Crystal structures of two N-(4-aryl)-benzenesulfonamides, namely, 4-bromo-N-(4-nitrophenyl)-benzenesulfonamide (1), and 4-fluoro-N-(4-nitrophenyl)-4-benzenesulfonamide (2) were synthesized and their molecular and crystal structures were determined by single crystal X-ray diffraction studies. Both 1 and 2 crystallize in the monoclinic crystal system, in P21/n and P21/c space groups respectively. The dihedral angle between the benzene rings is quite different in 1 and 2, 32.6(6)oin 1 and 60.4(2)o in 2. Also, the molecules of 1 and 2 show significant differences in the torsional angles defining the conformations of the two benzene rings with respect to the central -C-S(O2)-N-Csegment. The crystal structures of 1 and 2 exhibit different preferences in their packing modes. In 1, structure directing N-H…O hydrogen bonds and three structure directing C-H…O interactions along with N-O…π and CBr… O weak interactions consolidate the crystal structure into a three dimensional structure, while, the two dimensional supramolecular architecture in 2 results from a structure directing C-H…O interaction, and also features N-O…π and two π…π interactions. The N-H…O hydrogen bonds in 2 have no structure directing features.Hirshfeld surface analysis were performed on 1 and 2 to analyse the various intermolecular interactions observed in 1 and 2.