organic compounds
1-{(Z)-1-(2,4-Dichlorophenyl)-1-[2-(4-methylphenoxy)ethoxy]prop-1-en-2-yl}-1H-imidazol-3-ium nitrate
aJiangsu Engineering Technology Research Center of Polypeptide Pharmaceutical, College of Biotechnology 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: chemywg@126.com
In the title salt, C21H21Cl2N2O2+·NO3−, the imidazole ring makes dihedral angles of 43.39 (14) and 10.9 (2)° with the 4-methylphenyl and 2,4-dichlorophenyl rings, respectively. The molecule adopts a Z conformation about the C=C double bond, which links the imidazole ring to the 4-methylphenoxy unit via an ethoxy chain. In the crystal, cations and anions are linked into chains by N—H⋯O and C—H⋯O hydrogen bonds.
Related literature
For background to azole derivatives and synthetic details, see: Jeu et al. (2003); Fromtling & Castaner (1996); 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/S1600536812046181/pv2548sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812046181/pv2548Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812046181/pv2548Isup3.cml
1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)-1-propanone (16.6 g, 0.06 mol), 30% aqueous sodium hydroxide (50 ml), toluene (100 ml) and tetrabutylammonium hydroxide (0.26g, 0.001mol) were mixed and heated to 343.15 K under vigorous stirring. 1-(2-Bromoethoxy)-4-methyl-benzene (13.3 g, 0.06 mol), dissolved in toluene (70 ml), wais instilled into the stirred and warmed solution in the course of 10 h. The mixture was stirred at room temperature, and monitored by TLC until the reaction was complete. 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 is diluted with 100 ml ethanol and then adjusted to a pH-value of 2 by means of 65% aqueous nitric acid. The derived nitric acid solution was cooled in the refrigerator. The impure precipitated product herein was subsequently crystallized from isopropanol. The purified product was 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. Details on the synthesis can be found in the literature (Ludwig & Kurt, 1985).
H atoms were positioned geometrically with C—H = 0.93, 0.96 and 0.97 Å for aryl, methyl and methylene H atoms, respectively, and with N—H = 0.86 Å for imidazole H atom, and constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq methyl C or 1.2Ueq non-methyl C/N).
Azole derivatives such as Voriconazole and Ketoconazole are safe and effective antifungal agents (Jeu et al., 2003; Fromtling & Castaner,1996). As part of our studies on the synthesis of new azole derivatives, the
of the title compound was determined.In the molecular structure of the title compound (Fig. 1) the double bond is Z configurated. In the
