Crystal structure of 5-[(benzo-yloxy)meth-yl]-5,6-dihy-droxy-4-oxo-cyclo-hex-2-en-1-yl benzoate.

Abstract

The crystal structure of the natural product zeylenone, C21H18O7, was confirmed by single-crystal X-ray diffraction. The crystal structure has three chiral centers at positions C1, C5 and C6 of the cyclo-hexa-none ring, but the absolute configuration could not be determined reliably. The methyl benzoate and benzo-yloxy substituents at positions C1 and C5 of the cyclo-hexenone ring are on the same side of the ring with the dihedral angle between their mean planes being 16.25 (10)°. These rings are almost perpendicular to the cyclo-hexenone ring. The benzoate groups and two hydroxyl groups on the cyclo-hexenone ring form strong hydrogen bonds to consolidate the crystal structure. In addition, weak C-H⋯O hydrogen bonds also contribute to the packing of the structure.