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

Abstract

The title compound, C13H16N2O4, crystallizes in the monoclinic centrosymmetric space group, P21/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 R22(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 R12(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 1 0 0 0 1[BASF 0.044 (1)].