(7-Dimethylamino-1-hydroxy-3-naphthyl)(morpholino)methanone

In the title compound, C17H20N2O3, the morpholine ring is in a slightly distorted chair form. The crystal structure is stabilized by an intermolecular O—H⋯O hydrogen bond between the H atom of the hydroxyl group and the O atom of a neighbouring carbonyl group. A weak intermolecular C—H⋯π interaction is also present.

In the title compound, C 17 H 20 N 2 O 3 , the morpholine ring is in a slightly distorted chair form. The crystal structure is stabilized by an intermolecular O-HÁ Á ÁO hydrogen bond between the H atom of the hydroxyl group and the O atom of a neighbouring carbonyl group. A weak intermolecular C-HÁ Á Á interaction is also present.

Comment
The synthesis of organic photochromic dyes and their application has become of great interest recently (Gabbutt et al., 2003(Gabbutt et al., , 2004Kumar et al., 1995;Gemert & Selvig, 2000;Nelson et al., 2002. Because they may be useful such as variable optical transmission materials (ophthalmic glasses and lenses) or in potential use such as optical storage (optical disks or memories) (Crano & Guglielmetti, 1999). Here we report the crystal structure of the title compound (Fig. 1). In the title compound, the conformation of the morpholine ring is in a slightly distorted chair form. The crystal packing (Fig. 2) is stabilized by an intermolecular O-H···O hydrogen bond between the H atom of the hydroxyl group and the O atom of a neighbouring C═O unit, with a O1-H1···O2 i ( Table 1). The molecular packing (Fig. 2) is further stabilized by a intermolecular C-H···π interaction between a methyl H atom of the dimethylamino group and the N-bonded benzene ring, with a C17-H17C···Cg ii (Table 1; Cg is the centroid of the C5-C10 benzene ring).

Experimental
The title compound was synthesized from the reaction of 1-hydroxy-7-dimethylamino-3-naphthonic acid (116 g, 0.5 mol) and morpholine (48 g, 1.2 mol) in anhydrous CH 2 Cl 2 for 24 h at room temperature. The reaction was quenched by the addition of water and the organic layer separated, dried over anhydrous MgSO 4 , filtered and concentrated to give the title compound (120 g, yield 81%). Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement
All the Friedel pairs were merged. All hydrogen atoms were placed in calculated positions using a riding model, with C-H = 0.93-0.97 Å, O-H = 0.82 Å, and with U iso (H) = 1.2-1.5 U eq (C, O). Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.  supplementary materials sup-3

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 > 2sigma(F 2 ) is used only for calculating R-factors(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.