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- <h1 class="suptitle">supplementary materials</h1>
- <br/>
- <div class="buttonlinks"><a href="./index.html" target="_parent"><img src="../../../../../graphics/htmlborder.gif" alt="HTML version" align="top" border="0"/></a><a href="./bi2348.pdf"><img src="../../../../../graphics/pdfborder.gif" alt="pdf version" align="top" border="0"/></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?bi2348sup1"><img src="../../../../../graphics/cifborder.gif" alt="cif file" align="top" border="0"/></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?bi2348sup1&Qmime=cif">
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- <p class="scheme"><img src="./bi2348contents.gif" alt="bi2348 scheme"/></p>
- <div class="bibline">
- <p><i>Acta Cryst.</i> (2009). E<b>65</b>,
- o592 [ <a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536809006060">doi:10.1107/S1600536809006060</a>
- ]</p>
- </div>
- <h3>Pyrrolidinium chloride</h3>
- <h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Giglmeier,%20H.">
- H. Giglmeier</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Kerscher,%20T.">
- T. Kerscher</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Kl%26uuml;fers,%20P.">
- P. Klüfers</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Mayer,%20P.">
- P. Mayer</a></h3>
- <div class="abstract"><a id="abstract" name="abstract"/>
- <div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <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
- product from 2,6-bis(pyrrolidinyl)pyridine. The anion lies on the
- same cristallographic mirror plane as the N atom of the cation, the
- complete cation being generated by mirror symmetry. The anions and
- cations 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
- [100]. The pyrrolidinium cation is puckered in an envelope
- conformation <span class="it"><i>E</i></span><span class="inf"><sub>N1</sub></span>.</p>
- </div>
- <!-- endabstractdiv -->
- <div class="contentslist">
- <ul>
- <li class="comment"><a title="Comment" href="#comment">Comment</a></li>
- <li class="relatedliterature"><a title="Related literature" href="#relatedliterature">Related literature</a></li>
- <li class="experimental"><a title="Experimental" href="#experimental">Experimental</a></li>
- <li class="refinement"><a title="Refinement" href="#refinement">Refinement</a></li>
- <li class="computingdetails"><a title="Computing details" href="#computingdetails">Computing details</a></li>
- <li class="figures"><a title="Figures" href="#figures">Figures</a></li>
- <li><a title="(I)" href="#chemicalname1">Pyrrolidinium chloride</a>
- <ul>
- <li><a title="Crystal data" href="#crystaldata1">Crystal
- data</a></li>
- <li><a title="Data collection" href="#datacollection1">Data
- collection</a></li>
- <li><a title="Refinement data" href="#refinementdata1">Refinement
- data</a></li>
- <li class="specialdetails"><a title="Special details" href="#specialdetails1">Special details</a></li>
- <li class="licoords"><a title="Fractional atomic coordinates" href="#fractionalatomiccoordinates1">Fractional atomic
- coordinates</a></li>
- <li class="liadps"><a title="Atomic displacement parameters" href="#atomicdisplacement1">Atomic displacement parameters</a></li>
- <li class="ligeomlong"><a title="Geometric parameters" href="#geometricparameters1">Geometric parameters</a></li>
- <li class="lihbondslong"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li>
- <li class="lihbondsshort"><a title="Hydrogen-bond geometry" href="#hydrogen-bondgeometry1">Hydrogen-bond geometry</a></li>
- </ul>
- </li>
- <li class="acknowledgements"><a title="Acknowledgements" href="#acknowledgements">Acknowledgements</a></li>
- <li class="publreferences"><a title="References" href="#publreferences">References</a></li>
- </ul>
- </div>
- <!-- endcontentslistdiv -->
- <div class="comment"><a id="comment" name="comment"/>
- <div class="heading2">Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>The title compound was obtained as a decomposition product. The
- organic salt is composed of the pyrrolidinium cation and a chloride
- anion (Fig. 1). The crystal packing is shown in Fig. 2. In the
- crystal, both H atoms bonded to N1 of the pyrrolidinium cation are
- involved in hydrogen bonds with chloride as acceptor. Both can be
- described according to graph set analysis with a
- D<sup>1</sup><sub>1</sub>(2) descriptor on the unitary level. This
- bonding pattern leads to chains along [1 0 0] which, starting from
- chloride, can be described according to graph set analysis with a
- C<sup>2</sup><sub>1</sub>(4) descriptor on the binary level. The
- hydrogen bonding pattern is shown in Fig. 3.</p>
- <p>The <i>C<sub>s</sub></i> symmetric five-membered pyrrolidinium
- ring can be described according to Cremer & Pople (1975) by the
- puckering parameters q<sub>2</sub> = 0.3061 Å and <span style="font-family:Times">?</span><sub>2</sub> = 180.0000. The
- closest pucker descriptor is an envelope <i>E</i><sub>N1</sub>.</p>
- </div>
- <!-- endcommentdiv -->
- <div class="relatedliterature"><a id="relatedliterature" name="relatedliterature"/>
- <div class="heading2">Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>For details of the synthesis of 2,6-bis(pyrrolidinyl)pyridine,
- see: Folmer-Anderson <i>et al.</i> (2005). For related structures
- containing the pyrrolidinium cation, see: Kashino <i>et al.</i>
- (1978); Moritani <i>et al.</i> (1987); Jakubas <i>et al.</i>
- (2005). For a description of the <i>E</i><sub>N1</sub> conformation
- of the five-membered ring, see: Cremer & Pople (1975).</p>
- </div>
- <!-- endrelatedliteraturediv -->
- <div class="experimental"><a id="experimental" name="experimental"/>
- <div class="heading2">Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>The title compound was obtained as decomposition product of
- 2,6-bis(pyrrolidinyl)pyridine, which was synthesized according to
- Folmer-Anderson <i>et al.</i> (2005), after 4 months at room
- temperature.</p>
- </div>
- <!-- endexperimentaldiv -->
- <div class="refinement"><a id="refinement" name="refinement"/>
- <div class="heading2">Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>H atoms were placed in calculated positions (C-H = 0.99 Å,
- N-H = 0.92 Å) and were included in the refinement in the
- riding model approximation with <i>U</i><sub>iso</sub>(H) = 1.2
- <i>U</i><sub>eq</sub>(C/N).</p>
- </div>
- <!-- endrefinementdiv -->
- <div class="computingdetails"><a id="computingdetails" name="computingdetails"/>
- <div class="heading2">Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>Data collection: <i>COLLECT</i> (Nonius, 2004); cell refinement:
- <i>SCALEPACK</i> (Otwinowski & Minor, 1997); data reduction:
- <i>DENZO</i> and <i>SCALEPACK</i> (Otwinowski & Minor, 1997);
- program(s) used to solve structure: <i>SHELXS97</i> (Sheldrick,
- 2008); program(s) used to refine structure: <i>SHELXL97</i>
- (Sheldrick, 2008); molecular graphics: <i>ORTEP-3</i> (Farrugia,
- 1997); software used to prepare material for publication:
- <i>SHELXL97</i> (Sheldrick, 2008).</p>
- </div>
- <!-- endcomputingdetailsdiv -->
- <div class="schemes"><a href="./bi2348scheme1.gif"/></div>
- <!-- endschemesdiv -->
- <div class="figures"><a id="figures" name="figures"/>
- <div class="heading2">Figures <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <table style="table-layout:fixed" width="100%" class="nodecs">
- <colgroup span="2">
- <col width="110"/>
- <col/></colgroup>
- <tr>
- <td class="nodecs" align="center" width="110"><a href="./bi2348fig1.html"><img width="100" src="./bi2348fig1thm.gif" alt="[Figure 1]" align="middle"/></a> </td>
- <td class="nodecs" valign="middle">Fig. 1. The molecular structure
- of the <i>C<sub>s</sub></i> symmetric title compound with
- anisotropic displacement ellipsoids drawn at 50% probability for
- non-H atoms. Symmetry code: (i) <i>x</i>, -<i>y</i> + 1/2,
- <i>z</i>. </td>
- </tr>
- <tr>
- <td class="nodecs" align="center" width="110"><a href="./bi2348fig2.html"><img width="100" src="./bi2348fig2thm.gif" alt="[Figure 2]" align="middle"/></a> </td>
- <td class="nodecs" valign="middle">Fig. 2. Packing of the title
- compound, viewed along [0 1 0]. </td>
- </tr>
- <tr>
- <td class="nodecs" align="center" width="110"><a href="./bi2348fig3.html"><img width="100" src="./bi2348fig3thm.gif" alt="[Figure 3]" align="middle"/></a> </td>
- <td class="nodecs" valign="middle">Fig. 3. N-H···Cl
- hydrogen bonds lead to chain-like structures in the crystal
- structure along [1 0 0], shown here normal to [0 1 0]. Symmetry
- codes: (i) <i>x</i> + 1/2, -<i>y</i> + 1/2, -<i>z</i> + 1/2; (ii)
- <i>x</i> - 1/2, -<i>y</i> + 1/2, -<i>z</i> + 1/2; (iii) <i>x</i> -
- 1, <i>y</i>, <i>z</i>. </td>
- </tr>
- </table>
- </div>
- <!-- endfiguresdiv -->
- <div class="datablock1">
- <div class="heading2"><a id="chemicalname1" name="chemicalname1"/>Pyrrolidinium chloride <span class="toplink"><a class="buttons" href="#top">top</a></span>
- <!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <div class="tablewrapcrystaldatalong"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"/>
- <col width="50%"/></colgroup>
- <tr>
- <td width="50%" class="tabledata">
- C<sub>4</sub>H<sub>10</sub>N<sup>+</sup>·Cl<sup>-</sup></td>
- <td width="50%" class="tabledata"><i>F</i><sub>000</sub> = 232</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> =
- 107.58</td>
- <td width="50%" class="tabledata"><i>D</i><sub>x</sub> = 1.146 Mg
- m<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Orthorhombic,
- <i>P</i><i>n</i><i>m</i><i>a</i></td>
- <td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span> radiation<br/>
- <span style="font-family:Times">?</span> = 0.71073 Å</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Hall symbol: -P 2ac 2n</td>
- <td width="50%" class="tabledata">Cell parameters from 2321
- reflections</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>a</i> = 7.4429 (4) Å</td>
- <td width="50%" class="tabledata"><span style="font-family:Times">?</span> = 3.1-27.5º</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>b</i> = 9.4104 (5) Å</td>
- <td width="50%" class="tabledata">µ = 0.48 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>c</i> = 8.9021 (4) Å</td>
- <td width="50%" class="tabledata"><i>T</i> = 200 K</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>V</i> = 623.51 (5)
- Å<sup>3</sup></td>
- <td width="50%" class="tabledata">Block, colourless</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>Z</i> = 4</td>
- <td width="50%" class="tabledata">0.22 × 0.13 × 0.12
- mm</td>
- </tr>
- </table>
- <!-- endtabledatatable -->
- </div>
- <!-- endtablewrapcrystaldatalongdiv -->
- <div class="tablewrapdatacollectionlong"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data
- collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"/>
- <col width="50%"/></colgroup>
- <tr>
- <td width="50%" class="tabledata">Nonius KappaCCD<br/>
- diffractometer</td>
- <td width="50%" class="tabledata">608 reflections with <i>I</i>
- > 2<span style="font-family:Times">?</span>(<i>I</i>)</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Radiation source: rotating
- anode</td>
- <td width="50%" class="tabledata"><i>R</i><sub>int</sub> =
- 0.037</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Monochromator: MONTEL, graded
- multilayered X-ray optics</td>
- <td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>max</sub> =
- 27.5º</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>T</i> = 200 K</td>
- <td width="50%" class="tabledata"><span style="font-family:Times">?</span><sub>min</sub> =
- 3.2º</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><span style="font-family:Times">?</span> and <span style="font-family:Times">?</span> scans</td>
- <td width="50%" class="tabledata"><i>h</i> = <span style="font-family:Times">?</span>8?9</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Absorption correction: none</td>
- <td width="50%" class="tabledata"><i>k</i> = <span style="font-family:Times">?</span>12?12</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">4239 measured reflections</td>
