1-[4-({4-[(E)-(2-Hydroxynaphthalen-1-yl)methylideneamino]phenyl}sulfanyl)phenyl]ethanone

Abstract

The title Schiff base compound, C25H19NO2S, crystallizes in a statistically disordered structure comprising keto and enol tautomeric forms. In the enol form, the benzenoid arrangment is promoted by a strong intra­molecular O—H⋯N hydrogen bond and adopts an E conformation about the imine bond. In the keto form there is an intramolecular N—H⋯O hydrogen bond. In the crystal, an extended network of C—H⋯O hydrogen bonds stabilizes columns parallel to the c axis, forming large voids (there are four cavities of 108 Å3 per unit cell) with highly disordered residual electron density. The SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155] was used to eliminate the contribution of this electron density from the intensity data, and the solvent-free model was employed for the final refinement. The contribution of this undetermined solvent was ignored in the calculation of the unit-cell characteristics.