2-Phenylnaphtho[1,8-de][1,3,2]diazaborinane

Abstract

The title compound, C16H13BN2, is one compound in a series of diazaborinanes featuring substitution at the 1, 2 and 3 positions in the nitrogen–boron heterocycle. The title compound is slightly distorted from planarity, with a dihedral angle of 9.0 (5)° between the mean planes of the naphthalene system and the benzene ring. The m-carbon atom of the benzene ring exhibits the greatest deviation of 0.164 (2) Å from the 19-atom mean plane defined by all non-H atoms. The two N—B—C—C torsion angles are 6.0 (3) and 5.6 (3)°. In the crystal, molecules are linked by π–π interactions into columns, with a distance of 3.92 (3) Å between the naphthalene ring centroids. Adjacent π-stacked columns, co-linear with the b-axis, are linked by C—H...π interactions.