1-{(1Z)-1-[6-(4-Chloro­phen­oxy)hex­y­l­oxy]-1-(2,4-difluoro­phen­yl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate

Wen-qian Wan; Kai Wang; Yong-hong Hu; Fei Shen; Wen-ge Yang

doi:10.1107/S1600536811034933

. 2011 Sep 14;67(Pt 10):o2617. doi: 10.1107/S1600536811034933

1-{(1Z)-1-[6-(4-Chlorophenoxy)hexyloxy]-1-(2,4-difluorophenyl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate

Wen-qian Wan ^a, Kai Wang ^a, Yong-hong Hu ^a,^*, Fei Shen ^a, Wen-ge Yang ^a

PMCID: PMC3201488 PMID: 22058762

Abstract

In the title compound, C₂₃H₂₅ClF₂N₃O₂ ⁺·NO₃ ⁻, the triazole ring makes dihedral angles of 60.9 (4) and 25.0 (3)° with the 6-chlorophenyl and 2,4-difluorophenyl rings, respectively. The molecule adopts a Z configuration about the C=C double bond. In the crystal, the cations and anions are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions.

Related literature

For the use of triazole derivatives as antifungal agents, see: Jeu et al. (2003 ▶); Fromtling & Castaner (1996 ▶). For the synthesis, see: Zirngibl & Thiele (1985 ▶).

Experimental

Crystal data

C₂₃H₂₅ClF₂N₃O₂ ⁺·NO₃ ⁻
M _r = 510.92
Monoclinic,
a = 35.538 (7) Å
b = 8.5550 (17) Å
c = 17.072 (3) Å
β = 105.21 (3)°
V = 5008.6 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.21 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 = 0.940, T _max = 0.980
9194 measured reflections
4628 independent reflections
1954 reflections with I > 2σ(I)
R _int = 0.063
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.176
S = 1.00
4628 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 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/S1600536811034933/nc2240sup1.cif

e-67-o2617-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034933/nc2240Isup2.hkl

e-67-o2617-Isup2.hkl^{(226.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034933/nc2240Isup3.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
N3—H3A⋯O4ⁱ	0.86	1.8	2.661 (5)	175
C22—H22A⋯O4ⁱⁱ	0.93	2.38	3.077 (6)	131

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

Acknowledgments

This research work was supported financially by the Program of Six Talent Tops Foundation of Jiangsu Province (2009 No. 2009118) and the Natural Science Basic Research Program of Higher Education in Jiangsu Province (08 K J A530002).

supplementary crystallographic information

Comment

Triazole derivatives such as Voriconazole ((2R,3S)-2-(2,4-difluorophenyl) -3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol) and Posaconazole (4-(4-(4-(4-(((3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4- triazol-1-ylmethyl)oxolan-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)- 2-((2S,3S)-2-hydroxypentan-3-yl)-1,2,4-triazol-3-one) are safe and effective antifungal agents. (Jeu et al., 2003; Fromtling & Castaner, 1996) As part of our studies on the synthesis of new triazole derivatives, 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 structure the anions and cations are connected via N—H···O hydrogen bonding and weak and C—H···O interactions (Table 1 and Fig. 2).

Experimental

Details on the synthesis can be found in the literature reported by Zirngibl & Thiele (1985). 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. 3.0 g (0.01 mol) 1-bromo-6- (4-chlorophenoxy)-hexane, 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 remaining residue is a dark oil that is diluted with 10 ml 2-propanol and then adjusted to a PH-value of 2 by means of 30% aqueous nitric acid. The thus derived nitric acid solution is then cooled in the refrigerator. The impure precipitated 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 of propylene nitrate. Crystals of title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.