2-(Benzylcarbamoyl)nicotinic acid

In the title compound, C14H12N2O3, the pyridine ring is twisted with respect to the phenyl ring and the carboxylic acid group at angles of 37.1 (5) and 8.1 (3)°, respectively; the phenyl ring forms a dihedral angle of 41.4 (1)° with the mean plane of the C—NH—C=O fragment. An intramolecular O—H⋯O hydrogen bond occurs between the carboxylic acid and carbonyl groups. In the crystal, N—H⋯O hydrogen bonds link molecules into a supramolecular chain running along the a-axis direction.

In the title compound, C 14 H 12 N 2 O 3 , the pyridine ring is twisted with respect to the phenyl ring and the carboxylic acid group at angles of 37.1 (5) and 8.1 (3) , respectively; the phenyl ring forms a dihedral angle of 41.4 (1) with the mean plane of the C-NH-C O fragment. An intramolecular O-HÁ Á ÁO hydrogen bond occurs between the carboxylic acid and carbonyl groups. In the crystal, N-HÁ Á ÁO hydrogen bonds link molecules into a supramolecular chain running along the a-axis direction.

Comment
Drugs that reduce blood coagulation and are widely used for therapy and prevention in surgical operations and for ischemic heart disease and other diseases are known to have several serious shortcomings (Konshin et al., 2010). Our research on biologically active amides and hydrazides of pyridinecarboxylic acids led to the synthesis of substituted 3carboxypicolinic acid amides.
The molecular structure of the title compound is shown in Fig. 1. The pyridine ring is twisted by 37.1 (5) and 8.1 (3)°, with respect to the benzene ring and carboxyl group; the benzene ring forms a dihedral angle of 41.4 (1)° with the mean plane of the C-NH-C═O fragment.
As shown in Figure 2, the molecules are linked by N-H···O hydrogen bonds into chain in the crystal lattice (Table 1).

Experimental
A solution of quinolinic acid anhydride (20 mmol) in CHCl 3 (20 ml) was treated with Et 3 N (20 mmol). Then a solution of phenylmethanamine (20 mmol) in CHCl 3 (15 ml) was added gradually at a rate such that the temperature of the mixture did not rise above 303 K. The mixture was left for 12 h. The resulting precipitate was filtered off, dissolved in the minimum amount of water, and precipitated by acetic acid. The precipitate was separated, washed with water and recrystallized from EtOH.

Refinement
H atoms were positioned geometrically, with O-H = 0.82 Å and N-H = 0.86 Å and C-H = 0.93 and 0.97 Å for aromatic and methine H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C,N,O), where x =1.5 for carboxyl H, and x = 1.2 for all other H atoms.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. 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 R-factors(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.