(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanol: a possible metabolite of the synthetic musk fragrance AHTN
Identifieur interne : 001345 ( Pmc/Checkpoint ); précédent : 001344; suivant : 001346(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanol: a possible metabolite of the synthetic musk fragrance AHTN
Auteurs : Rüdiger Faust [Allemagne] ; Djawed Nauroozi [Allemagne] ; Clemens Bruhn [Allemagne] ; Britta Koch [Allemagne] ; Paul Kuhlich [Allemagne] ; Christian Piechotta [Allemagne] ; Irene Nehls [Allemagne]Source :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2011.
Abstract
The title compound (AHTN-OH), C17H26O, was prepared in order to provide standard materials for the qualitative and quantitative analysis of environmental pollutants. The molecule possesses a chiral C atom, although the structure determination was performed on racemic material, expressed in the structure as disordered chiral sites. The asymmetric unit consists of four AHTN-OH molecules containing an hydroxy group and forming a tetrameric cyclic motif built up by four strong hydrogen bonds between these hydroxy groups and additionally by two weak C—H⋯π interactions. Furthermore, these tetramers are linked
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DOI: 10.1107/S1600536811018009
PubMed: 21754834
PubMed Central: 3120335
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanol: a possible metabolite of the synthetic musk fragrance AHTN</title><author><name sortKey="Faust, Rudiger" sort="Faust, Rudiger" uniqKey="Faust R" first="Rüdiger" last="Faust">Rüdiger Faust</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Nauroozi, Djawed" sort="Nauroozi, Djawed" uniqKey="Nauroozi D" first="Djawed" last="Nauroozi">Djawed Nauroozi</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Bruhn, Clemens" sort="Bruhn, Clemens" uniqKey="Bruhn C" first="Clemens" last="Bruhn">Clemens Bruhn</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Koch, Britta" sort="Koch, Britta" uniqKey="Koch B" first="Britta" last="Koch">Britta Koch</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kuhlich, Paul" sort="Kuhlich, Paul" uniqKey="Kuhlich P" first="Paul" last="Kuhlich">Paul Kuhlich</name><affiliation wicri:level="1"><nlm:aff id="b">BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Piechotta, Christian" sort="Piechotta, Christian" uniqKey="Piechotta C" first="Christian" last="Piechotta">Christian Piechotta</name><affiliation wicri:level="1"><nlm:aff id="b">BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Nehls, Irene" sort="Nehls, Irene" uniqKey="Nehls I" first="Irene" last="Nehls">Irene Nehls</name><affiliation wicri:level="1"><nlm:aff id="b">BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21754834</idno><idno type="pmc">3120335</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120335</idno><idno type="RBID">PMC:3120335</idno><idno type="doi">10.1107/S1600536811018009</idno><date when="2011">2011</date><idno type="wicri:Area/Pmc/Corpus">000A21</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A21</idno><idno type="wicri:Area/Pmc/Curation">000A21</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000A21</idno><idno type="wicri:Area/Pmc/Checkpoint">001345</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">001345</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanol: a possible metabolite of the synthetic musk fragrance AHTN</title><author><name sortKey="Faust, Rudiger" sort="Faust, Rudiger" uniqKey="Faust R" first="Rüdiger" last="Faust">Rüdiger Faust</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Nauroozi, Djawed" sort="Nauroozi, Djawed" uniqKey="Nauroozi D" first="Djawed" last="Nauroozi">Djawed Nauroozi</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Bruhn, Clemens" sort="Bruhn, Clemens" uniqKey="Bruhn C" first="Clemens" last="Bruhn">Clemens Bruhn</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Koch, Britta" sort="Koch, Britta" uniqKey="Koch B" first="Britta" last="Koch">Britta Koch</name><affiliation wicri:level="1"><nlm:aff id="a">Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kuhlich, Paul" sort="Kuhlich, Paul" uniqKey="Kuhlich P" first="Paul" last="Kuhlich">Paul Kuhlich</name><affiliation wicri:level="1"><nlm:aff id="b">BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Piechotta, Christian" sort="Piechotta, Christian" uniqKey="Piechotta C" first="Christian" last="Piechotta">Christian Piechotta</name><affiliation wicri:level="1"><nlm:aff id="b">BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Nehls, Irene" sort="Nehls, Irene" uniqKey="Nehls I" first="Irene" last="Nehls">Irene Nehls</name><affiliation wicri:level="1"><nlm:aff id="b">BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</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="2011">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The title compound (AHTN-OH), C<sub>17</sub>H<sub>26</sub>O, was prepared in order to provide standard materials for the qualitative and quantitative analysis of environmental pollutants. The molecule possesses a chiral C atom, although the structure determination was performed on racemic material, expressed in the structure as disordered chiral sites. The asymmetric unit consists of four AHTN-OH molecules containing an hydroxy group and forming a tetrameric cyclic motif built up by four strong hydrogen bonds between these hydroxy groups and additionally by two weak C—H⋯π interactions. Furthermore, these tetramers are linked <italic>via</italic> very weak C—H⋯π interactions, forming chains along the <italic>c</italic> axis.