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

Luan, Y.; Hu, Y.; Guo, S.; Zhu, J.; Yang, W.

doi:10.1107/S1600536812017874

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1780

doi:10.1107/S1600536812017874

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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 and Wen-ge Yang ^b ^*

^aCollege of Pharmaceutical Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and ^bJiangsu Engineering Technology Research Center of Polypeptide Pharmaceuticals, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: chemywg@126.com

(Received 22 March 2012; accepted 21 April 2012; online 19 May 2012)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.054
wR(F²) = 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

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
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017874/hb6698sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812017874/hb6698Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with displacement ellipsoids drawn at 30% probability levels.
	Fig. 2. The packing diagram of the title compound. Hydron bonds are shown as dashed lines.

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

Crystal data top

C₂₀H₁₇Cl₂F₂N₃O₂	Z = 2
M_r = 440.27	F(000) = 452
Triclinic, P1	D_x = 1.478 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4380 (15) Å	Cell parameters from 25 reflections
b = 8.7600 (18) Å	θ = 9–13°
c = 15.892 (3) Å	µ = 0.37 mm⁻¹
α = 89.48 (3)°	T = 293 K
β = 84.57 (3)°	Block, colorness
γ = 73.74 (3)°	0.30 × 0.20 × 0.10 mm
V = 989.4 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2564 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 25.4°, θ_min = 1.3°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan '(North et al., 1968)	k = −10→10
T_min = 0.898, T_max = 0.964	l = −19→19
3933 measured reflections	3 standard reflections every 200 reflections
3628 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3628 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 1.21 e Å⁻³
2 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₁₇Cl₂F₂N₃O₂	γ = 73.74 (3)°
M_r = 440.27	V = 989.4 (3) Å³
Triclinic, P1	Z = 2
a = 7.4380 (15) Å	Mo Kα radiation
b = 8.7600 (18) Å	µ = 0.37 mm⁻¹
c = 15.892 (3) Å	T = 293 K
α = 89.48 (3)°	0.30 × 0.20 × 0.10 mm
β = 84.57 (3)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.054	2 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.01	Δρ_max = 1.21 e Å⁻³
3628 reflections	Δρ_min = −0.32 e Å⁻³
262 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.48843 (15)	0.85730 (11)	0.59207 (6)	0.0793 (3)
O1	0.0231 (3)	1.0877 (2)	0.22722 (12)	0.0563 (6)
F1	0.0405 (2)	0.8859 (2)	0.07385 (13)	0.0733 (5)
N1	0.0846 (4)	1.4711 (3)	0.11743 (16)	0.0601 (7)
C1	−0.1446 (4)	0.9223 (3)	0.09377 (16)	0.0430 (6)
Cl2	0.39808 (13)	0.30882 (11)	0.71824 (5)	0.0769 (3)
F2	−0.5362 (3)	0.7795 (2)	0.05601 (13)	0.0762 (6)
O2	0.2476 (3)	0.8160 (2)	0.46936 (12)	0.0567 (5)
C2	−0.2436 (4)	0.8278 (3)	0.06304 (18)	0.0494 (7)
H2A	−0.1844	0.7386	0.0291	0.059*
N2	0.1804 (4)	1.4856 (3)	0.24639 (18)	0.0661 (7)
N3	0.0067 (3)	1.3826 (2)	0.17311 (13)	0.0412 (5)
C3	−0.4343 (4)	0.8715 (3)	0.08482 (18)	0.0502 (7)
C4	−0.5252 (4)	1.0021 (4)	0.13428 (18)	0.0536 (7)
H4A	−0.6547	1.0283	0.1479	0.064*
C5	−0.4209 (4)	1.0939 (3)	0.16344 (18)	0.0491 (7)
H5A	−0.4813	1.1835	0.1969	0.059*
C6	−0.2260 (3)	1.0556 (3)	0.14398 (15)	0.0391 (6)
C7	−0.1090 (4)	1.1539 (3)	0.17330 (15)	0.0403 (6)
C8	−0.1167 (3)	1.2983 (3)	0.14444 (15)	0.0388 (6)
C9	−0.2440 (4)	1.3857 (3)	0.08190 (18)	0.0517 (7)
H9A	−0.3213	1.3218	0.0657	0.078*
H9B	−0.1700	1.4075	0.0329	0.078*
H9C	−0.3226	1.4840	0.1069	0.078*
C10	0.1855 (4)	1.5294 (4)	0.1652 (2)	0.0635 (8)
H10A	0.2557	1.5965	0.1441	0.076*
C11	0.0658 (4)	1.3936 (3)	0.24882 (19)	0.0541 (7)
H11A	0.0312	1.3434	0.2970	0.065*
C12	0.0011 (4)	0.9622 (3)	0.28022 (18)	0.0532 (7)
H12A	0.0406	0.8621	0.2488	0.064*
H12B	−0.1297	0.9811	0.3020	0.064*
C13	0.1210 (4)	0.9566 (3)	0.35150 (17)	0.0516 (7)
H13A	0.2475	0.9540	0.3288	0.062*
H13B	0.0706	1.0520	0.3865	0.062*
C14	0.1277 (4)	0.8136 (4)	0.40447 (18)	0.0542 (7)
H14A	0.0024	0.8167	0.4293	0.065*
H14B	0.1770	0.7173	0.3701	0.065*
C15	0.2795 (4)	0.6921 (3)	0.52364 (16)	0.0463 (6)
C16	0.3907 (4)	0.7002 (3)	0.58833 (16)	0.0483 (7)
C17	0.4295 (4)	0.5822 (3)	0.64753 (16)	0.0536 (7)
H17A	0.5028	0.5890	0.6909	0.064*
C18	0.3582 (4)	0.4548 (4)	0.64139 (17)	0.0528 (7)
C19	0.2511 (4)	0.4420 (4)	0.57782 (19)	0.0593 (8)
H19A	0.2043	0.3545	0.5744	0.071*
C20	0.2131 (4)	0.5605 (4)	0.51874 (19)	0.0563 (8)
H20A	0.1418	0.5514	0.4750	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1089 (7)	0.0746 (6)	0.0782 (6)	−0.0529 (5)	−0.0461 (5)	0.0141 (4)
O1	0.0545 (12)	0.0545 (11)	0.0728 (13)	−0.0284 (10)	−0.0339 (10)	0.0327 (10)
F1	0.0522 (10)	0.0749 (12)	0.0908 (13)	−0.0154 (9)	−0.0029 (9)	−0.0087 (10)
N1	0.0683 (17)	0.0634 (16)	0.0633 (16)	−0.0394 (14)	−0.0173 (13)	0.0194 (12)
C1	0.0434 (12)	0.0415 (14)	0.0459 (14)	−0.0140 (11)	−0.0079 (11)	0.0103 (11)
Cl2	0.0869 (6)	0.0753 (6)	0.0652 (5)	−0.0163 (5)	−0.0137 (4)	0.0343 (4)
F2	0.0778 (13)	0.0781 (12)	0.0946 (14)	−0.0494 (11)	−0.0350 (11)	0.0096 (10)
O2	0.0700 (13)	0.0610 (12)	0.0528 (11)	−0.0325 (11)	−0.0326 (10)	0.0198 (9)
C2	0.0566 (18)	0.0445 (15)	0.0531 (16)	−0.0213 (13)	−0.0140 (13)	0.0054 (12)
N2	0.0677 (17)	0.0615 (16)	0.0811 (19)	−0.0301 (14)	−0.0314 (14)	0.0039 (14)
N3	0.0425 (12)	0.0370 (11)	0.0479 (12)	−0.0154 (9)	−0.0102 (10)	0.0041 (9)
C3	0.0591 (18)	0.0484 (15)	0.0554 (16)	−0.0294 (14)	−0.0247 (14)	0.0148 (13)
C4	0.0390 (15)	0.0676 (19)	0.0604 (17)	−0.0222 (14)	−0.0149 (13)	0.0189 (15)
C5	0.0455 (16)	0.0507 (15)	0.0533 (16)	−0.0151 (13)	−0.0114 (12)	0.0080 (13)
C6	0.0379 (14)	0.0400 (14)	0.0435 (13)	−0.0149 (11)	−0.0134 (11)	0.0133 (11)
C7	0.0399 (14)	0.0448 (14)	0.0393 (13)	−0.0144 (11)	−0.0117 (11)	0.0072 (11)
C8	0.0400 (14)	0.0402 (13)	0.0404 (13)	−0.0158 (11)	−0.0115 (11)	0.0051 (11)
C9	0.0614 (18)	0.0445 (15)	0.0576 (16)	−0.0222 (13)	−0.0270 (14)	0.0173 (13)
C10	0.064 (2)	0.0578 (18)	0.081 (2)	−0.0335 (16)	−0.0185 (17)	0.0128 (16)
C11	0.0612 (19)	0.0527 (16)	0.0555 (16)	−0.0227 (14)	−0.0211 (14)	0.0025 (13)
C12	0.0614 (18)	0.0523 (16)	0.0539 (16)	−0.0245 (14)	−0.0218 (14)	0.0183 (13)
C13	0.0611 (18)	0.0471 (15)	0.0523 (16)	−0.0202 (14)	−0.0196 (14)	0.0103 (13)
C14	0.0608 (18)	0.0605 (17)	0.0523 (16)	−0.0283 (15)	−0.0276 (14)	0.0165 (14)
C15	0.0486 (16)	0.0548 (16)	0.0406 (14)	−0.0205 (13)	−0.0126 (12)	0.0134 (12)
C16	0.0521 (17)	0.0511 (16)	0.0442 (15)	−0.0157 (13)	−0.0128 (12)	0.0018 (12)
C17	0.0573 (18)	0.0642 (18)	0.0418 (15)	−0.0174 (15)	−0.0177 (13)	0.0059 (13)
C18	0.0496 (16)	0.0602 (18)	0.0456 (15)	−0.0105 (14)	−0.0060 (13)	0.0161 (13)
C19	0.0620 (19)	0.0601 (18)	0.0656 (19)	−0.0311 (15)	−0.0139 (15)	0.0197 (15)
C20	0.0600 (19)	0.0647 (18)	0.0551 (17)	−0.0302 (15)	−0.0230 (14)	0.0168 (14)

Geometric parameters (Å, º) top

Cl1—C16	1.730 (3)	C7—C8	1.329 (3)
O1—C7	1.367 (3)	C8—C9	1.493 (3)
O1—C12	1.416 (3)	C9—H9A	0.9600
F1—C1	1.331 (3)	C9—H9B	0.9600
N1—C10	1.315 (4)	C9—H9C	0.9600
N1—N3	1.365 (3)	C10—H10A	0.9300
C1—C2	1.372 (4)	C11—H11A	0.9300
C1—C6	1.377 (4)	C12—C13	1.499 (4)
Cl2—C18	1.744 (3)	C12—H12A	0.9700
F2—C3	1.359 (3)	C12—H12B	0.9700
O2—C15	1.362 (3)	C13—C14	1.495 (4)
O2—C14	1.430 (3)	C13—H13A	0.9700
C2—C3	1.372 (4)	C13—H13B	0.9700
C2—H2A	0.9300	C14—H14A	0.9700
N2—C11	1.325 (4)	C14—H14B	0.9700
N2—C10	1.343 (4)	C15—C20	1.381 (4)
N3—C11	1.333 (3)	C15—C16	1.394 (4)
N3—C8	1.435 (3)	C16—C17	1.380 (4)
C3—C4	1.366 (4)	C17—C18	1.371 (4)
C4—C5	1.373 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.368 (4)
C5—C6	1.398 (4)	C19—C20	1.380 (4)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.490 (3)	C20—H20A	0.9300

C7—O1—C12	120.2 (2)	N2—C11—N3	111.0 (3)
C10—N1—N3	102.4 (2)	N2—C11—H11A	124.5
F1—C1—C2	119.0 (3)	N3—C11—H11A	124.5
F1—C1—C6	117.2 (2)	O1—C12—C13	107.3 (2)
C2—C1—C6	123.8 (3)	O1—C12—H12A	110.3
C15—O2—C14	117.3 (2)	C13—C12—H12A	110.3
C1—C2—C3	116.7 (3)	O1—C12—H12B	110.3
C1—C2—H2A	121.7	C13—C12—H12B	110.3
C3—C2—H2A	121.7	H12A—C12—H12B	108.5
C11—N2—C10	102.3 (3)	C14—C13—C12	111.2 (2)
C11—N3—N1	108.8 (2)	C14—C13—H13A	109.4
C11—N3—C8	131.6 (2)	C12—C13—H13A	109.4
N1—N3—C8	119.6 (2)	C14—C13—H13B	109.4
F2—C3—C4	118.9 (3)	C12—C13—H13B	109.4
F2—C3—C2	118.1 (3)	H13A—C13—H13B	108.0
C4—C3—C2	123.0 (3)	O2—C14—C13	107.4 (2)
C3—C4—C5	118.5 (3)	O2—C14—H14A	110.2
C3—C4—H4A	120.8	C13—C14—H14A	110.2
C5—C4—H4A	120.8	O2—C14—H14B	110.2
C4—C5—C6	121.5 (3)	C13—C14—H14B	110.2
C4—C5—H5A	119.3	H14A—C14—H14B	108.5
C6—C5—H5A	119.3	O2—C15—C20	125.4 (2)
C1—C6—C5	116.6 (2)	O2—C15—C16	116.3 (2)
C1—C6—C7	120.4 (2)	C20—C15—C16	118.3 (2)
C5—C6—C7	122.9 (2)	C17—C16—C15	121.0 (3)
C8—C7—O1	118.3 (2)	C17—C16—Cl1	119.6 (2)
C8—C7—C6	123.1 (2)	C15—C16—Cl1	119.3 (2)
O1—C7—C6	118.4 (2)	C18—C17—C16	118.9 (3)
C7—C8—N3	119.7 (2)	C18—C17—H17A	120.5
C7—C8—C9	125.8 (2)	C16—C17—H17A	120.5
N3—C8—C9	114.4 (2)	C19—C18—C17	121.5 (3)
C8—C9—H9A	109.5	C19—C18—Cl2	119.1 (2)
C8—C9—H9B	109.5	C17—C18—Cl2	119.4 (2)
H9A—C9—H9B	109.5	C18—C19—C20	119.3 (3)
C8—C9—H9C	109.5	C18—C19—H19A	120.4
H9A—C9—H9C	109.5	C20—C19—H19A	120.4
H9B—C9—H9C	109.5	C19—C20—C15	121.0 (3)
N1—C10—N2	115.5 (3)	C19—C20—H20A	119.5
N1—C10—H10A	122.2	C15—C20—H20A	119.5
N2—C10—H10A	122.2

