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

Jing Dai; Xiao-Chun Wen

doi:10.1107/S1600536808032649

. 2008 Oct 15;64(Pt 11):o2113. doi: 10.1107/S1600536808032649

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

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

PMCID: PMC2959608 PMID: 21580977

Abstract

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—H⋯Cl, C—H⋯Cl, C—H⋯N and N—H⋯N 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,
a = 16.375 (3) Å
b = 15.313 (3) Å
c = 6.5176 (13) Å
V = 1634.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.076

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.148
S = 1.14
2041 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032649/nc2115sup1.cif

e-64-o2113-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032649/nc2115Isup2.hkl

e-64-o2113-Isup2.hkl^{(100.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9A⋯Cl2	0.86	2.14	3.001 (3)	177
N10—H10A⋯Cl1	0.86	2.33	3.088 (3)	147
N2—H2⋯Cl2	0.86	2.22	3.050 (4)	163
N5—H5A⋯Cl1ⁱ	0.86	2.29	3.049 (3)	147
N5—H5A⋯N1	0.86	2.55	2.881 (4)	104
N10—H10A⋯N6	0.86	2.52	2.858 (4)	105
C9—H9⋯Cl2	0.93	2.64	3.545 (4)	165
C3—H3⋯N8ⁱⁱ	0.93	2.60	3.329 (5)	136
C6—H6⋯N6ⁱ	0.93	2.38	3.260 (5)	159
C10—H10⋯Cl1ⁱⁱⁱ	0.93	2.67	3.596 (4)	174

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Tetrazole derivatives have found wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Wang et al., 2005; Xiong et al., 2002; Wen, 2008). In our ongoing investigations in this field we report here the crystal of 2-(2H-tetrazol-5-yl)pyridine-1-ium chloride (Fig.1).

In the crystal structure there are two crystallographically independent molecules, both of them located on mirror planes. Therefore, the benzene and tetrazole rings in both independent molecules are essentially planar. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Wang et al., 2005; Dai & Fu, 2008).

The crystal structure is stabilized by N—H···Cl, C—H···Cl, C—H···N and N—H···N hydrogen bonding. The different H bonding interactions connect the molecules into layers, that are parallel to the (0 0 1) plane (Table 1, Fig. 2).

Experimental

Picolinonitrile (30 mmol), NaN ₃ (45 mmol), NH₄Cl (33 mmol) and DMF (50 ml) were added in a flask under nitrogen atmosphere and the mixture stirred at 110°C for 20 h. The resulting solution was then poured into ice-water (100 ml), and a white solid was obtained after adding HCl (6 M) till pH=6. The precipitate was filtered and washed with distilled water. Colourless block-shaped crystals suitable for X-ray analysis were obtained from the crude product by slow evaporation of the solvent from an ethanol/HCl (50:1 v/v) solution.