Ethyl 2-(4-chloro-phenyl)-3-(3,5-di-fluoro-phenoxy)acrylate.

In the title compound, C(17)H(13)ClF(2)O(3), a multifunctional aromatic compound, the dihedral angle between the two benzene rings is 51.8 (3)°.

Related literature

For the biological activities of phenyl­acetate and styrene derivatives, see: Fang et al. (2007 ▶); Liu et al. (2008 ▶); Shi et al. (2007 ▶, 2008 ▶); Zhang, et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H13ClF2O3

M = 338.72

Monoclinic,

a = 9.4999 (17) Å

b = 7.6771 (14) Å

c = 21.564 (4) Å

β = 91.40 (3)°

V = 1572.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.939, T max = 0.947

3284 measured reflections

3090 independent reflections

2000 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.283

S = 1.08

3090 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036957/hg2439sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036957/hg2439Isup2.hkl

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

C17H13ClF2O3	F000 = 696
Mr = 338.72	Dx = 1.431 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1213 reflections
a = 9.4999 (17) Å	θ = 2.5–25.3º
b = 7.6771 (14) Å	µ = 0.28 mm−1
c = 21.564 (4) Å	T = 298 (2) K
β = 91.40 (3)º	Block, colorless
V = 1572.2 (5) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 298(2) K	θmax = 26.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = 0→11
Tmin = 0.939, Tmax = 0.947	k = 0→9
3284 measured reflections	l = −26→26

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)] = 0.071	H-atom parameters constrained
wR(F2) = 0.283	w = 1/[σ2(Fo2) + (0.171P)2 + 0.5784P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3090 reflections	Δρmax = 0.48 e Å−3
209 parameters	Δρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C14	1.0156 (4)	0.6558 (5)	0.20983 (16)	0.0391 (9)
C7	1.0360 (4)	0.6643 (5)	0.27791 (16)	0.0362 (8)
C15	1.1233 (4)	0.5884 (5)	0.16872 (17)	0.0428 (9)
C13	0.8915 (4)	0.7118 (5)	0.18452 (17)	0.0394 (9)
H13	0.8261	0.7565	0.2117	0.047*
C8	1.1571 (4)	0.7361 (5)	0.30569 (18)	0.0424 (9)
H8	1.2298	0.7728	0.2807	0.051*
C11	0.9438 (4)	0.6248 (6)	0.38096 (19)	0.0509 (10)
H11	0.8726	0.5864	0.4064	0.061*
C2	0.6293 (4)	0.8598 (6)	0.13280 (19)	0.0486 (10)
H2	0.6553	0.9036	0.1716	0.058*
C1	0.7207 (4)	0.7578 (5)	0.09956 (18)	0.0417 (9)
C6	0.6816 (5)	0.6998 (6)	0.04035 (19)	0.0510 (11)
H6	0.7431	0.6344	0.0168	0.061*
C10	1.0635 (4)	0.6998 (6)	0.40610 (18)	0.0486 (10)
C12	0.9308 (4)	0.6072 (5)	0.31709 (18)	0.0430 (9)
H12	0.8500	0.5562	0.3000	0.052*
C9	1.1716 (4)	0.7540 (5)	0.36912 (19)	0.0470 (10)
H9	1.2531	0.8020	0.3867	0.056*
C5	0.5495 (5)	0.7422 (6)	0.0178 (2)	0.0524 (11)
C4	0.4541 (5)	0.8378 (7)	0.0493 (2)	0.0585 (12)
H4	0.3650	0.8629	0.0329	0.070*
C3	0.4983 (4)	0.8946 (6)	0.1066 (2)	0.0542 (11)
O1	1.1121 (3)	0.5871 (5)	0.11246 (13)	0.0641 (9)
O2	1.2379 (3)	0.5253 (4)	0.19845 (12)	0.0461 (7)
O3	0.8532 (4)	0.7092 (5)	0.12313 (16)	0.0664 (9)
C16	1.3459 (4)	0.4580 (7)	0.1585 (2)	0.0563 (12)
H16A	1.3703	0.5452	0.1280	0.068*
H16B	1.3113	0.3555	0.1367	0.068*
F1	0.5110 (3)	0.6844 (5)	−0.03974 (14)	0.0852 (10)
C17	1.4696 (5)	0.4135 (9)	0.1967 (2)	0.0833 (18)
H17A	1.4993	0.5136	0.2202	0.125*
H17B	1.5443	0.3769	0.1704	0.125*
H17C	1.4466	0.3206	0.2244	0.125*
F2	0.4078 (3)	0.9913 (5)	0.14082 (16)	0.0970 (12)
Cl1	1.07938 (14)	0.7341 (2)	0.48566 (5)	0.0805 (6)

