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In the title compound, C17H25N3O2S, the terminal and central amide groups are, respectively, twisted and coplanar with the attached benzene ring [O—C—C—C torsion angles = 22.7 (3) and 5.4 (3)°]. In the central part of the mol­ecule, the amide and thio­amide residues are approximately perpendicular [C—N—C—S torsion angle = −104.98 (18)°]. Supra­molecular layers with a zigzag topology are formed in the crystal packing by N—H...O, N—H...S and C—H...O inter­actions; these stack along c, being separated by hydro­phobic inter­actions.

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Two independent mol­ecules with quite similar conformations, A and B, comprise the asymmetric unit of the title compound, C23H21N3O2S. The terminal amide substituent is coplanar with the attached benzene ring [the O—C—C—C torsion angles are 174.0 (2) (A) and 6.3 (3)° (B)]. In the same way, the central amide group [C—C—C—O = 7.8 (3) (A) and 11.5 (3)° (B)] is approximately coplanar with the ring to which it is attached. A major twist is noted between the amide and adjacent thio­amide residues [C—N—C—S = −109.29 (19) (A) and −112.29 (19)° (B)]. In the crystal, supra­molecular chains along [100] are formed by N—H...O and N—H...S hydrogen bonding. These are connected into a three-dimensional architecture by C—H...π and π–π inter­actions [inter-centroid distance = 3.9157 (12) Å].
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