2-(4-Chlorophenyl)naphtho[1,8-de][1,3,2]diazaborinane

Abstract

The title compound, C16H12BClN2, is one in a series of diazaborinanes, derived from 1,8-diaminonaphthalene, featuring substitution at the 1, 2 and 3 positions in the nitrogen-boron heterocycle. The structure deviates from planarity, the torsion angle subtended by the p-chlorophenyl ring relative to the nitrogen–boron heterocycle being −44-.3(3)°. The molecules form infinite chains with strong interactions between the vacant pz orbital of the B atom and the π-system of an adjacent molecule. The distance between the B atom and the 10-atom centroid of an adjacent naphthalene ring is 3.381 (4) Å. One N-H H atom is weakly hydrogen bonded to the Cl atom of an adjacent molecule. This combination of intermolecular interactions leads to the formation of an infinite two-dimensional network perpendicular to the c axis.