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

Jin Hou

doi:10.1107/S160053680803571X

. 2008 Nov 8;64(Pt 12):o2293. doi: 10.1107/S160053680803571X

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

Jin Hou ^a,^*

PMCID: PMC2959932 PMID: 21581271

Abstract

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,
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[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 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

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.

Supplementary Material

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

e-64-o2293-sup1.cif^{(18.6KB, cif)}

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

e-64-o2293-Isup2.hkl^{(89.7KB, hkl)}

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

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

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

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).

Experimental

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.