6-Nicotinamido-2-naphthoic acid

In the title molecule, C17H12N2O3, the naphthalene ring system and the pyridin-3-yl rings are nearly coplanar with a dihedral angle between them of 2.28 (8)°. In the crystal, the hydroxy and amide N atoms participate in hydrogen bonds, which connect the molecules into a two-dimensional network parallel to (101).

In the title molecule, C 17 H 12 N 2 O 3 , the naphthalene ring system and the pyridin-3-yl rings are nearly coplanar with a dihedral angle between them of 2.28 (8) . In the crystal, the hydroxy and amide N atoms participate in hydrogen bonds, which connect the molecules into a two-dimensional network parallel to (101).
supplementary materials Acta Cryst. (2012). E68, o1978 [doi:10.1107/S1600536812024051] 6-Nicotinamido-2-naphthoic acid Yun-Sung Song and Soon W. Lee Comment Bis(pyridyl)-and dicarboxylate-type linking ligands have been typically employed for the preparation of coordination polymers (Robin & Fromm, 2006). The vast majority of known coordination polymers contain either a d-or an f-block metal. However, several research groups recently prepared polymers containing both d-and f-block metals within their frameworks by utilizing linking ligands possessing pyridyl-carboxylate terminal groups (Hu et al., 2012;Chen et al., 2010;Tang et al., 2010;Yue et al., 2011;Zhu et al., 2010). Consistent with the hard-soft acid-base concept, the harder oxygen atoms are bonded to the f-block metals and the softer nitrogen atoms are bonded to the d-block metals in these polymers. Our research group recently reported the structures of two potential linking ligands with pyridyl-carboxylate terminal groups (Han & Lee, 2012;Zheng & Lee, 2012) and here we report the structure of third.
The molecular structure of the title molecule with the atom-labeling scheme is given in Figure 1. The naphthalene and 3-pyridyl rings are nearly coplanar with a dihedral angle between them of 2.28 (8)°. The N2-C6 bond length (1.343 (2) Å) indicates a C-N single bond. The intermolecular O-H···N and N-H···O (carbonyl) hydrogen bonds (Table 1)

Refinement
All non-hydrogen atoms were refined anisotropically. C-bound H atoms were positioned geometrically [C-H = 0.93-0.97 A] and allowed to ride on their parent atoms, with U iso (H) = 1.2U eq (C). The hydrogen atoms attached to N and O were located in a difference Fourier map and refined isotropically.

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 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.