- <td width="50%" class="tabledata"><i>l</i> = <span style="font-family:Times">?</span>11?10</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">756 independent reflections</td>
- <td width="50%" class="tabledata"/>
- </tr>
- </table>
- <!-- endtabledatatable -->
- </div>
- <!-- endtablewrapdatacollectionlongdiv -->
- <div class="tablewraprefinementdatalong"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"/>
- <col width="50%"/></colgroup>
- <tr>
- <td width="50%" class="tabledata">Refinement on
- <i>F</i><sup>2</sup></td>
- <td width="50%" class="tabledata">Secondary atom site location:
- difference Fourier map</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Least-squares matrix: full</td>
- <td width="50%" class="tabledata">Hydrogen site location: inferred
- from neighbouring sites</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup>
- > 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] =
- 0.040</td>
- <td width="50%" class="tabledata">H-atom parameters
- constrained</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) =
- 0.120</td>
- <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>
- 2</sup>) + (0.0625<i>P</i>)<sup>2</sup> + 0.1854<i>P</i>]<br/>
- where <i>P</i> = (<i>F</i><sub>o</sub><sup>2</sup> +
- 2<i>F</i><sub>c</sub><sup>2</sup>)/3</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>S</i> = 1.07</td>
- <td width="50%" class="tabledata">(?/<span style="font-family:Times">?</span>)<sub>max</sub> <
- 0.001</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">756 reflections</td>
- <td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 0.21 e
- Å<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">31 parameters</td>
- <td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>0.23 e Å<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Primary atom site location:
- structure-invariant direct methods</td>
- <td width="50%" class="tabledata">Extinction correction: none</td>
- </tr>
- </table>
- <!-- endtabledatatable -->
- </div>
- <!-- endtablewraprefinementdatalongdiv -->
- <div class="tablewrapcrystaldatashort"><a id="crystaldata1" name="crystaldata1"/><span class="heading3">Crystal data</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"/>
- <col width="50%"/></colgroup>
- <tr>
- <td width="50%" class="tabledata">
- C<sub>4</sub>H<sub>10</sub>N<sup>+</sup>·Cl<sup>-</sup></td>
- <td width="50%" class="tabledata"><i>V</i> = 623.51 (5)
- Å<sup>3</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>M</i><i><sub>r</sub></i> =
- 107.58</td>
- <td width="50%" class="tabledata"><i>Z</i> = 4</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Orthorhombic,
- <i>P</i><i>n</i><i>m</i><i>a</i></td>
- <td width="50%" class="tabledata">Mo <i>K</i><span style="font-family:Times">?</span></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>a</i> = 7.4429 (4) Å</td>
- <td width="50%" class="tabledata">µ = 0.48 mm<span style="font-family:Times"><sup>?</sup></span><sup>1</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>b</i> = 9.4104 (5) Å</td>
- <td width="50%" class="tabledata"><i>T</i> = 200 K</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>c</i> = 8.9021 (4) Å</td>
- <td width="50%" class="tabledata">0.22 × 0.13 × 0.12
- mm</td>
- </tr>
- </table>
- <!-- endtabledatatable -->
- </div>
- <!-- endtablewrapcrystaldatashortdiv -->
- <div class="tablewrapdatacollectionshort"><a id="datacollection1" name="datacollection1"/><span class="heading3">Data
- collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"/>
- <col width="50%"/></colgroup>
- <tr>
- <td width="50%" class="tabledata">Nonius KappaCCD<br/>
- diffractometer</td>
- <td width="50%" class="tabledata">756 independent reflections</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">Absorption correction: none</td>
- <td width="50%" class="tabledata">608 reflections with <i>I</i>
- > 2<span style="font-family:Times">?</span>(<i>I</i>)</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">4239 measured reflections</td>
