Research Article: rac-[3-Hydroxy-6,9-dimethyl-6-(4-methylpent-3-en-1-yl)-6a,7,8,9,10,10a-hexahydro-6H-1,9-epoxybenzo[c]chromen-4-yl](phenyl)methanone

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Gwendoline Cheng Lian Ee, Soek Sin Teh, Huey Chong Kwong, Mohamed Ibrahim Mohamed Tahir, Siau Hui Mah.

http://doi.org/10.1107/S1600536812010756

Abstract

The title compound congestiflorone, C28H32O4, which was isolated from the stem bark of Mesua congestiflora, consists of a benzophenone skeleton with two attached pyran rings to which a cyclo­hexane ring and a C6 side chain are bonded. The benzene ring is significantly distorted from planarity (r.m.s. deviation = 0.0007 Å) due to the constraints imposed by junctions with the two pyran rings. The cyclo­hexane ring is in a chair conformation, one pyran ring is in a boat conformation, while the other is a distorted chair. The phenyl and benzene rings make a dihedral angle of 55.85 (9)°. An intra­molecular O—H⋯O hydrogen bond is observed. In the crystal, mol­ecules are linked via C—H⋯O inter­actions.

Partial Text

For phytochemical investigations of Mesua congestiflora, see: Awang et al. (2010 ▶); Bala & Seshadri (1971 ▶); Ee et al. (2005b ▶); Bandaranayak et al. (1975 ▶); Morel et al. (1999 ▶); Walia & Mukerjee (1984 ▶). For the biological activity of Congestiflora species, see: Pinto et al. (1994 ▶); Ee et al. (2005a ▶); Mazumder et al. (2004 ▶); Verotta et al. (2004 ▶); Huerta-Reyes et al. (2004 ▶). For related structures, see: Hua et al. (2008 ▶); Liu et al. (2005 ▶). For a description of the Cambridge Structural Database, see Allen (2002 ▶)

 

Source:

http://doi.org/10.1107/S1600536812010756