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Volume 69 
Part 7 
Page o1051  
July 2013  

Received 8 May 2013
Accepted 4 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.077
wR = 0.245
Data-to-parameter ratio = 13.9
Details
Open access

2-Methyl-1,2,4-triazolo[4,3-a]pyridin-2-ium tetrafluoroborate

aDepartment of Medicinal Chemistry, Luzhou Medical College, Luzhou, Sichuan, 646000, People's Republic of China
Correspondence e-mail: swei1225@gmail.com, wq_ring@hotmail.com

In the title salt, C7H8N3+·BF4-, the 1,2,4-triazolo[4,3-a]pyridinium cation is planar [maximum deviation of 0.016 (2) Å for all non-H atoms]. The cation and anion constitute a tight ionic pair with an F...N [2.911 (4) Å] intermolecular attractive interaction. The ionic pairs form dimers via stacking interactions between inversion-related cations, the normal distance between the cation planes being 3.376 (5) Å. The dimers are packed in stacks along the a axis and linked via C-H...F hydrogen bond, forming a three-dimensional network.

Related literature

For catalytic applications of triazoliums, see: Fisher et al. (2006[Fisher, C., Smith, S. W., Powell, D. A. & Fu, G. C. (2006). J. Am. Chem. Soc. 128, 1472-1473.]); Enders et al. (2006[Enders, D., Niemeier, O. & Balensiefer, T. (2006). Angew. Chem. Int. Ed. 45, 1463-1467.]); Wurz et al. (2012[Wurz, N. E., Daniliuc, C. G. & Glorius, F. (2012). Chem. Eur. J. 18, 16297-16301.]). For the synthesis of a related compound and for related structures, see: Ma et al. (2008[Ma, Y., Wei, S., Lan, J., Wang, J., Xie, R. & You, J. (2008). J. Org. Chem. 73, 8256-8264.]); Wei et al. (2009[Wei, S., Liu, B., Zhao, D., Wang, Z., Wu, J., Lan, J. & You, J. (2009). Org. Biomol. Chem. 7, 4241-4247.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8N3+·BF4-

  • Mr = 220.97

  • Orthorhombic, P b c a

  • a = 7.1508 (10) Å

  • b = 12.3070 (18) Å

  • c = 21.431 (3) Å

  • V = 1886.0 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.956, Tmax = 0.970

  • 14891 measured reflections

  • 1903 independent reflections

  • 1616 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.245

  • S = 1.05

  • 1903 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.74 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...F4i 0.93 2.18 3.086 (3) 165
C5-H5...F2ii 0.93 2.38 3.169 (4) 143
C6-H6...F1iii 0.93 2.53 3.301 (5) 141
Symmetry codes: (i) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KQ2005 ).


Acknowledgements

The authors are grateful to the Key Program of the Education Department of Sichuan Province (No. 13ZA0232), the Key Project of Luzhou Medical College (No. 2012ZD-01), the Program for New Century Excellent Talents in University (NCET-10-0945), the Key Project of the Chinese Ministry of Education (No. 211160) and the Scientific Fund of Sichuan Province for Outstanding Young Scientists (No. 2009-26-417) for financial support.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Enders, D., Niemeier, O. & Balensiefer, T. (2006). Angew. Chem. Int. Ed. 45, 1463-1467.  [Web of Science] [CrossRef] [ChemPort]
Fisher, C., Smith, S. W., Powell, D. A. & Fu, G. C. (2006). J. Am. Chem. Soc. 128, 1472-1473.  [Web of Science] [PubMed]
Ma, Y., Wei, S., Lan, J., Wang, J., Xie, R. & You, J. (2008). J. Org. Chem. 73, 8256-8264.  [CSD] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wei, S., Liu, B., Zhao, D., Wang, Z., Wu, J., Lan, J. & You, J. (2009). Org. Biomol. Chem. 7, 4241-4247.  [CSD] [CrossRef] [PubMed] [ChemPort]
Wurz, N. E., Daniliuc, C. G. & Glorius, F. (2012). Chem. Eur. J. 18, 16297-16301.  [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1051  [ doi:10.1107/S1600536813015535 ]

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