1-[(Z)-8-(4-Chlorophenoxy)-3-(2,4-di­fluorophenyl)-4-oxaocta-2-en-2-yl]-1H-1,2,4-triazol-4-ium nitrate

Chen, J.; Wang, K.; Shen, Y.; Ren, L.; Chen, G.

doi:10.1107/S1600536811038761

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2800

https://doi.org/10.1107/S1600536811038761

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1-[(Z)-8-(4-Chlorophenoxy)-3-(2,4-difluorophenyl)-4-oxaocta-2-en-2-yl]-1H-1,2,4-triazol-4-ium nitrate

Jian-long Chen,^a ^* Kai Wang,^b Yan Shen,^a Li-li Ren ^a and Guo-guang Chen ^a

^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: guoguangchen@163.com

(Received 7 September 2011; accepted 21 September 2011; online 30 September 2011)

In the title compound C₂₁H₂₁ClF₂N₃O₂⁺·NO₃⁻, the triazole ring makes dihedral angles of 40.7 (3) and 30.2 (4)° with the 4-chloropheny and 2,4-difluorophenyl rings, respectively. The cation adopts a Z-configuration about the C=C double bond which links the triazole ring to the 4-chlorophenoxy unit via a butyloxy chain. In the crystal, the cations and the anions are linked by N—H⋯O, C—H⋯O and C—H⋯F hydrogen bonding.

Related literature

For the antifungal activity of related compounds, see: Jeu et al. (2003 ). For details of the synthesis, see: Ludwig & Kurt (1985 ). For a related structure, see: Kurt et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₁ClF₂N₃O₂⁺·NO₃⁻
M_r = 482.87
Monoclinic, P 2₁ /c
a = 7.9580 (16) Å
b = 31.635 (6) Å
c = 9.1850 (18) Å
β = 97.29 (3)°
V = 2293.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.936, T_max = 0.978
4521 measured reflections
4216 independent reflections
1952 reflections with I > 2σ(I)
R_int = 0.092
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.140
S = 1.00
4216 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5	0.86	1.80	2.659 (4)	174
C9—H9A⋯F1ⁱ	0.96	2.53	3.371 (5)	146
C10—H10A⋯O4ⁱⁱ	0.93	2.28	3.033 (5)	137
C1—H1A⋯O3ⁱⁱⁱ	0.93	2.57	3.434 (5)	155
C11—H11A⋯O5ⁱⁱⁱ	0.93	2.25	3.180 (5)	174
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811038761/pv2445sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038761/pv2445Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038761/pv2445Isup3.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) As part of our studies on the synthesis of new triazole derivatives, the crystal structure of the title compound, having similar structure with omoconazol (Kurt et al., 1987), was determined.

In the title compound (Fig. 1), the cation adopts a Z conformation about the C═C double bond. In the crystal structure the anions and cations are connected via N—H···O, C—H···O and C—H···F hydrogen bonding (Table 1 and Fig. 2).

Related literature top

For the antifungal activity of related compounds, see: Jeu et al. (2003). For details of the synthesis, see: Ludwig & Kurt (1985). For a related structure, see: Kurt et al. (1987).

Experimental top

1-(2,4-Difluorophenyl)-2-(1,2,4-triazol)-1-y1)propan-1-one (3.0 g, 0.01 mol) 10 g of a 50% aqueous sodium hydroxide, toluene (15 ml) and 1.5 ml of a 40% aqueous solution of tetrabutyl ammonium hydroxide were mixed and heated to 323 K under vigorous stirring. 1-Bromo-4-(4-chlorophenoxy)-butane (2.6 g, 0.01 mol) dissolved in 10 ml toluene, was instilled into the stirred and warmed solution in the course of 10 h. The mixture was subsequently stirred for another 20 h at 323 K. The reaction mixture was mixed with as much water and chloroform so that the aqueous phase becomes lighter than the organic phase. Thereafter, the organic and aqueous phases were separated. The organic phase was dried with sodium sulfate. The solvents were distilled under reduced pressure. The remaining residue was a dark oil that was diluted with 10 ml 2-propanol and then adjusted to a pH-value of 2 by 30% aqueous nitric acid. The resulting nitric acid solution was then cooled in the refrigerator. The impure precipitated product herein was subsequently crystallized from a 1:1 mixture of ethyl acetate and ethanol. The purified product was analytically identified as an approximately pure Z-isomer of the title compound. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. Details on the synthesis can be found in the literature (Ludwig & Kurt, 1985).

Structure description top

For the antifungal activity of related compounds, see: Jeu et al. (2003). For details of the synthesis, see: Ludwig & Kurt (1985). For a related structure, see: Kurt et al. (1987).

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 compound, with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.
	Fig. 2. The packing diagram of the title compound. Hydron bonds are shown as dashed lines.

1-[(Z)-8-(4-Chlorophenoxy)-3-(2,4-difluorophenyl)-4-oxaocta- 2-en-2-yl]-1H-1,2,4-triazol-4-ium nitrate top

Crystal data top

C₂₁H₂₁ClF₂N₃O₂⁺·NO₃⁻	F(000) = 1000
M_r = 482.87	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.9580 (16) Å	θ = 9–12°
b = 31.635 (6) Å	µ = 0.22 mm⁻¹
c = 9.1850 (18) Å	T = 293 K
β = 97.29 (3)°	Block, yellow
V = 2293.6 (8) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1952 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.092
Graphite monochromator	θ_max = 25.4°, θ_min = 1.3°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→38
T_min = 0.936, T_max = 0.978	l = −11→10
4521 measured reflections	3 standard reflections every 200 reflections
4216 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.048P)²] where P = (F_o² + 2F_c²)/3
4216 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₁ClF₂N₃O₂⁺·NO₃⁻	V = 2293.6 (8) Å³
M_r = 482.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9580 (16) Å	µ = 0.22 mm⁻¹
b = 31.635 (6) Å	T = 293 K
c = 9.1850 (18) Å	0.30 × 0.10 × 0.10 mm
β = 97.29 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1952 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.092
T_min = 0.936, T_max = 0.978	3 standard reflections every 200 reflections
4521 measured reflections	intensity decay: 1%
4216 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
4216 reflections	Δρ_min = −0.24 e Å⁻³
298 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
Cl	1.06795 (17)	0.98117 (4)	0.78129 (14)	0.0884 (4)
O1	0.5208 (3)	0.66925 (8)	0.7812 (2)	0.0537 (7)
N1	0.4023 (4)	0.64572 (10)	0.5034 (3)	0.0492 (8)
F1	0.6286 (3)	0.51310 (8)	1.2146 (3)	0.0929 (9)
C1	0.4331 (5)	0.59449 (12)	0.9814 (4)	0.0600 (11)
H1A	0.3389	0.6121	0.9757	0.072*
O2	0.8631 (4)	0.80660 (8)	0.8732 (3)	0.0665 (8)
F2	0.7867 (3)	0.57220 (8)	0.7858 (3)	0.0912 (9)
N2	0.4433 (5)	0.63841 (11)	0.3638 (3)	0.0667 (10)
C2	0.4625 (6)	0.56669 (14)	1.0964 (4)	0.0680 (13)
H2B	0.3904	0.5656	1.1684	0.082*
N3	0.3111 (4)	0.69903 (10)	0.3756 (3)	0.0534 (9)
H3A	0.2657	0.7229	0.3485	0.064*
C3	0.5993 (7)	0.54084 (13)	1.1027 (4)	0.0622 (12)
C4	0.7106 (6)	0.54183 (13)	0.9996 (4)	0.0668 (12)
H4A	0.8045	0.5241	1.0054	0.080*
C5	0.6748 (6)	0.57053 (13)	0.8877 (4)	0.0569 (11)
C6	0.5399 (5)	0.59716 (12)	0.8733 (4)	0.0463 (10)
C7	0.5057 (5)	0.62726 (12)	0.7499 (4)	0.0444 (9)
C8	0.4462 (5)	0.61470 (11)	0.6153 (4)	0.0498 (10)
C9	0.4189 (6)	0.57050 (13)	0.5668 (4)	0.0864 (16)
H9A	0.4507	0.5518	0.6480	0.130*
H9B	0.4867	0.5645	0.4899	0.130*
H9C	0.3014	0.5664	0.5307	0.130*
C10	0.3847 (6)	0.67162 (14)	0.2922 (4)	0.0652 (12)
H10A	0.3928	0.6760	0.1932	0.078*
C11	0.3222 (5)	0.68190 (12)	0.5088 (4)	0.0506 (10)
H11A	0.2811	0.6934	0.5905	0.061*
C12	0.6628 (5)	0.68174 (11)	0.8866 (4)	0.0484 (10)
H12A	0.7679	0.6721	0.8546	0.058*
H12B	0.6527	0.6691	0.9813	0.058*
C13	0.6635 (5)	0.72830 (11)	0.8991 (4)	0.0528 (10)
