2-{[(Pyridin-2-yl)amino]methyl}phenol

The planes of the aromatic rings of the title compound, C12H12N2O, are twisted by 50.33 (15)°. The phenol O atom is a hydrogen-bond donor to the pyridine N atom, resulting in the formation of an eight-membered ring in the molecule. The amino N atom is a hydrogen-bond donor to the phenol O atom of an adjacent molecule; this hydrogen bond leads to the formation of a helical chain that runs along the a axis.

The planes of the aromatic rings of the title compound, C 12 H 12 N 2 O, are twisted by 50.33 (15) . The phenol O atom is a hydrogen-bond donor to the pyridine N atom, resulting in the formation of an eight-membered ring in the molecule. The amino N atom is a hydrogen-bond donor to the phenol O atom of an adjacent molecule; this hydrogen bond leads to the formation of a helical chain that runs along the a axis.

2-{[(Pyridin-2-yl)amino]methyl}phenol Shan Gao and Seik Weng Ng Comment
Salicylaldehyde condenses with aromatic amines to yield Schiff bases, which serve as chelating ligands to a plethora of metal systems. These Schiff bases can be readily reduce to the corresponding secondary amines, which can also function as chelating ligands. Curiously, there are only few 2-(arylamino)methylphenols compared with the plethora of Schiff bases in the chemical literature. Among the aminopyridine derivatives, only the crystal structure of 2-((pyridin-3-ylamino)methyl)phenol has been reported (Xu et al., 2011). The 2-((pyridin-2-ylamino)methyl)phenol analog (Scheme I) has been described as its metal adducts only (Yalçın et al., 2007).
The two aromatic rings of the reduced Schiff-base, C 12 H 12 N 2 O, are twisted along the -CH 2 -NH-single-bond by 50. 3 (1) °. The hydroxy O atom is hydrogen-bond donor to the pyridyl N atom and an eight-membered ring is formed (Fig. 1).
The slightly flattened secondary amino N atom is hydrogen-bond donor to the O atom of an adjacent molecule; this hydrogen bond leads to the formation of a helical chain that runs along the a-axis of the orthorhombic unit cell (Fig. 2, Table 1).

Experimental
A solution of 2-aminopyridine (1 mmol) and salicylaldehyde (1 mmol) in toluene (50 ml) was heated for 10 h. The solvent was removed under vacuum, and the residue was reduced in absolute methanol by sodium borohydride. Light yellow crystals were obtained by recrystallization from methanol in 80% yield.

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints N-H 0.88±0.01 Å and O-H 0.84±0.01 Å; their temperature factors were refined.
In the absence of heavy scatters, 980 Friedel pairs were merged.