the anions and cations are connected via N—H···O and C—H···O hydrogen bonding (Table 1 and Fig. 2). The bond lengths and bpnd angles in the title compound agree with the corresponding bond lengths and angles reported for a closely related compound (Kurt et al., 1987).For background to azole derivatives and synthetic details, see: Jeu et al. (2003); Fromtling & Castaner (1996); 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).C21H21Cl2N2O2+·NO3− | Z = 2 |
Mr = 466.31 | F(000) = 484 |
Triclinic, P1 | Dx = 1.429 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5300 (19) Å | Cell parameters from 25 reflections |
b = 9.924 (2) Å | θ = 10–13° |
c = 12.449 (3) Å | µ = 0.34 mm−1 |
α = 69.05 (3)° | T = 293 K |
β = 80.59 (3)° | Plate, colorless |
γ = 88.75 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 1083.9 (4) Å3 |
Enraf–Nonius CAD-4 diffractometer | 2974 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.4°, θmin = 1.8° |
ω/2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→11 |
Tmin = 0.905, Tmax = 0.967 | l = −14→15 |
4247 measured reflections | 3 standard reflections every 200 reflections |
3988 independent reflections | intensity decay: 1% |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.230P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3988 reflections | Δρmax = 0.33 e Å−3 |
281 parameters | Δρmin = −0.25 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: 0.034 (5) |
C21H21Cl2N2O2+·NO3− | γ = 88.75 (3)° |
Mr = 466.31 | V = 1083.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.5300 (19) Å | Mo Kα radiation |
b = 9.924 (2) Å | µ = 0.34 mm−1 |
c = 12.449 (3) Å | T = 293 K |
α = 69.05 (3)° | 0.30 × 0.20 × 0.10 mm |
β = 80.59 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2974 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.020 |
Tmin = 0.905, Tmax = 0.967 | 3 standard reflections every 200 reflections |
4247 measured reflections | intensity decay: 1% |
3988 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.33 e Å−3 |
3988 reflections | Δρmin = −0.25 e Å−3 |
281 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
Cl1 | 0.27013 (8) | 0.96396 (8) | 0.60041 (6) | 0.0542 (3) | |
N1 | 0.1889 (2) | 1.1363 (2) | 0.18787 (18) | 0.0431 (5) | |
O1 | −0.0643 (2) | 0.8053 (2) | 0.31896 (19) | 0.0589 (6) | |
C1 | −0.1250 (3) | 0.5853 (3) | 0.2860 (3) | 0.0576 (8) | |
H1A | −0.0639 | 0.5293 | 0.3338 | 0.069* | |
Cl2 | 0.67621 (8) | 0.57854 (8) | 0.62094 (7) | 0.0624 (3) | |
O2 | 0.11483 (19) | 0.95339 (19) | 0.40364 (16) | 0.0462 (5) | |
N2 | 0.0151 (3) | 1.1943 (3) | 0.0941 (2) | 0.0588 (7) | |
H2A | −0.0525 | 1.1890 | 0.0576 | 0.071* | |
C2 | −0.2091 (4) | 0.5242 (4) | 0.2333 (3) | 0.0633 (9) | |
H2B | −0.2039 | 0.4258 | 0.2471 | 0.076* | |
C3 | −0.3003 (3) | 0.6038 (4) | 0.1610 (3) | 0.0587 (8) | |
C4 | −0.3025 (3) | 0.7508 (4) | 0.1395 (3) | 0.0587 (8) | |
H4A | −0.3605 | 0.8075 | 0.0889 | 0.070* | |
C5 | −0.2213 (3) | 0.8148 (3) | 0.1909 (2) | 0.0548 (7) | |
H5A | −0.2250 | 0.9136 | 0.1752 | 0.066* | |
C6 | −0.1338 (3) | 0.7322 (3) | 0.2662 (2) | 0.0487 (7) | |
C7 | −0.3924 (4) | 0.5339 (5) | 0.1058 (3) | 0.0797 (11) | |
H7A | −0.3769 | 0.4322 | 0.1308 | 0.120* | |
H7B | −0.3679 | 0.5761 | 0.0224 | 0.120* | |
H7C | −0.4907 | 0.5490 | 0.1291 | 0.120* | |
C8 | 0.0226 (3) | 0.7263 (3) | 0.4017 (3) | 0.0547 (7) | |
H8A | 0.1129 | 0.7076 | 0.3618 | 0.066* | |
H8B | −0.0244 | 0.6345 | 0.4519 | 0.066* | |
C9 | 0.0465 (3) | 0.8152 (3) | 0.4726 (2) | 0.0506 (7) | |
H9A | −0.0444 | 0.8294 | 0.5142 | 0.061* | |
H9B | 0.1047 | 0.7625 | 0.5300 | 0.061* | |
C10 | 0.2547 (3) | 0.9564 (3) | 0.3550 (2) | 0.0398 (6) | |
C11 | 0.2977 (3) | 1.0517 (3) | 0.2472 (2) | 0.0432 (6) | |
C12 | 0.4455 (3) | 1.0837 (3) | 0.1785 (3) | 0.0577 (8) | |
H12A | 0.5109 | 1.0240 | 0.2241 | 0.087* | |
H12B | 0.4715 | 1.1835 | 0.1593 | 0.087* | |
H12C | 0.4487 | 1.0641 | 0.1080 | 0.087* | |
C13 | 0.1000 (3) | 1.0907 (3) | 0.1358 (3) | 0.0541 (7) | |
H13A | 0.0983 | 0.9999 | 0.1300 | 0.065* | |
C14 | 0.0496 (4) | 1.3107 (4) | 0.1171 (3) | 0.0654 (9) | |
H14A | 0.0060 | 1.3989 | 0.0956 | 0.078* | |
C15 | 0.1586 (4) | 1.2761 (3) | 0.1766 (3) | 0.0625 (9) | |
H15A | 0.2046 | 1.3352 | 0.2047 | 0.075* | |
C16 | 0.3537 (3) | 0.8592 (3) | 0.4249 (2) | 0.0384 (6) | |
C17 | 0.3715 (3) | 0.8572 (3) | 0.5351 (2) | 0.0399 (6) | |
C18 | 0.4695 (3) | 0.7714 (3) | 0.5946 (2) | 0.0437 (6) | |
H18A | 0.4807 | 0.7714 | 0.6675 | 0.052* | |
C19 | 0.5516 (3) | 0.6850 (3) | 0.5453 (2) | 0.0434 (6) | |
C20 | 0.5350 (3) | 0.6810 (3) | 0.4384 (2) | 0.0443 (6) | |
H20A | 0.5890 | 0.6210 | 0.4066 | 0.053* | |
C21 | 0.4362 (3) | 0.7683 (3) | 0.3798 (2) | 0.0420 (6) | |
H21A | 0.4244 | 0.7662 | 0.3077 | 0.050* | |
O3 | 0.2956 (5) | 1.7477 (5) | 0.1574 (4) | 0.1483 (17) | |
O4 | 0.1936 (4) | 1.6269 (3) | 0.0810 (4) | 0.1205 (12) | |
O5 | 0.1832 (4) | 1.8521 (3) | 0.0225 (3) | 0.1028 (10) | |
N3 | 0.2273 (3) | 1.7407 (3) | 0.0876 (3) | 0.0646 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0563 (5) | 0.0623 (5) | 0.0526 (4) | 0.0116 (3) | −0.0167 (3) | −0.0281 (3) |
N1 | 0.0496 (13) | 0.0425 (12) | 0.0375 (11) | 0.0039 (10) | −0.0188 (10) | −0.0097 (9) |
O1 | 0.0617 (13) | 0.0463 (11) | 0.0704 (14) | 0.0036 (9) | −0.0316 (11) | −0.0140 (10) |
C1 | 0.0519 (17) | 0.0528 (17) | 0.0664 (19) | 0.0028 (14) | −0.0114 (15) | −0.0185 (15) |
Cl2 | 0.0602 (5) | 0.0627 (5) | 0.0686 (5) | 0.0179 (4) | −0.0361 (4) | −0.0185 (4) |
O2 | 0.0403 (10) | 0.0456 (10) | 0.0481 (11) | 0.0047 (8) | −0.0132 (8) | −0.0091 (8) |
N2 | 0.0570 (15) | 0.0665 (17) | 0.0516 (14) | 0.0088 (13) | −0.0288 (12) | −0.0115 (12) |
C2 | 0.062 (2) | 0.0557 (18) | 0.072 (2) | −0.0064 (15) | −0.0016 (17) | −0.0259 (16) |
C3 | 0.0560 (18) | 0.076 (2) | 0.0436 (16) | −0.0140 (16) | 0.0016 (14) | −0.0245 (15) |
