1-[(3-Chlorophenyl)(morpholin-4-yl)methyl]naphthalen-2-ol

In the title compound, C21H20ClNO2, the dihedral angle between the naphthylene ring system and the phenyl ring is 77.86 (15)°. The morpholine ring adopts a chair conformation. The hydroxyl group is involved in intramolecular O—H⋯N hydrogen bonding. A weak intermolecular C—H⋯π interaction is present in the crystal structure.

In the title compound, C 21 H 20 ClNO 2 , the dihedral angle between the naphthylene ring system and the phenyl ring is 77.86 (15) . The morpholine ring adopts a chair conformation. The hydroxyl group is involved in intramolecular O-HÁ Á ÁN hydrogen bonding. A weak intermolecular C-HÁ Á Á interaction is present in the crystal structure.
Cg is the centroid of the C3-C8 benzene ring. Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.  (Hulme & Gore, 2003;Ugi, 1962) involving at least three starting materials in a one-pot reaction have attracted considerable attention in terms of saving both energy and raw materials (Devi & Bhuyan, 2004;Fu, et al. 2009). Compared to conventional multi-step organic syntheses, MCRs have merits over multi-step reactions that include the simplicity of a one-pot procedure and the buildup of complex molecules (Domling & Ugi, 2000). We report here the synthesis and crystal structure of the title compound, 1-((3-chlorophenyl)(morpholino)methyl)naphthalen-2-ol.
In the title compound ( Fig. 1) bond lengths and angles have normal values. The dihedral angle between the naphthylene ring system and the benzene ring is 77.86 (15)°. The H atom of hydroxyl is involved in strong intramolecular O-H···N hydrogen bonds (Table 1). Weak intermolecular C-H···π interaction is present in the crystal structure.

Experimental
A dry 50 ml flask was charged with 3-chlorobenzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and morpholine (10 mmol). The mixture was stirred at 373 K for 12 h and then added ethanol (15 ml), after heated under reflux for 1 h, the precipitate was filtered out and washed with ethanol for 3 times to give the title compound. Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution.

Refinement
All the H atoms attached to C atoms were situated into the idealized positions and treated as riding with C-H = 0.93 Å (aromatic), 0.97 Å (methylene) and 0.98 Å (methine) with U iso (H)=1.2U eq (C). The positional parameters of the H atom (O1) was refined freely. And in the last stage of the refinement, it was restrained with the H1-O1 = 0.82 (2)Å), with Fig. 1. A view of the asymmetric unit with the atomic numbering scheme. The displacement ellipsoids were drawn at the 30% probability level. 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.