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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2374.
Published online 2008 November 20. doi:  10.1107/S1600536808036945
PMCID: PMC2960068

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

Abstract

In the title mol­ecule, C18H16F2O4, the two benzene rings form a dihedral angle of 55.2 (2)°. In the crystal structure, weak inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into chains propagating along the c axis.

Related literature

For a related crystal structure, see Fang et al. (2007 [triangle]). For the properties of phenyl­acetate and styrene derivatives, see: Huang et al. (2007 [triangle]); Li et al. (2007 [triangle]).

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Object name is e-64-o2374-scheme1.jpg

Experimental

Crystal data

  • C18H16F2O4
  • M r = 334.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2374-efi1.jpg
  • a = 17.295 (3) Å
  • b = 7.294 (2) Å
  • c = 14.233 (2) Å
  • β = 113.73 (3)°
  • V = 1643.7 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 (2) K
  • 0.31 × 0.30 × 0.28 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.967, T max = 0.970
  • 3340 measured reflections
  • 3198 independent reflections
  • 1959 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.173
  • S = 1.03
  • 3198 reflections
  • 220 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.31 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/S1600536808036945/cv2469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036945/cv2469Isup2.hkl

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

Acknowledgments

This work was supported by Program in the National Science & Technology of China (No. 2006BAC02A11), Key Technologies R&D Program in the Educational Commission of Hubei Province of China (No. Z20081701), Technologies R&D Program in Hubei Province of China (No. 2007AA301B62).

supplementary crystallographic information

Comment

Phenylacetate and styrene derivatives are important in view of their extensive biological activities. Recently, many of such compounds with good activities were synthesized (Huang et al., 2007; Li et al., 2007). We report in this paper the title new compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compound (Fang et al., 2007). The dihedral angles between C1—C6 and C7—C12 benzene rings is 55.2 (2)°. The O4/C13—C15/O1/O2 plane forms dihedral angles of 5.9 (2)° and 50.2 (2)°, respectively, with C1—C6 and C7—C12 benzene rings. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains propagated along c axis.

Experimental

Ethyl 3-bromo-2-(2,4-difluorophenyl)acrylate (0.1 mmol) and 4-methoxyphenol (0.1 mmol) were reacted in chloroform (20 ml) for 12 h, giving a clear colorless solution. Crytals of the compound were formed by gradual evaporation of the solution.

Refinement

All H atoms were placed in calculated positions with C–H = 0.93–0.97 Å, and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C).

Figures

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

Crystal data

C18H16F2O4F000 = 696
Mr = 334.31Dx = 1.351 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1232 reflections
a = 17.295 (3) Åθ = 2.3–24.5º
b = 7.294 (2) ŵ = 0.11 mm1
c = 14.233 (2) ÅT = 298 (2) K
β = 113.73 (3)ºBlock, colorless
V = 1643.7 (7) Å30.31 × 0.30 × 0.28 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer3198 independent reflections
Radiation source: fine-focus sealed tube1959 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.017
T = 298(2) Kθmax = 26.0º
ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −21→19
Tmin = 0.967, Tmax = 0.970k = −8→0
3340 measured reflectionsl = 0→17

