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2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol
Four independent molecules (A–D) comprise the asymmetric unit of the title compound, C(15)H(26)O(2), which differ only in the relative orientations of the terminal –C(Me)(2)OH groups [e.g. the range of C(methylene)—C(methine)—C(quaternary)—O(hydroxy) torsion angles is 52.7 (7)–57.1 (6)°, where th...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120619/ https://www.ncbi.nlm.nih.gov/pubmed/25161564 http://dx.doi.org/10.1107/S1600536814013543 |
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author | Burrett, Stacey Taylor, Dennis K. Tiekink, Edward R. T. |
author_facet | Burrett, Stacey Taylor, Dennis K. Tiekink, Edward R. T. |
author_sort | Burrett, Stacey |
collection | PubMed |
description | Four independent molecules (A–D) comprise the asymmetric unit of the title compound, C(15)H(26)O(2), which differ only in the relative orientations of the terminal –C(Me)(2)OH groups [e.g. the range of C(methylene)—C(methine)—C(quaternary)—O(hydroxy) torsion angles is 52.7 (7)–57.1 (6)°, where the C(methylene) atom is bound to an epoxide C atom]. The five-membered rings adopt envelope conformations, with the methylene C atom adjacent to the methine C atom being the flap atom in each case. In each molecule, the conformation of the seven-membered ring is a half-chair, with the C(methylene)—C(methine) bond, flanked by methylene C atoms, being the back of the chair. Supramolecular helical chains along the b axis are found in the crystal packing, sustained by hydroxy–epoxide O—H⋯O hydrogen bonding. Molecules of A self-associate into a chain as do those of D. A third independent chain comprising B and C molecules is also formed. The studied crystal is a pseudo-merohedral twin (minor component ca 21%). |
format | Online Article Text |
id | pubmed-4120619 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-41206192014-08-26 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol Burrett, Stacey Taylor, Dennis K. Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers Four independent molecules (A–D) comprise the asymmetric unit of the title compound, C(15)H(26)O(2), which differ only in the relative orientations of the terminal –C(Me)(2)OH groups [e.g. the range of C(methylene)—C(methine)—C(quaternary)—O(hydroxy) torsion angles is 52.7 (7)–57.1 (6)°, where the C(methylene) atom is bound to an epoxide C atom]. The five-membered rings adopt envelope conformations, with the methylene C atom adjacent to the methine C atom being the flap atom in each case. In each molecule, the conformation of the seven-membered ring is a half-chair, with the C(methylene)—C(methine) bond, flanked by methylene C atoms, being the back of the chair. Supramolecular helical chains along the b axis are found in the crystal packing, sustained by hydroxy–epoxide O—H⋯O hydrogen bonding. Molecules of A self-associate into a chain as do those of D. A third independent chain comprising B and C molecules is also formed. The studied crystal is a pseudo-merohedral twin (minor component ca 21%). International Union of Crystallography 2014-06-14 /pmc/articles/PMC4120619/ /pubmed/25161564 http://dx.doi.org/10.1107/S1600536814013543 Text en © Burrett et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ 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. |
spellingShingle | Organic Papers Burrett, Stacey Taylor, Dennis K. Tiekink, Edward R. T. 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol |
title | 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol |
title_full | 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol |
title_fullStr | 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol |
title_full_unstemmed | 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol |
title_short | 2-[(3S,3aS,5R,8S,8aS)-3,8-Dimethylhexahydro-1H,4H-3a,8a-epoxyazulen-5-yl]propan-2-ol |
title_sort | 2-[(3s,3as,5r,8s,8as)-3,8-dimethylhexahydro-1h,4h-3a,8a-epoxyazulen-5-yl]propan-2-ol |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120619/ https://www.ncbi.nlm.nih.gov/pubmed/25161564 http://dx.doi.org/10.1107/S1600536814013543 |
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