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

The title compound, C33H42O4 [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 [alpha](20) value of + 51.94(circle). A strong intramolecular O-H...O hydrogen bond is noted. In the crystal, molecules are assembled in the ab plane by weak CH...O interactions.