rac-N-[Hy­droxy(4-pyrid­yl)meth­yl]picolinamide: a hemiamidal

The title compound, C(12)H(11)N(3)O(2), a hemiamidal, was synthesized by solvent-free aldol condensation at room temperature by grinding picolinamide with isonicotinaldehyde in a 1:1 molar ratio. In the mol­ecule, the two pyridine rings are inclined to one another by 58.75 (6)°. They are linked, at positions 2 and 4, by the hemiamidal bridge (–CO—NH—CHOH–). The NH-group H atom forms an intra­molecular hydrogen bond with the N atom of the picolinamide pyridine ring. In the crystal, symmetry-related mol­ecules are linked via N—H⋯O hydrogen bonds, involving the NH group H atom of the hemiamidal bridge and the hy­droxy O atom, forming inversion-related dimers, with graph-set R (2) (2)(8). Adjacent mol­ecules are also linked via O—H⋯N hydrogen bonds, involving the hy­droxy substituent and the 4-pyridine N atom. Together these inter­actions lead to the formation of double-stranded ribbon-like hydrogen-bonded polymers propagating in [010]. The latter are further connected via C—H⋯O hydrogen bonds involving the carbonyl O atom, so forming a two-dimensional network in (011).