2-(2H-Tetra­zol-5-yl)pyridinium chloride

Dai, J.; Wen, X.-C.

doi:10.1107/S1600536808032649

Volume 64
Part 11
Page o2113
November 2008

Received 10 September 2008
Accepted 9 October 2008
Online 15 October 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.148
Data-to-parameter ratio = 14.1
Details

2-(2H-Tetrazol-5-yl)pyridinium chloride

Jing Dai ^a and Xiao-Chun Wen ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: fudavid88@yahoo.com.cn

In the title compound, C₆H₆N₅⁺·Cl^-, the pyridinium and tetrazole rings are essentially coplanar. The pyridine N atoms are protonated. In the crystal structure, molecules are connected via N-HCl, C-HCl, C-HN and N-HN hydrogen bonds into layers that are parallel to the (001) plane. There are two crystallographically independent molecules in the asymmetric unit which are located on mirror planes.

Related literature

For related literature on tetrazole derivatives, see: Dai & Fu (2008); Wang et al. (2005); Wen (2008); Xiong et al. (2002).

Experimental

Crystal data

C₆H₆N₅⁺·Cl^-
M_r = 183.61
Orthorhombic, P b c m
a = 16.375 (3) Å
b = 15.313 (3) Å
c = 6.5176 (13) Å
V = 1634.3 (5) Å³
Z = 8
Mo K radiation
= 0.41 mm^-1
T = 298 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.910, T_max = 0.938
16127 measured reflections
2041 independent reflections
1511 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.148
S = 1.14
2041 reflections
145 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N9-H9ACl2	0.86	2.14	3.001 (3)	177
N10-H10ACl1	0.86	2.33	3.088 (3)	147
N2-H2Cl2	0.86	2.22	3.050 (4)	163
N5-H5ACl1ⁱ	0.86	2.29	3.049 (3)	147
N5-H5AN1	0.86	2.55	2.881 (4)	104
N10-H10AN6	0.86	2.52	2.858 (4)	105
C9-H9Cl2	0.93	2.64	3.545 (4)	165
C3-H3N8ⁱⁱ	0.93	2.60	3.329 (5)	136
C6-H6N6ⁱ	0.93	2.38	3.260 (5)	159
C10-H10Cl1ⁱⁱⁱ	0.93	2.67	3.596 (4)	174
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2115 ).

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

References

Dai, W. & Fu, D.-W. (2008). Acta Cryst. E64, o1444.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, X.-S., Tang, Y.-Z., Huang, X.-F., Qu, Z.-R., Che, C.-M., Chan, C. W. H. & Xiong, R.-G. (2005). Inorg. Chem. 44, 5278-5285.
Wen, X.-C. (2008). Acta Cryst. E64, m768.
Xiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z.-L. (2002). Angew. Chem. Int. Ed. 41, 3800-3803.

organic compounds