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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2373.
Published online 2008 November 20. doi:  10.1107/S1600536808037318
PMCID: PMC2959995

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

Abstract

In the mol­ecule of the title compound, C17H13ClF2O3, the dihedral angles formed by the aromatic rings of the chloro­benzene and difluoro­benzene groups with the plane of the acrylate unit are 48.85 (12) and 9.07 (14)°, respectively. In the crystal structure, mol­ecules are linked by weak inter­molecular C—H(...)O hydrogen-bond inter­actions, forming chains along the c axis.

Related literature

For the synthesis and crystal structures of related compounds, see: Li, Xue et al. (2008 [triangle]); Li, Wang & Jian (2008 [triangle]); Lin & Jian (2008 [triangle]); Liu et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2373-scheme1.jpg

Experimental

Crystal data

  • C17H13ClF2O3
  • M r = 338.72
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2373-efi1.jpg
  • a = 16.275 (3) Å
  • b = 7.503 (2) Å
  • c = 13.812 (3) Å
  • β = 111.11 (3)°
  • V = 1573.4 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 298 (2) K
  • 0.30 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.922, T max = 0.973
  • 2956 measured reflections
  • 2823 independent reflections
  • 1566 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.189
  • S = 1.02
  • 2823 reflections
  • 210 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.34 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037318/rz2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037318/rz2266Isup2.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, the synthesis and structure of a number of etheric compounds have been widely investigated (Li, Xue et al., 2008; Li, Wang & Jian, 2008; Lin & Jian, 2008; Liu et al., 2008). We report herein the crystal structure of the new title compound.

In the molecule of the title compound (Fig. 1), the dihedral angles between the aromatic rings of the chlorobenzene and difluorobenzene groups with the plane of the acrylate unit are 48.85 (12) and 9.07 (14)° respectively. All the bond lengths (Allen et al., 1987) and angles are not unusual. In the crystal structure, molecules are linked by weak intermolecular C—H···O hydrogen interactions forming chains along the c axis (Table 1).

Experimental

An equimolar solution of ethyl 3-bromo-2-(4-chlorophenyl)acrylate and 2,4-difluorophenol in chloroform was left to react overnight at room temperature. Block-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent in air for five days.

Refinement

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

Figures

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

Crystal data

C17H13ClF2O3F000 = 696
Mr = 338.72Dx = 1.430 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1002 reflections
a = 16.275 (3) Åθ = 2.4–24.5º
b = 7.503 (2) ŵ = 0.28 mm1
c = 13.812 (3) ÅT = 298 (2) K
β = 111.11 (3)ºBlock, colorless
V = 1573.4 (7) Å30.30 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer2823 independent reflections
Radiation source: fine-focus sealed tube1566 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 298(2) Kθmax = 25.2º
ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −19→18
Tmin = 0.922, Tmax = 0.973k = −9→10
2956 measured reflectionsl = −16→16

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065  w = 1/[σ2(Fo2) + (0.0904P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.38 e Å3
2823 reflectionsΔρmin = −0.34 e Å3
210 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (3)
Secondary atom site location: difference Fourier map

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.

