[Journal logo]

Volume 69 
Part 6 
Page o983  
June 2013  

Received 8 May 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.081
Data-to-parameter ratio = 19.8
Details
Open access

2,2',5',6-Tetrachloro-4-[(1S)-1-methylpropoxy]biphenyl

aThe University of Iowa, Department of Occupational and Environmental Health, Iowa City, IA 52242-5000, USA, and bUniversity of Kentucky, Department of Chemistry, Lexington, KY 40506-0055, USA
Correspondence e-mail: hans-joachim-lehmler@uiowa.edu

In the title molecule, C16H14Cl4O, the dihedral angle between the least-square planes of the benzene rings is 84.40 (7)°. No unusual intermolecular interactions are present.

Related literature

For related literature about polychlorinated biphenyls, see: Lehmler et al. (2010[Lehmler, H.-J., Harrad, S. J., Huhnerfuss, H., Kania-Korwel, I., Lee, C. M., Lu, Z. & Wong, C. S. (2010). Environ. Sci. Technol. 44, 2757-2766.]); Warner et al. (2009[Warner, N. A., Martin, J. W. & Wong, C. S. (2009). Environ. Sci. Technol. 43, 114-121.]). For crystal structures of PCB derivatives with two or less ortho chlorine substituents, see: Mannila & Rissanen (1994[Mannila, E. & Rissanen, K. (1994). Acta Chem. Scand. 48, 600-602.]); Miao et al. (1996[Miao, X.-S., Chu, S.-G., Xu, X.-B. & Jin, X.-L. (1996). Acta Cryst. C52, 2582-2583.]); Rissanen et al. (1988a[Rissanen, K., Valkonen, J. & Mannila, B. (1988a). Acta Cryst. C44, 682-684.]); Shaikh et al. (2008[Shaikh, N. S., Parkin, S., Luthe, G. & Lehmler, H.-J. (2008). Chemosphere, 70, 1694-1698.]); Singh et al. (1986[Singh, P., Pedersen, L. G. & McKinney, J. D. (1986). Acta Cryst. C42, 1172-1175.]); van der Sluis et al. (1990[Sluis, P. van der, Moes, G. W. H., Behm, H., Smykalla, C., Beurskens, P. T. & Lenstra, A. T. H. (1990). Acta Cryst. C46, 2169-2171.]); Vyas et al. (2006[Vyas, S. M., Parkin, S. & Lehmler, H.-J. (2006). Acta Cryst. E62, o2905-o2906.]). For crystal structures of PCB derivatives with three ortho chlorine substituents, see: Lehmler et al. (2005[Lehmler, H.-J., Robertson, L. W. & Parkin, S. (2005). Acta Cryst. E61, o3025-o3026.]); Rissanen et al. (1988b[Rissanen, K., Valkonen, J. & Mannila, B. (1988b). Acta Cryst. C44, 684-686.]). For crystal structures of PCB derivatives with four ortho chlorine substituents, see: Pedersen (1975[Pedersen, B. F. (1975). Acta Cryst. B31, 2931-2933.]); Singh & McKinney (1979[Singh, P. & McKinney, J. D. (1979). Acta Cryst. B35, 259-262.]). For literature about the Mitsunobu reaction, see: Fujita et al. (2001[Fujita, M., Matsushima, H., Sugimura, T., Tai, A. & Okuyama, T. (2001). J. Am. Chem. Soc. 123, 2946-2957.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14Cl4O

  • Mr = 364.07

  • Orthorhombic, P 21 21 21

  • a = 10.3301 (2) Å

  • b = 10.5415 (2) Å

  • c = 15.2160 (3) Å

  • V = 1656.94 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.71 mm-1

  • T = 90 K

  • 0.25 × 0.25 × 0.08 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.843, Tmax = 0.946

  • 22321 measured reflections

  • 3797 independent reflections

  • 3351 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.081

  • S = 1.09

  • 3797 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1625 Friedel pairs

  • Flack parameter: 0.00 (6)

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and local procedures.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5329 ).


Acknowledgements

This research was supported by grants ES05605, ES013661 and ES017425 from the National Institute of Environmental Health Sciences, National Institutes of Health.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Fujita, M., Matsushima, H., Sugimura, T., Tai, A. & Okuyama, T. (2001). J. Am. Chem. Soc. 123, 2946-2957.  [CrossRef] [ChemPort]
Lehmler, H.-J., Harrad, S. J., Huhnerfuss, H., Kania-Korwel, I., Lee, C. M., Lu, Z. & Wong, C. S. (2010). Environ. Sci. Technol. 44, 2757-2766.  [CrossRef] [ChemPort] [PubMed]
Lehmler, H.-J., Robertson, L. W. & Parkin, S. (2005). Acta Cryst. E61, o3025-o3026.  [CSD] [CrossRef] [ChemPort] [details]
Mannila, E. & Rissanen, K. (1994). Acta Chem. Scand. 48, 600-602.  [CrossRef] [ChemPort]
Miao, X.-S., Chu, S.-G., Xu, X.-B. & Jin, X.-L. (1996). Acta Cryst. C52, 2582-2583.  [CrossRef] [details]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pedersen, B. F. (1975). Acta Cryst. B31, 2931-2933.  [CrossRef] [details]
Rissanen, K., Valkonen, J. & Mannila, B. (1988a). Acta Cryst. C44, 682-684.  [CrossRef] [details]
Rissanen, K., Valkonen, J. & Mannila, B. (1988b). Acta Cryst. C44, 684-686.  [CrossRef] [details]
Shaikh, N. S., Parkin, S., Luthe, G. & Lehmler, H.-J. (2008). Chemosphere, 70, 1694-1698.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, P. & McKinney, J. D. (1979). Acta Cryst. B35, 259-262.  [CrossRef] [details]
Singh, P., Pedersen, L. G. & McKinney, J. D. (1986). Acta Cryst. C42, 1172-1175.  [CrossRef] [details]
Sluis, P. van der, Moes, G. W. H., Behm, H., Smykalla, C., Beurskens, P. T. & Lenstra, A. T. H. (1990). Acta Cryst. C46, 2169-2171.  [CrossRef] [details]
Vyas, S. M., Parkin, S. & Lehmler, H.-J. (2006). Acta Cryst. E62, o2905-o2906.  [CSD] [CrossRef] [ChemPort] [details]
Warner, N. A., Martin, J. W. & Wong, C. S. (2009). Environ. Sci. Technol. 43, 114-121.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o983  [ doi:10.1107/S1600536813014098 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.