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A P2(1)2(1)2(1) polymorph of (+)-clusianone

The title compound, C(33)H(42)O(4) [systematic name: (1S,5S,7R)-3-benzoyl-4-hy­droxy-8,8-dimethyl-1,5,7-tris­(3-methyl­but-2-­enyl)bi­cyclo­[3.3.1]nona-3-ene-2,9-dione], has a central bi­cyclo­[3.3.1]nonane-2,4,9-trione surrounded by tetra­prenyl­ated and benzoyl groups. The compound was recrystalli...

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Autores principales: Vaneesa Nagalingam, Sree, Wong Pik Ching, Janet, Khaled bin Break, Mohammed, Tahir, M. Ibrahim M., Khoo, Teng-Jin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4004436/
https://www.ncbi.nlm.nih.gov/pubmed/24860292
http://dx.doi.org/10.1107/S1600536813031036
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author Vaneesa Nagalingam, Sree
Wong Pik Ching, Janet
Khaled bin Break, Mohammed
Tahir, M. Ibrahim M.
Khoo, Teng-Jin
author_facet Vaneesa Nagalingam, Sree
Wong Pik Ching, Janet
Khaled bin Break, Mohammed
Tahir, M. Ibrahim M.
Khoo, Teng-Jin
author_sort Vaneesa Nagalingam, Sree
collection PubMed
description The title compound, C(33)H(42)O(4) [systematic name: (1S,5S,7R)-3-benzoyl-4-hy­droxy-8,8-dimethyl-1,5,7-tris­(3-methyl­but-2-­enyl)bi­cyclo­[3.3.1]nona-3-ene-2,9-dione], has a central bi­cyclo­[3.3.1]nonane-2,4,9-trione surrounded by tetra­prenyl­ated and benzoyl groups. The compound was recrystallized several times in methanol using both a slow evaporation method and with a crystal-seeding technique. This subsequently produced diffraction-quality crystals which crystallize in the ortho­rhom­bic space group P2(1)2(1)2(1), in contrast to a previous report of a structure determination in the Pna2(1) space group [McCandlish et al. (1976 ▶). Acta Cryst. B32, 1793–1801]. The title compound has a melting point of 365–366 K, and a specific rotation [α](20) value of +51.94°. A strong intra­molecular O—H⋯O hydrogen bond is noted. In the crystal, mol­ecules are assembled in the ab plane by weak C—H⋯O inter­actions.
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spelling pubmed-40044362014-05-23 A P2(1)2(1)2(1) polymorph of (+)-clusianone Vaneesa Nagalingam, Sree Wong Pik Ching, Janet Khaled bin Break, Mohammed Tahir, M. Ibrahim M. Khoo, Teng-Jin Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(33)H(42)O(4) [systematic name: (1S,5S,7R)-3-benzoyl-4-hy­droxy-8,8-dimethyl-1,5,7-tris­(3-methyl­but-2-­enyl)bi­cyclo­[3.3.1]nona-3-ene-2,9-dione], has a central bi­cyclo­[3.3.1]nonane-2,4,9-trione surrounded by tetra­prenyl­ated and benzoyl groups. The compound was recrystallized several times in methanol using both a slow evaporation method and with a crystal-seeding technique. This subsequently produced diffraction-quality crystals which crystallize in the ortho­rhom­bic space group P2(1)2(1)2(1), in contrast to a previous report of a structure determination in the Pna2(1) space group [McCandlish et al. (1976 ▶). Acta Cryst. B32, 1793–1801]. The title compound has a melting point of 365–366 K, and a specific rotation [α](20) value of +51.94°. A strong intra­molecular O—H⋯O hydrogen bond is noted. In the crystal, mol­ecules are assembled in the ab plane by weak C—H⋯O inter­actions. International Union of Crystallography 2013-11-23 /pmc/articles/PMC4004436/ /pubmed/24860292 http://dx.doi.org/10.1107/S1600536813031036 Text en © Vaneesa Nagalingam 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
Vaneesa Nagalingam, Sree
Wong Pik Ching, Janet
Khaled bin Break, Mohammed
Tahir, M. Ibrahim M.
Khoo, Teng-Jin
A P2(1)2(1)2(1) polymorph of (+)-clusianone
title A P2(1)2(1)2(1) polymorph of (+)-clusianone
title_full A P2(1)2(1)2(1) polymorph of (+)-clusianone
title_fullStr A P2(1)2(1)2(1) polymorph of (+)-clusianone
title_full_unstemmed A P2(1)2(1)2(1) polymorph of (+)-clusianone
title_short A P2(1)2(1)2(1) polymorph of (+)-clusianone
title_sort p2(1)2(1)2(1) polymorph of (+)-clusianone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4004436/
https://www.ncbi.nlm.nih.gov/pubmed/24860292
http://dx.doi.org/10.1107/S1600536813031036
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