MersV1, Pmc, Checkpoint, bibRecord, 001109

Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-d:6,5-d′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate

Identifieur interne : 001109 ( Pmc/Checkpoint ); précédent : 001108; suivant : 001110

Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-d:6,5-d′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate

Source :

Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2014.

RBID : PMC:4257167

Abstract

In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257167

DOI: 10.1107/S1600536814020200
PubMed: 25484655
PubMed Central: 4257167

Affiliations:

Arménie

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Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>
:6,5-<italic>d</italic>
′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate</title>
<author><name sortKey="Ayvazyan, Armen" sort="Ayvazyan, Armen" uniqKey="Ayvazyan A" first="Armen" last="Ayvazyan">Armen Ayvazyan</name>
<affiliation wicri:level="1"><nlm:aff id="a">Molecule Structure Research Center of, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences Republic of Armenia, Azatutyan ave. 26, Yerevan 0014,<country>Armenia</country>
</nlm:aff>
<country xml:lang="fr">Arménie</country>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>
:6,5-<italic>d</italic>
′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate</title>
<author><name sortKey="Ayvazyan, Armen" sort="Ayvazyan, Armen" uniqKey="Ayvazyan A" first="Armen" last="Ayvazyan">Armen Ayvazyan</name>
<affiliation wicri:level="1"><nlm:aff id="a">Molecule Structure Research Center of, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences Republic of Armenia, Azatutyan ave. 26, Yerevan 0014,<country>Armenia</country>
</nlm:aff>
<country xml:lang="fr">Arménie</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title>
<idno type="eISSN">1600-5368</idno>
<imprint><date when="2014">2014</date>
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</series>
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<front><div type="abstract" xml:lang="en"><p>In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
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<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
  <front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id>
<journal-id journal-id-type="iso-abbrev">Acta Crystallogr Sect E Struct Rep Online</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title>
</journal-title-group>
<issn pub-type="epub">1600-5368</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">25484655</article-id>
<article-id pub-id-type="pmc">4257167</article-id>
<article-id pub-id-type="publisher-id">hb7283</article-id>
<article-id pub-id-type="doi">10.1107/S1600536814020200</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536814020200</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject>
</subj-group>
</article-categories>
<title-group><article-title>Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>
:6,5-<italic>d</italic>
′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate</article-title>
<alt-title><italic>2C<sub>20</sub>
H<sub>18</sub>
N<sub>6</sub>
O<sub>5</sub>
·C<sub>3</sub>
H<sub>7</sub>
NO</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Ayvazyan</surname>
<given-names>Armen</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<aff id="a"><label>a</label>
Molecule Structure Research Center of, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences Republic of Armenia, Azatutyan ave. 26, Yerevan 0014,<country>Armenia</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>armen@msrc.am</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>10</month>
<year>2014</year>
</pub-date>
<pub-date pub-type="epub"><day>17</day>
<month>9</month>
<year>2014</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>17</day>
<month>9</month>
<year>2014</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the 
 							. </pmc-comment>
      <volume>70</volume>
<issue>Pt 10</issue>
<issue-id pub-id-type="publisher-id">e141000</issue-id>
<fpage>213</fpage>
<lpage>215</lpage>
<history><date date-type="received"><day>07</day>
<month>9</month>
<year>2014</year>
</date>
<date date-type="accepted"><day>08</day>
<month>9</month>
<year>2014</year>
</date>
</history>
<permissions><copyright-statement>© Armen Ayvazyan 2014</copyright-statement>
<copyright-year>2014</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits
unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
</license>
</permissions>
<self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536814020200">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract abstract-type="toc"><p>In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry.</p>
</abstract>
<abstract><p>The title compound, C<sub>20</sub>
H<sub>18</sub>
N<sub>6</sub>
O<sub>5</sub>
·0.5C<sub>3</sub>
H<sub>7</sub>
NO, crystallized as a dimethylformamide (DMF) solvate. In the main molecule, the dihedral angle between the pyridodipyrimidine fused-ring system and the benzamide substituent is 82.26 (11)°. In the crystal, the benzamide molecules are linked by N—H⋯O hydrogen bonds to generate tetramers with an approximate square-prismatic shape, which appears to correlate with the tetragonal crystal symmetry. The DMF molecule is disordered about a crystallographic twofold axis and accepts a C—H⋯O interaction from the benzamide molecule.</p>
</abstract>
<kwd-group><kwd>crystal structure</kwd>
<kwd>heterocyclic compounds</kwd>
<kwd>amide</kwd>
<kwd>hydrogen bonding</kwd>
<kwd>tetramer</kwd>
</kwd-group>
</article-meta>
</front>
<floats-group><fig id="fig1" position="float"><label>Figure 1</label>
<caption><p>The molecular structure with thermal displacement ellipsoids drawn at the 50% probability level (H atoms omitted for clarity).</p>
</caption>
<graphic xlink:href="e-70-00213-fig1"></graphic>
</fig>
<fig id="fig2" position="float"><label>Figure 2</label>
<caption><p>Non-classical hydrogen bonding of disordered DMFA solvent molecules with molecules of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>
:6,5-<italic>d</italic>
′]dipyrimidin-5-yl)benzamide related by the twofold axes of the space group.</p>
</caption>
<graphic xlink:href="e-70-00213-fig2"></graphic>
</fig>
<fig id="fig3" position="float"><label>Figure 3</label>
<caption><p>Square-prismatic telomer formed by four 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-<italic>d</italic>
:6,5-<italic>d</italic>
′]dipyrimidin-5-yl)<0.02pt>benzamide molecules <italic>via</italic>
