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Volume 69 
Part 5 
Page o650  
May 2013  

Received 18 March 2013
Accepted 25 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 17.9
Details
Open access

5,5'-Dichloro-2,2'-dimethoxybiphenyl

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, C14H12Cl2O2, the dihedral angle between the least-square planes of the benzene rings is 62.17 (6)°. Both methoxy groups are slightly out of the plane of the benzene rings to which they are attached, making dihedral angles of 4.22 (18) and 18.82 (16)°.

Related literature

For background to polychlorinated biphenyls, see: Basu et al. (2009[Basu, I., Arnold, K. A., Venier, M. & Hites, R. A. (2009). Environ. Sci. Technol. 43, 6488-6492.]); Hu et al. (2008[Hu, D., Martinez, A. & Hornbuckle, K. C. (2008). Environ. Sci. Technol. 42, 7873-7877.]); Kaminsky et al. (1981[Kaminsky, L. S., Kennedy, M. W., Adams, S. M. & Guengerich, F. P. (1981). Biochemistry, 20, 7379-7384.]); Kennedy et al. (1981[Kennedy, M. W., Carpentier, N. K., Dymerski, P. P. & Kaminsky, L. S. (1981). Biochem. Pharmacol. 30, 577-588.]); McLean et al. (1996[McLean, M. R., Bauer, U., Amaro, A. R. & Robertson, L. W. (1996). Chem. Res. Toxicol. 9, 158-164.]); Rodenburg et al. (2010[Rodenburg, L. A., Guo, J., Du, S. & Cavallo, G. J. (2010). Environ. Sci. Technol. 44, 2816-2821.]). For related structures, see: Chattopadhyay et al. (1987[Chattopadhyay, D., Banerjee, T., Majumdar, S. K., Podder, G., Kashino, S. & Haisa, M. (1987). Acta Cryst. C43, 482-484.]); Nakaema et al. (2008[Nakaema, K., Okamoto, A., Maruyama, S., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o1731.]); Sun et al. (2001[Sun, D. L., Lindeman, S. V., Rathore, R. & Kochi, J. K. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 1585-1594.]). For the synthesis of the title compound, see: Joshi et al. (2011[Joshi, S. N., Vyas, S. M., Duffel, M. W., Parkin, S. & Lehmler, H. J. (2011). Synthesis, pp. 1045-1054.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12Cl2O2

  • Mr = 283.14

  • Monoclinic, P 21 /n

  • a = 10.9629 (2) Å

  • b = 7.2177 (1) Å

  • c = 16.7812 (3) Å

  • [beta] = 104.7108 (7)°

  • V = 1284.32 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 90 K

  • 0.22 × 0.20 × 0.18 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 = 0.899, Tmax = 0.916

  • 21357 measured reflections

  • 2948 independent reflections

  • 2347 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.111

  • S = 1.11

  • 2948 reflections

  • 165 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

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: LH5598 ).


Acknowledgements

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

References

Basu, I., Arnold, K. A., Venier, M. & Hites, R. A. (2009). Environ. Sci. Technol. 43, 6488-6492.  [CrossRef] [PubMed] [ChemPort]
Chattopadhyay, D., Banerjee, T., Majumdar, S. K., Podder, G., Kashino, S. & Haisa, M. (1987). Acta Cryst. C43, 482-484.  [CrossRef] [details]
Hu, D., Martinez, A. & Hornbuckle, K. C. (2008). Environ. Sci. Technol. 42, 7873-7877.  [CrossRef] [PubMed] [ChemPort]
Joshi, S. N., Vyas, S. M., Duffel, M. W., Parkin, S. & Lehmler, H. J. (2011). Synthesis, pp. 1045-1054.
Kaminsky, L. S., Kennedy, M. W., Adams, S. M. & Guengerich, F. P. (1981). Biochemistry, 20, 7379-7384.  [CrossRef] [ChemPort] [PubMed] [ISI]
Kennedy, M. W., Carpentier, N. K., Dymerski, P. P. & Kaminsky, L. S. (1981). Biochem. Pharmacol. 30, 577-588.  [CrossRef] [ChemPort] [PubMed] [ISI]
McLean, M. R., Bauer, U., Amaro, A. R. & Robertson, L. W. (1996). Chem. Res. Toxicol. 9, 158-164.  [CrossRef] [ChemPort] [PubMed]
Nakaema, K., Okamoto, A., Maruyama, S., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o1731.  [CSD] [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.
Rodenburg, L. A., Guo, J., Du, S. & Cavallo, G. J. (2010). Environ. Sci. Technol. 44, 2816-2821.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sun, D. L., Lindeman, S. V., Rathore, R. & Kochi, J. K. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 1585-1594.


Acta Cryst (2013). E69, o650  [ doi:10.1107/S160053681300826X ]

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