N-Phenylpyridine-2-carb­amide

In the title compound, C₁₂H₁₀N₂O, the dihedral angle between the pyridine ring system and the phenyl ring is 1.8 (1)°. There is an intra­molecular N—H...N hydrogen bond between the pyridine N atom and the amide NH function.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.075
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space-group Pc      ....      Pn

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.66
           From the CIF: _reflns_number_total               1162
           Count of symmetry unique reflns         1164
           Completeness (_total/calc)             99.83%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Pyridine-containing amides continue to attract considerable interest as ligands for metals (Sousa & Filgueiras, 1990; Gomes et al., 2007; Jacob & Mukherjee, 2006), building blocks in organic synthesis (Marumoto et al., 1981) and physiologically active compounds (Piatnitski & Kiselyov, 2004). As part of our studies on the synthesis and characterization of these compounds, we report here the crystal structure of the title compound.

The C7—O1 [1.223 (3) Å], N1—C7 [1.344 (3) Å] and N1—C6 [1.410 (2) Å] bond lengths indicate extensive electron delocalization in the amide linkage. The pyridyl and phenyl rings of the title compound are almost coplanar, forming a dihedral angle of 1.8 (1)°. In the crystal structure, there is an intramolecular hydrogen bond (N1—H101···N2) and no intermolecular hydrogen bonds are observed (Table 1).

The reported monoclinic space-group is in a non-standard setting (Pn, #7). There is a strong feature (h + l = 2n) in hkl data. Setting up the space group as Pc results in a β angle of 23° or 157°, respectively. Obviously such an unit-cell division is inappropriate. Therefore, the non-standard setting Pn was chosen.

Related literature

For general background, see: Sousa & Filgueiras (1990); Gomes et al. (2007); Morsali et al. (2003); Jacob & Mukherjee (2006); Marumoto et al. (1981); Piatnitski & Kiselyov (2004). For related structures, see: Qi et al. (2003); Zhang et al. (2006); Yin et al. (2007). For the synthesis, see: Chan et al. (2004).

S2. Experimental

The title compound was synthesized from pyridine-2-carboxylic acid and aniline according to the procedure of Chan et al. (2004). The crystal used for data collection was obtained by slow evaporation from a saturated ethanol/water solution at room temperature.

S3. Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with N—H = 0.86 Å, C—H = 0.93 Å, and with U_iso(H) = 1.2U_eq(parent atom).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia,1999).

Figures

Fig. 1. The molecular structure of the title compound, shown with 50% probability displacement ellipsoids.

N-Phenylpyridine-2-carbamide

Crystal data

C12H10N2O	F(000) = 208
Mr = 198.22	Dx = 1.315 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 2226 reflections
a = 5.7469 (2) Å	θ = 2.9–25.1°
b = 6.2382 (2) Å	µ = 0.09 mm^−1
c = 14.0158 (3) Å	T = 296 K
β = 94.752 (2)°	Block, colourless
V = 500.74 (3) Å^3	0.15 × 0.14 × 0.09 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer	1162 independent reflections
Radiation source: fine-focus sealed tube	1036 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 10 pixels mm^-1	θmax = 27.7°, θmin = 2.9°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −8→5
Tmin = 0.968, Tmax = 0.992	l = −18→18
5000 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0365P)^2 + 0.0548P] where P = (Fo^2 + 2Fc^2)/3
1162 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