 intermolecular hydrogen bonding.</p>
</caption>
<graphic xlink:href="e-70-00213-fig3"></graphic>
</fig>
<table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (Å, °)</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N23—H23<italic>B</italic>
⋯O31<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.88 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.19 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.003 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">153 (3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N23—H23<italic>A</italic>
⋯O22<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.96 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.09 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.017 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">164 (3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C17—H17⋯O51</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.56</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.313 (10)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">138</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-70-00213-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-70-00213-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table2" position="float"><label>Table 2</label>
<caption><title>Experimental details</title>
</caption>
<table frame="hsides" rules="groups"><tbody valign="top"><tr><td style="" rowspan="1" colspan="2" align="left" valign="top">Crystal data</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2C<sub>20</sub>
H<sub>18</sub>
N<sub>6</sub>
O<sub>5</sub>
·C<sub>3</sub>
H<sub>7</sub>
NO</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic>
<sub>r</sub>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">917.90</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">Tetragonal, <italic>I</italic>
<inline-formula><inline-graphic xlink:href="e-70-00213-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
2<italic>d</italic>
</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">293</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>
, <italic>c</italic>
 (Å)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">26.173 (4), 12.434 (3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic>
 (Å<sup>3</sup>
)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">8517 (3)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">8</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Radiation type</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>
)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.11</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.16 (radius)</td>
</tr>
<tr><td style="" rowspan="1" colspan="2" align="left" valign="top"> </td>
</tr>
<tr><td style="" rowspan="1" colspan="2" align="left" valign="top">Data collection</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">Enraf–Nonius CAD-4</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic>
 > 2σ(<italic>I</italic>
)] reflections</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">6734, 6216, 3247</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
<sub>int</sub>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.015</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub>
 (Å<sup>−1</sup>
)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.703</td>
</tr>
<tr><td style="" rowspan="1" colspan="2" align="left" valign="top"> </td>
</tr>
<tr><td style="" rowspan="1" colspan="2" align="left" valign="top">Refinement</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
 > 2σ(<italic>F</italic>
<sup>2</sup>
)], <italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
), <italic>S</italic>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.056, 0.135, 1.01</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">6216</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">339</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">No. of restraints</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">H atoms treated by a mixture of independent and constrained refinement</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>
, Δρ<sub>min</sub>
 (e Å<sup>−3</sup>
)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.12, −0.17</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Absolute structure</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic>
 determined using 1083 quotients [(<italic>I</italic>
<sup>+</sup>
)−(<italic>I</italic>
<sup>−</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>−</sup>
)] (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb11"> ▶</xref>
)</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">Absolute structure parameter</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.0 (10)</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Computer programs: <italic>CAD-4 Software</italic>
 (Enraf–Nonius, 1988<xref ref-type="bibr" rid="bb5"> ▶</xref>
), <italic>HELENA</italic>
 (Spek, 1997<xref ref-type="bibr" rid="bb14"> ▶</xref>
), <italic>SHELXS2014</italic>
 and <italic>SHELXL2014</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb13"> ▶</xref>
), <italic>ORTEP-3 for Windows</italic>
 (Farrugia, 2012<xref ref-type="bibr" rid="bb7"> ▶</xref>
), <italic>enCIFer</italic>
 (Allen <italic>et al.</italic>
, 2004<xref ref-type="bibr" rid="bb1"> ▶</xref>
) and <italic>publCIF</italic>
 (Westrip, 2010<xref ref-type="bibr" rid="bb15"> ▶</xref>
).</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
<affiliations><list><country><li>Arménie</li>
</country>
</list>
<tree><country name="Arménie"><noRegion><name sortKey="Ayvazyan, Armen" sort="Ayvazyan, Armen" uniqKey="Ayvazyan A" first="Armen" last="Ayvazyan">Armen Ayvazyan</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>

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	Serveur d'exploration MERS
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Serveur d'exploration MERS

Crystal structure of 2-(1,3,7,9-tetra­methyl-2,4,6,8-tetra­oxo-1,2,3,4,6,7,8,9-octa­hydro­pyrido[2,3-d:6,5-d′]dipyrimidin-5-yl)benzamide di­methyl­formamide hemisolvate

Crystal structure of 2-(1,3,7,9-tetra­methyl-2,4,6,8-tetra­oxo-1,2,3,4,6,7,8,9-octa­hydro­pyrido[2,3-d:6,5-d′]dipyrimidin-5-yl)benzamide di­methyl­formamide hemisolvate

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Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-d:6,5-d′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate

Crystal structure of 2-(1,3,7,9-tetramethyl-2,4,6,8-tetraoxo-1,2,3,4,6,7,8,9-octahydropyrido[2,3-d:6,5-d′]dipyrimidin-5-yl)benzamide dimethylformamide hemisolvate