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062  w = 1/[σ2(Fo2) + (0.0671P)2 + 1.0598P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.173(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.43 e Å3
3198 reflectionsΔρmin = −0.31 e Å3
220 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (2)
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
F1−0.10160 (10)0.2759 (3)0.53359 (13)0.0659 (6)
F2−0.21582 (12)0.0299 (3)0.20055 (15)0.0819 (7)
O10.11843 (13)0.3874 (4)0.73642 (16)0.0643 (7)
O20.25578 (13)0.4637 (3)0.80903 (15)0.0544 (6)
O30.52673 (12)0.3660 (3)0.63131 (16)0.0587 (6)
O40.05420 (13)0.2906 (4)0.53932 (19)0.0709 (7)
C1−0.01146 (16)0.2255 (4)0.4503 (2)0.0429 (7)
C2−0.09183 (17)0.2176 (4)0.4484 (2)0.0469 (7)
C3−0.16113 (18)0.1544 (5)0.3667 (2)0.0565 (9)
H3−0.21440.15200.36820.068*
C4−0.14818 (19)0.0949 (5)0.2827 (2)0.0562 (8)
C5−0.0706 (2)0.0975 (5)0.2794 (2)0.0585 (9)
H5−0.06370.05580.22150.070*
C6−0.00211 (18)0.1628 (5)0.3632 (2)0.0524 (8)
H60.05100.16490.36120.063*
C70.28913 (16)0.3613 (4)0.6413 (2)0.0411 (7)
C80.35658 (17)0.2736 (4)0.7170 (2)0.0457 (7)
H80.34790.21470.76990.055*
C90.43628 (17)0.2708 (4)0.7167 (2)0.0485 (8)
H90.48030.21080.76860.058*
C100.45029 (17)0.3582 (4)0.6383 (2)0.0440 (7)
C110.38402 (17)0.4463 (4)0.5619 (2)0.0490 (8)
H110.39280.50410.50870.059*
C120.30513 (17)0.4491 (4)0.5639 (2)0.0460 (7)
H120.26150.51090.51240.055*
C130.13631 (16)0.3039 (4)0.5529 (2)0.0450 (7)
H130.14850.27470.49670.054*
C140.20244 (17)0.3551 (4)0.6398 (2)0.0427 (7)
C150.18686 (18)0.4008 (4)0.7308 (2)0.0476 (7)
C160.2474 (2)0.5001 (6)0.9039 (2)0.0755 (11)
H16A0.22540.39270.92510.091*
H16B0.20850.60090.89500.091*
C170.3315 (3)0.5472 (6)0.9827 (3)0.0840 (12)
H17A0.37000.44820.98960.126*
H17B0.32730.56751.04720.126*
H17C0.35170.65650.96260.126*
C180.59573 (18)0.2753 (5)0.7078 (3)0.0696 (10)
H18A0.60350.32150.77410.104*
H18B0.64600.29670.69620.104*
H18C0.58460.14600.70490.104*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0494 (10)0.1005 (16)0.0561 (11)0.0024 (10)0.0299 (9)−0.0084 (11)
F20.0591 (12)0.1104 (18)0.0587 (12)−0.0114 (12)0.0053 (10)−0.0136 (12)
O10.0527 (13)0.0918 (19)0.0608 (14)−0.0086 (12)0.0358 (11)−0.0089 (13)
O20.0562 (13)0.0704 (16)0.0429 (11)−0.0079 (11)0.0267 (10)−0.0086 (11)
O30.0403 (11)0.0748 (16)0.0661 (14)0.0039 (11)0.0267 (10)0.0059 (12)
O40.0547 (13)0.0828 (18)0.0761 (17)−0.0016 (13)0.0272 (12)−0.0027 (14)
C10.0374 (14)0.0455 (17)0.0454 (16)0.0002 (13)0.0162 (13)0.0024 (14)
C20.0463 (16)0.0555 (19)0.0440 (17)0.0047 (14)0.0235 (14)0.0027 (15)
C30.0394 (16)0.070 (2)0.056 (2)−0.0007 (16)0.0150 (14)0.0078 (18)
C40.0479 (18)0.064 (2)0.0462 (18)−0.0024 (16)0.0084 (15)0.0012 (16)
C50.061 (2)0.072 (2)0.0460 (18)0.0042 (18)0.0242 (16)−0.0044 (17)
C60.0447 (16)0.067 (2)0.0501 (18)−0.0004 (15)0.0239 (14)−0.0033 (16)
C70.0401 (15)0.0405 (17)0.0440 (16)−0.0023 (13)0.0184 (13)−0.0062 (13)
C80.0460 (16)0.0496 (18)0.0452 (16)0.0030 (14)0.0220 (13)0.0043 (14)
C90.0431 (15)0.053 (2)0.0453 (17)0.0089 (14)0.0136 (13)0.0044 (15)
C100.0392 (15)0.0469 (18)0.0484 (17)0.0003 (13)0.0201 (13)−0.0052 (14)
C110.0462 (16)0.058 (2)0.0468 (17)0.0006 (15)0.0232 (14)0.0080 (15)
C120.0409 (15)0.0530 (19)0.0424 (16)0.0041 (14)0.0151 (13)0.0049 (15)
C130.0394 (15)0.0490 (18)0.0511 (17)0.0018 (13)0.0230 (13)0.0003 (14)
C140.0417 (15)0.0436 (17)0.0470 (17)−0.0008 (13)0.0220 (13)0.0003 (14)
C150.0500 (17)0.0467 (18)0.0510 (18)−0.0026 (14)0.0256 (15)0.0012 (15)
C160.085 (3)0.104 (3)0.0470 (19)−0.005 (2)0.0371 (19)−0.005 (2)
C170.109 (3)0.090 (3)0.047 (2)−0.014 (3)0.025 (2)−0.006 (2)
C180.0424 (17)0.086 (3)0.077 (2)0.0103 (18)0.0202 (17)0.003 (2)

Geometric parameters (Å, °)

