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

Nasirullah; Nazar Ul Islam; M Nawaz Tahir; Ikhtiar Khan; Muhammad Zulfiqar

doi:10.1107/S1600536812034083

. 2012 Aug 4;68(Pt 9):o2636. doi: 10.1107/S1600536812034083

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

Nasirullah ^a, Nazar Ul Islam ^a, M Nawaz Tahir ^b,^*, Ikhtiar Khan ^a, Muhammad Zulfiqar ^b

PMCID: PMC3435663 PMID: 22969536

Abstract

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.

Related literature

For the crystal structure of the related compound, naproxen [systematic name: (+)-2-(6-methoxy-2-naphthyl)-propionic acid], see: Ravikumar et al. (1985 ▶).

Experimental

Crystal data

C₁₈H₂₁NO₃
M _r = 299.36
Monoclinic,
a = 9.5947 (15) Å
b = 6.6293 (8) Å
c = 12.340 (2) Å
β = 92.221 (5)°
V = 784.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.33 × 0.23 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.972, T _max = 0.986
6522 measured reflections
1681 independent reflections
1029 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.142
S = 1.02
1681 reflections
201 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034083/su2485sup1.cif

e-68-o2636-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034083/su2485Isup2.hkl

e-68-o2636-Isup2.hkl^{(81.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034083/su2485Isup3.cml

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

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

Cg2 and Cg3 are the centroids of the C1–C6 and C3/C4/C7–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg3ⁱ	0.93	2.98	3.679 (5)	133
C15—H15A⋯Cg3ⁱⁱ	0.97	2.95	3.756 (5)	141
C16—H16A⋯Cg2ⁱⁱ	0.97	2.79	3.675 (5)	153

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound is the morpholine derivative of Naproxen [(+)-2-(6-methoxy-2-naphthyl)-propionic acid], whose crystal structure has been reported on by (Ravikumar et al., 1985). The title compound was synthesized in order to study its biological properties and we report herein on its synthesis and crystal structure.

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.

In the crystal, molecules are linked via C—H···π interactions (Table 1).

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].