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

Wan, W.; Wang, K.; Hu, Y.; Shen, F.; Yang, W.

doi:10.1107/S1600536811034933

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2617

https://doi.org/10.1107/S1600536811034933

Open

access

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 and Wen-ge Yang ^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
^*Correspondence e-mail: yonghonghu09@gmail.com

(Received 20 July 2011; accepted 25 August 2011; online 14 September 2011)

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, C 2/c
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[F² > 2σ(F²)] = 0.064
wR(F²) = 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

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
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (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/S1600536811034933/nc2240sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811034933/nc2240Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811034933/nc2240Isup3.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 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).

Related literature top

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 top

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.

Structure description top

For the use of triazole derivatives as antifungal agents, see: Jeu et al. (2003); Fromtling & Castaner (1996). For the synthesis, see: Zirngibl & Thiele (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 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-{(1Z)-1-[6-(4-Chlorophenoxy)hexyloxy]-1-(2,4-difluorophenyl)prop- 1-en-2-yl}-1H-1,2,4-triazol-4-ium nitrate top

Crystal data top

C₂₃H₂₅ClF₂N₃O₂⁺·NO₃⁻	F(000) = 2128
M_r = 510.92	D_x = 1.355 Mg m⁻³
Monoclinic, C2/c	Melting point: 383.15 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 35.538 (7) Å	Cell parameters from 25 reflections
b = 8.5550 (17) Å	θ = 9–13°
c = 17.072 (3) Å	µ = 0.21 mm⁻¹
β = 105.21 (3)°	T = 293 K
V = 5008.6 (17) Å³	Block, yellow
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
Graphite monochromator	θ_max = 25.5°, θ_min = 1.2°
ω/2θ scans	h = −42→42
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
T_min = 0.940, T_max = 0.980	l = −20→20
9194 measured reflections	3 standard reflections every 200 reflections
4628 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.068P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4628 reflections	Δρ_max = 0.18 e Å⁻³
317 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (3)

