organic compounds
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
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
of the related compound, naproxen [systematic name: (+)-2-(6-methoxy-2-naphthyl)-propionic acid], see: RavikumarExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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.
Supporting information
10.1107/S1600536812034083/su2485sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034083/su2485Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034083/su2485Isup3.cml
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
[Yield: 65.0%, M.p.: 388 K].In the final cycles of
in the absence of significant 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.Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. A view of the molecular structure of the title molecule, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level. |
C18H21NO3 | F(000) = 320 |
Mr = 299.36 | Dx = 1.268 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1029 reflections |
a = 9.5947 (15) Å | θ = 1.7–26.0° |
b = 6.6293 (8) Å | µ = 0.09 mm−1 |
c = 12.340 (2) Å | T = 296 K |
β = 92.221 (5)° | Prism, colourless |
V = 784.3 (2) Å3 | 0.33 × 0.23 × 0.17 mm |
Z = 2 |
Bruker Kappa APEXII CCD diffractometer | 1681 independent reflections |
Radiation source: fine-focus sealed tube | 1029 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.00 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −8→7 |
Tmin = 0.972, Tmax = 0.986 | l = −15→15 |
6522 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-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 parameters | Δρmax = 0.18 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
C18H21NO3 | V = 784.3 (2) Å3 |
Mr = 299.36 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.5947 (15) Å | µ = 0.09 mm−1 |
b = 6.6293 (8) Å | T = 296 K |
c = 12.340 (2) Å | 0.33 × 0.23 × 0.17 mm |
β = 92.221 (5)° |
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 = 0.986 | Rint = 0.047 |
6522 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 1 restraint |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.18 e Å−3 |
1681 reflections | Δρmin = −0.19 e Å−3 |
201 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.3551 (3) | 0.2256 (4) | −0.0544 (3) | 0.0602 (11) | |
O2 | 0.6416 (3) | 0.3801 (5) | 0.3319 (3) | 0.0829 (16) | |
O3 | 0.2888 (3) | 0.8958 (5) | 0.3399 (3) | 0.0884 (14) | |
N1 | 0.5373 (4) | 0.6801 (5) | 0.3199 (3) | 0.0609 (14) | |
C1 | 0.9024 (4) | 0.5452 (6) | 0.2733 (3) | 0.0465 (16) | |
C2 | 0.9648 (4) | 0.6297 (6) | 0.1868 (3) | 0.0460 (14) | |
C3 | 1.0673 (4) | 0.5277 (6) | 0.1281 (3) | 0.0425 (14) | |
C4 | 1.1077 (4) | 0.3316 (6) | 0.1603 (3) | 0.0436 (16) | |
C5 | 1.0438 (4) | 0.2470 (6) | 0.2511 (4) | 0.0513 (14) | |
C6 | 0.9445 (4) | 0.3484 (6) | 0.3041 (4) | 0.0530 (17) | |
