1-{(E)-[(2-Fluoro-5-nitrophenyl)imino]methyl}naphthalen-2-ol

Abstract

The title molecule, C17H11FN2O3, is nearly planar [maximum deviation = 0.197 (1) Å] and the molecular conformation is stabilized by an N—H...O hydrogen bond forming an S(6) ring motif. The H atom of the intramolecular hydrogen bond was found to be disordered over two sites and thus both the hydroxy and keto tautomers are simultaneously present in the solid. Refinement of the occupancy of this site suggests that the hydroxy form is the major component [occupancy refined to 0.59 (3):0.41 (3)]. Bond lengths are also largely consistent with dominance of the hydroxy form. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming layers parallel to (101). π–π stacking interactions [centroid–centroid distances = 3.5649 (9) and 3.7579 (9) Å] inter-connect these layers.