C4 | 0.0570 (18) | 0.073 (2) | 0.0422 (16) | −0.0013 (15) | −0.0117 (14) | −0.0145 (15) |
C5 | 0.0602 (18) | 0.0526 (17) | 0.0463 (16) | −0.0009 (14) | −0.0117 (14) | −0.0100 (13) |
C6 | 0.0444 (15) | 0.0483 (16) | 0.0500 (16) | −0.0040 (12) | −0.0079 (13) | −0.0132 (13) |
C7 | 0.086 (3) | 0.098 (3) | 0.059 (2) | −0.025 (2) | −0.0081 (19) | −0.033 (2) |
C8 | 0.0440 (16) | 0.0483 (16) | 0.0664 (19) | 0.0031 (13) | −0.0213 (14) | −0.0090 (14) |
C9 | 0.0403 (14) | 0.0547 (16) | 0.0480 (16) | 0.0000 (12) | −0.0117 (12) | −0.0059 (13) |
C10 | 0.0415 (14) | 0.0390 (13) | 0.0423 (14) | 0.0035 (11) | −0.0152 (11) | −0.0154 (11) |
C11 | 0.0445 (15) | 0.0440 (14) | 0.0428 (14) | 0.0037 (11) | −0.0184 (12) | −0.0129 (12) |
C12 | 0.0531 (17) | 0.0618 (18) | 0.0483 (16) | −0.0021 (14) | −0.0115 (14) | −0.0061 (14) |
C13 | 0.0642 (19) | 0.0470 (16) | 0.0542 (17) | 0.0030 (14) | −0.0301 (15) | −0.0131 (13) |
C14 | 0.081 (2) | 0.0560 (19) | 0.0578 (19) | 0.0255 (17) | −0.0242 (17) | −0.0149 (15) |
C15 | 0.084 (2) | 0.0486 (17) | 0.064 (2) | 0.0142 (16) | −0.0320 (18) | −0.0232 (15) |
C16 | 0.0379 (13) | 0.0397 (13) | 0.0357 (13) | −0.0011 (11) | −0.0113 (10) | −0.0089 (11) |
C17 | 0.0385 (13) | 0.0411 (13) | 0.0395 (14) | −0.0018 (11) | −0.0076 (11) | −0.0133 (11) |
C18 | 0.0478 (15) | 0.0456 (14) | 0.0377 (14) | −0.0022 (12) | −0.0159 (12) | −0.0108 (12) |
C19 | 0.0393 (14) | 0.0410 (13) | 0.0462 (15) | −0.0006 (11) | −0.0165 (12) | −0.0070 (11) |
C20 | 0.0430 (14) | 0.0423 (14) | 0.0457 (15) | 0.0013 (11) | −0.0090 (12) | −0.0128 (12) |
C21 | 0.0481 (15) | 0.0426 (14) | 0.0360 (13) | 0.0014 (12) | −0.0134 (11) | −0.0120 (11) |
O3 | 0.183 (4) | 0.180 (4) | 0.144 (3) | 0.071 (3) | −0.129 (3) | −0.092 (3) |
O4 | 0.135 (3) | 0.0709 (19) | 0.176 (4) | 0.0274 (18) | −0.062 (3) | −0.055 (2) |
O5 | 0.128 (2) | 0.0620 (15) | 0.127 (2) | 0.0147 (16) | −0.085 (2) | −0.0174 (16) |
N3 | 0.0731 (18) | 0.0680 (18) | 0.0660 (17) | 0.0236 (14) | −0.0354 (15) | −0.0309 (15) |
Cl1—C17 | 1.741 (3) | C8—H8A | 0.9700 |
N1—C13 | 1.322 (3) | C8—H8B | 0.9700 |
N1—C15 | 1.373 (4) | C9—H9A | 0.9700 |
N1—C11 | 1.447 (3) | C9—H9B | 0.9700 |
O1—C6 | 1.379 (3) | C10—C11 | 1.339 (4) |
O1—C8 | 1.427 (3) | C10—C16 | 1.486 (3) |
C1—C2 | 1.385 (4) | C11—C12 | 1.500 (4) |
C1—C6 | 1.391 (4) | C12—H12A | 0.9600 |
C1—H1A | 0.9300 | C12—H12B | 0.9600 |
Cl2—C19 | 1.736 (3) | C12—H12C | 0.9600 |
O2—C10 | 1.367 (3) | C13—H13A | 0.9300 |
O2—C9 | 1.434 (3) | C14—C15 | 1.342 (5) |
N2—C13 | 1.304 (4) | C14—H14A | 0.9300 |
N2—C14 | 1.344 (4) | C15—H15A | 0.9300 |
N2—H2A | 0.8600 | C16—C21 | 1.391 (4) |
C2—C3 | 1.381 (5) | C16—C17 | 1.403 (4) |
C2—H2B | 0.9300 | C17—C18 | 1.374 (4) |
C3—C4 | 1.386 (5) | C18—C19 | 1.383 (4) |
C3—C7 | 1.513 (5) | C18—H18A | 0.9300 |
C4—C5 | 1.374 (4) | C19—C20 | 1.380 (4) |
C4—H4A | 0.9300 | C20—C21 | 1.381 (4) |
