1H-1,2,4-Triazol-4-ium (3,4-dichloro­phen­yl)methane­sulfonate

Zhang, L.; Damu, G.L.V.; Lv, J.-S.; Geng, R.-X.; Zhou, C.-H.

doi:10.1107/S1600536811053062

Volume 68
Part 1
Page o131
January 2012

Received 4 December 2011
Accepted 9 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 12.2
Details

1H-1,2,4-Triazol-4-ium (3,4-dichlorophenyl)methanesulfonate

Ling Zhang,^a Guri L. V. Damu,^a Jing-Song Lv,^a Rong-Xia Geng ^a ^* and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
Correspondence e-mail: geng0712@swu.edu.cn, zhouch@swu.edu.cn

In the title molecular salt, C₂H₄N₃⁺·C₇H₅Cl₂O₃S^-, C-C-S angle [112.25 (18)°] deviates slightly from that expected for ideal sp³-hybridization geometry. In the crystal, the components are linked by N-HO and bifurcated N-H(O,O) hydrogen bonds into chains parallel to [110].

Related literature

For applications of triazole compounds, see: Sen et al. (2010); Subbaraman et al. (2009); Wang & Zhou (2011); Zhou et al. (2009); Bai et al. (2007); Chang et al.(2011).

Experimental

Crystal data

C₂H₄N₃⁺·C₇H₅Cl₂O₃S^-
M_r = 310.15
Triclinic, $[P \overline 1]$
a = 5.2430 (6) Å
b = 8.2970 (8) Å
c = 14.5656 (15) Å
= 94.330 (5)°
= 98.387 (6)°
= 92.292 (5)°
V = 624.22 (11) Å³
Z = 2
Mo K radiation
= 0.69 mm^-1
T = 296 K
0.30 × 0.28 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.820, T_max = 0.846
8971 measured reflections
2196 independent reflections
2000 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.124
S = 1.03
2196 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.69 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1MO1ⁱ	0.85 (4)	1.96 (4)	2.709 (3)	146 (4)
N3-H4MO2ⁱⁱ	0.79 (4)	2.08 (4)	2.768 (3)	146 (3)
N3-H4MO2ⁱⁱⁱ	0.79 (4)	2.54 (3)	3.089 (3)	128 (3)
Symmetry codes: (i) x, y+1, z; (ii) x-1, y, z; (iii) -x, -y, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: LH5392 ).

Acknowledgements

This work was partially supported by the Natural Science Foundation of China (21172181), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Fundamental Research Funds for the Central Universities (XDJK2011D007).

References

Bai, X., Zhou, C.-H. & Mi, J.-L. (2007). Chem. Res. Appl. 19, 721-729.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chang, J.-J., Wang, Y., Zhang, H.-Z., Zhou, C.-H., Geng, R.-X. & Ji, Q.-G. (2011). Chem. J. Chin. Univ. 32, 1970-1985.
Sen, U., Bozkurt, A. & Ata, A. (2010). J. Power Sources, 195, 7720-7726.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Subbaraman, R., Ghassemi, H. & Zawodzinski, T. Jr (2009). Solid State Ionics, 180, 1143-1150.
Wang, Y. & Zhou, C.-H. (2011). Sci. Sin. Chem. 41, 1429-1456.
Zhou, C.-H., Gan, L.-L., Zhang, Y.-Y., Zhang, F.-F., Wang, G.-Z., Jin, L. & Geng, R. X. (2009). Sci. China Ser. B, 52, 415-458.

organic compounds