5-p-Tolyl-1H-tetrazole

The title compound, C8H8N4, possesses crystallographic mirror symmetry, with four C atoms lying on the reflecting plane, which bisects the phenyl and tetrazole rings. It is composed of a planar r.m.s. deviation (0.0012 Å) tetrazole ring which is nearly coplanar with the benzene ring, the dihedral angle being 2.67 (9)°. In the crystal, symmetry-related molecules are linked by intermolecular N—H⋯N hydrogen bonds. The molecules stack along [100] with a π⋯π interaction involving the phenyl and tetrazole rings of adjacent molecules [centroid–centroid distance = 3.5639 (15) Å]. The H atom of the N—H group is disordered over two sites of equal occupancy. The methyl H atoms were modelled as disordered over two sets of sites of equal occupancy rotated by 60° with respect to each other.

The title compound, C 8 H 8 N 4 , possesses crystallographic mirror symmetry, with four C atoms lying on the reflecting plane, which bisects the phenyl and tetrazole rings. It is composed of a planar r.m.s. deviation (0.0012 Å ) tetrazole ring which is nearly coplanar with the benzene ring, the dihedral angle being 2.67 (9) . In the crystal, symmetry-related molecules are linked by intermolecular N-HÁ Á ÁN hydrogen bonds. The molecules stack along [100] with a Á Á Á interaction involving the phenyl and tetrazole rings of adjacent molecules [centroid-centroid distance = 3.5639 (15) Å ]. The H atom of the N-H group is disordered over two sites of equal occupancy. The methyl H atoms were modelled as disordered over two sets of sites of equal occupancy rotated by 60 with respect to each other.

Structure Reports Online
The title compound is a tetrazole ligand with a toluene substituent in position 5 (Fig. 1). In the solid state structure the molecule possesses crystallographic mirror symmetry. The mirror bisects the toluyl group and the tetrazole ring with atoms C1, C4, C7 and C8 lieing in the mirror. The bond lengths and angles have normal values. The interplanar angle between the phenyl ring [C1/C2/C3/C4/C2A/C3A] and the tetrazole ring [N1/N2/N1A/N2A/C7] mean-planes is 2.67 (9) °.
In the crystal symmetry related molecules are linked by intermolecular N-H···N hydrogen bonds (Table 1), forming chains propagating in the [010] direction (Fig. 2). There is a π···π interaction involving the tetrazole and phenyl rings of adjacent molecules with a centroid-to-centroid distance of 3.5639 (15) Å.
Experimental 4-methylbenzonitrile (1.17 g, 10 mmol) and ammonium chloride (0.53 g, 10 mmol) were dissolved in DMF (40 ml) in the presence of sodium azidein (0.98 g, 0.5 mmol) and refluxed for 24 h. After the mixture was cooled to rt and filtered. Most of the solvent was then removed under vacuum. Pale yellow crystals of the title compound, suitable for X-ray diffraction analysis, were obtained from the remaining solution on slow evaporation of the solvent.

Refinement
All the H atoms could be located in the difference electron-density maps. Due to the mirror symmetry the NH H-atom, which is disorderd over N-atoms N1 and N1 i [symmetry code (i) = x, y, -z+1/2], was freely refined with an occupancy of 0.5; distance N-H = 0.87 (3) Å. The C-bound H-atoms were included in idealized positions and treated as riding atoms: C-H = 0.93 -0.96 Å, with U iso (H) = 1.2U eq (parent C-atom). The H-atoms on methyl C8 were modelled as disordered with two triplets of the H atoms with equal occupation (0.5:0.5) rotated by 60° to each other.   Table 1 for details).  (2) C4-C8 1.507 (3)