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-one

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 angstrom, respectively). They form dihedral angles of 64.97 (9) and 56.06 (10)degrees, respectively, with the phenyl rings. In the crystal, strong intermolecular O-H center dot center dot center dot O hydrogen bonds and weak intermolecular C-H center dot center dot center dot O contacts link the molecules, forming a three-dimensional network. In addition weak pi-pi stacking interactions [centroid-to centroid distance = 3.7124 (13) angstrom] 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 center dot center dot center dot H (55.8% for molecule A and 53.5% for molecule B), O center dot center dot center dot H/H center dot center dot center dot O (24.5% for molecule A and 26.3% for molecule B) and C center dot center dot center dot H/H center dot center dot center dot C (12.6% for molecule A and 15.7% for molecule B) interactions.

Mertsalov D.F. 1 , Nadirova M.A. 1 , Sorokina E.A. 1 , Vinokurova M.A. 1 , Celikesir S.T.2 , Akkurt M.2 , Kolesnik I.A.3 , Bhattarai A.4
International Union of Crystallography
  • 1 Peoples Friendship Univ Russia, RUDN Univ, Dept Organ Chem, 6 Miklukho Maklaya St, Moscow 117198, Russia
  • 2 Erciyes Univ, Fac Sci, Dept Phys, TR-38039 Kayseri, Turkey
  • 3 Natl Acad Sci Belarus, Inst Phys Organ Chem, Lab Organoelement Cpds, 13 Surganov St, Minsk 220072, BELARUS
  • 4 MMAMC Tribhuvan Univ, Dept Chem, Biratnagar, Nepal
Ключевые слова
crystal structure; epoxyisoindole group; tetrahydrofuran ring; pyrrolidine ring; envelope conformation; boat conformation; Hirshfeld surface analysis; IMDAF reaction
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