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 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 (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.0173 (3)	0.2086 (3)	0.59409 (11)	0.0452 (4)
H101	−0.1420	0.2510	0.6183	0.054*
C8	0.1414 (3)	0.5113 (3)	0.68241 (13)	0.0435 (4)
C6	−0.0401 (3)	0.0235 (3)	0.53631 (12)	0.0412 (4)
C1	0.1246 (4)	−0.0375 (4)	0.47407 (15)	0.0509 (5)
H1	0.2570	0.0459	0.4685	0.061*
C7	0.1751 (4)	0.3270 (3)	0.61595 (15)	0.0475 (5)
C2	0.0901 (4)	−0.2230 (4)	0.42049 (16)	0.0569 (5)
H2	0.1999	−0.2635	0.3787	0.068*
N2	−0.0537 (3)	0.5139 (3)	0.72828 (12)	0.0526 (4)
C5	−0.2373 (4)	−0.1016 (3)	0.54213 (15)	0.0476 (5)
H5	−0.3507	−0.0595	0.5819	0.057*
O1	0.3656 (3)	0.2937 (3)	0.58575 (15)	0.0753 (6)
C10	0.2767 (5)	0.8384 (3)	0.75234 (17)	0.0575 (5)
H10	0.3863	0.9481	0.7597	0.069*
C11	0.0794 (4)	0.8441 (4)	0.80026 (16)	0.0612 (6)
H11	0.0523	0.9575	0.8410	0.073*
C3	−0.1044 (4)	−0.3483 (4)	0.42826 (16)	0.0553 (5)
H3	−0.1255	−0.4731	0.3923	0.066*
C12	−0.0787 (4)	0.6788 (4)	0.78711 (17)	0.0629 (6)
H12	−0.2107	0.6823	0.8213	0.076*
C9	0.3106 (4)	0.6677 (3)	0.69302 (15)	0.0516 (5)
H9	0.4451	0.6581	0.6607	0.062*
C4	−0.2676 (4)	−0.2879 (4)	0.48961 (17)	0.0553 (5)
H4	−0.3986	−0.3728	0.4956	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0458 (9)	0.0397 (9)	0.0515 (9)	−0.0007 (7)	0.0121 (7)	−0.0031 (7)
C8	0.0478 (10)	0.0408 (10)	0.0422 (10)	0.0013 (8)	0.0051 (8)	0.0021 (8)
C6	0.0458 (10)	0.0369 (10)	0.0408 (10)	0.0030 (8)	0.0042 (8)	0.0021 (8)
C1	0.0504 (11)	0.0521 (12)	0.0517 (11)	−0.0041 (10)	0.0120 (9)	−0.0028 (10)
C7	0.0497 (11)	0.0398 (11)	0.0539 (12)	−0.0030 (9)	0.0092 (9)	−0.0007 (9)
C2	0.0594 (13)	0.0609 (14)	0.0515 (12)	0.0060 (11)	0.0117 (9)	−0.0103 (10)
N2	0.0477 (9)	0.0540 (10)	0.0566 (10)	−0.0015 (8)	0.0067 (8)	−0.0096 (8)
C5	0.0464 (10)	0.0458 (11)	0.0515 (10)	−0.0004 (9)	0.0088 (8)	−0.0024 (9)
O1	0.0531 (9)	0.0669 (11)	0.1095 (15)	−0.0111 (9)	0.0283 (9)	−0.0330 (10)
C10	0.0699 (14)	0.0471 (11)	0.0550 (11)	−0.0102 (12)	0.0014 (10)	−0.0007 (11)
C11	0.0714 (16)	0.0553 (14)	0.0559 (13)	0.0065 (12)	−0.0002 (11)	−0.0156 (11)
C3	0.0652 (13)	0.0459 (11)	0.0537 (11)	0.0014 (11)	−0.0023 (10)	−0.0119 (10)
C12	0.0561 (13)	0.0705 (15)	0.0635 (14)	0.0047 (11)	0.0122 (11)	−0.0168 (12)
C9	0.0559 (11)	0.0486 (12)	0.0513 (11)	−0.0086 (10)	0.0116 (9)	−0.0018 (9)
C4	0.0550 (12)	0.0506 (13)	0.0598 (12)	−0.0070 (10)	0.0027 (10)	−0.0027 (11)

Geometric parameters (Å, º)

N1—C7	1.344 (3)	N2—C12	1.333 (3)
N1—C6	1.410 (2)	C5—C4	1.379 (3)
N1—H101	0.8600	C5—H5	0.9300
C8—N2	1.338 (2)	C10—C11	1.365 (4)
C8—C9	1.377 (3)	C10—C9	1.375 (3)
C8—C7	1.502 (3)	C10—H10	0.9300
C6—C5	1.384 (3)	C11—C12	1.377 (3)
C6—C1	1.392 (3)	C11—H11	0.9300
C1—C2	1.385 (3)	C3—C4	1.377 (3)
C1—H1	0.9300	C3—H3	0.9300
C7—O1	1.223 (3)	C12—H12	0.9300
C2—C3	1.376 (4)	C9—H9	0.9300
C2—H2	0.9300	C4—H4	0.9300
C7—N1—C6	128.07 (17)	C4—C5—H5	119.6
C7—N1—H101	116.0	C6—C5—H5	119.6
C6—N1—H101	116.0	C11—C10—C9	118.9 (2)
N2—C8—C9	123.48 (19)	C11—C10—H10	120.6
N2—C8—C7	117.62 (17)	C9—C10—H10	120.6
C9—C8—C7	118.89 (18)	C10—C11—C12	118.7 (2)
C5—C6—C1	119.06 (17)	C10—C11—H11	120.7
C5—C6—N1	117.74 (17)	C12—C11—H11	120.7
C1—C6—N1	123.19 (17)	C2—C3—C4	119.6 (2)
C2—C1—C6	119.57 (19)	C2—C3—H3	120.2
C2—C1—H1	120.2	C4—C3—H3	120.2
C6—C1—H1	120.2	N2—C12—C11	123.8 (2)
O1—C7—N1	124.81 (19)	N2—C12—H12	118.1
O1—C7—C8	120.61 (18)	C11—C12—H12	118.1
N1—C7—C8	114.58 (18)	C10—C9—C8	118.7 (2)
C3—C2—C1	120.8 (2)	C10—C9—H9	120.6
C3—C2—H2	119.6	C8—C9—H9	120.6
C1—C2—H2	119.6	C3—C4—C5	120.1 (2)
C12—N2—C8	116.38 (18)	C3—C4—H4	119.9
C4—C5—C6	120.77 (19)	C5—C4—H4	119.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···N2	0.86	2.28	2.697 (2)	110