Clostebol acetate

The title compound, C(21)H(29)ClO(3) [systematic name (8R,9S,10R,13S,14S,17S)-4-chloro-3-oxoandrost-4-en-17β-yl acetate], is a 4-chloro derivative of testosterone, used as an anabolic androgenic agent or applied topically in ophthalmological and dermatological treatments. The absolute configurations at positions 8, 9, 10, 13, 14 and 17 were established by refinement of the Flack parameter as R, S, R, S, S, and S, respectively. Rings B and C of the steroid ring system adopt chair conformations, ring A has a half-chair conformation, while ring D is in a C(13) envelope conformation. Ring B and C, and C and D are trans fused. In the crystal, molecules are linked by a weak C—H⋯O interaction.