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Acta Cryst. (2008). E64, o2293    [ doi:10.1107/S160053680803571X ]

Ethyl 3-(4-hydroxyphenoxy)-2-(4-methoxyphenyl)acrylate

J. Hou

Abstract top

In the title compound, C18H18O5, the dihedral angle between the two benzene rings is 55.2 (3)°. The ethyl acrylate linkage is planar and forms dihedral angles of 21.3 (3) and 41.0 (3)°, respectively, with the hydroxyphenyl and methoxyphenyl rings. In the crystal structure, molecules are linked into zigzag chains along the b axis by O-H...O hydrogen bonds.

Comment top

Phenylacetate and styrene derivetives are important for their extensive biological activities. Recently a great deal of such kinds of compounds were synthesized, which were found to exhibit good activities (Huang et al., 2008; Li et al., 2008; Liu et al., 2008; Shi et al., 2008; Xiao et al., 2008)

Bond lengths in the title compound (Fig.1) are within normal ranges (Allen et al., 1987). The dihedral angle between the C1—C6 and C7—C12 benzene rings is 55.2 (3)°. The O1/O2/C13—C17 plane forms dihedral angles of 21.3 (3)° and 41.0 (3)°, respectively, with C1—C6 and C7—C12 benzene rings. In the crytal structure, O—H···O hydrogen bonds (Table 1) link the molecules into zigzag chains along the b axis (Fig. 2).

Related literature top

For general background, see: Huang et al. (2008); Li et al. (2008); Liu et al. (2008); Shi et al. (2008); Xiao et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

Equimolar ethyl 3-bromo-2-(4-methoxyphenyl)acrylate and hydroquinone reacted in chloroform overnight, gave the title compound in high yield (88%). Colourless crystals of the title compound were grown by slow evaparation of a methanol solution.

