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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3084.
Published online 2010 November 6. doi:  10.1107/S160053681004465X
PMCID: PMC3011382

4-(3-Fluoro-4-meth­oxy­phen­yl)-1-(4-meth­oxy­phen­yl)-5-(3,4,5-trimeth­oxy­phen­yl)-1H-imidazole

Abstract

In the title mol­ecule, C26H25FN2O5, the fluoro­meth­oxy-, meth­oxy- and trimeth­oxy-substituted benzene rings form dihedral angles of 12.65 (2), 84.15 (2) and 55.67 (2)°, respectively, with the imidazole ring. The crystal structure is stabilized weak inter­molecular C—H(...)F and C—H(...)O hydrogen bonds.

Related literature

For general background to the pharmacological activity of imidazole derivatives, see: Bellina et al. (2006 [triangle], 2007 [triangle]); Cai et al. (2009 [triangle]). For background to synthetic methods for imidizoles, see: Bräuer et al. (2005 [triangle]), Wang et al. (2002 [triangle]).

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Object name is e-66-o3084-scheme1.jpg

Experimental

Crystal data

  • C26H25FN2O5
  • M r = 464.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3084-efi1.jpg
  • a = 9.795 (2) Å
  • b = 10.202 (2) Å
  • c = 13.008 (3) Å
  • α = 104.76 (3)°
  • β = 109.81 (3)°
  • γ = 91.45 (3)°
  • V = 1173.7 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.972, T max = 0.981
  • 4540 measured reflections
  • 4269 independent reflections
  • 2838 reflections with I > 2σ(I)
  • R int = 0.024
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.178
  • S = 1.00
  • 4269 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004465X/lh5129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004465X/lh5129Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Imidazole derivatives have been shown to exhibit interesting biological activities such as antimicrobial, anticryptococcal, inhibition of nitric oxide synthase, as inhibitors of p38 MAP kinase and cytotoxic activities (Bellina et al., 2006; Bellina et al., 2007; Cai et al., 2009). Owing to these wide range of pharmacological and biological activities, the synthesis of imidazoles has become important (Bräuer et al.,2005; Wang et al., 2002). Herein we present the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The dihedral angles that the fluoromethoxy, methoxy and trimethoxy-substituted, benzene rings form with the imidazole ring are 12.65 (2), 84.15 (2) and 55.67 (2)Å, respectively. The crystal structure is stabilized weak intermolecular C—H···F and C—H···N hydrogen bonds. .

Experimental

To a solution of 4-methoxyaniline in (2.46 g, 20 mmol) in 5 ml/mmol methanol 3,4,5-trimethoxybenzaldehyde (3.92 g, 20 mmol) was added and stirred at room temperature. After 2 h the mixture was treated with 3,4,5-Trimethoxyphenyl(tosyl)methyl isocyanide (7.20 g, 20 mmol) and triethylamine (4.04 g, 40 mmol) and then heated under reflux for 8 h until the conversion of the starting material was complete. For the plate syntheses the reaction mixtures were heated on a sealed deep-well plate in a water bath at 323 K overnight. Aqueous workup was performed in the case of single reactions by adding ethyl acetate and washing the organic layer with 1 M aqueous HCl solution and aqueous NaCl solution. The organic layers were dried over anhydrous sodium sulfate and filtered. The filtrates were concentrated under vacuum, and purified using chromatographic methods described below. (Yield: 4.80 g, 51.9%; white solid; Mp. 429–430 K).

Refinement

All the hydrogen atoms were placed in caculated positions with C—H = 0.93Å (aromatic) and 0.96Å (methyl) and Uiso(H) = 1.2Ueq(C) (aromatic C) and 1.5Ueq(C) (methyl C).

Figures

Fig. 1.
The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.

Crystal data

C26H25FN2O5Z = 2
Mr = 464.48F(000) = 488
Triclinic, P1Dx = 1.314 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.795 (2) ÅCell parameters from 25 reflections
b = 10.202 (2) Åθ = 9–13°
c = 13.008 (3) ŵ = 0.10 mm1
α = 104.76 (3)°T = 293 K
β = 109.81 (3)°Block, colourless
γ = 91.45 (3)°0.30 × 0.20 × 0.20 mm
V = 1173.7 (4) Å3

Data collection

Enraf–Nonius CAD-4 diffractometer2838 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 25.3°, θmin = 1.7°
ω/–2θ scansh = 0→11
Absorption correction: ψ scan (North et al., 1968)k = −12→12
Tmin = 0.972, Tmax = 0.981l = −15→14
4540 measured reflections3 standard reflections every 200 reflections
4269 independent reflections intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.178w = 1/[σ2(Fo2) + (0.070P)2 + 1.1P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4269 reflectionsΔρmax = 0.23 e Å3
308 parametersΔρmin = −0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.063 (5)

Special details

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)

xyzUiso*/Ueq
F−0.1298 (3)0.7973 (2)−0.06705 (17)0.0787 (7)
N10.2523 (3)0.9865 (2)0.5152 (2)0.0456 (6)
O10.5861 (3)1.1432 (3)0.9767 (2)0.0814 (8)
C10.5238 (6)1.2059 (5)1.0579 (3)0.0915 (14)
H1A0.59751.22931.13270.137*
H1B0.44601.14371.05430.137*
H1C0.48591.28721.04170.137*
N20.1490 (3)1.0175 (2)0.3441 (2)0.0504 (7)
O2−0.2366 (3)0.5452 (3)−0.0943 (2)0.0697 (7)
C20.4976 (4)1.1028 (3)0.8645 (3)0.0549 (8)
O30.3163 (3)0.3936 (2)0.44874 (19)0.0619 (7)
C30.5629 (4)1.0514 (4)0.7881 (3)0.0702 (11)
H3A0.66251.04360.81410.084*
O40.2214 (3)0.4035 (2)0.61811 (19)0.0558 (6)
C40.4832 (4)1.0104 (4)0.6723 (3)0.0607 (9)
H4A0.52870.97530.62070.073*
O50.1123 (3)0.6229 (2)0.7079 (2)0.0610 (7)
C50.3357 (3)1.0222 (3)0.6343 (3)0.0447 (7)
C60.2704 (4)1.0724 (3)0.7116 (3)0.0544 (8)
H6A0.17071.07950.68610.065*
C70.3502 (4)1.1125 (3)0.8265 (3)0.0575 (9)
H7A0.30461.14620.87820.069*
C80.1876 (3)0.8580 (3)0.4414 (2)0.0423 (7)
C90.1239 (3)0.8803 (3)0.3364 (3)0.0429 (7)
C100.2242 (4)1.0762 (3)0.4503 (3)0.0520 (8)
H10A0.25571.16940.47950.062*
C110.0325 (3)0.7870 (3)0.2272 (3)0.0432 (7)
C12−0.0271 (4)0.6560 (3)0.2128 (3)0.0491 (8)
H12A−0.00590.62300.27620.059*
C13−0.1153 (4)0.5736 (3)0.1099 (3)0.0552 (8)
H13A−0.15270.48640.10450.066*
C14−0.1503 (4)0.6184 (3)0.0124 (3)0.0528 (8)
C15−0.0923 (4)0.7503 (3)0.0273 (3)0.0516 (8)
C16−0.0043 (4)0.8328 (3)0.1282 (3)0.0482 (8)
H16A0.03250.91990.13310.058*
C17−0.2849 (5)0.4069 (4)−0.1106 (3)0.0742 (11)
H17A−0.34440.3664−0.18900.111*
H17B−0.34120.4023−0.06360.111*
H17C−0.20180.3582−0.09010.111*
C180.1942 (3)0.7367 (3)0.4859 (2)0.0424 (7)
C190.1424 (3)0.7387 (3)0.5724 (3)0.0464 (7)
H19A0.09950.81330.59990.056*
C200.1548 (3)0.6278 (3)0.6190 (3)0.0455 (7)
C210.2126 (3)0.5149 (3)0.5745 (3)0.0444 (7)
C220.2609 (3)0.5107 (3)0.4851 (3)0.0457 (7)
C230.2545 (3)0.6233 (3)0.4415 (3)0.0451 (7)
H23A0.29010.62270.38360.054*
C240.3521 (5)0.3753 (4)0.3498 (3)0.0719 (11)
H24A0.38970.28940.33410.108*
H24B0.42480.44800.36160.108*
H24C0.26610.37610.28650.108*
C250.3515 (5)0.4118 (4)0.7100 (3)0.0786 (12)
H25A0.35070.33180.73590.118*
H25B0.35950.49150.77080.118*
H25C0.43340.41760.68590.118*
C260.0553 (5)0.7381 (4)0.7569 (4)0.0830 (13)
H26A0.02990.72190.81810.125*
H26B−0.03020.75400.70020.125*
H26C0.12760.81660.78580.125*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F0.1042 (17)0.0838 (15)0.0550 (12)0.0114 (13)0.0226 (12)0.0389 (11)
N10.0594 (16)0.0340 (13)0.0464 (15)0.0092 (11)0.0185 (13)0.0167 (11)
O10.0788 (19)0.0852 (19)0.0605 (17)0.0057 (15)0.0072 (15)0.0113 (14)
C10.123 (4)0.085 (3)0.052 (2)0.019 (3)0.024 (3)0.005 (2)
N20.0684 (18)0.0358 (13)0.0547 (17)0.0137 (12)0.0234 (14)0.0232 (12)
O20.0814 (18)0.0646 (16)0.0522 (15)0.0070 (13)0.0110 (13)0.0156 (12)
C20.061 (2)0.0477 (19)0.0484 (19)0.0045 (16)0.0119 (17)0.0108 (15)
O30.1000 (19)0.0350 (12)0.0610 (15)0.0220 (12)0.0352 (14)0.0209 (10)
C30.049 (2)0.083 (3)0.071 (3)0.0134 (19)0.0136 (19)0.020 (2)
O40.0710 (15)0.0387 (11)0.0615 (14)0.0044 (10)0.0172 (12)0.0295 (10)
C40.060 (2)0.065 (2)0.062 (2)0.0126 (17)0.0282 (19)0.0176 (18)
O50.0809 (17)0.0573 (14)0.0681 (15)0.0218 (12)0.0422 (13)0.0346 (12)
C50.0514 (19)0.0316 (15)0.0519 (18)0.0052 (13)0.0165 (15)0.0155 (13)
C60.0480 (19)0.054 (2)0.061 (2)0.0133 (15)0.0212 (17)0.0119 (16)
C70.065 (2)0.054 (2)0.054 (2)0.0107 (17)0.0245 (18)0.0133 (16)
C80.0473 (17)0.0326 (15)0.0496 (18)0.0093 (13)0.0179 (14)0.0149 (13)
C90.0481 (18)0.0360 (15)0.0533 (18)0.0134 (13)0.0222 (15)0.0211 (14)
C100.071 (2)0.0333 (16)0.057 (2)0.0118 (15)0.0236 (18)0.0201 (15)
C110.0494 (18)0.0431 (17)0.0466 (17)0.0145 (14)0.0221 (14)0.0212 (14)
C120.059 (2)0.0487 (18)0.0434 (18)0.0085 (15)0.0148 (15)0.0235 (15)
C130.058 (2)0.0478 (19)0.057 (2)0.0069 (16)0.0150 (17)0.0185 (16)
C140.053 (2)0.058 (2)0.0455 (19)0.0140 (16)0.0131 (16)0.0155 (16)
C150.066 (2)0.059 (2)0.0451 (19)0.0219 (17)0.0278 (17)0.0281 (16)
C160.059 (2)0.0453 (17)0.0514 (19)0.0146 (15)0.0286 (16)0.0203 (15)
C170.074 (3)0.064 (2)0.067 (2)0.009 (2)0.009 (2)0.0104 (19)
C180.0471 (17)0.0318 (15)0.0469 (17)0.0044 (13)0.0122 (14)0.0149 (13)
C190.0529 (19)0.0378 (16)0.0532 (18)0.0113 (14)0.0210 (15)0.0177 (14)
C200.0471 (18)0.0424 (17)0.0512 (18)0.0032 (14)0.0172 (15)0.0207 (14)
C210.0501 (18)0.0338 (15)0.0476 (17)0.0015 (13)0.0099 (14)0.0194 (13)
C220.0550 (19)0.0325 (15)0.0460 (17)0.0070 (13)0.0115 (15)0.0138 (13)
C230.0574 (19)0.0376 (16)0.0449 (17)0.0096 (14)0.0184 (15)0.0187 (13)
C240.107 (3)0.052 (2)0.069 (2)0.026 (2)0.045 (2)0.0175 (18)
C250.082 (3)0.073 (3)0.081 (3)0.006 (2)0.005 (2)0.053 (2)
C260.108 (3)0.092 (3)0.094 (3)0.049 (3)0.067 (3)0.056 (3)

Geometric parameters (Å, °)

