Ethyl 6-meth­oxy-2-naphthoate

The title compound, C₁₄H₁₄O₃, is a starting compound for the synthesis of non-steroidal anti-inflammatory drugs and is an important substrate in the pharmaceutical industry. Whereas the meth­oxy group is almost coplanar with the naphthyl ring system, the eth­oxy group is significantly twisted out of the plane of the aromatic system [C-O-C-C = -85.31 (15)°].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.039
• wR factor = 0.103
• Data-to-parameter ratio = 14.4

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Related literature

Some related crystal structures such as methyl 7-methoxy-2-naphthoate (Prince et al., 1991), 2-acetylphenyl 1-naphthoate (Goeta et al., 1996), methyl 1-hydroxy-2-naphthoate (Jin & Xiao, 2005), ethyl 3-hydroxy-2-naphthoate (Jin & Jin, 2005) and ethyl 4-acetoxy-6-(dimethylamino)-2-naphthoate (Du et al., 2006) have been reported.

S1. Experimental

A sample of ethyl 6-methoxy-2-naphthoate was obtained from Strides Arco Labs, Mangalore, India. Colourless plates of (I) were obtained by slow evaporation using a mixture (1:1 v/v) of acetone and toluene (m.p.: 359–361 K).

S2. Refinement

The H atoms were found in a difference map, relocated in idelized loations (C—H = 0.95–0.99 Å), and refined as riding with U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(C_methyl). The methyl groups were allowed to rotate but not to tip.

Structure description

Some related crystal structures such as methyl 7-methoxy-2-naphthoate (Prince et al., 1991), 2-acetylphenyl 1-naphthoate (Goeta et al., 1996), methyl 1-hydroxy-2-naphthoate (Jin & Xiao, 2005), ethyl 3-hydroxy-2-naphthoate (Jin & Jin, 2005) and ethyl 4-acetoxy-6-(dimethylamino)-2-naphthoate (Du et al., 2006) have been reported.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. Perspective view of (I) with displacement ellipsoids shown at the 50% probability level (arbitrary spheres for the H atoms).

Ethyl 6-methoxy-2-naphthoate

Crystal data

C14H14O3	F(000) = 976
Mr = 230.25	Dx = 1.323 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 12140 reflections
a = 14.7132 (9) Å	θ = 2.8–26.2°
b = 6.1977 (4) Å	µ = 0.09 mm^−1
c = 25.362 (2) Å	T = 173 K
V = 2312.7 (3) Å^3	Plate, colourless
Z = 8	0.23 × 0.22 × 0.08 mm

Data collection

Stoe IPDSII two-circle diffractometer	1767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.080
Graphite monochromator	θmax = 26.0°, θmin = 2.8°
ω scans	h = −18→18
16684 measured reflections	k = −7→7
2256 independent reflections	l = −31→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0673P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2256 reflections	Δρmax = 0.24 e Å^−3
157 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.36698 (6)	0.29857 (16)	0.09601 (4)	0.0312 (3)
O2	0.39644 (8)	0.39529 (18)	0.43943 (4)	0.0477 (3)
O3	0.41704 (7)	0.72652 (16)	0.40506 (4)	0.0347 (3)
C1	0.37321 (8)	0.3496 (2)	0.14820 (5)	0.0249 (3)
C2	0.34544 (7)	0.2212 (2)	0.18942 (5)	0.0236 (3)
H2	0.3187	0.0844	0.1827	0.028*
C3	0.35702 (7)	0.2947 (2)	0.24217 (5)	0.0222 (3)
C4	0.33292 (8)	0.1654 (2)	0.28634 (5)	0.0254 (3)
H4	0.3067	0.0273	0.2808	0.031*
C5	0.34697 (8)	0.2369 (2)	0.33686 (5)	0.0268 (3)
H5	0.3317	0.1466	0.3658	0.032*
C6	0.38419 (8)	0.4450 (2)	0.34625 (5)	0.0260 (3)
C7	0.40703 (7)	0.5744 (2)	0.30413 (5)	0.0242 (3)
H7	0.4312	0.7141	0.3104	0.029*
C8	0.39510 (7)	0.5030 (2)	0.25179 (5)	0.0224 (3)
C9	0.42163 (8)	0.6307 (2)	0.20785 (5)	0.0270 (3)
H9	0.4464	0.7703	0.2135	0.032*
C10	0.41193 (8)	0.5553 (2)	0.15761 (5)	0.0279 (3)
H10	0.4313	0.6414	0.1287	0.033*
C11	0.34036 (11)	0.0852 (3)	0.08202 (6)	0.0402 (4)
H11A	0.3807	−0.0189	0.0993	0.060*
H11B	0.3444	0.0676	0.0437	0.060*
H11C	0.2776	0.0600	0.0934	0.060*
C12	0.39926 (8)	0.5145 (2)	0.40172 (5)	0.0293 (3)
C13	0.43231 (10)	0.8154 (3)	0.45740 (6)	0.0374 (4)
H13A	0.4711	0.9455	0.4547	0.045*
H13B	0.4647	0.7080	0.4794	0.045*
C14	0.34401 (10)	0.8739 (3)	0.48323 (6)	0.0396 (4)
H14A	0.3104	0.9738	0.4605	0.059*
H14B	0.3561	0.9431	0.5173	0.059*
H14C	0.3079	0.7431	0.4888	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0391 (5)	0.0326 (6)	0.0220 (5)	−0.0022 (4)	−0.0029 (4)	0.0000 (4)
O2	0.0764 (8)	0.0391 (6)	0.0276 (6)	0.0000 (5)	−0.0048 (5)	0.0013 (5)
O3	0.0443 (6)	0.0352 (6)	0.0247 (5)	−0.0072 (4)	0.0025 (4)	−0.0087 (4)
C1	0.0245 (6)	0.0281 (7)	0.0221 (7)	0.0031 (5)	−0.0026 (5)	0.0001 (5)
C2	0.0234 (5)	0.0214 (6)	0.0260 (7)	−0.0012 (5)	−0.0025 (5)	−0.0003 (5)
C3	0.0183 (5)	0.0223 (7)	0.0259 (7)	0.0015 (5)	−0.0013 (4)	0.0003 (5)
C4	0.0259 (6)	0.0230 (7)	0.0274 (7)	−0.0031 (5)	−0.0004 (5)	0.0006 (5)
C5	0.0292 (6)	0.0266 (7)	0.0245 (7)	−0.0007 (5)	0.0013 (5)	0.0036 (5)
C6	0.0232 (6)	0.0295 (7)	0.0251 (7)	0.0034 (5)	0.0001 (5)	−0.0028 (5)
C7	0.0226 (6)	0.0212 (6)	0.0290 (7)	0.0004 (5)	−0.0009 (5)	−0.0019 (5)
C8	0.0189 (5)	0.0215 (7)	0.0267 (7)	0.0013 (5)	−0.0008 (4)	−0.0003 (5)
C9	0.0277 (6)	0.0219 (6)	0.0313 (8)	−0.0026 (5)	−0.0007 (5)	0.0024 (5)
C10	0.0305 (6)	0.0267 (7)	0.0264 (7)	−0.0010 (5)	0.0010 (5)	0.0058 (5)
C11	0.0552 (9)	0.0368 (9)	0.0284 (8)	−0.0070 (7)	−0.0050 (6)	−0.0053 (6)
C12	0.0288 (6)	0.0321 (7)	0.0269 (7)	0.0018 (5)	0.0013 (5)	−0.0022 (6)
C13	0.0407 (7)	0.0443 (9)	0.0271 (8)	−0.0090 (6)	0.0003 (6)	−0.0123 (6)
C14	0.0456 (8)	0.0403 (9)	0.0329 (8)	−0.0011 (7)	0.0040 (6)	−0.0076 (7)

Geometric parameters (Å, º)

O1—C1	1.3642 (16)	C6—C12	1.4880 (19)
O1—C11	1.4240 (18)	C7—C8	1.4102 (18)
O2—C12	1.2089 (18)	C7—H7	0.9500
O3—C12	1.3427 (17)	C8—C9	1.4216 (18)
O3—C13	1.4547 (17)	C9—C10	1.3646 (19)
C1—C2	1.3758 (18)	C9—H9	0.9500
C1—C10	1.4165 (19)	C10—H10	0.9500
C2—C3	1.4234 (18)	C11—H11A	0.9800
C2—H2	0.9500	C11—H11B	0.9800
C3—C4	1.4219 (18)	C11—H11C	0.9800
C3—C8	1.4284 (17)	C13—C14	1.500 (2)
C4—C5	1.3715 (19)	C13—H13A	0.9900
C4—H4	0.9500	C13—H13B	0.9900
C5—C6	1.4209 (19)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—C7	1.3776 (18)	C14—H14C	0.9800
C1—O1—C11	118.39 (11)	C10—C9—H9	119.6
C12—O3—C13	117.27 (11)	C8—C9—H9	119.6
O1—C1—C2	125.68 (12)	C9—C10—C1	120.50 (12)
O1—C1—C10	113.52 (11)	C9—C10—H10	119.8
C2—C1—C10	120.80 (12)	C1—C10—H10	119.8
C1—C2—C3	119.57 (11)	O1—C11—H11A	109.5
C1—C2—H2	120.2	O1—C11—H11B	109.5
C3—C2—H2	120.2	H11A—C11—H11B	109.5
C4—C3—C2	122.03 (11)	O1—C11—H11C	109.5
C4—C3—C8	118.18 (11)	H11A—C11—H11C	109.5
C2—C3—C8	119.78 (11)	H11B—C11—H11C	109.5
C5—C4—C3	121.10 (12)	O2—C12—O3	123.70 (13)
C5—C4—H4	119.4	O2—C12—C6	124.46 (13)
C3—C4—H4	119.4	O3—C12—C6	111.83 (12)
C4—C5—C6	120.52 (12)	O3—C13—C14	110.88 (12)
C4—C5—H5	119.7	O3—C13—H13A	109.5
C6—C5—H5	119.7	C14—C13—H13A	109.5
C7—C6—C5	119.50 (12)	O3—C13—H13B	109.5
C7—C6—C12	121.90 (12)	C14—C13—H13B	109.5
C5—C6—C12	118.59 (12)	H13A—C13—H13B	108.1
C6—C7—C8	121.12 (12)	C13—C14—H14A	109.5
C6—C7—H7	119.4	C13—C14—H14B	109.5
C8—C7—H7	119.4	H14A—C14—H14B	109.5
C7—C8—C9	121.94 (11)	C13—C14—H14C	109.5
C7—C8—C3	119.56 (11)	H14A—C14—H14C	109.5
C9—C8—C3	118.49 (11)	H14B—C14—H14C	109.5
C10—C9—C8	120.84 (12)
C11—O1—C1—C2	−8.42 (18)	C2—C3—C8—C7	−179.56 (10)
C11—O1—C1—C10	171.85 (11)	C4—C3—C8—C9	178.33 (11)
O1—C1—C2—C3	179.35 (11)	C2—C3—C8—C9	−0.81 (16)
C10—C1—C2—C3	−0.94 (17)	C7—C8—C9—C10	177.99 (11)
C1—C2—C3—C4	−177.47 (11)	C3—C8—C9—C10	−0.73 (17)
C1—C2—C3—C8	1.64 (16)	C8—C9—C10—C1	1.45 (18)
C2—C3—C4—C5	178.18 (11)	O1—C1—C10—C9	179.14 (11)
C8—C3—C4—C5	−0.94 (17)	C2—C1—C10—C9	−0.61 (18)
C3—C4—C5—C6	1.47 (18)	C13—O3—C12—O2	−0.89 (19)
C4—C5—C6—C7	−0.62 (18)	C13—O3—C12—C6	179.47 (11)
C4—C5—C6—C12	−179.26 (11)	C7—C6—C12—O2	−165.77 (13)
C5—C6—C7—C8	−0.76 (17)	C5—C6—C12—O2	12.84 (19)
C12—C6—C7—C8	177.83 (11)	C7—C6—C12—O3	13.87 (16)
C6—C7—C8—C9	−177.43 (11)	C5—C6—C12—O3	−167.53 (11)
C6—C7—C8—C3	1.27 (17)	C12—O3—C13—C14	−85.31 (15)
C4—C3—C8—C7	−0.42 (16)