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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2440.
Published online 2008 November 26. doi:  10.1107/S160053680803729X
PMCID: PMC2960145

N-(Pyrazin-2-yl)-4-toluidine

Abstract

The two aromatic systems in the title compound, C11H11N3, are inclined by 19.1 (1)°, whilst the angle at the central amino N atom is 130.3 (2)°. The amino group forms a hydrogen bond to the pyrazine N-4 atom of an adjacent mol­ecule, forming a chain motif.

Related literature

For the structure of amino­pyrazine, see: Chao et al. (1976 [triangle]) and for that of N-(pyrazin-2-yl)-2-nitro­aniline; see: Parsons et al. (2006 [triangle]). For two monoclinic modifications of N-(pyrazin-2-yl)aniline, see: Abdullah & Ng (2008 [triangle]); Wan Saffiee et al. (2008 [triangle]).

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Object name is e-64-o2440-scheme1.jpg

Experimental

Crystal data

  • C11H11N3
  • M r = 185.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2440-efi1.jpg
  • a = 21.7179 (7) Å
  • b = 7.5323 (3) Å
  • c = 12.0073 (5) Å
  • β = 105.790 (3)°
  • V = 1890.1 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 (2) K
  • 0.30 × 0.20 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 6057 measured reflections
  • 2165 independent reflections
  • 1437 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.135
  • S = 1.03
  • 2165 reflections
  • 132 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803729X/sg2277sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803729X/sg2277Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study (grant No. FS 358/2008 A).

supplementary crystallographic information

Experimental

Chloropyrazine (1 ml, 1.1 mmol) and 4-toluidine (1.2 g, 1.1 mmol) were heated at 423–433 K for 3 h. The solid was dissolved in water. The compound was extracted with ether. The ether extract was dried over sodium sulfate; evaporation of the solvent gave colorless crystals among some unidentified dark brown materials.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 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 0.88±0.01 Å.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C11H11N3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H11N3F000 = 784
Mr = 185.23Dx = 1.302 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1368 reflections
a = 21.7179 (7) Åθ = 2.9–27.2º
b = 7.5323 (3) ŵ = 0.08 mm1
c = 12.0073 (5) ÅT = 100 (2) K
β = 105.790 (3)ºPrism, colorless
V = 1890.1 (1) Å30.30 × 0.20 × 0.05 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer1437 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.0º
ω scansh = −28→28
Absorption correction: Nonek = −9→9
6057 measured reflectionsl = −15→15
2165 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.0652P)2 + 0.9346P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2165 reflectionsΔρmax = 0.27 e Å3
132 parametersΔρmin = −0.26 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
N10.31486 (7)0.7286 (2)0.14663 (14)0.0223 (4)
H10.2746 (10)0.754 (3)0.1433 (17)0.025 (5)*
N20.39338 (7)0.5068 (2)0.20972 (13)0.0215 (4)
N30.30867 (7)0.3328 (2)0.31234 (14)0.0240 (4)
C10.34916 (8)0.8610 (2)0.10751 (15)0.0209 (4)
C20.31332 (8)0.9994 (2)0.04370 (15)0.0225 (4)
H20.26800.99770.02740.027*
C30.34299 (9)1.1385 (2)0.00420 (15)0.0243 (4)
H30.31761.2305−0.03960.029*
C40.40936 (9)1.1472 (2)0.02707 (15)0.0231 (4)
C50.44431 (8)1.0095 (2)0.09091 (15)0.0226 (4)
H50.48971.01270.10810.027*
C60.41565 (8)0.8672 (2)0.13069 (15)0.0222 (4)
H60.44120.77450.17340.027*
C70.44137 (10)1.3010 (3)−0.01539 (18)0.0302 (5)
H7A0.48761.29580.02030.045*
H7B0.42441.41290.00560.045*
H7C0.43281.2941−0.09970.045*
C80.33543 (8)0.5719 (2)0.20318 (15)0.0201 (4)
C90.29286 (8)0.4818 (2)0.25360 (16)0.0231 (4)
H90.25140.52980.24500.028*
C100.36764 (8)0.2678 (2)0.32060 (16)0.0231 (4)
H100.38130.16160.36280.028*
C110.40806 (9)0.3538 (2)0.26845 (16)0.0235 (4)
H110.44870.30220.27420.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0217 (8)0.0194 (8)0.0284 (9)0.0007 (6)0.0110 (7)0.0031 (7)
N20.0249 (8)0.0191 (8)0.0223 (8)0.0013 (6)0.0095 (6)−0.0011 (6)
N30.0254 (8)0.0213 (8)0.0262 (9)−0.0016 (6)0.0087 (7)0.0019 (7)
C10.0275 (9)0.0177 (9)0.0191 (9)−0.0009 (7)0.0089 (7)−0.0013 (7)
C20.0240 (9)0.0224 (10)0.0214 (10)0.0019 (8)0.0067 (7)−0.0018 (8)
C30.0344 (10)0.0191 (9)0.0194 (10)0.0024 (8)0.0072 (8)0.0004 (7)
C40.0316 (10)0.0193 (9)0.0200 (9)−0.0032 (8)0.0096 (8)−0.0008 (7)
C50.0252 (9)0.0222 (10)0.0221 (10)−0.0018 (8)0.0093 (8)−0.0018 (8)
C60.0261 (9)0.0207 (9)0.0204 (9)0.0004 (7)0.0071 (7)0.0004 (7)
C70.0390 (11)0.0250 (11)0.0287 (11)−0.0033 (9)0.0128 (9)0.0045 (8)
C80.0237 (9)0.0196 (9)0.0177 (9)−0.0013 (7)0.0065 (7)−0.0023 (7)
C90.0222 (9)0.0211 (9)0.0267 (10)0.0003 (7)0.0079 (8)0.0002 (8)
C100.0275 (9)0.0187 (9)0.0237 (10)0.0022 (7)0.0077 (8)0.0003 (8)
C110.0264 (9)0.0211 (10)0.0238 (10)0.0020 (8)0.0080 (8)−0.0020 (8)

Geometric parameters (Å, °)

N1—C81.374 (2)C4—C51.386 (3)
N1—C11.401 (2)C4—C71.509 (3)
N1—H10.89 (2)C5—C61.388 (2)
N2—C81.333 (2)C5—H50.9500
N2—C111.344 (2)C6—H60.9500
N3—C91.320 (2)C7—H7A0.9800
N3—C101.349 (2)C7—H7B0.9800
C1—C61.395 (2)C7—H7C0.9800
C1—C21.398 (2)C8—C91.410 (2)
C2—C31.380 (3)C9—H90.9500
C2—H20.9500C10—C111.372 (3)
C3—C41.393 (3)C10—H100.9500
C3—H30.9500C11—H110.9500
C8—N1—C1130.28 (15)C5—C6—H6120.2
C8—N1—H1113.3 (13)C1—C6—H6120.2
C1—N1—H1115.9 (14)C4—C7—H7A109.5
C8—N2—C11115.60 (15)C4—C7—H7B109.5
C9—N3—C10116.84 (15)H7A—C7—H7B109.5
C6—C1—C2118.44 (16)C4—C7—H7C109.5
C6—C1—N1124.95 (16)H7A—C7—H7C109.5
C2—C1—N1116.58 (15)H7B—C7—H7C109.5
C3—C2—C1120.81 (16)N2—C8—N1121.33 (16)
C3—C2—H2119.6N2—C8—C9121.10 (16)
C1—C2—H2119.6N1—C8—C9117.57 (15)
C2—C3—C4121.50 (17)N3—C9—C8122.23 (16)
C2—C3—H3119.3N3—C9—H9118.9
C4—C3—H3119.3C8—C9—H9118.9
C5—C4—C3117.08 (16)N3—C10—C11120.51 (17)
C5—C4—C7121.84 (16)N3—C10—H10119.7
C3—C4—C7121.08 (17)C11—C10—H10119.7
C4—C5—C6122.59 (16)N2—C11—C10123.68 (17)
C4—C5—H5118.7N2—C11—H11118.2
C6—C5—H5118.7C10—C11—H11118.2
C5—C6—C1119.58 (17)
C8—N1—C1—C6−7.4 (3)N1—C1—C6—C5−177.39 (17)
C8—N1—C1—C2174.81 (17)C11—N2—C8—N1179.29 (16)
C6—C1—C2—C30.2 (3)C11—N2—C8—C9−1.1 (2)
N1—C1—C2—C3178.22 (16)C1—N1—C8—N2−13.4 (3)
C1—C2—C3—C4−0.6 (3)C1—N1—C8—C9166.96 (17)
C2—C3—C4—C50.2 (3)C10—N3—C9—C8−1.1 (3)
C2—C3—C4—C7−179.30 (17)N2—C8—C9—N32.1 (3)
C3—C4—C5—C60.4 (3)N1—C8—C9—N3−178.20 (16)
C7—C4—C5—C6179.96 (17)C9—N3—C10—C11−0.8 (3)
C4—C5—C6—C1−0.7 (3)C8—N2—C11—C10−0.8 (3)
C2—C1—C6—C50.4 (3)N3—C10—C11—N21.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N3i0.89 (2)2.10 (2)2.963 (2)163 (2)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2277).

References

  • Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2106. [PMC free article] [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chao, M., Schempp, E. & Rosenstein, R. D. (1976). Acta Cryst. B32, 288–290.
  • Parsons, S., Wharton, S., McNab, H., Parkin, A. & Johnstone, R. (2006). Private communcation (refcode SEMSAF 610410). CCDC, Cambridge, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2105. [PMC free article] [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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