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

xyzUiso*/Ueq
C11.0187 (2)0.7796 (5)0.9699 (3)0.0450 (9)
C21.1022 (2)0.7724 (5)1.0453 (3)0.0473 (9)
C31.1764 (2)0.8337 (6)1.0319 (3)0.0581 (11)
H31.23150.82661.08440.070*
C41.1654 (3)0.9066 (6)0.9368 (3)0.0597 (11)
C51.0851 (3)0.9178 (6)0.8598 (3)0.0621 (12)
H51.07970.96910.79640.074*
C61.0121 (3)0.8535 (6)0.8755 (3)0.0561 (11)
H60.95740.85960.82220.067*
C70.7054 (2)0.6469 (5)0.8670 (3)0.0423 (9)
C80.6325 (2)0.7234 (5)0.8808 (3)0.0540 (10)
H80.63760.76630.94590.065*
C90.5527 (2)0.7366 (6)0.7996 (3)0.0571 (11)
H90.50450.78760.81000.069*
C100.5451 (2)0.6742 (5)0.7036 (3)0.0543 (11)
C110.6147 (3)0.5952 (6)0.6881 (3)0.0572 (11)
H110.60860.55130.62290.069*
C120.6947 (2)0.5804 (5)0.7696 (3)0.0482 (10)
H120.74180.52520.75880.058*
C130.8635 (2)0.7022 (5)0.9293 (3)0.0465 (9)
H130.85260.73730.86120.056*
C140.7936 (2)0.6482 (5)0.9511 (3)0.0426 (9)
C150.8065 (2)0.5946 (5)1.0579 (3)0.0483 (10)
C160.7414 (3)0.4744 (6)1.1715 (3)0.0627 (12)
H16A0.75800.57541.21850.075*
H16B0.78580.38241.19750.075*
C170.6537 (3)0.4055 (7)1.1643 (3)0.0716 (13)
H17A0.60930.49221.13030.107*
H17B0.65380.38311.23270.107*
H17C0.64150.29681.12500.107*
Cl10.44478 (7)0.69754 (19)0.60039 (9)0.0891 (5)
F11.10978 (13)0.7012 (3)1.13855 (15)0.0663 (7)
F21.23761 (16)0.9699 (4)0.9209 (2)0.0858 (9)
O30.94846 (18)0.7113 (4)0.9954 (2)0.0723 (9)
O10.87704 (17)0.6033 (4)1.13049 (18)0.0666 (9)
O20.73412 (16)0.5282 (4)1.06775 (17)0.0525 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.043 (2)0.048 (2)0.043 (2)−0.0032 (18)0.0138 (16)−0.0068 (18)
C20.047 (2)0.057 (2)0.0348 (19)0.0045 (19)0.0106 (16)−0.0028 (18)
C30.042 (2)0.078 (3)0.049 (2)−0.007 (2)0.0090 (17)−0.010 (2)
C40.053 (2)0.070 (3)0.062 (3)−0.008 (2)0.028 (2)−0.011 (2)
C50.071 (3)0.074 (3)0.044 (2)−0.001 (2)0.024 (2)0.001 (2)
C60.049 (2)0.073 (3)0.040 (2)−0.005 (2)0.0084 (17)−0.002 (2)
C70.042 (2)0.043 (2)0.039 (2)−0.0041 (17)0.0112 (15)0.0051 (16)
C80.048 (2)0.062 (3)0.046 (2)0.002 (2)0.0106 (17)−0.004 (2)
C90.044 (2)0.063 (3)0.060 (3)0.007 (2)0.0137 (19)0.004 (2)
C100.044 (2)0.056 (3)0.048 (2)−0.003 (2)−0.0007 (17)0.0099 (19)
C110.059 (2)0.067 (3)0.038 (2)−0.006 (2)0.0081 (18)−0.001 (2)
C120.048 (2)0.054 (2)0.041 (2)−0.0005 (19)0.0140 (16)−0.0013 (18)
C130.045 (2)0.055 (2)0.0329 (18)0.0044 (19)0.0056 (16)0.0002 (17)
C140.042 (2)0.047 (2)0.0327 (18)0.0010 (17)0.0072 (15)−0.0008 (16)
C150.049 (2)0.052 (2)0.039 (2)−0.0023 (19)0.0113 (18)−0.0016 (18)
C160.069 (3)0.076 (3)0.038 (2)−0.006 (2)0.0140 (19)0.002 (2)
C170.075 (3)0.084 (3)0.057 (3)−0.013 (3)0.025 (2)−0.001 (2)
Cl10.0572 (7)0.1132 (11)0.0671 (8)0.0017 (7)−0.0137 (5)0.0169 (7)
F10.0541 (13)0.0976 (19)0.0380 (12)−0.0022 (13)0.0054 (10)0.0107 (12)
F20.0689 (16)0.119 (2)0.0845 (18)−0.0260 (16)0.0462 (14)−0.0119 (17)
O30.0592 (18)0.086 (2)0.0644 (19)−0.0014 (17)0.0134 (15)−0.0021 (17)
O10.0509 (16)0.099 (2)0.0377 (15)−0.0153 (16)0.0018 (12)0.0063 (15)
O20.0487 (15)0.0678 (18)0.0382 (13)−0.0050 (14)0.0123 (11)0.0020 (13)

Geometric parameters (Å, °)

