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

Chen, J.-M.; Zhao, H.

doi:10.1107/S1600536811053347

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 (C-C) = 0.003 Å
R = 0.048
wR = 0.131
Data-to-parameter ratio = 12.5
Details

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

Jin-Mei Chen ^a and Hong Zhao ^a ^*

^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-HN, N-HO and O-HO hydrogen bonds into a three-dimensional network.

Related literature

For background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005); Gadekar et al. (1968). For a related structure, see: Xia et al. (2011).

Experimental

Crystal data

C₁₂H₁₈N₈²⁺·2NO₃^-·2H₂O
M_r = 434.40
Triclinic, $[P \overline 1]$
a = 6.2344 (12) Å
b = 7.7725 (16) Å
c = 9.7071 (19) Å
= 99.56 (3)°
= 92.49 (3)°
= 92.84 (3)°
V = 462.64 (16) Å³
Z = 1
Mo K radiation
= 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(I)
R_int = 0.034

Refinement

R[F² > 2(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
_max = 0.28 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1EN4ⁱ	0.95 (3)	1.98 (3)	2.895 (2)	163 (2)
N2-H2BO1ⁱⁱ	0.90	1.94	2.802 (3)	159
N2-H2AO1ⁱⁱⁱ	0.90	2.44	2.970 (2)	118
N2-H2AO3^iv	0.90	2.18	2.894 (3)	136
O1-H1FO2	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); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); 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.
Gadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616-618.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xia, W.-B., Bai, X.-G., Liu, H.-T. & Wang, J.-X. (2011). Acta Cryst. E67, o1150.

organic compounds