(E)-4-[(4-Amino-5-bromopyridin-3-yl)iminomethyl]phenol

In the molecule of the title compound, C12H10BrN3O, the pyridine and benzene rings are oriented at a dihedral angle of 34.93 (3)°. Intramolecular N—H⋯N and N—H⋯Br hydrogen bonds result in the formation of two non-planar five-membered rings. In the crystal structure, intermolecular O—H⋯N and N—H⋯O hydrogen bonds link the molecules to form a three-dimensional network.

In the molecule of the title compound, C 12 H 10 BrN 3 O, the pyridine and benzene rings are oriented at a dihedral angle of 34.93 (3) . Intramolecular N-HÁ Á ÁN and N-HÁ Á ÁBr hydrogen bonds result in the formation of two non-planar five-membered rings. In the crystal structure, intermolecular O-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds link the molecules to form a three-dimensional network.

Related literature
For general background, see: Liu et al. (2002).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2438). Lawessen regent are very active (Liu et al., 2002). We have recently synthesized the novel title compound, (I), and report herein its crystal structure.
In the molecule of the title compound, (I), ( In the crystal structure, intermolecular O-H···N and N-H···O hydrogen bonds (Table 1) link the molecules to form a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.
Experimental 5-bromopyridine-3,4-diamine (1.88 g, 10 mmol) was added to a solution of 4-hydroxybenzaldehyde (1.22 g, 10 mmol)in MeOH (50 ml). The solution was refluxed for 10 h, and then dried over magnesium sulfate, filtered and the volatiles were removed under reduced pressure. The crude product was further purified and recystallized from MeOH affording yellow crystals of (I) (yield; 70%).

Refinement
H atoms (for NH 2 ) were located in a difference synthesis and refined isotropically [N-H = 0.876 (10)    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 > 2sigma(F 2 ) is used only for calculating R-factors(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.