H13A	0.5584	0.7374	0.9325	0.063*
H13B	0.6681	0.7405	0.8028	0.063*
C14	0.8110 (5)	0.74505 (12)	1.0040 (4)	0.0503 (10)
H14A	0.8013	0.7342	1.1014	0.060*
H14B	0.9152	0.7339	0.9746	0.060*
C15	0.8246 (5)	0.79196 (12)	1.0125 (4)	0.0542 (10)
H15A	0.7186	0.8041	1.0342	0.065*
H15B	0.9135	0.8002	1.0895	0.065*
C16	0.9051 (5)	0.84798 (12)	0.8603 (4)	0.0526 (10)
C17	0.9642 (5)	0.85865 (13)	0.7305 (4)	0.0591 (11)
H17A	0.9710	0.8380	0.6593	0.071*
C18	1.0133 (5)	0.89934 (14)	0.7049 (4)	0.0617 (11)
H18A	1.0538	0.9062	0.6172	0.074*
C19	1.0020 (5)	0.93006 (13)	0.8108 (5)	0.0617 (11)
C20	0.9427 (6)	0.91986 (14)	0.9391 (5)	0.0724 (13)
H20A	0.9355	0.9405	1.0100	0.087*
C21	0.8929 (5)	0.87874 (13)	0.9644 (4)	0.0667 (12)
H21A	0.8514	0.8720	1.0517	0.080*
N4	0.1836 (4)	0.79947 (13)	0.3777 (4)	0.0604 (9)
O3	0.1244 (4)	0.83434 (11)	0.3510 (4)	0.0941 (11)
O4	0.2476 (4)	0.78801 (11)	0.5018 (3)	0.0883 (11)
O5	0.1781 (3)	0.77208 (8)	0.2747 (3)	0.0588 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.1080 (10)	0.0611 (8)	0.0955 (9)	−0.0204 (7)	0.0108 (7)	0.0053 (7)
O1	0.0688 (19)	0.0470 (16)	0.0404 (14)	−0.0018 (13)	−0.0116 (13)	−0.0013 (12)
N1	0.066 (2)	0.046 (2)	0.0340 (17)	0.0003 (17)	−0.0015 (15)	0.0002 (15)
F1	0.126 (2)	0.0812 (19)	0.0663 (16)	−0.0072 (17)	−0.0075 (15)	0.0369 (14)
C1	0.075 (3)	0.054 (3)	0.052 (2)	0.003 (2)	0.011 (2)	0.010 (2)
O2	0.102 (2)	0.0489 (18)	0.0517 (17)	−0.0183 (16)	0.0205 (15)	−0.0070 (14)
F2	0.090 (2)	0.106 (2)	0.0833 (18)	0.0335 (17)	0.0354 (16)	0.0291 (15)
N2	0.095 (3)	0.072 (3)	0.0321 (18)	0.014 (2)	0.0053 (18)	−0.0024 (17)
C2	0.094 (4)	0.066 (3)	0.047 (3)	−0.008 (3)	0.021 (2)	0.011 (2)
N3	0.067 (2)	0.051 (2)	0.0388 (18)	−0.0046 (18)	−0.0070 (16)	0.0064 (16)
C3	0.098 (4)	0.045 (3)	0.040 (2)	−0.009 (3)	−0.006 (2)	0.0116 (19)
C4	0.082 (3)	0.061 (3)	0.054 (3)	0.016 (2)	−0.004 (2)	0.007 (2)
C5	0.077 (3)	0.056 (3)	0.039 (2)	0.001 (2)	0.011 (2)	−0.001 (2)
C6	0.058 (3)	0.045 (2)	0.034 (2)	0.002 (2)	0.0029 (19)	0.0002 (17)
C7	0.051 (2)	0.039 (2)	0.041 (2)	−0.0049 (18)	−0.0012 (17)	−0.0023 (17)
C8	0.069 (3)	0.040 (2)	0.038 (2)	−0.001 (2)	−0.0001 (19)	0.0038 (18)
C9	0.132 (5)	0.057 (3)	0.062 (3)	−0.017 (3)	−0.022 (3)	−0.003 (2)
C10	0.093 (4)	0.066 (3)	0.035 (2)	0.001 (3)	0.000 (2)	0.001 (2)
C11	0.059 (3)	0.054 (3)	0.036 (2)	−0.007 (2)	−0.0015 (18)	0.0002 (19)
C12	0.049 (2)	0.051 (2)	0.043 (2)	−0.002 (2)	−0.0027 (18)	−0.0036 (18)
C13	0.063 (3)	0.047 (3)	0.047 (2)	−0.006 (2)	−0.0001 (19)	−0.0017 (19)
C14	0.045 (2)	0.057 (3)	0.048 (2)	−0.001 (2)	0.0024 (19)	−0.0049 (19)
C15	0.057 (3)	0.056 (3)	0.048 (2)	−0.003 (2)	−0.0002 (19)	−0.008 (2)
C16	0.057 (3)	0.050 (3)	0.051 (2)	−0.008 (2)	0.010 (2)	0.000 (2)
C17	0.067 (3)	0.054 (3)	0.056 (3)	−0.002 (2)	0.005 (2)	−0.008 (2)
C18	0.063 (3)	0.066 (3)	0.057 (3)	−0.004 (2)	0.010 (2)	0.003 (2)
C19	0.069 (3)	0.050 (3)	0.066 (3)	−0.011 (2)	0.006 (2)	0.001 (2)
C20	0.093 (4)	0.052 (3)	0.075 (3)	−0.014 (3)	0.022 (3)	−0.020 (2)
C21	0.087 (3)	0.059 (3)	0.059 (3)	−0.024 (2)	0.030 (2)	−0.018 (2)
N4	0.055 (2)	0.075 (3)	0.053 (2)	−0.007 (2)	0.0119 (18)	−0.002 (2)
O3	0.089 (3)	0.062 (2)	0.132 (3)	0.011 (2)	0.014 (2)	−0.007 (2)
O4	0.097 (2)	0.130 (3)	0.0366 (17)	−0.010 (2)	0.0009 (16)	−0.0060 (18)
O5	0.077 (2)	0.0595 (18)	0.0377 (14)	−0.0015 (15)	0.0004 (13)	−0.0056 (14)

Geometric parameters (Å, º) top

Cl—C19	1.732 (4)	C9—H9C	0.9600
O1—C7	1.361 (4)	C10—H10A	0.9300
O1—C12	1.447 (4)	C11—H11A	0.9300
N1—C11	1.314 (4)	C12—C13	1.477 (4)
N1—N2	1.383 (4)	C12—H12A	0.9700
N1—C8	1.432 (4)	C12—H12B	0.9700
F1—C3	1.349 (4)	C13—C14	1.517 (5)
C1—C2	1.371 (5)	C13—H13A	0.9700
C1—C6	1.389 (5)	C13—H13B	0.9700
C1—H1A	0.9300	C14—C15	1.489 (5)
O2—C16	1.360 (4)	C14—H14A	0.9700
O2—C15	1.430 (4)	C14—H14B	0.9700
F2—C5	1.372 (4)	C15—H15A	0.9700
N2—C10	1.295 (5)	C15—H15B	0.9700
C2—C3	1.357 (6)	C16—C21	1.376 (5)
C2—H2B	0.9300	C16—C17	1.378 (5)
N3—C11	1.330 (4)	C17—C18	1.374 (5)
N3—C10	1.340 (5)	C17—H17A	0.9300
N3—H3A	0.8600	C18—C19	1.386 (5)
C3—C4	1.377 (6)	C18—H18A	0.9300
C4—C5	1.374 (5)	C19—C20	1.362 (5)
C4—H4A	0.9300	C20—C21	1.388 (5)
C5—C6	1.358 (5)	C20—H20A	0.9300
C6—C7	1.479 (5)	C21—H21A	0.9300
C7—C8	1.327 (5)	N4—O3	1.212 (4)
C8—C9	1.475 (5)	N4—O4	1.243 (4)
C9—H9A	0.9600	N4—O5	1.279 (4)
C9—H9B	0.9600

C7—O1—C12	116.6 (3)	O1—C12—C13	108.6 (3)
C11—N1—N2	110.7 (3)	O1—C12—H12A	110.0
C11—N1—C8	130.2 (3)	C13—C12—H12A	110.0
N2—N1—C8	119.1 (3)	O1—C12—H12B	110.0
C2—C1—C6	122.0 (4)	C13—C12—H12B	110.0
C2—C1—H1A	119.0	H12A—C12—H12B	108.3
C6—C1—H1A	119.0	C12—C13—C14	113.1 (3)
C16—O2—C15	118.2 (3)	C12—C13—H13A	109.0
C10—N2—N1	102.9 (3)	C14—C13—H13A	109.0
C3—C2—C1	118.5 (4)	C12—C13—H13B	109.0
C3—C2—H2B	120.8	C14—C13—H13B	109.0
C1—C2—H2B	120.8	H13A—C13—H13B	107.8
C11—N3—C10	106.2 (3)	C15—C14—C13	115.2 (3)
C11—N3—H3A	126.9	C15—C14—H14A	108.5
C10—N3—H3A	126.9	C13—C14—H14A	108.5
F1—C3—C2	119.0 (4)	C15—C14—H14B	108.5
F1—C3—C4	118.3 (4)	C13—C14—H14B	108.5
C2—C3—C4	122.7 (4)	H14A—C14—H14B	107.5
C5—C4—C3	116.0 (4)	O2—C15—C14	107.3 (3)
C5—C4—H4A	122.0	O2—C15—H15A	110.2
C3—C4—H4A	122.0	C14—C15—H15A	110.2
C6—C5—F2	118.9 (3)	O2—C15—H15B	110.2
C6—C5—C4	124.7 (4)	C14—C15—H15B	110.2
F2—C5—C4	116.4 (4)	H15A—C15—H15B	108.5
C5—C6—C1	116.1 (4)	O2—C16—C21	125.5 (4)
C5—C6—C7	122.7 (3)	O2—C16—C17	115.2 (3)
C1—C6—C7	121.2 (4)	C21—C16—C17	119.3 (4)
C8—C7—O1	120.0 (3)	C18—C17—C16	120.9 (4)
C8—C7—C6	122.0 (3)	C18—C17—H17A	119.5
O1—C7—C6	117.6 (3)	C16—C17—H17A	119.5
C7—C8—N1	119.3 (3)	C17—C18—C19	119.4 (4)
C7—C8—C9	125.9 (3)	C17—C18—H18A	120.3
N1—C8—C9	114.8 (3)	C19—C18—H18A	120.3
C8—C9—H9A	109.5	C20—C19—C18	120.1 (4)
C8—C9—H9B	109.5	C20—C19—Cl	120.1 (3)
H9A—C9—H9B	109.5	C18—C19—Cl	119.8 (3)
C8—C9—H9C	109.5	C19—C20—C21	120.3 (4)
H9A—C9—H9C	109.5	C19—C20—H20A	119.9
H9B—C9—H9C	109.5	C21—C20—H20A	119.9
N2—C10—N3	113.0 (4)	C16—C21—C20	120.0 (4)
N2—C10—H10A	123.5	C16—C21—H21A	120.0
N3—C10—H10A	123.5	C20—C21—H21A	120.0
N1—C11—N3	107.2 (3)	O3—N4—O4	123.7 (4)
N1—C11—H11A	126.4	O3—N4—O5	119.4 (4)
N3—C11—H11A	126.4	O4—N4—O5	116.9 (4)

