4-(2H-Tetra­zol-5-yl)pyridinium perchlorate

Jing Dai

doi:10.1107/S1600536809018200

. 2009 May 20;65(Pt 6):o1349. doi: 10.1107/S1600536809018200

4-(2H-Tetrazol-5-yl)pyridinium perchlorate

Jing Dai ^a,^*

PMCID: PMC2969801 PMID: 21583201

Abstract

In the cation of the title compound, C₆H₆N₅ ⁺·ClO₄ ⁻, the pyridinium and tetrazole rings form a dihedral angle of 23.6 (1)°. In the crystal structure, weak intermolecular N—H⋯O and N—H⋯N hydrogen bonds link cations and anions into chains extending along the b axis.

Related literature

For applications of tetrazole derivatives in coordination chemistry, see: Xiong et al. (2002 ▶); Wang et al. (2005 ▶). For related structures, see: Dai & Fu (2008 ▶); Wen (2008 ▶).

Experimental

Crystal data

C₆H₆N₅ ⁺·ClO₄ ⁻
M _r = 247.61
Monoclinic,
a = 5.2033 (10) Å
b = 14.764 (3) Å
c = 12.244 (2) Å
β = 101.78 (3)°
V = 920.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 298 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.872, T _max = 1.000 (expected range = 0.801–0.919)
9546 measured reflections
2108 independent reflections
1849 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.093
S = 1.09
2108 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.37 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/S1600536809018200/cv2545sup1.cif

e-65-o1349-sup1.cif^{(14.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018200/cv2545Isup2.hkl

e-65-o1349-Isup2.hkl^{(103.7KB, 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
N5—H5A⋯O3ⁱ	0.86	2.28	2.964 (2)	136
N5—H5A⋯N2ⁱⁱ	0.86	2.38	3.059 (2)	136
N3—H3A⋯O4ⁱⁱⁱ	0.86	2.21	2.884 (2)	135

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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

In the past few years, more and more people have focused their attention on the chemistry of tetrazole derivatives 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). We report here the crystal structure of the title compound, 4-(2H-tetrazol-5-yl)pyridinium perchlorate).

In the title compound (Fig.1), the pyridine N atom is protonated. The pyridine ring makes a dihedral angle of 23.62 (1)° with the tetrazole ring. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Wang et al. 2005; Dai & Fu, 2008).

The crystal packing is stabilized by N—H···O and N—H···N hydrogen bonds (Table 1) with the formation of zig-zag chains parallel to b axis.

Experimental

Isonicotinonitrile (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 an ethanol/HClO₄ (50:1 v/v) solution.