5,5'-(p-Phenyl-ene)di-1H-tetra-zole.

Crystals of the title organic compound, C(8)H(6)N(8), were generated in situ through the [2 + 3]-cyclo-addition reaction involving the precursor 1,4-dicyano-benzene and azide in water with Zn(2+) as Lewis acid. The asymmetric unit consists of one half-mol-ecule, and a twofold axis of symmetry passes through the centre of the benzene ring. There is an inter-molecular N-H⋯N hydrogen bond. The mol-ecules are assembled into a three-dimensional supra-molecular framework by π-π stacking inter-actions, with a perpendicular distance of 3.256 Å [centroid-centroid = 3.9731 (8) Å] between two tetra-zole ring planes, and 3.382 Å between the benz-ene ring and tetra-zole ring planes [centroid-centroid = 3.5010 (9) Å].