N-Phenyl-nicotinamide.

In the title compound, C(12)H(10)N(2)O, the dihedral angle between the phenyl and pyridine rings is 64.81 (1)°. Inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules 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 = 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

Δρmax = 0.19 e Å−3

Δρmin = −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.

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

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

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

C12H10N2O	F(000) = 832
Mr = 198.22	Dx = 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

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

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(Fo2) + (0.0469P)2 + 0.7301P] where P = (Fo2 + 2Fc2)/3
1813 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .