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

Hou, J.

doi:10.1107/S160053680803571X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2293

doi:10.1107/S160053680803571X

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

Jin Hou ^a ^*

^aDepartment of Chemistry and Chemical Engineering, South-East University, Nanjing 211189, and Nantong Entry-Exit Inspection and Quarantine Bureau, Nantong 226005, People's Republic of China
^*Correspondence e-mail: jinhou_jinhou@yahoo.com.cn

(Received 19 October 2008; accepted 31 October 2008; online 8 November 2008)

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.

Related literature

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

Crystal data

C₁₈H₁₈O₅
M_r = 314.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4773 (16) Å
b = 11.661 (2) Å
c = 18.417 (4) Å
V = 1605.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.963, T_max = 0.981
5527 measured reflections
1822 independent reflections
1486 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.134
S = 1.05
1822 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1ⁱ	0.82	2.00	2.812 (3)	169
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803571X/ci2693sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803571X/ci2693Isup2.hkl

checkCIF report

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.

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

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

C₁₈H₁₈O₅	F(000) = 664
M_r = 314.33	D_x = 1.304 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1213 reflections
a = 7.4773 (16) Å	θ = 3.2–26.1°
b = 11.661 (2) Å	µ = 0.10 mm⁻¹
c = 18.417 (4) Å	T = 298 K
V = 1605.8 (6) Å³	Prism, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1822 independent reflections
Radiation source: fine-focus sealed tube	1486 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.963, T_max = 0.981	k = −10→14
5527 measured reflections	l = −22→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0689P)² + 0.4887P] where P = (F_o² + 2F_c²)/3
1822 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₈H₁₈O₅	V = 1605.8 (6) Å³
M_r = 314.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4773 (16) Å	µ = 0.10 mm⁻¹
b = 11.661 (2) Å	T = 298 K
c = 18.417 (4) Å	0.40 × 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)
T_min = 0.963, T_max = 0.981	R_int = 0.032
5527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
1822 reflections	Δρ_min = −0.34 e Å⁻³
211 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.0040 (5)	0.4964 (3)	0.73124 (16)	0.0401 (8)
C2	0.0773 (6)	0.4306 (3)	0.78656 (17)	0.0485 (9)
H2	0.1463	0.3669	0.7750	0.058*
C3	0.0490 (6)	0.4589 (3)	0.85909 (18)	0.0489 (10)
H3	0.0990	0.4144	0.8957	0.059*
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	−0.2019	0.6810	0.8335	0.054*
C6	−0.1024 (5)	0.5887 (3)	0.74921 (17)	0.0471 (9)
H6	−0.1556	0.6319	0.7126	0.057*
C7	0.0419 (5)	0.6087 (3)	0.47594 (16)	0.0370 (7)
C8	−0.0503 (5)	0.5959 (3)	0.41071 (17)	0.0407 (8)
H8	−0.0970	0.5246	0.3984	0.049*
C9	−0.0734 (5)	0.6872 (3)	0.36402 (17)	0.0462 (9)
H9	−0.1336	0.6762	0.3204	0.055*
C10	−0.0083 (5)	0.7946 (3)	0.38124 (18)	0.0441 (9)
C11	0.0842 (5)	0.8107 (3)	0.44550 (19)	0.0463 (9)
H11	0.1287	0.8826	0.4578	0.056*
C12	0.1095 (5)	0.7176 (3)	0.49137 (19)	0.0440 (9)
H12	0.1741	0.7282	0.5340	0.053*
C13	0.0301 (5)	0.5385 (3)	0.60130 (17)	0.0415 (8)
H13	0.0000	0.6138	0.6123	0.050*
C14	0.0590 (5)	0.5141 (3)	0.52943 (17)	0.0394 (8)
C15	0.1049 (5)	0.3973 (3)	0.50927 (17)	0.0397 (8)
C16	0.1644 (7)	0.2682 (3)	0.41167 (18)	0.0513 (10)
H16A	0.0775	0.2121	0.4281	0.062*
H16B	0.2814	0.2462	0.4297	0.062*
C17	0.1658 (6)	0.2743 (3)	0.33027 (17)	0.0549 (10)
H17A	0.0455	0.2826	0.3128	0.082*
H17B	0.2170	0.2053	0.3109	0.082*
H17C	0.2357	0.3390	0.3150	0.082*
C18	−0.0024 (7)	0.9941 (3)	0.3518 (3)	0.0668 (13)
H18A	−0.0656	1.0139	0.3954	0.100*
H18B	−0.0374	1.0450	0.3134	0.100*
H18C	0.1239	1.0008	0.3600	0.100*
O5	0.0407 (4)	0.4650 (3)	0.65807 (14)	0.0662 (8)
O1	0.1315 (4)	0.3188 (2)	0.55214 (12)	0.0541 (7)
O2	0.1174 (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	−0.1019	0.6483	0.9520	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.047 (2)	0.0446 (17)	0.0288 (16)	−0.0058 (17)	−0.0002 (15)	−0.0054 (14)
C2	0.062 (2)	0.0465 (19)	0.0373 (17)	−0.003 (2)	0.0026 (18)	−0.0020 (15)
C3	0.071 (3)	0.0439 (18)	0.0320 (16)	−0.008 (2)	−0.0065 (18)	0.0043 (15)
C4	0.060 (2)	0.0450 (19)	0.0281 (15)	−0.011 (2)	0.0040 (16)	−0.0038 (14)
C5	0.053 (2)	0.0458 (19)	0.0379 (18)	0.0008 (19)	0.0010 (17)	−0.0091 (16)
C6	0.054 (2)	0.056 (2)	0.0313 (16)	0.002 (2)	−0.0039 (16)	0.0043 (16)
C7	0.0403 (17)	0.0406 (17)	0.0302 (15)	−0.0005 (17)	0.0009 (15)	−0.0029 (14)
C8	0.046 (2)	0.0405 (18)	0.0352 (17)	−0.0062 (17)	−0.0021 (16)	−0.0060 (14)
C9	0.058 (2)	0.052 (2)	0.0282 (15)	−0.004 (2)	−0.0067 (16)	−0.0010 (15)
C10	0.048 (2)	0.0461 (19)	0.0376 (18)	−0.0014 (18)	0.0041 (17)	−0.0001 (15)
C11	0.053 (2)	0.0395 (17)	0.0464 (19)	−0.0077 (18)	0.0007 (18)	−0.0043 (16)
C12	0.045 (2)	0.049 (2)	0.0385 (18)	−0.0055 (18)	−0.0048 (17)	−0.0065 (16)
C13	0.048 (2)	0.0437 (18)	0.0329 (16)	0.0006 (18)	−0.0030 (15)	−0.0030 (15)
C14	0.0419 (19)	0.0441 (18)	0.0321 (16)	−0.0035 (17)	−0.0041 (16)	−0.0026 (14)
C15	0.048 (2)	0.0404 (17)	0.0303 (16)	−0.0023 (18)	0.0012 (16)	−0.0017 (14)
C16	0.081 (3)	0.0400 (19)	0.0332 (17)	0.001 (2)	0.002 (2)	−0.0028 (15)
C17	0.075 (3)	0.055 (2)	0.0348 (18)	−0.005 (2)	0.0052 (19)	−0.0094 (17)
C18	0.068 (3)	0.047 (2)	0.086 (3)	0.000 (2)	0.000 (3)	0.014 (2)
O5	0.080 (2)	0.0751 (18)	0.0436 (14)	0.0007 (19)	0.0009 (15)	−0.0010 (14)
O1	0.087 (2)	0.0428 (13)	0.0328 (12)	0.0010 (15)	0.0023 (14)	0.0029 (11)
O2	0.0716 (17)	0.0392 (12)	0.0296 (11)	0.0028 (13)	0.0012 (13)	−0.0037 (10)
O3	0.092 (2)	0.0451 (14)	0.0488 (14)	−0.0026 (16)	−0.0042 (16)	0.0095 (12)
O4	0.098 (2)	0.0527 (15)	0.0292 (12)	−0.0039 (18)	0.0073 (14)	−0.0048 (11)

