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Effect of ring substitution on the crystal structures of p-substitutedbenzenesulphonamides, p-XC 6 H 4 SO 2 NH 2  (X = F, Cl, Br, CH 3  or NH 2 ) has been studied by determining the crystal structures of 4-chlorobenzenesulphonamide (4-ClC 6 H 4 SO 2 NH 2 ) and 4-bromobenzenesulphonamide (4-BrC 6 H 4 SO 2 NH 2 ) and analyzing the results along with the structures of 4-methylbenzenesulphonamide (4-CH 3 C 6 H 4 SO 2 NH 2 ), 4-fluorobenzene-sulphonamide (4-FC 6 H 4 SO 2 NH 2 ) and 4-aminobenzenesulphonamide (4-NH 2 C 6 H 4 SO 2 NH 2 ). The crystal type, space group, formula units and lattice constants in Å of new structures are: (4-ClC 6 H 4 SO 2 NH 2 ); monoclinic, P2 1 /n, Z = 4, a = 6.6276(10), b = 16.219(3), c = 7.5716(10), β = 93.387(14)°; (4-BrC 6 H 4 SO 2 NH 2 ): monoclinic, P 2 1 /n, Z = 4, a = 6.5660(10), b = 16.4630(10), c = 7.6900(10), β = 92.760(10)°. Orientation of the amine group with respect to the phenyl ring is given by the torsion angles C(2)-C(1)-S-N: 70.9° and C(6)-C(1)-S-N: −108.5°. Similarly, the orientation of S, O(1) and O(2) with respect to the ring are given by torsion angles. The comparison of bond lengths and bond angles of 4-fluoro-, 4-chloro-, 4-bromo-, 4-methyl- and 4-amino-benzenesulphonamides reveal that the S-N and C-S bond lengths decrease with the introduction of electron-withdrawing substituents such as F, Cl or Br, while these groups do not have significant effects on the S-O distances. The effect on ring C-C distances was not uniform. Substitution of F, Cl or Br decreases the O-S-N bond angle, but increases the O-S-N, N-S-C(1) and C(3)-C(4)-C(5) bond angles.

Crystal Structure Studies on p-Substitutedbenzenesulphonamides 4-X-C 6 H 4 SO 2 NH 2 (X = CH 3 , NH 2 F, Cl or Br)