Acta Cryst. (2010). E66, o320 [ doi:10.1107/S1600536809055524 ]
In the title compound, C26H16FN3O3, the dihedral angle between the anthryl and fluorophenyl groups is 37.8 (1)°. With respect to the imidazolyl group, the twist angles between the imidazolyl group and the anthryl unit and between the imidazoly group and the fluorophenyl group are 64.4 (1) and 74.5 (1)°, respectively.
Compound (I) was synthesized according to the procedure of Erhardt et al. (1985) and Kranz et al. (1980). Single crystals (I) suitable for X-ray analysis were grown in dichloromethane by slow evaporation at room temperature.
Hydrogen atoms were placed in calculated positions with C—H = 0.95Å (aromatic ring) with Uiso(H) = 1.2Ueq(C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./ng2707fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing theatom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./ng2707fig2thm.gif)
| Fig. 2. Part of the CrystalStructure of (I), showing the formation of the three-dimensional network. |
| C26H16FN3O3 | Z = 2 |
| Mr = 437.42 | F(000) = 452 |
| Triclinic, P1 | Dx = 1.423 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.3362 (6) Å | Cell parameters from 8826 reflections |
| b = 10.9587 (6) Å | θ = 2.8–27.0° |
| c = 11.6018 (5) Å | µ = 0.10 mm−1 |
| α = 70.371 (5)° | T = 173 K |
| β = 88.062 (4)° | Block, yellow |
| γ = 66.781 (6)° | 0.49 × 0.41 × 0.30 mm |
| V = 1020.78 (10) Å3 |
| Oxford Diffraction Xcaliber diffractometer | 4374 independent reflections |
| Radiation source: fine-focus sealed tube | 3193 reflections with I > 2σ(I) |
| graphite | Rint = 0.020 |
| Detector resolution: 0.01 pixels mm-1 | θmax = 27.0°, θmin = 2.8° |
| ω scans | h = −11→11 |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −13→12 |
| Tmin = 0.951, Tmax = 0.970 | l = −14→14 |
| 8826 measured reflections |
| 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.090 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3 |
| 4374 reflections | (Δ/σ)max = 0.001 |
| 298 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C26H16FN3O3 | γ = 66.781 (6)° |
| Mr = 437.42 | V = 1020.78 (10) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.3362 (6) Å | Mo Kα radiation |
| b = 10.9587 (6) Å | µ = 0.10 mm−1 |
| c = 11.6018 (5) Å | T = 173 K |
| α = 70.371 (5)° | 0.49 × 0.41 × 0.30 mm |
| β = 88.062 (4)° |
| Oxford Diffraction Xcaliber diffractometer | 4374 independent reflections |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 3193 reflections with I > 2σ(I) |
| Tmin = 0.951, Tmax = 0.970 | Rint = 0.020 |
| 8826 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.090 | Δρmax = 0.22 e Å−3 |
| S = 1.01 | Δρmin = −0.19 e Å−3 |
| 4374 reflections | Absolute structure: ? |
