2-Phen­oxy­ethyl benzoate

Al-Noaimi, M.; Warad, I.; Haddad, S.F.; Husein, A.; Shareiah, R.

doi:10.1107/S1600536813010878

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o789

https://doi.org/10.1107/S1600536813010878

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2-Phenoxyethyl benzoate

Mousa Al-Noaimi,^a ^* Ismail Warad,^b Salim F. Haddad,^c Ahmad Husein ^b and Rami Shareiah ^d

^aDepartment of Chemistry, Hashemite University, Zarqa 13115, Jordan, ^bDepartment of Chemistry, AN-Najah National University, Nablus, Palestinian Territories, ^cDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan, and ^dDepartment of Basic Science, Allied Medical Science College, Applied Science Private University, PO Box 166, Amman 11931, Jordan
^*Correspondence e-mail: manoaimi@hu.edu.jo

(Received 9 April 2013; accepted 22 April 2013; online 27 April 2013)

In the title compound, C₁₅H₁₄O₃, the dihedral angle between the benzene rings is 75.85 (7)°. In the crystal, centrosymmetrically related molecules are weakly associated through pairs of interactions between a benzene ring and an O atom of the ester group [ring centroid⋯O = 3.952 (7) Å], and through pairs of interactions between the other benzene ring and an O atom of the phenoxy group [ring centroid⋯O = 3.912 (7) Å], giving chains extending along [110].

Related literature

For background information and related structures, see: Gandhi et al. (1995 ); Huang et al. (1996 ); Litera et al. (2006 ); Ruzicka et al. (2002 ); Sheehan & Umezaw (1973 ).

Experimental

Crystal data

C₁₅H₁₄O₃
M_r = 242.26
Monoclinic, P 2₁ /c
a = 9.4675 (10) Å
b = 10.1411 (10) Å
c = 13.7792 (12) Å
β = 103.895 (10)°
V = 1284.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.32 × 0.26 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos CCD-detector diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ) T_min = 0.995, T_max = 0.997
5089 measured reflections
2269 independent reflections
1479 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.02
2269 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813010878/zs2256sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010878/zs2256Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010878/zs2256Isup3.cml

checkCIF report

Comment top

Phenoxyethyl benzoate has applications in the synthesis of e.g. oxazoles, imidazoles and benzoxazepines (Huang et al., 1996; Gandhi et al., 1995). Esters are also useful as photo-removable protecting groups for carboxylic acids in organic synthesis and biochemistry (Ruzicka et al., 2002; Litera et al., 2006; Sheehan & Umezaw, 1973). Keeping this in view, the title compound, C₁₅H₁₄O₃, was synthesized and its crystal structure is repored herein.

In the title compound (Fig. 1), the dihedral angle between the benzene rings is 75.85 (7)°. In the crystal, two centrosymmetrically related molecules are weakly associated through a pair of intermolecular interactions between a benzene ring [C1–C6] and an oxygen of the phenoxy group (O1A) [ring centroid(Cg)···O1A separation, 3.912 (7) Å] [for symmetry code (A): -x, -y + 1, -z]. In addition, the molecules are weakly associated through a similar pair of intermolecular interactions between the second benzene ring [C10–C15] and a carboxyl oxygen of the ester group (O2B) [ring centroid (Cg)···O2B separation, 3.952 (7) Å] [for symmetry code (B): -x + 1, -y, -z] (Fig. 2). The result is a chain structure extending across [110].

Related literature top

For background information and related structures, see: Gandhi et al. (1995); Huang et al. (1996); Litera et al. (2006); Ruzicka et al. (2002); Sheehan & Umezaw (1973).

Experimental top

Benzoic acid (10.0 g, 0.08 mol) was mixed directly without solvent with 2-phenoxyethanol (11.0 g, 0.08 mol) and refluxed for 3 hours. The reaction was left at room temperature for 24 hours. The product was collected as crystals in 52% yield. The crystals were purified by washing several times with cold ethanol.

Structure description top

For background information and related structures, see: Gandhi et al. (1995); Huang et al. (1996); Litera et al. (2006); Ruzicka et al. (2002); Sheehan & Umezaw (1973).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular conformation and atom numbering scheme for the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The chain structure showing the ring centroid···O associations [for symmetry code (A): -x, -y + 1, -z]; (B): -x + 1, -y, -z].

2-Phenoxyethyl benzoate top

Crystal data top

C₁₅H₁₄O₃	F(000) = 512
M_r = 242.26	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1664 reflections
a = 9.4675 (10) Å	θ = 3.0–29.3°
b = 10.1411 (10) Å	µ = 0.09 mm⁻¹
c = 13.7792 (12) Å	T = 293 K
β = 103.895 (10)°	Wedge, colourless
V = 1284.2 (2) Å³	0.32 × 0.26 × 0.18 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos CCD-detector diffractometer	2269 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1479 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 16.0534 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −11→10
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	k = −9→12
T_min = 0.995, T_max = 0.997	l = −12→16
5089 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0531P)² + 0.042P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2269 reflections	Δρ_max = 0.11 e Å⁻³
164 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (3)

Crystal data top

C₁₅H₁₄O₃	V = 1284.2 (2) Å³
M_r = 242.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4675 (10) Å	µ = 0.09 mm⁻¹
b = 10.1411 (10) Å	T = 293 K
c = 13.7792 (12) Å	0.32 × 0.26 × 0.18 mm
β = 103.895 (10)°

Data collection top

Oxford Diffraction Xcalibur Eos CCD-detector diffractometer	2269 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	1479 reflections with I > 2σ(I)
T_min = 0.995, T_max = 0.997	R_int = 0.029
5089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.02	Δρ_max = 0.11 e Å⁻³
2269 reflections	Δρ_min = −0.11 e Å⁻³
164 parameters

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.

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 > 2sigma(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

