Crystal structure of chloro-methyl 2-[2-(2,6-di-chloro-phenyl-amino)-phen-yl]acetate.

The title compound, CHClNO, was synthesized from diclofenac and chloro-methyl chloro-sulfate under phase-transfer conditions, and crystallizes in the monoclinic space group 2/. As a result of steric strain, the two adjacent aromatic six-membered rings cannot be co-planar, while the terminal ring on one side of the mol-ecule and the methyl acetate moiety atoms on the other reside roughly in the same plane. The angle between the planes of the two aromatic rings is rather wide at 64.27 (8)°. The crystal is tightly packed and consolidated by a large number and notable range of inter-molecular contacts, including relatively strong classical hydrogen bonds but also halogen bonds and even short contacts between chlorine atoms and π-bonds. The inter-molecular inter-actions were further analysed using DFT methods, the results of which are discussed in comparison to the experimental X-ray data.