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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2471.
Published online 2008 November 29. doi:  10.1107/S1600536808039263
PMCID: PMC2959914

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

Abstract

The title compound, C19H19ClO5, displays a dihedral angle of 74.7 (3)° between the mean planes of the 4-chloro­phenyl and phenol rings.

Related literature

For phenyl­acetate and styrene derivatives, see: Fang et al. (2007 [triangle]); Huang et al. (2007 [triangle]); Li et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2471-scheme1.jpg

Experimental

Crystal data

  • C19H19ClO5
  • M r = 362.80
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2471-efi1.jpg
  • a = 9.601 (2) Å
  • b = 9.607 (3) Å
  • c = 10.368 (2) Å
  • α = 77.84 (2)°
  • β = 75.42 (3)°
  • γ = 87.40 (3)°
  • V = 904.7 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.932, T max = 0.977
  • 6132 measured reflections
  • 3280 independent reflections
  • 2153 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.147
  • S = 1.03
  • 3280 reflections
  • 230 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.40 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039263/su2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039263/su2078Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

Phenylacetate and styrene derivatives are important for their extensive biological activities. Recently a large number of such compounds have been synthesized, and found to have good biological activities (Fang et al., 2007; Huang et al., 2007; Li et al., 2007). Here report on the crystal structure of the new acrylate compound, (I).

The molecular structure of compound (I) is illustrated in Fig. 1. All the bond lengths and angles are within normal values. The dihedral angle between the mean plane of the 4-chlorophenyl ring (C1—C6) and the mean plane through the phenol ring (C7—C12) is 74.7 (3)°. The [O5/C13—C15/O1/O2] mean plane forms dihedral angles of 23.6 (3)° and 59.6 (3)° with the mean planes of rings (C1—C6) and (C7—C12), respectively.

In the crystal structure the molecules stack head-to-head along the c direction.

Experimental

Ethyl 3-bromo-2-(4-chlorophenyl)acrylate (0.1 mmol) and 3,5-dimethoxyphenol (0.1 mmol) were reacted in chloroform for 12 h, giving a clear colorless solution. Crytals of compound (I) were formed by gradual evaporation of the solution.

Refinement

All the H-atoms were placed in calculated positions and treated as rding atoms: C–H = 0.93–0.97 Å with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of compound (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probabilty level.

Crystal data

C19H19ClO5Z = 2
Mr = 362.80F000 = 382
Triclinic, P1Dx = 1.335 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.601 (2) ÅCell parameters from 1273 reflections
b = 9.607 (3) Åθ = 2.4–25.3º
c = 10.368 (2) ŵ = 0.24 mm1
α = 77.84 (2)ºT = 298 (2) K
β = 75.42 (3)ºBlock, colorless
γ = 87.40 (3)º0.30 × 0.20 × 0.10 mm
V = 904.7 (4) Å3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer3280 independent reflections
Radiation source: fine-focus sealed tube2153 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 298(2) Kθmax = 25.3º
ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −11→11
Tmin = 0.932, Tmax = 0.977k = −11→11
6132 measured reflectionsl = −12→12

