(4-Bromophenyl)(2,7-dimethoxy-1-naphthyl)methanone

In the title compound, C19H15BrO3, the dihedral angle between the naphthalene ring system and the benzene ring is 72.02 (9)°. The bridging carbonyl C—C(=O)—C plane makes dihedral angles of 70.88 (10) and 1.87 (12)°, respectively, with the naphthalene ring system and the benzene ring. In the crystal, two types of weak intermolecular C—H⋯O interactions and a short Br⋯C contact [3.345 (2) Å] are observed.


Comment
In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009).
The molecular structure of the title compound is displayed in Fig. 1. The 4-bromophenyl group is out of the plane of the naphthalene ring. The dihedral angle between the best planes of the bromophenyl ring (C12-C17) and the naphthalene ring (C1-C10) is 72.02 (9)°. The carbonyl group and the 4-bromophenyl group have almost coplanar configuration [O3-C11-C12-C13 torsion angle = 2.5 (3)°]. On the other hand, the carbonyl group makes torsion angle of 70.3 (3)°w ith the naphthalene ring plane.
In the crystal structure, the molecular packing of the title compound is stabilized mainly by van der Waals interactions.

Refinement
All H atoms were found in a difference map and were subsequently refined as riding atoms, with C-H = 0.95 (aromatic) and 0.98 (methyl) Å, and with U iso (H) = 1.2U eq (C). Fig. 1. Molecular structure with displacement ellipsoids at 50% probability.     as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq