)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span> 744<!-- endtoplinkspan --><!-- startgeom --> 745<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 746<colgroup span="4"> 747<col width="30%"/> 748<col width="20%"/> 749<col width="30%"/> 750<col width="20%"/></colgroup> 751 752<tr> 753<td width="30%" class="tabledata">N1-C2<sup>i</sup></td> 754<td width="20%" class="tabledata">1.482�(3)</td> 755<td width="30%" class="tabledata">C1-C2</td> 756<td width="20%" class="tabledata">1.495�(4)</td> 757</tr> 758 759<tr> 760<td width="30%" class="tabledata">N1-C2</td> 761<td width="20%" class="tabledata">1.482�(2)</td> 762<td width="30%" class="tabledata">C1-H11</td> 763<td width="20%" class="tabledata">0.9900</td> 764</tr> 765 766<tr> 767<td width="30%" class="tabledata">N1-H101</td> 768<td width="20%" class="tabledata">0.9200</td> 769<td width="30%" class="tabledata">C1-H12</td> 770<td width="20%" class="tabledata">0.9900</td> 771</tr> 772 773<tr> 774<td width="30%" class="tabledata">N1-H102</td> 775<td width="20%" class="tabledata">0.9200</td> 776<td width="30%" class="tabledata">C2-H21</td> 777<td width="20%" class="tabledata">0.9900</td> 778</tr> 779 780<tr> 781<td width="30%" class="tabledata">C1-C1<sup>i</sup></td> 782<td width="20%" class="tabledata">1.482�(5)</td> 783<td width="30%" class="tabledata">C2-H22</td> 784<td width="20%" class="tabledata">0.9900</td> 785</tr> 786 787<tr> 788<td width="25%" class="tabledata"/> 789<td width="25%" class="tabledata"/> 790<td width="25%" class="tabledata"/> 791<td width="25%" class="tabledata"/> 792</tr> 793 794<tr> 795<td width="30%" class="tabledata">C2<sup>i</sup>-N1-C2</td> 796<td width="20%" class="tabledata">105.9�(2)</td> 797<td width="30%" class="tabledata">C1<sup>i</sup>-C1-H12</td> 798<td width="20%" class="tabledata">110.3</td> 799</tr> 800 801<tr> 802<td width="30%" class="tabledata">C2<sup>i</sup>-N1-H101</td> 803<td width="20%" class="tabledata">110.5</td> 804<td width="30%" class="tabledata">C2-C1-H12</td> 805<td width="20%" class="tabledata">110.3</td> 806</tr> 807 808<tr> 809<td width="30%" class="tabledata">C2-N1-H101</td> 810<td width="20%" class="tabledata">110.5</td> 811<td width="30%" class="tabledata">H11-C1-H12</td> 812<td width="20%" class="tabledata">108.5</td> 813</tr> 814 815<tr> 816<td width="30%" class="tabledata">C2<sup>i</sup>-N1-H102</td> 817<td width="20%" class="tabledata">110.5</td> 818<td width="30%" class="tabledata">N1-C2-C1</td> 819<td width="20%" class="tabledata">104.64�(19)</td> 820</tr> 821 822<tr> 823<td width="30%" class="tabledata">C2-N1-H102</td> 824<td width="20%" class="tabledata">110.5</td> 825<td width="30%" class="tabledata">N1-C2-H21</td> 826<td width="20%" class="tabledata">110.8</td> 827</tr> 828 829<tr> 830<td width="30%" class="tabledata">H101-N1-H102</td> 831<td width="20%" class="tabledata">108.7</td> 832<td width="30%" class="tabledata">C1-C2-H21</td> 833<td width="20%" class="tabledata">110.8</td> 834</tr> 835 836<tr> 837<td width="30%" class="tabledata">C1<sup>i</sup>-C1-C2</td> 838<td width="20%" class="tabledata">107.20�(13)</td> 839<td width="30%" class="tabledata">N1-C2-H22</td> 840<td width="20%" class="tabledata">110.8</td> 841</tr> 842 843<tr> 844<td width="30%" class="tabledata">C1<sup>i</sup>-C1-H11</td> 845<td width="20%" class="tabledata">110.3</td> 846<td width="30%" class="tabledata">C1-C2-H22</td> 847<td