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058  w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3443P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.48 e Å3
3280 reflectionsΔρmin = −0.40 e Å3
230 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (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
C10.9387 (3)0.1311 (3)0.7046 (3)0.0377 (7)
C21.0552 (3)0.1122 (3)0.5995 (3)0.0393 (7)
H21.07970.18120.51970.047*
C31.1345 (3)−0.0115 (3)0.6159 (3)0.0411 (7)
C41.0993 (3)−0.1153 (3)0.7352 (3)0.0433 (8)
H41.1517−0.19900.74470.052*
C50.9853 (3)−0.0911 (3)0.8389 (3)0.0399 (7)
C60.9046 (3)0.0313 (3)0.8241 (3)0.0424 (7)
H60.82760.04610.89470.051*
C70.6961 (3)0.5299 (3)0.6619 (3)0.0341 (7)
C80.5498 (3)0.5569 (3)0.6821 (3)0.0429 (7)
H80.50040.53040.62450.051*
C90.4755 (3)0.6225 (3)0.7858 (3)0.0476 (8)
H90.37730.63910.79820.057*
C100.5490 (3)0.6624 (3)0.8697 (3)0.0442 (8)
C110.6936 (3)0.6343 (3)0.8557 (3)0.0472 (8)
H110.74140.65910.91540.057*
C120.7665 (3)0.5688 (3)0.7519 (3)0.0416 (7)
H120.86420.55030.74170.050*
C130.8483 (3)0.3402 (3)0.5672 (3)0.0400 (7)
H130.89870.30890.48960.048*
C140.7768 (3)0.4626 (3)0.5486 (3)0.0352 (7)
C150.7837 (3)0.5296 (3)0.4060 (3)0.0378 (7)
C160.7084 (4)0.7295 (3)0.2597 (3)0.0469 (8)
H16A0.69150.66670.20310.056*
H16B0.80170.77500.21820.056*
C170.5928 (4)0.8392 (4)0.2728 (4)0.0638 (10)
H17A0.50090.79290.31160.096*
H17B0.59410.89590.18440.096*
H17C0.60950.89930.33070.096*
C181.0305 (4)−0.3072 (3)0.9843 (3)0.0595 (10)
H18A1.0336−0.36270.91670.089*
H18B0.9906−0.36391.07310.089*
H18C1.1262−0.27730.97880.089*
C191.2980 (4)0.0648 (3)0.3998 (3)0.0580 (9)
H19A1.22290.08320.35250.087*
H19B1.38220.03250.34180.087*
H19C1.32060.15060.42420.087*
Cl10.45938 (11)0.75361 (11)0.99503 (10)0.0720 (4)
O50.8538 (3)0.2570 (3)0.6900 (3)0.0694 (7)
O10.8506 (2)0.4862 (2)0.3068 (2)0.0560 (6)
O20.7048 (2)0.6494 (2)0.39530 (19)0.0412 (5)
O30.9429 (2)−0.1850 (2)0.9607 (2)0.0501 (6)
O41.2510 (2)−0.0425 (2)0.5203 (2)0.0545 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0428 (17)0.0281 (15)0.0451 (17)0.0087 (13)−0.0152 (14)−0.0104 (13)
C20.0505 (19)0.0275 (15)0.0389 (16)0.0037 (14)−0.0133 (14)−0.0030 (13)
C30.0410 (17)0.0355 (16)0.0457 (18)0.0035 (14)−0.0090 (14)−0.0092 (14)
C40.0502 (19)0.0317 (16)0.0469 (18)0.0087 (14)−0.0154 (15)−0.0037 (14)
C50.0468 (18)0.0340 (16)0.0392 (17)0.0037 (14)−0.0143 (14)−0.0047 (13)
C60.0441 (18)0.0400 (17)0.0417 (17)0.0064 (14)−0.0088 (14)−0.0085 (14)
C70.0346 (16)0.0272 (14)0.0382 (16)0.0018 (12)−0.0096 (13)−0.0011 (12)
C80.0400 (18)0.0495 (19)0.0417 (17)−0.0017 (14)−0.0125 (14)−0.0117 (14)
C90.0367 (17)0.056 (2)0.0488 (19)0.0084 (15)−0.0066 (15)−0.0145 (16)
C100.051 (2)0.0403 (17)0.0370 (17)0.0070 (15)−0.0037 (15)−0.0091 (14)
C110.053 (2)0.0493 (19)0.0432 (18)0.0025 (16)−0.0194 (15)−0.0101 (15)
C120.0383 (17)0.0409 (17)0.0461 (17)0.0061 (14)−0.0136 (14)−0.0073 (14)
C130.0464 (18)0.0365 (17)0.0361 (16)0.0070 (14)−0.0114 (14)−0.0048 (13)
C140.0323 (16)0.0321 (15)0.0404 (16)0.0037 (13)−0.0078 (13)−0.0078 (13)
C150.0351 (16)0.0352 (16)0.0441 (17)0.0025 (13)−0.0106 (14)−0.0097 (13)
C160.059 (2)0.0425 (18)0.0396 (17)0.0061 (16)−0.0195 (16)−0.0024 (14)
C170.082 (3)0.053 (2)0.066 (2)0.0239 (19)−0.038 (2)−0.0124 (18)
C180.074 (2)0.0423 (19)0.053 (2)0.0162 (18)−0.0132 (18)0.0046 (16)
C190.063 (2)0.046 (2)0.051 (2)0.0065 (17)0.0064 (17)−0.0061 (16)
Cl10.0792 (7)0.0803 (7)0.0582 (6)0.0120 (5)−0.0040 (5)−0.0363 (5)
O50.0825 (19)0.0557 (15)0.0689 (17)0.0162 (14)−0.0212 (14)−0.0105 (13)
O10.0676 (16)0.0554 (14)0.0401 (12)0.0240 (12)−0.0068 (11)−0.0121 (11)
O20.0476 (12)0.0376 (11)0.0373 (11)0.0130 (10)−0.0115 (9)−0.0068 (9)
O30.0569 (14)0.0403 (12)0.0454 (12)0.0099 (11)−0.0100 (11)0.0031 (10)
O40.0587 (15)0.0414 (13)0.0512 (13)0.0129 (11)0.0011 (11)−0.0028 (11)