Refinement top

H atoms were positioned geometrically (O—H = 0.82 Å and C—H = 0.93 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O). In the absence of significant anomalous scattering, Friedel pairs were merged prior to the final refinement.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.
Ethyl 3-(4-hydroxyphenoxy)-2-(4-methoxyphenyl)acrylate top
Crystal data top
C18H18O5F(000) = 664
Mr = 314.33Dx = 1.304 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1213 reflections
a = 7.4773 (16) Åθ = 3.2–26.1°
b = 11.661 (2) ŵ = 0.10 mm−1
c = 18.417 (4) ÅT = 298 K
V = 1605.8 (6) Å3Prism, colourless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1822 independent reflections
Radiation source: fine-focus sealed tube1486 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −9→9
Tmin = 0.963, Tmax = 0.981k = −10→14
5527 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0689P)2 + 0.4887P]
where P = (Fo2 + 2Fc2)/3
1822 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C18H18O5V = 1605.8 (6) Å3
Mr = 314.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.4773 (16) ŵ = 0.10 mm−1
b = 11.661 (2) ÅT = 298 K
c = 18.417 (4) Å0.40 × 0.30 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		1822 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1486 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.981Rint = 0.032
5527 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.134Δρmax = 0.26 e Å−3
S = 1.05Δρmin = −0.34 e Å−3
1822 reflectionsAbsolute structure: ?
211 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.0040 (5)0.4964 (3)0.73124 (16)0.0401 (8)
C20.0773 (6)0.4306 (3)0.78656 (17)0.0485 (9)
H20.14630.36690.77500.058*
C30.0490 (6)0.4589 (3)0.85909 (18)0.0489 (10)
H30.09900.41440.89570.059*
C4−0.0543 (6)0.5537 (3)0.87635 (17)0.0444 (9)
C5−0.1311 (5)0.6181 (3)0.82193 (17)0.0454 (9)
H5−0.20190.68100.83350.054*
C6−0.1024 (5)0.5887 (3)0.74921 (17)0.0471 (9)
H6−0.15560.63190.71260.057*
C70.0419 (5)0.6087 (3)0.47594 (16)0.0370 (7)
C8−0.0503 (5)0.5959 (3)0.41071 (17)0.0407 (8)
H8−0.09700.52460.39840.049*
C9−0.0734 (5)0.6872 (3)0.36402 (17)0.0462 (9)
H9−0.13360.67620.32040.055*
C10−0.0083 (5)0.7946 (3)0.38124 (18)0.0441 (9)
C110.0842 (5)0.8107 (3)0.44550 (19)0.0463 (9)
H110.12870.88260.45780.056*
C120.1095 (5)0.7176 (3)0.49137 (19)0.0440 (9)
H120.17410.72820.53400.053*
C130.0301 (5)0.5385 (3)0.60130 (17)0.0415 (8)
H130.00000.61380.61230.050*
C140.0590 (5)0.5141 (3)0.52943 (17)0.0394 (8)
C150.1049 (5)0.3973 (3)0.50927 (17)0.0397 (8)
C160.1644 (7)0.2682 (3)0.41167 (18)0.0513 (10)
H16A0.07750.21210.42810.062*
H16B0.28140.24620.42970.062*
C170.1658 (6)0.2743 (3)0.33027 (17)0.0549 (10)
H17A0.04550.28260.31280.082*
H17B0.21700.20530.31090.082*
H17C0.23570.33900.31500.082*
C18−0.0024 (7)0.9941 (3)0.3518 (3)0.0668 (13)
H18A−0.06561.01390.39540.100*
H18B−0.03741.04500.31340.100*
H18C0.12391.00080.36000.100*
O50.0407 (4)0.4650 (3)0.65807 (14)0.0662 (8)
O10.1315 (4)0.3188 (2)0.55214 (12)0.0541 (7)
O20.1174 (4)0.3810 (2)0.43764 (12)0.0468 (7)
O3−0.0441 (5)0.8795 (2)0.33197 (14)0.0618 (8)
O4−0.0756 (5)0.5803 (2)0.94804 (12)0.0601 (8)
H4−0.10190.64830.95200.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.047 (2)0.0446 (17)0.0288 (16)−0.0058 (17)−0.0002 (15)−0.0054 (14)
C20.062 (2)0.0465 (19)0.0373 (17)−0.003 (2)0.0026 (18)−0.0020 (15)
C30.071 (3)0.0439 (18)0.0320 (16)−0.008 (2)−0.0065 (18)0.0043 (15)
C40.060 (2)0.0450 (19)0.0281 (15)−0.011 (2)0.0040 (16)−0.0038 (14)
C50.053 (2)0.0458 (19)0.0379 (18)0.0008 (19)0.0010 (17)−0.0091 (16)
C60.054 (2)0.056 (2)0.0313 (16)0.002 (2)−0.0039 (16)0.0043 (16)
C70.0403 (17)0.0406 (17)0.0302 (15)−0.0005 (17)0.0009 (15)−0.0029 (14)
C80.046 (2)0.0405 (18)0.0352 (17)−0.0062 (17)−0.0021 (16)−0.0060 (14)
C90.058 (2)0.052 (2)0.0282 (15)−0.004 (2)−0.0067 (16)−0.0010 (15)