| 298 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| F1 | 0.40315 (10) | 0.15681 (10) | 1.18206 (7) | 0.0560 (3) | |
| O1 | 0.12744 (13) | −0.02448 (11) | 0.81580 (8) | 0.0455 (3) | |
| N3 | 0.19905 (12) | 0.08673 (11) | 0.58002 (8) | 0.0261 (2) | |
| C15 | 0.10394 (14) | 0.30540 (13) | 0.61663 (11) | 0.0282 (3) | |
| H15A | 0.1064 | 0.3481 | 0.5309 | 0.034* | |
| C17 | 0.16584 (14) | 0.07397 (13) | 0.79428 (10) | 0.0275 (3) | |
| C23 | 0.33391 (14) | 0.16396 (13) | 0.87665 (11) | 0.0270 (3) | |
| H23A | 0.3671 | 0.1929 | 0.7975 | 0.032* | |
| C14 | 0.04204 (14) | 0.40033 (13) | 0.68792 (10) | 0.0272 (3) | |
| C6 | −0.08868 (15) | 0.40198 (13) | 0.75307 (10) | 0.0282 (3) | |
| C18 | 0.22475 (14) | 0.10459 (12) | 0.89378 (10) | 0.0244 (3) | |
| C7 | 0.11980 (15) | 0.48598 (13) | 0.69277 (11) | 0.0291 (3) | |
| C22 | 0.39456 (15) | 0.18126 (13) | 0.97408 (12) | 0.0333 (3) | |
| H22A | 0.4704 | 0.2207 | 0.9636 | 0.040* | |
| N2 | 0.18404 (14) | 0.02358 (13) | 0.41956 (9) | 0.0390 (3) | |
| C19 | 0.17599 (15) | 0.06337 (14) | 1.01033 (10) | 0.0323 (3) | |
| H19A | 0.1023 | 0.0216 | 1.0226 | 0.039* | |
| C12 | 0.07161 (15) | 0.56901 (13) | 0.77072 (11) | 0.0326 (3) | |
| C16 | 0.15658 (14) | 0.16506 (13) | 0.66238 (10) | 0.0255 (3) | |
| C26 | 0.32395 (15) | −0.05927 (13) | 0.49025 (10) | 0.0295 (3) | |
| O2 | 0.56329 (12) | −0.24366 (12) | 0.53163 (10) | 0.0525 (3) | |
| C8 | 0.25072 (16) | 0.48911 (14) | 0.62676 (12) | 0.0368 (3) | |
| H8A | 0.2838 | 0.4365 | 0.5731 | 0.044* | |
| C1 | −0.13552 (15) | 0.48673 (14) | 0.83035 (11) | 0.0330 (3) | |
| C20 | 0.23331 (16) | 0.08250 (15) | 1.10757 (11) | 0.0368 (3) | |
| H20A | 0.1986 | 0.0568 | 1.1866 | 0.044* | |
| C21 | 0.34228 (15) | 0.13994 (14) | 1.08624 (11) | 0.0346 (3) | |
| O3 | 0.41958 (15) | −0.18717 (12) | 0.36400 (9) | 0.0656 (4) | |
| C13 | −0.05363 (16) | 0.56575 (14) | 0.83786 (12) | 0.0358 (3) | |
| H13A | −0.0842 | 0.6195 | 0.8907 | 0.043* | |
| C5 | −0.17915 (15) | 0.32560 (14) | 0.74550 (12) | 0.0343 (3) | |
| H5A | −0.1529 | 0.2715 | 0.6929 | 0.041* | |
| C2 | −0.26464 (17) | 0.48480 (16) | 0.89925 (13) | 0.0437 (4) | |
| H2A | −0.2949 | 0.5386 | 0.9521 | 0.052* | |
| C11 | 0.15633 (17) | 0.64982 (15) | 0.77975 (12) | 0.0405 (3) | |
| H11A | 0.1242 | 0.7063 | 0.8303 | 0.049* | |
| C9 | 0.32888 (18) | 0.56622 (15) | 0.63942 (13) | 0.0450 (4) | |
| H9A | 0.4165 | 0.5659 | 0.5953 | 0.054* | |
| C4 | −0.30200 (17) | 0.32892 (16) | 0.81208 (13) | 0.0433 (4) | |
| H4A | −0.3604 | 0.2770 | 0.8057 | 0.052* | |
| C10 | 0.28170 (19) | 0.64686 (16) | 0.71722 (13) | 0.0472 (4) | |
| H10A | 0.3384 | 0.6994 | 0.7257 | 0.057* | |
| C3 | −0.34423 (18) | 0.40905 (17) | 0.89124 (14) | 0.0484 (4) | |
