Crystallographic and Conformational Analysis of [(E)-2-[(3-Chlorophenylimino)methy])-4-methoxyphenol

Abstract

The crystal structure of C14H12ClNO2 was determined by X-ray analysis. It crystallizes in the triclinic space group Pc with a = 12.5346(10) A, b = 4.5101(3) A, c = 12.0534(11) A, α = 90.00o, β = 113.669(6)o, γ = 90.00o, Z = 2, Dx = 1.393 mg/m3, μ (MoKα) = 0.298 mm−1. The title compound is photochromic and molecule is non-planar. It adopts a phenol–imine tautomeric form with a strong intramolecular O–H···N hydrogen bond and a strong intermolecular C–H···O hydrogen bond. Minimum energy conformations AM1 were calculated as a function of the three torsion angles θ1(C10–C9–N1–C8), θ2(C9–N1–C8–C1) and θ3(N1–C8–C1–C6), varied every 10°. As in the X-ray experiment results, molecule has an angle that makes it non-planar between two aromatic rings in AM1 optimized geometry. Molecular and crystal structure of [(E)-2-[(3-chlorophenylimino)methy])-4-methoxyphenol], C14H12ClNO2, have been determined by single crystal X-ray diffraction study, and conformational analysis of the title molecule with respect to the selected torsion angle has been achieved by AM1 semi-empirical calculations.