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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1449.
Published online 2009 May 29. doi:  10.1107/S1600536809019941
PMCID: PMC2969746

2-(3-Chloro­anilino)pyridine

Abstract

In the title compound, C11H9ClN, the dihedral angle between the aromatic ring planes is 44.2 (1)° and the bridging C—N—C bond angle is 127.60 (19)°. The amino N—H grouping makes a hydrogen bond to the pyridyl N atom of an adjacent mol­ecule across a center of inversion, generating a hydrogen-bonded dimer.

Related literature

For the crystal structure of the 4-chloro derivative, see: Fairuz et al. (2008 [triangle]).

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Object name is e-65-o1449-scheme1.jpg

Experimental

Crystal data

  • C11H9ClN2
  • M r = 204.65
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1449-efi1.jpg
  • a = 3.8954 (1) Å
  • b = 10.7804 (4) Å
  • c = 12.4548 (4) Å
  • α = 64.932 (2)°
  • β = 88.004 (2)°
  • γ = 88.240 (2)°
  • V = 473.40 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.36 mm−1
  • T = 119 K
  • 0.40 × 0.05 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.870, T max = 0.993
  • 5923 measured reflections
  • 2064 independent reflections
  • 1807 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.133
  • S = 1.07
  • 2064 reflections
  • 131 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.29 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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019941/tk2464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019941/tk2464Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study (FS314/2008 C, RG027/09AFR).

supplementary crystallographic information

Experimental

2-Chloropyridine (0.5 ml, 5.28 mmol) and 3-chloroaniline (0.67 g, 5.28 mmol) were heated at 423–433 K for 3 h. The solid was dissolved in water and extracted with ether. The ether extract was dried over sodium sulfate. The solvent was evaporated and the product recrystallized from ethanol to yield pale-purple crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation with U(H) fixed at 1.2U(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; the isotropic temperature factor were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the hydrogen-bonded (dashed lines) centrosymmetric dimer {C11H9ClN2}2 with molecules drawn at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H9ClN2Z = 2
Mr = 204.65F(000) = 212
Triclinic, P1Dx = 1.436 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.8954 (1) ÅCell parameters from 1691 reflections
b = 10.7804 (4) Åθ = 3.2–27.7°
c = 12.4548 (4) ŵ = 0.36 mm1
α = 64.932 (2)°T = 119 K
β = 88.004 (2)°Prism, pale purple
γ = 88.240 (2)°0.40 × 0.05 × 0.02 mm
V = 473.40 (3) Å3

Data collection

Bruker SMART APEX diffractometer2064 independent reflections
Radiation source: fine-focus sealed tube1807 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −5→5
Tmin = 0.870, Tmax = 0.993k = −13→14
5923 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0578P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3
2064 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.37 e Å3
1 restraintΔρmin = −0.29 e Å3

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.

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

xyzUiso*/Ueq
Cl10.67761 (16)−0.15289 (6)0.94724 (5)0.0242 (2)
N10.7040 (6)0.3450 (2)0.62528 (17)0.0224 (5)
H10.654 (8)0.390 (3)0.5500 (11)0.024 (7)*
N20.5081 (5)0.5439 (2)0.63195 (17)0.0207 (4)
C10.4688 (6)0.6248 (2)0.6895 (2)0.0215 (5)
H1A0.35970.71180.64920.026*
C20.5768 (7)0.5897 (3)0.8032 (2)0.0237 (5)
H20.54130.65010.84040.028*
C30.7401 (7)0.4624 (2)0.8620 (2)0.0230 (5)
H30.81920.43510.94020.028*
C40.7861 (6)0.3767 (2)0.8060 (2)0.0206 (5)
H40.89820.29010.84430.025*
C50.6623 (6)0.4211 (2)0.69013 (19)0.0186 (5)
C60.8088 (6)0.2076 (2)0.6660 (2)0.0185 (5)
C70.7102 (6)0.1066 (2)0.77788 (19)0.0179 (5)
H70.57470.13060.83140.022*
C80.8122 (6)−0.0275 (2)0.80912 (19)0.0179 (5)
C91.0038 (6)−0.0685 (2)0.7336 (2)0.0209 (5)
H91.0677−0.16190.75650.025*
C101.0995 (6)0.0324 (3)0.6223 (2)0.0225 (5)
H101.23160.00750.56870.027*
C111.0045 (6)0.1685 (2)0.5891 (2)0.0201 (5)
H111.07310.23570.51320.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0325 (4)0.0186 (3)0.0169 (3)−0.0002 (2)−0.0003 (2)−0.0032 (2)
N10.0351 (12)0.0172 (10)0.0128 (9)0.0037 (8)−0.0029 (8)−0.0044 (8)
N20.0263 (11)0.0173 (9)0.0156 (9)0.0010 (8)0.0006 (8)−0.0043 (7)
C10.0234 (12)0.0194 (11)0.0205 (11)0.0009 (9)0.0027 (9)−0.0076 (9)
C20.0287 (13)0.0228 (12)0.0222 (12)−0.0034 (10)0.0036 (10)−0.0119 (10)
C30.0297 (13)0.0224 (12)0.0158 (11)−0.0051 (10)−0.0008 (9)−0.0069 (9)
C40.0225 (12)0.0183 (11)0.0194 (11)−0.0007 (9)−0.0038 (9)−0.0061 (9)
C50.0227 (12)0.0169 (11)0.0135 (10)−0.0034 (9)0.0011 (8)−0.0038 (8)
C60.0192 (11)0.0185 (11)0.0173 (11)0.0007 (9)−0.0028 (8)−0.0071 (9)
C70.0191 (11)0.0204 (11)0.0139 (10)0.0021 (9)−0.0005 (8)−0.0070 (9)
C80.0198 (11)0.0166 (10)0.0139 (10)−0.0013 (8)−0.0022 (8)−0.0029 (8)
C90.0227 (12)0.0180 (11)0.0224 (11)0.0032 (9)−0.0038 (9)−0.0091 (9)
C100.0209 (12)0.0286 (13)0.0201 (11)0.0026 (9)−0.0002 (9)−0.0126 (10)
C110.0202 (12)0.0244 (12)0.0145 (10)−0.0011 (9)−0.0004 (8)−0.0071 (9)