width="20%" class="tabledata">110.8</td> 848</tr> 849 850<tr> 851<td width="30%" class="tabledata">C2-C1-H11</td> 852<td width="20%" class="tabledata">110.3</td> 853<td width="30%" class="tabledata">H21-C2-H22</td> 854<td width="20%" class="tabledata">108.9</td> 855</tr> 856 857<tr> 858<td width="25%" class="tabledata"/> 859<td width="25%" class="tabledata"/> 860<td width="25%" class="tabledata"/> 861<td width="25%" class="tabledata"/> 862</tr> 863 864<tr> 865<td width="30%" class="tabledata">C2<sup>i</sup>-N1-C2-C1</td> 866<td width="20%" class="tabledata">31.4�(3)</td> 867<td width="30%" class="tabledata">C1<sup>i</sup>-C1-C2-N1</td> 868<td width="20%" class="tabledata"><span style="font-family:Times">?</span>19.16�(18)</td> 869</tr> 870</table> 871 872<table style="table-layout:fixed" width="100%" class="noborder"> 873<tr> 874<td class="tabledata">Symmetry codes: (i) <i>x</i>, 875?<i>y</i>+1/2, <i>z</i>.</td> 876</tr> 877</table> 878</div> 879 880<!-- endtablewrapgeomlongdiv --> 881<div class="tablewraphbondslong"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3">Hydrogen-bond geometry (�, �)</span> 882<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 883<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 884<colgroup span="5"> 885<col width="40%"/> 886<col width="15%"/> 887<col width="15%"/> 888<col width="15%"/> 889<col width="15%"/></colgroup> 890 891<tr> 892<td width="40%" class="tabledata"> 893<i>D</i>-H���<i>A</i></td> 894<td width="15%" class="tabledata"><i>D</i>-H</td> 895<td width="15%" class="tabledata">H���<i>A</i></td> 896<td width="15%" class="tabledata"> 897<i>D</i>���<i>A</i></td> 898<td width="15%" class="tabledata"> 899<i>D</i>-H���<i>A</i></td> 900</tr> 901 902<tr> 903<td width="40%" class="tabledata">N1-H101���Cl1</td> 904<td width="15%" class="tabledata">0.92</td> 905<td width="15%" class="tabledata">2.17</td> 906<td width="15%" class="tabledata">3.091�(3)</td> 907<td width="15%" class="tabledata">180</td> 908</tr> 909 910<tr> 911<td width="40%" class="tabledata"> 912N1-H102���Cl1<sup>ii</sup></td> 913<td width="15%" class="tabledata">0.92</td> 914<td width="15%" class="tabledata">2.18</td> 915<td width="15%" class="tabledata">3.097�(2)</td> 916<td width="15%" class="tabledata">177</td> 917</tr> 918</table> 919 920<table style="table-layout:fixed" width="100%" class="noborder"> 921<tr> 922<td class="tabledata">Symmetry codes: (ii) <i>x</i>?1/2, 923<i>y</i>, ?<i>z</i>+1/2.</td> 924</tr> 925</table> 926</div> 927 928<!-- endtablewraphbondslongdiv --><!-- endcoord --><!-- endadp --> 929<!-- startgeom --><!-- endgeom --> 930<div class="tablewraphbondsshort"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3"><span class="tablenum"><b>Table 1</b></span><br/> 931Hydrogen-bond geometry (�, �)</span> 932<!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 933<table style="table-layout:fixed" width="100%" summary="" class="tabledata"> 934<colgroup span="5"> 935<col width="40%"/> 936<col width="15%"/> 937<col width="15%"/> 938<col width="15%"/> 939<col width="15%"/></colgroup> 940 941<tr> 942<td width="40%" class="tabledata"> 943<i>D</i>-H���<i>A</i></td> 944<td width="15%" class="tabledata"><i>D</i>-H</td> 945<td width="15%" class="tabledata">H���<i>A</i></td> 946<td width="15%" class="tabledata"> 947<i>D</i>���<i>A</i></td> 948<td width="15%" class="tabledata"> 949<i>D</i>-H���<i>A</i></td> 950</tr> 951 952<tr> 953<td