Bis[(1-methyl-1H-tetra­zol-5-yl)sulfan­yl]ethane

Li, C.-R.; Chen, T.; Xia, Z.-Q.

doi:10.1107/S1600536811021957

Volume 67
Part 7
Page o1669
July 2011

Received 21 May 2011
Accepted 7 June 2011
Online 18 June 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 13.4
Details

Bis[(1-methyl-1H-tetrazol-5-yl)sulfanyl]ethane

Chun-Rong Li,^a Tao Chen ^a and Zheng-Qiang Xia ^b ^*

^aSchool of Environmental Science & Engineering, Chang'an University, Xi'an 710054, Shaanxi, People's Republic of China, and ^bCollege of Chemistry and Materials Science, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China
Correspondence e-mail: northwindy@126.com

The title compound, C₆H₁₀N₈S₂, was prepared by the nucleophilic substitution reaction of 5-mercapto-1-methyltetrazole and dichloroethane. In the crystal, the molecule possesses an approximate non-crystallographic twofold symmetry axis. The crystal packing is stabilized by weak intermolecular C-HN and [pi] - [pi] interactions [centroid-centroid distances = 3.448 (6), 3.5085 (5) and 3.4591 (2) Å]. The two five-membered rings form a dihedral angle of 1.9 (2)°.

Related literature

For the synthesis and structures of closely related compounds, see: She et al. (2006); Wei et al. (2011). For the pharmacological activity of tetrazole-containing compounds, see: Gilchrist (1992); Armour et al. (1996); Upadhayaya et al. (2004). For applications of tetrazole derivatives in coordination chemistry and as energetic materials, see: Zhao et al. (2008); Wang et al. (2009).

Experimental

Crystal data

C₆H₁₀N₈S₂
M_r = 258.34
Triclinic, $[P \overline 1]$
a = 7.5905 (17) Å
b = 7.9958 (17) Å
c = 10.398 (2) Å
= 95.206 (3)°
= 92.922 (3)°
= 115.109 (2)°
V = 566.3 (2) Å³
Z = 2
Mo K radiation
= 0.46 mm^-1
T = 296 K
0.31 × 0.27 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.868, T_max = 0.982
2874 measured reflections
1972 independent reflections
1454 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.135
S = 1.39
1972 reflections
147 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1AN4ⁱ	0.96	2.49	3.413 (5)	161
C6-H6BN5ⁱⁱ	0.96	2.43	3.355 (5)	161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+2.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2010 ).

Acknowledgements

We gratefully acknowledge the National Science Foundation of China (No. 20873100) and the Natural Science Foundation of Shaanxi Province (No. FF10091).

References

Armour, D. R., Chung, K. M. L., Congreve, M., Evans, B., Guntrip, S., Hubbard, T., Kay, C., Middlemiss, D., Mordaunt, J. E., Pegg, N. A., Vinader, M. V., Ward, P. & Watson, S. P. (1996). Bioorg. Med. Chem. Lett. 6, 1015-1020.
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gilchrist, T. L. (1992). Heterocyclic Chemistry, 2nd ed., pp. 505-511. New York: John Wiley & Sons.
She, J.-B., Zhang, G.-F., Dou, Y.-L., Fan, X.-Z. & Li, J.-Z. (2006). Acta Cryst. E62, o402-o404.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Upadhayaya, R. S., Jain, S., Sinha, N., Kishore, N., Chandra, R. & Arora, S. K. (2004). Eur. J. Med. Chem. 39, 579-592.
Wang, W. T., Chen, S. P. & Gao, S. L. (2009). Eur. J. Inorg. Chem. 23, 3475-3480.
Wei, W., Xia, Z., Chen, S. & Gao, S. (2011). Acta Cryst. E67, o999.
Zhao, H., Qu, Z. R., Ye, H. Y. & Xiong, R. G. (2008). Chem. Soc. Rev. 37, 84-100.

organic compounds