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- <a name="top"></a><h1 class="suptitle">supplementary materials</h1><br /><div class="buttonlinks"><a href="./index.html" target="_parent"><img src="../../../../../graphics/htmlborder.gif" alt="HTML version" align="top" border="0" /></a><a href="./at2638.pdf" ><img src="../../../../../graphics/pdfborder.gif" alt="pdf version" align="top" border="0" /></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?at2638sup1" ><img src="../../../../../graphics/cifborder.gif" alt="cif file" align="top" border="0" /></a><a href="http://scripts.iucr.org/cgi-bin/sendcif?at2638sup1&Qmime=cif" ><img src="../../../../../graphics/3dviewborder.gif" alt="3d view" align="top" border="0" /></a><a href="./at2638Isup2.hkl" ><img src="../../../../../graphics/structurefactorsborder.gif" alt="structure factors" align="top" border="0" /></a><a href="./at2638sup0.html" ><img src="../../../../../graphics/supplementarymaterialsborder.gif" alt="supplementary materials" align="top" border="0" /></a><a href="./at2638checkcif.html" ><img src="../../../../../graphics/checkcifborder.gif" alt="CIF check report" align="top" border="0" /></a><a href="http://scripts.iucr.org/cgi-bin/similar?wordList=nitrophenoxy%20or%20propoxy%20or%20aniline&from=at2638" ><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><p class="scheme"><img src="./at2638contents.gif" alt="at2638 scheme" /></p><div class="bibline"><p><i>Acta Cryst.</i> (2008). E<b>64</b>, o2110 [ <font size="2"><a title="Open URL link" href="http://dx.doi.org/10.1107/S1600536808032406">doi:10.1107/S1600536808032406</a></font> ]</p></div>
- <h3>4-[3-(4-Nitrophenoxy)propoxy]aniline</h3><h3><a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Zheng,%20L.-M.">L.-M. Zheng</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Wei,%20X.">X. Wei</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Peng,%20X.-R.">X.-R. Peng</a>, <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Zeng,%20J.-P.">J.-P. Zeng</a> and <a href="http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Zhang,%20Y.-Q.">Y.-Q. Zhang</a></h3>
- <div class="abstract">
- <a name="abstract"></a>
- <div class="heading2">Abstract <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p>The molecules of the title compound, C<span class="inf"><sub>15</sub></span>H<span class="inf"><sub>16</sub></span>N<span class="inf"><sub>2</sub></span>O<span class="inf"><sub>4</sub></span>, are linked <span class="it"><i>via</i></span> N-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" />O hydrogen bonds, forming undulating one-dimensional chains. Adjacent chains are linked by weak C-H<img alt="..." border="0" src="/logos/entities/ctdot_rmgif.gif" /><img alt="[pi]" border="0" src="/logos/entities/pi_rmgif.gif" /> interactions, forming a three-dimensional network.</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">4-[3-(4-Nitrophenoxy)propoxy]aniline </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 name="comment"></a>
- <div class="heading2">
- Comment <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p>As part of our ongoing investigation on bibenzene compound, we present the
- crystal structure of the title compound (I) containing multiple functional
- groups that can develop strong interactions with cucurbit[<i>n</i>]urils
- (CB[<i>n</i>]) (Freeman <i>et al.</i>, 1981; Day & Arnold,
- 2000; Day <i>et
- al.</i>, 2002; Kim <i>et al.</i>, 2000)</p><p>The crystal structure of (I) is shown in Fig.1. Two phenyl rings were linked by
- ethereal chain forming a non-coplanar structure and the dihedral angle between
- two phenyl ring is 26.13 (9) Å. Molecules are linked <i>via</i> N2—H2B···O1
- hydrogen bonds forming a undulant one-dimensional chains (Fig. 2) and adjacent
- chains are linked by C—H···<span style="font-family:Times">π</span> interaction forming a three-dimensional
- framework (Table 1, <i>Cg</i>1 and <i>Cg</i>2 are centroids of the phenyl ring
- (C1—C6) and (C10—C15), respectively).</p>
- </div>
- <!-- endcommentdiv -->
- <div class="relatedliterature">
- <a name="relatedliterature"></a>
- <div class="heading2">
- Related literature <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p>For general background, see: Day & Arnold (2000); Day <i>et al.</i>
- (2002);
- Freeman <i>et al.</i> (1981); Kim <i>et al.</i> (2000).
- <i>Cg</i>1 and
- <i>Cg</i>2 are the centroids of the C1–C6 and C10–C15 phenyl rings,
- respectively</p>
- </div>
- <!-- endrelatedliteraturediv -->
- <div class="experimental">
- <a name="experimental"></a>
- <div class="heading2">
- Experimental <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p><i>P</i>-toluenesulfonyl chloride (7.62 g, 40 mmol) was added slowly, whilst
- stirring, to a pyridine solution (50 ml) containing 1,3-propanediol (1.52 g,
- 20 mmol). The mixture was stirred for about 4 h in the range of 268 K - 278 K.
- Water (40 ml) was added to the resulting solution, the precipitate was
- collected by filtration, the solid product was crystallized using ethanol. The
- solid product (6.85 g, 20 mmol) dissolved in DMF (100 ml) containing K<sub>2</sub>CO<sub>3</sub>
- (2 g), <i>p</i>-nitrophenol (0.54 g, 4 mmol) was added slowly, to the DMF(100 ml) solution, and the mixture was heated at 353 K for 24 h, and then the
- solvent was removed into water and filtered, the residue was washed with
- water, and 1,3-bis(-nitrylphenoxy)-propane was obtained. Hydrazine (30 g,80%)
- was added slowly to a stirred solution of ethanol (50 ml) containing
- 1,4-bis(-nitrylphenoxy)-propane (3.12 g, 10 mmol), FeCl<sub>3</sub>.6H<sub>2</sub>O (0.8 g) and
- active carbon (1.8 g) at 348 K for 5 h, and then the solvent was filtered,
- the solid product was crystallized using ethanol, Single crystals of (I) were
- obtained after a week.</p>
- </div>
- <!-- endexperimentaldiv -->
- <div class="refinement">
- <a name="refinement"></a>
- <div class="heading2">
- Refinement <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p>All H atoms were placed in calculated positions and refined as riding, with
- C—H = 0.97 Å (methylene) and 0.93 Å (aromatic), N—H = 0.861 Å, and
- <i>U</i><sub>iso</sub>(H) = 1.2<i>U</i><sub>eq</sub>(C,<i>N</i>).</p>
- </div>
- <!-- endrefinementdiv -->
- <div class="computingdetails">
- <a name="computingdetails"></a>
- <div class="heading2">
- Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p>Data collection: <i>APEX2</i> (Bruker, 2005); cell refinement: <i>SAINT</i> (Bruker, 2005); data reduction: <i>SAINT</i> (Bruker, 2005); 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 for Windows</i> (Farrugia, 1997); software used to prepare material for publication: <i>WinGX</i> (Farrugia, 1999).</p>
- </div>
- <!-- endcomputingdetailsdiv -->
- <div class="schemes">
- <a href="./at2638scheme1.gif"></a>
- </div>
- <!-- endschemesdiv -->
- <div class="figures">
- <div class="tablewrap">
- <a name="figures"></a>
- <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>
- <col></col>
- </colgroup>
- <tr><td class="nodecs" align="center" width="110">
- <a href="./at2638fig1.html"><img width="100" src="./at2638fig1thm.gif" alt="[Figure 1]" align="middle"/></a>
- </td><td class="nodecs" valign="middle" >
- <font size="2">Fig. 1. The molecular structure of (I), showing the atom-labelling scheme.
