Hydrogen-bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonates.

In O-ethyl N-benzoylthiocarbamate, C(10)H(11)NO(2)S, 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, C(11)H(13)NO(2)S, into chains of rings, which are linked into sheets by an aromatic pi-pi stacking interaction. In O,S-diethyl N-(4-methylbenzoyl)imidothiocarbonate, C(13)H(17)NO(2)S, pairs of molecules are linked into centrosymmetric dimers by pairs of symmetry-related C-H...pi(arene) hydrogen bonds, while the molecules of O,S-diethyl N-(4-chlorobenzoyl)imidothiocarbonate, C(12)H(14)ClNO(2)S, are linked by a single C-H...O hydrogen bond into simple chains, pairs of which are linked by an aromatic pi-pi stacking interaction to form a ladder-type structure.