The discrete role of chlorine substitutions in the conformation and supramolecular architecture of arylsulfonamides

Two arylsulfonamide derivatives, N-(4-acetylphenyl)benzenesulfonamide, C14H13NO3S, and N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide, C14H11Cl2NO3S, differing by the absence or presence of two chloro substituents on one of the phenyl rings, were synthesized and characterized in order to establish structural relationships and the role of chloro substitution on the molecular conformation and crystal assembly. Both arylsulfonamides form inversion-related dimers through C-H center dot center dot center dot pi and pi-pi interactions. These dimers pack in a similar way in the two structures. The substitution of two H atoms at the 2- and 5-positions of one phenyl ring by Cl atoms did not substantially alter the molecular conformation or the intermolecular architecture displayed by the unsubstituted sulfonamide. The structural information controlling the assembly of such compounds in their crystal phases is in the (phenyl)benzenesulfonamide molecular framework.