	x	y	z	U_iso*/U_eq
O2	0.21934 (14)	0.06786 (14)	0.04977 (8)	0.0697 (5)
O1	0.10626 (13)	0.31548 (14)	−0.04881 (9)	0.0693 (4)
C1	0.0173 (2)	0.39845 (19)	−0.11534 (12)	0.0573 (5)
C10	0.37587 (19)	−0.11334 (19)	0.06159 (13)	0.0589 (5)
C9	0.3215 (2)	−0.0031 (2)	0.11219 (14)	0.0644 (5)
C7	0.0433 (2)	0.2408 (2)	0.01671 (14)	0.0703 (6)
H7A	−0.0199	0.1734	−0.0206	0.084*
H7B	−0.0148	0.2977	0.0484	0.084*
C8	0.1615 (2)	0.1781 (2)	0.09424 (14)	0.0786 (6)
H8A	0.2379	0.2417	0.1196	0.094*
H8B	0.1232	0.1479	0.1497	0.094*
O3	0.36163 (17)	0.02131 (18)	0.19998 (10)	0.0968 (6)
C2	−0.1322 (2)	0.4027 (2)	−0.13240 (14)	0.0683 (6)
H2A	−0.1804	0.3477	−0.0970	0.082*
C5	0.0077 (3)	0.5679 (2)	−0.23750 (14)	0.0793 (7)
H5A	0.0554	0.6235	−0.2728	0.095*
C6	0.0870 (2)	0.4820 (2)	−0.16825 (14)	0.0709 (6)
H6A	0.1879	0.4800	−0.1569	0.085*
C11	0.4723 (2)	−0.2012 (2)	0.11906 (17)	0.0810 (7)
H11A	0.5006	−0.1905	0.1881	0.097*
C15	0.3333 (2)	−0.1315 (2)	−0.04026 (15)	0.0737 (6)
H15A	0.2669	−0.0739	−0.0794	0.088*
C3	−0.2097 (2)	0.4898 (2)	−0.20273 (16)	0.0809 (7)
H3A	−0.3107	0.4923	−0.2147	0.097*
C4	−0.1402 (3)	0.5723 (2)	−0.25494 (15)	0.0808 (7)
H4A	−0.1934	0.6307	−0.3018	0.097*
C13	0.4865 (3)	−0.3199 (3)	−0.0267 (2)	0.1029 (8)
H13A	0.5257	−0.3886	−0.0564	0.123*
C14	0.3890 (3)	−0.2350 (2)	−0.08458 (18)	0.0943 (7)
H14A	0.3603	−0.2471	−0.1534	0.113*
C12	0.5261 (3)	−0.3035 (3)	0.0747 (2)	0.1039 (9)
H12A	0.5904	−0.3628	0.1138	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0937 (10)	0.0559 (9)	0.0580 (7)	0.0144 (8)	0.0151 (7)	0.0017 (7)
O1	0.0707 (8)	0.0666 (9)	0.0747 (8)	0.0111 (7)	0.0255 (7)	0.0141 (7)
C1	0.0673 (12)	0.0505 (12)	0.0551 (10)	0.0079 (10)	0.0163 (9)	−0.0068 (9)
C10	0.0561 (11)	0.0540 (12)	0.0664 (12)	−0.0040 (10)	0.0146 (9)	0.0108 (10)
C9	0.0665 (12)	0.0659 (14)	0.0601 (11)	−0.0028 (11)	0.0139 (9)	0.0091 (11)
C7	0.0862 (14)	0.0593 (14)	0.0730 (12)	0.0087 (12)	0.0342 (10)	0.0017 (11)
C8	0.1139 (17)	0.0638 (14)	0.0627 (11)	0.0174 (13)	0.0303 (12)	0.0018 (11)
O3	0.1082 (12)	0.1176 (15)	0.0581 (8)	0.0162 (10)	0.0073 (8)	−0.0040 (9)
C2	0.0685 (13)	0.0602 (14)	0.0758 (12)	0.0002 (11)	0.0164 (10)	−0.0068 (11)
C5	0.1058 (18)	0.0711 (16)	0.0663 (12)	0.0138 (14)	0.0312 (12)	0.0101 (12)
C6	0.0747 (13)	0.0719 (15)	0.0716 (12)	0.0103 (12)	0.0284 (10)	0.0065 (12)
C11	0.0631 (13)	0.0809 (17)	0.0913 (15)	0.0054 (12)	0.0036 (11)	0.0145 (14)
C15	0.0933 (15)	0.0593 (14)	0.0717 (13)	0.0159 (12)	0.0262 (11)	0.0103 (11)
C3	0.0709 (13)	0.0768 (17)	0.0855 (14)	0.0073 (13)	0.0003 (12)	−0.0152 (14)
C4	0.1031 (18)	0.0686 (16)	0.0614 (12)	0.0196 (14)	0.0018 (12)	−0.0062 (11)
C13	0.107 (2)	0.0694 (17)	0.148 (2)	0.0217 (16)	0.0600 (19)	0.0079 (19)
C14	0.126 (2)	0.0727 (17)	0.0922 (15)	0.0136 (16)	0.0415 (14)	0.0034 (14)
C12	0.0790 (16)	0.089 (2)	0.139 (2)	0.0257 (15)	0.0167 (16)	0.0231 (19)

Geometric parameters (Å, º) top

O2—C9	1.339 (2)	C5—C4	1.364 (3)
O2—C8	1.445 (2)	C5—C6	1.374 (3)
O1—C1	1.373 (2)	C5—H5A	0.9300
O1—C7	1.415 (2)	C6—H6A	0.9300
C1—C2	1.379 (2)	C11—C12	1.364 (3)
C1—C6	1.384 (3)	C11—H11A	0.9300
C10—C15	1.376 (2)	C15—C14	1.381 (3)
C10—C11	1.381 (3)	C15—H15A	0.9300
C10—C9	1.474 (3)	C3—C4	1.370 (3)
C9—O3	1.203 (2)	C3—H3A	0.9300
C7—C8	1.491 (3)	C4—H4A	0.9300
C7—H7A	0.9700	C13—C12	1.367 (3)
C7—H7B	0.9700	C13—C14	1.369 (3)
C8—H8A	0.9700	C13—H13A	0.9300
C8—H8B	0.9700	C14—H14A	0.9300
C2—C3	1.384 (3)	C12—H12A	0.9300
C2—H2A	0.9300