Geometric parameters (Å, º) top

C1—C6	1.379 (5)	C11—C12	1.388 (5)
C1—C2	1.388 (5)	C11—H11	0.93
C1—O5	1.423 (4)	C12—H12	0.93
C2—C3	1.392 (5)	C13—O5	1.354 (4)
C2—H2	0.93	C13—C14	1.371 (4)
C3—C4	1.386 (5)	C13—H13	0.93
C3—H3	0.93	C14—C15	1.454 (4)
C4—O4	1.366 (4)	C15—O1	1.225 (4)
C4—C5	1.377 (5)	C15—O2	1.336 (4)
C5—C6	1.399 (5)	C16—O2	1.444 (4)
C5—H5	0.93	C16—C17	1.501 (5)
C6—H6	0.93	C16—H16A	0.97
C7—C8	1.393 (5)	C16—H16B	0.97
C7—C12	1.396 (4)	C17—H17A	0.96
C7—C14	1.484 (4)	C17—H17B	0.96
C8—C9	1.379 (5)	C17—H17C	0.96
C8—H8	0.93	C18—O3	1.420 (5)
C9—C10	1.381 (5)	C18—H18A	0.96
C9—H9	0.93	C18—H18B	0.96
C10—O3	1.369 (4)	C18—H18C	0.96
C10—C11	1.384 (5)	O4—H4	0.82

