Crystal structures of 4-methoxy-N-(4-methylphenyl)benzenesulfonamide and N-(4-fluorophenyl)-4-methoxybenzenesulfonamide

Abstract

Crystal structures of two N-(aryl)arylsulfonamides, namely, 4-methoxy-N-(4-methylphenyl)benzenesulfonamide, C14H15NO3S, (I), and N-(4-fluorophenyl)-4-methoxybenzenesulfonamide, C13H12FNO3S, (II), were determined and analyzed. In (I), the benzenesulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°. In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°. In the crystal structure of (I), N—H...O hydrogen bonds form infinite C(4) chains extended in [010], and intermolecular C—H...πaryl interactions link these chains into layers parallel to the ab plane. The crystal structure of (II) features N—H...O hydrogen bonds forming infinite one dimensional C(4) chains along [001]. Further, a pair of C—H...O intermolecular interactions consolidate the crystal packing of (II) into a three-dimensional supramolecular architecture.

Keywords

• crystal structure
• N-(aryl)arylsulfonamides
• C—H...O interactions
• C—H...π interactions