Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one

Abstract

The title compound, C16H11N2OF, is a member of the azo dye family. The dihedral angle subtended by the benzene ring and the naphthalene ring system measures 18.75 (7)°, indicating that the compound is not perfectly planar. An intramolecular N—H...O hydrogen bond occurs between the imino and carbonyl groups. In the crystal, the molecules are linked into inversion dimers by C—H...O interactions. Aromatic π–π stacking between the naphthalene ring systems lead to the formation of chains along [001]. A Hirshfeld surface analysis was undertaken to investigate and quantify the intermolecular interactions. In addition, energy frameworks were used to examine the cooperative effect of these intermolecular interactions across the crystal, showing dispersion energy to be the most influential factor in the crystal organization of the compound.