C6—C1—C2	118.9 (3)	C11—C12—H12	118.7
C6—C1—O5	122.7 (3)	C7—C12—H12	118.7
C2—C1—O5	118.5 (3)	O5—C13—C14	127.3 (3)
C1—C2—C3	120.9 (4)	O5—C13—H13	116.4
C1—C2—H2	119.6	C14—C13—H13	116.4
C3—C2—H2	119.6	C13—C14—C15	118.5 (3)
C4—C3—C2	119.6 (3)	C13—C14—C7	118.3 (3)
C4—C3—H3	120.2	C15—C14—C7	123.2 (3)
C2—C3—H3	120.2	O1—C15—O2	121.3 (3)
O4—C4—C5	122.1 (3)	O1—C15—C14	125.0 (3)
O4—C4—C3	117.9 (3)	O2—C15—C14	113.7 (3)
C5—C4—C3	120.0 (3)	O2—C16—C17	106.8 (3)
C4—C5—C6	120.0 (3)	O2—C16—H16A	110.4
C4—C5—H5	120.0	C17—C16—H16A	110.4
C6—C5—H5	120.0	O2—C16—H16B	110.4
C1—C6—C5	120.6 (3)	C17—C16—H16B	110.4
C1—C6—H6	119.7	H16A—C16—H16B	108.6
C5—C6—H6	119.7	C16—C17—H17A	109.5
C8—C7—C12	116.9 (3)	C16—C17—H17B	109.5
C8—C7—C14	122.3 (3)	H17A—C17—H17B	109.5
C12—C7—C14	120.7 (3)	C16—C17—H17C	109.5
C9—C8—C7	121.1 (3)	H17A—C17—H17C	109.5
C9—C8—H8	119.4	H17B—C17—H17C	109.5
C7—C8—H8	119.4	O3—C18—H18A	109.5
C8—C9—C10	120.9 (3)	O3—C18—H18B	109.5
C8—C9—H9	119.6	H18A—C18—H18B	109.5
C10—C9—H9	119.6	O3—C18—H18C	109.5
O3—C10—C9	115.8 (3)	H18A—C18—H18C	109.5
O3—C10—C11	124.5 (3)	H18B—C18—H18C	109.5
C9—C10—C11	119.7 (3)	C13—O5—C1	123.8 (3)
C10—C11—C12	118.9 (3)	C15—O2—C16	118.3 (3)
C10—C11—H11	120.6	C10—O3—C18	117.8 (3)
C12—C11—H11	120.6	C4—O4—H4	109.5
C11—C12—C7	122.5 (3)

C6—C1—C2—C3	−1.9 (6)	C14—C7—C12—C11	−174.8 (3)
O5—C1—C2—C3	178.6 (3)	O5—C13—C14—C15	0.5 (6)
C1—C2—C3—C4	0.2 (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—C5	1.2 (6)	C12—C7—C14—C13	41.3 (5)
O4—C4—C5—C6	178.7 (4)	C8—C7—C14—C15	45.3 (5)
C3—C4—C5—C6	−1.0 (6)	C12—C7—C14—C15	−138.6 (4)
C2—C1—C6—C5	2.2 (6)	C13—C14—C15—O1	−4.9 (6)
O5—C1—C6—C5	−178.4 (3)	C7—C14—C15—O1	175.0 (4)
C4—C5—C6—C1	−0.7 (6)	C13—C14—C15—O2	175.4 (3)
C12—C7—C8—C9	−0.2 (5)	C7—C14—C15—O2	−4.7 (5)
C14—C7—C8—C9	176.0 (3)	C14—C13—O5—C1	−178.3 (4)
C7—C8—C9—C10	−1.1 (6)	C6—C1—O5—C13	23.2 (6)
C8—C9—C10—O3	−178.0 (4)	C2—C1—O5—C13	−157.3 (4)
C8—C9—C10—C11	1.2 (6)	O1—C15—O2—C16	−0.4 (6)
O3—C10—C11—C12	179.1 (4)	C14—C15—O2—C16	179.3 (3)
C9—C10—C11—C12	0.0 (6)	C17—C16—O2—C15	179.1 (3)
C10—C11—C12—C7	−1.4 (6)	C9—C10—O3—C18	171.3 (4)
C8—C7—C12—C11	1.5 (6)	C11—C10—O3—C18	−7.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.82	2.00	2.812 (3)	169

Symmetry code: (i) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₅
M_r	314.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.4773 (16), 11.661 (2), 18.417 (4)
V (Å³)	1605.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.963, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	5527, 1822, 1486
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.134, 1.05
No. of reflections	1822
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.34

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.82	2.00	2.812 (3)	169

Symmetry code: (i) −x, y+1/2, −z+3/2.

References

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. CrossRef Web of Science Google Scholar
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Volume 64| Part 12| December 2008| Page o2293

doi:10.1107/S160053680803571X

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