width="40%" class="tabledata">N1-H101���Cl1</td> 954<td width="15%" class="tabledata">0.92</td> 955<td width="15%" class="tabledata">2.17</td> 956<td width="15%" class="tabledata">3.091�(3)</td> 957<td width="15%" class="tabledata">180</td> 958</tr> 959 960<tr> 961<td width="40%" class="tabledata"> 962N1-H102���Cl1<sup>i</sup></td> 963<td width="15%" class="tabledata">0.92</td> 964<td width="15%" class="tabledata">2.18</td> 965<td width="15%" class="tabledata">3.097�(2)</td> 966<td width="15%" class="tabledata">177</td> 967</tr> 968</table> 969 970<table style="table-layout:fixed" width="100%" class="noborder"> 971<tr> 972<td class="tabledata">Symmetry codes: (i) <i>x</i>?1/2, 973<i>y</i>, ?<i>z</i>+1/2.</td> 974</tr> 975</table> 976</div> 977 978<!-- endtablewraphbondsshortdiv --> 979</div> 980 981<!-- enddatablockdiv --><a id="extratables" name="extratables"/> 982 983 984<div class="acknowledgements"><a id="acknowledgements" name="acknowledgements"/> 985 986<div class="heading2">Acknowledgements <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 987</div> 988 989<!-- endheading2div --> 990<p>TK thanks the Hanns Seidel Stiftung for a personal grant funded 991by the German Bundesministerium f�r Bildung und Forschung.</p> 992</div> 993 994<!-- endacknowledgementsdiv --> 995<div class="references"><a id="references" name="references"/><a class="buttons" title="link to reference list" href="./bi2348bdy.html#References">references</a></div> 996 997<!-- endreferencesdiv --> 998<div class="publreferences"><a id="publreferences" name="publreferences"/> 999 1000<div class="heading2">References <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> 1001</div> 1002 1003<!-- endheading2div --> 1004<p>Cremer, D. & Pople, J. A. (1975). <i>J. Am. Chem. Soc.</i> 1005<b>97</b>, 1354-1358.<br/> 1006<br/> 1007Farrugia, L. J. (1997). <i>J. Appl. Cryst.</i> <b>30</b>, 1008565.<br/> 1009<br/> 1010Folmer-Anderson, J. F., Lynch, V. M. & Anslyn, E. V. (2005). 1011<i>Chem. Eur. J.</i> <b>11</b>, 5319-5326.<br/> 1012<br/> 1013Jakubas, R., Bednarska-Bolek, B., Zaleski, J., Medycki, W., 1014Holderna-Natkaniec, K., Zielinski, P. & Galazka, M. (2005). 1015<i>Solid State Sci.</i> <b>7</b>, 381-390.<br/> 1016<br/> 1017Kashino, S., Kataoka, S. & Haisa, M. (1978). <i>Bull. Chem. 1018Soc. Jpn</i>, <b>51</b>, 1717-1722.<br/> 1019<br/> 1020Moritani, Y., Sasahara, N., Kashino, S. & Haisa, M. (1987). 1021<i>Acta Cryst.</i> C<b>43</b>, 154-158.<br/> 1022<br/> 1023Nonius (2004). <i>COLLECT</i>. Nonius BV, Delft, The 1024Netherlands.<br/> 1025<br/> 1026Otwinowski, Z. & Minor, W. (1997). <i>Methods in 1027Enzymology</i>, Vol. 276, <i>Macromolecular Crystallography</i>, 1028Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. 1029New York: Academic Press.<br/> 1030<br/> 1031Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>, 1032112-122.<br/> 1033<br/> 1034</p> 1035</div> 1036 1037<!-- endpublreferencesdiv --> 1038<br/> 1039<br/> 1040<br/> 1041<br/> 1042<br/> 1043<br/> 1044<br/> 1045<br/> 1046<br/> 1047<br/> 1048<br/> 1049<br/> 1050<br/> 1051<br/> 1052<br/> 1053<br/> 1054<br/> 1055<br/> 1056<br/> 1057<br/> 1058<br/> 1059<br/> 1060<br/> 1061<br/> 1062<br/> 1063<br/> 1064<br/> 1065<br/> 1066<br/> 1067<br/> 1068<br/> 1069<br/> 1070<br/> 1071<br/> 1072<br/> 1073<br/> 1074<br/> 1075<br/> 1076<br/> 1077<br/> 1078<br/> 1079<br/> 1080<br/> 1081<br/> 1082<br/> 1083</body> 1084</html>