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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2437.
Published online 2008 November 26. doi:  10.1107/S1600536808038658
PMCID: PMC2959926

4-Chloro-N-(2-pyrid­yl)aniline

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C11H9ClN2, with dihedral angles of 41.84 (12) and 49.24 (12)° between the aromatic ring planes. The two mol­ecules form a dimer via a pair of N—H(...)N hydrogen bonds.

Related literature

For the structures of the two 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-o2437-scheme1.jpg

Experimental

Crystal data

  • C11H9ClN2
  • M r = 204.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2437-efi1.jpg
  • a = 15.5096 (4) Å
  • b = 7.5519 (2) Å
  • c = 17.6846 (4) Å
  • β = 106.284 (2)°
  • V = 1988.25 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 296 (2) K
  • 0.42 × 0.06 × 0.03 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.870, T max = 0.990
  • 18472 measured reflections
  • 4565 independent reflections
  • 2369 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.137
  • S = 1.00
  • 4565 reflections
  • 261 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.24 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/S1600536808038658/hb2855sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038658/hb2855Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study (grant No. PS205/2008 A).

supplementary crystallographic information

Comment

For related structures, see: Abdullah & Ng (2008); Wan Saffiee et al. (2008). For the molecular structure of the title compound, (I), see Fig. 1. For hydrogen bond data, see Table 1.

Experimental

2-Chloropyrazine (0.11 g, 0.1 mmol) and 4-chloroaniline (0.13 g, 0.1 mmol) were heated at 423–433 K for 5 h. The mixture was cooled and dissolved in water. The solution was extracted with ether. The ether extract was dried over sodium sulfate and the solvent evaporated to yield a dark brown compound. Colourless rods of (I) were separated manually.

Refinement

The carbon-bound H-atoms were placed in calculated positions (C—H = 0.95 Å) and refined as riding with U(H) = 1.2U(C). The amino H-atoms were located in a difference map, and were refined with a distance restraint of N–H = 0.88±0.01 Å.

