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

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.

In the title compound, C 23 H 25 ClF 2 N 3 O 2 + ÁNO 3 À , the triazole ring makes dihedral angles of 60.9 (4) and 25.0 (3) with the 6chlorophenyl 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-HÁ Á ÁO hydrogen bonds and weak C-HÁ Á ÁO interactions.
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.

Refinement
H atoms were positioned geometrically with C-H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and with N-H = 0.86 Å for triazole H atom, and constrained to ride on their parent atoms, with U iso (H) = 1.2 (or 1.5 for methyl groups) times U eq (C).
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.