In the title compound, C15H15NO4S, the dihedral angle between the methyl- and meth­oxy-substituted benzene rings is 88.99 (12)°. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, adjacent mol­ecules form inversion-related dimers through strong N—H⋯O hydrogen bonds, generating R 2 2(8) loops. The dimers are further connected through C—H⋯O inter­actions that form C(8) chains parallel to (001). Mol­ecules are also connected through other C—H⋯O hydrogen bonds along the b axis, forming additional C(8) chains. Two aromatic π–π stacking inter­actions [centroid–centroid separations = 3.6150 (1) and 3.6837 (1) Å] generate a three-dimensional architecture.

In the title compound, C13H9ClN2O5S, the dihedral angle between the benzene rings is 74.86 (11)°. The mol­ecule is twisted at the S atom, with a dihedral angle of 82.53 (13)° between the sulfonyl benzene ring and the S—N—C=O segment. In the crystal, mol­ecules are linked into inversion dimers through pairs of N—H⋯O hydrogen bonds, thereby forming R 2 2(8) loops. Mol­ecules are linked into C(7) [010] chains by weak C—H⋯O hydrogen bonds, and C—H⋯π inter­actions are also observed.