Crystal data top

C₂₃H₂₅ClF₂N₃O₂⁺·NO₃⁻	V = 5008.6 (17) Å³
M_r = 510.92	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 35.538 (7) Å	µ = 0.21 mm⁻¹
b = 8.5550 (17) Å	T = 293 K
c = 17.072 (3) Å	0.30 × 0.20 × 0.10 mm
β = 105.21 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1954 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.063
T_min = 0.940, T_max = 0.980	3 standard reflections every 200 reflections
9194 measured reflections	intensity decay: 1%
4628 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
4628 reflections	Δρ_min = −0.18 e Å⁻³
317 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	0.24234 (4)	0.19455 (19)	0.11286 (9)	0.1265 (6)
N1	0.60062 (8)	0.8994 (3)	0.62210 (18)	0.0581 (8)
O1	0.39276 (8)	0.4929 (4)	0.25522 (17)	0.0823 (9)
F1	0.73827 (8)	0.7269 (3)	0.34649 (16)	0.1146 (10)
C1	0.32631 (12)	0.4430 (5)	0.2609 (2)	0.0796 (13)
H1A	0.3293	0.5017	0.3080	0.096*
O2	0.58960 (7)	0.7156 (3)	0.48863 (16)	0.0806 (9)
F2	0.68002 (7)	0.5624 (3)	0.54599 (15)	0.1046 (9)
N2	0.61212 (9)	0.9274 (4)	0.70427 (19)	0.0790 (10)
C2	0.29134 (12)	0.3703 (6)	0.2254 (3)	0.0834 (13)
H2B	0.2707	0.3798	0.2493	0.100*
N3	0.54892 (9)	0.8995 (4)	0.6624 (2)	0.0728 (10)
H3A	0.5249	0.8934	0.6638	0.087*
C3	0.28647 (12)	0.2854 (6)	0.1564 (3)	0.0805 (13)
C4	0.31692 (13)	0.2685 (5)	0.1204 (3)	0.0774 (12)
H4A	0.3137	0.2095	0.0734	0.093*
C5	0.35210 (11)	0.3405 (5)	0.1553 (2)	0.0693 (11)
H5A	0.3727	0.3306	0.1314	0.083*
C6	0.35694 (11)	0.4270 (5)	0.2254 (2)	0.0666 (11)
C7	0.39858 (12)	0.5892 (6)	0.3251 (3)	0.0944 (14)
H7A	0.3968	0.5268	0.3714	0.113*
H7B	0.3786	0.6692	0.3162	0.113*
C8	0.43785 (13)	0.6638 (6)	0.3416 (3)	0.1040 (16)
H8A	0.4391	0.7249	0.2945	0.125*
H8B	0.4406	0.7357	0.3867	0.125*
C9	0.47111 (12)	0.5551 (6)	0.3607 (3)	0.0940 (15)
H9A	0.4698	0.4879	0.3143	0.113*
H9B	0.4695	0.4895	0.4060	0.113*
C10	0.51068 (13)	0.6424 (6)	0.3825 (3)	0.1051 (16)
H10A	0.5125	0.7054	0.3364	0.126*
H10B	0.5114	0.7126	0.4275	0.126*
C11	0.54449 (13)	0.5380 (6)	0.4046 (3)	0.1036 (16)
H11A	0.5423	0.4622	0.3613	0.124*
H11B	0.5435	0.4810	0.4531	0.124*
C12	0.58357 (12)	0.6168 (6)	0.4198 (3)	0.1026 (16)
H12A	0.6040	0.5384	0.4288	0.123*
H12B	0.5847	0.6779	0.3726	0.123*
C13	0.62371 (10)	0.7959 (5)	0.5136 (2)	0.0553 (9)
C14	0.65339 (10)	0.7764 (5)	0.4670 (2)	0.0562 (10)
C15	0.65451 (12)	0.8748 (5)	0.4041 (2)	0.0796 (12)
H15A	0.6361	0.9540	0.3894	0.095*
C16	0.68307 (14)	0.8571 (6)	0.3618 (3)	0.0880 (14)
H16A	0.6835	0.9218	0.3182	0.106*
C17	0.71014 (12)	0.7424 (6)	0.3862 (3)	0.0754 (13)
C18	0.71030 (11)	0.6422 (5)	0.4471 (3)	0.0742 (12)
H18A	0.7289	0.5638	0.4622	0.089*
C19	0.68107 (11)	0.6632 (5)	0.4859 (2)	0.0638 (11)
C20	0.62999 (10)	0.8855 (5)	0.5780 (2)	0.0584 (10)
C21	0.66594 (11)	0.9797 (6)	0.6133 (3)	0.0979 (16)
H21A	0.6842	0.9647	0.5813	0.147*
H21B	0.6775	0.9464	0.6680	0.147*
