Open AccessSupramolecular structures of four ( Z )‐5‐arylmethylene‐2‐thioxothiazolidin‐4‐ones: hydrogen‐bonded dimers, chains of rings and sheets
Author(s) -
Delgado Paula,
Quiroga Jairo,
Cobo Justo,
Low John N.,
Glidewell Christopher
Publication year - 2005
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270105021888
Subject(s) - hydrogen bond , crystallography , chemistry , molecule , supramolecular chemistry , stereochemistry , crystal structure , organic chemistry
In each of the four title compounds, namely ( Z )‐5‐benzylidene‐2‐thioxothiazolidin‐4‐one, C 10 H 7 NOS 2 , (I), which crystallizes with Z ′ = 2 in space group P 2 1 / n , ( Z )‐5‐(4‐methylbenzylidene)‐2‐thioxothiazolidin‐4‐one, C 11 H 9 NOS 2 , (II), ( Z )‐2‐thioxo‐5‐[4‐(trifluoromethyl)benzylidene]thiazolidin‐4‐one, C 11 H 6 F 3 NOS 2 , (III), and ( Z )‐5‐(4‐methoxybenzylidene)‐2‐thioxothiazolidin‐4‐one, C 11 H 9 NO 2 S 2 , (IV), there is a very wide C—C—C angle ( ca 130°) at the methine C atom linking the two rings. Pairs of N—H⋯O hydrogen bonds link the two independent molecules in (I) into a cyclic dimeric unit, and these units are further linked into complex sheets by three independent C—H⋯π(arene) hydrogen bonds. The molecules of (II) are linked by paired N—H⋯O hydrogen bonds into centrosymmetric R 2 2 (8) dimers; the molecules of (III) and (IV) are linked into chains of rings, which are constructed from a combination of N—H⋯S and C—H⋯O hydrogen bonds in (III), and from a combination of N—H⋯O and C—H⋯S hydrogen bonds in (IV).