Figures

Fig. 1.
The molecular structure of (I) drawn at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H9ClN2F000 = 848
Mr = 204.65Dx = 1.367 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2114 reflections
a = 15.5096 (4) Åθ = 2.4–21.4º
b = 7.5519 (2) ŵ = 0.34 mm1
c = 17.6846 (4) ÅT = 296 (2) K
β = 106.284 (2)ºRod, colourless
V = 1988.25 (9) Å30.42 × 0.06 × 0.03 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer4565 independent reflections
Radiation source: fine-focus sealed tube2369 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −20→20
Tmin = 0.870, Tmax = 0.990k = −9→9
18472 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137  w = 1/[σ2(Fo2) + (0.0544P)2 + 0.3184P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4565 reflectionsΔρmax = 0.15 e Å3
261 parametersΔρmin = −0.24 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
Cl10.67109 (6)0.86166 (11)0.13818 (4)0.0915 (3)
Cl20.52605 (6)0.65436 (13)0.94056 (4)0.1027 (3)
N10.67429 (13)0.7765 (3)0.47124 (11)0.0625 (5)
H10.6219 (9)0.782 (3)0.4794 (14)0.074 (8)*
N20.72018 (12)0.7057 (3)0.60159 (11)0.0625 (5)
N30.52408 (13)0.6934 (3)0.60693 (11)0.0651 (6)
H30.5772 (9)0.691 (3)0.6004 (13)0.064 (7)*
N40.48220 (12)0.7816 (3)0.47849 (11)0.0634 (5)
C10.78370 (17)0.6465 (4)0.66437 (14)0.0710 (7)
H1A0.76880.63750.71160.085*
C20.86856 (17)0.5984 (4)0.66472 (15)0.0743 (8)
H20.90990.55710.71020.089*
C30.89013 (16)0.6137 (3)0.59455 (15)0.0693 (7)
H3A0.94730.58280.59210.083*
C40.82822 (15)0.6738 (3)0.52878 (14)0.0614 (6)
H40.84250.68420.48130.074*
C50.74264 (14)0.7197 (3)0.53411 (13)0.0528 (6)
C60.67699 (14)0.7960 (3)0.39292 (12)0.0517 (5)
C70.74402 (15)0.8895 (3)0.37290 (14)0.0626 (6)
H70.79020.94070.41220.075*
C80.74268 (16)0.9074 (3)0.29468 (15)0.0648 (7)
H80.78890.96700.28150.078*
C90.67292 (17)0.8368 (3)0.23664 (14)0.0590 (6)
C100.60499 (15)0.7467 (3)0.25551 (13)0.0571 (6)
H100.55760.70030.21600.069*
C110.60754 (14)0.7255 (3)0.33346 (13)0.0532 (6)
H110.56190.66300.34630.064*
C120.41850 (17)0.8195 (4)0.41237 (14)0.0756 (8)
H120.43680.85690.36920.091*
C130.32900 (18)0.8074 (4)0.40351 (15)0.0787 (8)
H130.28730.83890.35650.094*
C140.30224 (16)0.7468 (4)0.46686 (15)0.0747 (8)
H140.24150.73350.46280.090*
C150.36502 (15)0.7066 (3)0.53537 (14)0.0654 (7)
H150.34780.66470.57840.078*
C160.45526 (14)0.7290 (3)0.54015 (13)0.0546 (6)
C170.52001 (13)0.6854 (3)0.68456 (12)0.0504 (5)
