2-Phen-oxy-ethyl benzoate.

In the title compound, C15H14O3, the dihedral angle between the benzene rings is 75.85 (7)°. In the crystal, centrosymmetrically related mol-ecules are weakly associated through pairs of inter-actions between a benzene ring and an O atom of the ester group [ring centroid⋯O = 3.952 (7) Å], and through pairs of inter-actions between the other benzene ring and an O atom of the phen-oxy 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 = 242.26

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.02

2269 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010878/zs2256sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010878/zs2256Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010878/zs2256Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14O3	F(000) = 512
Mr = 242.26	Dx = 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

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	Rint = 0.029
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −11→10
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	k = −9→12
Tmin = 0.995, Tmax = 0.997	l = −12→16
5089 measured reflections

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(Fo2) + (0.0531P)2 + 0.042P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2269 reflections	Δρmax = 0.11 e Å−3
164 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)