C7 | 1.1283 (4) | 0.6141 (7) | 0.0367 (4) | 0.0511 (14) | |
C8 | 1.2234 (4) | 0.5100 (7) | −0.0192 (3) | 0.0533 (17) | |
C9 | 1.2619 (4) | 0.3142 (7) | 0.0120 (4) | 0.0496 (16) | |
C10 | 1.2068 (4) | 0.2259 (6) | 0.1004 (3) | 0.0482 (14) | |
C11 | 1.3915 (5) | 0.0220 (7) | −0.0360 (5) | 0.081 (2) | |
C12 | 0.7953 (4) | 0.6652 (7) | 0.3314 (4) | 0.0522 (16) | |
C13 | 0.8407 (5) | 0.7042 (9) | 0.4502 (4) | 0.079 (2) | |
C14 | 0.6520 (4) | 0.5624 (7) | 0.3276 (4) | 0.0573 (19) | |
C15 | 0.3990 (4) | 0.5883 (8) | 0.3042 (5) | 0.083 (2) | |
C16 | 0.2948 (5) | 0.6889 (8) | 0.3671 (5) | 0.074 (2) | |
C17 | 0.4198 (5) | 0.9877 (8) | 0.3664 (6) | 0.093 (3) | |
C18 | 0.5324 (5) | 0.8992 (7) | 0.3048 (5) | 0.076 (2) | |
H2 | 0.93901 | 0.75949 | 0.16555 | 0.0550* | |
H5 | 1.07044 | 0.11908 | 0.27494 | 0.0613* | |
H6 | 0.90287 | 0.28688 | 0.36230 | 0.0634* | |
H7 | 1.10287 | 0.74354 | 0.01461 | 0.0612* | |
H8 | 1.26357 | 0.56916 | −0.07875 | 0.0638* | |
H10 | 1.23423 | 0.09657 | 0.12116 | 0.0575* | |
H11A | 1.43560 | 0.00846 | 0.03477 | 0.1220* | |
H11B | 1.45462 | −0.02119 | −0.08983 | 0.1220* | |
H11C | 1.30890 | −0.05985 | −0.04048 | 0.1220* | |
H12 | 0.78519 | 0.79615 | 0.29504 | 0.0627* | |
H13A | 0.84608 | 0.57838 | 0.48862 | 0.1191* | |
H13B | 0.77382 | 0.79042 | 0.48299 | 0.1191* | |
H13C | 0.93047 | 0.76826 | 0.45328 | 0.1191* | |
H15A | 0.37086 | 0.59422 | 0.22793 | 0.0991* | |
H15B | 0.40414 | 0.44741 | 0.32518 | 0.0991* | |
H16A | 0.20434 | 0.62728 | 0.35244 | 0.0888* | |
H16B | 0.31828 | 0.67402 | 0.44387 | 0.0888* | |
H17A | 0.44130 | 0.97154 | 0.44335 | 0.1111* | |
H17B | 0.41381 | 1.13106 | 0.35108 | 0.1111* | |
H18A | 0.51725 | 0.92988 | 0.22838 | 0.0903* | |
H18B | 0.62088 | 0.95783 | 0.32891 | 0.0903* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0555 (18) | 0.053 (2) | 0.073 (2) | 0.0001 (15) | 0.0157 (16) | −0.0012 (16) |
O2 | 0.052 (2) | 0.039 (2) | 0.158 (4) | 0.0020 (15) | 0.009 (2) | 0.000 (2) |
O3 | 0.062 (2) | 0.056 (2) | 0.147 (3) | 0.0147 (17) | 0.002 (2) | 0.007 (2) |
N1 | 0.044 (2) | 0.037 (2) | 0.102 (3) | 0.0007 (17) | 0.007 (2) | −0.0035 (19) |
C1 | 0.036 (2) | 0.050 (3) | 0.053 (3) | 0.000 (2) | −0.004 (2) | −0.003 (2) |
C2 | 0.040 (2) | 0.037 (2) | 0.060 (3) | −0.0007 (19) | −0.010 (2) | 0.003 (2) |
C3 | 0.037 (2) | 0.042 (2) | 0.048 (3) | 0.0008 (19) | −0.0062 (19) | 0.0000 (19) |
C4 | 0.036 (2) | 0.046 (3) | 0.048 (3) | −0.0011 (18) | −0.007 (2) | 0.004 (2) |
C5 | 0.048 (2) | 0.038 (2) | 0.068 (3) | 0.0066 (19) | 0.003 (2) | 0.008 (2) |
C6 | 0.054 (3) | 0.050 (3) | 0.055 (3) | 0.004 (2) | 0.001 (2) | 0.010 (2) |
C7 | 0.046 (2) | 0.040 (2) | 0.067 (3) | −0.004 (2) | −0.003 (2) | 0.007 (2) |
C8 | 0.052 (3) | 0.054 (3) | 0.054 (3) | −0.009 (2) | 0.004 (2) | 0.006 (2) |
C9 | 0.044 (2) | 0.049 (3) | 0.056 (3) | −0.006 (2) | 0.003 (2) | −0.009 (2) |
C10 | 0.042 (2) | 0.044 (2) | 0.058 (3) | 0.0044 (19) | −0.004 (2) | 0.001 (2) |
C11 | 0.079 (4) | 0.063 (4) | 0.104 (4) | 0.026 (3) | 0.037 (3) | 0.016 (3) |
C12 | 0.042 (2) | 0.049 (3) | 0.066 (3) | 0.002 (2) | 0.007 (2) | −0.004 (2) |
C13 | 0.064 (3) | 0.099 (4) | 0.075 (4) | −0.007 (3) | 0.000 (3) | −0.029 (3) |
C14 | 0.048 (3) | 0.043 (3) | 0.081 (4) | 0.001 (2) | 0.004 (2) | −0.003 (2) |
C15 | 0.044 (3) | 0.060 (4) | 0.144 (5) | −0.004 (2) | 0.002 (3) | −0.012 (3) |
C16 | 0.046 (3) | 0.065 (4) | 0.111 (4) | −0.001 (3) | −0.001 (3) | 0.003 (3) |
C17 | 0.067 (4) | 0.048 (3) | 0.165 (6) | 0.000 (3) | 0.023 (4) | −0.010 (4) |
C18 | 0.062 (3) | 0.047 (3) | 0.119 (5) | 0.007 (2) | 0.023 (3) | 0.012 (3) |
O1—C9 | 1.369 (5) | C17—C18 | 1.467 (8) |
O1—C11 | 1.410 (5) | C2—H2 | 0.9300 |
O2—C14 | 1.214 (6) | C5—H5 | 0.9300 |
O3—C16 | 1.413 (6) | C6—H6 | 0.9300 |
O3—C17 | 1.423 (6) | C7—H7 | 0.9300 |
N1—C14 | 1.349 (6) | C8—H8 | 0.9300 |
N1—C15 | 1.466 (6) | C10—H10 | 0.9300 |
N1—C18 | 1.465 (6) | C11—H11A | 0.9600 |
C1—C2 | 1.364 (5) | C11—H11B | 0.9600 |
C1—C6 | 1.413 (6) | C11—H11C | 0.9600 |
C1—C12 | 1.503 (6) | C12—H12 | 0.9800 |
C2—C3 | 1.416 (5) | C13—H13A | 0.9600 |
C3—C4 | 1.409 (6) | C13—H13B | 0.9600 |
C3—C7 | 1.412 (6) | C13—H13C | 0.9600 |
C4—C5 | 1.414 (6) | C15—H15A | 0.9700 |
C4—C10 | 1.413 (5) | C15—H15B | 0.9700 |
C5—C6 | 1.355 (6) | C16—H16A | 0.9700 |
C7—C8 | 1.354 (6) | C16—H16B | 0.9700 |
C8—C9 | 1.400 (6) | C17—H17A | 0.9700 |
C9—C10 | 1.363 (6) | C17—H17B | 0.9700 |
C12—C13 | 1.535 (7) | C18—H18A | 0.9700 |
C12—C14 | 1.534 (6) | C18—H18B | 0.9700 |
C15—C16 | 1.452 (7) | ||
C9—O1—C11 | 118.5 (4) | C8—C7—H7 | 120.00 |
C16—O3—C17 | 109.5 (4) | C7—C8—H8 | 120.00 |
C14—N1—C15 | 120.1 (4) | C9—C8—H8 | 120.00 |
C14—N1—C18 | 127.2 (4) | C4—C10—H10 | 120.00 |
C15—N1—C18 | 111.7 (4) | C9—C10—H10 | 120.00 |
C2—C1—C6 | 117.4 (4) | O1—C11—H11A | 109.00 |
C2—C1—C12 | 119.0 (4) | O1—C11—H11B | 109.00 |
C6—C1—C12 | 123.6 (4) | O1—C11—H11C | 109.00 |
C1—C2—C3 | 122.6 (4) | H11A—C11—H11B | 110.00 |
C2—C3—C4 | 119.0 (3) | H11A—C11—H11C | 109.00 |
C2—C3—C7 | 122.2 (4) | H11B—C11—H11C | 109.00 |
C4—C3—C7 | 118.8 (4) | C1—C12—H12 | 108.00 |
C3—C4—C5 | 117.8 (3) | C13—C12—H12 | 108.00 |
C3—C4—C10 | 119.6 (3) | C14—C12—H12 | 108.00 |
C5—C4—C10 | 122.6 (4) | C12—C13—H13A | 109.00 |
C4—C5—C6 | 121.4 (4) | C12—C13—H13B | 109.00 |
C1—C6—C5 | 121.8 (4) | C12—C13—H13C | 109.00 |
C3—C7—C8 | 120.6 (4) | H13A—C13—H13B | 109.00 |
C7—C8—C9 | 120.6 (4) | H13A—C13—H13C | 110.00 |
O1—C9—C8 | 113.9 (4) | H13B—C13—H13C | 109.00 |
O1—C9—C10 | 125.3 (4) | N1—C15—H15A | 109.00 |
C8—C9—C10 | 120.8 (4) | N1—C15—H15B | 109.00 |
C4—C10—C9 | 119.7 (4) | C16—C15—H15A | 109.00 |
C1—C12—C13 | 111.8 (4) | C16—C15—H15B | 109.00 |
C1—C12—C14 | 112.3 (4) | H15A—C15—H15B | 108.00 |
C13—C12—C14 | 109.0 (4) | O3—C16—H16A | 110.00 |
O2—C14—N1 | 120.7 (4) | O3—C16—H16B | 110.00 |
O2—C14—C12 | 121.1 (4) | C15—C16—H16A | 110.00 |
N1—C14—C12 | 118.2 (4) | C15—C16—H16B | 110.00 |
N1—C15—C16 | 112.2 (4) | H16A—C16—H16B | 108.00 |
O3—C16—C15 | 110.0 (4) | O3—C17—H17A | 109.00 |
O3—C17—C18 | 111.8 (5) | O3—C17—H17B | 109.00 |
N1—C18—C17 | 110.6 (4) | C18—C17—H17A | 109.00 |
C1—C2—H2 | 119.00 | C18—C17—H17B | 109.00 |
C3—C2—H2 | 119.00 | H17A—C17—H17B | 108.00 |
C4—C5—H5 | 119.00 | N1—C18—H18A | 110.00 |
C6—C5—H5 | 119.00 | N1—C18—H18B | 110.00 |
C1—C6—H6 | 119.00 | C17—C18—H18A | 110.00 |
C5—C6—H6 | 119.00 | C17—C18—H18B | 110.00 |
C3—C7—H7 | 120.00 | H18A—C18—H18B | 108.00 |
C11—O1—C9—C10 | 4.6 (6) | C4—C3—C7—C8 | 0.3 (6) |
C11—O1—C9—C8 | −174.5 (4) | C7—C3—C4—C10 | −0.5 (6) |
C17—O3—C16—C15 | −62.1 (6) | C2—C3—C7—C8 | −178.3 (4) |
C16—O3—C17—C18 | 61.9 (6) | C7—C3—C4—C5 | −179.1 (4) |
C18—N1—C15—C16 | −50.5 (6) | C2—C3—C4—C5 | −0.5 (6) |
C14—N1—C15—C16 | 140.2 (5) | C2—C3—C4—C10 | 178.1 (4) |
C18—N1—C14—O2 | −174.4 (5) | C3—C4—C5—C6 | 1.6 (6) |
C18—N1—C14—C12 | 5.9 (7) | C3—C4—C10—C9 | −0.2 (6) |
C15—N1—C14—O2 | −7.0 (7) | C5—C4—C10—C9 | 178.3 (4) |
C15—N1—C18—C17 | 48.5 (6) | C10—C4—C5—C6 | −177.0 (4) |
C14—N1—C18—C17 | −143.2 (5) | C4—C5—C6—C1 | −1.7 (7) |
C15—N1—C14—C12 | 173.4 (4) | C3—C7—C8—C9 | 0.6 (6) |
C6—C1—C12—C14 | −61.7 (5) | C7—C8—C9—C10 | −1.4 (6) |
C6—C1—C2—C3 | 0.4 (6) | C7—C8—C9—O1 | 177.8 (4) |
C2—C1—C12—C13 | −118.0 (4) | O1—C9—C10—C4 | −177.9 (4) |
C6—C1—C12—C13 | 61.1 (5) | C8—C9—C10—C4 | 1.1 (6) |
C12—C1—C6—C5 | −178.4 (4) | C13—C12—C14—N1 | 91.2 (5) |
C2—C1—C12—C14 | 119.2 (4) | C13—C12—C14—O2 | −88.5 (6) |
C2—C1—C6—C5 | 0.7 (6) | C1—C12—C14—N1 | −144.5 (4) |
C12—C1—C2—C3 | 179.6 (4) | C1—C12—C14—O2 | 35.8 (6) |
C1—C2—C3—C7 | 178.1 (4) | N1—C15—C16—O3 | 57.1 (6) |
C1—C2—C3—C4 | −0.5 (6) | O3—C17—C18—N1 | −54.8 (6) |
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 |
Symmetry codes: (i) −x+2, y+1/2, −z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H21NO3 |
Mr | 299.36 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 9.5947 (15), 6.6293 (8), 12.340 (2) |
β (°) | 92.221 (5) |
V (Å3) | 784.3 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.33 × 0.23 × 0.17 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.972, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6522, 1681, 1029 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.142, 1.02 |
No. of reflections | 1681 |
No. of parameters | 201 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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 |
Symmetry codes: (i) −x+2, y+1/2, −z; (ii) x−1, 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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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).