An analogue of indapamide: crystal structure and Hirshfeld surface analysis of 3-chloro-4-( N , N -diethynylsulfamoyl)- N -(2-methylindolin-1-yl)benzamide

The title molecule, C 22 H 20 ClN 3 O 3 S, adopts a shallow cup-shaped conformation with the chlorobenzamide portion as the bottom. A puckering analysis of the five-membered ring indicates an envelope conformation. In the crystal, helical chains along the a -axis direction are formed by N—H...O hydrogen bonds reinforced by C—H...π(ring) and weak π-stacking interactions. No directed interactions between chains appear to exist. A Hirshfeld surface analysis was performed.