2-(6-Methoxynaphthalen-2-yl)-1-(morpholin-4-yl)propan-1-one

In the title compound, C18H21NO3, the naphthalene group and the basal plane of the morpholine ring (r.m.s. deviations = 0.0177 and 0.0069 Å, respectively) are oriented at a dihedral angle of 44.0 (2)°. In the crystal, molecules are linked by C—H⋯π interactions.

In the title compound, C 18 H 21 NO 3 , the naphthalene group and the basal plane of the morpholine ring (r.m.s. deviations = 0.0177 and 0.0069 Å , respectively) are oriented at a dihedral angle of 44.0 (2) . In the crystal, molecules are linked by C-HÁ Á Á interactions.

Experimental
Cg2 and Cg3 are the centroids of the C1-C6 and C3/C4/C7-C10 rings, respectively. The molecular structure of the title compound is illustrated in Fig. 1. The naphthaline group A (C1-C10) and the basal plane of the morpholine group B (atoms C15-C18) are planar with r.m.s. deviations of 0.0177 Å and 0.0069 Å, respectively. The dihedral angle between planes A/B is 43.97 (23)°. The O1 and C11 atoms of the methoxy group are at a distance of -0.0911 (44) and -0.2335 (74) Å, respectively, from the mean plane of the naphthaline group. The morpholine group has a chair conformation with atoms N1 and O3 at a distance of 0.5827 (79) and -0.6752 (77) Å, respectively, from the basal plane B.

Experimental
A solution of morpholine (0.35 g, 40.2 mmol) in 5 ml of dichloromethane (DCM) was added to a solution of naproxen acid chloride (0.5 g, 20.1 mmol) in DCM (10 ml). The reaction mixture was stirred at room temperature for 3 h. After completion the reaction mixture was filtered and the filtrate concentrated to give the crude product. The product was purified by flash column chromatogrphy using n-hexane: ethyl acetate (50:50). The resulting jelly like product was recystallized from diethyl ether and hexane (1:1) to give the title compound as colourless prism-like crystals, suitable for X-ray diffraction analysis [Yield: 65.0%, M.p.: 388 K].

Refinement
In the final cycles of refinement, in the absence of significant anomalous scattering effects, Friedel pairs were merged and Δf " set to zero. The H atoms were positioned geometrically (C-H = 0.93-0.98 Å) and refined as riding with U iso (H) = k × U eq (C), where k = 1.5 for methyl and = 1.2 for other H-atoms.  A view of the molecular structure of the title molecule, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level.

2-(6-Methoxynaphthalen-2-yl)-1-(morpholin-4-yl)propan-1-one
Crystal data Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1