N-(3-Hydroxyphenyl)nicotinamide

In the title molecule, C12H10N2O2, the benzene and pyridine rings form a dihedral angle of 5.01 (8)°. The amide group is twisted by 33.54 (7)° from the plane of the pyridine ring. In the crystal, molecules are linked into centrosymmetric dimers via pairs of O—H⋯N hydrogen bonds. N—H⋯O hydrogen bonds further link dimers related into chains along the b axis.

In the title molecule, C 12 H 10 N 2 O 2 , the benzene and pyridine rings form a dihedral angle of 5.01 (8) . The amide group is twisted by 33.54 (7) from the plane of the pyridine ring. In the crystal, molecules are linked into centrosymmetric dimers via pairs of O-HÁ Á ÁN hydrogen bonds. N-HÁ Á ÁO hydrogen bonds further link dimers related into chains along the b axis.
The title compound, N-(3-hydroxyphenyl)nicotinamide, is obtained by reaction of N-(3-phenylboronic acid)nicotinamide with copper(II) ion. The molecular structure is shown in Fig. 1. Conformational studies show that substituent of the phenyl ring is one of key factors for solid state molecular conformations and supramolecular aggregation. Comparisons between N-phenylnicotinamide and N-(3-hydroxyphenyl)nicotinamide reveal that the dihedral angle between the phenyl and pyridine rings is 64.81 (1) ° (Roopan et al., 2009) in the former and 5.02 (8) ° in the latter.
This value in N-(3-methylphenyl)nicotinamide is 57.23 (6) ° (Mocilac & Gallagher, 2011). Oxygen atom from amide group and nitrogen atom from pyridine ring in N-phenylnicotinamide are on the same side of the molecule. The distribution of corresponding atoms in N-(3-methylphenyl)nicotinamide is similar to that of N-phenylnicotinamide, but contrary to that of N-(3-hydroxyphenyl)nicotinamide.
In the crystal structure, the molecules are paired into centrosymmetric dimers via O-H···N hydrogen bonds (Table 1).
Intermolecular N-H···O hydrogen bonds (Table 1) link further these dimers related be translation along axis b into chains.
Experimental N-(3-Phenylboronic acid)nicotinamide (10 mmol) was added to 20 ml e thanol-water(v:v=8:2), followed by the dropwise addition of copper nitrate(5 mmol) in 5 ml water. The mixture was stirred at room temperature for 8 h. After filtered, the filtrate was evaporated. Crystals were obtained after about two weeks.

Refinement
The amide H atom was located in Fourier different map and refined isotropically. All other H atoms were placed in geometrically idealized positions (Csp 2 -H = 0.93, and O-H = 0.82) and refined as riding, with U iso (H) = 1.2U eq (C) and U iso (H) = 1.5U eq (O).

Computing details
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).  The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. 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.