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
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
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
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell 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
https://doi.org/10.1107/S1600536811038761/pv2445sup1.cif
contains datablocks global, I. DOI: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
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).
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 Uiso(H) = 1.2 (or 1.5 for methyl groups) times Ueq(C).
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
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 the anions and cations are connected via N—H···O, C—H···O and C—H···F hydrogen bonding (Table 1 and Fig. 2).
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).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
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).C21H21ClF2N3O2+·NO3− | F(000) = 1000 |
Mr = 482.87 | Dx = 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 |
Enraf–Nonius CAD-4 diffractometer | 1952 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.092 |
Graphite monochromator | θmax = 25.4°, θmin = 1.3° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→38 |
Tmin = 0.936, Tmax = 0.978 | l = −11→10 |
4521 measured reflections | 3 standard reflections every 200 reflections |
4216 independent reflections | intensity decay: 1% |
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(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3 |
4216 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C21H21ClF2N3O2+·NO3− | V = 2293.6 (8) Å3 |
Mr = 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)° |
Enraf–Nonius CAD-4 diffractometer | 1952 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.092 |
Tmin = 0.936, Tmax = 0.978 | 3 standard reflections every 200 reflections |
4521 measured reflections | intensity decay: 1% |
4216 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.20 e Å−3 |
4216 reflections | Δρmin = −0.24 e Å−3 |
298 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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) |
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− |
Mr | 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) |
Tmin, Tmax | 0.936, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4521, 4216, 1952 |
Rint | 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 |
Δρmax, Δρmin (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).
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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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).