- Displacement ellipsoids are drawn at the 30% probability level.</font>
- </td></tr>
- <tr><td class="nodecs" align="center" width="110">
- <a href="./at2638fig2.html"><img width="100" src="./at2638fig2thm.gif" alt="[Figure 2]" align="middle"/></a>
- </td><td class="nodecs" valign="middle" >
- <font size="2">Fig. 2. Packing diagram of (I). Hydrogen bonds are shown as dashed lines.</font>
- </td></tr>
- </table>
- </div>
- </div>
- <!-- endfiguresdiv -->
- <div class="datablock1">
- <div class="heading2">
- <a name="chemicalname1"></a>4-[3-(4-Nitrophenoxy)propoxy]aniline <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div -->
- <div class="tablewrapcrystaldatalong">
- <a name="crystaldata1"></a><span class="heading3">Crystal data</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"></col>
- <col width="50%"></col>
- </colgroup>
- <tr><td width="50%" class="tabledata" >C<sub>15</sub>H<sub>16</sub>N<sub>2</sub>O<sub>4</sub></td><td width="50%" class="tabledata" ><i>F</i><sub>000</sub> = 1216</td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 288.30</td><td width="50%" class="tabledata" ><i>D</i><sub>x</sub> = 1.341 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>c</i><i>c</i><i>n</i></td><td width="50%" class="tabledata" >Mo <i>K</i><span style="font-family:Times">α</span> radiation, <span style="font-family:Times">λ</span> = 0.71073 Å</td></tr><tr><td width="50%" class="tabledata" >Hall symbol: -P 2ab 2ac</td><td width="50%" class="tabledata" >Cell parameters from 2509 reflections</td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 10.808 (8) Å</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span> = 2.0–25.0º</td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 34.79 (3) Å</td><td width="50%" class="tabledata" >µ = 0.10 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 7.596 (6) Å</td><td width="50%" class="tabledata" ><i>T</i> = 298 K</td></tr><tr><td width="50%" class="tabledata" ><i>V</i> = 2857 (4) Å<sup>3</sup></td><td width="50%" class="tabledata" >Prism, brown</td></tr><tr><td width="50%" class="tabledata" ><i>Z</i> = 8</td><td width="50%" class="tabledata" >0.23 × 0.19 × 0.16 mm</td></tr></table><!-- endtabledatatable -->
- </div>
- <!-- endtablewrapcrystaldatalongdiv -->
- <div class="tablewrapdatacollectionlong">
- <a name="datacollection1"></a><span class="heading3">Data collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"></col>
- <col width="50%"></col>
- </colgroup>
- <tr><td width="50%" class="tabledata" >Bruker APEXII CCD area-detector <br />diffractometer</td><td width="50%" class="tabledata" >2509 independent reflections</td></tr><tr><td width="50%" class="tabledata" >Radiation source: fine-focus sealed tube</td><td width="50%" class="tabledata" >1554 reflections with <i>I</i> > 2<span style="font-family:Times">σ</span>(<i>I</i>)</td></tr><tr><td width="50%" class="tabledata" >Monochromator: graphite</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.065</td></tr><tr><td width="50%" class="tabledata" ><i>T</i> = 298 K</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>max</sub> = 25.0º</td></tr><tr><td width="50%" class="tabledata" ><span style="font-family:Times">φ</span> and <span style="font-family:Times">ω</span> scans</td><td width="50%" class="tabledata" ><span style="font-family:Times">θ</span><sub>min</sub> = 2.0º</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: multi-scan<br />(SADABS; Bruker, 2005)</td><td width="50%" class="tabledata" ><i>h</i> = <span style="font-family:Times">−</span>12→12</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.978, <i>T</i><sub>max</sub> = 0.984</td><td width="50%" class="tabledata" ><i>k</i> = <span style="font-family:Times">−</span>37→41</td></tr><tr><td width="50%" class="tabledata" >17736 measured reflections</td><td width="50%" class="tabledata" ><i>l</i> = <span style="font-family:Times">−</span>8→9</td></tr></table><!-- endtabledatatable -->
- </div>
- <!-- endtablewrapdatacollectionlongdiv -->
- <div class="tablewraprefinementdatalong">
- <a name="refinementdata1"></a><span class="heading3">Refinement</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"></col>
- <col width="50%"></col>
- </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">σ</span>(<i>F</i><sup>2</sup>)] = 0.046</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>) = 0.126</td><td width="50%" class="tabledata" >  <i>w</i> = 1/[<span style="font-family:Times">σ</span><sup>2</sup>(<i>F</i><sub>o</sub><sup>2</sup>) + (0.0596<i>P</i>)<sup>2</sup>] <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> = 1.05</td><td width="50%" class="tabledata" >(Δ/<span style="font-family:Times">σ</span>)<sub>max</sub> = 0.001</td></tr><tr><td width="50%" class="tabledata" >2509 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.25 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >190 parameters</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.16 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 name="crystaldata1"></a><span class="heading3">Crystal data</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"></col>
- <col width="50%"></col>
- </colgroup>
- <tr><td width="50%" class="tabledata" >C<sub>15</sub>H<sub>16</sub>N<sub>2</sub>O<sub>4</sub></td><td width="50%" class="tabledata" ><i>V</i> = 2857 (4) Å<sup>3</sup></td></tr><tr><td width="50%" class="tabledata" ><i>M</i><i><sub>r</sub></i> = 288.30</td><td width="50%" class="tabledata" ><i>Z</i> = 8</td></tr><tr><td width="50%" class="tabledata" >Orthorhombic, <i>P</i><i>c</i><i>c</i><i>n</i></td><td width="50%" class="tabledata" >Mo <i>K</i><span style="font-family:Times">α</span></td></tr><tr><td width="50%" class="tabledata" ><i>a</i> = 10.808 (8) Å</td><td width="50%" class="tabledata" >µ = 0.10 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td width="50%" class="tabledata" ><i>b</i> = 34.79 (3) Å</td><td width="50%" class="tabledata" ><i>T</i> = 298 K</td></tr><tr><td width="50%" class="tabledata" ><i>c</i> = 7.596 (6) Å</td><td width="50%" class="tabledata" >0.23 × 0.19 × 0.16 mm</td></tr></table><!-- endtabledatatable -->
- </div>
- <!-- endtablewrapcrystaldatashortdiv -->
- <div class="tablewrapdatacollectionshort">
- <a name="datacollection1"></a><span class="heading3">Data collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"></col>
- <col width="50%"></col>
- </colgroup>
- <tr><td width="50%" class="tabledata" >Bruker APEXII CCD area-detector <br />diffractometer</td><td width="50%" class="tabledata" >2509 independent reflections</td></tr><tr><td width="50%" class="tabledata" >Absorption correction: multi-scan<br />(SADABS; Bruker, 2005)</td><td width="50%" class="tabledata" >1554 reflections with <i>I</i> > 2<span style="font-family:Times">σ</span>(<i>I</i>)</td></tr><tr><td width="50%" class="tabledata" ><i>T</i><sub>min</sub> = 0.978, <i>T</i><sub>max</sub> = 0.984</td><td width="50%" class="tabledata" ><i>R</i><sub>int</sub> = 0.065</td></tr><tr><td width="50%" class="tabledata" >17736 measured reflections</td><td width="50%" class="tabledata" ></td></tr></table><!-- endtabledatatable -->
- </div>
- <!-- endtablewrapdatacollectionshortdiv -->
- <div class="tablewraprefinementdatashort">
- <a name="refinementdata1"></a><span class="heading3">Refinement</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table style="table-layout:fixed" width="80%" summary="" class="tabledata">
- <colgroup span="2">
- <col width="50%"></col>
- <col width="50%"></col>
- </colgroup>
- <tr><td width="50%" class="tabledata" ><i>R</i>[<i>F</i><sup>2</sup> > 2<span style="font-family:Times">σ</span>(<i>F</i><sup>2</sup>)] = 0.046</td><td width="50%" class="tabledata" >190 parameters</td></tr><tr><td width="50%" class="tabledata" ><i>wR</i>(<i>F</i><sup>2</sup>) = 0.126</td><td width="50%" class="tabledata" >H-atom parameters constrained</td></tr><tr><td width="50%" class="tabledata" ><i>S</i> = 1.05</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.25 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td width="50%" class="tabledata" >2509 reflections</td><td width="50%" class="tabledata" >Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.16 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr></table><!-- endtabledatatable -->
- </div>
- <!-- endtablewraprefinementdatashortdiv -->
- <div class="specialdetails">
- <div class="tablewrap">
- <a name="specialdetails1"></a><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>Geometry</b>. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
- are estimated using the full covariance matrix. The cell e.s.d.'s are taken
- into account individually in the estimation of e.s.d.'s in distances, angles
- and torsion angles; correlations between e.s.d.'s in cell parameters are only
- used when they are defined by crystal symmetry. An approximate (isotropic)
- treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
- planes.</p></td></tr>
- <tr><td class="tabledata"><p><b>Refinement</b>. Refinement of <i>F</i><sup>2</sup> against ALL reflections. The weighted <i>R</i>-factor
- <i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i><sup>2</sup>, conventional
- <i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
- negative <i>F</i><sup>2</sup>. The threshold expression of <i>F</i><sup>2</sup> >
- <span style="font-family:Times">σ</span>(<i>F</i><sup>2</sup>) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
- and is not relevant to the choice of reflections for refinement.
- <i>R</i>-factors based on <i>F</i><sup>2</sup> are statistically about twice as large
- as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
- even larger.</p></td></tr></table>
- </div>
- </div>
- <!-- endspecialdetailsdiv -->
- <div class="tablewrapcoords">
- <a name="fractionalatomiccoordinates1"></a> <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><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" ></td></tr><tr><td class="tabledata" >C1</td><td class="tabledata" >0.3694 (2)</td><td class="tabledata" >0.52612 (6)</td><td class="tabledata" >0.2758 (3)</td><td class="tabledata" >0.0531 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C2</td><td class="tabledata" >0.4692 (2)</td><td class="tabledata" >0.54418 (6)</td><td class="tabledata" >0.1976 (3)</td><td class="tabledata" >0.0587 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2</td><td class="tabledata" >0.5427</td><td class="tabledata" >0.5308</td><td class="tabledata" >0.1793</td><td class="tabledata" >0.070*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C3</td><td class="tabledata" >0.2592 (2)</td><td class="tabledata" >0.54512 (6)</td><td class="tabledata" >0.3021 (3)</td><td class="tabledata" >0.0575 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H3</td><td class="tabledata" >0.1926</td><td class="tabledata" >0.5326</td><td class="tabledata" >0.3541</td><td class="tabledata" >0.069*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C4</td><td class="tabledata" >0.4590 (2)</td><td class="tabledata" >0.58237 (6)</td><td class="tabledata" >0.1467 (3)</td><td class="tabledata" >0.0528 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H4</td><td class="tabledata" >0.5259</td><td class="tabledata" >0.5949</td><td class="tabledata" >0.0950</td><td class="tabledata" >0.063*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C5</td><td class="tabledata" >0.2486 (2)</td><td class="tabledata" >0.58278 (6)</td><td class="tabledata" >0.2507 (3)</td><td class="tabledata" >0.0556 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H5</td><td class="tabledata" >0.1743</td><td class="tabledata" >0.5957</td><td class="tabledata" >0.2676</td><td class="tabledata" >0.067*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C6</td><td class="tabledata" >0.3483 (2)</td><td class="tabledata" >0.60180 (6)</td><td class="tabledata" >0.1735 (3)</td><td class="tabledata" >0.0468 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C7</td><td class="tabledata" >0.4269 (2)</td><td class="tabledata" >0.66196 (6)</td><td class="tabledata" >0.0598 (3)</td><td class="tabledata" >0.0540 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H7A</td><td class="tabledata" >0.4487</td><td class="tabledata" >0.6531</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0571</td><td class="tabledata" >0.065*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H7B</td><td class="tabledata" >0.4994</td><td class="tabledata" >0.6600</td><td class="tabledata" >0.1346</td><td class="tabledata" >0.065*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C8</td><td class="tabledata" >0.3816 (2)</td><td class="tabledata" >0.70308 (6)</td><td class="tabledata" >0.0527 (3)</td><td class="tabledata" >0.0577 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8A</td><td class="tabledata" >0.3102</td><td class="tabledata" >0.7046</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0244</td><td class="tabledata" >0.069*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H8B</td><td class="tabledata" >0.3558</td><td class="tabledata" >0.7110</td><td class="tabledata" >0.1695</td><td class="tabledata" >0.069*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C9</td><td class="tabledata" >0.4804 (2)</td><td class="tabledata" >0.73000 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0131 (3)</td><td class="tabledata" >0.0539 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9A</td><td class="tabledata" >0.5580</td><td class="tabledata" >0.7249</td><td class="tabledata" >0.0468</td><td class="tabledata" >0.065*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H9B</td><td class="tabledata" >0.4929</td><td class="tabledata" >0.7264</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1384</td><td class="tabledata" >0.065*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C10</td><td class="tabledata" >0.5238 (2)</td><td class="tabledata" >0.79809 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0124 (3)</td><td class="tabledata" >0.0459 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C11</td><td class="tabledata" >0.6378 (2)</td><td class="tabledata" >0.79332 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0955 (3)</td><td class="tabledata" >0.0507 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H11</td><td class="tabledata" >0.6630</td><td class="tabledata" >0.7690</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1311</td><td class="tabledata" >0.061*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C12</td><td class="tabledata" >0.4878 (2)</td><td class="tabledata" >0.83474 (6)</td><td class="tabledata" >0.0389 (3)</td><td class="tabledata" >0.0493 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H12</td><td class="tabledata" >0.4117</td><td class="tabledata" >0.8383</td><td class="tabledata" >0.0935</td><td class="tabledata" >0.059*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C13</td><td class="tabledata" >0.7136 (2)</td><td class="tabledata" >0.82491 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1252 (3)</td><td class="tabledata" >0.0534 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H13</td><td class="tabledata" >0.7894</td><td class="tabledata" >0.8214</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1808</td><td class="tabledata" >0.064*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C14</td><td class="tabledata" >0.5645 (2)</td><td class="tabledata" >0.86604 (6)</td><td class="tabledata" >0.0094 (3)</td><td class="tabledata" >0.0512 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H14</td><td class="tabledata" >0.5393</td><td class="tabledata" >0.8903</td><td class="tabledata" >0.0455</td><td class="tabledata" >0.061*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >C15</td><td class="tabledata" >0.6788 (2)</td><td class="tabledata" >0.86171 (6)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0736 (3)</td><td class="tabledata" >0.0487 (5)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >N1</td><td class="tabledata" >0.3792 (2)</td><td class="tabledata" >0.48636 (6)</td><td class="tabledata" >0.3322 (3)</td><td class="tabledata" >0.0763 (7)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >N2</td><td class="tabledata" >0.75855 (17)</td><td class="tabledata" >0.89324 (5)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0993 (3)</td><td class="tabledata" >0.0694 (6)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2A</td><td class="tabledata" >0.8298</td><td class="tabledata" >0.8898</td><td class="tabledata" ><span style="font-family:Times">−</span>0.1474</td><td class="tabledata" >0.083*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >H2B</td><td class="tabledata" >0.7361</td><td class="tabledata" >0.9159</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0669</td><td class="tabledata" >0.083*</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O1</td><td class="tabledata" >0.29183 (19)</td><td class="tabledata" >0.47143 (5)</td><td class="tabledata" >0.4107 (3)</td><td class="tabledata" >0.1127 (8)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O2</td><td class="tabledata" >0.4737 (2)</td><td class="tabledata" >0.46834 (5)</td><td class="tabledata" >0.3007 (4)</td><td class="tabledata" >0.1200 (9)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O3</td><td class="tabledata" >0.32733 (13)</td><td class="tabledata" >0.63919 (4)</td><td class="tabledata" >0.1305 (2)</td><td class="tabledata" >0.0590 (4)</td><td class="tabledata" ></td></tr><tr><td class="tabledata" >O4</td><td class="tabledata" >0.44110 (13)</td><td class="tabledata" >0.76862 (4)</td><td class="tabledata" >0.0214 (2)</td><td class="tabledata" >0.0570 (4)</td><td class="tabledata" ></td></tr></table>
- </div>
- <!-- endtablewrapcoordsdiv -->
- <div class="tablewrapadps">
