Crystal structures of N-(3-fluorobenzoyl)benzenesulfonamide and N-(3-fluorobenzoyl)-4-methylbenzenesulfonamide

Abstract

The crystal structures of two N-(arylsulfonyl)arylamides, namely N-(3-fluorobenzoyl)benzenesulfonamide, C13H10FNO3S, (I), and N-(3-fluorobenzoyl)-4-methylbenzenesulfonamide, C14H12FNO3S, (II), are described and compared with related structures. The dihedral angle between the benzene rings is 82.73 (10)° in (I) compared to 72.60 (12)° in (II). In the crystal of (I), the molecules are linked by C—H...O and C—H...π interactions, resulting in a three-dimensional grid-like architecture, while C—H...O interactions lead to one-dimensional ribbons in (II). The crystals of both (I) and (II) feature strong but non-structure-directing N—H...O hydrogen bonds with R22(8) ring motifs. The structure of (I) also features π–π stacking interactions.

Keywords

• crystal structure
• N-(arylsulfonyl)arylamides
• N—H...O hydrogen bonds
• C—H...O interactions
• C—H...π interactions