1-{(Z)-1-[3-(4-Bromo­phen­oxy)prop­oxy]-1-(2,4-difluoro­phen­yl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate

Shen, F.; Guo, S.; Luan, Y.; Wang, K.; Hu, Y.

doi:10.1107/S1600536812024154

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2010

https://doi.org/10.1107/S1600536812024154

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1-{(Z)-1-[3-(4-Bromophenoxy)propoxy]-1-(2,4-difluorophenyl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate

Fei Shen,^a Song Guo,^a Yuan-yuan Luan,^b Kai Wang ^a and Yong-hong Hu ^a ^*

^aJiangsu Engineering Technology Research Center of Polypeptide Pharmaceutical, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Pharmaceutical Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: yonghonghu09@gmail.com

(Received 22 March 2012; accepted 27 May 2012; online 13 June 2012)

In the title molecular salt, C₂₀H₁₉BrF₂N₃O₂⁺·NO₃⁻, the N atom at position 4 of the heterocyclic ring is protonated. The triazole ring makes dihedral angles of 96.6 (4) and 54.4 (3)° with the 4-bromophenyl and 2,4-difluorophenyl rings, respectively, and the molecule adopts a Z conformation about the C=C double bond. In the crystal, cations and anions are linked by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background to the uses of triazole derivatives, see: Jeu et al. (2003 ); Fromtling & Castaner (1996 ). For further synthetic details, see: Ludwig & Kurt (1985 ).

Experimental

Crystal data

C₂₀H₁₉BrF₂N₃O₂⁺·NO₃⁻
M_r = 513.30
Triclinic, $[P \overline 1]$
a = 8.3030 (17) Å
b = 8.4260 (17) Å
c = 16.170 (3) Å
α = 91.10 (3)°
β = 95.80 (3)°
γ = 102.30 (3)°
V = 1098.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.699, T_max = 0.831
4329 measured reflections
4029 independent reflections
2250 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.152
S = 1.01
4029 reflections
289 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4	0.86	1.95	2.790 (6)	167
C9—H9A⋯O3ⁱ	0.93	2.55	3.271 (7)	135
C10—H10A⋯O3ⁱⁱ	0.93	2.49	3.263 (7)	140
C10—H10A⋯O5ⁱⁱ	0.93	2.42	3.340 (7)	168
C19—H19A⋯O3	0.93	2.54	3.276 (7)	137
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -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: https://doi.org/10.1107/S1600536812024154/hb6699sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024154/hb6699Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024154/hb6699Isup3.cml

checkCIF report

Comment top

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 has a Z conformation. In the crystal structure the anions and cations are connected via N—H···O and C—H···O hydrogen bonding (Table 1 and Fig. 2).

Related literature top

For background to the uses of triazole derivatives, see: Jeu et al. (2003); Fromtling & Castaner (1996). For further synthetic details, see: Ludwig & Kurt (1985).

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. 2.93 g (0.01 mol) 1-bromo-3-(4-bromophenoxy)-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 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. Colourless plates of the title compound were obtained by slow evaporation of an ethanol solution. Details on the synthesis can be found in the literature reported by Ludwig & Kurt (1985).

Structure description top

For background to the uses of triazole derivatives, see: Jeu et al. (2003); Fromtling & Castaner (1996). For further synthetic details, see: Ludwig & Kurt (1985).

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-{(Z)-1-[3-(4-Bromophenoxy)propoxy]-1-(2,4-difluorophenyl)prop-1-en- 2-yl}-1H-1,2,4-triazol-4-ium nitrate top

Crystal data top

C₂₀H₁₉BrF₂N₃O₂⁺·NO₃⁻	Z = 2
M_r = 513.30	F(000) = 520
Triclinic, P1	D_x = 1.552 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3030 (17) Å	Cell parameters from 25 reflections
b = 8.4260 (17) Å	θ = 9–13°
c = 16.170 (3) Å	µ = 1.93 mm⁻¹
α = 91.10 (3)°	T = 293 K
β = 95.80 (3)°	Plate, colorless
γ = 102.30 (3)°	0.20 × 0.10 × 0.10 mm
V = 1098.7 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2250 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.4°, θ_min = 1.3°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −10→9
T_min = 0.699, T_max = 0.831	l = −19→19
4329 measured reflections	3 standard reflections every 200 reflections
4029 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.075P)²] where P = (F_o² + 2F_c²)/3
4029 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.49 e Å⁻³
1 restraint	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₀H₁₉BrF₂N₃O₂⁺·NO₃⁻	γ = 102.30 (3)°
M_r = 513.30	V = 1098.7 (4) Å³
Triclinic, P1	Z = 2
a = 8.3030 (17) Å	Mo Kα radiation
b = 8.4260 (17) Å	µ = 1.93 mm⁻¹
c = 16.170 (3) Å	T = 293 K
α = 91.10 (3)°	0.20 × 0.10 × 0.10 mm
β = 95.80 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2250 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.699, T_max = 0.831	3 standard reflections every 200 reflections
4329 measured reflections	intensity decay: 1%
4029 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	1 restraint
wR(F²) = 0.152	H-atom parameters constrained
S = 1.01	Δρ_max = 0.49 e Å⁻³
4029 reflections	Δρ_min = −0.47 e Å⁻³
289 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
Br	0.98343 (10)	0.93868 (9)	0.81164 (4)	0.0842 (3)
O1	0.5622 (4)	0.7633 (4)	0.2460 (2)	0.0504 (9)
N1	0.6426 (5)	0.4746 (5)	0.2587 (2)	0.0415 (10)
F1	−0.0592 (5)	0.7759 (6)	−0.0124 (3)	0.1075 (14)
C1	0.1701 (7)	0.5970 (7)	0.1459 (3)	0.0567 (15)
H1A	0.1495	0.5219	0.1871	0.068*
O2	0.7624 (4)	1.0648 (4)	0.4584 (2)	0.0546 (10)
F2	0.5119 (5)	0.8501 (5)	0.0607 (2)	0.0953 (13)
N2	0.7812 (5)	0.4226 (5)	0.2392 (3)	0.0516 (11)
C2	0.0372 (7)	0.6312 (8)	0.0959 (4)	0.0686 (17)
H2B	−0.0714	0.5805	0.1027	0.082*
N3	0.7821 (5)	0.4579 (5)	0.3707 (3)	0.0445 (10)
H3A	0.8152	0.4614	0.4230	0.053*
C3	0.0711 (8)	0.7408 (8)	0.0371 (4)	0.0676 (17)
C4	0.2289 (8)	0.8143 (8)	0.0214 (4)	0.0734 (18)
H4A	0.2481	0.8853	−0.0216	0.088*
C5	0.3555 (7)	0.7772 (7)	0.0724 (3)	0.0605 (15)
C6	0.3333 (6)	0.6713 (6)	0.1366 (3)	0.0456 (12)
C7	0.4737 (6)	0.6405 (6)	0.1930 (3)	0.0425 (12)
C8	0.5168 (6)	0.4976 (6)	0.1943 (3)	0.0449 (12)
C9	0.8628 (7)	0.4159 (6)	0.3118 (4)	0.0504 (14)
H9A	0.9642	0.3854	0.3204	0.060*
C10	0.6445 (6)	0.4938 (6)	0.3394 (3)	0.0402 (12)
H10A	0.5645	0.5261	0.3681	0.048*
C11	0.4530 (8)	0.3536 (7)	0.1346 (4)	0.0704 (18)
H11A	0.3712	0.3784	0.0935	0.106*
H11B	0.4040	0.2615	0.1645	0.106*
H11C	0.5432	0.3289	0.1077	0.106*
C12	0.4855 (7)	0.8956 (6)	0.2671 (3)	0.0530 (14)
H12A	0.3866	0.8547	0.2941	0.064*
