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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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Detalles Bibliográficos
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
Descripción
Sumario: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.