Five symmetrically substituted 2-aryl-3-benzyl-1,3-thiazolidin-4-ones: supramolecular structures in zero, one and two dimensions

There are no direction-specifc interactions between the molecules of 3-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1,3-thiazolidin- 4-one, C18H19NO3S, (I); the molecules of 3-(4-nitrobenzyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one, C16H13N3O5S, (II), are linked by four independent C-(HO)-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-(HO)-O-... and C-H-...pi(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-(HO)-O-... hydrogen bonds and one C-H-...pi(arene) hydrogen bond, and reinforced by an aromatic pi-pi stacking interaction. In 3-(2-fluorobenzyl)-2(2-fluorophenyl)-1,3-thiazolidin-4-one, C16H13F2NOS, (V), where the 2-aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C-(HO)-O-... and C-H-...pi(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic pi-pi stacking interaction.