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

Wu Chen; Yong-Ming Cui; Fei Pan; Dong-Sheng Xia; Qing-Fu Zeng

doi:10.1107/S1600536808036945

. 2008 Nov 20;64(Pt 12):o2374. doi: 10.1107/S1600536808036945

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

Wu Chen ^a, Yong-Ming Cui ^a, Fei Pan ^a, Dong-Sheng Xia ^a, Qing-Fu Zeng ^a,^*

PMCID: PMC2960068 PMID: 21581346

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 ▶). For the properties of phenylacetate and styrene derivatives, see: Huang et al. (2007 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

C₁₈H₁₆F₂O₄
M _r = 334.31
Monoclinic,
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 ▶) 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
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.31 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/S1600536808036945/cv2469sup1.cif

e-64-o2374-sup1.cif^{(19.7KB, cif)}

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

e-64-o2374-Isup2.hkl^{(156.9KB, 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
C6—H6⋯O1ⁱ	0.93	2.52	3.280 (2)	140

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Symmetry code: (i) Inline graphic .

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.