N-Phenyl­nicotinamide

Roopan, S.M.; Hathwar, V.R.; Kumar, A.S.; Malathi, N.; Khan, F.N.

doi:10.1107/S1600536809004863

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o571

doi:10.1107/S1600536809004863

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N-Phenylnicotinamide

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

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 9 February 2009; accepted 10 February 2009; online 21 February 2009)

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, C 2/c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 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

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)
Symmetry code: (i) x, y+1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound shown with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing diagram of the title compound. The dotted lines indicate N—H···O intermolecular hydrogen bonds forming molecular chains along the b axis. All H atoms not involved in hydrogen bonds have been omitted for clarity.

N-Phenylnicotinamide top

Crystal data top

C₁₂H₁₀N₂O	F(000) = 832
M_r = 198.22	D_x = 1.355 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 829 reflections
a = 18.732 (4) Å	θ = 2.0–24.4°
b = 5.2766 (11) Å	µ = 0.09 mm⁻¹
c = 20.248 (4) Å	T = 290 K
β = 103.746 (4)°	Cylindrical, colourless
V = 1944.0 (7) Å³	0.23 × 0.15 × 0.11 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	1813 independent reflections
Radiation source: fine-focus sealed tube	1287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→21
T_min = 0.917, T_max = 0.990	k = −6→6
6923 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0469P)² + 0.7301P] where P = (F_o² + 2F_c²)/3
1813 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₂H₁₀N₂O	V = 1944.0 (7) Å³
M_r = 198.22	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.732 (4) Å	µ = 0.09 mm⁻¹
b = 5.2766 (11) Å	T = 290 K
c = 20.248 (4) Å	0.23 × 0.15 × 0.11 mm
β = 103.746 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1813 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1287 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.990	R_int = 0.039
6923 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
1813 reflections	Δρ_min = −0.21 e Å⁻³
140 parameters

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.70535 (8)	0.6222 (2)	0.07461 (7)	0.0535 (5)
N1	0.50992 (9)	0.7693 (3)	−0.06750 (9)	0.0510 (5)
N2	0.72283 (9)	1.0437 (3)	0.09527 (8)	0.0403 (4)
H2N	0.7016 (12)	1.196 (5)	0.0809 (11)	0.075 (8)*
C1	0.78193 (10)	1.0299 (3)	0.15450 (9)	0.0343 (5)
C2	0.83422 (11)	0.8400 (4)	0.16449 (10)	0.0430 (5)
H2	0.8316	0.7127	0.1322	0.052*
C3	0.89028 (11)	0.8406 (4)	0.22253 (10)	0.0480 (6)
H3	0.9255	0.7128	0.2292	0.058*
C4	0.89503 (12)	1.0271 (4)	0.27086 (11)	0.0480 (6)
H4	0.9327	1.0250	0.3102	0.058*
C5	0.84308 (11)	1.2170 (4)	0.26008 (10)	0.0465 (6)
H5	0.8460	1.3451	0.2922	0.056*
C6	0.78691 (11)	1.2189 (4)	0.20234 (9)	0.0403 (5)
H6	0.7522	1.3482	0.1955	0.048*
C7	0.68817 (11)	0.8434 (3)	0.05987 (9)	0.0380 (5)
C8	0.62589 (10)	0.9088 (3)	0.00086 (9)	0.0342 (5)
C9	0.62425 (11)	1.1201 (3)	−0.03994 (9)	0.0392 (5)
H9	0.6620	1.2387	−0.0303	0.047*
C10	0.56564 (11)	1.1513 (4)	−0.09499 (10)	0.0458 (5)
H10	0.5633	1.2900	−0.1238	0.055*
C11	0.51068 (12)	0.9730 (4)	−0.10646 (10)	0.0489 (6)
H11	0.4714	0.9955	−0.1439	0.059*
C12	0.56755 (11)	0.7414 (4)	−0.01519 (10)	0.0427 (5)
H12	0.5687	0.6000	0.0125	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0640 (10)	0.0257 (7)	0.0580 (9)	0.0019 (7)	−0.0108 (8)	0.0037 (6)
N1	0.0437 (11)	0.0428 (10)	0.0586 (12)	−0.0019 (8)	−0.0036 (10)	−0.0025 (9)
N2	0.0454 (11)	0.0298 (9)	0.0410 (10)	0.0004 (8)	0.0012 (8)	−0.0012 (7)
C1	0.0331 (11)	0.0339 (10)	0.0336 (10)	−0.0032 (8)	0.0036 (9)	0.0021 (8)
C2	0.0419 (12)	0.0383 (11)	0.0455 (12)	−0.0003 (9)	0.0038 (10)	−0.0076 (9)
C3	0.0403 (12)	0.0385 (11)	0.0590 (14)	0.0078 (9)	−0.0006 (11)	0.0027 (10)
C4	0.0416 (13)	0.0482 (12)	0.0454 (12)	−0.0047 (10)	−0.0070 (10)	0.0019 (10)
C5	0.0513 (14)	0.0401 (12)	0.0437 (12)	−0.0049 (10)	0.0028 (11)	−0.0094 (9)
C6	0.0403 (12)	0.0344 (10)	0.0431 (12)	0.0012 (9)	0.0036 (10)	−0.0019 (9)
C7	0.0433 (12)	0.0308 (10)	0.0392 (11)	−0.0019 (9)	0.0083 (9)	−0.0010 (8)
C8	0.0347 (11)	0.0349 (10)	0.0318 (10)	0.0022 (9)	0.0052 (9)	−0.0020 (8)
C9	0.0383 (11)	0.0364 (10)	0.0403 (11)	−0.0026 (9)	0.0039 (10)	−0.0027 (9)
C10	0.0512 (14)	0.0365 (11)	0.0460 (12)	0.0057 (10)	0.0042 (11)	0.0048 (9)
C11	0.0449 (13)	0.0468 (12)	0.0456 (12)	0.0093 (10)	−0.0076 (10)	−0.0033 (10)
C12	0.0441 (13)	0.0342 (11)	0.0464 (12)	−0.0007 (9)	0.0038 (11)	0.0021 (9)

