(E)-2,3-Bis(4-methoxy­phen­yl)acrylic acid

Banfeng Ruan; Ying Yang; Zhenwei Zhu; Pengcheng Lv; Hailiang Zhu

doi:10.1107/S1600536809011751

. 2009 Apr 2;65(Pt 5):o944. doi: 10.1107/S1600536809011751

(E)-2,3-Bis(4-methoxyphenyl)acrylic acid

Banfeng Ruan ^a, Ying Yang ^a, Zhenwei Zhu ^a, Pengcheng Lv ^a, Hailiang Zhu ^a,^*

PMCID: PMC2977645 PMID: 21583988

Abstract

In the title molecule, C₁₇H₁₆O₄, the angle between the aromatic ring planes is 69.1 (6)°. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds; molecules related by a centre of symmetry are linked to form inversion dimers.

Related literature

For the biological properties and synthesis of resveratrol (trans-3,4′,5-trihydroxystilbene) and its derivatives, see: Huang, Ruan et al. (2007 ▶); Huang et al. (2008 ▶); Jang et al. (1997 ▶); Ruan et al. (2006 ▶); Schulze et al. (2005 ▶); Shi et al. (2005 ▶). For related crystal structures, see: Huang, Li et al. (2007 ▶); Stomberg et al. (2001 ▶).

Experimental

Crystal data

C₁₇H₁₆O₄
M _r = 284.30
Triclinic,
a = 5.8690 (12) Å
b = 9.1480 (18) Å
c = 13.992 (3) Å
α = 83.65 (3)°
β = 85.43 (3)°
γ = 80.92 (3)°
V = 735.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.973, T _max = 0.991
3196 measured reflections
2895 independent reflections
1779 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.151
S = 1.08
2895 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011751/wn2320sup1.cif

e-65-0o944-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011751/wn2320Isup2.hkl

e-65-0o944-Isup2.hkl^{(142.1KB, 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
O3—H3⋯O2ⁱ	0.82	1.80	2.608 (2)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was financed by a grant (Project 30772627) from the National Natural Science Foundation of China.

supplementary crystallographic information

Comment

Resveratrol (trans-3, 4',5-trihydroxystilbene) and its derivatives have attracted much attention since it was first isolated in 1939, because of their physiological properties and potential therapeutic values (Schulze et al., 2005; Jang et al., 1997). In our laboratory, we have synthesized two series of resveratrol derivatives (Ruan et al., 2006; Huang et al., 2007). As part of an extensive structure-activity relationship (SAR) study on resveratrol derivatives, another series of analogues of resveratrol has been synthesized. One of them, namely the title compound, was obtained as single crystals and its crystal structure determined to establish its configuration.

The crystal structure demonstrated that it had the E configuration (Fig. 1). All bond lengths are within normal ranges and very similar to those in related crystal structures (Stomberg et al., 2001). The torsion angles C5—C8—C10—C11 and C9—C8—C10—C11 are 5.9 (4)° and -176.6 (2)°, respectively. The angle between the aromatic ring planes is 69.1 (6)°. In the crystal structure, molecules related by a centre of symmetry are linked to form dimers via intermolecular O—H—O hydrogen bonds (Table 1 and Fig. 2).

Experimental

2-(4-Methoxyphenyl)acetic acid (1.66 g, 0.01 mol), 4-methoxybenzaldehyde (1.36 g, 0.01 mol) and acetic anhydride (15 ml) were added to a three-necked flask in an icewater bath with stirring. Triethylamine (5 ml) was added dropwise into this solution and the mixture was allowed to react at 100°C for 12 h. After cooling to room temperature, the mixture was slowly poured into 50 ml 10% NaOH solution, yielding a white precipitate. This was collected by vacuum filtration, washed with a large amount of water and dried in air. Colorless single crystals were obtained after a week upon evaporation of a solution of the reaction product in a mixture of ethyl acetate (10 ml) and petroleum ether (5 ml).