- <td width="50%" class="tabledata"><i>R</i><sub>int</sub> =
- 0.037</td>
- </tr>
- </table>
- <!-- endtabledatatable -->
- </div>
- <!-- endtablewrapdatacollectionshortdiv -->
- <div class="tablewraprefinementdatashort"><a id="refinementdata1" name="refinementdata1"/><span class="heading3">Refinement</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"/>
- <col width="50%"/></colgroup>
- <tr>
- <td width="50%" class="tabledata"><i>R</i>[<i>F</i><sup>2</sup>
- > 2<span style="font-family:Times">?</span>(<i>F</i><sup>2</sup>)] =
- 0.040</td>
- <td width="50%" class="tabledata">31 parameters</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>wR</i>(<i>F</i><sup>2</sup>) =
- 0.120</td>
- <td width="50%" class="tabledata">H-atom parameters
- constrained</td>
- </tr>
- <tr>
- <td width="50%" class="tabledata"><i>S</i> = 1.07</td>
- <td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>max</sub> = 0.21 e
- Å<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td>
- </tr>
- <tr>
- <td width="50%" class="tabledata">756 reflections</td>
- <td width="50%" class="tabledata">?<span style="font-family:Times">?</span><sub>min</sub> = <span style="font-family:Times">?</span>0.23 e Å<span style="font-family:Times"><sup>?</sup></span><sup>3</sup></td>
- </tr>
- </table>
- <!-- endtabledatatable -->
- </div>
- <!-- endtablewraprefinementdatashortdiv -->
- <div class="specialdetails"><a id="specialdetails1" name="specialdetails1"/><span class="heading3">Special
- details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="100%" class="tabledata">
- <tr>
- <td class="tabledata">
- <p><b>Refinement</b>. Hydrogen atoms were placed in calculated
- positions (C-H 0.99 Å for methylene C atoms and N-H 0.92
- Å for N atoms) and were included in the refinement in the
- riding model approximation with U(H) set to 1.2
- <i>U</i><sub>eq</sub>(C) for C atoms and 1.2
- <i>U</i><sub>eq</sub>(N) for N atoms.</p>
- </td>
- </tr>
- </table>
- </div>
- <!-- endspecialdetailsdiv -->
- <div class="tablewrapcoords"><a id="fractionalatomiccoordinates1" name="fractionalatomiccoordinates1"/> <span class="heading3">Fractional atomic coordinates and isotropic or
- equivalent isotropic displacement parameters
- (Å<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span>
- <!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="100%" summary="" class="tabledata">
- <tr>
- <td class="tabledata"/>
- <td class="tabledata"><i>x</i></td>
- <td class="tabledata"><i>y</i></td>
- <td class="tabledata"><i>z</i></td>
- <td class="tabledata">
- <i>U</i><sub>iso</sub>*/<i>U</i><sub>eq</sub></td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">N1</td>
- <td class="tabledata">0.2072 (3)</td>
- <td class="tabledata">0.2500</td>
- <td class="tabledata">0.3955 (3)</td>
- <td class="tabledata">0.0473 (6)</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">H101</td>
- <td class="tabledata">0.2341</td>
- <td class="tabledata">0.2500</td>
- <td class="tabledata">0.2946</td>
- <td class="tabledata">0.057*</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">H102</td>
- <td class="tabledata">0.0843</td>
- <td class="tabledata">0.2500</td>
- <td class="tabledata">0.4065</td>
- <td class="tabledata">0.057*</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">C1</td>
- <td class="tabledata">0.3204 (4)</td>
- <td class="tabledata">0.1712 (3)</td>
- <td class="tabledata">0.6283 (3)</td>
- <td class="tabledata">0.0781 (8)</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">H11</td>
- <td class="tabledata">0.2249</td>
- <td class="tabledata">0.1348</td>
- <td class="tabledata">0.6954</td>
- <td class="tabledata">0.094*</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">H12</td>
- <td class="tabledata">0.4376</td>
- <td class="tabledata">0.1348</td>
- <td class="tabledata">0.6641</td>
- <td class="tabledata">0.094*</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">C2</td>
- <td class="tabledata">0.2871 (3)</td>
- <td class="tabledata">0.1242 (2)</td>
