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. 2008 Dec 17;65(Pt 1):o126.
doi: 10.1107/S1600536808042165.

3-Phenyl-1H-1,2,4-triazol-5-amine-5-phenyl-1H-1,2,4-triazol-3-amine (1/1)

Anton V Dolzhenko, Geok Kheng Tan, Lip Lin Koh, Anna V Dolzhenko, Wai Keung Chui

3-Phenyl-1H-1,2,4-triazol-5-amine-5-phenyl-1H-1,2,4-triazol-3-amine (1/1)

Anton V Dolzhenko et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

In the title compound, C(8)H(8)N(4)·C(8)H(8)N(4), two tautomers, viz. 3-phenyl-1,2,4-triazol-5-amine and 5-phenyl-1,2,4-triazol-3-amine, are crystallized together in equal amounts. The 3-phenyl-1,2,4-triazol-5-amine mol-ecule is essentially planar; the phenyl ring makes a dihedral angle of 2.3 (2)° with the mean plane of the 1,2,4-triazole ring. In the 5-phenyl-1,2,4-triazol-3-amine tautomer, the mean planes of the phenyl and 1,2,4-triazole rings form a dihedral angle of 30.8 (2)°. The π-electron delocalization of the amino group with the 1,2,4-triazole nucleus in the 3-phenyl-1,2,4-triazol-5-amine mol-ecule is more extensive than that in the 5-phenyl-1,2,4-triazol-3-amine tautomer. The mol-ecules are linked into a two-dimensional network parallel to (100) by N-H⋯N hydrogen bonds.

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Figures

Fig. 1.
Fig. 1.
Possible tautomers of 3(5)-phenyl-1,2,4-triazol-5(3)-amine.
Fig. 2.
Fig. 2.
The molecular structure of 3(5)-phenyl-1,2,4-triazol-5(3)-amine with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 3.
Fig. 3.
Molecular packing in the crystal, viewed along the b axis. Hydrogen bonds are shown as dashed lines.
See this image and copyright information in PMC

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