(2-Hydroxy-7-methoxynaphthalen-1-yl)(4-methylphenyl)methanone

In the title compound, C19H16O3, an intramolecular O—H⋯O=C hydrogen bond is formed between the hydroxy and carbonyl groups on the naphthalene ring system, resulting in an S(6) ring. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the benzene ring are 27.63 (6) and 47.99 (7)°, respectively. The dihedral angle between the latter planes is 61.39 (5)°. In the crystal, two molecules are connected by pairs of intermolecular O—H⋯O=C hydrogen bonds, forming centrosymmetric dimers with an R 2 2(4) graph-set motif. The molecular packing features C—H⋯π interactions.

In the title compound, C 19 H 16 O 3 , an intramolecular O-HÁ Á ÁO C hydrogen bond is formed between the hydroxy and carbonyl groups on the naphthalene ring system, resulting in an S(6) ring. The angles between the C O bond vector and the least-squares planes of the naphthalene ring system and the benzene ring are 27.63 (6) and 47.99 (7) , respectively. The dihedral angle between the latter planes is 61.39 (5) . In the crystal, two molecules are connected by pairs of intermolecular O-HÁ Á ÁO C hydrogen bonds, forming centrosymmetric dimers with an R 2 2 (4) graph-set motif. The molecular packing features C-HÁ Á Á interactions.
In the crystal structure, O-H···O═C intermolecular hydrogen bonds between the hydroxy group and the carbonyl one on the naphthalene ring (Table 1) form a centrosymmetric dimer (Fig. 2) with a R 2 2 (4) graph set motif (Etter et al., 1990;Bernstein et al., 1995). The molecular packing of (I) is mainly stabilized by intermolecular C-H···π hydrogen bond involving the centroid CT1 of the C5-C10 ring and the centroid CT2 of the C12-C17 phenyl ring. (Table 1).

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 O1 0.39263 (