2,2-Bis(4-but­oxy­phen­yl)-1,1,1-trichloro­ethane

Graham Smith

doi:10.1107/S1600536812032680

. 2012 Jul 25;68(Pt 8):o2544. doi: 10.1107/S1600536812032680

2,2-Bis(4-butoxyphenyl)-1,1,1-trichloroethane

Graham Smith ^a,^*

PMCID: PMC3414989 PMID: 22904976

Abstract

In the structure of the title compound, C₂₂H₂₇Cl₃O₂, which is the 4-butoxyphenyl analogue of the insecticidally active 4-methoxyphenyl compound methoxychlor, the dihedral angle between the two benzene rings is 79.61 (11)°. Present also in the structure is an intramolecular aromatic C—H⋯Cl interaction.

Related literature

For background to the mode of action of DDT analogues, see: Läuger et al. (1944 ▶); Kennard & Smith (1980 ▶). For the structures of the insecticides DDT and methoxychlor, see: DeLacy & Kennard (1972 ▶); Smith et al. (1976 ▶).

Experimental

Crystal data

C₂₂H₂₇Cl₃O₂
M _r = 429.79
Monoclinic,
a = 5.7871 (1) Å
b = 18.3112 (5) Å
c = 20.3988 (4) Å
β = 91.160 (2)°
V = 2161.19 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 200 K
0.15 × 0.15 × 0.10 mm

Data collection

Oxford Gemini-S CCD area-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.951, T _max = 0.981
14149 measured reflections
4245 independent reflections
3486 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.110
S = 1.07
4245 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032680/bt5980sup1.cif

e-68-o2544-sup1.cif^{(28.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032680/bt5980Isup2.hkl

e-68-o2544-Isup2.hkl^{(203.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032680/bt5980Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2B—H2B⋯Cl3	0.93	2.69	3.361 (2)	130

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Acknowledgments

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

supplementary crystallographic information

Comment

The title compound, C₂₂H₂₇Cl₃0₂, is the 4-butoxyphenyl analogue of the insecticide DDT [1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane] as well as the 4-methoxyphenyl analogue, also an insecticide (methoxychlor). Criteria for insecticidal activity of the DDT analogues have been described (Läuger et al., 1944; Kennard & Smith, 1980). The crystal structures of both DDT (DeLacy & Kennard, 1972) and methoxychlor (Smith et al., 1976) have been reported but there are no other structures of 4-alkoxyphenyl DDT derivatives in the crystallographic literature.

In the structure of the title compound (Fig. 1), the dihedral angle between the two phenyl planes is 79.61 (11)° which compares with 77.7° in the structure of methoxychlor (Smith et al., 1976) and 64.7° in DDT (DeLacy & Kennard, 1972). The conformations of the two butoxy side chains relative to their phenyl rings (A and B) are essentially identical [comparative torsion angles C3—C4—O4—C11, C4—O4—C11–C21, O4—C11—C21—C31 and C11—C21—C31—C41 are -173.0 (2), 167.44 (19), -62.3 (3), -177.8 (2)° (A) and -170.0 (2), 168.5 (2), -63.9 (3), -171.1 (3)° (B), respectively]. The B ring conformation is stabilized by an intramolecular aromatic C2B—H···Cl3 interaction (Table 1). Present in the crystal packing is a relatively short intermolecular Cl···Cl contact [3.4302 (9) Å] but no other significant interactions are found (Fig. 2).

Experimental

The title compound was obtained as an analytical reference standard from the US Public Health Service. Colourless crystal blocks suitable for X-ray analysis were obtained by room temperature evaporation of a solution in ethanol.