Open AccessHydrogen‐bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonates
Author(s) -
Insuasty Henry,
Castro Edison,
Sánchez Edison,
Cobo Justo,
Glidewell Christopher
Publication year - 2010
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270110005032
Subject(s) - hydrogen bond , stacking , chemistry , thio , crystallography , stereochemistry , aromaticity , medicinal chemistry , molecule , organic chemistry
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 π–π 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...π(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 π–π stacking interaction to form a ladder‐type structure.