Geometric parameters (Å, °)

C1—C61.373 (4)C12—H120.9300
C1—C21.387 (4)C13—C141.338 (4)
C1—O51.430 (3)C13—O51.366 (4)
C2—C31.385 (4)C13—H130.9300
C2—H20.9300C14—C151.469 (4)
C3—O41.363 (3)C15—O11.212 (3)
C3—C41.392 (4)C15—O21.349 (3)
C4—C51.378 (4)C16—O21.446 (3)
C4—H40.9300C16—C171.496 (4)
C5—O31.367 (3)C16—H16A0.9700
C5—C61.381 (4)C16—H16B0.9700
C6—H60.9300C17—H17A0.9600
C7—C81.388 (4)C17—H17B0.9600
C7—C121.398 (4)C17—H17C0.9600
C7—C141.487 (4)C18—O31.427 (4)
C8—C91.385 (4)C18—H18A0.9600
C8—H80.9300C18—H18B0.9600
C9—C101.370 (4)C18—H18C0.9600
C9—H90.9300C19—O41.429 (4)
C10—C111.379 (4)C19—H19A0.9600
C10—Cl11.745 (3)C19—H19B0.9600
C11—C121.382 (4)C19—H19C0.9600
C11—H110.9300
C6—C1—C2120.9 (3)C14—C13—H13117.1
C6—C1—O5119.2 (3)O5—C13—H13117.1
C2—C1—O5119.9 (3)C13—C14—C15115.3 (3)
C3—C2—C1118.7 (3)C13—C14—C7123.7 (3)
C3—C2—H2120.7C15—C14—C7121.0 (2)
C1—C2—H2120.7O1—C15—O2122.0 (3)
O4—C3—C2124.2 (3)O1—C15—C14126.0 (3)
O4—C3—C4114.6 (3)O2—C15—C14112.0 (2)
C2—C3—C4121.2 (3)O2—C16—C17107.5 (3)
C5—C4—C3118.5 (3)O2—C16—H16A110.2
C5—C4—H4120.7C17—C16—H16A110.2
C3—C4—H4120.7O2—C16—H16B110.2
O3—C5—C4123.3 (3)C17—C16—H16B110.2
O3—C5—C6115.7 (3)H16A—C16—H16B108.5
C4—C5—C6121.0 (3)C16—C17—H17A109.5
C1—C6—C5119.7 (3)C16—C17—H17B109.5
C1—C6—H6120.2H17A—C17—H17B109.5
C5—C6—H6120.2C16—C17—H17C109.5
C8—C7—C12117.6 (3)H17A—C17—H17C109.5
C8—C7—C14121.8 (3)H17B—C17—H17C109.5
C12—C7—C14120.6 (3)O3—C18—H18A109.5
C9—C8—C7121.7 (3)O3—C18—H18B109.5
C9—C8—H8119.1H18A—C18—H18B109.5
C7—C8—H8119.1O3—C18—H18C109.5
C10—C9—C8118.9 (3)H18A—C18—H18C109.5
C10—C9—H9120.5H18B—C18—H18C109.5
C8—C9—H9120.5O4—C19—H19A109.5
C9—C10—C11121.4 (3)O4—C19—H19B109.5
C9—C10—Cl1119.6 (2)H19A—C19—H19B109.5
C11—C10—Cl1119.1 (3)O4—C19—H19C109.5
C10—C11—C12119.1 (3)H19A—C19—H19C109.5
C10—C11—H11120.4H19B—C19—H19C109.5
C12—C11—H11120.4C13—O5—C1123.7 (2)
C11—C12—C7121.2 (3)C15—O2—C16117.4 (2)
C11—C12—H12119.4C5—O3—C18117.4 (2)
C7—C12—H12119.4C3—O4—C19116.9 (2)
C14—C13—O5125.8 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2078).

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). Chem. Med. Chem.2, 1361–1369. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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