| H3A | −0.4292 | 0.4089 | 0.9387 | 0.058* | |
| N1 | 0.44252 (15) | −0.17030 (13) | 0.45944 (10) | 0.0389 (3) | |
| C25 | 0.33644 (15) | −0.02437 (13) | 0.58946 (11) | 0.0294 (3) | |
| H25A | 0.4225 | −0.0681 | 0.6519 | 0.035* | |
| C24 | 0.11069 (16) | 0.11104 (15) | 0.47696 (11) | 0.0357 (3) | |
| H24A | 0.0077 | 0.1832 | 0.4500 | 0.043* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| F1 | 0.0625 (6) | 0.0621 (6) | 0.0440 (5) | −0.0166 (5) | −0.0174 (4) | −0.0276 (5) |
| O1 | 0.0783 (8) | 0.0471 (6) | 0.0291 (5) | −0.0426 (6) | 0.0100 (5) | −0.0145 (5) |
| N3 | 0.0312 (6) | 0.0287 (6) | 0.0189 (5) | −0.0111 (5) | 0.0027 (4) | −0.0102 (4) |
| C15 | 0.0326 (7) | 0.0304 (7) | 0.0205 (6) | −0.0121 (6) | 0.0030 (5) | −0.0088 (5) |
| C17 | 0.0327 (7) | 0.0276 (7) | 0.0239 (6) | −0.0126 (6) | 0.0054 (5) | −0.0108 (5) |
| C23 | 0.0278 (6) | 0.0230 (6) | 0.0263 (6) | −0.0074 (5) | 0.0035 (5) | −0.0077 (5) |
| C14 | 0.0313 (7) | 0.0220 (6) | 0.0214 (6) | −0.0051 (5) | −0.0018 (5) | −0.0057 (5) |
| C6 | 0.0308 (7) | 0.0245 (6) | 0.0234 (6) | −0.0056 (6) | −0.0015 (5) | −0.0075 (5) |
| C18 | 0.0259 (6) | 0.0228 (6) | 0.0205 (6) | −0.0052 (5) | 0.0008 (5) | −0.0083 (5) |
| C7 | 0.0330 (7) | 0.0205 (6) | 0.0246 (6) | −0.0057 (6) | −0.0036 (5) | −0.0026 (5) |
| C22 | 0.0286 (7) | 0.0277 (7) | 0.0419 (7) | −0.0081 (6) | −0.0036 (6) | −0.0135 (6) |
| N2 | 0.0484 (7) | 0.0445 (7) | 0.0244 (5) | −0.0142 (6) | 0.0014 (5) | −0.0177 (5) |
| C19 | 0.0353 (7) | 0.0393 (8) | 0.0243 (6) | −0.0178 (6) | 0.0060 (5) | −0.0107 (6) |
| C12 | 0.0377 (7) | 0.0225 (6) | 0.0302 (6) | −0.0066 (6) | −0.0049 (6) | −0.0065 (5) |
| C16 | 0.0290 (6) | 0.0291 (7) | 0.0209 (6) | −0.0117 (6) | 0.0044 (5) | −0.0122 (5) |
| C26 | 0.0372 (7) | 0.0302 (7) | 0.0245 (6) | −0.0151 (6) | 0.0099 (5) | −0.0127 (5) |
| O2 | 0.0431 (6) | 0.0485 (7) | 0.0645 (7) | −0.0085 (6) | 0.0074 (6) | −0.0305 (6) |
| C8 | 0.0407 (8) | 0.0285 (7) | 0.0353 (7) | −0.0119 (6) | 0.0036 (6) | −0.0069 (6) |
| C1 | 0.0354 (7) | 0.0281 (7) | 0.0298 (6) | −0.0055 (6) | 0.0014 (6) | −0.0121 (6) |
| C20 | 0.0419 (8) | 0.0438 (8) | 0.0208 (6) | −0.0119 (7) | 0.0033 (6) | −0.0131 (6) |
| C21 | 0.0353 (7) | 0.0334 (7) | 0.0298 (7) | −0.0028 (6) | −0.0101 (6) | −0.0166 (6) |
| O3 | 0.0953 (9) | 0.0581 (7) | 0.0393 (6) | −0.0133 (7) | 0.0112 (6) | −0.0341 (6) |
| C13 | 0.0430 (8) | 0.0282 (7) | 0.0336 (7) | −0.0073 (6) | 0.0005 (6) | −0.0160 (6) |
| C5 | 0.0349 (7) | 0.0352 (7) | 0.0345 (7) | −0.0116 (6) | 0.0036 (6) | −0.0173 (6) |
| C2 | 0.0483 (9) | 0.0418 (8) | 0.0443 (8) | −0.0138 (7) | 0.0155 (7) | −0.0254 (7) |
| C11 | 0.0521 (9) | 0.0298 (7) | 0.0375 (7) | −0.0148 (7) | −0.0069 (7) | −0.0100 (6) |
