Crystal structure of a 2:1 co-crystal of the anti-cancer drug lenalidomide with 1,3-resorcinol.

Abstract

A 2:1 cocrystal of lenalidomide and 1,3-resorcinol [systematic name: 3-(4-amino-1-oxo-1,3-di-hydro-2H-isoindol-2-yl)piperidine-2,6-dione-benzene-1,3-diol(2/1), 2C13H13N3O3·C6H6O2] was synthesized, and its crystal structure was elucidated by single-crystal X-ray diffraction (SCXRD). The cocrystal crystallizes in the triclinic space group P1. The two symmetry-independent lenalidomide mol-ecules form a hydrogen-bonded dimeric assembly through N-H⋯O inter-actions, generating an R22(8) ring motif. In addition, O-H⋯O hydrogen bonds involving the hydroxyl groups of 1,3-resorcinol and the carbonyl oxygen atoms of the isoindolinone and glutarimide moieties of lenalidomide further contribute to the cohesion and organization of the crystal packing. The crystal structure is further consolidated by several close π-π stacking inter-actions involving the π-electrons of the isoindolinone moiety. Hirshfeld surface analysis and the corresponding two-dimensional fingerprint plots were employed to identify and qu-antify the principal inter-molecular contacts contributing to the cohesion of the cocrystal structure.

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