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Schiff base, N-(2-methoxyphenyl)-3-methoxysalicylaldimine (MPMS), was synthesized and characterized by spectroscopic methods. Crystal structure of the title compound crystallizing in the orthorhombic space group Pca2₁, a=23.695(2), b=7.7011(8), c=7.3570(9)Å, V=1342.5(2)ų, Z=4 has been solved from X-ray powder diffraction data following direct-space approach and refined by the Rietveld method. In solid state, the salicylaldimine compound exists as a phenol-imine tautomer with a strong intramolecular O–H…N hydrogen bond. The molecular geometry and electronic structure of MPMS were calculated at the DFT level using the hybrid exchange-correlation functional, BLYP. The optimized molecular geometry corresponds to the non-planar conformation of the molecule as established by the crystallographic analysis. The anticancer activity of the title Schiff base was evaluated against three different cell …