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Volume 69 
Part 4 
Page o545  
April 2013  

Received 11 March 2013
Accepted 12 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.009 Å
R = 0.063
wR = 0.147
Data-to-parameter ratio = 15.0
Details
Open access

1-(4-Bromo-3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one: a precursor for phase-I metabolite of AHTN

aBAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany
Correspondence e-mail: franziska.emmerling@bam.de

The title compound, C18H25BrO, crystallized as a racemate with four independent molecules in the asymmetric unit. In the crystal, three of these four molecules are linked via C-Br...Br-C halogen bonds [Br...Br = 3.662 (2) and 3.652 (2) Å], forming dimers.

Related literature

For the crystal structure of the starting material, see: De Ridder et al. (1990[De Ridder, D. J. A., Goubitz, K. & Schenk, H. (1990). Acta Cryst. C46, 2200-2202.]). For the next synthesis step for the title compound (aryl halide to phenol), see: Tlili et al. (2009[Tlili, A., Xia, N., Monnier, F. & Taillefer, M. (2009). Angew. Chem. Int. Ed. 48, 8725-8728.]). For possible abiotic and biotic transformation products of AHTN and HHCB, see: Biselli et al. (2004[Biselli, S., Gatermann, R., Kallenborn, R., Sydnes, L. K. & Hühnerfuss, H. (2004). The Handbook of Environmental Chemistry, Vol. 3, pp. 89-211. Berlin: Springer.]); Martin et al. (2007[Martin, C., Moeder, M., Daniel, X., Krauss, G. & Schlosser, D. (2007). Environ. Sci. Technol. 41, 5395-5402.]); Kuhlich et al. (2010[Kuhlich, P., Göstl, R., Metzinger, R., Piechotta, C. & Nehls, I. (2010). Acta Cryst. E66, o2687.]); Kuhlich, Emmerling et al. (2011[Kuhlich, P., Emmerling, F., Piechotta, C. & Nehls, I. (2011). Acta Cryst. E67, o485.]); Kuhlich, Göstl et al. (2011[Kuhlich, P., Göstl, R., Teichert, P., Piechotta, C. & Nehls, I. (2011). Anal. Bioanal. Chem. 399, 3579-3588.]); Faust et al. (2011[Faust, R., Nauroozi, D., Bruhn, C., Koch, B., Kuhlich, P., Piechotta, C. & Nehls, I. (2011). Acta Cryst. E67, o1462-o1463.]). For model biotic conversion by liver microsomes, see: Esslinger et al. (2011[Esslinger, S., Becker, R., Maul, R. & Nehls, I. (2011). Environ. Sci. Technol. 45, 3938-3944.]). For environmental occurrence of AHTN, see: Heberer (2003[Heberer, T. (2003). Acta Hydroch. Hydrob. 30, 227-243.]). For information on type I and type II halogen interactions, see: Pedireddi et al. (1994[Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju, G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H25BrO

  • Mr = 337.28

  • Monoclinic, C 2/c

  • a = 35.007 (8) Å

  • b = 19.760 (5) Å

  • c = 24.826 (10) Å

  • [beta] = 127.681 (6)°

  • V = 13591 (7) Å3

  • Z = 32

  • Mo K[alpha] radiation

  • [mu] = 2.42 mm-1

  • T = 293 K

  • 0.25 × 0.18 × 0.1 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.85, Tmax = 0.96

  • 35989 measured reflections

  • 11040 independent reflections

  • 5702 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.147

  • S = 1.17

  • 11040 reflections

  • 737 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.59 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6897 ).


Acknowledgements

The authors wish to thank Dr Roland Maul (BAM Federal Institute for Materials Research and Testing, Berlin, Germany) for providing human liver and the protocol for microsomal conversion.

References

Biselli, S., Gatermann, R., Kallenborn, R., Sydnes, L. K. & Hühnerfuss, H. (2004). The Handbook of Environmental Chemistry, Vol. 3, pp. 89-211. Berlin: Springer.
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
De Ridder, D. J. A., Goubitz, K. & Schenk, H. (1990). Acta Cryst. C46, 2200-2202.  [CrossRef] [details]
Esslinger, S., Becker, R., Maul, R. & Nehls, I. (2011). Environ. Sci. Technol. 45, 3938-3944.  [CrossRef] [ChemPort] [PubMed]
Faust, R., Nauroozi, D., Bruhn, C., Koch, B., Kuhlich, P., Piechotta, C. & Nehls, I. (2011). Acta Cryst. E67, o1462-o1463.  [CSD] [CrossRef] [details]
Heberer, T. (2003). Acta Hydroch. Hydrob. 30, 227-243.  [CrossRef] [ChemPort]
Kuhlich, P., Emmerling, F., Piechotta, C. & Nehls, I. (2011). Acta Cryst. E67, o485.  [CSD] [CrossRef] [details]
Kuhlich, P., Göstl, R., Metzinger, R., Piechotta, C. & Nehls, I. (2010). Acta Cryst. E66, o2687.  [CSD] [CrossRef] [details]
Kuhlich, P., Göstl, R., Teichert, P., Piechotta, C. & Nehls, I. (2011). Anal. Bioanal. Chem. 399, 3579-3588.  [ISI] [CrossRef] [ChemPort] [PubMed]
Martin, C., Moeder, M., Daniel, X., Krauss, G. & Schlosser, D. (2007). Environ. Sci. Technol. 41, 5395-5402.  [CrossRef] [PubMed] [ChemPort]
Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju, G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tlili, A., Xia, N., Monnier, F. & Taillefer, M. (2009). Angew. Chem. Int. Ed. 48, 8725-8728.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o545  [ doi:10.1107/S1600536813006934 ]

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