- <a name="atomicdisplacement1"></a> <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><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" >C1</td><td class="tabledata" >0.0549 (15)</td><td class="tabledata" >0.0357 (14)</td><td class="tabledata" >0.0687 (15)</td><td class="tabledata" >0.0006 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0019 (12)</td><td class="tabledata" >0.0067 (11)</td></tr><tr><td class="tabledata" >C2</td><td class="tabledata" >0.0491 (15)</td><td class="tabledata" >0.0477 (15)</td><td class="tabledata" >0.0793 (17)</td><td class="tabledata" >0.0004 (12)</td><td class="tabledata" >0.0011 (12)</td><td class="tabledata" >0.0025 (12)</td></tr><tr><td class="tabledata" >C3</td><td class="tabledata" >0.0561 (16)</td><td class="tabledata" >0.0499 (15)</td><td class="tabledata" >0.0664 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0045 (12)</td><td class="tabledata" >0.0055 (12)</td><td class="tabledata" >0.0072 (12)</td></tr><tr><td class="tabledata" >C4</td><td class="tabledata" >0.0490 (14)</td><td class="tabledata" >0.0455 (14)</td><td class="tabledata" >0.0640 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0046 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0003 (11)</td><td class="tabledata" >0.0053 (11)</td></tr><tr><td class="tabledata" >C5</td><td class="tabledata" >0.0505 (15)</td><td class="tabledata" >0.0487 (15)</td><td class="tabledata" >0.0677 (15)</td><td class="tabledata" >0.0011 (12)</td><td class="tabledata" >0.0070 (12)</td><td class="tabledata" >0.0050 (12)</td></tr><tr><td class="tabledata" >C6</td><td class="tabledata" >0.0545 (14)</td><td class="tabledata" >0.0361 (13)</td><td class="tabledata" >0.0496 (13)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0013 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0073 (11)</td><td class="tabledata" >0.0021 (10)</td></tr><tr><td class="tabledata" >C7</td><td class="tabledata" >0.0594 (15)</td><td class="tabledata" >0.0428 (14)</td><td class="tabledata" >0.0598 (14)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0065 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0049 (12)</td><td class="tabledata" >0.0052 (10)</td></tr><tr><td class="tabledata" >C8</td><td class="tabledata" >0.0602 (15)</td><td class="tabledata" >0.0445 (14)</td><td class="tabledata" >0.0684 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0038 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0088 (12)</td><td class="tabledata" >0.0069 (11)</td></tr><tr><td class="tabledata" >C9</td><td class="tabledata" >0.0666 (16)</td><td class="tabledata" >0.0383 (13)</td><td class="tabledata" >0.0566 (14)</td><td class="tabledata" >0.0025 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0009 (11)</td><td class="tabledata" >0.0040 (10)</td></tr><tr><td class="tabledata" >C10</td><td class="tabledata" >0.0493 (14)</td><td class="tabledata" >0.0380 (13)</td><td class="tabledata" >0.0504 (12)</td><td class="tabledata" >0.0008 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0028 (10)</td><td class="tabledata" >0.0031 (10)</td></tr><tr><td class="tabledata" >C11</td><td class="tabledata" >0.0524 (14)</td><td class="tabledata" >0.0404 (13)</td><td class="tabledata" >0.0594 (14)</td><td class="tabledata" >0.0082 (11)</td><td class="tabledata" >0.0000 (12)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0023 (10)</td></tr><tr><td class="tabledata" >C12</td><td class="tabledata" >0.0513 (14)</td><td class="tabledata" >0.0453 (14)</td><td class="tabledata" >0.0514 (13)</td><td class="tabledata" >0.0054 (11)</td><td class="tabledata" >0.0031 (10)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0005 (10)</td></tr><tr><td class="tabledata" >C13</td><td class="tabledata" >0.0493 (14)</td><td class="tabledata" >0.0524 (15)</td><td class="tabledata" >0.0584 (14)</td><td class="tabledata" >0.0026 (11)</td><td class="tabledata" >0.0019 (11)</td><td class="tabledata" >0.0001 (11)</td></tr><tr><td class="tabledata" >C14</td><td class="tabledata" >0.0615 (15)</td><td class="tabledata" >0.0391 (13)</td><td class="tabledata" >0.0530 (14)</td><td class="tabledata" >0.0025 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0022 (12)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0065 (10)</td></tr><tr><td class="tabledata" >C15</td><td class="tabledata" >0.0500 (14)</td><td class="tabledata" >0.0465 (14)</td><td class="tabledata" >0.0495 (12)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0027 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0038 (11)</td><td class="tabledata" >0.0005 (10)</td></tr><tr><td class="tabledata" >N1</td><td class="tabledata" >0.0723 (17)</td><td class="tabledata" >0.0485 (15)</td><td class="tabledata" >0.1081 (18)</td><td class="tabledata" >0.0008 (12)</td><td class="tabledata" >0.0043 (14)</td><td class="tabledata" >0.0138 (12)</td></tr><tr><td class="tabledata" >N2</td><td class="tabledata" >0.0672 (13)</td><td class="tabledata" >0.0544 (13)</td><td class="tabledata" >0.0867 (15)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0160 (11)</td><td class="tabledata" >0.0080 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0116 (11)</td></tr><tr><td class="tabledata" >O1</td><td class="tabledata" >0.0956 (16)</td><td class="tabledata" >0.0661 (13)</td><td class="tabledata" >0.176 (2)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0062 (11)</td><td class="tabledata" >0.0244 (15)</td><td class="tabledata" >0.0501 (13)</td></tr><tr><td class="tabledata" >O2</td><td class="tabledata" >0.0921 (15)</td><td class="tabledata" >0.0634 (14)</td><td class="tabledata" >0.205 (3)</td><td class="tabledata" >0.0244 (12)</td><td class="tabledata" >0.0344 (16)</td><td class="tabledata" >0.0389 (14)</td></tr><tr><td class="tabledata" >O3</td><td class="tabledata" >0.0557 (9)</td><td class="tabledata" >0.0410 (9)</td><td class="tabledata" >0.0805 (11)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0021 (7)</td><td class="tabledata" ><span style="font-family:Times">−</span>0.0004 (8)</td><td class="tabledata" >0.0110 (8)</td></tr><tr><td class="tabledata" >O4</td><td class="tabledata" >0.0583 (10)</td><td class="tabledata" >0.0381 (9)</td><td class="tabledata" >0.0745 (11)</td><td class="tabledata" >0.0006 (8)</td><td class="tabledata" >0.0061 (8)</td><td class="tabledata" >0.0040 (7)</td></tr></table>
- </div>
- <!-- endtablewrapadpsdiv -->
- <div class="tablewrapgeomlong">
- <a name="geometricparameters1"></a> <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>
- <col width="20%"></col>
- <col width="30%"></col>
- <col width="20%"></col>
- </colgroup>
