2-{(E)-[(3-Chloro-4-methylphenyl)imino]methyl}-4-(trifluoromethoxy)phenol

Abstract

In the title compound, C 15 H 11 ClF 3 NO 2 , the dihedral angle between the planes of the benzene rings is 8.3 (2) and an intramolecular O-HÁ Á ÁN hydrogen bond closes an S(6) ring. In the crystal, weak C-HÁ Á ÁO links connect the molecules into [110] chains. The F atoms of the CF 3 group are disordered over two sets of sites with refined occupancies of 0.626 (11):0.374 (11). Structure descriptionWe herein report the synthesis and structure of the new Schiff base (Fig. 1). The bond distances of the imino group atoms [N1-C9 = 1.423 (5); N1-C8 = 1.275 (5) 2) and an intramolecular O-HÁ Á ÁN hydrogen bond (Table 1) closes an S(6) ring.In the crystal (Fig. 2), weak C-HÁ Á ÁO links connect the molecules into [110] chains. Synthesis and crystallizationA mixture of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (0.19 g, 0.9 mol) in ethanol (20 ml) and 3-chloro-4-methyaniline (0.13 g, 0.9 mol) in ethanol (20 ml) were mixed and stirred for 5 h under reflux. Light-yellow plate-shaped crystals were obtained by slow evaporation of an ethanol solution (yield 67%; m.p. 361-363 K).