Crystal structure of N-{[3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide

Abstract

In the title compound, C21H17BrN2O4S2, the indole ring system subtends dihedral angles of 85.96 (13) and 9.62 (16)° with the planes of the N- and C-bonded benzene rings, respectively. The dihedral angles between the benzene rings is 88.05 (17)°. The molecular conformation is stabilized by intramolecular N—H...O and C—H...O hydrogen bonds and an aromatic π–π stacking [centroid-to-centroid distance = 3.503 (2) Å] interaction. In the crystal, short Br...O [2.9888 (18) Å] contacts link the molecules into [010] chains. The chains are cross-linked by weak C—H...π interactions, forming a three-dimensional network.

Keywords

• crystal structure
• benzenesulfonamide
• phenylsulfonyl
• biological activity
• derivatives
• hydrogen bonding
• C—H...π interactions