- <td class="tabledata">0.4702 (3)</td>
- <td class="tabledata">0.0623 (6)</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">H21</td>
- <td class="tabledata">0.4009</td>
- <td class="tabledata">0.0963</td>
- <td class="tabledata">0.4208</td>
- <td class="tabledata">0.075*</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">H22</td>
- <td class="tabledata">0.2032</td>
- <td class="tabledata">0.0427</td>
- <td class="tabledata">0.4677</td>
- <td class="tabledata">0.075*</td>
- <td class="tabledata"/>
- </tr>
- <tr>
- <td class="tabledata">Cl1</td>
- <td class="tabledata">0.29515 (8)</td>
- <td class="tabledata">0.2500</td>
- <td class="tabledata">0.05610 (7)</td>
- <td class="tabledata">0.0488 (3)</td>
- <td class="tabledata"/>
- </tr>
- </table>
- </div>
- <!-- endtablewrapcoordsdiv -->
- <div class="tablewrapadps"><a id="atomicdisplacement1" name="atomicdisplacement1"/> <span class="heading3">Atomic
- displacement parameters (Å<sup>2</sup>)</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="100%" summary="" class="tabledata">
- <tr>
- <td class="tabledata"/>
- <td class="tabledata"><i>U</i><sup>11</sup></td>
- <td class="tabledata"><i>U</i><sup>22</sup></td>
- <td class="tabledata"><i>U</i><sup>33</sup></td>
- <td class="tabledata"><i>U</i><sup>12</sup></td>
- <td class="tabledata"><i>U</i><sup>13</sup></td>
- <td class="tabledata"><i>U</i><sup>23</sup></td>
- </tr>
- <tr>
- <td class="tabledata">N1</td>
- <td class="tabledata">0.0466 (12)</td>
- <td class="tabledata">0.0500 (13)</td>
- <td class="tabledata">0.0452 (12)</td>
- <td class="tabledata">0.000</td>
- <td class="tabledata"><span style="font-family:Times">?</span>0.0007 (10)</td>
- <td class="tabledata">0.000</td>
- </tr>
- <tr>
- <td class="tabledata">C1</td>
- <td class="tabledata">0.102 (2)</td>
- <td class="tabledata">0.0775 (16)</td>
- <td class="tabledata">0.0553 (14)</td>
- <td class="tabledata">0.0109 (14)</td>
- <td class="tabledata"><span style="font-family:Times">?</span>0.0060 (13)</td>
- <td class="tabledata">0.0106 (12)</td>
- </tr>
- <tr>
- <td class="tabledata">C2</td>
- <td class="tabledata">0.0803 (16)</td>
- <td class="tabledata">0.0411 (11)</td>
- <td class="tabledata">0.0657 (14)</td>
- <td class="tabledata">0.0045 (10)</td>
- <td class="tabledata">0.0013 (11)</td>
- <td class="tabledata">0.0050 (9)</td>
- </tr>
- <tr>
- <td class="tabledata">Cl1</td>
- <td class="tabledata">0.0477 (4)</td>
- <td class="tabledata">0.0528 (4)</td>
- <td class="tabledata">0.0459 (4)</td>
- <td class="tabledata">0.000</td>
- <td class="tabledata"><span style="font-family:Times">?</span>0.0020 (3)</td>
- <td class="tabledata">0.000</td>
- </tr>
- </table>
- </div>
- <!-- endtablewrapadpsdiv -->
- <div class="tablewrapgeomlong"><a id="geometricparameters1" name="geometricparameters1"/> <span class="heading3">Geometric
- parameters (Å, °)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span>
- <!-- endtoplinkspan --><!-- startgeom -->
- <table style="table-layout:fixed" width="100%" summary="" class="tabledata">
- <colgroup span="4">
- <col width="30%"/>
- <col width="20%"/>
- <col width="30%"/>
- <col width="20%"/></colgroup>
- <tr>
- <td width="30%" class="tabledata">N1-C2<sup>i</sup></td>
- <td width="20%" class="tabledata">1.482 (3)</td>
- <td width="30%" class="tabledata">C1-C2</td>
- <td width="20%" class="tabledata">1.495 (4)</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">N1-C2</td>
- <td width="20%" class="tabledata">1.482 (2)</td>
- <td width="30%" class="tabledata">C1-H11</td>
- <td width="20%" class="tabledata">0.9900</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">N1-H101</td>
- <td width="20%" class="tabledata">0.9200</td>
- <td width="30%" class="tabledata">C1-H12</td>
- <td width="20%" class="tabledata">0.9900</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">N1-H102</td>
- <td width="20%" class="tabledata">0.9200</td>
- <td width="30%" class="tabledata">C2-H21</td>
- <td width="20%" class="tabledata">0.9900</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C1-C1<sup>i</sup></td>
