1-[2-(3,5-Difluoro-benz-yloxy)phen-yl]ethanone.

In the title compound, C(15)H(12)F(2)O(2), the dihedral angle between the aromatic rings is 70.43 (4)°. The crystal packing exhibits no significantly short inter-molecular contacts.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 ▶). For a related structure, see: Ma et al. (2010 ▶).

Experimental

Crystal data

C15H12F2O2

M = 262.25

Triclinic,

a = 7.2808 (7) Å

b = 7.9734 (8) Å

c = 11.6466 (12) Å

α = 91.587 (1)°

β = 106.559 (2)°

γ = 95.343 (1)°

V = 644.22 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.42 × 0.38 × 0.20 mm

Data collection

Bruker SMART CD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.979

3373 measured reflections

2239 independent reflections

1402 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.153

S = 1.03

2239 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003120X/zs2054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003120X/zs2054Isup2.hkl

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

C15H12F2O2	Z = 2
Mr = 262.25	F(000) = 272
Triclinic, P1	Dx = 1.352 Mg m−3
Hall symbol: -P 1	Melting point = 347–348 K
a = 7.2808 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9734 (8) Å	Cell parameters from 1136 reflections
c = 11.6466 (12) Å	θ = 2.9–24.8°
α = 91.587 (1)°	µ = 0.11 mm−1
β = 106.559 (2)°	T = 298 K
γ = 95.343 (1)°	Plate, colorless
V = 644.22 (11) Å3	0.42 × 0.38 × 0.20 mm

Bruker SMART CD area-detector diffractometer	2239 independent reflections
Radiation source: fine-focus sealed tube	1402 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.956, Tmax = 0.979	k = −9→5
3373 measured reflections	l = −13→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.1465P] where P = (Fo2 + 2Fc2)/3
2239 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
F1	0.1438 (3)	0.8789 (4)	0.0404 (2)	0.1646 (11)
F2	0.6758 (4)	0.6785 (4)	−0.0348 (2)	0.1880 (13)
O1	0.7550 (3)	0.2045 (2)	0.54230 (18)	0.0964 (7)
O2	0.7176 (2)	0.67975 (18)	0.41603 (13)	0.0629 (5)
C1	0.6631 (4)	0.3400 (3)	0.3629 (2)	0.0627 (7)
H1A	0.6321	0.2260	0.3292	0.094*
H1B	0.7598	0.3965	0.3321	0.094*
H1C	0.5495	0.3981	0.3416	0.094*
C2	0.7371 (3)	0.3388 (3)	0.4951 (2)	0.0564 (6)
C3	0.7914 (3)	0.4967 (3)	0.57422 (19)	0.0471 (5)
C4	0.7837 (3)	0.6620 (3)	0.53600 (19)	0.0481 (5)
C5	0.8396 (3)	0.7987 (3)	0.6196 (2)	0.0583 (6)
H5	0.8355	0.9080	0.5938	0.070*
C6	0.9010 (4)	0.7728 (3)	0.7398 (2)	0.0659 (7)
H6	0.9379	0.8650	0.7950	0.079*
C7	0.9086 (4)	0.6135 (3)	0.7795 (2)	0.0674 (7)
H7	0.9501	0.5966	0.8612	0.081*
C8	0.8540 (3)	0.4786 (3)	0.6971 (2)	0.0590 (6)
H8	0.8592	0.3703	0.7247	0.071*
C9	0.7050 (4)	0.8454 (3)	0.3733 (2)	0.0700 (7)
H9A	0.8327	0.9048	0.3882	0.084*
H9B	0.6320	0.9090	0.4138	0.084*
C10	0.6061 (4)	0.8257 (3)	0.2421 (2)	0.0587 (6)
C11	0.4210 (4)	0.8648 (3)	0.1996 (2)	0.0682 (7)
H11	0.3585	0.9069	0.2518	0.082*
C12	0.3289 (4)	0.8415 (4)	0.0801 (3)	0.0856 (9)
C13	0.4081 (5)	0.7794 (4)	−0.0002 (3)	0.0902 (9)
H13	0.3405	0.7632	−0.0811	0.108*
C14	0.5903 (6)	0.7418 (5)	0.0421 (3)	0.0977 (10)
C15	0.6927 (5)	0.7637 (4)	0.1624 (3)	0.0914 (9)
H15	0.8189	0.7365	0.1887	0.110*

