1,3-Phenyl­ene bis­{3-[2-chloro-4-(tri­fluoro­meth­yl)phen­oxy]benzoate}

Hao Peng; Hongwu He

doi:10.1107/S1600536812030826

. 2012 Jul 14;68(Pt 8):o2437. doi: 10.1107/S1600536812030826

1,3-Phenylene bis{3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoate}

Hao Peng ^a, Hongwu He ^a,^*

PMCID: PMC3414352 PMID: 22904885

Abstract

In the title compound, C₃₄H₁₈Cl₂F₆O₆, one terminal trifluoromethyl and one entire 2-chloro-4-(trifluoromethyl)phenyl group are disordered with refined occupancy ratios of 0.715 (11):0.285 (11) and 0.517 (5):0.429 (5), respectively. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into ribbons propagating along the a-axis direction.

Related literature

For the herbicidal activity of phenoxyphenyl derivatives, see: Dayan & Allen (2000 ▶). For the structures of related compounds, see: Peng & He (2006 ▶, 2007 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₃₄H₁₈Cl₂F₆O₆
M _r = 707.38
Triclinic,
a = 7.7175 (11) Å
b = 8.7399 (12) Å
c = 23.973 (3) Å
α = 92.986 (2)°
β = 98.485 (3)°
γ = 92.611 (3)°
V = 1594.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
13550 measured reflections
5564 independent reflections
3199 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.257
S = 1.00
5564 reflections
528 parameters
215 restraints
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); 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/S1600536812030826/bg2468sup1.cif

e-68-o2437-sup1.cif^{(31.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030826/bg2468Isup2.hkl

e-68-o2437-Isup2.hkl^{(272.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030826/bg2468Isup3.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
C20—H20⋯O1ⁱ	0.93	2.50	3.412 (5)	166
C10—H10⋯O2ⁱⁱ	0.93	2.59	3.152 (5)	120

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors gratefully acknowledge financial support of this work by the National Basic Research Program of China (grant No. 2010CB126100), the National Natural Science Foundation of China (grant Nos. 21172090 and 21002037). The research was supported in part by the PCSIRT (grant No. IRT0953).

supplementary crystallographic information

Comment

Phenoxyphenyl derivatives exhibit herbicidal activity by interacting with plant metabolism in multiple ways. Many diphenyl ether inhibitors of protoporphyrinogen oxidase contains 2-chloro-4-(trifluoromethyl)phenoxy benzoate moiety, which have been a successful class of herbicides (Dayan & Allen, 2000). The title compound has been prepared as a part our work on the design and synthesis of novel herbicidal compounds.

Fig. 1 shows the crystal structure of the title compound. Bond lengths and angles show normal values (Allen et al., 1987). The terminal trifluoromethyl and one of 2-chloro-4-(trifluoromethyl)phenoxy groups are disordered and required a strongly restrained refinement. The C28···C33 ring, Cg5, is rotated almost 180° to the C28'···C33' ring, Cg6, by dihedral angle 2.79°. In the crystal, molecules are linked via weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

3-(2-Chloro-4-(trifluoromethyl)phenoxy)benzoyl chloride (0.005 mol) in chloroform was added dropwise at 275–278 K to a stirred solution of phen-1,3-diol (0.0025 mol) and triethylamine (0.005 mol) in chloroform (25 mL). The mixture was stirred at 275–278 K for 1 h, washed with 1% hydrochloric acid solution, followed by sodium hydrogen carbonate and ice water, dried and evaporated. The residue was purified by chromatography (silica gel with 15% acetone in petroleum ether). Recrystallization from ethyl acetate and petroleum ether over 1 week gave colorless blocks of the title compound.