C1—C61.384 (5)C10—C111.363 (5)
C1—C21.385 (5)C10—Cl11.747 (4)
C1—O31.409 (4)C11—C121.385 (5)
C2—F11.358 (4)C11—H110.9300
C2—C31.365 (5)C12—H120.9300
C3—C41.373 (6)C13—C141.340 (5)
C3—H30.9300C13—O31.356 (4)
C4—F21.357 (4)C13—H130.9300
C4—C51.359 (5)C14—C151.469 (5)
C5—C61.370 (5)C15—O11.224 (4)
C5—H50.9300C15—O21.331 (4)
C6—H60.9300C16—O21.452 (4)
C7—C121.386 (5)C16—C171.486 (5)
C7—C81.392 (5)C16—H16A0.9700
C7—C141.486 (4)C16—H16B0.9700
C8—C91.380 (5)C17—H17A0.9600
C8—H80.9300C17—H17B0.9600
C9—C101.368 (5)C17—H17C0.9600
C9—H90.9300
C6—C1—C2116.5 (3)C10—C11—C12119.9 (4)
C6—C1—O3125.9 (3)C10—C11—H11120.1
C2—C1—O3117.6 (3)C12—C11—H11120.1
F1—C2—C3118.6 (3)C11—C12—C7120.8 (4)
F1—C2—C1117.2 (3)C11—C12—H12119.6
C3—C2—C1124.1 (4)C7—C12—H12119.6
C2—C3—C4116.6 (4)C14—C13—O3127.3 (3)
C2—C3—H3121.7C14—C13—H13116.3
C4—C3—H3121.7O3—C13—H13116.3
F2—C4—C5119.7 (4)C13—C14—C15118.8 (3)
F2—C4—C3118.2 (4)C13—C14—C7119.1 (3)
C5—C4—C3122.1 (4)C15—C14—C7122.1 (3)
C4—C5—C6119.8 (4)O1—C15—O2122.7 (3)
C4—C5—H5120.1O1—C15—C14124.1 (4)
C6—C5—H5120.1O2—C15—C14113.2 (3)
C5—C6—C1120.9 (4)O2—C16—C17107.1 (3)
C5—C6—H6119.6O2—C16—H16A110.3
C1—C6—H6119.6C17—C16—H16A110.3
C12—C7—C8117.8 (3)O2—C16—H16B110.3
C12—C7—C14120.6 (3)C17—C16—H16B110.3
C8—C7—C14121.4 (3)H16A—C16—H16B108.5
C9—C8—C7121.1 (4)C16—C17—H17A109.5
C9—C8—H8119.4C16—C17—H17B109.5
C7—C8—H8119.4H17A—C17—H17B109.5
C10—C9—C8119.6 (4)C16—C17—H17C109.5
C10—C9—H9120.2H17A—C17—H17C109.5
C8—C9—H9120.2H17B—C17—H17C109.5
C11—C10—C9120.7 (3)C13—O3—C1124.9 (3)
C11—C10—Cl1120.0 (3)C15—O2—C16116.4 (3)
C9—C10—Cl1119.2 (3)
C6—C1—C2—F1179.6 (3)C10—C11—C12—C7−0.7 (6)
O3—C1—C2—F1−0.6 (5)C8—C7—C12—C112.1 (6)
C6—C1—C2—C30.4 (6)C14—C7—C12—C11−173.4 (4)
O3—C1—C2—C3−179.8 (4)O3—C13—C14—C151.2 (6)
F1—C2—C3—C4−179.2 (3)O3—C13—C14—C7−179.6 (3)
C1—C2—C3—C40.0 (6)C12—C7—C14—C1344.5 (5)
C2—C3—C4—F2179.6 (4)C8—C7—C14—C13−130.9 (4)
C2—C3—C4—C50.1 (7)C12—C7—C14—C15−136.4 (4)
F2—C4—C5—C6179.8 (4)C8—C7—C14—C1548.3 (5)
C3—C4—C5—C6−0.7 (7)C13—C14—C15—O13.5 (6)
C4—C5—C6—C11.1 (7)C7—C14—C15—O1−175.7 (4)
C2—C1—C6—C5−1.0 (6)C13—C14—C15—O2−174.1 (3)
O3—C1—C6—C5179.3 (4)C7—C14—C15—O26.8 (5)
C12—C7—C8—C9−1.6 (6)C14—C13—O3—C1−175.8 (4)
C14—C7—C8—C9173.9 (4)C6—C1—O3—C132.4 (6)
C7—C8—C9—C10−0.2 (6)C2—C1—O3—C13−177.4 (4)
C8—C9—C10—C111.6 (6)O1—C15—O2—C163.3 (6)
C8—C9—C10—Cl1−178.1 (3)C14—C15—O2—C16−179.1 (3)
C9—C10—C11—C12−1.2 (6)C17—C16—O2—C15179.9 (3)
Cl1—C10—C11—C12178.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.321 (4)146

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2266).

References

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  • Bruker (2001). SADABS ruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
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  • Li, H.-Q., Xue, J.-Y., Shi, L., Gui, S.-Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem.43, 662–667. [PubMed]
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  • Liu, X.-H., Cui, P., Song, B.-A., Bhadury, P. S., Zhu, H.-L. & Wang, S.-F. (2008). Bioorg. Med. Chem.16, 4075-4082. [PubMed]
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