C11—N1—N2—C10	0.3 (4)	N2—N1—C8—C7	139.3 (4)
C8—N1—N2—C10	179.2 (3)	C11—N1—C8—C9	137.7 (4)
C6—C1—C2—C3	−0.8 (6)	N2—N1—C8—C9	−40.9 (5)
C1—C2—C3—F1	−179.4 (4)	N1—N2—C10—N3	0.2 (5)
C1—C2—C3—C4	0.9 (7)	C11—N3—C10—N2	−0.6 (5)
F1—C3—C4—C5	179.8 (3)	N2—N1—C11—N3	−0.7 (4)
C2—C3—C4—C5	−0.5 (6)	C8—N1—C11—N3	−179.4 (3)
C3—C4—C5—C6	0.0 (6)	C10—N3—C11—N1	0.8 (4)
C3—C4—C5—F2	179.0 (3)	C7—O1—C12—C13	176.6 (3)
F2—C5—C6—C1	−178.8 (3)	O1—C12—C13—C14	−178.3 (3)
C4—C5—C6—C1	0.2 (6)	C12—C13—C14—C15	175.8 (3)
F2—C5—C6—C7	1.6 (6)	C16—O2—C15—C14	−171.0 (3)
C4—C5—C6—C7	−179.4 (4)	C13—C14—C15—O2	−66.4 (4)
C2—C1—C6—C5	0.3 (6)	C15—O2—C16—C21	−8.9 (6)
C2—C1—C6—C7	179.8 (4)	C15—O2—C16—C17	171.0 (3)
C12—O1—C7—C8	−145.4 (4)	O2—C16—C17—C18	−179.0 (4)
C12—O1—C7—C6	41.0 (4)	C21—C16—C17—C18	1.0 (6)
C5—C6—C7—C8	74.0 (5)	C16—C17—C18—C19	−0.5 (6)
C1—C6—C7—C8	−105.6 (5)	C17—C18—C19—C20	0.1 (6)
C5—C6—C7—O1	−112.6 (4)	C17—C18—C19—Cl	178.6 (3)
C1—C6—C7—O1	67.8 (5)	C18—C19—C20—C21	−0.2 (7)
O1—C7—C8—N1	1.5 (6)	Cl—C19—C20—C21	−178.7 (4)
C6—C7—C8—N1	174.8 (3)	O2—C16—C21—C20	178.9 (4)
O1—C7—C8—C9	−178.3 (4)	C17—C16—C21—C20	−1.1 (6)
C6—C7—C8—C9	−5.0 (7)	C19—C20—C21—C16	0.7 (7)
C11—N1—C8—C7	−42.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5	0.86	1.80	2.659 (4)	174
C9—H9A···F1ⁱ	0.96	2.53	3.371 (5)	146
C10—H10A···O4ⁱⁱ	0.93	2.28	3.033 (5)	137
C1—H1A···O3ⁱⁱⁱ	0.93	2.57	3.434 (5)	155
C11—H11A···O5ⁱⁱⁱ	0.93	2.25	3.180 (5)	174

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁ClF₂N₃O₂⁺·NO₃⁻
M_r	482.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9580 (16), 31.635 (6), 9.1850 (18)
β (°)	97.29 (3)
V (Å³)	2293.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.936, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	4521, 4216, 1952
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.140, 1.00
No. of reflections	4216
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

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···O5	0.86	1.80	2.659 (4)	174
C9—H9A···F1ⁱ	0.96	2.53	3.371 (5)	146
C10—H10A···O4ⁱⁱ	0.93	2.28	3.033 (5)	137
C1—H1A···O3ⁱⁱⁱ	0.93	2.57	3.434 (5)	155
C11—H11A···O5ⁱⁱⁱ	0.93	2.25	3.180 (5)	174

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2.

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
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
Kurt, T., Ludwing, Z., Max, H. P., Martin, E. & Max, D. (1987). Helv. Chim. Acta 70, 441–444. 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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Volume 67| Part 10| October 2011| Page o2800

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

1-[(Z)-8-(4-Chloro­phen­oxy)-3-(2,4-di­fluoro­phenyl)-4-oxa­octa-2-en-2-yl]-1H-1,2,4-triazol-4-ium nitrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

1-[(Z)-8-(4-Chlorophenoxy)-3-(2,4-difluorophenyl)-4-oxaocta-2-en-2-yl]-1H-1,2,4-triazol-4-ium nitrate