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ISSN: 2056-9890

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

aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 22 July 2012; accepted 31 July 2012; online 4 August 2012)

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[Ravikumar, K., Rajan, S. S., Pattabhi, V. & Gabe, E. J. (1985). Acta Cryst. C41, 280-282.]).

[Scheme 1]

Experimental

Crystal data
  • C18H21NO3

  • Mr = 299.36

  • Monoclinic, P 21

  • 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[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.986

  • 6522 measured reflections

  • 1681 independent reflections

  • 1029 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.142

  • S = 1.02

  • 1681 reflections

  • 201 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.19 e Å−3

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 DA D—H⋯A
C7—H7⋯Cg3i 0.93 2.98 3.679 (5) 133
C15—H15ACg3ii 0.97 2.95 3.756 (5) 141
C16—H16ACg2ii 0.97 2.79 3.675 (5) 153
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z]; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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 Uiso(H) = k × Ueq(C), where k = 1.5 for methyl and = 1.2 for other H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Spek, 2009).

Figures top
[Figure 1] Fig. 1. 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 top
Crystal data top
C18H21NO3F(000) = 320
Mr = 299.36Dx = 1.268 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1029 reflections
a = 9.5947 (15) Åθ = 1.7–26.0°
b = 6.6293 (8) ŵ = 0.09 mm1
c = 12.340 (2) ÅT = 296 K
β = 92.221 (5)°Prism, colourless
V = 784.3 (2) Å30.33 × 0.23 × 0.17 mm
Z = 2
Data collection top
Bruker Kappa APEXII CCD
diffractometer
1681 independent reflections
Radiation source: fine-focus sealed tube1029 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 8.00 pixels mm-1θmax = 26.0°, θmin = 1.7°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 87
Tmin = 0.972, Tmax = 0.986l = 1515
6522 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0707P)2]
where P = (Fo2 + 2Fc2)/3
1681 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C18H21NO3V = 784.3 (2) Å3
Mr = 299.36Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.5947 (15) ŵ = 0.09 mm1
b = 6.6293 (8) ÅT = 296 K
c = 12.340 (2) Å0.33 × 0.23 × 0.17 mm
β = 92.221 (5)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
1681 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1029 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.986Rint = 0.047
6522 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0541 restraint
wR(F2) = 0.142H-atom parameters constrained
S = 1.02Δρmax = 0.18 e Å3
1681 reflectionsΔρmin = 0.19 e Å3
201 parameters
Special details top