- <td width="20%" class="tabledata">1.482 (5)</td>
- <td width="30%" class="tabledata">C2-H22</td>
- <td width="20%" class="tabledata">0.9900</td>
- </tr>
- <tr>
- <td width="25%" class="tabledata"/>
- <td width="25%" class="tabledata"/>
- <td width="25%" class="tabledata"/>
- <td width="25%" class="tabledata"/>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2<sup>i</sup>-N1-C2</td>
- <td width="20%" class="tabledata">105.9 (2)</td>
- <td width="30%" class="tabledata">C1<sup>i</sup>-C1-H12</td>
- <td width="20%" class="tabledata">110.3</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2<sup>i</sup>-N1-H101</td>
- <td width="20%" class="tabledata">110.5</td>
- <td width="30%" class="tabledata">C2-C1-H12</td>
- <td width="20%" class="tabledata">110.3</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2-N1-H101</td>
- <td width="20%" class="tabledata">110.5</td>
- <td width="30%" class="tabledata">H11-C1-H12</td>
- <td width="20%" class="tabledata">108.5</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2<sup>i</sup>-N1-H102</td>
- <td width="20%" class="tabledata">110.5</td>
- <td width="30%" class="tabledata">N1-C2-C1</td>
- <td width="20%" class="tabledata">104.64 (19)</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2-N1-H102</td>
- <td width="20%" class="tabledata">110.5</td>
- <td width="30%" class="tabledata">N1-C2-H21</td>
- <td width="20%" class="tabledata">110.8</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">H101-N1-H102</td>
- <td width="20%" class="tabledata">108.7</td>
- <td width="30%" class="tabledata">C1-C2-H21</td>
- <td width="20%" class="tabledata">110.8</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C1<sup>i</sup>-C1-C2</td>
- <td width="20%" class="tabledata">107.20 (13)</td>
- <td width="30%" class="tabledata">N1-C2-H22</td>
- <td width="20%" class="tabledata">110.8</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C1<sup>i</sup>-C1-H11</td>
- <td width="20%" class="tabledata">110.3</td>
- <td width="30%" class="tabledata">C1-C2-H22</td>
- <td width="20%" class="tabledata">110.8</td>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2-C1-H11</td>
- <td width="20%" class="tabledata">110.3</td>
- <td width="30%" class="tabledata">H21-C2-H22</td>
- <td width="20%" class="tabledata">108.9</td>
- </tr>
- <tr>
- <td width="25%" class="tabledata"/>
- <td width="25%" class="tabledata"/>
- <td width="25%" class="tabledata"/>
- <td width="25%" class="tabledata"/>
- </tr>
- <tr>
- <td width="30%" class="tabledata">C2<sup>i</sup>-N1-C2-C1</td>
- <td width="20%" class="tabledata">31.4 (3)</td>
- <td width="30%" class="tabledata">C1<sup>i</sup>-C1-C2-N1</td>
- <td width="20%" class="tabledata"><span style="font-family:Times">?</span>19.16 (18)</td>
- </tr>
- </table>
- <table style="table-layout:fixed" width="100%" class="noborder">
- <tr>
- <td class="tabledata">Symmetry codes: (i) <i>x</i>,
- ?<i>y</i>+1/2, <i>z</i>.</td>
- </tr>
- </table>
- </div>
- <!-- endtablewrapgeomlongdiv -->
- <div class="tablewraphbondslong"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3">Hydrogen-bond geometry (Å, °)</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="100%" summary="" class="tabledata">
- <colgroup span="5">
- <col width="40%"/>
- <col width="15%"/>
- <col width="15%"/>
- <col width="15%"/>
- <col width="15%"/></colgroup>
- <tr>
- <td width="40%" class="tabledata">
- <i>D</i>-H···<i>A</i></td>
- <td width="15%" class="tabledata"><i>D</i>-H</td>
- <td width="15%" class="tabledata">H···<i>A</i></td>
- <td width="15%" class="tabledata">
- <i>D</i>···<i>A</i></td>
- <td width="15%" class="tabledata">
- <i>D</i>-H···<i>A</i></td>
- </tr>
- <tr>
- <td width="40%" class="tabledata">N1-H101···Cl1</td>
- <td width="15%" class="tabledata">0.92</td>
- <td width="15%" class="tabledata">2.17</td>
- <td width="15%" class="tabledata">3.091 (3)</td>
- <td width="15%" class="tabledata">180</td>
- </tr>
- <tr>
- <td width="40%" class="tabledata">
- N1-H102···Cl1<sup>ii</sup></td>
- <td width="15%" class="tabledata">0.92</td>
- <td width="15%" class="tabledata">2.18</td>
- <td width="15%" class="tabledata">3.097 (2)</td>
- <td width="15%" class="tabledata">177</td>
- </tr>
- </table>
- <table style="table-layout:fixed" width="100%" class="noborder">
- <tr>
- <td class="tabledata">Symmetry codes: (ii) <i>x</i>?1/2,
- <i>y</i>, ?<i>z</i>+1/2.</td>
- </tr>
- </table>
- </div>
- <!-- endtablewraphbondslongdiv --><!-- endcoord --><!-- endadp -->
- <!-- startgeom --><!-- endgeom -->
- <div class="tablewraphbondsshort"><a id="hydrogen-bondgeometry1" name="hydrogen-bondgeometry1"/> <span class="heading3"><span class="tablenum"><b>Table 1</b></span><br/>
- Hydrogen-bond geometry (Å, °)</span>
- <!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- <table style="table-layout:fixed" width="100%" summary="" class="tabledata">
- <colgroup span="5">
- <col width="40%"/>
- <col width="15%"/>
- <col width="15%"/>
- <col width="15%"/>
- <col width="15%"/></colgroup>
- <tr>
- <td width="40%" class="tabledata">
- <i>D</i>-H···<i>A</i></td>
- <td width="15%" class="tabledata"><i>D</i>-H</td>
- <td width="15%" class="tabledata">H···<i>A</i></td>
- <td width="15%" class="tabledata">
- <i>D</i>···<i>A</i></td>
- <td width="15%" class="tabledata">
- <i>D</i>-H···<i>A</i></td>
- </tr>
- <tr>
- <td width="40%" class="tabledata">N1-H101···Cl1</td>
- <td width="15%" class="tabledata">0.92</td>
- <td width="15%" class="tabledata">2.17</td>
- <td width="15%" class="tabledata">3.091 (3)</td>
- <td width="15%" class="tabledata">180</td>
- </tr>
- <tr>
- <td width="40%" class="tabledata">
- N1-H102···Cl1<sup>i</sup></td>
- <td width="15%" class="tabledata">0.92</td>
- <td width="15%" class="tabledata">2.18</td>
- <td width="15%" class="tabledata">3.097 (2)</td>
- <td width="15%" class="tabledata">177</td>
- </tr>
- </table>
- <table style="table-layout:fixed" width="100%" class="noborder">
- <tr>
- <td class="tabledata">Symmetry codes: (i) <i>x</i>?1/2,
- <i>y</i>, ?<i>z</i>+1/2.</td>
- </tr>
- </table>
- </div>
- <!-- endtablewraphbondsshortdiv -->
- </div>
- <!-- enddatablockdiv --><a id="extratables" name="extratables"/>
- <div class="acknowledgements"><a id="acknowledgements" name="acknowledgements"/>
- <div class="heading2">Acknowledgements <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>TK thanks the Hanns Seidel Stiftung for a personal grant funded
- by the German Bundesministerium für Bildung und Forschung.</p>
- </div>
- <!-- endacknowledgementsdiv -->
- <div class="references"><a id="references" name="references"/><a class="buttons" title="link to reference list" href="./bi2348bdy.html#References">references</a></div>
- <!-- endreferencesdiv -->
- <div class="publreferences"><a id="publreferences" name="publreferences"/>
- <div class="heading2">References <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <p>Cremer, D. & Pople, J. A. (1975). <i>J. Am. Chem. Soc.</i>
- <b>97</b>, 1354-1358.<br/>
- <br/>
- Farrugia, L. J. (1997). <i>J. Appl. Cryst.</i> <b>30</b>,
- 565.<br/>
- <br/>
- Folmer-Anderson, J. F., Lynch, V. M. & Anslyn, E. V. (2005).
- <i>Chem. Eur. J.</i> <b>11</b>, 5319-5326.<br/>
- <br/>
- Jakubas, R., Bednarska-Bolek, B., Zaleski, J., Medycki, W.,
- Holderna-Natkaniec, K., Zielinski, P. & Galazka, M. (2005).
- <i>Solid State Sci.</i> <b>7</b>, 381-390.<br/>
- <br/>
- Kashino, S., Kataoka, S. & Haisa, M. (1978). <i>Bull. Chem.
- Soc. Jpn</i>, <b>51</b>, 1717-1722.<br/>
- <br/>
- Moritani, Y., Sasahara, N., Kashino, S. & Haisa, M. (1987).
- <i>Acta Cryst.</i> C<b>43</b>, 154-158.<br/>
- <br/>
- Nonius (2004). <i>COLLECT</i>. Nonius BV, Delft, The
- Netherlands.<br/>
- <br/>
- Otwinowski, Z. & Minor, W. (1997). <i>Methods in
- Enzymology</i>, Vol. 276, <i>Macromolecular Crystallography</i>,
- Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326.
- New York: Academic Press.<br/>
- <br/>
- Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>,
- 112-122.<br/>
- <br/>
- </p>
- </div>
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