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Volume 69 
Part 7 
Page o1086  
July 2013  

Received 7 May 2013
Accepted 5 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](N-C) = 0.003 Å
R = 0.044
wR = 0.116
Data-to-parameter ratio = 11.5
Details
Open access

Carbamoyl(diaminomethylidene)azanium 3-nitro-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-ide

aXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China,bDepartment of Mathematics, Jining Teachers College, Wulanchabu 012000, People's Republic of China,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

In the anion of the title salt, C2H7N4O+·C2HN4O3-, the negative charge resides formally on the N3 atom of the triazole ring. In the crystal, the N3 and exocyclic O atoms are hydrogen-bond acceptors with respect to the formally double-bond iminium and amido N atoms of the cation. The cation and anion are almost planar (r.m.s. deviations = 0.012 and 0.051 Å, respectively), but they are slightly bent with respect to each other [dihedral angle = 12.6 (1)°]. In the crystal, adjacent anions and cations are linked by extensive N-H...N and N-H...O hydrogen bonds, generating a ribbon running along the b-axis direction.

Related literature

For background to applications of similar compounds as propellants and explosives, see: Liu et al. (2006[Liu, Q., Wang, B.-Z., Zhang, Z.-Z., Zhu, Z.-H. & Lian, P. (2006). Chin. J. Explosives Propellants, 29, 29-31.]); Östmark et al. (2002[Östmark, H., Bemm, U., Bergman, H. & Langlet, A. (2002). Thermochim. Acta, 384, 253-259.]).

[Scheme 1]

Experimental

Crystal data
  • C2H7N4O+·C2HN4O3-

  • Mr = 232.18

  • Monoclinic, P 21 /n

  • a = 3.7100 (5) Å

  • b = 13.4195 (19) Å

  • c = 18.033 (3) Å

  • [beta] = 94.143 (3)°

  • V = 895.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • 5217 measured reflections

  • 2032 independent reflections

  • 1297 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.00

  • 2032 reflections

  • 177 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O4i 0.87 (2) 1.97 (2) 2.819 (2) 166 (2)
N5-H2...N3 0.94 (2) 1.99 (3) 2.926 (3) 173 (2)
N5-H3...O1ii 0.90 (3) 2.13 (3) 3.005 (2) 164 (2)
N6-H4...O1 0.89 (2) 1.96 (2) 2.824 (2) 163 (2)
N8-H5...O1 0.95 (3) 2.15 (3) 2.966 (3) 142 (2)
N8-H6...O3iii 0.87 (2) 2.32 (3) 3.183 (3) 173 (2)
N7-H7...N2iii 0.90 (2) 2.03 (3) 2.913 (2) 166 (2)
N7-H8...O4 0.85 (2) 2.02 (2) 2.645 (2) 129 (2)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5702 ).


Acknowledgements

We thank the Scientific Research Project of Higher Education of Inner Mongolia (No. NJZY13284 and No. NJZC13283), the Inner Mongolia Science & Technology Plan and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR-MOHE/SC/03) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Liu, Q., Wang, B.-Z., Zhang, Z.-Z., Zhu, Z.-H. & Lian, P. (2006). Chin. J. Explosives Propellants, 29, 29-31.
Östmark, H., Bemm, U., Bergman, H. & Langlet, A. (2002). Thermochim. Acta, 384, 253-259.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1086  [ doi:10.1107/S1600536813015699 ]

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