Structure of (±)-aminoglutethimide

(+/-)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, C13H16N2O2, Mr = 232.3, monoclinic, P2(1)/n, a = 16.895 (2), b = 8.519 (1), c = 8.762 (1) A, beta = 95.71 (1) degree, V = 1254.9 (2) A3, Z = 4, Dx = 1.23 g cm-3, lambda(Mo K alpha) = 0.71069 A, mu = 0.785 cm-1, F(000) = 496, T = 294 K, R = 0.064 for all 3676 reflections. The molecule is L shaped with the p-aminophenyl and the piperidinedione groups forming the vertical arm and the base, respectively. The polar imide half of the piperidinedione group is in front of the L for the active + enantiomer and at the back for the less-active - enantiomer. The structure is very similar to that of phenobarbital. Intermolecular interactions include one strong and one weak hydrogen bond and an apparent interaction between one of the amino H atoms with the pi cloud of the phenyl ring.