(Z)-Methyl 3-(2,4-dichloro­phen­yl)-3-hy­droxy­acrylate

Xu, L.-X.; Bai, X.-G.; Wang, J.-X.; Wang, Y.-C.

doi:10.1107/S1600536811051014

Volume 68
Part 1
Page o4
January 2012

Received 9 November 2011
Accepted 28 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.034
wR = 0.086
Data-to-parameter ratio = 17.1
Details

(Z)-Methyl 3-(2,4-dichlorophenyl)-3-hydroxyacrylate

Le-Xing Xu,^a Xiao-Guang Bai,^a Ju-Xian Wang ^a and Yu-Cheng Wang ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China
Correspondence e-mail: hongzhaoupr@yahoo.com

The molecular structure of the title compound, C₁₀H₈Cl₂O₃, exists in a cis-enol form, which is stabilized by a strong intramolecular O-HO hydrogen bond. In the crystal, C-HO interactions generate zigzag chains along the c axis which are, in turn, linked by further C-HO interactions into sheets parallel to (100).

Related literature

For the synthesis of the title compound, see: Wu et al. (1997). For related structures, see: Mei & Huang (2007); Zheng, Fan et al. (2007); Zheng, Zheng et al. (2007). For the coordination properties of similar compounds, see: Nakamoto et al. (1970); Ma et al. (1999); Yoshida et al.(2005).

Experimental

Crystal data

C₁₀H₈Cl₂O₃
M_r = 247.06
Monoclinic, C c
a = 15.889 (3) Å
b = 3.8242 (8) Å
c = 18.204 (4) Å
= 108.18 (3)°
V = 1050.9 (4) Å³
Z = 4
Mo K radiation
= 0.60 mm^-1
T = 294 K
0.25 × 0.20 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer
5011 measured reflections
2371 independent reflections
2170 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.086
S = 1.07
2371 reflections
139 parameters
2 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.18 e Å^-3
Absolute structure: Flack (1983), 1177 Friedel pairs
Flack parameter: 0.07 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.82	1.87	2.592 (3)	146
C3-H3O2ⁱ	0.93	2.48	3.356 (3)	157
C10-H10BO1ⁱⁱ	0.96	2.57	3.492 (3)	162
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2037 ).

Acknowledgements

This work was supported by the National Natural Science Foundation (81072577).

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Ma, Y. L., Reardon, D., Gambarotta, S. & Yap, G. (1999). Organometallics, 18, 2773-2781.
Mei, G.-Q. & Huang, K.-L. (2007). Acta Cryst. E63, o1439-o1440.
Nakamoto, K., Udovich, C. & Takemoto, J. (1970). J. Am. Chem. Soc. 92, 3973-3976.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wu, A.-X., Zhao, Y.-R., Qin, B.-C. & Pan, X.-H. (1997). Chin. Sci. Bull. 42, 617-619.
Yoshida, J., Sato, H., Yamagishi, A. & Hoshino, N. (2005). J. Am. Chem. Soc. 127, 8453-8456.
Zheng, C.-Y., Fan, L. & Wang, D. (2007). Acta Cryst. E63, o966-o967.
Zheng, C.-Y., Zheng, J. & Wang, D.-J. (2007). Acta Cryst. E63, o3633.

organic compounds