Hydrogen-bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonates

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.