Synthesis and Crystal Structure of 2-(2,3,4-Trimethoxy-6-Methylbenzylideneamino)phenol

The title compound 2-(2,3,4-trimethoxy-6-methylbenzylideneamino) phenol (C17H19NO4, M-r = 301.33) was synthesised and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c, with a = 10.4458(14), b = 8.3870(10), c = 17.780(2) angstrom, beta = 91.102(2)degrees, V = 1557.4(3) angstrom(3), Z = 4, D-c = 1.285 g/cm(3), lambda = 0.71073 angstrom, mu(Mo K alpha) = 0.092 mm(-1), F(000) = 640. The final refinement gave R = 0.0452, wR(F-2) = 0.1065 for 2,743 observed reflections with I > 2 sigma(I). X-ray diffraction analysis reveals that the molecule adopts an E configuration at the C=N functional bond. The dihedral angle between the two phenyl rings is 38.3(3)degrees. The crystal structure is stabilized by C-H center dot center dot center dot O, O-H center dot center dot center dot O and O-H center dot center dot center dot N hydrogen bonds and pi-pi stacking interactions.