F1—C21.358 (3)C8—C91.380 (4)
F2—C41.364 (3)C8—H80.9300
O1—C151.222 (3)C9—C101.388 (4)
O2—C151.343 (3)C9—H90.9300
O2—C161.440 (4)C10—C111.381 (4)
O3—C101.366 (3)C11—C121.376 (4)
O3—C181.415 (4)C11—H110.9300
O4—C131.357 (3)C12—H120.9300
O4—C11.401 (3)C13—C141.356 (4)
C1—C21.380 (4)C13—H130.9300
C1—C61.391 (4)C14—C151.464 (4)
C2—C31.370 (4)C16—C171.475 (5)
C3—C41.373 (4)C16—H16A0.9700
C3—H30.9300C16—H16B0.9700
C4—C51.362 (4)C17—H17A0.9600
C5—C61.384 (4)C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C6—H60.9300C18—H18A0.9600
C7—C81.385 (4)C18—H18B0.9600
C7—C121.395 (4)C18—H18C0.9600
C7—C141.491 (4)
C15—O2—C16116.8 (2)C12—C11—C10120.4 (3)
C10—O3—C18117.7 (2)C12—C11—H11119.8
C13—O4—C1125.0 (2)C10—C11—H11119.8
C2—C1—C6116.5 (3)C11—C12—C7121.5 (3)
C2—C1—O4118.4 (3)C11—C12—H12119.2
C6—C1—O4125.1 (2)C7—C12—H12119.2
F1—C2—C3118.8 (3)C14—C13—O4126.9 (3)
F1—C2—C1117.1 (3)C14—C13—H13116.6
C3—C2—C1124.1 (3)O4—C13—H13116.6
C2—C3—C4116.8 (3)C13—C14—C15118.8 (2)
C2—C3—H3121.6C13—C14—C7119.7 (2)
C4—C3—H3121.6C15—C14—C7121.5 (3)
C5—C4—F2119.5 (3)O1—C15—O2122.2 (3)
C5—C4—C3122.3 (3)O1—C15—C14124.6 (3)
F2—C4—C3118.2 (3)O2—C15—C14113.2 (2)
C4—C5—C6119.3 (3)O2—C16—C17108.4 (3)
C4—C5—H5120.4O2—C16—H16A110.0
C6—C5—H5120.4C17—C16—H16A110.0
C5—C6—C1121.0 (3)O2—C16—H16B110.0
C5—C6—H6119.5C17—C16—H16B110.0
C1—C6—H6119.5H16A—C16—H16B108.4
C8—C7—C12117.0 (2)C16—C17—H17A109.5
C8—C7—C14121.6 (3)C16—C17—H17B109.5
C12—C7—C14121.3 (3)H17A—C17—H17B109.5
C9—C8—C7122.3 (3)C16—C17—H17C109.5
C9—C8—H8118.9H17A—C17—H17C109.5
C7—C8—H8118.9H17B—C17—H17C109.5
C8—C9—C10119.6 (3)O3—C18—H18A109.5
C8—C9—H9120.2O3—C18—H18B109.5
C10—C9—H9120.2H18A—C18—H18B109.5
O3—C10—C11116.3 (3)O3—C18—H18C109.5
O3—C10—C9124.4 (3)H18A—C18—H18C109.5
C11—C10—C9119.3 (3)H18B—C18—H18C109.5
C13—O4—C1—C2179.1 (3)C8—C9—C10—C11−0.1 (5)
C13—O4—C1—C60.8 (5)O3—C10—C11—C12−178.6 (3)
C6—C1—C2—F1179.1 (3)C9—C10—C11—C120.6 (5)
O4—C1—C2—F10.6 (4)C10—C11—C12—C7−1.1 (5)
C6—C1—C2—C3−0.6 (5)C8—C7—C12—C111.0 (4)
O4—C1—C2—C3−179.1 (3)C14—C7—C12—C11−176.3 (3)
F1—C2—C3—C4−179.2 (3)C1—O4—C13—C14−175.5 (3)
C1—C2—C3—C40.4 (5)O4—C13—C14—C150.6 (5)
C2—C3—C4—C50.0 (5)O4—C13—C14—C7179.7 (3)
C2—C3—C4—F2179.5 (3)C8—C7—C14—C13−128.4 (3)
F2—C4—C5—C6−179.7 (3)C12—C7—C14—C1348.7 (4)
C3—C4—C5—C6−0.2 (6)C8—C7—C14—C1550.7 (4)
C4—C5—C6—C10.0 (5)C12—C7—C14—C15−132.1 (3)
C2—C1—C6—C50.4 (5)C16—O2—C15—O15.3 (5)
O4—C1—C6—C5178.7 (3)C16—O2—C15—C14−175.9 (3)
C12—C7—C8—C9−0.4 (4)C13—C14—C15—O13.9 (5)
C14—C7—C8—C9176.8 (3)C7—C14—C15—O1−175.2 (3)
C7—C8—C9—C100.0 (5)C13—C14—C15—O2−174.9 (3)
C18—O3—C10—C11−179.3 (3)C7—C14—C15—O26.0 (4)
C18—O3—C10—C91.5 (4)C15—O2—C16—C17173.7 (3)
C8—C9—C10—O3179.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.523.280 (2)140

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2469).

References

  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fang, R.-Q., Li, H.-Q., Shi, L., Xiao, Z.-P. & Zhu, H.-L. (2007). Acta Cryst. E63, o3975.
  • Huang, X.-F., Ruan, B.-F., Wang, X.-T., Xu, C., Ge, H.-M. & Zhu, H.-L. (2007). Eur. J. Med. Chem.42, 263–267. [PubMed]
  • Li, H.-Q., Xu, C., Li, H.-S., Xiao, Z.-P., Shi, L. & Zhu, H.-L. (2007). ChemMedChem, 2, 1361-1369. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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