2,9-Dimethyl-7-phenyl-N-(4-methylphenyl)dibenzo[b,h][1,6]naphthyridin-6-amine

Abstract

The title compound, C31H25N3, was synthesized from 6,4′,4′′-trimethyl-2,4-bis(N-phenylamino)quinoline and is the first structural example containing a phenyl and phenylamino fragment attached to a fused dibenzo[1,6]naphthyridine moiety. The fused tetracyclic ring system is essentially planar [r.m.s. deviation = 0.08 (3) Å]. The phenyl ring and the phenylamino group are inclined by 82.68 (6) and 35.31 (5)°, respectively, to the mean plane of the fused tetracyclic ring system. A weak intramolecular N—H...π(arene) interaction may in part influence the conformation of the molecule. In the crystal, molecules are linked by weak intermolecular C—H...N hydrogen bonds into centrosymmetric dimers. Additional stabilization is provided by weak C—H...π and π–π stacking interactions [centroid–centroid distances = 3.834 (2) and 3.898 (1) Å].