Crystal structure of the thalidomide analog (3a R*,7a S*)-2-(2,6-dioxopiperidin-3-yl)hexa-hydro-1 H-iso-indole-1,3(2 H)-dione

Yousef Hijji; Ellis Benjamin; Jerry P Jasinski; Ray J Butcher

doi:10.1107/S2056989018014317

Crystal structure of the thalidomide analog (3a R,7a S)-2-(2,6-dioxopiperidin-3-yl)hexa-hydro-1 H-iso-indole-1,3(2 H)-dione

Acta Crystallogr E Crystallogr Commun. 2018 Oct 16;74(Pt 11):1595-1598. doi: 10.1107/S2056989018014317. eCollection 2018 Nov 1.

Authors

Yousef Hijji¹, Ellis Benjamin², Jerry P Jasinski³, Ray J Butcher⁴

Affiliations

¹ Department of Chemistry and Earth Sciences, Qatar University, Doha, Qatar.
² Department of Chemistry, Richard Stockton College of New Jersey, Galloway, NJ 08205, USA.
³ Department of Chemistry, Keene State College, 229 Main Street, Keene NH 03435, USA.
⁴ Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.

Abstract

The title compound, C₁₃H₁₆N₂O₄, crystallizes in the monoclinic centrosymmetric space group, P2₁/c, with four mol-ecules 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 mol-ecules 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 inter-actions involving one of the O atoms on the pyrrolidine-2,5-dione with graph-set notation R ¹ ₂(5). These inter-actions along with C-H⋯O inter-actions involving one of the O atoms on the piperidine-2,6-dione ring link the mol-ecules 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 0 0 0 [BASF 0.044 (1)].

Keywords: crystal structure; pseudomerohedral twinning; thalidomide analogs.

Grants and funding

This work was funded by National Science Foundation, Directorate for Mathematical and Physical Sciences grant 1205608 to R. J. Butcher. Qatar National Research Fund grant NPRP 7-495-1-094 to Y. Hijji.