Crystallographic and Conformational Analysis of [(E)-2-[(3-Chlorophenylimino)methyl])-4-Methoxyphenol]

Abstract

The crystal structure of C<inf>14</inf>H<inf>12</inf>CINO<inf>2</inf> was determined by X-ray analysis. It crystallizes in the triclinic space group Pc with a = 12.5346(10) Å, b = 4.5101(3) Å, c = 12.0534(11) Å, α = 90.00°, β = 113.669(6)°, γ = 90.00°, Z = 2, Dx = 1.393 mg/m3, μ (MoK<inf>α</inf>) = 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 C-H⋯N hydrogen bond and a strong intermolecular C-H⋯O hydrogen bond. Minimum energy conformations AMI 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. © Springer Science+Business Media, LLC 2008.