C180.45807 (15)0.7767 (3)0.71257 (13)0.0573 (6)
H180.41510.84700.67840.069*
C190.45919 (16)0.7647 (3)0.79053 (14)0.0614 (6)
H190.41610.82380.80840.074*
C200.52424 (16)0.6652 (3)0.84200 (13)0.0601 (6)
C210.58698 (15)0.5743 (3)0.81581 (13)0.0592 (6)
H210.63080.50710.85070.071*
C220.58459 (14)0.5833 (3)0.73756 (13)0.0559 (6)
H220.62660.52050.71970.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1128 (6)0.1099 (6)0.0642 (4)0.0274 (5)0.0455 (4)0.0168 (4)
Cl20.1127 (6)0.1427 (8)0.0617 (4)0.0110 (5)0.0395 (4)0.0276 (4)
N10.0442 (11)0.0929 (16)0.0500 (11)0.0058 (11)0.0123 (10)0.0067 (10)
N20.0496 (11)0.0902 (15)0.0470 (11)−0.0002 (10)0.0125 (9)−0.0015 (10)
N30.0437 (11)0.1038 (17)0.0470 (11)0.0070 (11)0.0112 (9)0.0061 (10)
N40.0528 (11)0.0867 (15)0.0499 (12)0.0078 (10)0.0132 (10)0.0019 (10)
C10.0581 (15)0.104 (2)0.0467 (14)−0.0025 (15)0.0082 (12)0.0000 (13)
C20.0530 (15)0.101 (2)0.0594 (16)0.0018 (14)0.0003 (12)0.0038 (14)
C30.0453 (13)0.0847 (19)0.0717 (17)0.0065 (13)0.0062 (13)−0.0064 (14)
C40.0501 (13)0.0802 (18)0.0535 (14)0.0011 (12)0.0136 (11)−0.0050 (12)
C50.0437 (12)0.0622 (14)0.0499 (13)−0.0034 (11)0.0086 (11)−0.0051 (11)
C60.0444 (12)0.0614 (14)0.0502 (13)0.0000 (11)0.0146 (10)0.0030 (11)
C70.0509 (14)0.0699 (16)0.0649 (15)−0.0099 (12)0.0126 (12)0.0014 (12)
C80.0565 (14)0.0664 (16)0.0782 (17)−0.0024 (12)0.0301 (13)0.0124 (13)
C90.0627 (15)0.0628 (16)0.0556 (14)0.0137 (12)0.0231 (12)0.0072 (11)
C100.0489 (13)0.0655 (16)0.0547 (14)0.0020 (11)0.0107 (11)−0.0056 (11)
C110.0438 (12)0.0596 (14)0.0575 (14)−0.0017 (11)0.0162 (11)0.0015 (11)
C120.0645 (17)0.111 (2)0.0505 (15)0.0178 (15)0.0148 (13)0.0093 (14)
C130.0578 (16)0.119 (2)0.0516 (15)0.0208 (16)0.0031 (13)0.0020 (15)
C140.0464 (14)0.102 (2)0.0685 (17)0.0002 (14)0.0049 (13)−0.0065 (15)
C150.0488 (13)0.0883 (18)0.0560 (14)−0.0067 (13)0.0097 (11)0.0019 (13)
C160.0478 (13)0.0647 (15)0.0496 (13)0.0051 (11)0.0106 (11)−0.0018 (11)
C170.0384 (11)0.0631 (14)0.0489 (13)−0.0045 (10)0.0108 (10)0.0009 (10)
C180.0499 (13)0.0631 (15)0.0555 (14)0.0051 (11)0.0094 (11)0.0066 (11)
C190.0562 (14)0.0704 (17)0.0622 (15)0.0023 (12)0.0244 (12)0.0011 (12)
C200.0603 (15)0.0692 (16)0.0526 (14)−0.0064 (13)0.0186 (12)0.0107 (12)
C210.0486 (13)0.0677 (16)0.0586 (14)−0.0023 (12)0.0104 (11)0.0153 (12)
C220.0420 (12)0.0654 (15)0.0585 (14)0.0008 (11)0.0114 (11)0.0029 (11)

Geometric parameters (Å, °)

Cl1—C91.744 (2)C8—C91.373 (3)
Cl2—C201.737 (2)C8—H80.9300
N1—C51.372 (3)C9—C101.371 (3)
N1—C61.405 (3)C10—C111.377 (3)
N1—H10.865 (10)C10—H100.9300
N2—C11.338 (3)C11—H110.9300
N2—C51.338 (3)C12—C131.356 (3)
N3—C161.378 (3)C12—H120.9300
N3—C171.393 (3)C13—C141.378 (3)
N3—H30.863 (9)C13—H130.9300
N4—C121.333 (3)C14—C151.359 (3)
N4—C161.333 (3)C14—H140.9300
C1—C21.364 (3)C15—C161.389 (3)
C1—H1A0.9300C15—H150.9300
C2—C31.378 (3)C17—C181.382 (3)
C2—H20.9300C17—C221.396 (3)
C3—C41.362 (3)C18—C191.377 (3)
C3—H3A0.9300C18—H180.9300
C4—C51.400 (3)C19—C201.377 (3)
C4—H40.9300C19—H190.9300
C6—C71.382 (3)C20—C211.373 (3)
C6—C111.383 (3)C21—C221.376 (3)
C7—C81.384 (3)C21—H210.9300
C7—H70.9300C22—H220.9300
C5—N1—C6127.0 (2)C11—C10—H10120.2
C5—N1—H1115.4 (16)C10—C11—C6120.9 (2)
C6—N1—H1116.6 (16)C10—C11—H11119.5
C1—N2—C5116.8 (2)C6—C11—H11119.5
C16—N3—C17127.9 (2)N4—C12—C13124.7 (2)
C16—N3—H3115.4 (15)N4—C12—H12117.6
C17—N3—H3116.0 (15)C13—C12—H12117.6
C12—N4—C16117.2 (2)C12—C13—C14117.4 (2)
N2—C1—C2125.3 (2)C12—C13—H13121.3
N2—C1—H1A117.3C14—C13—H13121.3
C2—C1—H1A117.3C15—C14—C13119.7 (2)
C1—C2—C3116.8 (2)C15—C14—H14120.2
C1—C2—H2121.6C13—C14—H14120.2
C3—C2—H2121.6C14—C15—C16119.0 (2)
C4—C3—C2120.4 (2)C14—C15—H15120.5
C4—C3—H3A119.8C16—C15—H15120.5
C2—C3—H3A119.8N4—C16—N3114.45 (19)
C3—C4—C5118.7 (2)N4—C16—C15121.9 (2)
C3—C4—H4120.7N3—C16—C15123.6 (2)
C5—C4—H4120.7C18—C17—N3124.0 (2)
N2—C5—N1114.34 (19)C18—C17—C22118.3 (2)
N2—C5—C4122.0 (2)N3—C17—C22117.6 (2)
N1—C5—C4123.7 (2)C19—C18—C17120.7 (2)
C7—C6—C11118.9 (2)C19—C18—H18119.6
C7—C6—N1122.6 (2)C17—C18—H18119.6
C11—C6—N1118.5 (2)C18—C19—C20119.9 (2)
C6—C7—C8120.3 (2)C18—C19—H19120.0
C6—C7—H7119.9C20—C19—H19120.0
C8—C7—H7119.9C21—C20—C19120.5 (2)
C9—C8—C7119.8 (2)C21—C20—Cl2120.07 (18)
C9—C8—H8120.1C19—C20—Cl2119.5 (2)
C7—C8—H8120.1C20—C21—C22119.5 (2)
C10—C9—C8120.6 (2)C20—C21—H21120.2
C10—C9—Cl1119.87 (19)C22—C21—H21120.2
C8—C9—Cl1119.55 (19)C21—C22—C17121.0 (2)
C9—C10—C11119.5 (2)C21—C22—H22119.5
C9—C10—H10120.2C17—C22—H22119.5
C5—N2—C1—C2−0.6 (4)C16—N4—C12—C13−0.4 (4)
N2—C1—C2—C30.5 (4)N4—C12—C13—C14−1.9 (5)
C1—C2—C3—C4−0.3 (4)C12—C13—C14—C151.8 (4)
C2—C3—C4—C50.1 (4)C13—C14—C15—C160.5 (4)
C1—N2—C5—N1178.4 (2)C12—N4—C16—N3−179.4 (2)
C1—N2—C5—C40.3 (3)C12—N4—C16—C152.8 (4)
C6—N1—C5—N2−177.0 (2)C17—N3—C16—N4160.2 (2)
C6—N1—C5—C40.9 (4)C17—N3—C16—C15−22.0 (4)
C3—C4—C5—N2−0.1 (4)C14—C15—C16—N4−2.9 (4)
C3—C4—C5—N1−177.9 (2)C14—C15—C16—N3179.5 (2)
C5—N1—C6—C7−51.1 (4)C16—N3—C17—C18−26.8 (4)
C5—N1—C6—C11131.9 (3)C16—N3—C17—C22155.4 (2)
C11—C6—C7—C8−1.9 (3)N3—C17—C18—C19−178.8 (2)
N1—C6—C7—C8−178.9 (2)C22—C17—C18—C19−1.1 (3)
C6—C7—C8—C92.1 (4)C17—C18—C19—C202.0 (4)
C7—C8—C9—C10−0.8 (4)C18—C19—C20—C21−1.5 (4)
C7—C8—C9—Cl1179.35 (19)C18—C19—C20—Cl2178.90 (18)
C8—C9—C10—C11−0.7 (3)C19—C20—C21—C220.1 (3)
Cl1—C9—C10—C11179.13 (17)Cl2—C20—C21—C22179.70 (18)
C9—C10—C11—C60.9 (3)C20—C21—C22—C170.8 (3)
C7—C6—C11—C100.4 (3)C18—C17—C22—C21−0.4 (3)
N1—C6—C11—C10177.5 (2)N3—C17—C22—C21177.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N40.87 (1)2.16 (1)3.018 (3)170 (2)
N3—H3···N20.86 (1)2.22 (1)3.071 (3)171 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2855).

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.
  • Sheldrick, G. M. (1996). SADABS University of Göttigen, Germany.
  • 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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