F—C151.369 (3)C9—C111.459 (4)
N1—C101.369 (4)C10—H10A0.9300
N1—C81.395 (4)C11—C121.387 (4)
N1—C51.429 (4)C11—C161.416 (4)
O1—C21.367 (4)C12—C131.360 (4)
O1—C11.418 (5)C12—H12A0.9300
C1—H1A0.9600C13—C141.394 (4)
C1—H1B0.9600C13—H13A0.9300
C1—H1C0.9600C14—C151.387 (5)
N2—C101.295 (4)C15—C161.345 (5)
N2—C91.388 (4)C16—H16A0.9300
O2—C141.358 (4)C17—H17A0.9600
O2—C171.417 (4)C17—H17B0.9600
C2—C31.361 (5)C17—H17C0.9600
C2—C71.374 (5)C18—C191.379 (4)
O3—C221.365 (4)C18—C231.395 (4)
O3—C241.415 (4)C19—C201.403 (4)
C3—C41.385 (5)C19—H19A0.9300
C3—H3A0.9300C20—C211.377 (4)
O4—C211.386 (3)C21—C221.389 (4)
O4—C251.404 (4)C22—C231.398 (4)
C4—C51.380 (5)C23—H23A0.9300
C4—H4A0.9300C24—H24A0.9600
O5—C201.366 (4)C24—H24B0.9600
O5—C261.411 (4)C24—H24C0.9600
C5—C61.367 (4)C25—H25A0.9600
C6—C71.376 (5)C25—H25B0.9600
C6—H6A0.9300C25—H25C0.9600
C7—H7A0.9300C26—H26A0.9600
C8—C91.377 (4)C26—H26B0.9600
C8—C181.488 (4)C26—H26C0.9600
C10—N1—C8106.4 (2)O2—C14—C15117.8 (3)
C10—N1—C5124.9 (3)O2—C14—C13125.8 (3)
C8—N1—C5128.6 (2)C15—C14—C13116.4 (3)
C2—O1—C1118.1 (3)C16—C15—F119.4 (3)
O1—C1—H1A109.5C16—C15—C14123.6 (3)
O1—C1—H1B109.5F—C15—C14117.0 (3)
H1A—C1—H1B109.5C15—C16—C11120.1 (3)
O1—C1—H1C109.5C15—C16—H16A120.0
H1A—C1—H1C109.5C11—C16—H16A120.0
H1B—C1—H1C109.5O2—C17—H17A109.5
C10—N2—C9105.5 (2)O2—C17—H17B109.5
C14—O2—C17117.4 (3)H17A—C17—H17B109.5
C3—C2—O1116.5 (3)O2—C17—H17C109.5
C3—C2—C7119.7 (3)H17A—C17—H17C109.5
O1—C2—C7123.8 (3)H17B—C17—H17C109.5
C22—O3—C24118.2 (2)C19—C18—C23120.5 (3)
C2—C3—C4120.9 (3)C19—C18—C8119.3 (3)
C2—C3—H3A119.5C23—C18—C8120.1 (3)
C4—C3—H3A119.5C18—C19—C20119.9 (3)
C21—O4—C25113.7 (2)C18—C19—H19A120.1
C5—C4—C3119.3 (3)C20—C19—H19A120.1
C5—C4—H4A120.4O5—C20—C21116.2 (3)
C3—C4—H4A120.4O5—C20—C19124.1 (3)
C20—O5—C26117.6 (3)C21—C20—C19119.7 (3)
C6—C5—C4119.5 (3)C20—C21—O4120.0 (3)
C6—C5—N1120.1 (3)C20—C21—C22120.6 (3)
C4—C5—N1120.4 (3)O4—C21—C22119.4 (3)
C5—C6—C7120.9 (3)O3—C22—C21115.0 (3)
C5—C6—H6A119.6O3—C22—C23125.1 (3)
C7—C6—H6A119.6C21—C22—C23119.8 (3)
C2—C7—C6119.7 (3)C18—C23—C22119.3 (3)
C2—C7—H7A120.1C18—C23—H23A120.3
C6—C7—H7A120.1C22—C23—H23A120.3
C9—C8—N1104.9 (2)O3—C24—H24A109.5
C9—C8—C18134.8 (3)O3—C24—H24B109.5
N1—C8—C18120.2 (3)H24A—C24—H24B109.5
C8—C9—N2110.4 (3)O3—C24—H24C109.5
C8—C9—C11130.6 (3)H24A—C24—H24C109.5
N2—C9—C11118.9 (3)H24B—C24—H24C109.5
