[Journal logo]

Volume 68 
Part 11 
Page o3219  
November 2012  

Received 16 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.092
Data-to-parameter ratio = 14.8
Details
Open access

1,1,1-Trichloro-2,2-bis(4-ethoxyphenyl)ethane

aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the title compound, C18H19Cl3O2, which is the 4-ethoxyphenyl analogue of the insecticidally active 4-methoxyphenyl compound methoxychlor, the dihedral angle between the two benzene rings is 60.38 (13)°. An intramolecular aromatic C-H...Cl interaction is present.

Related literature

For background to DDT-type insecticides, see: Läuger et al. (1944[Läuger, P., Martin, H. & Müller, P. H. (1944). Helv. Chim. Acta, 27, 892-928.]). For unit-cell data for the title compound, see: Schneider & Fankuchen (1946[Schneider, M. & Fankuchen, I. (1946). J. Am. Chem. Soc. 68, 2669-2670.]). For the structures of analogous p-alkoxy-substituted DDT compounds, see: Smith et al. (1976[Smith, G., Kennard, C. H. L. & White, A. H. (1976). Aust. J. Chem. 29, 743-747.]); Smith (2012[Smith, G. (2012). Acta Cryst. E68, o2544.]).

[Scheme 1]

Experimental

Crystal data
  • C18H19Cl3O2

  • Mr = 373.68

  • Monoclinic, P 21 /c

  • a = 23.4405 (7) Å

  • b = 9.8835 (2) Å

  • c = 7.7924 (2) Å

  • [beta] = 99.536 (3)°

  • V = 1780.35 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 200 K

  • 0.30 × 0.15 × 0.08 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.960, Tmax = 0.980

  • 10942 measured reflections

  • 3109 independent reflections

  • 2282 reflections with I > 2[sigma](I)

  • Rint = 0.106

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.092

  • S = 0.91

  • 3109 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2B-H2B...Cl2 0.93 2.67 3.321 (3) 128

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5546 ).


Acknowledgements

The author acknowledges financial support from the Australian Research Council and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Läuger, P., Martin, H. & Müller, P. H. (1944). Helv. Chim. Acta, 27, 892-928.
Schneider, M. & Fankuchen, I. (1946). J. Am. Chem. Soc. 68, 2669-2670.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G. (2012). Acta Cryst. E68, o2544.  [CSD] [CrossRef] [details]
Smith, G., Kennard, C. H. L. & White, A. H. (1976). Aust. J. Chem. 29, 743-747.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3219  [ doi:10.1107/S1600536812043826 ]

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.