N-Phenyl­nicotinamide

S Mohana Roopan; Venkatesha R Hathwar; A Sudheer Kumar; N Malathi; F Nawaz Khan

doi:10.1107/S1600536809004863

. 2009 Feb 21;65(Pt 3):o571. doi: 10.1107/S1600536809004863

N-Phenylnicotinamide

S Mohana Roopan ^a, Venkatesha R Hathwar ^b, A Sudheer Kumar ^a, N Malathi ^a, F Nawaz Khan ^a,^*

PMCID: PMC2968688 PMID: 21582226

Abstract

In the title compound, C₁₂H₁₀N₂O, the dihedral angle between the phenyl and pyridine rings is 64.81 (1)°. Intermolecular N—H⋯O hydrogen bonds connect the molecules into chains running along the b axis.

Related literature

For general background, see: de Souza et al. (2005 ▶); Gdaniec et al. (1979 ▶). For related crystal structures, see: Cuffini et al. (2006 ▶). For graph-set motifs, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₂H₁₀N₂O
M _r = 198.22
Monoclinic,
a = 18.732 (4) Å
b = 5.2766 (11) Å
c = 20.248 (4) Å
β = 103.746 (4)°
V = 1944.0 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 K
0.23 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.917, T _max = 0.990
6923 measured reflections
1813 independent reflections
1287 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.112
S = 1.03
1813 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS90 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004863/bt2869sup1.cif

e-65-0o571-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004863/bt2869Isup2.hkl

e-65-0o571-Isup2.hkl^{(87.5KB, hkl)}

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
N2—H2N⋯O1ⁱ	0.91 (3)	2.26 (3)	3.088 (2)	152 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST programme at the IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

Nicotinamides were involved in biological processes such as production of energy, the synthesis of fatty acids, cholesterol and steroids, signal transduction, and the maintenance of the integrity of the genome (de Souza et al., 2005). Nicotinamides play a major role in the prevention or delay of the onset of type 1 diabetes mellitus. They also have anti-oxidant, anti-inflammatory and anti-carcinogenic activities (Gdaniec et al., 1979; Cuffini et al., 2006).

The title compound is non planar molecule with a dihedral angle of 64.81 (1)° between the phenyl and pyridine ring. N—H···O intermolecular hydrogen bonds connect the molecules to one dimensional molecular chains along the b axis and forming a C(4) graph-set motif (Bernstein et al., 1995).

Experimental

Nicotinoyl chloride and aniline in tetrahydrofuran solution was stirred for 8 h at ambient temperature in the presence of a catalytic quantity of triethylamine. The reaction mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution and the resulting aqueous mixture was extracted with ethyl acetate and then concentrated under reduced pressure. Then, it was subjected to chromatography on silica, using hexane–ethyl acetate gradients. Crystals were grown from an ethanolic solution.