Methyl 4-isonicotinamidobenzoate monohydrate

The title compound, C14H12N2O3·H2O, synthesized by the reaction of methyl 4-aminobenzoate with isonicotinoyl chloride hydrochloride, is relatively planar, with the pyridine ring being inclined by 7.46 (7)° to the benzene ring. In the crystal, the methyl 4-isonicotinamidobenzoate molecules are interlinked by water molecules via N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, leading to the formation of a double-chain ribbon-like structure.

The title compound, C 14 H 12 N 2 O 3 ÁH 2 O, synthesized by the reaction of methyl 4-aminobenzoate with isonicotinoyl chloride hydrochloride, is relatively planar, with the pyridine ring being inclined by 7.46 (7) to the benzene ring. In the crystal, the methyl 4-isonicotinamidobenzoate molecules are interlinked by water molecules via N-HÁ Á ÁO, O-HÁ Á ÁN and O-HÁ Á ÁO hydrogen bonds, leading to the formation of a double-chain ribbon-like structure.

Comment
The title compound was synthesized as a potential ligand for use in coordination chemistry (Saeed et al., 2010;Kitagawa, 2005). It was synthesized via the reacton of methyl 4-benzoate with isonicotinoyl.HCl and contains both a coordination site [the N atom in the pyridyl ring], and a guest interaction site [the amide group].
The molecular structure of the title compound is illustrated in Fig. 1. The bond distances are normal (Allen et al., 1987), and the molecule is relatively planar with the dihedral angle involving the pyridine and benezene rings being 7.46 (7)°.
In the crystal molecules are connected by hydrogen bonds, with the water molecule H-atoms serving as hydrogen-bond donors and the pyridyl nitrogen and ester oxygen atoms serving as acceptors ( Fig. 2 and Table 1). At the same time, the amide nitrogen atom acts as a hydrogen-bond donor and the water oxygen atom as a hydrogen-bond acceptor. In this way a double stranded ribbon-like structure is formed with base vector [11-1].
The white precipitate that formed was filtered off and washed with distilled water and then dried. Colourless block-like crystals, suitable for x-ray analysis, were obtained from a DMF-methanol solution (1:1; v:v) via vapour evaporation at room temperature after two weeks.

Refinement
The water molecule H-atoms were located in a difference Fourier map and were refined with U iso (H) = 1.5U eq (Ow) and a restrained bond distance of 0.85 (2) Å. The remaining H-atoms were positioned geometrically and refined using a riding model: N-H = 0.86 Å, C-H = 0.93-0.96 Å with U iso (H) = k × U eq (N,C), where k = 1.2 for NH, CH and CH 2 H-atoms, and k = 1.5 for CH 3 H-atoms. Fig. 1. The molecular structure of the title compound, with atom labels and displacement ellipsoids drawn at the 50% probability level.

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