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Volume 69 
Part 8 
Page o1279  
August 2013  

Received 9 July 2013
Accepted 13 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.060
wR = 0.194
Data-to-parameter ratio = 27.4
Details
Open access

5-Amino-1H-1,2,4-triazol-4-ium hydrogen oxalate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and bChemistry Department, Faculty of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia
Correspondence e-mail: essidmanel@voila.fr

In the title salt, C2H5N4+·C2HO4-, the hydrogen oxalate anions form corrugated chains parallel to the c axis, linked by intermolecular O-H...O hydrogen bonds. The 5-amino-1H-1,2,4-triazol-4-ium cations are connected into centrosymmetric clusters via weak C-H...N hydrogen bonds forming nine-membered rings with an R33(9) motif. These clusters are interconnected via anions through N-H...O hydrogen bonds, building a three-dimensional network.

Related literature

For the properties of triazoles, see: Li et al. (2004[Li, W., Wu, Q., Yu, Y., Luo, M., Hu, L., Gu, Y., Niu, F. & Hu, J. (2004). Spectrochim. Acta Part A, 60, 2343-2354.]); Mernari et al. (1998[Mernari, B., Elattari, H., Traisnel, M., Bentiss, F. & Langrenée, M. (1998). Corros. Sci. 40, 391-399.]); Bentiss et al. (1999[Bentiss, F., Langrenée, M., Traisnel, M. & Hornez, J. C. (1999). Corros. Sci. 41, 789-803.]). For graph-set notation of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., David, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Matulková et al. (2007[Matulková, I., Císarová, I., Nemec, P. & Micka, Z. (2007). J. Mol. Struct. 834-836, 328-335.], 2008[Matulková, I., Nemec, I., Teubner, K., Nemec, P. & Micka, Z. (2008). J. Mol. Struct. 873, 46-60.]).

[Scheme 1]

Experimental

Crystal data
  • C2H5N4+·C2HO4-

  • Mr = 174.13

  • Trigonal, [R \overline 3]

  • a = 23.093 (4) Å

  • c = 6.603 (3) Å

  • V = 3049.3 (16) Å3

  • Z = 18

  • Ag K[alpha] radiation

  • [lambda] = 0.56080 Å

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.35 × 0.3 × 0.25 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 3909 measured reflections

  • 3313 independent reflections

  • 1929 reflections with I > 2[sigma](I)

  • Rint = 0.023

  • 2 standard reflections every 120 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.194

  • S = 1.04

  • 3313 reflections

  • 121 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.87 (3) 1.72 (3) 2.5845 (17) 174 (3)
N1-H2...O1ii 0.86 (3) 2.29 (3) 3.087 (2) 155 (2)
N1-H3...O4iii 0.88 (3) 2.06 (3) 2.925 (2) 171 (3)
N2-H4...O4iv 0.86 2.09 2.892 (2) 154
N2-H4...O2iv 0.86 2.28 2.878 (2) 127
N3-H5...O3iii 0.86 1.94 2.7652 (18) 161
C4-H6...N4v 0.93 2.41 3.313 (3) 165
Symmetry codes: (i) [-x+y+{\script{2\over 3}}, -x+{\script{1\over 3}}, z+{\script{1\over 3}}]; (ii) [-x+y+{\script{2\over 3}}, -x+{\script{1\over 3}}, z-{\script{2\over 3}}]; (iii) -x+1, -y, -z; (iv) [x-y-{\script{1\over 3}}, x-{\script{2\over 3}}, -z+{\script{1\over 3}}]; (v) -y, x-y-1, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS86 (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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2640 ).


Acknowledgements

This work was supported by the Tunisian Ministry of HEScR. The authors are grateful to the Deanship of Scientific Research at King Saud University for funding the paper through the Research Group Project No. RGP-VPP-089.

References

Bentiss, F., Langrenée, M., Traisnel, M. & Hornez, J. C. (1999). Corros. Sci. 41, 789-803.  [CrossRef] [ChemPort]
Bernstein, J., David, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Li, W., Wu, Q., Yu, Y., Luo, M., Hu, L., Gu, Y., Niu, F. & Hu, J. (2004). Spectrochim. Acta Part A, 60, 2343-2354.
Matulková, I., Císarová, I., Nemec, P. & Micka, Z. (2007). J. Mol. Struct. 834-836, 328-335.
Matulková, I., Nemec, I., Teubner, K., Nemec, P. & Micka, Z. (2008). J. Mol. Struct. 873, 46-60.
Mernari, B., Elattari, H., Traisnel, M., Bentiss, F. & Langrenée, M. (1998). Corros. Sci. 40, 391-399.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1279  [ doi:10.1107/S1600536813019363 ]

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