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In the title compound, C15H15NO4S, the dihedral angle between the benzene rings is 78.62 (16)°. In the crystal, adjacent mol­ecules are linked along the c axis into C(4) chains through strong N—H...O hydrogen bonds. Mol­ecules are further connected through C—H...O hydrogen bonds into a hexa­meric unit generating an R66(66) motif. Another C—H...O inter­action connects the mol­ecules along the c axis, forming C(5) chains. A region of disordered electron density, most probably disordered methanol–water solvent mol­ecules, was treated with the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148–155]. The formula mass and unit-cell characteristics do not take into account this disordered solvent.

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The title compound, C14H12ClNO4S, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the benzene rings are 89.68 (1) (mol­ecule 1) and 82.9 (1)° (mol­ecule 2). In each mol­ecule, intra­molecular N—H...O hydrogen bonds between the amide H atom and the meth­oxy O atom generate S(6) loops. In the crystal, mol­ecule 2 is linked into inversion dimers through pairs of C—H...O inter­actions, forming an R22(8) ring motif. Mol­ecules 1 and 2 are further linked along the b-axis direction through C—H...π inter­actions. The crystal structure is further stabilized by several π–π stacking inter­actions [centroid–centroid separations = 3.7793 (1), 3.6697 (1) and 3.6958 (1) Å], thus generating a three-dimensional architecture.
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