rac-N-[Hy-droxy(4-pyrid-yl)meth-yl]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 mol-ecule, 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 intra-molecular hydrogen bond with the N atom of the picolinamide pyridine ring. In the crystal, symmetry-related mol-ecules are linked via N-H⋯O hydrogen bonds, involving the NH group H atom of the hemiamidal bridge and the hy-droxy O atom, forming inversion-related dimers, with graph-set R(2) (2)(8). Adjacent mol-ecules are also linked via O-H⋯N hydrogen bonds, involving the hy-droxy substituent and the 4-pyridine N atom. Together these inter-actions 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).