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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 [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 12.2
Details
Open access

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

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-H...O 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[Sen, U., Bozkurt, A. & Ata, A. (2010). J. Power Sources, 195, 7720-7726.]); Subbaraman et al. (2009[Subbaraman, R., Ghassemi, H. & Zawodzinski, T. Jr (2009). Solid State Ionics, 180, 1143-1150.]); Wang & Zhou (2011[Wang, Y. & Zhou, C.-H. (2011). Sci. Sin. Chem. 41, 1429-1456.]); Zhou et al. (2009[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.]); Bai et al. (2007[Bai, X., Zhou, C.-H. & Mi, J.-L. (2007). Chem. Res. Appl. 19, 721-729.]); Chang et al.(2011[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.]).

[Scheme 1]

Experimental

Crystal data
  • C2H4N3+·C7H5Cl2O3S-

  • Mr = 310.15

  • Triclinic, [P \overline 1]

  • a = 5.2430 (6) Å

  • b = 8.2970 (8) Å

  • c = 14.5656 (15) Å

  • [alpha] = 94.330 (5)°

  • [beta] = 98.387 (6)°

  • [gamma] = 92.292 (5)°

  • V = 624.22 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.820, Tmax = 0.846

  • 8971 measured reflections

  • 2196 independent reflections

  • 2000 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.69 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1M...O1i 0.85 (4) 1.96 (4) 2.709 (3) 146 (4)
N3-H4M...O2ii 0.79 (4) 2.08 (4) 2.768 (3) 146 (3)
N3-H4M...O2iii 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[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


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.  [ChemPort]
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.  [ChemPort]
Sen, U., Bozkurt, A. & Ata, A. (2010). J. Power Sources, 195, 7720-7726.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Subbaraman, R., Ghassemi, H. & Zawodzinski, T. Jr (2009). Solid State Ionics, 180, 1143-1150.  [ISI] [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o131  [ doi:10.1107/S1600536811053062 ]

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