Benzoylmethyl pyridine-4-carboxylate

In the crystal structure of the title compound, C14H11NO3, isolated from the reaction of 2-bromo-1-phenylethanone and pyridine-4-carboxylic acid using triethylamine as a base to deprotonate the organic acid, the molecular packing is stabilized by C—H⋯π interactions involving the phenyl and pyridine rings. The C—C—O—C torsion angle for the linkage between the two carbonyl groups is −80.8 (2)°, and the planes of the phenyl and pyridyl rings form a dihedral angle of 65.8 (1)°.


Comment
The title compound was synthesized for a study of protection of the carboxyl group. The phenacyl group has been proved to be an important reagent for protecting carboxyl functions during synthesis in the presence of other esters (Hendrickson et al., 1970).
The title compound (I) was obtained by the reaction of 2-bromo-1-phenylethanone and pyridine-4-carboxylic acid using triethylamine as a base to deprotonate the organic acid. An X-ray crystal structure determination of compound (I) was carried out to determine its conformation. Bond lengths and angles are in agreement with values reported in the literature (Allen et al., 1987). The torsion angle C7-C8-O9-C10 [-80.8 (2)Å] describes the conformation of the phenyl group with respect to the pyridyl group; the planes of the benzene ring and the pyridine ring form a dihedral angle of 65.8 (1)Å.
In the crystal structure of (I), the phenyl and pyridyl rings make a dihedral angle of 65.8 (1)° and the C7-C8-O9-C10 torsion angle is -80.8 (2)° (Fig. 1). The packing of the aromatic rings is shown in Fig. 2. Two head-to-tail molecules (M and M i ) are linked by C-H···π interactions with typical geometry (Pavel et al., 1993), leading to the formation of a linear chain.
The distance between CgA and CgB i is 6.102 (3) Å and the angles between the lines through the centroids of the two rings
The precipitate was collected at the pump and washed with ethyl acetate. The filtrate and washings were combined and back-washed successively with 1/3 of the volume each of 10% citric acid, 10% sodium bicarbonate, and water and then dried. Solvent was distilled off in vacuo and the residue recrystallized repeatedly from ethyl acetate-petroleum ether, giving 1.04 g (86%) as colourless needles.

Refinement
The hydrogen atoms were positioned geometrically (C-H = 0.93, 0.98, 0.97 or 0.96Å for aromatic, tertiary, methylene or methyl H atoms respectively) and were included in the refinement in the riding model approximation. The displacement parameters of methyl H atoms were set to 1.5U eq (C), while those of other H atoms were set to 1.2U eq (C). Fig. 1. The molecular structure of (I) with the atom-labelling scheme, showing 50% probability displacement ellipsoids. H atoms are drawn as spheres of arbitrary radius.