Geometric parameters (Å, º) top

O1—C7	1.228 (2)	C4—H4	0.9300
N1—C12	1.329 (2)	C5—C6	1.375 (3)
N1—C11	1.335 (3)	C5—H5	0.9300
N2—C7	1.354 (2)	C6—H6	0.9300
N2—C1	1.428 (2)	C7—C8	1.498 (3)
N2—H2N	0.91 (2)	C8—C12	1.382 (3)
C1—C6	1.378 (3)	C8—C9	1.384 (2)
C1—C2	1.382 (3)	C9—C10	1.376 (3)
C2—C3	1.377 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.373 (3)
C3—C4	1.376 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.378 (3)	C12—H12	0.9300

C12—N1—C11	116.06 (18)	C5—C6—H6	119.9
C7—N2—C1	125.70 (17)	C1—C6—H6	119.9
C7—N2—H2N	113.6 (14)	O1—C7—N2	123.27 (18)
C1—N2—H2N	120.3 (14)	O1—C7—C8	121.46 (17)
C6—C1—C2	119.65 (17)	N2—C7—C8	115.27 (16)
C6—C1—N2	117.58 (17)	C12—C8—C9	118.05 (17)
C2—C1—N2	122.76 (17)	C12—C8—C7	117.55 (17)
C3—C2—C1	119.56 (18)	C9—C8—C7	124.36 (17)
C3—C2—H2	120.2	C10—C9—C8	118.71 (18)
C1—C2—H2	120.2	C10—C9—H9	120.6
C4—C3—C2	121.05 (19)	C8—C9—H9	120.6
C4—C3—H3	119.5	C11—C10—C9	118.47 (19)
C2—C3—H3	119.5	C11—C10—H10	120.8
C3—C4—C5	118.93 (19)	C9—C10—H10	120.8
C3—C4—H4	120.5	N1—C11—C10	124.37 (19)
C5—C4—H4	120.5	N1—C11—H11	117.8
C6—C5—C4	120.61 (19)	C10—C11—H11	117.8
C6—C5—H5	119.7	N1—C12—C8	124.33 (18)
C4—C5—H5	119.7	N1—C12—H12	117.8
C5—C6—C1	120.20 (18)	C8—C12—H12	117.8

C7—N2—C1—C6	−148.13 (19)	O1—C7—C8—C12	31.6 (3)
C7—N2—C1—C2	33.3 (3)	N2—C7—C8—C12	−147.87 (18)
C6—C1—C2—C3	0.7 (3)	O1—C7—C8—C9	−145.9 (2)
N2—C1—C2—C3	179.18 (18)	N2—C7—C8—C9	34.6 (3)
C1—C2—C3—C4	0.1 (3)	C12—C8—C9—C10	−1.2 (3)
C2—C3—C4—C5	−0.8 (3)	C7—C8—C9—C10	176.34 (18)
C3—C4—C5—C6	0.7 (3)	C8—C9—C10—C11	1.0 (3)
C4—C5—C6—C1	0.1 (3)	C12—N1—C11—C10	−1.0 (3)
C2—C1—C6—C5	−0.8 (3)	C9—C10—C11—N1	0.2 (3)
N2—C1—C6—C5	−179.35 (17)	C11—N1—C12—C8	0.8 (3)
C1—N2—C7—O1	−1.5 (3)	C9—C8—C12—N1	0.3 (3)
C1—N2—C7—C8	177.91 (17)	C7—C8—C12—N1	−177.39 (19)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O
M_r	198.22
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	290
a, b, c (Å)	18.732 (4), 5.2766 (11), 20.248 (4)
β (°)	103.746 (4)
V (Å³)	1944.0 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.917, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6923, 1813, 1287
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.112, 1.03
No. of reflections	1813
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS90 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1999) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) x, y+1, z.

Acknowledgements

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.

References

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