3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile

Abstract

In the title compound, C23H19N3O4, the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3 (1) and 60.4 (1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, molecules are connected by two unique N—H...O and O—H...O hydrogen-bonding interactions, which form centrosymmetric patterns described by graph-set motifs R22(18) and R22(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C—H...O interactions and by aromatic π–π stacking interactions between the pyran and benzene rings of neighbouring molecules [centroid–centroid distance = 3.755 (1) Å and slippage = 1.371 (2) Å].