Title of article :
Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-on
Author/Authors :
Mertsalov, Dmitriy F. Department of Organic Chemistry - Peoples' Friendship University of Russia - (RUDN University), Russian Federation , Nadirova, Maryana A. Department of Organic Chemistry - Peoples' Friendship University of Russia - (RUDN University), Russian Federation , Sorokina, Elena A. Department of Organic Chemistry - Peoples' Friendship University of Russia - (RUDN University), Russian Federation , Vinokurova, Marina A. Department of Organic Chemistry - Peoples' Friendship University of Russia - (RUDN University), Russian Federation , Çelikesir, Sevim Türktekin Department of Physics - Faculty of Sciences - Erciyes University, Turkey , Akkurt, Mehmet Department of Physics- Faculty of Sciences - Erciyes University, Turkey , Kolesnik, Irina A. Department of Physics- Faculty of Sciences - Erciyes University, Turkey , Bhattarai, Ajaya Department of Chemistry - M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal
Abstract :
The title compound, C24H24N2O5S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the central ring systems of both molecules, the tetrahydrofuran rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In molecules A and B, the nine-membered groups attached to the central ring system are essentially planar (r.m.s. deviations of 0.002 and 0.003 Å, respectively). They form dihedral angles of 64.97 (9) and 56.06 (10)°, respectively, with the phenyl rings. In the crystal, strong intermolecular O—H⋯O hydrogen bonds and weak intermolecular C—H⋯O contacts link the molecules, forming a three-dimensional network. In addition weak π–π stacking interactions [centroid-to centroid distance = 3.7124 (13) Å] between the pyrrolidine rings of the nine-membered groups of A molecules are observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to quantify the intermolecular interactions present in the crystal, indicating that the environments of the two molecules are very similar. The most important contributions for the crystal packing are from H⋯H (55.8% for molecule A and 53.5% for molecule B), O⋯H/H⋯O (24.5% for molecule A and 26.3% for molecule B) and C⋯H/H⋯C (12.6% for molecule A and 15.7% for molecule B) interactions.
Keywords :
crystal structure , epoxyisoindole group , tetrahydrofuran ring , pyrrolidine ring , envelope conformation , boat conformation , Hirshfeld surface analysis , IMDAF reaction
Journal title :
Acta Crystallographica Section E: Crystallographic Communications