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Volume 67 
Part 7 
Page o1577  
July 2011  

Received 26 May 2011
Accepted 30 May 2011
Online 4 June 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.019
wR = 0.051
Data-to-parameter ratio = 20.3
Details
Open access

1,6-Bis(chloromethyl)pyridine

aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C7H7Cl2N, a halogenated derivative of 2,6-lutidine, the C-Cl vectors of the chloromethyl groups point at opposite sides of the aromatic plane to each other. A weak dispersive Cl...Cl contact [3.4342 (3) Å] connects the molecules into a chain along the [101] direction. A [pi]-[pi] interaction with a centroid-centroid distance of 3.7481 (5) Å is also observed.

Related literature

For the crystal structure of the hydrochloride of the title compound, see: Lozano & Jones (2004[Lozano, V. & Jones, P. G. (2004). Acta Cryst. C60, o653-o655.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7Cl2N

  • Mr = 176.04

  • Monoclinic, P 21 /c

  • a = 8.9927 (2) Å

  • b = 12.1581 (3) Å

  • c = 7.4893 (2) Å

  • [beta] = 113.535 (1)°

  • V = 750.72 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.78 mm-1

  • T = 100 K

  • 0.52 × 0.41 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.727, Tmax = 0.872

  • 6994 measured reflections

  • 1845 independent reflections

  • 1768 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.019

  • wR(F2) = 0.051

  • S = 1.09

  • 1845 reflections

  • 91 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2723 ).


Acknowledgements

The authors thank Mr Barry Noble for helpful discussions.

References

Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Lozano, V. & Jones, P. G. (2004). Acta Cryst. C60, o653-o655.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2011). E67, o1577  [ doi:10.1107/S1600536811020678 ]

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