Bis[(diamino­methyl­idene)aza­nium] 5-(1-oxido-1H-1,2,3,4-tetra­zol-5-yl)-1H-1,2,3,4-tetra­zol-1-olate

Fan, R.; Li, P.; Ng, S.W.

doi:10.1107/S1600536812014456

Volume 68
Part 5
Page o1376
May 2012

Received 2 April 2012
Accepted 3 April 2012
Online 13 April 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.107
Data-to-parameter ratio = 11.5
Details

Bis[(diaminomethylidene)azanium] 5-(1-oxido-1H-1,2,3,4-tetrazol-5-yl)-1H-1,2,3,4-tetrazol-1-olate

Rong Fan,^a Ping Li ^b and Seik Weng Ng ^c,^d ^*

^aShanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China,^bJining Teachers College, Department of Chemistry, Wulanchabu 012000, Inner Mongolia, 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

The anion of the title salt, 2[C(NH₂)₃]⁺·C₂N₈O₂^2-, lies on a center of inversion and its two five-membered rings are coplanar. The guanidinium cation forms N-HO and N-HN hydrogen bonds to the anion, generating an eight-membered ring. Other hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For the synthesis of 1,1'-dihydroxy-5,5'-bistetrazole, see: Tselinskii et al. (2001).

Experimental

Crystal data

2CH₆N₃⁺·C₂N₈O₂^2-
M_r = 288.28
Monoclinic, P 2₁ /c
a = 3.6477 (3) Å
b = 16.9661 (12) Å
c = 9.5465 (7) Å
= 97.465 (1)°
V = 585.80 (8) Å³
Z = 2
Mo K radiation
= 0.13 mm^-1
T = 293 K
0.12 × 0.11 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
3402 measured reflections
1328 independent reflections
1229 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.107
S = 1.02
1328 reflections
115 parameters
6 restraints
All H-atom parameters refined
_max = 0.24 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N5-H1O1	0.89 (1)	1.94 (1)	2.821 (2)	173 (2)
N5-H2N3ⁱ	0.88 (1)	2.40 (1)	3.196 (2)	152 (2)
N6-H3N3ⁱ	0.88 (1)	2.34 (1)	3.126 (2)	149 (2)
N6-H4N4ⁱⁱ	0.88 (1)	2.12 (1)	2.975 (2)	164 (2)
N7-H5O1ⁱⁱⁱ	0.87 (1)	1.97 (1)	2.754 (2)	150 (2)
N7-H6N2	0.88 (1)	2.23 (1)	3.104 (2)	177 (2)
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5870 ).

Acknowledgements

We acknowledge the Scientific Research Project of Higher Education of Inner Mongolia (grant No. NJ09204) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tselinskii, I. V., Mel'nikova, S. F. & Romanova, T. V. (2001). Russ. J. Org. Chem. (Engl. Transl.), 37, 455-461.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds