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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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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. |
format | Online Article Text |
id | pubmed-4004436 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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