8-Thia-1,6-diaza­bicyclo­[4.3.0]nonane-7,9-dione

Xi, B.; Shi, L.; Huang, H.; Wang, Q.; Zhu, H.-J.

doi:10.1107/S1600536811038785

Volume 67
Part 10
Page o2771
October 2011

Received 24 July 2011
Accepted 21 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 14.0
Details

8-Thia-1,6-diazabicyclo[4.3.0]nonane-7,9-dione

Bin-bin Xi,^a Lu Shi,^a Hai Huang,^a Qin Wang ^a and Hong-Jun Zhu ^b ^*

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

There are two independent molecules, A and B, in the asymmetric unit of the title compound, C₆H₈N₂O₂S. In the crystal, pairs of intermolecular SO contacts [3.286 (1) Å] link the B molecules into inversion dimers.

Related literature

For applications of the title compound, see: Yamaguchi et al. (1989). For the synthesis, see: Zhu et al. (2011). For bond-length data, see: Allen et al. (1987). For a review of carbonyl-carbonyl interactions, see: Allen et al. (1998).

Experimental

Crystal data

C₆H₈N₂O₂S
M_r = 172.20
Triclinic, $[P \overline 1]$
a = 7.8400 (16) Å
b = 10.464 (2) Å
c = 10.514 (2) Å
= 63.84 (3)°
= 79.62 (3)°
= 89.42 (3)°
V = 759.2 (3) Å³
Z = 4
Mo K radiation
= 0.37 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.896, T_max = 0.964
3018 measured reflections
2795 independent reflections
2092 reflections with I > 2(I)
R_int = 0.041
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.125
S = 1.00
2795 reflections
200 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.32 e Å^-3

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2196 ).

Acknowledgements

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

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.
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.
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.
Yamaguchi, M., Suzuki, C., Matsunari, K., Miyazawa, T. & Nakamura, Y. (1989). EP Patent 0312064A2.
Zhu, H. J., Xi, B. B., Feng, M. L., Wang, K., Li, Y. F., Shi, L. & Chen, C. (2011). CN Patent Appl. CN 201110091918.8.

organic compounds