	U11	U22	U33	U12	U13	U23
C14	0.0362 (19)	0.043 (2)	0.0375 (19)	0.0008 (16)	−0.0035 (15)	0.0011 (16)
C7	0.0356 (18)	0.0357 (19)	0.0374 (19)	0.0084 (15)	−0.0012 (14)	0.0008 (15)
C15	0.040 (2)	0.048 (2)	0.040 (2)	0.0021 (17)	−0.0007 (16)	0.0006 (17)
C13	0.0382 (19)	0.041 (2)	0.0386 (19)	0.0015 (16)	−0.0023 (15)	−0.0047 (16)
C8	0.0340 (18)	0.050 (2)	0.043 (2)	−0.0018 (17)	−0.0016 (15)	−0.0006 (17)
C11	0.044 (2)	0.065 (3)	0.044 (2)	0.003 (2)	0.0058 (17)	0.005 (2)
C2	0.050 (2)	0.049 (2)	0.047 (2)	0.0039 (19)	−0.0064 (18)	−0.0056 (19)
C1	0.0375 (19)	0.045 (2)	0.042 (2)	0.0017 (17)	−0.0041 (16)	0.0047 (17)
C6	0.050 (2)	0.060 (3)	0.043 (2)	0.010 (2)	−0.0033 (18)	−0.0019 (19)
C10	0.045 (2)	0.065 (3)	0.0356 (19)	0.010 (2)	−0.0018 (16)	−0.0038 (19)
C12	0.0374 (19)	0.047 (2)	0.045 (2)	−0.0024 (17)	−0.0015 (16)	0.0012 (17)
C9	0.038 (2)	0.056 (3)	0.047 (2)	0.0011 (18)	−0.0059 (17)	−0.0103 (19)
C5	0.052 (2)	0.059 (3)	0.045 (2)	0.002 (2)	−0.0103 (19)	−0.001 (2)
C4	0.044 (2)	0.072 (3)	0.059 (3)	0.006 (2)	−0.013 (2)	0.006 (2)
C3	0.048 (2)	0.054 (3)	0.060 (3)	0.011 (2)	−0.0001 (19)	−0.003 (2)
O1	0.0592 (19)	0.095 (3)	0.0375 (16)	0.0233 (18)	0.0006 (13)	0.0027 (16)
O2	0.0393 (14)	0.0551 (17)	0.0442 (15)	0.0111 (13)	0.0049 (11)	−0.0029 (12)
O3	0.060 (2)	0.080 (2)	0.058 (2)	0.0072 (17)	−0.0116 (15)	−0.0001 (17)
C16	0.050 (2)	0.068 (3)	0.051 (2)	0.010 (2)	0.011 (2)	−0.007 (2)
F1	0.076 (2)	0.124 (3)	0.0538 (16)	0.0185 (19)	−0.0268 (14)	−0.0219 (17)
C17	0.058 (3)	0.126 (5)	0.066 (3)	0.038 (3)	0.004 (2)	−0.009 (3)
F2	0.070 (2)	0.134 (3)	0.087 (2)	0.053 (2)	−0.0065 (16)	−0.029 (2)
Cl1	0.0637 (8)	0.1398 (14)	0.0378 (6)	0.0078 (8)	−0.0051 (5)	−0.0114 (7)

C14—C13	1.357 (5)	C6—C5	1.374 (6)
C14—C15	1.465 (5)	C6—H6	0.9300
C14—C7	1.478 (5)	C10—C9	1.380 (6)
C7—C12	1.395 (5)	C10—Cl1	1.739 (4)
C7—C8	1.397 (5)	C12—H12	0.9300
C15—O1	1.215 (5)	C9—H9	0.9300
C15—O2	1.340 (5)	C5—F1	1.359 (5)
C13—O3	1.364 (5)	C5—C4	1.361 (7)
C13—H13	0.9300	C4—C3	1.368 (6)
C8—C9	1.378 (5)	C4—H4	0.9300
C8—H8	0.9300	C3—F2	1.365 (5)
C11—C10	1.374 (6)	O2—C16	1.450 (5)
C11—C12	1.386 (5)	C16—C17	1.459 (6)
C11—H11	0.9300	C16—H16A	0.9700
C2—C3	1.380 (6)	C16—H16B	0.9700
C2—C1	1.382 (6)	C17—H17A	0.9600
C2—H2	0.9300	C17—H17B	0.9600
C1—C6	1.394 (6)	C17—H17C	0.9600
C1—O3	1.397 (5)
C13—C14—C15	118.8 (3)	C11—C12—C7	121.5 (4)
C13—C14—C7	118.5 (3)	C11—C12—H12	119.2
C15—C14—C7	122.7 (3)	C7—C12—H12	119.2
C12—C7—C8	117.3 (3)	C8—C9—C10	119.0 (4)
C12—C7—C14	120.6 (3)	C8—C9—H9	120.5
C8—C7—C14	122.0 (3)	C10—C9—H9	120.5
O1—C15—O2	121.7 (3)	F1—C5—C4	117.6 (4)
O1—C15—C14	124.1 (3)	F1—C5—C6	118.0 (4)
O2—C15—C14	114.2 (3)	C4—C5—C6	124.4 (4)
C14—C13—O3	126.4 (4)	C5—C4—C3	115.5 (4)
C14—C13—H13	116.8	C5—C4—H4	122.3
O3—C13—H13	116.8	C3—C4—H4	122.3
C9—C8—C7	121.8 (4)	F2—C3—C4	118.5 (4)
C9—C8—H8	119.1	F2—C3—C2	117.3 (4)
C7—C8—H8	119.1	C4—C3—C2	124.2 (4)
C10—C11—C12	119.1 (4)	C15—O2—C16	115.0 (3)
C10—C11—H11	120.5	C13—O3—C1	124.4 (3)
C12—C11—H11	120.5	O2—C16—C17	108.7 (4)
C3—C2—C1	118.0 (4)	O2—C16—H16A	110.0
C3—C2—H2	121.0	C17—C16—H16A	110.0
C1—C2—H2	121.0	O2—C16—H16B	110.0
C2—C1—C6	119.9 (4)	C17—C16—H16B	110.0
C2—C1—O3	122.3 (4)	H16A—C16—H16B	108.3
C6—C1—O3	117.7 (4)	C16—C17—H17A	109.5
C5—C6—C1	118.0 (4)	C16—C17—H17B	109.5
C5—C6—H6	121.0	H17A—C17—H17B	109.5
C1—C6—H6	121.0	C16—C17—H17C	109.5
C11—C10—C9	121.3 (4)	H17A—C17—H17C	109.5
C11—C10—Cl1	120.3 (3)	H17B—C17—H17C	109.5
C9—C10—Cl1	118.4 (3)
C13—C14—C7—C12	45.7 (5)	C8—C7—C12—C11	1.6 (6)
C15—C14—C7—C12	−133.9 (4)	C14—C7—C12—C11	−175.6 (4)
C13—C14—C7—C8	−131.3 (4)	C7—C8—C9—C10	−0.1 (6)
C15—C14—C7—C8	49.1 (5)	C11—C10—C9—C8	1.6 (7)
C13—C14—C15—O1	3.9 (6)	Cl1—C10—C9—C8	−176.6 (3)
C7—C14—C15—O1	−176.5 (4)	C1—C6—C5—F1	−179.5 (4)
C13—C14—C15—O2	−175.6 (4)	C1—C6—C5—C4	0.3 (7)
C7—C14—C15—O2	3.9 (6)	F1—C5—C4—C3	−179.3 (4)
C15—C14—C13—O3	1.5 (6)	C6—C5—C4—C3	0.9 (7)
C7—C14—C13—O3	−178.1 (4)	C5—C4—C3—F2	−179.9 (4)
C12—C7—C8—C9	−1.4 (6)	C5—C4—C3—C2	−0.3 (7)
C14—C7—C8—C9	175.7 (4)	C1—C2—C3—F2	178.1 (4)
C3—C2—C1—C6	2.7 (6)	C1—C2—C3—C4	−1.5 (7)
C3—C2—C1—O3	−177.2 (4)	O1—C15—O2—C16	0.5 (6)
C2—C1—C6—C5	−2.2 (7)	C14—C15—O2—C16	−179.9 (4)
O3—C1—C6—C5	177.8 (4)	C14—C13—O3—C1	175.6 (4)
C12—C11—C10—C9	−1.4 (7)	C2—C1—O3—C13	19.2 (6)
C12—C11—C10—Cl1	176.7 (3)	C6—C1—O3—C13	−160.7 (4)
C10—C11—C12—C7	−0.2 (6)	C15—O2—C16—C17	173.4 (4)