Abstract The asymmetric unit of Schiff base of the title molecule, C18H15NO2, was synthesized from naphthalen-2-ylamine and 2‑hydroxyl-3‑methoxy-benzaldehyde. The two phenyl rings (naphthyl and salicylaldehyde) and the azomethine group are practically co-planar, the dihedral angle between the benzenaldehyde moiety and amino phenyl plane is 14.36(9)°. An interamolecular O2−H1A•••N2 hydrogen bond generates the S(6) ring motif. The double bond distance (N2−C11; 1.281(2)A) and the bond angle (C2−N2−C11;122.86(15)°) of the title Schiff base agreed with similar azomethines derivatives. Title crystal structure is mainly stabilized by the C − H•••O and π•••π interactions. The rings are parallelly displaced in which that π−stacking interaction is an offset or slipped stacking. The ring normal and the vector between the ring centroids form an angle of about 15.63° up to centroid-centroid distance of 3.9982(11)A. The intermolecular interactions were quantified using PIXEL and Hirshfeld surface analysis. The quantum chemical calculations were performed to understand their electronic properties and to elucidate the chemical reactivity.