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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o371.
Published online 2010 January 16. doi:  10.1107/S160053680905586X
PMCID: PMC2979916

N-(4-Methyl-2-pyrid­yl)-p-toluidine

Abstract

In the title compound, C13H14N2, the dihedral angle between the aromatic rings is 48.1 (1)° and the bridging C—N—C bond angle is 127.24 (12)°. In the crystal, intermolecular N—H(...)N hydrogen bonding about a center of inversion generates a hydrogen-bonded dimer.

Related literature

For the structure of N-(2-pyrid­yl)-4-toluidine, see: Fairuz et al. (2008 [triangle]).

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Object name is e-66-0o371-scheme1.jpg

Experimental

Crystal data

  • C13H14N2
  • M r = 198.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o371-efi1.jpg
  • a = 10.9385 (11) Å
  • b = 7.5708 (8) Å
  • c = 13.4372 (14) Å
  • β = 95.246 (2)°
  • V = 1108.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 295 K
  • 0.45 × 0.40 × 0.30 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 6758 measured reflections
  • 2528 independent reflections
  • 1797 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.142
  • S = 1.05
  • 2528 reflections
  • 143 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905586X/xu2710sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905586X/xu2710Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant No. RG027/09AFR, PS374/09 A) for supporting this study.

supplementary crystallographic information

Experimental

2-Chloro-4-methylpyridine (1 ml, 0.01 mol) and p-toluidine (1.2 g, 0.01 mol) were heated for 4 h. The product was dissolved in water and the solution extracted with ether. The ether extract was dried over sodium sulfate. Evaporation of the solvent gave large blocks of dark brown crystals. The crystals, when the outer parts were removed, were colorless.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.86±0.01 Å; its temperature factor was refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the hydrogen-bonded C13H14N2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

Crystal data

C13H14N2F(000) = 424
Mr = 198.26Dx = 1.188 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2289 reflections
a = 10.9385 (11) Åθ = 2.5–28.1°
b = 7.5708 (8) ŵ = 0.07 mm1
c = 13.4372 (14) ÅT = 295 K
β = 95.246 (2)°Irregular block, colorless
V = 1108.1 (2) Å30.45 × 0.40 × 0.30 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer1797 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 27.5°, θmin = 2.3°
ω scansh = −14→13
6758 measured reflectionsk = −9→9
2528 independent reflectionsl = −14→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142w = 1/[σ2(Fo2) + (0.0692P)2 + 0.1529P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2528 reflectionsΔρmax = 0.17 e Å3
143 parametersΔρmin = −0.13 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.044 (6)

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

xyzUiso*/Ueq
N10.51269 (11)0.54344 (19)0.64065 (9)0.0571 (4)
H10.4682 (13)0.546 (2)0.5832 (8)0.063 (5)*
N20.66732 (12)0.46482 (18)0.54571 (9)0.0554 (4)
C10.78715 (15)0.4383 (2)0.53779 (12)0.0642 (5)
H1A0.81070.40720.47540.077*
C20.87740 (14)0.4535 (2)0.61487 (13)0.0619 (4)
H20.95880.42880.60520.074*
C30.84502 (13)0.50645 (19)0.70755 (11)0.0490 (4)
C40.72299 (13)0.53940 (19)0.71698 (11)0.0471 (3)
H40.69850.57880.77760.056*
C50.63566 (13)0.51384 (18)0.63552 (10)0.0458 (3)
C60.93890 (14)0.5264 (2)0.79563 (12)0.0607 (4)
H6A0.91680.62390.83600.091*
H6B1.01800.54790.77250.091*
H6C0.94180.42010.83470.091*
C70.45006 (12)0.55349 (19)0.72722 (10)0.0447 (3)
C80.35038 (12)0.6665 (2)0.72803 (11)0.0516 (4)
H80.32940.73850.67310.062*
C90.28208 (13)0.6735 (2)0.80914 (11)0.0547 (4)
H90.21530.74980.80770.066*
C100.31070 (13)0.5694 (2)0.89293 (11)0.0526 (4)
C110.41089 (13)0.4573 (2)0.89151 (11)0.0502 (4)
H110.43220.38600.94670.060*
C120.47974 (13)0.44843 (19)0.81091 (10)0.0477 (4)
H120.54640.37190.81240.057*
C130.23520 (17)0.5750 (3)0.98106 (13)0.0757 (5)
H13A0.16310.64520.96460.113*
H13B0.28290.62621.03730.113*
H13C0.21150.45720.99740.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0418 (7)0.0866 (10)0.0424 (7)0.0084 (6)0.0001 (5)0.0006 (6)
N20.0492 (7)0.0675 (8)0.0496 (7)0.0037 (6)0.0048 (5)−0.0037 (6)
C10.0536 (9)0.0824 (12)0.0583 (9)0.0073 (8)0.0136 (7)−0.0093 (8)
C20.0426 (8)0.0744 (11)0.0698 (10)0.0060 (7)0.0104 (7)−0.0040 (8)
C30.0433 (8)0.0435 (8)0.0599 (9)−0.0004 (6)0.0025 (6)0.0045 (6)
C40.0439 (7)0.0494 (8)0.0479 (7)0.0008 (6)0.0049 (6)−0.0010 (6)
C50.0427 (7)0.0476 (8)0.0471 (7)0.0022 (6)0.0049 (6)0.0029 (6)
C60.0435 (8)0.0664 (10)0.0706 (10)−0.0005 (7)−0.0032 (7)0.0044 (8)
C70.0363 (7)0.0533 (8)0.0434 (7)−0.0015 (6)−0.0023 (5)−0.0024 (6)
C80.0424 (7)0.0570 (9)0.0542 (8)0.0033 (6)−0.0022 (6)0.0070 (7)
C90.0411 (7)0.0585 (9)0.0643 (9)0.0052 (6)0.0031 (6)−0.0040 (7)
C100.0452 (8)0.0625 (9)0.0500 (8)−0.0080 (7)0.0034 (6)−0.0102 (7)
C110.0479 (8)0.0559 (9)0.0450 (7)−0.0082 (6)−0.0047 (6)0.0031 (6)
C120.0408 (7)0.0497 (8)0.0512 (8)0.0021 (6)−0.0036 (6)−0.0022 (6)
C130.0698 (11)0.0969 (14)0.0623 (10)−0.0047 (10)0.0172 (8)−0.0109 (10)

Geometric parameters (Å, °)

N1—C51.3716 (18)C6—H6C0.9600
N1—C71.4051 (18)C7—C81.3867 (19)
N1—H10.875 (9)C7—C121.391 (2)
N2—C11.340 (2)C8—C91.378 (2)
N2—C51.3380 (18)C8—H80.9300
C1—C21.369 (2)C9—C101.386 (2)
C1—H1A0.9300C9—H90.9300
C2—C31.385 (2)C10—C111.388 (2)
C2—H20.9300C10—C131.505 (2)
C3—C41.375 (2)C11—C121.376 (2)
C3—C61.502 (2)C11—H110.9300
C4—C51.399 (2)C12—H120.9300
C4—H40.9300C13—H13A0.9600
C6—H6A0.9600C13—H13B0.9600
C6—H6B0.9600C13—H13C0.9600
C5—N1—C7127.24 (12)C8—C7—C12118.16 (13)
C5—N1—H1115.4 (11)C8—C7—N1118.89 (13)
C7—N1—H1117.1 (11)C12—C7—N1122.87 (13)
C1—N2—C5116.68 (13)C9—C8—C7120.90 (13)
N2—C1—C2124.77 (15)C9—C8—H8119.5
N2—C1—H1A117.6C7—C8—H8119.5
C2—C1—H1A117.6C8—C9—C10121.47 (14)
C1—C2—C3118.61 (14)C8—C9—H9119.3
C1—C2—H2120.7C10—C9—H9119.3
C3—C2—H2120.7C9—C10—C11117.16 (14)
C4—C3—C2117.75 (14)C9—C10—C13121.57 (15)
C4—C3—C6120.58 (14)C11—C10—C13121.26 (15)
C2—C3—C6121.67 (14)C12—C11—C10122.03 (14)
C3—C4—C5120.13 (13)C12—C11—H11119.0
C3—C4—H4119.9C10—C11—H11119.0
C5—C4—H4119.9C11—C12—C7120.27 (13)
N2—C5—N1115.25 (12)C11—C12—H12119.9
N2—C5—C4121.97 (13)C7—C12—H12119.9
N1—C5—C4122.73 (13)C10—C13—H13A109.5
C3—C6—H6A109.5C10—C13—H13B109.5
C3—C6—H6B109.5H13A—C13—H13B109.5
H6A—C6—H6B109.5C10—C13—H13C109.5
C3—C6—H6C109.5H13A—C13—H13C109.5
H6A—C6—H6C109.5H13B—C13—H13C109.5
H6B—C6—H6C109.5
C5—N2—C1—C21.7 (3)C5—N1—C7—C8146.94 (15)
N2—C1—C2—C3−2.5 (3)C5—N1—C7—C12−36.3 (2)
C1—C2—C3—C40.6 (2)C12—C7—C8—C9−0.5 (2)
C1—C2—C3—C6−179.91 (16)N1—C7—C8—C9176.39 (13)
C2—C3—C4—C52.0 (2)C7—C8—C9—C100.5 (2)
C6—C3—C4—C5−177.51 (13)C8—C9—C10—C11−0.2 (2)
C1—N2—C5—N1178.72 (14)C8—C9—C10—C13−179.16 (15)
C1—N2—C5—C41.1 (2)C9—C10—C11—C120.0 (2)
C7—N1—C5—N2163.28 (14)C13—C10—C11—C12178.95 (14)
C7—N1—C5—C4−19.1 (2)C10—C11—C12—C70.0 (2)
C3—C4—C5—N2−3.0 (2)C8—C7—C12—C110.3 (2)
C3—C4—C5—N1179.59 (14)N1—C7—C12—C11−176.47 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.87 (1)2.18 (1)3.041 (2)170 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2710).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fairuz, Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2441. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography