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

Abstract

The title compound, C(31)H(25)N(3), was synthesized from 6,4',4''-trimethyl-2,4-bis-(N-phenyl-amino)-quinoline and is the first structural example containing a phenyl and phenyl-amino fragment attached to a fused dibenzo[1,6]naphthyridine moiety. The fused tetra-cyclic ring system is essentially planar [r.m.s. deviation = 0.08 (3) Å]. The phenyl ring and the phenyl-amino group are inclined by 82.68 (6) and 35.31 (5)°, respectively, to the mean plane of the fused tetra-cyclic ring system. A weak intra-molecular N-H⋯π(arene) inter-action may in part influence the conformation of the mol-ecule. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯N hydrogen bonds into centrosymmetric dimers. Additional stabilization is provided by weak C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.834 (2) and 3.898 (1) Å].

Fig. 1.

The molecular structure of the title compound showing the thermal ellipsoids drawn at the 50% probability level.

Fig. 2.

The crystal packing viewed along the b-axis with weak hydrogen bonds and C-H..π interactions shown as dotted lines