H21C	0.6592	1.0883	0.6131	0.147*
C22	0.57978 (13)	0.9257 (5)	0.7252 (3)	0.0823 (13)
H22A	0.5781	0.9410	0.7781	0.099*
C23	0.56259 (11)	0.8848 (5)	0.5979 (2)	0.0700 (11)
H23A	0.5479	0.8672	0.5450	0.084*
N4	0.45438 (12)	0.1212 (5)	0.0878 (3)	0.0839 (11)
O3	0.41881 (10)	0.1263 (5)	0.0716 (2)	0.1251 (13)
O4	0.47371 (9)	0.1062 (5)	0.1602 (2)	0.1148 (13)
O5	0.47201 (9)	0.1337 (4)	0.03508 (19)	0.1087 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0756 (9)	0.1377 (13)	0.1570 (13)	−0.0353 (8)	0.0145 (8)	−0.0120 (10)
N1	0.0538 (19)	0.066 (2)	0.058 (2)	0.0018 (16)	0.0214 (15)	−0.0005 (17)
O1	0.0680 (19)	0.100 (2)	0.0800 (19)	−0.0165 (17)	0.0211 (14)	−0.0192 (18)
F1	0.1021 (19)	0.133 (2)	0.142 (2)	−0.0203 (17)	0.0900 (18)	−0.0211 (19)
C1	0.071 (3)	0.106 (4)	0.068 (3)	−0.006 (3)	0.028 (2)	−0.001 (3)
O2	0.0637 (18)	0.101 (2)	0.088 (2)	−0.0172 (16)	0.0399 (15)	−0.0352 (18)
F2	0.0991 (19)	0.124 (2)	0.1046 (19)	0.0447 (16)	0.0508 (15)	0.0433 (17)
N2	0.070 (2)	0.114 (3)	0.060 (2)	0.001 (2)	0.0299 (18)	−0.004 (2)
C2	0.063 (3)	0.106 (4)	0.089 (3)	−0.011 (3)	0.034 (2)	0.014 (3)
N3	0.059 (2)	0.080 (3)	0.091 (3)	−0.0028 (19)	0.040 (2)	−0.006 (2)
C3	0.064 (3)	0.086 (3)	0.091 (3)	−0.014 (2)	0.018 (3)	0.007 (3)
C4	0.079 (3)	0.073 (3)	0.077 (3)	−0.010 (3)	0.013 (2)	−0.003 (2)
C5	0.067 (3)	0.072 (3)	0.074 (3)	−0.005 (2)	0.027 (2)	0.000 (2)
C6	0.054 (2)	0.074 (3)	0.070 (3)	−0.009 (2)	0.013 (2)	0.004 (2)
C7	0.077 (3)	0.105 (4)	0.096 (3)	−0.015 (3)	0.015 (3)	−0.019 (3)
C8	0.084 (4)	0.101 (4)	0.113 (4)	−0.013 (3)	0.001 (3)	−0.024 (3)
C9	0.069 (3)	0.106 (4)	0.099 (3)	−0.020 (3)	0.008 (2)	−0.005 (3)
C10	0.080 (3)	0.113 (4)	0.115 (4)	−0.015 (3)	0.014 (3)	−0.019 (3)
C11	0.077 (3)	0.119 (4)	0.117 (4)	−0.014 (3)	0.029 (3)	−0.023 (3)
C12	0.063 (3)	0.139 (4)	0.109 (4)	−0.017 (3)	0.029 (3)	−0.050 (4)
C13	0.046 (2)	0.063 (3)	0.059 (2)	0.001 (2)	0.0191 (18)	0.002 (2)
C14	0.052 (2)	0.065 (3)	0.057 (2)	0.001 (2)	0.0227 (18)	0.002 (2)
C15	0.079 (3)	0.084 (3)	0.085 (3)	0.012 (2)	0.038 (2)	0.012 (3)
C16	0.103 (4)	0.093 (4)	0.083 (3)	−0.011 (3)	0.052 (3)	0.010 (3)
C17	0.066 (3)	0.084 (4)	0.091 (3)	−0.019 (3)	0.046 (3)	−0.020 (3)
C18	0.053 (2)	0.085 (3)	0.091 (3)	−0.001 (2)	0.031 (2)	−0.011 (3)
C19	0.061 (2)	0.075 (3)	0.059 (2)	0.001 (2)	0.023 (2)	0.006 (2)
C20	0.049 (2)	0.073 (3)	0.058 (2)	0.004 (2)	0.0211 (18)	0.001 (2)
C21	0.067 (3)	0.132 (4)	0.105 (3)	−0.030 (3)	0.040 (2)	−0.040 (3)
C22	0.083 (3)	0.109 (4)	0.064 (3)	−0.008 (3)	0.036 (3)	−0.011 (3)
C23	0.051 (2)	0.094 (3)	0.070 (3)	−0.001 (2)	0.025 (2)	−0.011 (3)
N4	0.071 (3)	0.099 (3)	0.091 (3)	−0.004 (2)	0.037 (2)	−0.015 (3)
O3	0.064 (2)	0.180 (4)	0.134 (3)	−0.024 (2)	0.0314 (19)	−0.032 (3)
O4	0.076 (2)	0.192 (4)	0.089 (2)	0.014 (2)	0.0453 (19)	0.026 (3)
O5	0.092 (2)	0.156 (3)	0.094 (2)	0.004 (2)	0.0514 (19)	0.001 (2)

