5-(2-Bromophenyl)-1,3,4-thiadiazol-2-amine

In the title compound, C8H6BrN3S, the thiadiazole ring is oriented at a dihedral angle of 48.35 (3)° with respect to the bromophenyl ring. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules.

In the title compound, C 8 H 6 BrN 3 S, the thiadiazole ring is oriented at a dihedral angle of 48.35 (3) with respect to the bromophenyl ring. In the crystal structure, intermolecular N-HÁ Á ÁN hydrogen bonds link the molecules.
In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental
For the preparation of the title compound, 2-bromobenzoic acid (5 mmol) and thiosemicarbazide (5 mmol) were added in toluene (50 ml), which is heated under reflux for 4 h. The reaction mixture was left to cool to room temperature, poured into ice water, filtered, and the filter cake was crystallized from acetone to give title compound (m.p. 486-487 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.

Refinement
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH 2 ) and C-H = 0.93 Å for aromatic H, respectively, and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C,N).

Data collection
Enraf-Nonius CAD-4 diffractometer R int = 0.034 Radiation source: fine-focus sealed tube θ max = 25.2º Monochromator: graphite θ min = 1.4º T = 298(2) K h = −17→17 ω/2θ scans k = 0→9 Absorption correction: ψ scan (North et al., 1968) l = 0→9 Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.