- <tr><td width="30%" class="tabledata" >C1—C3</td><td width="20%" class="tabledata" >1.377 (3)</td><td width="30%" class="tabledata" >C9—O4</td><td width="20%" class="tabledata" >1.433 (2)</td></tr><tr><td width="30%" class="tabledata" >C1—C2</td><td width="20%" class="tabledata" >1.383 (3)</td><td width="30%" class="tabledata" >C9—H9A</td><td width="20%" class="tabledata" >0.9700</td></tr><tr><td width="30%" class="tabledata" >C1—N1</td><td width="20%" class="tabledata" >1.453 (3)</td><td width="30%" class="tabledata" >C9—H9B</td><td width="20%" class="tabledata" >0.9700</td></tr><tr><td width="30%" class="tabledata" >C2—C4</td><td width="20%" class="tabledata" >1.388 (3)</td><td width="30%" class="tabledata" >C10—O4</td><td width="20%" class="tabledata" >1.385 (2)</td></tr><tr><td width="30%" class="tabledata" >C2—H2</td><td width="20%" class="tabledata" >0.9300</td><td width="30%" class="tabledata" >C10—C12</td><td width="20%" class="tabledata" >1.389 (3)</td></tr><tr><td width="30%" class="tabledata" >C3—C5</td><td width="20%" class="tabledata" >1.372 (3)</td><td width="30%" class="tabledata" >C10—C11</td><td width="20%" class="tabledata" >1.393 (3)</td></tr><tr><td width="30%" class="tabledata" >C3—H3</td><td width="20%" class="tabledata" >0.9300</td><td width="30%" class="tabledata" >C11—C13</td><td width="20%" class="tabledata" >1.390 (3)</td></tr><tr><td width="30%" class="tabledata" >C4—C6</td><td width="20%" class="tabledata" >1.390 (3)</td><td width="30%" class="tabledata" >C11—H11</td><td width="20%" class="tabledata" >0.9300</td></tr><tr><td width="30%" class="tabledata" >C4—H4</td><td width="20%" class="tabledata" >0.9300</td><td width="30%" class="tabledata" >C12—C14</td><td width="20%" class="tabledata" >1.387 (3)</td></tr><tr><td width="30%" class="tabledata" >C5—C6</td><td width="20%" class="tabledata" >1.394 (3)</td><td width="30%" class="tabledata" >C12—H12</td><td width="20%" class="tabledata" >0.9300</td></tr><tr><td width="30%" class="tabledata" >C5—H5</td><td width="20%" class="tabledata" >0.9300</td><td width="30%" class="tabledata" >C13—C15</td><td width="20%" class="tabledata" >1.391 (3)</td></tr><tr><td width="30%" class="tabledata" >C6—O3</td><td width="20%" class="tabledata" >1.361 (3)</td><td width="30%" class="tabledata" >C13—H13</td><td width="20%" class="tabledata" >0.9300</td></tr><tr><td width="30%" class="tabledata" >C7—O3</td><td width="20%" class="tabledata" >1.440 (2)</td><td width="30%" class="tabledata" >C14—C15</td><td width="20%" class="tabledata" >1.394 (3)</td></tr><tr><td width="30%" class="tabledata" >C7—C8</td><td width="20%" class="tabledata" >1.513 (3)</td><td width="30%" class="tabledata" >C14—H14</td><td width="20%" class="tabledata" >0.9300</td></tr><tr><td width="30%" class="tabledata" >C7—H7A</td><td width="20%" class="tabledata" >0.9700</td><td width="30%" class="tabledata" >C15—N2</td><td width="20%" class="tabledata" >1.409 (3)</td></tr><tr><td width="30%" class="tabledata" >C7—H7B</td><td width="20%" class="tabledata" >0.9700</td><td width="30%" class="tabledata" >N1—O2</td><td width="20%" class="tabledata" >1.221 (2)</td></tr><tr><td width="30%" class="tabledata" >C8—C9</td><td width="20%" class="tabledata" >1.506 (3)</td><td width="30%" class="tabledata" >N1—O1</td><td width="20%" class="tabledata" >1.232 (3)</td></tr><tr><td width="30%" class="tabledata" >C8—H8A</td><td width="20%" class="tabledata" >0.9700</td><td width="30%" class="tabledata" >N2—H2A</td><td width="20%" class="tabledata" >0.8600</td></tr><tr><td width="30%" class="tabledata" >C8—H8B</td><td width="20%" class="tabledata" >0.9700</td><td width="30%" class="tabledata" >N2—H2B</td><td width="20%" class="tabledata" >0.8600</td></tr><tr><td width="25%" class="tabledata" ></td><td width="25%" class="tabledata" ></td><td width="25%" class="tabledata" ></td><td width="25%" class="tabledata" ></td></tr><tr><td width="30%" class="tabledata" >C3—C1—C2</td><td width="20%" class="tabledata" >121.3 (2)</td><td width="30%" class="tabledata" >O4—C9—H9A</td><td width="20%" class="tabledata" >110.1</td></tr><tr><td width="30%" class="tabledata" >C3—C1—N1</td><td width="20%" class="tabledata" >118.6 (2)</td><td width="30%" class="tabledata" >C8—C9—H9A</td><td width="20%" class="tabledata" >110.1</td></tr><tr><td width="30%" class="tabledata" >C2—C1—N1</td><td width="20%" class="tabledata" >120.1 (2)</td><td width="30%" class="tabledata" >O4—C9—H9B</td><td width="20%" class="tabledata" >110.1</td></tr><tr><td width="30%" class="tabledata" >C1—C2—C4</td><td width="20%" class="tabledata" >119.5 (2)</td><td width="30%" class="tabledata" >C8—C9—H9B</td><td width="20%" class="tabledata" >110.1</td></tr><tr><td width="30%" class="tabledata" >C1—C2—H2</td><td width="20%" class="tabledata" >120.2</td><td width="30%" class="tabledata" >H9A—C9—H9B</td><td width="20%" class="tabledata" >108.4</td></tr><tr><td width="30%" class="tabledata" >C4—C2—H2</td><td width="20%" class="tabledata" >120.2</td><td width="30%" class="tabledata" >O4—C10—C12</td><td width="20%" class="tabledata" >116.53 (19)</td></tr><tr><td width="30%" class="tabledata" >C5—C3—C1</td><td width="20%" class="tabledata" >119.3 (2)</td><td width="30%" class="tabledata" >O4—C10—C11</td><td width="20%" class="tabledata" >124.51 (19)</td></tr><tr><td width="30%" class="tabledata" >C5—C3—H3</td><td width="20%" class="tabledata" >120.4</td><td width="30%" class="tabledata" >C12—C10—C11</td><td width="20%" class="tabledata" >119.0 (2)</td></tr><tr><td width="30%" class="tabledata" >C1—C3—H3</td><td width="20%" class="tabledata" >120.4</td><td width="30%" class="tabledata" >C13—C11—C10</td><td width="20%" class="tabledata" >120.0 (2)</td></tr><tr><td width="30%" class="tabledata" >C2—C4—C6</td><td width="20%" class="tabledata" >119.6 (2)</td><td width="30%" class="tabledata" >C13—C11—H11</td><td width="20%" class="tabledata" >120.0</td></tr><tr><td width="30%" class="tabledata" >C2—C4—H4</td><td width="20%" class="tabledata" >120.2</td><td width="30%" class="tabledata" >C10—C11—H11</td><td width="20%" class="tabledata" >120.0</td></tr><tr><td width="30%" class="tabledata" >C6—C4—H4</td><td width="20%" class="tabledata" >120.2</td><td width="30%" class="tabledata" >C14—C12—C10</td><td width="20%" class="tabledata" >120.5 (2)</td></tr><tr><td width="30%" class="tabledata" >C3—C5—C6</td><td width="20%" class="tabledata" >120.6 (2)</td><td width="30%" class="tabledata" >C14—C12—H12</td><td width="20%" class="tabledata" >119.7</td></tr><tr><td