16-(4-Cyanobenzylidene)-17-oxoandrost-5-en-3beta-ol

In the title compound, 4-(3beta-hydroxy-17-oxoandrost-5-en-16-ylidenemethyl)benzonitrile, C(27)H(31)NO(2), rings A and C of the steroid nucleus are in chair conformations. The central six-membered ring B is in an 8beta,9alpha-half-chair conformation, while the five-membered ring D adopts a 13beta,14alpha-half-chair conformation. The cyanobenzylidene moiety has an E configuration with respect to the carbonyl group at position C17. The dihedral angle between the planes of the steroid nucleus and the cyanobenzylidene moiety is 22.61 (15) degrees. Intermolecular O-H.N hydrogen bonds formed between the hydroxyl group of the steroid and the N atom of the cyanobenzylidene moiety of symmetry-related molecules link the steroid molecules into chains which run parallel to the b axis.