Crystal structures of 3-(2H-1,3-benzodioxol-5-ylmethyl)-2-(m- and p-nitrophenyl)-1,3-thiazolidin-4-ones: different roles of the oxygen atoms

Abstract

Abstract The crystal structures of two isomeric 3-(2H-1,3-benzodioxol-5-ylmethyl)-2-(aryl)-1,3-thiazolidin-4-one compounds (1: aryl=4-O2NC6H4; 2: aryl=3-O2NC6H4) are reported. In both these nonplanar, compounds, the carbonyl oxygen is involved in intramolecular C–H···O hydrogen bonds. However, there are significant differences in the sets of intermolecular interactions, in particular the roles of the oxygen atoms, exhibited by the two compounds. Thus in 1, a dioxolyl oxygen and the two nitro group oxygen atoms are each involved in different chain forming C–H···O intermolecular hydrogen bonds, while the carbonyl oxygen atom is not involved in any intermolecular interaction. In 2, the dioxolyl oxygen atom is involved in the formation of centrosymmetric dimers, the carbonyl oxygen in three different C–H···O hydrogen bonds and the nitro group oxygens in two N–O···π(aryl) interactions. Compound 2 exhibits also C–H···π(phenyl), π(phenyl)···π(phenyl) and π(benzodioxolyl)···π(benzodioxolyl) interactions, while in 1 only the latter interaction is present. Compound 1 crystallizes in the monoclinic space group, P21/a with Z=4, while compound 2 crystallizes in the triclinic space group, P1̅, with Z=2.