Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position

Abstract

The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C10H8Cl3NOS),1and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C10H7Cl4NOS)2, are structurally related with one atom substitution difference in theparaposition of the benzene ring. In both structures, the thiazolidinone ring adopts an envelope conformation with the S atom as the flap. The dihedral angles between the rings [48.72 (11) in1and 48.42 (9)° in2] are very similar and the molecules are almost superimposable. In both crystal structures, C—H...O `head-to-tail' interactions between the chiral carbon atoms and the thiazolidinone oxygen atoms result in infinite monochiral chains along the direction of the shortest unit-cell parameter, namelyain1andbin2. C—H...π interactions between the thiazolidinone carbon atom at the 4-position and the phenyl ring of the neighboring enantiomer also help to stabilize the packing in each case, although the crystals are not isostructural.