Cargando…

(1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne

The title compound, C(16)H(24)Br(2)O, was synthesized from β-himachalene (3,5,5,9-tetra­methyl-2,4a,5,6,7,8-hexa­hydro-1H-benzocyclo­heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The mol­ecule contains fused six- and seven-membered rings, each linked to a...

Descripción completa

Detalles Bibliográficos
Autores principales: Oukhrib, Abdelouahd, Benharref, Ahmed, Saadi, Mohamed, Berraho, Moha, El Ammari, Lahcen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629578/
https://www.ncbi.nlm.nih.gov/pubmed/23634065
http://dx.doi.org/10.1107/S1600536813006077
_version_ 1782266606527709184
author Oukhrib, Abdelouahd
Benharref, Ahmed
Saadi, Mohamed
Berraho, Moha
El Ammari, Lahcen
author_facet Oukhrib, Abdelouahd
Benharref, Ahmed
Saadi, Mohamed
Berraho, Moha
El Ammari, Lahcen
author_sort Oukhrib, Abdelouahd
collection PubMed
description The title compound, C(16)H(24)Br(2)O, was synthesized from β-himachalene (3,5,5,9-tetra­methyl-2,4a,5,6,7,8-hexa­hydro-1H-benzocyclo­heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The mol­ecule contains fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55 (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6 (2) and 80.5 (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each mol­ecule is linked to its symmetry-equivalent partner by C—H⋯O hydrogen bonds, forming zigzag chains parallel to [100].
format Online
Article
Text
id pubmed-3629578
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-36295782013-04-30 (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne Oukhrib, Abdelouahd Benharref, Ahmed Saadi, Mohamed Berraho, Moha El Ammari, Lahcen Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(24)Br(2)O, was synthesized from β-himachalene (3,5,5,9-tetra­methyl-2,4a,5,6,7,8-hexa­hydro-1H-benzocyclo­heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The mol­ecule contains fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55 (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6 (2) and 80.5 (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each mol­ecule is linked to its symmetry-equivalent partner by C—H⋯O hydrogen bonds, forming zigzag chains parallel to [100]. International Union of Crystallography 2013-03-09 /pmc/articles/PMC3629578/ /pubmed/23634065 http://dx.doi.org/10.1107/S1600536813006077 Text en © Oukhrib et al. 2013 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
Oukhrib, Abdelouahd
Benharref, Ahmed
Saadi, Mohamed
Berraho, Moha
El Ammari, Lahcen
(1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
title (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
title_full (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
title_fullStr (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
title_full_unstemmed (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
title_short (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
title_sort (1s,3r,8r,9r,10s)-2,2-dibromo-3,7,7,10-tetra­methyl-9β,10β-ep­oxy-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.0(1,3)]dodeca­ne
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629578/
https://www.ncbi.nlm.nih.gov/pubmed/23634065
http://dx.doi.org/10.1107/S1600536813006077
work_keys_str_mv AT oukhribabdelouahd 1s3r8r9r10s22dibromo37710tetramethyl9b10bepoxy37710tetramethyltricyclo640013dodecane
AT benharrefahmed 1s3r8r9r10s22dibromo37710tetramethyl9b10bepoxy37710tetramethyltricyclo640013dodecane
AT saadimohamed 1s3r8r9r10s22dibromo37710tetramethyl9b10bepoxy37710tetramethyltricyclo640013dodecane
AT berrahomoha 1s3r8r9r10s22dibromo37710tetramethyl9b10bepoxy37710tetramethyltricyclo640013dodecane
AT elammarilahcen 1s3r8r9r10s22dibromo37710tetramethyl9b10bepoxy37710tetramethyltricyclo640013dodecane