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

Shen, W.-T.; Yao, C.

doi:10.1107/S1600536809007727

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 (C-C) = 0.006 Å
R = 0.057
wR = 0.172
Data-to-parameter ratio = 13.8
Details

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

Wen-Tong Shen ^a and Cheng Yao ^a ^*

^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-HO and C-HCl 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). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₀ClNO₃S
M_r = 271.71
Monoclinic, P 2₁ /c
a = 5.4830 (11) Å
b = 19.410 (4) Å
c = 11.060 (2) Å
= 95.16 (3)°
V = 1172.3 (4) Å³
Z = 4
Mo K radiation
= 0.50 mm^-1
T = 294 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.907, T_max = 0.952
2363 measured reflections
2132 independent reflections
1460 reflections with I > 2(I)
R_int = 0.044
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.172
S = 1.00
2132 reflections
154 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4AO3	0.97	2.36	2.768 (5)	105
C4-H4BCl	0.97	2.63	3.105 (4)	110

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
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.
Shao, T., Long, Y. D. & Huang, T. B. (2001). Chin. J. Anal. Chem. 29, 74-76.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds