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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Nov 20;64(Pt 12):o2372. doi: 10.1107/S1600536808036957

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

Hai-Bin Gong a,*, Jie Wang a, Ying Liu a, Lei Wang a
PMCID: PMC2960089  PMID: 21581344

Abstract

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 ▶).graphic file with name e-64-o2372-scheme1.jpg

Experimental

Crystal data

  • C17H13ClF2O3

  • M r = 338.72

  • Monoclinic, Inline graphic

  • 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.

Supplementary Material

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

e-64-o2372-sup1.cif (17.9KB, cif)

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

e-64-o2372-Isup2.hkl (151.6KB, hkl)

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H atoms were included in the riding model approximation with C–H = 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C).

Figures

Fig. 1.

Fig. 1.

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

Crystal data

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
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Data collection

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
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Refinement

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
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Special details

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

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)
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2439).

References

  1. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  2. Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Fang, R.-Q., Li, H.-Q., Shi, L., Xiao, Z.-P. & Zhu, H.-L. (2007). Acta Cryst. E63, o3975.
  5. Liu, X.-H., Lv, P.-C., Li, B. & Zhu, H.-L. (2008). Aust. J. Chem.61, 223–230.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Shi, L., Fang, R.-Q., Li, H.-Q. & Zhu, H.-L. (2007). Acta Cryst. E63, o4041.
  8. Shi, L., Huang, X.-F., Zhu, Z.-W., Li, H.-Q., Xue, J.-Y. & Zhu, H.-L. (2008). Aust. J. Chem.61, 472–475.
  9. Zhang, L.-N., Cao, P., Tan, S.-H., Gu, W., Shi, L. & Zhu, H.-L. (2008). Eur. J. Med. Chem.43, 1543–1551. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-64-o2372-sup1.cif (17.9KB, cif)

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

e-64-o2372-Isup2.hkl (151.6KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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