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The title compound, C11H9NO3, contains an isoxazole and a hydroxybenzylidene ring, which are inclined to each another by 3.18 (8)°. There is an intramolecular C—H...O contact forming an S(7) ring. In the crystal, molecules stack head-to-tail in columns along the b-axis direction, linked by offset π–π interactions [intercentroid distances of 3.676 (1) and 3.723 (1) Å]. The columns are linked by O—H...O and O—H...N hydrogen bonds, forming layers parallel to the ab plane. The layers are linked by C—H...O hydrogen bonds, forming a supramolecular three-dimensional framework. An analysis of the Hirshfeld surfaces points to the importance of the O—H...O and O—H...N hydrogen bonding in the packing mechanism of the crystal structure.

The title compound, C20H19NO2, is of interest as a precursor to biologically active substituted quinolines and related compounds. This compound crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angles between mean planes of the methylphenyl ring and the naphthalene ring system are 78.32 (6) and 84.70 (6)° in molecules A and B, respectively. In the crystal, the antiferroelectric packing of molecules A and B is of an ABBAABB type along the b-axis direction. The crystal structure features N—H...O, O—H...O and weak C—H...O hydrogen bonds, which link the molecules into infinite chains propagating along the b-axis direction.