H12B	0.4542	0.9490	0.2172	0.064*
C13	0.6100 (7)	1.0130 (6)	0.3248 (3)	0.0530 (14)
H13A	0.5696	1.1117	0.3321	0.064*
H13B	0.7131	1.0415	0.2997	0.064*
C14	0.6429 (7)	0.9442 (6)	0.4086 (3)	0.0528 (14)
H14A	0.5411	0.9168	0.4348	0.063*
H14B	0.6851	0.8463	0.4023	0.063*
C15	0.8075 (6)	1.0270 (6)	0.5371 (3)	0.0446 (12)
C16	0.9266 (7)	1.1447 (6)	0.5838 (4)	0.0536 (14)
H16A	0.9712	1.2414	0.5598	0.064*
C17	0.9793 (7)	1.1207 (7)	0.6646 (4)	0.0565 (15)
H17A	1.0592	1.2002	0.6952	0.068*
C18	0.9121 (7)	0.9758 (7)	0.7007 (3)	0.0545 (14)
C19	0.7945 (7)	0.8595 (7)	0.6547 (4)	0.0562 (15)
H19A	0.7494	0.7628	0.6786	0.067*
C20	0.7436 (7)	0.8845 (6)	0.5745 (4)	0.0568 (15)
H20A	0.6643	0.8041	0.5441	0.068*
O4	0.8591 (4)	0.5077 (4)	0.5425 (2)	0.0537 (9)
N4	0.7288 (6)	0.4501 (5)	0.5751 (3)	0.0502 (11)
O3	0.7345 (5)	0.4623 (5)	0.6516 (3)	0.0658 (11)
O5	0.6014 (5)	0.3882 (5)	0.5316 (3)	0.0775 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0977 (6)	0.0922 (6)	0.0618 (4)	0.0230 (4)	−0.0016 (4)	0.0056 (4)
O1	0.048 (2)	0.042 (2)	0.061 (2)	0.0136 (17)	−0.0076 (18)	−0.0066 (17)
N1	0.039 (2)	0.039 (2)	0.048 (3)	0.0110 (19)	0.005 (2)	−0.0007 (19)
F1	0.083 (3)	0.147 (4)	0.093 (3)	0.038 (3)	−0.022 (2)	0.035 (3)
C1	0.055 (4)	0.059 (4)	0.051 (3)	0.004 (3)	−0.001 (3)	0.010 (3)
O2	0.057 (2)	0.034 (2)	0.065 (2)	0.0005 (17)	−0.0107 (19)	−0.0009 (18)
F2	0.066 (2)	0.120 (3)	0.091 (3)	−0.004 (2)	0.007 (2)	0.046 (2)
N2	0.045 (3)	0.059 (3)	0.054 (3)	0.017 (2)	0.010 (2)	−0.003 (2)
C2	0.046 (4)	0.089 (5)	0.065 (4)	0.012 (3)	−0.013 (3)	0.003 (4)
N3	0.036 (2)	0.041 (2)	0.054 (3)	0.006 (2)	−0.003 (2)	0.004 (2)
C3	0.065 (4)	0.091 (5)	0.049 (3)	0.032 (4)	−0.016 (3)	0.010 (3)
C4	0.077 (5)	0.080 (5)	0.061 (4)	0.014 (4)	−0.004 (4)	0.024 (3)
C5	0.055 (4)	0.070 (4)	0.050 (3)	0.002 (3)	−0.002 (3)	0.014 (3)
C6	0.046 (3)	0.048 (3)	0.040 (3)	0.008 (3)	−0.003 (2)	−0.003 (2)
C7	0.041 (3)	0.046 (3)	0.038 (3)	0.007 (3)	−0.002 (2)	0.002 (2)
C8	0.042 (3)	0.045 (3)	0.045 (3)	0.008 (2)	−0.003 (2)	−0.003 (2)
C9	0.038 (3)	0.052 (3)	0.066 (4)	0.018 (3)	0.013 (3)	−0.003 (3)
C10	0.031 (3)	0.040 (3)	0.051 (3)	0.010 (2)	0.009 (2)	0.003 (2)
C11	0.070 (4)	0.062 (4)	0.075 (4)	0.016 (3)	−0.009 (3)	−0.020 (3)
C12	0.051 (3)	0.044 (3)	0.063 (3)	0.015 (3)	−0.009 (3)	0.002 (3)
C13	0.058 (4)	0.032 (3)	0.065 (4)	0.006 (3)	−0.005 (3)	−0.004 (3)
C14	0.047 (3)	0.036 (3)	0.070 (4)	0.001 (3)	0.002 (3)	−0.005 (3)
C15	0.043 (3)	0.029 (3)	0.062 (3)	0.010 (2)	0.004 (3)	−0.005 (2)
C16	0.050 (3)	0.033 (3)	0.074 (4)	0.006 (3)	0.000 (3)	0.002 (3)
C17	0.051 (3)	0.050 (4)	0.067 (4)	0.014 (3)	−0.006 (3)	−0.004 (3)
C18	0.051 (3)	0.057 (4)	0.058 (3)	0.019 (3)	0.006 (3)	−0.005 (3)
C19	0.063 (4)	0.044 (3)	0.061 (4)	0.009 (3)	0.011 (3)	0.003 (3)
C20	0.054 (4)	0.034 (3)	0.077 (4)	0.000 (3)	0.002 (3)	−0.007 (3)
O4	0.035 (2)	0.057 (2)	0.067 (2)	0.0034 (17)	0.0080 (18)	0.0052 (19)
N4	0.042 (3)	0.038 (3)	0.074 (3)	0.012 (2)	0.012 (3)	0.007 (2)
O3	0.074 (3)	0.071 (3)	0.056 (3)	0.016 (2)	0.020 (2)	0.011 (2)
O5	0.038 (2)	0.091 (3)	0.091 (3)	−0.010 (2)	0.003 (2)	0.000 (3)

