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

Li-Jin Shu

doi:10.1107/S1600536811021726

. 2011 Jun 18;67(Pt 7):o1681. doi: 10.1107/S1600536811021726

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

Li-Jin Shu ^a,^*

PMCID: PMC3151918 PMID: 21837079

Abstract

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.

Related literature

For related structures, see: Devi & Bhuyan (2004 ▶); Domling & Ugi (2000 ▶); Fu et al. (2009 ▶). For multi-component reactions, see: Hulme & Gore (2003 ▶); Ugi (1962 ▶).

Experimental

Crystal data

C₂₁H₂₀ClNO₂
M _r = 353.83
Monoclinic,
a = 14.1896 (18) Å
b = 15.881 (2) Å
c = 10.3998 (10) Å
β = 132.13 (2)°
V = 1738.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.89, T _max = 1.00
7216 measured reflections
3127 independent reflections
2050 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.085
wR(F ²) = 0.240
S = 0.99
3127 reflections
226 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ▶), 1551 Friedel pairs
Flack parameter: 0.07 (16)

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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021726/xu5238sup1.cif

e-67-o1681-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021726/xu5238Isup2.hkl

e-67-o1681-Isup2.hkl^{(153.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C3–C8 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.97	2.649 (6)	139
C21—H21A⋯Cgⁱ	0.93	2.87	3.770 (7)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a start-up grant from Hangzhou Normal University, China.

supplementary crystallographic information

Comment

Multi-component reactions (MCRs) (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.