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Volume 65 
Part 4 
Page o716  
April 2009  

Received 27 February 2009
Accepted 3 March 2009
Online 6 March 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.006 Å
R = 0.057
wR = 0.172
Data-to-parameter ratio = 13.8
Details
Open access

Ethyl 2-(4-chloro-2-oxo-2,3-dihydro-1,3-benzothiazol-3-yl)acetate

aCollege of Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: yaocheng@njut.edu.cn

In the molecule of the title compound, C11H10ClNO3S, the benzene and thiazole rings are oriented at a dihedral angle of 1.25 (3)°. Intramolecular C-H...O and C-H...Cl interactions result in the formation of two five-membered rings which both adopt envelope conformations.

Related literature

For a related structure, see: Shao et al. (2001[Shao, T., Long, Y. D. & Huang, T. B. (2001). Chin. J. Anal. Chem. 29, 74-76.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10ClNO3S

  • Mr = 271.71

  • Monoclinic, P 21 /c

  • a = 5.4830 (11) Å

  • b = 19.410 (4) Å

  • c = 11.060 (2) Å

  • [beta] = 95.16 (3)°

  • V = 1172.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 294 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.907, Tmax = 0.952

  • 2363 measured reflections

  • 2132 independent reflections

  • 1460 reflections with I > 2[sigma](I)

  • Rint = 0.044

  • 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.172

  • S = 1.00

  • 2132 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4A...O3 0.97 2.36 2.768 (5) 105
C4-H4B...Cl 0.97 2.63 3.105 (4) 110

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2637 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Shao, T., Long, Y. D. & Huang, T. B. (2001). Chin. J. Anal. Chem. 29, 74-76.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2009). E65, o716  [ doi:10.1107/S1600536809007727 ]

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