width="30%" class="tabledata" >C3—C5—H5</td><td width="20%" class="tabledata" >119.7</td><td width="30%" class="tabledata" >C10—C12—H12</td><td width="20%" class="tabledata" >119.7</td></tr><tr><td width="30%" class="tabledata" >C6—C5—H5</td><td width="20%" class="tabledata" >119.7</td><td width="30%" class="tabledata" >C11—C13—C15</td><td width="20%" class="tabledata" >121.5 (2)</td></tr><tr><td width="30%" class="tabledata" >O3—C6—C4</td><td width="20%" class="tabledata" >124.99 (19)</td><td width="30%" class="tabledata" >C11—C13—H13</td><td width="20%" class="tabledata" >119.3</td></tr><tr><td width="30%" class="tabledata" >O3—C6—C5</td><td width="20%" class="tabledata" >115.26 (19)</td><td width="30%" class="tabledata" >C15—C13—H13</td><td width="20%" class="tabledata" >119.3</td></tr><tr><td width="30%" class="tabledata" >C4—C6—C5</td><td width="20%" class="tabledata" >119.8 (2)</td><td width="30%" class="tabledata" >C12—C14—C15</td><td width="20%" class="tabledata" >121.17 (19)</td></tr><tr><td width="30%" class="tabledata" >O3—C7—C8</td><td width="20%" class="tabledata" >106.95 (18)</td><td width="30%" class="tabledata" >C12—C14—H14</td><td width="20%" class="tabledata" >119.4</td></tr><tr><td width="30%" class="tabledata" >O3—C7—H7A</td><td width="20%" class="tabledata" >110.3</td><td width="30%" class="tabledata" >C15—C14—H14</td><td width="20%" class="tabledata" >119.4</td></tr><tr><td width="30%" class="tabledata" >C8—C7—H7A</td><td width="20%" class="tabledata" >110.3</td><td width="30%" class="tabledata" >C13—C15—C14</td><td width="20%" class="tabledata" >117.81 (19)</td></tr><tr><td width="30%" class="tabledata" >O3—C7—H7B</td><td width="20%" class="tabledata" >110.3</td><td width="30%" class="tabledata" >C13—C15—N2</td><td width="20%" class="tabledata" >120.8 (2)</td></tr><tr><td width="30%" class="tabledata" >C8—C7—H7B</td><td width="20%" class="tabledata" >110.3</td><td width="30%" class="tabledata" >C14—C15—N2</td><td width="20%" class="tabledata" >121.4 (2)</td></tr><tr><td width="30%" class="tabledata" >H7A—C7—H7B</td><td width="20%" class="tabledata" >108.6</td><td width="30%" class="tabledata" >O2—N1—O1</td><td width="20%" class="tabledata" >121.3 (2)</td></tr><tr><td width="30%" class="tabledata" >C9—C8—C7</td><td width="20%" class="tabledata" >111.73 (19)</td><td width="30%" class="tabledata" >O2—N1—C1</td><td width="20%" class="tabledata" >119.5 (2)</td></tr><tr><td width="30%" class="tabledata" >C9—C8—H8A</td><td width="20%" class="tabledata" >109.3</td><td width="30%" class="tabledata" >O1—N1—C1</td><td width="20%" class="tabledata" >119.2 (2)</td></tr><tr><td width="30%" class="tabledata" >C7—C8—H8A</td><td width="20%" class="tabledata" >109.3</td><td width="30%" class="tabledata" >C15—N2—H2A</td><td width="20%" class="tabledata" >120.0</td></tr><tr><td width="30%" class="tabledata" >C9—C8—H8B</td><td width="20%" class="tabledata" >109.3</td><td width="30%" class="tabledata" >C15—N2—H2B</td><td width="20%" class="tabledata" >120.0</td></tr><tr><td width="30%" class="tabledata" >C7—C8—H8B</td><td width="20%" class="tabledata" >109.3</td><td width="30%" class="tabledata" >H2A—N2—H2B</td><td width="20%" class="tabledata" >120.0</td></tr><tr><td width="30%" class="tabledata" >H8A—C8—H8B</td><td width="20%" class="tabledata" >107.9</td><td width="30%" class="tabledata" >C6—O3—C7</td><td width="20%" class="tabledata" >119.42 (17)</td></tr><tr><td width="30%" class="tabledata" >O4—C9—C8</td><td width="20%" class="tabledata" >108.19 (18)</td><td width="30%" class="tabledata" >C10—O4—C9</td><td width="20%" class="tabledata" >117.95 (17)</td></tr><tr><td width="25%" class="tabledata" ></td><td width="25%" class="tabledata" ></td><td width="25%" class="tabledata" ></td><td width="25%" class="tabledata" ></td></tr><tr><td width="30%" class="tabledata" >C3—C1—C2—C4</td><td width="20%" class="tabledata" >0.9 (3)</td><td width="30%" class="tabledata" >C10—C11—C13—C15</td><td width="20%" class="tabledata" >0.0 (3)</td></tr><tr><td width="30%" class="tabledata" >N1—C1—C2—C4</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>179.1 (2)</td><td width="30%" class="tabledata" >C10—C12—C14—C15</td><td width="20%" class="tabledata" >0.6 (3)</td></tr><tr><td width="30%" class="tabledata" >C2—C1—C3—C5</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>0.4 (4)</td><td width="30%" class="tabledata" >C11—C13—C15—C14</td><td width="20%" class="tabledata" >0.0 (3)</td></tr><tr><td width="30%" class="tabledata" >N1—C1—C3—C5</td><td width="20%" class="tabledata" >179.5 (2)</td><td width="30%" class="tabledata" >C11—C13—C15—N2</td><td width="20%" class="tabledata" >177.85 (19)</td></tr><tr><td width="30%" class="tabledata" >C1—C2—C4—C6</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>0.6 (3)</td><td width="30%" class="tabledata" >C12—C14—C15—C13</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>0.3 (3)</td></tr><tr><td width="30%" class="tabledata" >C1—C3—C5—C6</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>0.3 (3)</td><td width="30%" class="tabledata" >C12—C14—C15—N2</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>178.14 (19)</td></tr><tr><td width="30%" class="tabledata" >C2—C4—C6—O3</td><td width="20%" class="tabledata" >179.49 (19)</td><td width="30%" class="tabledata" >C3—C1—N1—O2</td><td width="20%" class="tabledata" >175.7 (2)</td></tr><tr><td width="30%" class="tabledata" >C2—C4—C6—C5</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>0.1 (3)</td><td width="30%" class="tabledata" >C2—C1—N1—O2</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>4.4 (4)</td></tr><tr><td width="30%" class="tabledata" >C3—C5—C6—O3</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>179.1 (2)</td><td width="30%" class="tabledata" >C3—C1—N1—O1</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>4.1 (4)</td></tr><tr><td width="30%" class="tabledata" >C3—C5—C6—C4</td><td width="20%" class="tabledata" >0.6 (3)</td><td width="30%" class="tabledata" >C2—C1—N1—O1</td><td width="20%" class="tabledata" >175.8 (2)</td></tr><tr><td width="30%" class="tabledata" >O3—C7—C8—C9</td><td width="20%" class="tabledata" >177.80 (17)</td><td