Open AccessFive symmetrically substituted 2‐aryl‐3‐benzyl‐1,3‐thiazolidin‐4‐ones: supramolecular structures in zero, one and two dimensions
Author(s) -
Cunico Wilson,
Capri Liliane R.,
Gomes C. R. B.,
Wardell Solange M. S. V.,
Low John N.,
Glidewell Christopher
Publication year - 2007
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270106055272
Subject(s) - chemistry , hydrogen bond , stacking , supramolecular chemistry , ring (chemistry) , aryl , nitro , aromaticity , stereochemistry , crystallography , medicinal chemistry , crystal structure , molecule , alkyl , organic chemistry
There are no direction‐specific interactions between the molecules of 3‐(2‐methoxybenzyl)‐2‐(2‐methoxyphenyl)‐1,3‐thiazolidin‐4‐one, C 18 H 19 NO 3 S, (I); the molecules of 3‐(4‐nitrobenzyl)‐2‐(4‐nitrophenyl)‐1,3‐thiazolidin‐4‐one, C 16 H 13 N 3 O 5 S, (II), are linked by four independent C—H⋯O hydrogen bonds into complex chains of fused rings. In 3‐(4‐methoxybenzyl)‐2‐(4‐methoxyphenyl)‐1,3‐thiazolidin‐4‐one, (III), isomeric with (I), the molecules are linked into sheets by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds, while in 3‐(2‐nitrobenzyl)‐2‐(2‐nitrophenyl)‐1,3‐thiazolidin‐4‐one, (IV), isomeric with (II), the sheets are built from three independent C—H⋯O hydrogen bonds and one C—H⋯π(arene) hydrogen bond, and reinforced by an aromatic π–π stacking interaction. In 3‐(2‐fluorobenzyl)‐2‐(2‐fluorophenyl)‐1,3‐thiazolidin‐4‐one, C 16 H 13 F 2 NOS, (V), where the 2‐aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic π–π stacking interaction.