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/Ueq
O11.3551 (3)0.2256 (4)0.0544 (3)0.0602 (11)
O20.6416 (3)0.3801 (5)0.3319 (3)0.0829 (16)
O30.2888 (3)0.8958 (5)0.3399 (3)0.0884 (14)
N10.5373 (4)0.6801 (5)0.3199 (3)0.0609 (14)
C10.9024 (4)0.5452 (6)0.2733 (3)0.0465 (16)
C20.9648 (4)0.6297 (6)0.1868 (3)0.0460 (14)
C31.0673 (4)0.5277 (6)0.1281 (3)0.0425 (14)
C41.1077 (4)0.3316 (6)0.1603 (3)0.0436 (16)
C51.0438 (4)0.2470 (6)0.2511 (4)0.0513 (14)
C60.9445 (4)0.3484 (6)0.3041 (4)0.0530 (17)
C71.1283 (4)0.6141 (7)0.0367 (4)0.0511 (14)
C81.2234 (4)0.5100 (7)0.0192 (3)0.0533 (17)
C91.2619 (4)0.3142 (7)0.0120 (4)0.0496 (16)
C101.2068 (4)0.2259 (6)0.1004 (3)0.0482 (14)
C111.3915 (5)0.0220 (7)0.0360 (5)0.081 (2)
C120.7953 (4)0.6652 (7)0.3314 (4)0.0522 (16)
C130.8407 (5)0.7042 (9)0.4502 (4)0.079 (2)
C140.6520 (4)0.5624 (7)0.3276 (4)0.0573 (19)
C150.3990 (4)0.5883 (8)0.3042 (5)0.083 (2)
C160.2948 (5)0.6889 (8)0.3671 (5)0.074 (2)
C170.4198 (5)0.9877 (8)0.3664 (6)0.093 (3)
C180.5324 (5)0.8992 (7)0.3048 (5)0.076 (2)
H20.939010.759490.165550.0550*
H51.070440.119080.274940.0613*
H60.902870.286880.362300.0634*
H71.102870.743540.014610.0612*
H81.263570.569160.078750.0638*
H101.234230.096570.121160.0575*
H11A1.435600.008460.034770.1220*
H11B1.454620.021190.089830.1220*
H11C1.308900.059850.040480.1220*
H120.785190.796150.295040.0627*
H13A0.846080.578380.488620.1191*
H13B0.773820.790420.482990.1191*
H13C0.930470.768260.453280.1191*
H15A0.370860.594220.227930.0991*
H15B0.404140.447410.325180.0991*
H16A0.204340.627280.352440.0888*
H16B0.318280.674020.443870.0888*
H17A0.441300.971540.443350.1111*
H17B0.413811.131060.351080.1111*
H18A0.517250.929880.228380.0903*
H18B0.620880.957830.328910.0903*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0555 (18)0.053 (2)0.073 (2)0.0001 (15)0.0157 (16)0.0012 (16)
O20.052 (2)0.039 (2)0.158 (4)0.0020 (15)0.009 (2)0.000 (2)
O30.062 (2)0.056 (2)0.147 (3)0.0147 (17)0.002 (2)0.007 (2)
N10.044 (2)0.037 (2)0.102 (3)0.0007 (17)0.007 (2)0.0035 (19)
C10.036 (2)0.050 (3)0.053 (3)0.000 (2)0.004 (2)0.003 (2)
C20.040 (2)0.037 (2)0.060 (3)0.0007 (19)0.010 (2)0.003 (2)
C30.037 (2)0.042 (2)0.048 (3)0.0008 (19)0.0062 (19)0.0000 (19)
C40.036 (2)0.046 (3)0.048 (3)0.0011 (18)0.007 (2)0.004 (2)
C50.048 (2)0.038 (2)0.068 (3)0.0066 (19)0.003 (2)0.008 (2)
C60.054 (3)0.050 (3)0.055 (3)0.004 (2)0.001 (2)0.010 (2)
C70.046 (2)0.040 (2)0.067 (3)0.004 (2)0.003 (2)0.007 (2)
C80.052 (3)0.054 (3)0.054 (3)0.009 (2)0.004 (2)0.006 (2)
C90.044 (2)0.049 (3)0.056 (3)0.006 (2)0.003 (2)0.009 (2)
C100.042 (2)0.044 (2)0.058 (3)0.0044 (19)0.004 (2)0.001 (2)
C110.079 (4)0.063 (4)0.104 (4)0.026 (3)0.037 (3)0.016 (3)
C120.042 (2)0.049 (3)0.066 (3)0.002 (2)0.007 (2)0.004 (2)
C130.064 (3)0.099 (4)0.075 (4)0.007 (3)0.000 (3)0.029 (3)
C140.048 (3)0.043 (3)0.081 (4)0.001 (2)0.004 (2)0.003 (2)
C150.044 (3)0.060 (4)0.144 (5)0.004 (2)0.002 (3)0.012 (3)
C160.046 (3)0.065 (4)0.111 (4)0.001 (3)0.001 (3)0.003 (3)
C170.067 (4)0.048 (3)0.165 (6)0.000 (3)0.023 (4)0.010 (4)
C180.062 (3)0.047 (3)0.119 (5)0.007 (2)0.023 (3)0.012 (3)
Geometric parameters (Å, º) top
O1—C91.369 (5)C17—C181.467 (8)
O1—C111.410 (5)C2—H20.9300
O2—C141.214 (6)C5—H50.9300
O3—C161.413 (6)C6—H60.9300
O3—C171.423 (6)C7—H70.9300
N1—C141.349 (6)C8—H80.9300
N1—C151.466 (6)C10—H100.9300
N1—C181.465 (6)C11—H11A0.9600
C1—C21.364 (5)C11—H11B0.9600
C1—C61.413 (6)C11—H11C0.9600
C1—C121.503 (6)C12—H120.9800
C2—C31.416 (5)C13—H13A0.9600
C3—C41.409 (6)C13—H13B0.9600
C3—C71.412 (6)C13—H13C0.9600
C4—C51.414 (6)C15—H15A0.9700
C4—C101.413 (5)C15—H15B0.9700
C5—C61.355 (6)C16—H16A0.9700
C7—C81.354 (6)C16—H16B0.9700
C8—C91.400 (6)C17—H17A0.9700
