Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one

Acta Crystallogr Sect E Struct Rep Online. 2014 Nov 26;70(Pt 12):o1292. doi: 10.1107/S1600536814024568. eCollection 2014 Dec 1.

Abstract

In the title compound, C20H17NO3, the methyl-idene-cyclo-hexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615 (10) Å] and is oriented at diherdral angles of 69.60 (7) and 1.69 (9)° to the phenyl and hy-droxy-benzene rings, respectively. The amino group links with the carbonyl O atom via an intra-molecular N-H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, the mol-ecules are linked by O-H⋯O hydrogen bonds and weak C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional supra-molecular architecture.

Keywords: C—H⋯π inter­actions; azomethines; crystal structure; drug properties; hydrogen bonding; hydro­philicity; industrial applications; pharmaceutical applications.