C100.048 (2)0.0461 (19)0.0376 (18)−0.0014 (18)0.0041 (17)−0.0001 (15)
C110.053 (2)0.0395 (17)0.0464 (19)−0.0077 (18)0.0007 (18)−0.0043 (16)
C120.045 (2)0.049 (2)0.0385 (18)−0.0055 (18)−0.0048 (17)−0.0065 (16)
C130.048 (2)0.0437 (18)0.0329 (16)0.0006 (18)−0.0030 (15)−0.0030 (15)
C140.0419 (19)0.0441 (18)0.0321 (16)−0.0035 (17)−0.0041 (16)−0.0026 (14)
C150.048 (2)0.0404 (17)0.0303 (16)−0.0023 (18)0.0012 (16)−0.0017 (14)
C160.081 (3)0.0400 (19)0.0332 (17)0.001 (2)0.002 (2)−0.0028 (15)
C170.075 (3)0.055 (2)0.0348 (18)−0.005 (2)0.0052 (19)−0.0094 (17)
C180.068 (3)0.047 (2)0.086 (3)0.000 (2)0.000 (3)0.014 (2)
O50.080 (2)0.0751 (18)0.0436 (14)0.0007 (19)0.0009 (15)−0.0010 (14)
O10.087 (2)0.0428 (13)0.0328 (12)0.0010 (15)0.0023 (14)0.0029 (11)
O20.0716 (17)0.0392 (12)0.0296 (11)0.0028 (13)0.0012 (13)−0.0037 (10)
O30.092 (2)0.0451 (14)0.0488 (14)−0.0026 (16)−0.0042 (16)0.0095 (12)
O40.098 (2)0.0527 (15)0.0292 (12)−0.0039 (18)0.0073 (14)−0.0048 (11)
Geometric parameters (Å, °) top
C1—C61.379 (5)C11—C121.388 (5)
C1—C21.388 (5)C11—H110.93
C1—O51.423 (4)C12—H120.93
C2—C31.392 (5)C13—O51.354 (4)
C2—H20.93C13—C141.371 (4)
C3—C41.386 (5)C13—H130.93
C3—H30.93C14—C151.454 (4)
C4—O41.366 (4)C15—O11.225 (4)
C4—C51.377 (5)C15—O21.336 (4)
C5—C61.399 (5)C16—O21.444 (4)
C5—H50.93C16—C171.501 (5)
C6—H60.93C16—H16A0.97
C7—C81.393 (5)C16—H16B0.97
C7—C121.396 (4)C17—H17A0.96
C7—C141.484 (4)C17—H17B0.96
C8—C91.379 (5)C17—H17C0.96
C8—H80.93C18—O31.420 (5)
C9—C101.381 (5)C18—H18A0.96
C9—H90.93C18—H18B0.96
C10—O31.369 (4)C18—H18C0.96
C10—C111.384 (5)O4—H40.82
C6—C1—C2118.9 (3)C11—C12—H12118.7
C6—C1—O5122.7 (3)C7—C12—H12118.7
C2—C1—O5118.5 (3)O5—C13—C14127.3 (3)
C1—C2—C3120.9 (4)O5—C13—H13116.4
C1—C2—H2119.6C14—C13—H13116.4
C3—C2—H2119.6C13—C14—C15118.5 (3)
C4—C3—C2119.6 (3)C13—C14—C7118.3 (3)
C4—C3—H3120.2C15—C14—C7123.2 (3)
C2—C3—H3120.2O1—C15—O2121.3 (3)
O4—C4—C5122.1 (3)O1—C15—C14125.0 (3)
O4—C4—C3117.9 (3)O2—C15—C14113.7 (3)
C5—C4—C3120.0 (3)O2—C16—C17106.8 (3)
C4—C5—C6120.0 (3)O2—C16—H16A110.4
C4—C5—H5120.0C17—C16—H16A110.4
C6—C5—H5120.0O2—C16—H16B110.4
C1—C6—C5120.6 (3)C17—C16—H16B110.4
C1—C6—H6119.7H16A—C16—H16B108.6
C5—C6—H6119.7C16—C17—H17A109.5
C8—C7—C12116.9 (3)C16—C17—H17B109.5
C8—C7—C14122.3 (3)H17A—C17—H17B109.5
C12—C7—C14120.7 (3)C16—C17—H17C109.5
C9—C8—C7121.1 (3)H17A—C17—H17C109.5
C9—C8—H8119.4H17B—C17—H17C109.5
C7—C8—H8119.4O3—C18—H18A109.5
C8—C9—C10120.9 (3)O3—C18—H18B109.5
C8—C9—H9119.6H18A—C18—H18B109.5
C10—C9—H9119.6O3—C18—H18C109.5
O3—C10—C9115.8 (3)H18A—C18—H18C109.5
O3—C10—C11124.5 (3)H18B—C18—H18C109.5
C9—C10—C11119.7 (3)C13—O5—C1123.8 (3)
C10—C11—C12118.9 (3)C15—O2—C16118.3 (3)
C10—C11—H11120.6C10—O3—C18117.8 (3)
C12—C11—H11120.6C4—O4—H4109.5
C11—C12—C7122.5 (3)
C6—C1—C2—C3−1.9 (6)C14—C7—C12—C11−174.8 (3)
O5—C1—C2—C3178.6 (3)O5—C13—C14—C150.5 (6)
C1—C2—C3—C40.2 (6)O5—C13—C14—C7−179.4 (3)
C2—C3—C4—O4−178.4 (4)C8—C7—C14—C13−134.7 (4)
C2—C3—C4—C51.2 (6)C12—C7—C14—C1341.3 (5)
O4—C4—C5—C6178.7 (4)C8—C7—C14—C1545.3 (5)
C3—C4—C5—C6−1.0 (6)C12—C7—C14—C15−138.6 (4)
C2—C1—C6—C52.2 (6)C13—C14—C15—O1−4.9 (6)
O5—C1—C6—C5−178.4 (3)C7—C14—C15—O1175.0 (4)
C4—C5—C6—C1−0.7 (6)C13—C14—C15—O2175.4 (3)
C12—C7—C8—C9−0.2 (5)C7—C14—C15—O2−4.7 (5)
C14—C7—C8—C9176.0 (3)C14—C13—O5—C1−178.3 (4)
C7—C8—C9—C10−1.1 (6)C6—C1—O5—C1323.2 (6)
C8—C9—C10—O3−178.0 (4)C2—C1—O5—C13−157.3 (4)
C8—C9—C10—C111.2 (6)O1—C15—O2—C16−0.4 (6)
O3—C10—C11—C12179.1 (4)C14—C15—O2—C16179.3 (3)
C9—C10—C11—C120.0 (6)C17—C16—O2—C15179.1 (3)
C10—C11—C12—C7−1.4 (6)C9—C10—O3—C18171.3 (4)
C8—C7—C12—C111.5 (6)C11—C10—O3—C18−7.8 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.822.002.812 (3)169
Symmetry codes: (i) −x, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.822.002.812 (3)169
Symmetry codes: (i) −x, y+1/2, −z+3/2.
references
References top

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