C9—C101.363 (6)C17—H17B0.9700
C12—C131.535 (7)C18—H18A0.9700
C12—C141.534 (6)C18—H18B0.9700
C15—C161.452 (7)
C9—O1—C11118.5 (4)C8—C7—H7120.00
C16—O3—C17109.5 (4)C7—C8—H8120.00
C14—N1—C15120.1 (4)C9—C8—H8120.00
C14—N1—C18127.2 (4)C4—C10—H10120.00
C15—N1—C18111.7 (4)C9—C10—H10120.00
C2—C1—C6117.4 (4)O1—C11—H11A109.00
C2—C1—C12119.0 (4)O1—C11—H11B109.00
C6—C1—C12123.6 (4)O1—C11—H11C109.00
C1—C2—C3122.6 (4)H11A—C11—H11B110.00
C2—C3—C4119.0 (3)H11A—C11—H11C109.00
C2—C3—C7122.2 (4)H11B—C11—H11C109.00
C4—C3—C7118.8 (4)C1—C12—H12108.00
C3—C4—C5117.8 (3)C13—C12—H12108.00
C3—C4—C10119.6 (3)C14—C12—H12108.00
C5—C4—C10122.6 (4)C12—C13—H13A109.00
C4—C5—C6121.4 (4)C12—C13—H13B109.00
C1—C6—C5121.8 (4)C12—C13—H13C109.00
C3—C7—C8120.6 (4)H13A—C13—H13B109.00
C7—C8—C9120.6 (4)H13A—C13—H13C110.00
O1—C9—C8113.9 (4)H13B—C13—H13C109.00
O1—C9—C10125.3 (4)N1—C15—H15A109.00
C8—C9—C10120.8 (4)N1—C15—H15B109.00
C4—C10—C9119.7 (4)C16—C15—H15A109.00
C1—C12—C13111.8 (4)C16—C15—H15B109.00
C1—C12—C14112.3 (4)H15A—C15—H15B108.00
C13—C12—C14109.0 (4)O3—C16—H16A110.00
O2—C14—N1120.7 (4)O3—C16—H16B110.00
O2—C14—C12121.1 (4)C15—C16—H16A110.00
N1—C14—C12118.2 (4)C15—C16—H16B110.00
N1—C15—C16112.2 (4)H16A—C16—H16B108.00
O3—C16—C15110.0 (4)O3—C17—H17A109.00
O3—C17—C18111.8 (5)O3—C17—H17B109.00
N1—C18—C17110.6 (4)C18—C17—H17A109.00
C1—C2—H2119.00C18—C17—H17B109.00
C3—C2—H2119.00H17A—C17—H17B108.00
C4—C5—H5119.00N1—C18—H18A110.00
C6—C5—H5119.00N1—C18—H18B110.00
C1—C6—H6119.00C17—C18—H18A110.00
C5—C6—H6119.00C17—C18—H18B110.00
C3—C7—H7120.00H18A—C18—H18B108.00
C11—O1—C9—C104.6 (6)C4—C3—C7—C80.3 (6)
C11—O1—C9—C8174.5 (4)C7—C3—C4—C100.5 (6)
C17—O3—C16—C1562.1 (6)C2—C3—C7—C8178.3 (4)
C16—O3—C17—C1861.9 (6)C7—C3—C4—C5179.1 (4)
C18—N1—C15—C1650.5 (6)C2—C3—C4—C50.5 (6)
C14—N1—C15—C16140.2 (5)C2—C3—C4—C10178.1 (4)
C18—N1—C14—O2174.4 (5)C3—C4—C5—C61.6 (6)
C18—N1—C14—C125.9 (7)C3—C4—C10—C90.2 (6)
C15—N1—C14—O27.0 (7)C5—C4—C10—C9178.3 (4)
C15—N1—C18—C1748.5 (6)C10—C4—C5—C6177.0 (4)
C14—N1—C18—C17143.2 (5)C4—C5—C6—C11.7 (7)
C15—N1—C14—C12173.4 (4)C3—C7—C8—C90.6 (6)
C6—C1—C12—C1461.7 (5)C7—C8—C9—C101.4 (6)
C6—C1—C2—C30.4 (6)C7—C8—C9—O1177.8 (4)
C2—C1—C12—C13118.0 (4)O1—C9—C10—C4177.9 (4)
C6—C1—C12—C1361.1 (5)C8—C9—C10—C41.1 (6)
C12—C1—C6—C5178.4 (4)C13—C12—C14—N191.2 (5)
C2—C1—C12—C14119.2 (4)C13—C12—C14—O288.5 (6)
C2—C1—C6—C50.7 (6)C1—C12—C14—N1144.5 (4)
C12—C1—C2—C3179.6 (4)C1—C12—C14—O235.8 (6)
C1—C2—C3—C7178.1 (4)N1—C15—C16—O357.1 (6)
C1—C2—C3—C40.5 (6)O3—C17—C18—N154.8 (6)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C1–C6 and C3/C4/C7–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7···Cg3i0.932.983.679 (5)133
C15—H15A···Cg3ii0.972.953.756 (5)141
C16—H16A···Cg2ii0.972.793.675 (5)153
Symmetry codes: (i) x+2, y+1/2, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC18H21NO3
Mr299.36
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)9.5947 (15), 6.6293 (8), 12.340 (2)
β (°) 92.221 (5)
V3)784.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.33 × 0.23 × 0.17
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.972, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
6522, 1681, 1029
Rint0.047
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.142, 1.02
No. of reflections1681
No. of parameters201
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C1–C6 and C3/C4/C7–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7···Cg3i0.932.983.679 (5)133
C15—H15A···Cg3ii0.972.953.756 (5)141
C16—H16A···Cg2ii0.972.793.675 (5)153
Symmetry codes: (i) x+2, y+1/2, z; (ii) x1, y, z.
 

Acknowledgements

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.

References

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