| C9 | 0.0450 (9) | 0.0385 (8) | 0.0485 (8) | −0.0202 (7) | 0.0043 (7) | −0.0077 (7) |
| C4 | 0.0401 (8) | 0.0457 (9) | 0.0535 (9) | −0.0208 (7) | 0.0118 (7) | −0.0253 (7) |
| C10 | 0.0545 (10) | 0.0359 (8) | 0.0505 (9) | −0.0245 (8) | −0.0082 (8) | −0.0058 (7) |
| C3 | 0.0439 (9) | 0.0539 (10) | 0.0549 (9) | −0.0196 (8) | 0.0226 (7) | −0.0301 (8) |
| N1 | 0.0520 (8) | 0.0349 (7) | 0.0357 (6) | −0.0196 (6) | 0.0167 (6) | −0.0184 (6) |
| C25 | 0.0311 (7) | 0.0282 (7) | 0.0286 (6) | −0.0099 (6) | 0.0008 (5) | −0.0120 (6) |
| C24 | 0.0371 (8) | 0.0422 (8) | 0.0240 (6) | −0.0100 (7) | −0.0023 (6) | −0.0140 (6) |
| F1—C21 | 1.3626 (13) | C12—C11 | 1.4288 (18) |
| O1—C17 | 1.2135 (14) | C26—C25 | 1.3508 (15) |
| N3—C25 | 1.3521 (16) | C26—N1 | 1.4272 (17) |
| N3—C24 | 1.3641 (15) | O2—N1 | 1.2312 (15) |
| N3—C16 | 1.4367 (14) | C8—C9 | 1.3583 (18) |
| C15—C16 | 1.3273 (17) | C8—H8A | 0.9500 |
| C15—C14 | 1.4739 (16) | C1—C13 | 1.3854 (18) |
| C15—H15A | 0.9500 | C1—C2 | 1.4270 (19) |
| C17—C18 | 1.4821 (15) | C20—C21 | 1.3696 (19) |
| C17—C16 | 1.5034 (16) | C20—H20A | 0.9500 |
| C23—C22 | 1.3806 (16) | O3—N1 | 1.2210 (13) |
| C23—C18 | 1.3869 (16) | C13—H13A | 0.9500 |
| C23—H23A | 0.9500 | C5—C4 | 1.3563 (18) |
| C14—C7 | 1.4095 (17) | C5—H5A | 0.9500 |
| C14—C6 | 1.4109 (17) | C2—C3 | 1.339 (2) |
| C6—C5 | 1.4260 (17) | C2—H2A | 0.9500 |
| C6—C1 | 1.4389 (16) | C11—C10 | 1.351 (2) |
| C18—C19 | 1.3963 (16) | C11—H11A | 0.9500 |
| C7—C8 | 1.4262 (18) | C9—C10 | 1.411 (2) |
| C7—C12 | 1.4319 (17) | C9—H9A | 0.9500 |
| C22—C21 | 1.3682 (18) | C4—C3 | 1.4192 (19) |
| C22—H22A | 0.9500 | C4—H4A | 0.9500 |
| N2—C24 | 1.3082 (16) | C10—H10A | 0.9500 |
| N2—C26 | 1.3565 (16) | C3—H3A | 0.9500 |
| C19—C20 | 1.3752 (16) | C25—H25A | 0.9500 |
| C19—H19A | 0.9500 | C24—H24A | 0.9500 |
| C12—C13 | 1.3885 (18) | ||
| C25—N3—C24 | 106.98 (10) | C13—C1—C2 | 121.72 (11) |
| C25—N3—C16 | 126.08 (10) | C13—C1—C6 | 119.74 (12) |
| C24—N3—C16 | 126.93 (11) | C2—C1—C6 | 118.54 (12) |
| C16—C15—C14 | 125.33 (11) | C21—C20—C19 | 117.49 (12) |
| C16—C15—H15A | 117.3 | C21—C20—H20A | 121.3 |
| C14—C15—H15A | 117.3 | C19—C20—H20A | 121.3 |
| O1—C17—C18 | 121.96 (11) | F1—C21—C22 | 117.71 (12) |
| O1—C17—C16 | 118.70 (10) | F1—C21—C20 | 118.41 (11) |
| C18—C17—C16 | 119.33 (10) | C22—C21—C20 | 123.89 (11) |
| C22—C23—C18 | 120.32 (11) | C1—C13—C12 | 122.18 (11) |
| C22—C23—H23A | 119.8 | C1—C13—H13A | 118.9 |
| C18—C23—H23A | 119.8 | C12—C13—H13A | 118.9 |
| C7—C14—C6 | 120.79 (10) | C4—C5—C6 | 121.13 (12) |
| C7—C14—C15 | 118.37 (11) | C4—C5—H5A | 119.4 |
| C6—C14—C15 | 120.80 (11) | C6—C5—H5A | 119.4 |
| C14—C6—C5 | 123.66 (11) | C3—C2—C1 | 121.60 (12) |
| C14—C6—C1 | 118.58 (11) | C3—C2—H2A | 119.2 |