Geometric parameters (Å, °)

Cl1—C81.752 (2)C4—C51.411 (3)
N1—C51.376 (3)C4—H40.9500
N1—C61.400 (3)C6—C111.396 (3)
N1—H10.880 (10)C6—C71.406 (3)
N2—C51.345 (3)C7—C81.378 (3)
N2—C11.346 (3)C7—H70.9500
C1—C21.380 (3)C8—C91.386 (3)
C1—H1A0.9500C9—C101.398 (3)
C2—C31.397 (3)C9—H90.9500
C2—H20.9500C10—C111.386 (3)
C3—C41.378 (3)C10—H100.9500
C3—H30.9500C11—H110.9500
C5—N1—C6127.60 (19)N1—C6—C11118.1 (2)
C5—N1—H1114.3 (19)N1—C6—C7123.0 (2)
C6—N1—H1118.1 (19)C11—C6—C7118.8 (2)
C5—N2—C1117.3 (2)C8—C7—C6119.3 (2)
N2—C1—C2124.2 (2)C8—C7—H7120.4
N2—C1—H1A117.9C6—C7—H7120.4
C2—C1—H1A117.9C7—C8—C9122.7 (2)
C1—C2—C3117.8 (2)C7—C8—Cl1118.76 (18)
C1—C2—H2121.1C9—C8—Cl1118.48 (17)
C3—C2—H2121.1C8—C9—C10117.6 (2)
C4—C3—C2119.7 (2)C8—C9—H9121.2
C4—C3—H3120.1C10—C9—H9121.2
C2—C3—H3120.1C11—C10—C9121.0 (2)
C3—C4—C5118.2 (2)C11—C10—H10119.5
C3—C4—H4120.9C9—C10—H10119.5
C5—C4—H4120.9C10—C11—C6120.6 (2)
N2—C5—N1114.4 (2)C10—C11—H11119.7
N2—C5—C4122.7 (2)C6—C11—H11119.7
N1—C5—C4122.8 (2)
C5—N2—C1—C20.2 (4)C5—N1—C6—C737.1 (4)
N2—C1—C2—C30.6 (4)N1—C6—C7—C8177.1 (2)
C1—C2—C3—C4−0.4 (4)C11—C6—C7—C80.8 (3)
C2—C3—C4—C5−0.5 (4)C6—C7—C8—C9−1.4 (4)
C1—N2—C5—N1−178.1 (2)C6—C7—C8—Cl1−178.31 (17)
C1—N2—C5—C4−1.1 (4)C7—C8—C9—C101.1 (4)
C6—N1—C5—N2−170.1 (2)Cl1—C8—C9—C10178.04 (18)
C6—N1—C5—C412.9 (4)C8—C9—C10—C11−0.2 (4)
C3—C4—C5—N21.3 (4)C9—C10—C11—C6−0.3 (4)
C3—C4—C5—N1178.1 (2)N1—C6—C11—C10−176.5 (2)
C5—N1—C6—C11−146.5 (2)C7—C6—C11—C100.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.88 (1)2.18 (1)3.042 (3)167 (3)

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: TK2464).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fairuz, M. Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1800. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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