(8-Bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone

In the title compound, C19H14BrClO3, the naphthalene ring system and the benzene ring make a dihedral angle of 77.36 (10)°. The conformation around the central C=O group is such that the C=O bond vector forms a larger angle to the plane of the naphthalene ring system than to the plane of the benzene ring, viz. 75.73 (15)° versus 2.33 (17)°. In the crystal structure, a π–π interaction is formed between naphthalene ring systems, with a centroid–centroid distance of 3.8363 (14) Å and a lateral offset of 1.606 Å. Intermolecular C—H⋯Br and C—H⋯O hydrogen bonds and a C—H⋯π contact are present in the crystal structure.

In the title compound, C 19 H 14 BrClO 3 , the naphthalene ring system and the benzene ring make a dihedral angle of 77.36 (10) . The conformation around the central C O group is such that the C O bond vector forms a larger angle to the plane of the naphthalene ring system than to the plane of the benzene ring, viz. 75.73 (15) versus 2.33 (17) . In the crystal structure, ainteraction is formed between naphthalene ring systems, with a centroid-centroid distance of 3.8363 (14) Å and a lateral offset of 1.606 Å . Intermolecular C-HÁ Á ÁBr and C-HÁ Á ÁO hydrogen bonds and a C-HÁ Á Á contact are present in the crystal structure.
An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is shown in Fig. 1. In the molecule of (I), the dihedral angle between the benzene ring (C12-C17) and the naphthalene ring (C1-C10) is 77.36 (10)°. The C═O bond vector and the least-squares plane of the benzene ring are almost coplanar [2.33 (17)°]. By contrast, the C═O bond vector and the least-squares plane of the naphthalene ring are largely twisted [75.73 (15)°]. The conformation of these groups resembles to that of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene.
In the crystal structure, all H atoms belonging the methoxy group in the 7-position of naphthalene ring, interact with adjacent molecule constructing intermolecular C-H···Br, C-H···O hydrogen bonds and C-H···π contact, respectively (Table 1) Table 1). Additionally, the π systems of the C5-C10 ring (with centroid Cg2) in the naphthalene group are exactly parallel. The perpendicular distance between these aromatic rings is 3.4840 (10) Å.
The centroid-centroid distance between the parallel aromatic rings is 3.8363 (14) Å, and the lateral offsets are 1.606 Å, indicating the presence of a π-π interaction (Fig. 4).

Refinement
All the H atoms could be located in a difference Fourier map. The C-bound H atoms 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).     supplementary materials sup-4

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large 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