Ethyl 2-(4-chloro­phenyl)-3-(3,5-di­fluoro­phenoxy)acrylate

Gong, H.-B.; Wang, J.; Liu, Y.; Wang, L.

doi:10.1107/S1600536808036957

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2372

doi:10.1107/S1600536808036957

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Ethyl 2-(4-chlorophenyl)-3-(3,5-difluorophenoxy)acrylate

Hai-Bin Gong,^a ^* Jie Wang,^a Ying Liu ^a and Lei Wang ^a

^aXuzhou Central Hospital, Xuzhou Cardiovascular Disease Institute, Xuzhou 221009, People's Republic of China
^*Correspondence e-mail: adler_20008@yahoo.com.cn

(Received 31 October 2008; accepted 10 November 2008; online 20 November 2008)

In the title compound, C₁₇H₁₃ClF₂O₃, 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_r = 338.72
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.071
wR(F²) = 0.283
S = 1.08
3090 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Recently, a few phenylacetate and styrene derivatives have been reported with versatile biological activities (Fang et al., 2007; Liu et al., 2008; Shi et al., 2007, 2008; Zhang, et al., 2008). We report herein the title new compound, (I), (Fig. 1).

In compound (I), the dihedral angle between the C1—C6 and C7—C12 phenyl rings is 51.8 (3)°, indicating the molecule is not coplanar. The O3/C13—C15/O1/O2 plane forms dihedral angles of 20.7 (3)° and 47.6 (3)°, respectively, with C1—C6 and C7—C12 phenyl rings. All the bond lengths of the molecule are in normal ranges (Allen et al., 1987).

Related literature top

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 top

Equimolar ethyl 3-bromo-2-(4-chlorophenyl)acrylate and 3,5-difluorophenol reacted in chloroform overnight, giving a colorless solution. Block crystals of the compound were formed by gradual evaporation of the solution in air for a week.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Ethyl 2-(4-chlorophenyl)-3-(3,5-difluorophenoxy)acrylate top

Crystal data top

C₁₇H₁₃ClF₂O₃	F(000) = 696
M_r = 338.72	D_x = 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 = 2.5–25.3°
b = 7.6771 (14) Å	µ = 0.28 mm⁻¹
c = 21.564 (4) Å	T = 298 K
β = 91.40 (3)°	Block, colorless
V = 1572.2 (5) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = 0→11
T_min = 0.939, T_max = 0.947	k = 0→9
3284 measured reflections	l = −26→26

Refinement top

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.283	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.171P)² + 0.5784P] where P = (F_o² + 2F_c²)/3
3090 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₇H₁₃ClF₂O₃	V = 1572.2 (5) Å³
M_r = 338.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4999 (17) Å	µ = 0.28 mm⁻¹
b = 7.6771 (14) Å	T = 298 K
c = 21.564 (4) Å	0.23 × 0.20 × 0.20 mm
β = 91.40 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3090 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2000 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.947	R_int = 0.041
3284 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.283	H-atom parameters constrained
S = 1.08	Δρ_max = 0.48 e Å⁻³
3090 reflections	Δρ_min = −0.53 e Å⁻³
209 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃ClF₂O₃
M_r	338.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.4999 (17), 7.6771 (14), 21.564 (4)
β (°)	91.40 (3)
V (Å³)	1572.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.939, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	3284, 3090, 2000
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.283, 1.08
No. of reflections	3090
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.53

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 30572073), the Natural Science Foundation of Jiangsu Province of China (No. DK2005428), the Medical Science and Technology Development Foundation, Jiangsu Province Department of Health (No. K200402), and the Social Development Foundation of Xuzhou (No. X2003025).

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