Geometric parameters (Å, º) top

Br—C18	1.884 (6)	C9—H9A	0.9300
O1—C7	1.364 (6)	C10—H10A	0.9300
O1—C12	1.448 (6)	C11—H11A	0.9600
N1—C10	1.309 (6)	C11—H11B	0.9600
N1—N2	1.379 (5)	C11—H11C	0.9600
N1—C8	1.445 (6)	C12—C13	1.500 (7)
F1—C3	1.368 (6)	C12—H12A	0.9700
C1—C2	1.386 (7)	C12—H12B	0.9700
C1—C6	1.392 (7)	C13—C14	1.507 (7)
C1—H1A	0.9300	C13—H13A	0.9700
O2—C15	1.352 (6)	C13—H13B	0.9700
O2—C14	1.430 (6)	C14—H14A	0.9700
F2—C5	1.347 (6)	C14—H14B	0.9700
N2—C9	1.304 (6)	C15—C20	1.383 (7)
C2—C3	1.346 (8)	C15—C16	1.391 (7)
C2—H2B	0.9300	C16—C17	1.368 (7)
N3—C10	1.300 (6)	C16—H16A	0.9300
N3—C9	1.303 (6)	C17—C18	1.395 (8)
N3—H3A	0.8600	C17—H17A	0.9300
C3—C4	1.375 (8)	C18—C19	1.374 (7)
C4—C5	1.363 (8)	C19—C20	1.356 (7)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.382 (7)	C20—H20A	0.9300
C6—C7	1.476 (7)	O4—N4	1.259 (5)
C7—C8	1.327 (7)	N4—O5	1.219 (5)
C8—C11	1.504 (7)	N4—O3	1.235 (5)

C7—O1—C12	118.7 (4)	C8—C11—H11C	109.5
C10—N1—N2	110.9 (4)	H11A—C11—H11C	109.5
C10—N1—C8	128.3 (4)	H11B—C11—H11C	109.5
N2—N1—C8	120.8 (4)	O1—C12—C13	107.4 (4)
C2—C1—C6	122.1 (5)	O1—C12—H12A	110.2
C2—C1—H1A	119.0	C13—C12—H12A	110.2
C6—C1—H1A	119.0	O1—C12—H12B	110.2
C15—O2—C14	117.2 (4)	C13—C12—H12B	110.2
C9—N2—N1	103.0 (4)	H12A—C12—H12B	108.5
C3—C2—C1	117.5 (6)	C12—C13—C14	112.4 (4)
C3—C2—H2B	121.3	C12—C13—H13A	109.1
C1—C2—H2B	121.3	C14—C13—H13A	109.1
C10—N3—C9	110.5 (4)	C12—C13—H13B	109.1
C10—N3—H3A	124.8	C14—C13—H13B	109.1
C9—N3—H3A	124.8	H13A—C13—H13B	107.9
C2—C3—F1	118.0 (6)	O2—C14—C13	107.9 (4)
C2—C3—C4	124.0 (6)	O2—C14—H14A	110.1
F1—C3—C4	118.0 (6)	C13—C14—H14A	110.1
C5—C4—C3	116.3 (6)	O2—C14—H14B	110.1
C5—C4—H4A	121.9	C13—C14—H14B	110.1
C3—C4—H4A	121.9	H14A—C14—H14B	108.4
F2—C5—C4	118.2 (5)	O2—C15—C20	125.7 (5)
F2—C5—C6	117.8 (5)	O2—C15—C16	116.1 (5)
C4—C5—C6	124.0 (6)	C20—C15—C16	118.1 (5)
C5—C6—C1	116.0 (5)	C17—C16—C15	121.1 (5)
C5—C6—C7	122.3 (5)	C17—C16—H16A	119.4
C1—C6—C7	121.7 (5)	C15—C16—H16A	119.4
C8—C7—O1	118.6 (4)	C16—C17—C18	119.4 (5)
C8—C7—C6	122.5 (5)	C16—C17—H17A	120.3
O1—C7—C6	118.8 (4)	C18—C17—H17A	120.3
C7—C8—N1	117.9 (4)	C19—C18—C17	119.6 (5)
C7—C8—C11	127.8 (5)	C19—C18—Br	120.1 (4)
N1—C8—C11	114.4 (4)	C17—C18—Br	120.3 (4)
N3—C9—N2	110.4 (5)	C20—C19—C18	120.5 (5)
N3—C9—H9A	124.8	C20—C19—H19A	119.7
N2—C9—H9A	124.8	C18—C19—H19A	119.7
N3—C10—N1	105.2 (4)	C19—C20—C15	121.3 (5)
N3—C10—H10A	127.4	C19—C20—H20A	119.4
N1—C10—H10A	127.4	C15—C20—H20A	119.4
C8—C11—H11A	109.5	O5—N4—O3	121.9 (5)
C8—C11—H11B	109.5	O5—N4—O4	120.4 (5)
H11A—C11—H11B	109.5	O3—N4—O4	117.7 (5)

