Ethyl (naphthalen-2-yl­oxy)acetate

Madan Kumar, S.; Manju, N.; Kalluraya, B.; Byrappa, K.; Abdoh, M.M.M.

doi:10.1107/S2414314616015947

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161594

https://doi.org/10.1107/S2414314616015947

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Ethyl (naphthalen-2-yloxy)acetate

S. Madan Kumar,^a N. Manju,^b Balakrishna Kalluraya,^b K. Byrappa ^c and M. M. M. Abdoh ^d ^*

^aPURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India, ^bDepartment of Post-Graduate and Research In Chemistry, Mangalagangori, Mangalore University, India, ^cDepartment of Material Science, Mangalore University, Mangaluru 574 199, India, and ^dDepartment of Physics, Faculty of Science, An Najah National, University, Nablus, West Bank, Palestinian Territories
^*Correspondence e-mail: muneer@najah.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 October 2016; accepted 9 October 2016; online 18 October 2016)

In the title compound, C₁₄H₁₄O₃, the dihedral angle between the naphthyl ring system and the side chain is 9.00 (14)°, and the ethoxy chain adopts an extended conformation [C—O—C—C = 176.0 (3)°]. There are no directional interactions in the crystal beyond normal van der Waals contacts.

Keywords: napthyloxy; crystal structure; extended conformation.

CCDC reference: 1506733

Structure description

As part of our interest in intermediates used to prepare naproxen, a non-steroidal anti-inflammatory drug, the synthesis and crystal structure of the title compound is reported here. For related structures, see: Ravikumar et al. (1985 ) and Bond et al. (2013 ).

The dihedral angle between the naphthyl ring system and the side chain is 9.00 (14)° (Fig. 1) and the ethoxy chain adopts an extended conformation [C12—O3—C13—C14 = 176.0 (3)°]. There are no directional interactions in the crystal beyond normal van der Waals contacts. The crystal packing is shown in Fig. 2.

Figure 1
A view of the title molecule, with displacement ellipsoids drawn at the 50% probability level.

Figure 2
A view along the a axis of the crystal packing of the title compound.

Synthesis and crystallization

2-Naphthol (0.1 mol) was dissolved in 250 ml of dry acetone and mixed with anhydrous potassium carbonate (0.16 mol). Ethyl chloroacetate (0.1 mol) was added and the mixture refluxed for 5–6 h. The progress of the reaction was monitored by thin layer chromatography; upon completion, the reaction mixture was filtered and the solvent removed under reduced pressure. The product obtained was recrystallized from ethanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₄H₁₄O₃
M_r	230.25
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	6.0504 (11), 10.2188 (13), 10.8744 (16)
α, β, γ (°)	106.062 (12), 102.923 (14), 103.358 (14)
V (Å³)	598.15 (17)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.31 × 0.26 × 0.23

Data collection
Diffractometer	Rigaku Saturn724+ CCD
Absorption correction	Multi-scan (NUMABS; Rigaku, 1999 )
T_min, T_max	0.973, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	6262, 2265, 1133
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.259, 1.04
No. of reflections	2265
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.21
Computer programs: CrystalClear SM Expert (Rigaku, 2011 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1506733

Crystal structure: contains datablock I245. DOI: https://doi.org/10.1107/S2414314616015947/hb4083sup1.cif

checkCIF report

Computing details top

Data collection: CrystalClear SM Expert (Rigaku, 2011); cell refinement: CrystalClear SM Expert (Rigaku, 2011); data reduction: CrystalClear SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Ethyl (naphthalen-2-yloxy)acetate top

Crystal data top

C₁₄H₁₄O₃	Z = 2
M_r = 230.25	F(000) = 244
Triclinic, P1	D_x = 1.278 Mg m⁻³
a = 6.0504 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2188 (13) Å	Cell parameters from 2265 reflections
c = 10.8744 (16) Å	θ = 2.2–25.7°
α = 106.062 (12)°	µ = 0.09 mm⁻¹
β = 102.923 (14)°	T = 293 K
γ = 103.358 (14)°	Block, colourless
V = 598.15 (17) Å³	0.31 × 0.26 × 0.23 mm

Data collection top

Rigaku Saturn724+ CCD diffractometer	1133 reflections with I > 2σ(I)
profile data from ω–scans	R_int = 0.083
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	θ_max = 25.7°, θ_min = 2.2°
T_min = 0.973, T_max = 0.980	h = −7→7
6262 measured reflections	k = −10→12
2265 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.083	H-atom parameters constrained
wR(F²) = 0.259	w = 1/[σ²(F_o²) + (0.113P)² + 0.0443P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.003
2265 reflections	Δρ_max = 0.16 e Å⁻³
155 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2337 (4)	0.3569 (3)	0.9618 (2)	0.0765 (8)
O2	0.2739 (5)	0.4668 (3)	0.7673 (3)	0.0915 (10)
O3	0.5040 (5)	0.3364 (3)	0.7049 (2)	0.0783 (9)
C1	0.0300 (6)	0.3263 (4)	1.1143 (4)	0.0719 (11)
H1	−0.0336	0.3969	1.0988	0.086*
C2	−0.0308 (6)	0.2642 (4)	1.2017 (4)	0.0755 (11)
H2	−0.1382	0.2915	1.2446	0.091*
C3	0.0669 (6)	0.1581 (4)	1.2292 (4)	0.0692 (10)
C4	0.0083 (7)	0.0897 (4)	1.3181 (4)	0.0823 (12)
H4	−0.1001	0.1136	1.3618	0.099*
C5	0.1070 (8)	−0.0108 (5)	1.3414 (4)	0.0904 (13)
H5	0.0686	−0.0533	1.4025	0.108*
C6	0.2645 (8)	−0.0510 (4)	1.2754 (4)	0.0896 (13)
H6	0.3278	−0.1220	1.2903	0.108*
C7	0.3263 (7)	0.0129 (4)	1.1895 (4)	0.0789 (12)
H7	0.4360	−0.0125	1.1476	0.095*
C8	0.2261 (6)	0.1186 (4)	1.1622 (3)	0.0641 (10)
C9	0.2891 (6)	0.1861 (4)	1.0725 (4)	0.0679 (10)
H9	0.4001	0.1629	1.0307	0.082*
C10	0.1873 (6)	0.2851 (4)	1.0473 (3)	0.0626 (9)
C11	0.3813 (6)	0.3139 (4)	0.8862 (3)	0.0696 (10)
H11A	0.3247	0.2105	0.8429	0.084*
H11B	0.5432	0.3412	0.9450	0.084*
C12	0.3782 (6)	0.3843 (4)	0.7817 (3)	0.0672 (10)
C13	0.5213 (7)	0.3934 (4)	0.5988 (4)	0.0809 (12)
H13A	0.5844	0.4972	0.6355	0.097*
H13B	0.3649	0.3663	0.5341	0.097*
C14	0.6823 (7)	0.3339 (5)	0.5331 (4)	0.1014 (15)
H14A	0.6934	0.3679	0.4600	0.152*
H14B	0.6205	0.2311	0.4992	0.152*
H14C	0.8380	0.3640	0.5972	0.152*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0922 (19)	0.0789 (17)	0.0901 (18)	0.0563 (15)	0.0460 (15)	0.0383 (15)
O2	0.107 (2)	0.108 (2)	0.103 (2)	0.0777 (18)	0.0463 (16)	0.0527 (17)
O3	0.107 (2)	0.0873 (18)	0.0788 (17)	0.0646 (16)	0.0473 (15)	0.0437 (14)
C1	0.070 (2)	0.076 (3)	0.079 (3)	0.044 (2)	0.024 (2)	0.024 (2)
C2	0.079 (3)	0.084 (3)	0.084 (3)	0.051 (2)	0.043 (2)	0.026 (2)
C3	0.076 (2)	0.072 (2)	0.072 (2)	0.035 (2)	0.0347 (19)	0.0232 (19)
C4	0.085 (3)	0.095 (3)	0.086 (3)	0.046 (2)	0.046 (2)	0.030 (2)
C5	0.114 (3)	0.093 (3)	0.089 (3)	0.048 (3)	0.047 (3)	0.044 (2)
C6	0.123 (4)	0.080 (3)	0.094 (3)	0.058 (3)	0.045 (3)	0.042 (3)
C7	0.094 (3)	0.081 (3)	0.087 (3)	0.054 (2)	0.041 (2)	0.035 (2)
C8	0.070 (2)	0.061 (2)	0.069 (2)	0.0342 (19)	0.0258 (18)	0.0198 (18)
C9	0.071 (2)	0.070 (2)	0.078 (2)	0.0433 (19)	0.0319 (19)	0.023 (2)
C10	0.067 (2)	0.066 (2)	0.067 (2)	0.0345 (18)	0.0293 (18)	0.0231 (18)
C11	0.084 (2)	0.069 (2)	0.073 (2)	0.042 (2)	0.0305 (19)	0.0296 (19)
C12	0.069 (2)	0.070 (2)	0.074 (2)	0.039 (2)	0.0261 (18)	0.0254 (19)
C13	0.104 (3)	0.093 (3)	0.069 (2)	0.054 (2)	0.033 (2)	0.039 (2)
C14	0.121 (4)	0.131 (4)	0.092 (3)	0.072 (3)	0.054 (3)	0.055 (3)

Geometric parameters (Å, º) top

O1—C10	1.372 (4)	C6—H6	0.9300
O1—C11	1.406 (4)	C6—C7	1.349 (5)
O2—C12	1.187 (4)	C7—H7	0.9300
O3—C12	1.322 (4)	C7—C8	1.421 (5)
O3—C13	1.442 (4)	C8—C9	1.411 (5)
C1—H1	0.9300	C9—H9	0.9300
C1—C2	1.350 (5)	C9—C10	1.358 (5)
C1—C10	1.393 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C2—C3	1.418 (5)	C11—C12	1.502 (5)
C3—C4	1.402 (5)	C13—H13A	0.9700
C3—C8	1.397 (5)	C13—H13B	0.9700
C4—H4	0.9300	C13—C14	1.474 (5)
C4—C5	1.355 (5)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C5—C6	1.384 (5)	C14—H14C	0.9600

C10—O1—C11	116.5 (2)	C10—C9—C8	119.9 (3)
C12—O3—C13	117.0 (3)	C10—C9—H9	120.1
C2—C1—H1	119.8	O1—C10—C1	114.3 (3)
C2—C1—C10	120.4 (3)	C9—C10—O1	125.0 (3)
C10—C1—H1	119.8	C9—C10—C1	120.7 (3)
C1—C2—H2	119.5	O1—C11—H11A	109.8
C1—C2—C3	121.0 (3)	O1—C11—H11B	109.8
C3—C2—H2	119.5	O1—C11—C12	109.3 (3)
C4—C3—C2	123.2 (3)	H11A—C11—H11B	108.3
C8—C3—C2	118.1 (3)	C12—C11—H11A	109.8
C8—C3—C4	118.7 (3)	C12—C11—H11B	109.8
C3—C4—H4	119.5	O2—C12—O3	125.0 (4)
C5—C4—C3	121.0 (4)	O2—C12—C11	125.7 (3)
C5—C4—H4	119.5	O3—C12—C11	109.3 (3)
C4—C5—H5	119.6	O3—C13—H13A	110.2
C4—C5—C6	120.7 (4)	O3—C13—H13B	110.2
C6—C5—H5	119.6	O3—C13—C14	107.7 (3)
C5—C6—H6	120.0	H13A—C13—H13B	108.5
C7—C6—C5	120.0 (4)	C14—C13—H13A	110.2
C7—C6—H6	120.0	C14—C13—H13B	110.2
C6—C7—H7	119.6	C13—C14—H14A	109.5
C6—C7—C8	120.9 (4)	C13—C14—H14B	109.5
C8—C7—H7	119.6	C13—C14—H14C	109.5
C3—C8—C7	118.6 (3)	H14A—C14—H14B	109.5
C3—C8—C9	119.9 (3)	H14A—C14—H14C	109.5
C9—C8—C7	121.5 (3)	H14B—C14—H14C	109.5
C8—C9—H9	120.1

O1—C11—C12—O2	2.2 (5)	C5—C6—C7—C8	−1.9 (6)
O1—C11—C12—O3	−175.8 (3)	C6—C7—C8—C3	1.8 (6)
C1—C2—C3—C4	−179.5 (4)	C6—C7—C8—C9	−180.0 (4)
C1—C2—C3—C8	−0.6 (6)	C7—C8—C9—C10	179.1 (3)
C2—C1—C10—O1	−179.9 (3)	C8—C3—C4—C5	1.4 (6)
C2—C1—C10—C9	−2.5 (6)	C8—C9—C10—O1	−179.6 (3)
C2—C3—C4—C5	−179.8 (4)	C8—C9—C10—C1	3.3 (6)
C2—C3—C8—C7	179.6 (3)	C10—O1—C11—C12	170.1 (3)
C2—C3—C8—C9	1.4 (6)	C10—C1—C2—C3	1.2 (6)
C3—C4—C5—C6	−1.5 (7)	C11—O1—C10—C1	−176.7 (3)
C3—C8—C9—C10	−2.7 (6)	C11—O1—C10—C9	6.1 (5)
C4—C3—C8—C7	−1.5 (6)	C12—O3—C13—C14	176.0 (3)
C4—C3—C8—C9	−179.7 (3)	C13—O3—C12—O2	2.2 (6)
C4—C5—C6—C7	1.8 (7)	C13—O3—C12—C11	−179.7 (3)

Acknowledgements

The authors thank DST–PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility.

References

Bond, A. D., Cornell, C., Larsen, F. H., Qu, H., Raijada, D. & Rantanen, J. (2013). CrystEngComm, 13, 3665–3671. CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ravikumar, K., Rajan, S. S., Pattabhi, V. & Gabe, E. J. (1985). Acta Cryst. C41, 280–282. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2011). CrystalClear SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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