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><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="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">21754834</article-id><article-id pub-id-type="pmc">3120335</article-id><article-id pub-id-type="publisher-id">bg2389</article-id><article-id pub-id-type="doi">10.1107/S1600536811018009</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536811018009</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title>(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanol: a possible metabolite of the synthetic musk fragrance AHTN</article-title><alt-title><italic>C<sub>17</sub>H<sub>26</sub>O</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Faust</surname><given-names>Rüdiger</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Nauroozi</surname><given-names>Djawed</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Bruhn</surname><given-names>Clemens</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Koch</surname><given-names>Britta</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Kuhlich</surname><given-names>Paul</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Piechotta</surname><given-names>Christian</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Nehls</surname><given-names>Irene</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><aff id="a"><label>a</label>Institute for Chemistry, University of Kassel, Heinrich-Plett-Strasse 40, 34132 Kassel,<country>Germany</country></aff><aff id="b"><label>b</label>BAM–Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin,<country>Germany</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>r.faust@uni-kassel.de</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>6</month><year>2011</year></pub-date><pub-date pub-type="epub"><day>20</day><month>5</month><year>2011</year></pub-date><pub-date pub-type="pmc-release"><day>20</day><month>5</month><year>2011</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>67</volume><issue>Pt 6</issue><issue-id pub-id-type="publisher-id">e110600</issue-id><fpage>o1462</fpage><lpage>o1463</lpage><history><date date-type="received"><day>01</day><month>2</month><year>2011</year></date><date date-type="accepted"><day>12</day><month>5</month><year>2011</year></date></history><permissions><copyright-statement>© Faust et al. 2011</copyright-statement><copyright-year>2011</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/S1600536811018009">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>The title compound (AHTN-OH), C<sub>17</sub>H<sub>26</sub>O, was prepared in order to provide standard materials for the qualitative and quantitative analysis of environmental pollutants. The molecule possesses a chiral C atom, although the structure determination was performed on racemic material, expressed in the structure as disordered chiral sites. The asymmetric unit consists of four AHTN-OH molecules containing an hydroxy group and forming a tetrameric cyclic motif built up by four strong hydrogen bonds between these hydroxy groups and additionally by two weak C—H⋯π interactions. Furthermore, these tetramers are linked <italic>via</italic> very weak C—H⋯π interactions, forming chains along the <italic>c</italic> axis.</p></abstract></article-meta></front><floats-group><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (Å, °)</title><p><italic>Cg</italic>4, <italic>Cg</italic>10, <italic>Cg</italic>14 and <italic>Cg</italic>17 are the centroids of the C19–C22/C27/C28, C36–C39/C44/C45, C53–C56/C61/C62 and C2–C5/C10/C11 rings, respectively.</p></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">O1—H1⋯O4</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.753 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">168</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O2—H2⋯O1</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.98</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.794 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">162</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O3—H3⋯O2</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.92</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.7545)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">174</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O4—H4⋯O3</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.95</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.790 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">173</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C29—H29<italic>A</italic>⋯<italic>Cg</italic>14<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.98</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.83</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.632 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">140</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C29—H29<italic>B</italic>⋯<italic>Cg</italic>17</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.98</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.58</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.466 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">151</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C63—H63<italic>A</italic>⋯<italic>Cg</italic>10</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.98</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.69</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.471 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">137</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C63—H63<italic>B</italic>⋯<italic>Cg</italic>4<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.98</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.72</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.641 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">157</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-67-o1462-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-67-o1462-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc><affiliations><list><country><li>Allemagne</li></country></list><tree><country name="Allemagne"><noRegion><name sortKey="Faust, Rudiger" sort="Faust, Rudiger" uniqKey="Faust R" first="Rüdiger" last="Faust">Rüdiger Faust</name></noRegion><name sortKey="Bruhn, Clemens" sort="Bruhn, Clemens" uniqKey="Bruhn C" first="Clemens" last="Bruhn">Clemens Bruhn</name><name sortKey="Koch, Britta" sort="Koch, Britta" uniqKey="Koch B" first="Britta" last="Koch">Britta Koch</name><name sortKey="Kuhlich, Paul" sort="Kuhlich, Paul" uniqKey="Kuhlich P" first="Paul" last="Kuhlich">Paul Kuhlich</name><name sortKey="Nauroozi, Djawed" sort="Nauroozi, Djawed" uniqKey="Nauroozi D" first="Djawed" last="Nauroozi">Djawed Nauroozi</name><name sortKey="Nehls, Irene" sort="Nehls, Irene" uniqKey="Nehls I" first="Irene" last="Nehls">Irene Nehls</name><name sortKey="Piechotta, Christian" sort="Piechotta, Christian" uniqKey="Piechotta C" first="Christian" last="Piechotta">Christian Piechotta</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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