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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...

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Autores principales: Burrett, Stacey, Taylor, Dennis K., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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%).
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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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