Crystal structure of the thalidomide analog (3aR*,7aS*)-2-(2,6-dioxopiperidin-3-yl)hexa­hydro-1H-iso­indole-1,3(2H)-dione

The title compound, C(13)H(16)N(2)O(4), crystallizes in the monoclinic centrosymmetric space group, P2(1)/c, with four mol­ecules in the asymmetric unit, thus there is no crystallographically imposed symmetry and it is a racemic mixture. The structure consists of a six-membered unsaturated ring bound to a five-membered pyrrolidine-2,5-dione ring N-bound to a six-membered piperidine-2,6-dione ring and thus has the same basic skeleton as thalidomide, except for the six-membered unsaturated ring substituted for the aromatic ring. In the crystal, the mol­ecules are linked into inversion dimers by R (2) (2)(8) hydrogen bonding involving the N—H group. In addition, there are bifurcated C—H⋯O inter­actions involving one of the O atoms on the pyrrolidine-2,5-dione with graph-set notation R (1) (2)(5). These inter­actions along with C—H⋯O inter­actions involving one of the O atoms on the piperidine-2,6-dione ring link the mol­ecules into a complex three-dimensional array. There is pseudomerohedral twinning present which results from a 180° rotation about the [100] reciprocal lattice direction and with a twin law of 1 0 0 0 [Image: see text] 0 0 0 [Image: see text] [BASF 0.044 (1)].