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Volume 69 
Part 7 
Page o1150  
July 2013  

Received 5 March 2013
Accepted 12 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.023
wR = 0.064
Data-to-parameter ratio = 21.4
Details
Open access

1,3-Bis(chloromethyl)benzene

aDepartment of Chemistry, The College of New Jersey, 2000 Pennington Rd, Ewing, NJ 08628, USA
Correspondence e-mail: chan@tcnj.edu

The title compound, C8H8Cl2, used in the synthesis of many pharmaceutical intermediates, forms a three-dimensional network through chlorine-chlorine interactions in the solid-state that measure 3.513 (1) and 3.768 (3) Å.

Related literature

For background information on the applications of halogenated xylenes, see: Ito & Tada (2009[Ito, A. & Tada, N. (2009). Jpn Kokai Tokkyo Koho, JP 2009242338 A 20091022]); Zordan & Brammer (2006[Zordan, F. & Brammer, L. (2006). Cryst. Growth Des. 6, 1374-1379.]). For related structures, see: Castaner et al. (1991[Castaner, J., Riera, J., Carilla, J., Robert, A., Molins, E. & Miravitlles, C. (1991). J. Org. Chem. 56, 103-.]). For halogen-halogen interactions, see: Hathwar et al. (2010[Hathwar, V., Roopan, S., Subashini, R., Khan, F. & Row, T. (2010). J. Chem. Sci. 122, 677-685.]). For additional information on how the space group of the structure was solved, see Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8Cl2

  • Mr = 175.04

  • Orthorhombic, P b c a

  • a = 8.5174 (5) Å

  • b = 12.3094 (7) Å

  • c = 15.2597 (9) Å

  • V = 1599.89 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.73 mm-1

  • T = 100 K

  • 0.51 × 0.50 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.665, Tmax = 0.746

  • 17126 measured reflections

  • 1949 independent reflections

  • 1782 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.064

  • S = 1.04

  • 1949 reflections

  • 91 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. 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: CrystalMaker (CrystalMaker Software, 2009[CrystalMaker Software (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Oxford, England.]); software used to prepare material for publication: enCIFer (Allen et al. 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2106 ).


Acknowledgements

The authors gratefully acknowledge The College of New Jersey's School of Science for research funding and the National Science Foundation for major research instrumentation grant (NSF-0922931) for diffractometer acquisition.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Castaner, J., Riera, J., Carilla, J., Robert, A., Molins, E. & Miravitlles, C. (1991). J. Org. Chem. 56, 103-.  [CrossRef] [ChemPort]
CrystalMaker Software (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Oxford, England.
Hathwar, V., Roopan, S., Subashini, R., Khan, F. & Row, T. (2010). J. Chem. Sci. 122, 677-685.  [CSD] [CrossRef] [ChemPort]
Ito, A. & Tada, N. (2009). Jpn Kokai Tokkyo Koho, JP 2009242338 A 20091022
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zordan, F. & Brammer, L. (2006). Cryst. Growth Des. 6, 1374-1379.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1150  [ doi:10.1107/S1600536813016383 ]

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