	U11	U22	U33	U12	U13	U23
F1	0.0955 (15)	0.243 (3)	0.1260 (18)	0.0644 (17)	−0.0240 (13)	−0.0392 (17)
F2	0.187 (3)	0.284 (4)	0.1253 (19)	0.063 (2)	0.0883 (18)	−0.035 (2)
O1	0.163 (2)	0.0435 (11)	0.0898 (14)	0.0206 (11)	0.0447 (13)	0.0108 (10)
O2	0.0905 (12)	0.0383 (9)	0.0520 (10)	0.0087 (8)	0.0073 (8)	0.0027 (7)
C1	0.0713 (16)	0.0452 (13)	0.0708 (16)	0.0032 (11)	0.0215 (13)	−0.0080 (11)
C2	0.0622 (15)	0.0418 (13)	0.0717 (16)	0.0098 (10)	0.0285 (12)	0.0048 (11)
C3	0.0466 (12)	0.0453 (12)	0.0519 (13)	0.0099 (9)	0.0164 (10)	0.0051 (10)
C4	0.0481 (12)	0.0447 (12)	0.0507 (13)	0.0090 (9)	0.0117 (10)	0.0024 (10)
C5	0.0618 (15)	0.0463 (13)	0.0625 (15)	0.0097 (11)	0.0103 (12)	−0.0028 (11)
C6	0.0668 (16)	0.0672 (17)	0.0589 (16)	0.0124 (12)	0.0101 (12)	−0.0132 (12)
C7	0.0713 (17)	0.0807 (19)	0.0501 (14)	0.0160 (14)	0.0148 (12)	0.0049 (13)
C8	0.0598 (14)	0.0578 (15)	0.0646 (16)	0.0149 (11)	0.0227 (12)	0.0135 (12)
C9	0.0921 (19)	0.0431 (13)	0.0622 (15)	0.0051 (12)	0.0025 (13)	0.0081 (11)
C10	0.0715 (16)	0.0443 (13)	0.0597 (15)	0.0077 (11)	0.0166 (12)	0.0110 (11)
C11	0.0706 (18)	0.0718 (17)	0.0618 (16)	0.0081 (13)	0.0189 (13)	−0.0016 (12)
C12	0.0740 (19)	0.099 (2)	0.075 (2)	0.0192 (16)	0.0052 (16)	−0.0020 (16)
C13	0.102 (2)	0.106 (2)	0.0591 (18)	0.0128 (19)	0.0171 (17)	0.0042 (16)
C14	0.117 (3)	0.117 (3)	0.076 (2)	0.022 (2)	0.052 (2)	−0.0050 (18)
C15	0.082 (2)	0.105 (2)	0.091 (2)	0.0324 (17)	0.0235 (17)	0.0040 (18)

F1—C12	1.359 (3)	C6—H6	0.9300
F2—C14	1.340 (4)	C7—C8	1.372 (3)
O1—C2	1.218 (3)	C7—H7	0.9300
O2—C4	1.358 (2)	C8—H8	0.9300
O2—C9	1.426 (3)	C9—C10	1.489 (3)
C1—C2	1.480 (3)	C9—H9A	0.9700
C1—H1A	0.9600	C9—H9B	0.9700
C1—H1B	0.9600	C10—C11	1.365 (3)
C1—H1C	0.9600	C10—C15	1.368 (4)
C2—C3	1.491 (3)	C11—C12	1.361 (4)
C3—C8	1.389 (3)	C11—H11	0.9300
C3—C4	1.404 (3)	C12—C13	1.336 (4)
C4—C5	1.390 (3)	C13—C14	1.342 (5)
C5—C6	1.371 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.384 (4)
C6—C7	1.365 (3)	C15—H15	0.9300
C4—O2—C9	118.86 (17)	C7—C8—H8	118.6
C2—C1—H1A	109.5	C3—C8—H8	118.6
C2—C1—H1B	109.5	O2—C9—C10	106.94 (18)
H1A—C1—H1B	109.5	O2—C9—H9A	110.3
C2—C1—H1C	109.5	C10—C9—H9A	110.3
H1A—C1—H1C	109.5	O2—C9—H9B	110.3
H1B—C1—H1C	109.5	C10—C9—H9B	110.3
O1—C2—C1	119.4 (2)	H9A—C9—H9B	108.6
O1—C2—C3	118.1 (2)	C11—C10—C15	118.4 (2)
C1—C2—C3	122.6 (2)	C11—C10—C9	119.5 (2)
C8—C3—C4	116.9 (2)	C15—C10—C9	122.0 (3)
C8—C3—C2	117.04 (19)	C12—C11—C10	119.4 (3)
C4—C3—C2	126.04 (19)	C12—C11—H11	120.3
O2—C4—C5	122.9 (2)	C10—C11—H11	120.3
O2—C4—C3	116.96 (18)	C13—C12—F1	118.0 (3)
C5—C4—C3	120.2 (2)	C13—C12—C11	123.8 (3)
C6—C5—C4	120.2 (2)	F1—C12—C11	118.2 (3)
C6—C5—H5	119.9	C12—C13—C14	116.5 (3)
C4—C5—H5	119.9	C12—C13—H13	121.7
C7—C6—C5	120.9 (2)	C14—C13—H13	121.7
C7—C6—H6	119.6	F2—C14—C13	118.8 (3)
C5—C6—H6	119.6	F2—C14—C15	118.6 (4)
C6—C7—C8	118.9 (2)	C13—C14—C15	122.6 (3)
C6—C7—H7	120.5	C10—C15—C14	119.2 (3)
C8—C7—H7	120.5	C10—C15—H15	120.4
C7—C8—C3	122.9 (2)	C14—C15—H15	120.4
O1—C2—C3—C8	−1.7 (3)	C2—C3—C8—C7	179.8 (2)
C1—C2—C3—C8	178.3 (2)	C4—O2—C9—C10	−173.0 (2)
O1—C2—C3—C4	178.8 (2)	O2—C9—C10—C11	107.6 (3)
C1—C2—C3—C4	−1.2 (3)	O2—C9—C10—C15	−70.1 (3)
C9—O2—C4—C5	0.1 (3)	C15—C10—C11—C12	−0.2 (4)
C9—O2—C4—C3	179.2 (2)	C9—C10—C11—C12	−177.9 (2)
C8—C3—C4—O2	−178.31 (19)	C10—C11—C12—C13	1.0 (5)
C2—C3—C4—O2	1.2 (3)	C10—C11—C12—F1	179.0 (3)
C8—C3—C4—C5	0.8 (3)	F1—C12—C13—C14	−179.2 (3)
C2—C3—C4—C5	−179.7 (2)	C11—C12—C13—C14	−1.1 (5)
O2—C4—C5—C6	178.5 (2)	C12—C13—C14—F2	179.7 (3)
C3—C4—C5—C6	−0.6 (3)	C12—C13—C14—C15	0.6 (5)
C4—C5—C6—C7	0.1 (4)	C11—C10—C15—C14	−0.3 (4)
C5—C6—C7—C8	0.1 (4)	C9—C10—C15—C14	177.3 (3)
C6—C7—C8—C3	0.2 (4)	F2—C14—C15—C10	−179.0 (3)
C4—C3—C8—C7	−0.6 (3)	C13—C14—C15—C10	0.1 (5)