N2—C10—N1112.8 (3)O4—C25—H25A109.5
N2—C10—H10A123.6O4—C25—H25B109.5
N1—C10—H10A123.6H25A—C25—H25B109.5
C12—C11—C16116.3 (3)O4—C25—H25C109.5
C12—C11—C9124.6 (3)H25A—C25—H25C109.5
C16—C11—C9119.0 (3)H25B—C25—H25C109.5
C13—C12—C11122.8 (3)O5—C26—H26A109.5
C13—C12—H12A118.6O5—C26—H26B109.5
C11—C12—H12A118.6H26A—C26—H26B109.5
C12—C13—C14120.7 (3)O5—C26—H26C109.5
C12—C13—H13A119.6H26A—C26—H26C109.5
C14—C13—H13A119.6H26B—C26—H26C109.5
C1—O1—C2—C3175.7 (4)C17—O2—C14—C13−6.2 (5)
C1—O1—C2—C7−3.7 (5)C12—C13—C14—O2179.9 (3)
O1—C2—C3—C4−178.6 (3)C12—C13—C14—C15−1.0 (5)
C7—C2—C3—C40.9 (6)O2—C14—C15—C16−179.3 (3)
C2—C3—C4—C50.1 (6)C13—C14—C15—C161.4 (5)
C3—C4—C5—C6−0.9 (5)O2—C14—C15—F1.4 (5)
C3—C4—C5—N1177.2 (3)C13—C14—C15—F−177.9 (3)
C10—N1—C5—C683.9 (4)F—C15—C16—C11178.4 (3)
C8—N1—C5—C6−97.9 (4)C14—C15—C16—C11−0.9 (5)
C10—N1—C5—C4−94.1 (4)C12—C11—C16—C15−0.1 (4)
C8—N1—C5—C484.1 (4)C9—C11—C16—C15−177.8 (3)
C4—C5—C6—C70.7 (5)C9—C8—C18—C19−121.5 (4)
N1—C5—C6—C7−177.3 (3)N1—C8—C18—C1955.6 (4)
C3—C2—C7—C6−1.1 (5)C9—C8—C18—C2359.6 (5)
O1—C2—C7—C6178.4 (3)N1—C8—C18—C23−123.3 (3)
C5—C6—C7—C20.3 (5)C23—C18—C19—C202.1 (5)
C10—N1—C8—C9−0.3 (3)C8—C18—C19—C20−176.8 (3)
C5—N1—C8—C9−178.7 (3)C26—O5—C20—C21178.7 (3)
C10—N1—C8—C18−178.2 (3)C26—O5—C20—C19−1.3 (5)
C5—N1—C8—C183.4 (5)C18—C19—C20—O5177.2 (3)
N1—C8—C9—N20.5 (3)C18—C19—C20—C21−2.9 (5)
C18—C8—C9—N2177.9 (3)O5—C20—C21—O41.7 (4)
N1—C8—C9—C11−175.5 (3)C19—C20—C21—O4−178.2 (3)
C18—C8—C9—C112.0 (6)O5—C20—C21—C22−179.1 (3)
C10—N2—C9—C8−0.5 (4)C19—C20—C21—C221.0 (5)
C10—N2—C9—C11176.0 (3)C25—O4—C21—C20−88.7 (4)
C9—N2—C10—N10.4 (4)C25—O4—C21—C2292.1 (4)
C8—N1—C10—N2−0.1 (4)C24—O3—C22—C21172.9 (3)
C5—N1—C10—N2178.5 (3)C24—O3—C22—C23−9.1 (5)
C8—C9—C11—C1210.4 (5)C20—C21—C22—O3179.8 (3)
N2—C9—C11—C12−165.3 (3)O4—C21—C22—O3−1.0 (4)
C8—C9—C11—C16−172.2 (3)C20—C21—C22—C231.7 (5)
N2—C9—C11—C1612.1 (4)O4—C21—C22—C23−179.1 (3)
C16—C11—C12—C130.6 (5)C19—C18—C23—C220.6 (4)
C9—C11—C12—C13178.1 (3)C8—C18—C23—C22179.4 (3)
C11—C12—C13—C140.0 (5)O3—C22—C23—C18179.6 (3)
C17—O2—C14—C15174.6 (3)C21—C22—C23—C18−2.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10A···O3i0.932.513.346 (4)150
C26—H26A···Fii0.962.523.326 (6)142

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5129).

References

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