N-(3-Hy­droxy­phen­yl)nicotinamide

Chunhua Ge; Rui Zhang; Xiangdong Zhang; Chenglong Zhang; Meiyin Zhang

doi:10.1107/S1600536812015620

. 2012 Apr 21;68(Pt 5):o1499. doi: 10.1107/S1600536812015620

N-(3-Hydroxyphenyl)nicotinamide

Chunhua Ge ^a, Rui Zhang ^a,^*, Xiangdong Zhang ^a, Chenglong Zhang ^a, Meiyin Zhang ^a

PMCID: PMC3344608 PMID: 22590370

Abstract

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.

Related literature

For related structures, see: Mocilac & Gallagher (2011 ▶); Roopan et al. (2009 ▶). For modern aspects of boronic acid derivatives, see: Hall (2005 ▶).

Experimental

Crystal data

C₁₂H₁₀N₂O₂
M _r = 214.22
Monoclinic,
a = 12.1741 (13) Å
b = 5.2613 (6) Å
c = 15.3113 (16) Å
β = 94.428 (2)°
V = 977.79 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.35 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.952, T _max = 0.988
5813 measured reflections
1928 independent reflections
1572 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.098
S = 1.04
1928 reflections
150 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015620/cv5281sup1.cif

e-68-o1499-sup1.cif^{(14.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015620/cv5281Isup2.hkl

e-68-o1499-Isup2.hkl^{(94.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015620/cv5281Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯N1ⁱ	0.82	2.00	2.817 (2)	173
N2—H2A⋯O1ⁱⁱ	0.83 (2)	2.29 (2)	3.107 (2)	166

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant Nos. 20971062 and 21171081) and the Foundation of the 211 Project for Innovative Talents Training, Liaoning University.

supplementary crystallographic information

Comment

Organoboronic acid derivatives have recently received increasing interest in a broad range of biological, medicinal, and synthetic applications (Hall, 2005). Especially, such compounds have been utilized as synthetic intermediates. For example, the famous Suzuki reaction is the coupling of organoboronic acid with aryl halide. Boronic acid containing compounds employed in the cross coupling must be activated by using palladium catalyst. Other metal ion could make boronic acid in the different transformational mode.

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.