2-[(E)-(2-Hydroxynaphthalen-1-yl)methylideneamino]isoindoline-1,3-dione

Abstract

The title compound, C19H12N2O3, has two independent molecules (A and B) in the asymmetric unit. There is an intramolecular O—H...N hydrogen bond in each molecule. The mean planes of the naphthalene [maximum deviations = 0.024 (3) and 0.030 (3) Å in A and B, respectively] and the isoindoline units [maximum deviations 0.009 (3) and 0.008 (3) Å in A and B, respectively] are almostly coplanar, with dihedral angles of 4.25 (9) ad 3.84 (9)° in molecules A and B, respectively. The two independent molecules are connected by π–π interactions [centroid-centroid distances 3.5527 (19) and 3.5627 (19) Å]. In the crystal, the A+B pairs are further connected via π–π interactions [centroid–centroid distances = 3.693 (2)–3.831 (2) Å], leading to the formation of columns propagating along the a-axis direction. The columns are linked via C—H...O interactions, leading to the formation of a three-dimensional network.