Crystal structure of methyl (Z)-2-[(Z)-3-methyl-2-({(E)-1-[(R*)-4-methylcyclohex-3-en-1-yl]ethylidene}hydrazinylidene)-4-oxothiazolidin-5-ylidene]acetate

Abstract

The new title 4-thiazolidinone derivative, C16H21N3O3S, was obtained from the cyclization reaction of 4-methyl-3-thiosemicarbazone and dimethyl acetylenedicarboxylate (DMAD). The cyclohexylidene ring has an envelope conformation with the stereogenic centre C atom as the flap. Its mean plane makes a dihedral angle of 56.23 (9)° with the thiazolidine ring mean plane. In the crystal, molecules are linked by C—H...O hydrogen bonds forming chains propagating in the [001] direction. Within the chains there are offset π–π interactions between the thiazolidine rings of inversion-related molecules [centroid–centroid distance = 3.703 (1) Å]. The chains are linked by further C—H...O hydrogen bonds, forming slabs parallel to the ac plane.

Keywords

• crystal structure: hydrazine: thiazolidinone
• C—H...O hydrogen bonds
• offset π–π interactions