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In the structure of the title compound, C(18)H(15)ClN(4)O(4)S, the dihedral angle between the two benzene rings is 1.4 (3)°. The angle between the phenyl ring and thia-diazole ring is 5.8 (4)°. The conformations of the N-H and C=O bonds are anti with respect to each other. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯N, N-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network.

In the structure of the title compound, C(17)H(13)BrN(4)O(2)S, the dihedral angle between the two benzene rings is 38.5 (1)°; the angle between the 4-bromo-benzene and thia-diazole rings is 1.3 (1)°. The conformations of the N-H and C=O bonds are anti with respect to each other. The structure displays inter-molecular N-H⋯O and C-H⋯O hydrogen bonding, with both interactions leading to inversion dimers.

In the title compound, C(20)H(17)ClN(4)O(2)S, the dihedral angle between the two benzene rings is 65.9 (1)°; the corresponding angle between the 4-chloro-phenyl and thia-diazole rings is 3.4 (8)°. The conformations of the N-H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The structure displays intermolecular N-H⋯O, C-H⋯N, C-H⋯S and C-H⋯O hydrogen bonding.

The asymmetric unit of the title compound, C(21)H(20)N(4)O(3)S, contains two independent mol-ecules. The dihedral angles between the two benzene rings are 47.6 (1) and 30.2 (1)°, the corresponding values between the p-methoxy-benzene and thia-diazol rings are 12.3 (1) and 24.7 (1)°, respectively, for the two mol-ecules. The conformations of the N-H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The crystal structure is stabilized by N-H⋯O and N-H⋯N inter-actions. The absolute structure could not be determined from the X-ray data but the absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.