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

Smith, G.

doi:10.1107/S1600536812043826

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 (C-C) = 0.004 Å
R = 0.046
wR = 0.092
Data-to-parameter ratio = 14.8
Details

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

Graham Smith ^a ^*

^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-HCl interaction is present.

Related literature

For background to DDT-type insecticides, see: Läuger et al. (1944). For unit-cell data for the title compound, see: Schneider & Fankuchen (1946). For the structures of analogous p-alkoxy-substituted DDT compounds, see: Smith et al. (1976); Smith (2012).

Experimental

Crystal data

C₁₈H₁₉Cl₃O₂
M_r = 373.68
Monoclinic, P 2₁ /c
a = 23.4405 (7) Å
b = 9.8835 (2) Å
c = 7.7924 (2) Å
= 99.536 (3)°
V = 1780.35 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.960, T_max = 0.980
10942 measured reflections
3109 independent reflections
2282 reflections with I > 2(I)
R_int = 0.106

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.092
S = 0.91
3109 reflections
210 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2B-H2BCl2	0.93	2.67	3.321 (3)	128

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); 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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G. (2012). Acta Cryst. E68, o2544.
Smith, G., Kennard, C. H. L. & White, A. H. (1976). Aust. J. Chem. 29, 743-747.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds