(E)-2,4-Dichloro-6-{1-[(2-chloroethyl)imino]ethyl}phenol

Abstract

The title Schiff base compound, C10H10Cl3NO, was prepared by the condensation of 1-(3,5-dichloro-2-hydroxyphenyl)ethanone with chloroethylamine. The imine adopts an E configuration with respect to the C=N bond. The H atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52 (7) and 0.48 (7), respectively, and the major occupancy component is involved in an intramolecular N—H...O hydrogen bond. The compound therefore exists in an iminium–phenolate as well as in the imino–phenol form. In the crystal, molecules are connected by C—H...O and C—H...Cl hydrogen bonds and Cl...Cl interactions [3.7864 (9) Å] into a three-dimensional network. In addition, intermolecular π–π stacking interactions [centroid–centroid distance = 4.4312 (9) Å] are observed.