N-(2-Nitrooxyethyl)picolinamide

In the title molecule, C8H9N3O4, the amide group is involved in the formation of an intramolecular N—H⋯N hydrogen bond. In the crystal, molecules related by translation along the a axis are linked into chains via weak intermolecular C—H⋯O interactions.

In the title molecule, C 8 H 9 N 3 O 4 , the amide group is involved in the formation of an intramolecular N-HÁ Á ÁN hydrogen bond. In the crystal, molecules related by translation along the a axis are linked into chains via weak intermolecular C-HÁ Á ÁO interactions.

Comment
The title compound (I) can be considered as a potential nitric oxide donating drug. Herewith we present its crystal structure.
The molecule of (I) adopts a folded conformation and contains a planar pyridine cycle (NC 5 H 4 ) bearing a CO group attached to the α-carbon atom (Fig. 1). The dihedral angle between the pyridine ring and the O1/C6/N2 plane is 11.3 (2)°.
The crystal structure of (I) is stabilized through weak non-classical intermolecular H-bonds of the type C-H···O in [100] direction, involving the carbon atom of the nitrooxyethyl group and the oxygen atom of carbonylamide. Moreover, were observed one intramolecular interactions of the type N-H···N (Table 1). On the other hand, the compound nicorandil has only one intermolecular interaction of the type N-H···O. The results for compound (I) and its structural isomers show that the position of the ligand in pyridine ring affects the conformation of the molecule and the interactions present in the crystal packing.
The reaction mixture was poured into water and ice, and the pH was adjusted to 6.0 adding (CaCO 3 ). The white solid obtained was filtered at reduced pressure and recrystallized in ethanol, forming the N-(2-nitrooxyethyl)picolinamide in 63% yield (Jiao et al., 1990) Fig. 1. The molecular structure of (I) showing the atom labeling. Displacement ellipsoids are drawn at the 30% probability level. 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 > σ(F 2 ) is used only for calculating Rfactors(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.