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

Smith, G.

doi:10.1107/S1600536812032254

Volume 68
Part 8
Page o2504
August 2012

Received 10 July 2012
Accepted 16 July 2012
Online 21 July 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.013 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 16.9
Details

1,1,1-Trichloro-2,2-bis(4-iodophenyl)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 structure of the title compound, C₁₄H₉Cl₃I₂, which is the 4-iodophenyl analogue of the insecticide DDT [1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane], isomorphism between the two compounds has been confirmed. In the molecule, the dihedral angle between the planes of the two benzene rings is 65.8 (4)° which compares with 64.7 (7)° in DDT.

Related literature

For the determination of crystal data for the title compound and the p-bromo substituted DDT analogue, see: Schneider & Fankuchen (1946). For the structures of DDT and related analogues, see: DeLacy & Kennard (1972); Hovmöller et al. (1978).

Experimental

Crystal data

C₁₄H₉Cl₃I₂
M_r = 537.36
Orthorhombic, P c a 2₁
a = 9.8117 (3) Å
b = 20.3445 (4) Å
c = 8.0486 (2) Å
V = 1606.61 (7) Å³
Z = 4
Mo K radiation
= 4.40 mm^-1
T = 200 K
0.25 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.386, T_max = 0.980
5183 measured reflections
2905 independent reflections
2687 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.112
S = 1.08
2905 reflections
172 parameters
1 restraint
H-atom parameters constrained
_max = 0.80 e Å^-3
_min = -0.95 e Å^-3
Absolute structure: Flack (1983), 1203 Friedel pairs
Flack parameter: -0.02 (4)

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: SU2477 ).

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.
DeLacy, T. P. & Kennard, C. H. L. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 2148-2152.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hovmöller, S., Smith, G. & Kennard, C. H. L. (1978). Acta Cryst. B34, 3016-3021.
Schneider, M. & Fankuchen, I. (1946). J. Am. Chem. Soc. 68, 2669-2670.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds