Synthesis, Crystal Structure and Conformational Analysis of (E)-5-Methoxy2-((4-Methoxyphenylimino)Methyl)Phenol

Abstract

The title compound, (E)-5-memoxy-2-((4-memoxyphenylimino)methyl)phenol (C<inf>15</inf>H<inf>15</inf>NO<inf>3</inf>), crystallizes in monoclinic, space group P2<inf>1</inf>/c with a = 9.4361(6), b = 10.6212(5), c = 12.9338(9) Å, β = 93.064(5)°, V= 1294.41(14) Å3, Z = 4, D<inf>c</inf> = 1.320 g/cm3, F(000) = 544, R<inf>int</inf> = 0.116, T= 296 K, = 0.09 mm-1, the final R = 0.051 and wR = 0.148 for 1836 observed reflections with I > 2σ(I). An extensive two-dimensional network of C-H-O hydrogen bonds and Π-ring interactions are responsible for the crystal stabilization. Intermolecular hydrogen bonds and C-H-Π interactions produce R22(14), R44(30) and R4 4(31) rings. In addition to the molecular geometry from X-ray experiment, the molecular geometry of the title compound in the ground state has been calculated using the semi-empirical (AMI and PM3) and density functional theory method (DFT) (B3LYP) with 6-31G(d) basis set. To determine the conformational flexibility, molecular energy profile of the title compound was obtained by semi-empirical (PND and AMI) and DFT/B3LYP calculations with respect to the selected degree of torsional freedom, which varied from -180° to +180° in a step of 10°.