Methyl 7-chloro-2-ethyl­sulfanyl-6-fluoro-4-oxo-4H-thio­chromene-3-carboxyl­ate

Li, Y.; Xiao, T.; Liu, D.; Yu, G.

doi:10.1107/S1600536810002667

Volume 66
Part 3
Page o694
March 2010

Received 16 January 2010
Accepted 21 January 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.045
wR = 0.138
Data-to-parameter ratio = 14.0
Details

Methyl 7-chloro-2-ethylsulfanyl-6-fluoro-4-oxo-4H-thiochromene-3-carboxylate

Yang Li,^a Tao Xiao,^a ^* Dong-liang Liu ^a and Guang-yan Yu ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: taoxiao@njut.edu.cn

In the title compound, C₁₃H₁₀ClFO₃S₂, the two-ring system is essentially planar, the mean plane of the benzene ring being inclined at 6.0 (2)° to the plane of the remaining four atoms. The ethylsulfanyl group is almost coplanar with the two rings [dihedral angle = 6.4 (2)°], while the carboxylate group is almost perpendicular to it [dihedral angle = 72.4 (2)°]. In the crystal structure, intermolecular C-HO and C-HF hydrogen bonds link the molecules in a stacked arrangement along the a axis.

Related literature

For related compounds containing a 4H-thiochromen-4-one fragment, see: Adams et al. (1991); Nakazumi et al. (1992); Weiss et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₁₀ClFO₃S₂
M_r = 332.78
Triclinic, $[P \overline 1]$
a = 7.6740 (15) Å
b = 9.3880 (19) Å
c = 10.368 (2) Å
= 85.18 (3)°
= 80.93 (3)°
= 71.24 (3)°
V = 698.0 (2) Å³
Z = 2
Mo K radiation
= 0.59 mm^-1
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.892, T_max = 0.944
2735 measured reflections
2531 independent reflections
1908 reflections with I > 2(I)
R_int = 0.016
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.138
S = 1.00
2531 reflections
181 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AO1ⁱ	0.93	2.60	3.292 (4)	132
C13-H13CFⁱⁱ	0.96	2.52	3.144 (5)	123
Symmetry codes: (i) x+1, y, z; (ii) -x-1, -y+1, -z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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: 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: ZQ2029 ).

Acknowledgements

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

References

Adams, H., Bailey, N. A., Giles, P. R. & Marson, C. M. (1991). Acta Cryst. C47, 1332-1334.
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 (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Nakazumi, H., Watanabe, S. & Kitao, T. (1992). J. Chem. Res. 212, 1616-1641.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Weiss, R., Bess, M., Huber, S. M. & Heinemann, F. W. (2008). J. Am. Chem. Soc. 130, 4610-4617.

organic compounds