Geometric parameters (Å, º) top

Cl—C3	1.733 (4)	C9—H9A	0.9700
N1—C23	1.311 (4)	C9—H9B	0.9700
N1—N2	1.375 (4)	C10—C11	1.465 (6)
N1—C20	1.443 (4)	C10—H10A	0.9700
O1—C6	1.363 (4)	C10—H10B	0.9700
O1—C7	1.420 (5)	C11—C12	1.503 (5)
F1—C17	1.353 (4)	C11—H11A	0.9700
C1—C2	1.379 (5)	C11—H11B	0.9700
C1—C6	1.385 (5)	C12—H12A	0.9700
C1—H1A	0.9300	C12—H12B	0.9700
O2—C13	1.361 (4)	C13—C20	1.310 (5)
O2—C12	1.418 (5)	C13—C14	1.488 (5)
F2—C19	1.349 (4)	C14—C19	1.358 (5)
N2—C22	1.290 (4)	C14—C15	1.374 (5)
C2—C3	1.357 (5)	C15—C16	1.400 (5)
C2—H2B	0.9300	C15—H15A	0.9300
N3—C23	1.321 (4)	C16—C17	1.361 (6)
N3—C22	1.335 (5)	C16—H16A	0.9300
N3—H3A	0.8600	C17—C18	1.347 (5)
C3—C4	1.385 (6)	C18—C19	1.381 (5)
C4—C5	1.381 (5)	C18—H18A	0.9300
C4—H4A	0.9300	C20—C21	1.497 (5)
C5—C6	1.378 (5)	C21—H21A	0.9600
C5—H5A	0.9300	C21—H21B	0.9600
C7—C8	1.492 (5)	C21—H21C	0.9600
C7—H7A	0.9700	C22—H22A	0.9300
C7—H7B	0.9700	C23—H23A	0.9300
C8—C9	1.472 (6)	N4—O3	1.222 (4)
C8—H8A	0.9700	N4—O4	1.253 (4)
C8—H8B	0.9700	N4—O5	1.229 (4)
C9—C10	1.548 (6)

C23—N1—N2	110.1 (3)	C10—C11—C12	115.4 (5)
C23—N1—C20	130.9 (3)	C10—C11—H11A	108.4
N2—N1—C20	119.0 (3)	C12—C11—H11A	108.4
C6—O1—C7	118.1 (3)	C10—C11—H11B	108.4
C2—C1—C6	119.0 (4)	C12—C11—H11B	108.4
C2—C1—H1A	120.5	H11A—C11—H11B	107.5
C6—C1—H1A	120.5	O2—C12—C11	110.0 (4)
C13—O2—C12	119.3 (3)	O2—C12—H12A	109.7
C22—N2—N1	103.4 (3)	C11—C12—H12A	109.7
C3—C2—C1	121.2 (4)	O2—C12—H12B	109.7
C3—C2—H2B	119.4	C11—C12—H12B	109.7
C1—C2—H2B	119.4	H12A—C12—H12B	108.2
C23—N3—C22	106.3 (3)	C20—C13—O2	120.0 (3)
C23—N3—H3A	126.9	C20—C13—C14	121.7 (3)
C22—N3—H3A	126.9	O2—C13—C14	118.3 (3)
C2—C3—C4	120.3 (4)	C19—C14—C15	117.0 (3)
C2—C3—Cl	120.5 (4)	C19—C14—C13	121.7 (3)
C4—C3—Cl	119.2 (4)	C15—C14—C13	121.3 (4)
C3—C4—C5	119.1 (4)	C14—C15—C16	120.7 (4)
C3—C4—H4A	120.4	C14—C15—H15A	119.6
C5—C4—H4A	120.4	C16—C15—H15A	119.6
C6—C5—C4	120.5 (4)	C17—C16—C15	118.0 (4)
C6—C5—H5A	119.8	C17—C16—H16A	121.0
C4—C5—H5A	119.8	C15—C16—H16A	121.0
O1—C6—C5	116.0 (3)	C18—C17—F1	118.1 (5)
O1—C6—C1	124.0 (4)	C18—C17—C16	123.7 (4)
C5—C6—C1	120.0 (4)	F1—C17—C16	118.2 (5)
O1—C7—C8	109.3 (4)	C17—C18—C19	115.8 (4)
O1—C7—H7A	109.8	C17—C18—H18A	122.1
C8—C7—H7A	109.8	C19—C18—H18A	122.1
O1—C7—H7B	109.8	F2—C19—C14	118.3 (3)
C8—C7—H7B	109.8	F2—C19—C18	117.1 (4)
H7A—C7—H7B	108.3	C14—C19—C18	124.6 (4)
C9—C8—C7	115.4 (4)	C13—C20—N1	119.9 (3)
C9—C8—H8A	108.4	C13—C20—C21	126.3 (3)
C7—C8—H8A	108.4	N1—C20—C21	113.8 (3)
C9—C8—H8B	108.4	C20—C21—H21A	109.5
C7—C8—H8B	108.4	C20—C21—H21B	109.5
H8A—C8—H8B	107.5	H21A—C21—H21B	109.5
C8—C9—C10	112.0 (4)	C20—C21—H21C	109.5
C8—C9—H9A	109.2	H21A—C21—H21C	109.5
C10—C9—H9A	109.2	H21B—C21—H21C	109.5
C8—C9—H9B	109.2	N2—C22—N3	112.6 (4)
C10—C9—H9B	109.2	N2—C22—H22A	123.7
H9A—C9—H9B	107.9	N3—C22—H22A	123.7
C11—C10—C9	113.6 (4)	N1—C23—N3	107.6 (3)
C11—C10—H10A	108.8	N1—C23—H23A	126.2
C9—C10—H10A	108.8	N3—C23—H23A	126.2
C11—C10—H10B	108.8	O3—N4—O4	119.6 (4)
C9—C10—H10B	108.8	O3—N4—O5	121.8 (4)
H10A—C10—H10B	107.7	O4—N4—O5	118.6 (4)

