3,5-Dichloro-N-(2,4-dichlorophenyl)benzenesulfonamide

Abstract

The molecule of the title compound, C12H7Cl4NO2S, is U-shaped, with the central C—S—N—C segment having a torsion angle of −58.7 (3)°. The dihedral angle between the benzene rings is 40.23 (2)°. Further, the ortho Cl atom on the aniline ring is syn to the N—H bond in the central –C—S(O2)—NH—C– segment. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers that enclose R22(8) loops. These dimers are linked by C—H...O hydrogen bonds that form a double C(7) chain propagating along the b-axis direction. These chains are further consolidated by Cl...Cl halogen bonds [3.4331 (2) Å]. π–π contacts [centroid–centroid distance = 3.6574 (19) Å] between the aniline rings link adjacent chains into a three-dimensional supramolecular network with molecules stacked along the b-axis direction.

Keywords

• crystal structure
• sulfonamides
• N—H...O hydrogen bonds
• C—H...O interactions
• Cl...Cl contacts
• π–π interactions