| C5—C6—C1 | 117.76 (11) | C1—C2—H2A | 119.2 |
| C23—C18—C19 | 119.36 (11) | C10—C11—C12 | 120.76 (13) |
| C23—C18—C17 | 122.07 (10) | C10—C11—H11A | 119.6 |
| C19—C18—C17 | 118.43 (11) | C12—C11—H11A | 119.6 |
| C14—C7—C8 | 122.54 (11) | C8—C9—C10 | 120.93 (14) |
| C14—C7—C12 | 119.57 (11) | C8—C9—H9A | 119.5 |
| C8—C7—C12 | 117.84 (11) | C10—C9—H9A | 119.5 |
| C21—C22—C23 | 118.05 (12) | C5—C4—C3 | 120.74 (13) |
| C21—C22—H22A | 121.0 | C5—C4—H4A | 119.6 |
| C23—C22—H22A | 121.0 | C3—C4—H4A | 119.6 |
| C24—N2—C26 | 103.31 (10) | C11—C10—C9 | 120.38 (13) |
| C20—C19—C18 | 120.87 (12) | C11—C10—H10A | 119.8 |
| C20—C19—H19A | 119.6 | C9—C10—H10A | 119.8 |
| C18—C19—H19A | 119.6 | C2—C3—C4 | 120.17 (13) |
| C13—C12—C11 | 121.85 (12) | C2—C3—H3A | 119.9 |
| C13—C12—C7 | 119.02 (11) | C4—C3—H3A | 119.9 |
| C11—C12—C7 | 119.10 (12) | O3—N1—O2 | 123.78 (12) |
| C15—C16—N3 | 119.29 (10) | O3—N1—C26 | 118.88 (12) |
| C15—C16—C17 | 127.06 (10) | O2—N1—C26 | 117.34 (11) |
| N3—C16—C17 | 113.45 (10) | C26—C25—N3 | 104.56 (11) |
| C25—C26—N2 | 112.89 (11) | C26—C25—H25A | 127.7 |
| C25—C26—N1 | 125.20 (12) | N3—C25—H25A | 127.7 |
| N2—C26—N1 | 121.91 (11) | N2—C24—N3 | 112.26 (12) |
| C9—C8—C7 | 120.97 (12) | N2—C24—H24A | 123.9 |
| C9—C8—H8A | 119.5 | N3—C24—H24A | 123.9 |
| C7—C8—H8A | 119.5 |
The authors thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant Nos. 2007BB5369 and 2006BB4341) for financial support.
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Chalcones (1,3-diaryl-2-propen-1-ones) are flavonoid and isoflavnoid precursors which are abundant in edible plants and display wide biological activities such as antioxidant, antibacterial, antileishmanial, anticancer, antiangiogenic, anti-infective and anti-inflammatory activities. Chalcone derivatives have received much attention due to their relatively simple structures, and wide variety of biological activities (Detsi et al. 2009). A series of chalcone derivatives containing imidazole ring have been synthesized and crystal structures of some of them have been reported (Lu et al. 2009; Wang et al. 2009). We report here the structure of the title compound (I).
The title compound (I), C26H16FN3O3, shows an organic-clip-shaped motif (Hou et al. 2009). The ringent dihedral angle between the anthryl unit and the fluorophenyl group is 37.80°. The imidazolyl group can be seen as the handle of organic clip, and the dihedral angles between the imidazolyl group and the anthryl unit or the fluorophenyl group are 64.40° and 74.51° respectively. In the solid state, the compound (I) is stabilized by weak intermolecule C—H···O and C—H···F hydrogen bonds generating an infinite two-dimensional network.