F1—C1—C2—C3	−179.4 (2)	C11—N3—C8—C9	141.9 (3)
C6—C1—C2—C3	−0.1 (4)	N1—N3—C8—C9	−38.1 (3)
C10—N1—N3—C11	−0.2 (3)	N3—N1—C10—N2	0.4 (4)
C10—N1—N3—C8	179.8 (2)	C11—N2—C10—N1	−0.4 (4)
C1—C2—C3—F2	−179.4 (2)	C10—N2—C11—N3	0.3 (3)
C1—C2—C3—C4	0.2 (4)	N1—N3—C11—N2	−0.1 (3)
F2—C3—C4—C5	179.7 (2)	C8—N3—C11—N2	179.9 (2)
C2—C3—C4—C5	0.0 (4)	C7—O1—C12—C13	−159.4 (2)
C3—C4—C5—C6	−0.4 (4)	O1—C12—C13—C14	−172.2 (2)
F1—C1—C6—C5	179.1 (2)	C15—O2—C14—C13	−177.7 (2)
C2—C1—C6—C5	−0.2 (4)	C12—C13—C14—O2	178.8 (3)
F1—C1—C6—C7	0.6 (3)	C14—O2—C15—C20	3.4 (4)
C2—C1—C6—C7	−178.7 (2)	C14—O2—C15—C16	−177.6 (3)
C4—C5—C6—C1	0.5 (4)	O2—C15—C16—C17	179.1 (2)
C4—C5—C6—C7	178.9 (2)	C20—C15—C16—C17	−1.8 (4)
C12—O1—C7—C8	159.7 (3)	O2—C15—C16—Cl1	−3.3 (4)
C12—O1—C7—C6	−25.5 (4)	C20—C15—C16—Cl1	175.8 (2)
C1—C6—C7—C8	109.1 (3)	C15—C16—C17—C18	0.7 (4)
C5—C6—C7—C8	−69.4 (4)	Cl1—C16—C17—C18	−177.0 (2)
C1—C6—C7—O1	−65.5 (3)	C16—C17—C18—C19	0.4 (5)
C5—C6—C7—O1	116.1 (3)	C16—C17—C18—Cl2	−177.4 (2)
O1—C7—C8—N3	−2.7 (4)	C17—C18—C19—C20	−0.3 (5)
C6—C7—C8—N3	−177.2 (2)	Cl2—C18—C19—C20	177.5 (2)
O1—C7—C8—C9	176.6 (2)	C18—C19—C20—C15	−0.9 (5)
C6—C7—C8—C9	2.0 (4)	O2—C15—C20—C19	−179.0 (3)
C11—N3—C8—C7	−38.8 (4)	C16—C15—C20—C19	1.9 (5)
N1—N3—C8—C7	141.2 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇Cl₂F₂N₃O₂
M_r	440.27
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4380 (15), 8.7600 (18), 15.892 (3)
α, β, γ (°)	89.48 (3), 84.57 (3), 73.74 (3)
V (Å³)	989.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan '(North et al., 1968)
T_min, T_max	0.898, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	3933, 3628, 2564
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.158, 1.01
No. of reflections	3628
No. of parameters	262
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.21, −0.32

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1.

Acknowledgements

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

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, F., Guo, S., Luan, Y.-Y., Wang, K. & Hu, Y.-H. (2012). Acta Cryst. E68, submited [HB6699]. CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1780

doi:10.1107/S1600536812017874

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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