C5—C6 | 1.386 (4) | C20—H20A | 0.9300 |
C5—H5A | 0.9300 | C21—H21A | 0.9300 |
C7—H7A | 0.9600 | O3—N3 | 1.189 (4) |
C7—H7B | 0.9600 | O4—N3 | 1.215 (4) |
C7—H7C | 0.9600 | O5—N3 | 1.227 (4) |
C8—C9 | 1.496 (4) | ||
C13—N1—C15 | 108.1 (2) | H9A—C9—H9B | 107.8 |
C13—N1—C11 | 125.4 (2) | C11—C10—O2 | 118.1 (2) |
C15—N1—C11 | 126.5 (2) | C11—C10—C16 | 122.7 (2) |
C6—O1—C8 | 118.6 (2) | O2—C10—C16 | 119.1 (2) |
C2—C1—C6 | 118.8 (3) | C10—C11—N1 | 116.8 (2) |
C2—C1—H1A | 120.6 | C10—C11—C12 | 128.5 (2) |
C6—C1—H1A | 120.6 | N1—C11—C12 | 114.8 (2) |
C10—O2—C9 | 117.7 (2) | C11—C12—H12A | 109.5 |
C13—N2—C14 | 109.5 (3) | C11—C12—H12B | 109.5 |
C13—N2—H2A | 125.3 | H12A—C12—H12B | 109.5 |
C14—N2—H2A | 125.3 | C11—C12—H12C | 109.5 |
C3—C2—C1 | 122.4 (3) | H12A—C12—H12C | 109.5 |
C3—C2—H2B | 118.8 | H12B—C12—H12C | 109.5 |
C1—C2—H2B | 118.8 | N2—C13—N1 | 108.5 (3) |
C2—C3—C4 | 117.4 (3) | N2—C13—H13A | 125.7 |
C2—C3—C7 | 121.3 (3) | N1—C13—H13A | 125.7 |
C4—C3—C7 | 121.3 (3) | C15—C14—N2 | 107.5 (3) |
C5—C4—C3 | 121.7 (3) | C15—C14—H14A | 126.3 |
C5—C4—H4A | 119.2 | N2—C14—H14A | 126.3 |
C3—C4—H4A | 119.2 | C14—C15—N1 | 106.4 (3) |
C4—C5—C6 | 120.0 (3) | C14—C15—H15A | 126.8 |
C4—C5—H5A | 120.0 | N1—C15—H15A | 126.8 |
C6—C5—H5A | 120.0 | C21—C16—C17 | 117.5 (2) |
O1—C6—C5 | 115.3 (2) | C21—C16—C10 | 119.8 (2) |
O1—C6—C1 | 125.1 (3) | C17—C16—C10 | 122.7 (2) |
C5—C6—C1 | 119.6 (3) | C18—C17—C16 | 121.1 (2) |
C3—C7—H7A | 109.5 | C18—C17—Cl1 | 118.0 (2) |
C3—C7—H7B | 109.5 | C16—C17—Cl1 | 120.9 (2) |
H7A—C7—H7B | 109.5 | C17—C18—C19 | 119.5 (2) |
C3—C7—H7C | 109.5 | C17—C18—H18A | 120.3 |
H7A—C7—H7C | 109.5 | C19—C18—H18A | 120.3 |
H7B—C7—H7C | 109.5 | C20—C19—C18 | 121.3 (2) |
O1—C8—C9 | 107.8 (2) | C20—C19—Cl2 | 119.8 (2) |
O1—C8—H8A | 110.1 | C18—C19—Cl2 | 118.9 (2) |
C9—C8—H8A | 110.1 | C19—C20—C21 | 118.3 (2) |
O1—C8—H8B | 110.1 | C19—C20—H20A | 120.8 |
C9—C8—H8B | 110.1 | C21—C20—H20A | 120.8 |
H8A—C8—H8B | 108.5 | C20—C21—C16 | 122.2 (2) |
O2—C9—C8 | 113.2 (2) | C20—C21—H21A | 118.9 |
O2—C9—H9A | 108.9 | C16—C21—H21A | 118.9 |
C8—C9—H9A | 108.9 | O3—N3—O4 | 122.8 (4) |
O2—C9—H9B | 108.9 | O3—N3—O5 | 119.1 (3) |
C8—C9—H9B | 108.9 | O4—N3—O5 | 118.0 (3) |
C6—C1—C2—C3 | 0.6 (5) | C14—N2—C13—N1 | 1.0 (4) |
C1—C2—C3—C4 | 1.8 (5) | C15—N1—C13—N2 | −0.8 (4) |
C1—C2—C3—C7 | −179.2 (3) | C11—N1—C13—N2 | 178.6 (3) |
C2—C3—C4—C5 | −2.2 (5) | C13—N2—C14—C15 | −0.9 (4) |
C7—C3—C4—C5 | 178.8 (3) | N2—C14—C15—N1 | 0.4 (4) |
C3—C4—C5—C6 | 0.2 (5) | C13—N1—C15—C14 | 0.2 (4) |
C8—O1—C6—C5 | 177.2 (3) | C11—N1—C15—C14 | −179.2 (3) |
C8—O1—C6—C1 | −0.8 (4) | C11—C10—C16—C21 | −56.0 (4) |
C4—C5—C6—O1 | −175.8 (3) | O2—C10—C16—C21 | 126.9 (3) |
C4—C5—C6—C1 | 2.3 (4) | C11—C10—C16—C17 | 122.3 (3) |
C2—C1—C6—O1 | 175.3 (3) | O2—C10—C16—C17 | −54.9 (3) |
C2—C1—C6—C5 | −2.7 (4) | C21—C16—C17—C18 | 1.8 (4) |
C6—O1—C8—C9 | −162.1 (2) | C10—C16—C17—C18 | −176.5 (2) |
C10—O2—C9—C8 | −70.2 (3) | C21—C16—C17—Cl1 | −178.48 (19) |
O1—C8—C9—O2 | −59.3 (3) | C10—C16—C17—Cl1 | 3.2 (4) |
C9—O2—C10—C11 | 141.4 (2) | C16—C17—C18—C19 | −0.3 (4) |
C9—O2—C10—C16 | −41.2 (3) | Cl1—C17—C18—C19 | 179.9 (2) |
O2—C10—C11—N1 | −4.6 (4) | C17—C18—C19—C20 | −1.3 (4) |
C16—C10—C11—N1 | 178.2 (2) | C17—C18—C19—Cl2 | 179.39 (19) |
O2—C10—C11—C12 | 175.2 (3) | C18—C19—C20—C21 | 1.5 (4) |
C16—C10—C11—C12 | −2.0 (4) | Cl2—C19—C20—C21 | −179.2 (2) |
C13—N1—C11—C10 | −78.8 (4) | C19—C20—C21—C16 | 0.0 (4) |
C15—N1—C11—C10 | 100.4 (3) | C17—C16—C21—C20 | −1.6 (4) |
C13—N1—C11—C12 | 101.3 (3) | C10—C16—C21—C20 | 176.7 (2) |
C15—N1—C11—C12 | −79.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O4 | 0.86 | 2.55 | 3.218 (5) | 135 |
N2—H2A···O5i | 0.86 | 1.85 | 2.703 (5) | 170 |
C13—H13A···O5ii | 0.93 | 2.37 | 3.188 (5) | 147 |
C21—H21A···O3ii | 0.93 | 2.46 | 3.337 (5) | 157 |
Symmetry codes: (i) −x, −y+3, −z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H21Cl2N2O2+·NO3− |
Mr | 466.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.5300 (19), 9.924 (2), 12.449 (3) |
α, β, γ (°) | 69.05 (3), 80.59 (3), 88.75 (3) |
V (Å3) | 1083.9 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.905, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4247, 3988, 2974 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.603 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.158, 1.01 |
No. of reflections | 3988 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.25 |
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 |
N2—H2A···O4 | 0.86 | 2.55 | 3.218 (5) | 135 |
N2—H2A···O5i | 0.86 | 1.85 | 2.703 (5) | 170 |
C13—H13A···O5ii | 0.93 | 2.37 | 3.188 (5) | 147 |
C21—H21A···O3ii | 0.93 | 2.46 | 3.337 (5) | 157 |
Symmetry codes: (i) −x, −y+3, −z; (ii) x, y−1, z. |
Acknowledgements
This research work was supported 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 (08KJA530002).
References
Enraf–Nonius (1994). CAD-4 EXPRESS. 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
Kurt, T., Ludwig, 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
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.
Azole derivatives such as Voriconazole and Ketoconazole are safe and effective antifungal agents (Jeu et al., 2003; Fromtling & Castaner,1996). As part of our studies on the synthesis of new azole derivatives, the crystal structure of the title compound was determined.
In the molecular structure of the title compound (Fig. 1) the double bond is Z configurated. 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). The bond lengths and bpnd angles in the title compound agree with the corresponding bond lengths and angles reported for a closely related compound (Kurt et al., 1987).