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

Ruan, B.; Yang, Y.; Zhu, Z.; Lv, P.; Zhu, H.

doi:10.1107/S1600536809011751

Volume 65
Part 5
Page o944
May 2009

Received 25 March 2009
Accepted 30 March 2009
Online 2 April 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.056
wR = 0.151
Data-to-parameter ratio = 14.9
Details

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

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

^aState Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
Correspondence e-mail: zhuhl@nju.edu.cn

In the title molecule, C₁₇H₁₆O₄, the angle between the aromatic ring planes is 69.1 (6)°. The crystal structure is stabilized by intermolecular O-HO 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, $[P \overline 1]$
a = 5.8690 (12) Å
b = 9.1480 (18) Å
c = 13.992 (3) Å
= 83.65 (3)°
= 85.43 (3)°
= 80.92 (3)°
V = 735.8 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.973, T_max = 0.991
3196 measured reflections
2895 independent reflections
1779 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.151
S = 1.08
2895 reflections
194 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O2ⁱ	0.82	1.80	2.608 (2)	169
Symmetry code: (i) -x+3, -y+2, -z+1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: WN2320 ).

Acknowledgements

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

References

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organic compounds