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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 [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.086
Data-to-parameter ratio = 17.1
Details
Open access

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

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-H...O hydrogen bond. In the crystal, C-H...O interactions generate zigzag chains along the c axis which are, in turn, linked by further C-H...O interactions into sheets parallel to (100).

Related literature

For the synthesis of the title compound, see: Wu et al. (1997[Wu, A.-X., Zhao, Y.-R., Qin, B.-C. & Pan, X.-H. (1997). Chin. Sci. Bull. 42, 617-619.]). For related structures, see: Mei & Huang (2007[Mei, G.-Q. & Huang, K.-L. (2007). Acta Cryst. E63, o1439-o1440.]); Zheng, Fan et al. (2007[Zheng, C.-Y., Fan, L. & Wang, D. (2007). Acta Cryst. E63, o966-o967.]); Zheng, Zheng et al. (2007[Zheng, C.-Y., Zheng, J. & Wang, D.-J. (2007). Acta Cryst. E63, o3633.]). For the coordination properties of similar compounds, see: Nakamoto et al. (1970[Nakamoto, K., Udovich, C. & Takemoto, J. (1970). J. Am. Chem. Soc. 92, 3973-3976.]); Ma et al. (1999[Ma, Y. L., Reardon, D., Gambarotta, S. & Yap, G. (1999). Organometallics, 18, 2773-2781.]); Yoshida et al.(2005[Yoshida, J., Sato, H., Yamagishi, A. & Hoshino, N. (2005). J. Am. Chem. Soc. 127, 8453-8456.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8Cl2O3

  • Mr = 247.06

  • Monoclinic, C c

  • a = 15.889 (3) Å

  • b = 3.8242 (8) Å

  • c = 18.204 (4) Å

  • [beta] = 108.18 (3)°

  • V = 1050.9 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.086

  • S = 1.07

  • 2371 reflections

  • 139 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1177 Friedel pairs

  • Flack parameter: 0.07 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.82 1.87 2.592 (3) 146
C3-H3...O2i 0.93 2.48 3.356 (3) 157
C10-H10B...O1ii 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [details]
Ma, Y. L., Reardon, D., Gambarotta, S. & Yap, G. (1999). Organometallics, 18, 2773-2781.  [CrossRef] [ChemPort]
Mei, G.-Q. & Huang, K.-L. (2007). Acta Cryst. E63, o1439-o1440.  [CSD] [CrossRef] [details]
Nakamoto, K., Udovich, C. & Takemoto, J. (1970). J. Am. Chem. Soc. 92, 3973-3976.  [CrossRef] [ChemPort] [ISI]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zheng, C.-Y., Fan, L. & Wang, D. (2007). Acta Cryst. E63, o966-o967.  [CSD] [CrossRef] [details]
Zheng, C.-Y., Zheng, J. & Wang, D.-J. (2007). Acta Cryst. E63, o3633.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o4  [ doi:10.1107/S1600536811051014 ]

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