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

Abstract

The title compound, C12H11N3O2, 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 R22(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).