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Volume 68 
Part 1 
Page o151  
January 2012  

Received 28 November 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.131
Data-to-parameter ratio = 12.5
Details
Open access

(E)-3,3'-(Diazene-1,2-diyl)bis(1-methyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium) dinitrate dihydrate

aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: zhaohong@seu.edu.cn

The title compound, C12H18N82+·2NO3-·2H2O, was synthesized unexpectedly from 3-amino-1-methyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium chloride and cerium(IV) ammonium nitrate. The cation has a crystallographically imposed centre of symmetry. In the crystal, the ions and water molecules are linked via O-H...N, N-H...O and O-H...O hydrogen bonds into a three-dimensional network.

Related literature

For background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005[Fancelli, D., Berta, D., Bindi, S., Cameron, A., Cappella, P., Carpinelli, P., et al. (2005). J. Med. Chem. 48, 3080-3084.]); Gadekar et al. (1968[Gadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616-618.]). For a related structure, see: Xia et al. (2011[Xia, W.-B., Bai, X.-G., Liu, H.-T. & Wang, J.-X. (2011). Acta Cryst. E67, o1150.]).

[Scheme 1]

Experimental

Crystal data
  • C12H18N82+·2NO3-·2H2O

  • Mr = 434.40

  • Triclinic, [P \overline 1]

  • a = 6.2344 (12) Å

  • b = 7.7725 (16) Å

  • c = 9.7071 (19) Å

  • [alpha] = 99.56 (3)°

  • [beta] = 92.49 (3)°

  • [gamma] = 92.84 (3)°

  • V = 462.64 (16) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 295 K

  • 0.22 × 0.16 × 0.12 mm

Data collection
  • Rigaku SCXmini diffractometer

  • 4322 measured reflections

  • 1811 independent reflections

  • 1479 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.131

  • S = 1.08

  • 1811 reflections

  • 145 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1E...N4i 0.95 (3) 1.98 (3) 2.895 (2) 163 (2)
N2-H2B...O1ii 0.90 1.94 2.802 (3) 159
N2-H2A...O1iii 0.90 2.44 2.970 (2) 118
N2-H2A...O3iv 0.90 2.18 2.894 (3) 136
O1-H1F...O2 0.85 (4) 1.97 (4) 2.819 (2) 173 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+2; (iv) -x+2, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL/PC.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2680 ).


Acknowledgements

This work was supported financially by the Southeast University Fund for Young Researchers (4007041027).

References

Fancelli, D., Berta, D., Bindi, S., Cameron, A., Cappella, P., Carpinelli, P., et al. (2005). J. Med. Chem. 48, 3080-3084.  [ISI] [CrossRef] [PubMed] [ChemPort]
Gadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616-618.  [CrossRef] [ChemPort] [PubMed] [ISI]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xia, W.-B., Bai, X.-G., Liu, H.-T. & Wang, J.-X. (2011). Acta Cryst. E67, o1150.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o151  [ doi:10.1107/S1600536811053347 ]

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