C23—N1—N2—C22	0.9 (5)	C19—C14—C15—C16	0.2 (6)
C20—N1—N2—C22	−177.0 (3)	C13—C14—C15—C16	178.7 (4)
C6—C1—C2—C3	−0.6 (7)	C14—C15—C16—C17	−1.6 (7)
C1—C2—C3—C4	0.7 (7)	C15—C16—C17—C18	2.0 (7)
C1—C2—C3—Cl	179.8 (3)	C15—C16—C17—F1	−178.7 (4)
C2—C3—C4—C5	−0.6 (7)	F1—C17—C18—C19	179.8 (3)
Cl—C3—C4—C5	−179.8 (3)	C16—C17—C18—C19	−0.9 (6)
C3—C4—C5—C6	0.5 (6)	C15—C14—C19—F2	−178.2 (3)
C7—O1—C6—C5	177.0 (4)	C13—C14—C19—F2	3.2 (5)
C7—O1—C6—C1	−2.8 (6)	C15—C14—C19—C18	1.1 (6)
C4—C5—C6—O1	179.8 (3)	C13—C14—C19—C18	−177.5 (4)
C4—C5—C6—C1	−0.4 (6)	C17—C18—C19—F2	178.6 (3)
C2—C1—C6—O1	−179.7 (4)	C17—C18—C19—C14	−0.7 (6)
C2—C1—C6—C5	0.4 (6)	O2—C13—C20—N1	−0.3 (5)
C6—O1—C7—C8	−173.4 (4)	C14—C13—C20—N1	−179.1 (3)
O1—C7—C8—C9	−62.7 (6)	O2—C13—C20—C21	179.5 (4)
C7—C8—C9—C10	−176.3 (4)	C14—C13—C20—C21	0.7 (6)
C8—C9—C10—C11	178.0 (4)	C23—N1—C20—C13	−27.6 (6)
C9—C10—C11—C12	175.4 (4)	N2—N1—C20—C13	149.8 (3)
C13—O2—C12—C11	178.8 (4)	C23—N1—C20—C21	152.6 (4)
C10—C11—C12—O2	64.8 (6)	N2—N1—C20—C21	−30.0 (5)
C12—O2—C13—C20	−178.8 (4)	N1—N2—C22—N3	−0.3 (5)
C12—O2—C13—C14	0.1 (5)	C23—N3—C22—N2	−0.4 (5)
C20—C13—C14—C19	89.2 (5)	N2—N1—C23—N3	−1.2 (5)
O2—C13—C14—C19	−89.7 (4)	C20—N1—C23—N3	176.4 (3)
C20—C13—C14—C15	−89.3 (5)	C22—N3—C23—N1	1.0 (5)
O2—C13—C14—C15	91.8 (5)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅ClF₂N₃O₂⁺·NO₃⁻
M_r	510.92
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	35.538 (7), 8.5550 (17), 17.072 (3)
β (°)	105.21 (3)
V (Å³)	5008.6 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.940, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	9194, 4628, 1954
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.176, 1.00
No. of reflections	4628
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

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···O4ⁱ	0.86	1.8	2.661 (5)	175
C22—H22A···O4ⁱⁱ	0.93	2.38	3.077 (6)	131

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

Acknowledgements

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).

References

Enraf–Nonius (1994). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fromtling, R. & Castaner, J. (1996). Drugs Future, 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
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
Zirngibl, L. & Thiele, K. (1985). US Patent Appl. US4554356. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2617

https://doi.org/10.1107/S1600536811034933

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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