C9—O2—C8	115.63 (14)	C4—C5—H5A	119.7
C1—O1—C7	117.97 (14)	C6—C5—H5A	119.7
O1—C1—C2	124.94 (18)	C5—C6—C1	120.2 (2)
O1—C1—C6	115.68 (17)	C5—C6—H6A	119.9
C2—C1—C6	119.39 (18)	C1—C6—H6A	119.9
C15—C10—C11	119.3 (2)	C12—C11—C10	120.0 (2)
C15—C10—C9	122.27 (17)	C12—C11—H11A	120.0
C11—C10—C9	118.41 (18)	C10—C11—H11A	120.0
O3—C9—O2	122.7 (2)	C10—C15—C14	120.2 (2)
O3—C9—C10	124.74 (18)	C10—C15—H15A	119.9
O2—C9—C10	112.59 (16)	C14—C15—H15A	119.9
O1—C7—C8	109.06 (16)	C4—C3—C2	121.1 (2)
O1—C7—H7A	109.9	C4—C3—H3A	119.5
C8—C7—H7A	109.9	C2—C3—H3A	119.5
O1—C7—H7B	109.9	C5—C4—C3	119.3 (2)
C8—C7—H7B	109.9	C5—C4—H4A	120.3
H7A—C7—H7B	108.3	C3—C4—H4A	120.3
O2—C8—C7	108.78 (15)	C12—C13—C14	120.0 (3)
O2—C8—H8A	109.9	C12—C13—H13A	120.0
C7—C8—H8A	109.9	C14—C13—H13A	120.0
O2—C8—H8B	109.9	C13—C14—C15	119.7 (2)
C7—C8—H8B	109.9	C13—C14—H14A	120.1
H8A—C8—H8B	108.3	C15—C14—H14A	120.1
C1—C2—C3	119.3 (2)	C11—C12—C13	120.7 (2)
C1—C2—H2A	120.3	C11—C12—H12A	119.7
C3—C2—H2A	120.3	C13—C12—H12A	119.7
C4—C5—C6	120.7 (2)

C7—O1—C1—C2	−8.7 (3)	O1—C1—C6—C5	179.26 (17)
C7—O1—C1—C6	171.67 (16)	C2—C1—C6—C5	−0.3 (3)
C8—O2—C9—O3	1.1 (3)	C15—C10—C11—C12	1.0 (3)
C8—O2—C9—C10	−179.74 (16)	C9—C10—C11—C12	−179.3 (2)
C15—C10—C9—O3	−175.5 (2)	C11—C10—C15—C14	−1.3 (3)
C11—C10—C9—O3	4.7 (3)	C9—C10—C15—C14	178.9 (2)
C15—C10—C9—O2	5.3 (3)	C1—C2—C3—C4	−0.5 (3)
C11—C10—C9—O2	−174.41 (17)	C6—C5—C4—C3	−0.2 (3)
C1—O1—C7—C8	−169.37 (15)	C2—C3—C4—C5	0.3 (3)
C9—O2—C8—C7	−176.41 (17)	C12—C13—C14—C15	1.3 (4)
O1—C7—C8—O2	−75.6 (2)	C10—C15—C14—C13	0.2 (4)
O1—C1—C2—C3	−179.05 (17)	C10—C11—C12—C13	0.5 (4)
C6—C1—C2—C3	0.5 (3)	C14—C13—C12—C11	−1.7 (4)
C4—C5—C6—C1	0.2 (3)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₃
M_r	242.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.4675 (10), 10.1411 (10), 13.7792 (12)
β (°)	103.895 (10)
V (Å³)	1284.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.26 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos CCD-detector
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.995, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	5089, 2269, 1479
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.02
No. of reflections	2269
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.11

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Acknowledgements

The project was supported by AN-Najah National University and the Hashemite University (Jordan). The X-ray structural work was performed at Hamdi Mango Center for Scientific Research at The University of Jordan, Amman 11942, Jordan.

References

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