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Volume 69 
Part 3 
Pages o353-o354  
March 2013  

Received 25 January 2013
Accepted 31 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.040
wR = 0.108
Data-to-parameter ratio = 20.1
Details
Open access

Bis(3,5-diamino-4H-1,2,4-triazol-1-ium) 3,4-dioxocyclobutane-1,2-diolate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia,cH. E. J Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75720, Pakistan, and dDepartment of Pure and Applied Chemistry, University of Calabar, P. M. B. 1115, Calabar, Nigeria
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, 2C2H6N5+·C4O42-, contains two 3,5-diamino-4H-1,2,4-triazolium cations and one squarate dianion. The squaric acid molecule donated one H atom to each of the two 3,5-diamino-1,2,4-triazole molecules at their N atoms. The squaric acid dianion has four C-O bonds which are shorter than a normal single C-O bond (1.426 Å) and are slightly longer than a normal C=O bond (1.23 Å), which indicates the degree of electron delocalization in the dianion. In the crystal, the cations and dianions are linked by N-H...N and N-H...O hydrogen bonds into a three-dimensional network.

Related literature

For background to the acid-base chemistry of squarate acid, see: Mathew et al. (2002[Mathew, S., Paul, G., Shivasankar, K., Choudhury, A. & Rao, C. N. R. (2002). J. Mol. Struct. 641, 263-279.]); Frankenbach et al. (1992[Frankenbach, G. M., Beno, M. A., Kini, A. M., Williams, J. M., Welp, U., Thompson, J. E. & Whangbo, M. H. (1992). Inorg. Chim. Acta, 192, 195-200.]); Yesilel et al. (2008[Yesilel, O. Z., Odabasoglu, M. & Büyükgüngör, O. (2008). J. Mol. Struct. 874, 151-158.]); Bertolasi et al. (2001[Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (2001). Acta Cryst. B57, 591-598.]); Correa et al. (2007[Correa, C. C., Diniz, R., Chagas, L. H., Rodrigues, B. L., Yoshida, M. I., Teles, W. M., Machado, F. C. & de Oliveira, L. F. C. (2007). Polyhedron, 26, 989-995.]). For a related structure, see: Uçar et al. (2004[Uçar, I., Bulut, A., Yesilel, O. Z. & Büyükgüngör, O. (2004). Acta Cryst. C60, o585-o588.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • 2C2H6N5+·C4O42-

  • Mr = 312.28

  • Monoclinic, P 21 /c

  • a = 15.7186 (2) Å

  • b = 11.6533 (2) Å

  • c = 6.8618 (1) Å

  • [beta] = 91.734 (1)°

  • V = 1256.32 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 100 K

  • 0.44 × 0.20 × 0.14 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX22, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.943, Tmax = 0.982

  • 19113 measured reflections

  • 4965 independent reflections

  • 3911 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.108

  • S = 1.03

  • 4965 reflections

  • 247 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1N1...O4i 0.913 (16) 1.761 (16) 2.6677 (9) 171.3 (15)
N3A-H1N3...O4ii 0.937 (15) 1.746 (15) 2.6734 (10) 170.2 (14)
N4A-H1N4...O3i 0.887 (15) 2.003 (15) 2.8877 (10) 175.2 (13)
N4A-H2N4...N4Biii 0.904 (15) 2.565 (15) 3.3917 (12) 152.3 (12)
N5A-H1N5...N2Aiv 0.933 (15) 2.105 (15) 3.0167 (11) 165.3 (13)
N5A-H2N5...O1ii 0.922 (15) 1.940 (15) 2.8621 (11) 177.7 (14)
N1B-H2N1...O2v 0.874 (15) 1.781 (15) 2.6485 (9) 171.8 (15)
N3B-H2N3...O2 0.965 (15) 1.706 (15) 2.6637 (10) 171.2 (14)
N4B-H3N4...O1v 0.920 (14) 2.065 (14) 2.9564 (10) 162.8 (12)
N4B-H4N4...O1vi 0.867 (13) 2.150 (13) 2.9954 (10) 164.9 (12)
N5B-H3N5...N2Bv 0.923 (15) 2.159 (15) 3.0579 (11) 164.3 (12)
N5B-H4N5...O3 1.001 (16) 1.832 (15) 2.8293 (10) 174.2 (12)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX22, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX22, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5040 ).


Acknowledgements

HKF and WSL thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant (1001/CIPPM813040). WSL also thanks the Malaysian Government and USM for the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AJ thanks the Academy of Science for the Developing World (TWAS) for the award of a Research and Advanced Training Fellowship and the H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Pakistan, for providing research facilities. SY thanks the School of Physics, Universiti Sains Malaysia, for providing X-ray diffraction research facilities.

References

Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (2001). Acta Cryst. B57, 591-598.  [ISI] [CSD] [CrossRef] [ChemPort] [details]
Bruker (2009). APEX22, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Correa, C. C., Diniz, R., Chagas, L. H., Rodrigues, B. L., Yoshida, M. I., Teles, W. M., Machado, F. C. & de Oliveira, L. F. C. (2007). Polyhedron, 26, 989-995.  [ChemPort]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Frankenbach, G. M., Beno, M. A., Kini, A. M., Williams, J. M., Welp, U., Thompson, J. E. & Whangbo, M. H. (1992). Inorg. Chim. Acta, 192, 195-200.  [CrossRef] [ChemPort] [ISI]
Mathew, S., Paul, G., Shivasankar, K., Choudhury, A. & Rao, C. N. R. (2002). J. Mol. Struct. 641, 263-279.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Uçar, I., Bulut, A., Yesilel, O. Z. & Büyükgüngör, O. (2004). Acta Cryst. C60, o585-o588.  [CSD] [CrossRef] [details]
Yesilel, O. Z., Odabasoglu, M. & Büyükgüngör, O. (2008). J. Mol. Struct. 874, 151-158.


Acta Cryst (2013). E69, o353-o354   [ doi:10.1107/S160053681300322X ]

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