5-(Pyridinium-4-yl)-1H-1,2,3,4-tetra­zol-1-ide

Qian Xu; Jie Xu

doi:10.1107/S1600536810050257

. 2010 Dec 8;67(Pt 1):o43. doi: 10.1107/S1600536810050257

5-(Pyridinium-4-yl)-1H-1,2,3,4-tetrazol-1-ide

Qian Xu ^a,^*, Jie Xu ^a

PMCID: PMC3050385 PMID: 21522752

Abstract

In the title zwitterionic molecule, C₆H₅N₅, the tetrazole and pyridine rings are nearly coplanar, making a dihedral angle of 2.08 (1)°. In the crystal, molecules are connected by classical N—H⋯N and weak C—H⋯N hydrogen bonds.

Related literature

For applications of tetrazole derivatives, see: Zhao et al. (2008 ▶); Fu et al. (2008 ▶, 2009 ▶). For the crystal structures and properties of related compounds, see: Fu et al. (2007 ▶, 2009 ▶); Fu & Xiong (2008 ▶).

Experimental

Crystal data

C₆H₅N₅
M _r = 147.15
Monoclinic,
a = 7.0508 (14) Å
b = 7.4007 (15) Å
c = 11.926 (2) Å
β = 96.56 (3)°
V = 618.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
3122 measured reflections
719 independent reflections
633 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.096
S = 1.13
719 reflections
100 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050257/xu5093sup1.cif

e-67-00o43-sup1.cif^{(12.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050257/xu5093Isup2.hkl

e-67-00o43-Isup2.hkl^{(35.9KB, 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
N1—H1A⋯N2ⁱ	0.86	1.89	2.745 (4)	176
N1—H1A⋯N3ⁱ	0.86	2.52	3.306 (4)	152
C1—H1⋯N5ⁱⁱ	0.93	2.46	3.308 (4)	152
C5—H5⋯N4ⁱⁱⁱ	0.93	2.38	3.168 (4)	142

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

Acknowledgments

This work was supported by a start-up grant from Southeast University, China.

supplementary crystallographic information

Comment

Tetrazole compounds attracted more attention as phase transition dielectric materials for its application in micro-electronics, memory storage. With the purpose of obtaining phase transition crystals of tetrazole compound, a series of new materials have been elaborated with this organic molecule (Zhao et al., 2008; Fu et al., 2008; Fu et al., 2007; Fu & Xiong 2008). We report here the crystal structure of the title compound, 5-(pyridinium-4-yl)tetrazol-1-ide.

The dielectric constant of title compound as a function of temperature indicates that the permittivity is basically temperature-independent, suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (413K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 6.1 to 7.9).

In the title compound (Fig.1), the pyridine N atom is protonated, thus indicating a positive charge in the pyridine N atom. And the tetrazole ring was showing a negative charge to make the charge balance. The tetrazole and pyridine rings are twisted from each other by a dihedral angle of 2.08 (1)°. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Fu et al., 2009).

In the crystal structure the molecules are connected by classic N—H···N and weak C—H···N hydrogen bonds (Table 1).

Experimental

5-(Pyridinium-4-yl)tetrazol-1-ide was obtained commercially, and the single crystals were obtained from an ethanol solution.