1-{(1Z)-1-[3-(2,4-Dichloro­phen­oxy)prop­oxy]-1-(2,4-difluoro­phen­yl)prop-1-en-2-yl}-1H-1,2,4-triazole

Yuan-yuan Luan; Yong-hong Hu; Song Guo; Jing Zhu; Wen-ge Yang

doi:10.1107/S1600536812017874

. 2012 May 19;68(Pt 6):o1780. doi: 10.1107/S1600536812017874

1-{(1Z)-1-[3-(2,4-Dichlorophenoxy)propoxy]-1-(2,4-difluorophenyl)prop-1-en-2-yl}-1H-1,2,4-triazole

Yuan-yuan Luan ^a, Yong-hong Hu ^b, Song Guo ^a, Jing Zhu ^a, Wen-ge Yang ^b,^*

PMCID: PMC3379359 PMID: 22719557

Abstract

In the title compound, C₂₀H₁₇Cl₂F₂N₃O₂, the triazole ring makes dihedral angles of 28.0 (3) and 72.5 (2)° with the 2,4-dichloropheny and 2,4-difluorophenyl rings, respectively, and the molecule adopts a Z-conformation about the C=C double bond. In the crystal, C—H⋯O and C—H⋯N hydrogen bonds link the molecules.

Related literature

For a related structure and background to triazoles and further synthetic details, see: Shen et al. (2012 ▶).

Experimental

Crystal data

C₂₀H₁₇Cl₂F₂N₃O₂
M _r = 440.27
Triclinic,
a = 7.4380 (15) Å
b = 8.7600 (18) Å
c = 15.892 (3) Å
α = 89.48 (3)°
β = 84.57 (3)°
γ = 73.74 (3)°
V = 989.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.898, T _max = 0.964
3933 measured reflections
3628 independent reflections
2564 reflections with I > 2σ(I)
R _int = 0.022
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.158
S = 1.01
3628 reflections
262 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.21 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017874/hb6698sup1.cif

e-68-o1780-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017874/hb6698Isup2.hkl

e-68-o1780-Isup2.hkl^{(177.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812017874/hb6698Isup3.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
C4—H4A⋯O1ⁱ	0.93	2.52	3.421 (4)	163
C17—H17A⋯N2ⁱⁱ	0.93	2.56	3.400 (4)	151

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

Acknowledgments

This research work was also supported by the Specialized Research Fund for the Doctoral Program of Higher Education (20113221110005).

supplementary crystallographic information

Comment

As part of our studies on the synthesis of new triazole derivatives (Shen et al. 2012), the crystal structure of the title compound was determined.

In the molecular structure of the title compound the double bond is Z configurated. In the crystal, C-H···O and C-H···N hydrogen bonds link the molecules, in which they seem to be effective in the stabilization of the structure. (Table 1 and Fig. 2).

Experimental

3 g (0.01 mol) 1-(2,4-difluorophenyl)-2-(1,2,4-triazol)-1-y1)propan-1-one, 10 g of a 50% aqueous sodium hydroxide, 15 ml toluene and 1.5 ml of a 40% aqueous solution of tetrabutyl ammonium hydroxide are mixed and heated to 323.15 K under vigorous stirring. 2.8g (0.01 mol) 1-bromo-3-(2.4-dichlorophenoxy)-propane, dissolved in 10 ml toluene, is instilled into the stirred and warmed solution in the course of 10 h. The mixture is subsequently stirred for another 20 h at 323.15 K. The reaction mixture is mixed with as much water and chloroform so that the aqueous phase becomes lighter than the organic phase. Thereafter, the organic and aqueous phases are separated. The organic phase is dried with sodium sulfate. The solvents are distilled under reduced pressure. The impure product herein is subsequently crystallized from a 1:1 mixture of ethyl acetate and ethanol. The purified product may be analytically identified as an approximately pure Z-isomer. Colourless blocks of the title compound were obtained by slow evaporation of an ethanol solution.