C10—N1—N2—C9	−1.1 (5)	C10—N1—C8—C7	55.1 (7)
C8—N1—N2—C9	−179.7 (4)	N2—N1—C8—C7	−126.5 (5)
C6—C1—C2—C3	−0.2 (9)	C10—N1—C8—C11	−126.2 (5)
C1—C2—C3—F1	−179.8 (5)	N2—N1—C8—C11	52.2 (6)
C1—C2—C3—C4	3.1 (10)	C10—N3—C9—N2	0.0 (6)
C2—C3—C4—C5	−3.4 (10)	N1—N2—C9—N3	0.6 (6)
F1—C3—C4—C5	179.6 (6)	C9—N3—C10—N1	−0.7 (5)
C3—C4—C5—F2	−178.2 (6)	N2—N1—C10—N3	1.1 (5)
C3—C4—C5—C6	0.6 (10)	C8—N1—C10—N3	179.6 (4)
F2—C5—C6—C1	−179.2 (5)	C7—O1—C12—C13	−179.3 (4)
C4—C5—C6—C1	2.0 (9)	O1—C12—C13—C14	−68.8 (6)
F2—C5—C6—C7	1.8 (8)	C15—O2—C14—C13	179.2 (4)
C4—C5—C6—C7	−177.0 (6)	C12—C13—C14—O2	180.0 (4)
C2—C1—C6—C5	−2.2 (8)	C14—O2—C15—C20	−2.6 (7)
C2—C1—C6—C7	176.7 (5)	C14—O2—C15—C16	178.6 (4)
C12—O1—C7—C8	−158.1 (5)	O2—C15—C16—C17	178.8 (5)
C12—O1—C7—C6	21.7 (6)	C20—C15—C16—C17	−0.1 (8)
C5—C6—C7—C8	−113.0 (6)	C15—C16—C17—C18	−0.2 (8)
C1—C6—C7—C8	68.1 (7)	C16—C17—C18—C19	0.2 (8)
C5—C6—C7—O1	67.2 (7)	C16—C17—C18—Br	179.5 (4)
C1—C6—C7—O1	−111.7 (6)	C17—C18—C19—C20	0.1 (8)
O1—C7—C8—N1	7.3 (7)	Br—C18—C19—C20	−179.3 (4)
C6—C7—C8—N1	−172.5 (4)	C18—C19—C20—C15	−0.3 (9)
O1—C7—C8—C11	−171.2 (5)	O2—C15—C20—C19	−178.5 (5)
C6—C7—C8—C11	9.0 (9)	C16—C15—C20—C19	0.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.86	1.95	2.790 (6)	167
C9—H9A···O3ⁱ	0.93	2.55	3.271 (7)	135
C10—H10A···O3ⁱⁱ	0.93	2.49	3.263 (7)	140
C10—H10A···O5ⁱⁱ	0.93	2.42	3.340 (7)	168
C19—H19A···O3	0.93	2.54	3.276 (7)	137

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉BrF₂N₃O₂⁺·NO₃⁻
M_r	513.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3030 (17), 8.4260 (17), 16.170 (3)
α, β, γ (°)	91.10 (3), 95.80 (3), 102.30 (3)
V (Å³)	1098.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.699, 0.831
No. of measured, independent and observed [I > 2σ(I)] reflections	4329, 4029, 2250
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.152, 1.01
No. of reflections	4029
No. of parameters	289
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.47

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
N3—H3A···O4	0.86	1.95	2.790 (6)	167
C9—H9A···O3ⁱ	0.93	2.55	3.271 (7)	135
C10—H10A···O3ⁱⁱ	0.93	2.49	3.263 (7)	140
C10—H10A···O5ⁱⁱ	0.93	2.42	3.340 (7)	168
C19—H19A···O3	0.93	2.54	3.276 (7)	137

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

Acknowledgements

This research work was supported by the Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 20113221110005).

References

Enraf–Nonius (1994). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fromtling, R. & Castaner, J. (1996). Drugs Fut. 21, 160–166. CAS Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Jeu, L., Piacenti, F. J., Lyakhovetskiy, A. G. & Fung, H. B. (2003). Clin. Ther. 25, 1321–1381. Web of Science CrossRef PubMed CAS Google Scholar
Ludwig, Z. & Kurt, T. (1985). US Patent Appl. US4554356. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

1-{(Z)-1-[3-(4-Bromo­phen­­oxy)prop­­oxy]-1-(2,4-di­fluoro­phen­yl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{(Z)-1-[3-(4-Bromophenoxy)propoxy]-1-(2,4-difluorophenyl)prop-1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate