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Volume 69 
Part 4 
Page o620  
April 2013  

Received 23 February 2013
Accepted 22 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.011 Å
R = 0.064
wR = 0.161
Data-to-parameter ratio = 22.0
Details
Open access

3,4',5-Trichlorobiphenyl-4-yl 2,2,2-trichloroethyl sulfate

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

Crystals of the title compound, C14H8Cl6O4S, are twinned by inversion, with unequal components [0.85 (3):0.15 (3)]. The asymmetric unit contains two independent molecules that are related by a pseudo-inversion center. The Car-O [1.393 (9) and 1.397 (9) Å] and ester S-O bond lengths [1.600 (5) and 1.590 (5) Å] of both molecules are comparable to the structurally related 2,3,5,5-trichlorobiphenyl-4-yl 2,2,2-trichloroethyl sulfate. The dihedral angles between the benzene rings in the two molecules are 37.8 (2) and 35.0 (2)°.

Related literature

For related structures of biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters of sulfuric acid, see: Li et al. (2008[Li, X., Parkin, S., Robertson, L. W. & Lehmler, H.-J. (2008). Acta Cryst. E64, o2464.], 2010a[Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010a). Acta Cryst. E66, o1073.],b[Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010b). Environ. Int. 36, 843-848.],c[Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010c). Acta Cryst. E66, o1615-o1616.]). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005[Brandao, T. A. S., Priebe, J. P., Damasceno, A. S., Bortoluzzi, A. J., Kirby, A. J. & Nome, F. (2005). J. Mol. Struct. 734, 205-209.]); Denehy et al. (2006[Denehy, E., White, J. M. & Williams, S. J. (2006). Chem. Commun. pp. 314-316.]). For additional background to sulfate metabolites of polychlorinated biphenyls, see: Liu et al. (2006[Liu, Y., Apak, T. I., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2006). Chem. Res. Toxicol. 19, 1420-1425.], 2009[Liu, Y., Smart, J. T., Song, Y., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2009). Drug Metab. Dispos. 37, 1065-1072.]); Wang et al. (2006[Wang, L.-Q., Lehmler, H.-J., Robertson, L. W. & James, M. O. (2006). Chem. Biol. Interact. 159, 235-246.]); Dhakal et al. (2012[Dhakal, K., He, X., Lehmler, H. J., Teesch, L. M., Duffel, M. W. & Robertson, L. W. (2012). Chem. Res. Toxicol. 25, 2796-2804.]); Zhai et al. (2013[Zhai, G., Lehmler, H. J. & Schnoor, J. L. (2013). Environ. Sci. Technol. 47, 557-562.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8Cl6O4S

  • Mr = 484.96

  • Orthorhombic, P c a 21

  • a = 13.993 (3) Å

  • b = 9.1890 (18) Å

  • c = 28.778 (6) Å

  • V = 3700.3 (13) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 9.71 mm-1

  • T = 90 K

  • 0.17 × 0.09 × 0.02 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.504, Tmax = 0.830

  • 45894 measured reflections

  • 6651 independent reflections

  • 6238 reflections with I > 2[sigma](I)

  • Rint = 0.062

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.161

  • S = 1.15

  • 6651 reflections

  • 302 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.96 e Å-3

  • [Delta][rho]min = -0.85 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3176 Friedel pairs

  • Flack parameter: 0.15 (3)

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). 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: 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: YK2088 ).


Acknowledgements

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

References

Brandao, T. A. S., Priebe, J. P., Damasceno, A. S., Bortoluzzi, A. J., Kirby, A. J. & Nome, F. (2005). J. Mol. Struct. 734, 205-209.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Denehy, E., White, J. M. & Williams, S. J. (2006). Chem. Commun. pp. 314-316.  [CrossRef]
Dhakal, K., He, X., Lehmler, H. J., Teesch, L. M., Duffel, M. W. & Robertson, L. W. (2012). Chem. Res. Toxicol. 25, 2796-2804.  [CrossRef] [ChemPort] [PubMed]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010a). Acta Cryst. E66, o1073.  [CSD] [CrossRef] [details]
Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010b). Environ. Int. 36, 843-848.  [CrossRef] [PubMed] [ChemPort]
Li, X., Parkin, S., Duffel, M. W., Robertson, L. W. & Lehmler, H.-J. (2010c). Acta Cryst. E66, o1615-o1616.  [CrossRef] [details]
Li, X., Parkin, S., Robertson, L. W. & Lehmler, H.-J. (2008). Acta Cryst. E64, o2464.  [CrossRef] [details]
Liu, Y., Apak, T. I., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2006). Chem. Res. Toxicol. 19, 1420-1425.  [CrossRef] [PubMed] [ChemPort]
Liu, Y., Smart, J. T., Song, Y., Lehmler, H.-J., Robertson, L. W. & Duffel, M. W. (2009). Drug Metab. Dispos. 37, 1065-1072.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, L.-Q., Lehmler, H.-J., Robertson, L. W. & James, M. O. (2006). Chem. Biol. Interact. 159, 235-246.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhai, G., Lehmler, H. J. & Schnoor, J. L. (2013). Environ. Sci. Technol. 47, 557-562.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o620  [ doi:10.1107/S1600536813007976 ]

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