In O-ethyl N-benzoylthiocarbamate, C10H11NO2S, the molecules are linked into sheets by a combination of two-centre N—H⋯O and C—H⋯S hydrogen bonds and a three-centre C—H⋯(O,S) hydrogen bond. A combination of two-centre N—H⋯O and C—H⋯O hydrogen bonds links the molecules of O-ethyl N-(4-methylbenzoyl)thiocarbamate, C11H13NO2S, into chains of rings, which are linked into sheets by an aromatic π–π stacking interaction. In O,S-diethyl N-(4-methylbenzoyl)imidothiocarbonate, C13H17NO2S, pairs of molecules are linked into centrosymmetric dimers by pairs of symmetry-related C—H⋯π(arene) hydrogen bonds, while the molecules of O,S-diethyl N-(4-chlorobenzoyl)imidothiocarbonate, C12H14ClNO2S, are linked by a single C—H⋯O hydrogen bond into simple chains, pairs of which are linked by an aromatic π–π stacking interaction to form a ladder-type structure.