width="30%" class="tabledata" >C4—C6—O3—C7</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>3.4 (3)</td></tr><tr><td width="30%" class="tabledata" >C7—C8—C9—O4</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>167.07 (17)</td><td width="30%" class="tabledata" >C5—C6—O3—C7</td><td width="20%" class="tabledata" >176.24 (18)</td></tr><tr><td width="30%" class="tabledata" >O4—C10—C11—C13</td><td width="20%" class="tabledata" >179.26 (19)</td><td width="30%" class="tabledata" >C8—C7—O3—C6</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>171.25 (17)</td></tr><tr><td width="30%" class="tabledata" >C12—C10—C11—C13</td><td width="20%" class="tabledata" >0.3 (3)</td><td width="30%" class="tabledata" >C12—C10—O4—C9</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>173.68 (17)</td></tr><tr><td width="30%" class="tabledata" >O4—C10—C12—C14</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>179.64 (18)</td><td width="30%" class="tabledata" >C11—C10—O4—C9</td><td width="20%" class="tabledata" >7.3 (3)</td></tr><tr><td width="30%" class="tabledata" >C11—C10—C12—C14</td><td width="20%" class="tabledata" ><span style="font-family:Times">−</span>0.6 (3)</td><td width="30%" class="tabledata" >C8—C9—O4—C10</td><td width="20%" class="tabledata" >173.62 (17)</td></tr></table>
- </div>
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- <div class="tablewraphbondslong">
- <a name="hydrogen-bondgeometry1"></a> <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">
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- <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" >N2—H2B···O1<sup>i</sup></td><td width="15%" class="tabledata" >0.86</td><td width="15%" class="tabledata" >2.29</td><td width="15%" class="tabledata" >3.123 (3)</td><td width="15%" class="tabledata" >164</td></tr><tr><td width="40%" class="tabledata" >C3—H3···Cg1<sup>ii</sup></td><td width="15%" class="tabledata" >0.93</td><td width="15%" class="tabledata" >3.07</td><td width="15%" class="tabledata" >3.513 (4)</td><td width="15%" class="tabledata" >111</td></tr><tr><td width="40%" class="tabledata" >C7—H7B···Cg2<sup>iii</sup></td><td width="15%" class="tabledata" >0.97</td><td width="15%" class="tabledata" >2.71</td><td width="15%" class="tabledata" >3.567 (4)</td><td width="15%" class="tabledata" >148</td></tr><tr><td width="40%" class="tabledata" >C13—H13···Cg2<sup>iv</sup></td><td width="15%" class="tabledata" >0.93</td><td width="15%" class="tabledata" >3.01</td><td width="15%" class="tabledata" >3.757 (4)</td><td width="15%" class="tabledata" >139</td></tr></table><table style="table-layout:fixed" width="100%" class="noborder"><tr><td class="tabledata" >Symmetry codes: (i) −<i>x</i>+1, <i>y</i>+1/2, −<i>z</i>+1/2; (ii) −<i>x</i>+1/2, <i>y</i>, <i>z</i>−3/2; (iii) <i>x</i>, −<i>y</i>−1/2, <i>z</i>−3/2; (iv) −<i>x</i>−1/2, <i>y</i>, <i>z</i>−1/2.</td></tr></table>
- </div>
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- <div class="tablewraphbondsshort">
- <a name="hydrogen-bondgeometry1"></a> <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">
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- <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" >N2—H2B···O1<sup>i</sup></td><td width="15%" class="tabledata" >0.86</td><td width="15%" class="tabledata" >2.29</td><td width="15%" class="tabledata" >3.123 (3)</td><td width="15%" class="tabledata" >164</td></tr><tr><td width="40%" class="tabledata" >C3—H3···Cg1<sup>ii</sup></td><td width="15%" class="tabledata" >0.93</td><td width="15%" class="tabledata" >3.07</td><td width="15%" class="tabledata" >3.513 (4)</td><td width="15%" class="tabledata" >111</td></tr><tr><td width="40%" class="tabledata" >C7—H7B···Cg2<sup>iii</sup></td><td width="15%" class="tabledata" >0.97</td><td width="15%" class="tabledata" >2.71</td><td width="15%" class="tabledata" >3.567 (4)</td><td width="15%" class="tabledata" >148</td></tr><tr><td width="40%" class="tabledata" >C13—H13···Cg2<sup>iv</sup></td><td width="15%" class="tabledata" >0.93</td><td width="15%" class="tabledata" >3.01</td><td width="15%" class="tabledata" >3.757 (4)</td><td width="15%" class="tabledata" >139</td></tr></table><table style="table-layout:fixed" width="100%" class="noborder"><tr><td class="tabledata" >Symmetry codes: (i) −<i>x</i>+1, <i>y</i>+1/2, −<i>z</i>+1/2; (ii) −<i>x</i>+1/2, <i>y</i>, <i>z</i>−3/2; (iii) <i>x</i>, −<i>y</i>−1/2, <i>z</i>−3/2; (iv) −<i>x</i>−1/2, <i>y</i>, <i>z</i>−1/2.</td></tr></table>
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- <div class="acknowledgements">
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- Acknowledgements <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
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- <!-- endheading2div --><p>We acknowledge the support of the National Natural Science Foundation of China
- (No. 20662003) and the Foundation of the Governor of Guizhou Province, China.</p>
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- <div class="references">
- <a name="references"></a><a class="buttons" title="link to reference list" href="./at2638bdy.html#References">references</a>
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- References <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan -->
- </div>
- <!-- endheading2div --><p>Bruker, (2005). <i>APEX2</i>, <i>SAINT</i> and <i>SADABS</i>. Bruker AXS Inc., Madison, Wisconsin, USA.<br /><br />Day, A. I. & Arnold, A. P. (2000). World Patent No. WO/2000/068 232.<br /><br />Day, A. I., Blanch, R. J., Arnold, A. P., Lorenzo, S., Lewis, G. R. & Dance, I. (2002). <i>Angew. Chem. Int. Ed.</i> <b>41</b>, 275–277.<br /><br />Farrugia, L. J. (1997). <i>J. Appl. Cryst.</i> <b>30</b>, 565.<br /><br />Farrugia, L. J. (1999). <i>J. Appl. Cryst.</i> <b>32</b>, 837–838.<br /><br />Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). <i>J. Am. Chem. Soc.</i> <b>103</b>, 7367–7368.<br /><br />Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K. & Kim, K. (2000). <i>J. Am. Chem. Soc.</i> <b>122</b>, 540–541.<br /><br />Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>, 112–122.<br /><br /></p>
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