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Acta Cryst. (2010). E66, o320
https://doi.org/10.1107/S1600536809055524
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(E)-3-(9-Anthr­yl)-1-(4-fluoro­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

X.-L. Wang, G.-Z. Wang, R.-X. Geng and C.-H. Zhou
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.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809055524/ng2707sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809055524/ng2707Isup2.hkl
Contains datablock I

CCDC reference: 765105

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.090
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT152_ALERT_1_C The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         81


Alert level G
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C13           1.41 Ang.


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

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.

Related literature top

For general background to chalcone derivatives, see: Detsi et al. (2009). For the synthesis, see: Erhardt et al. (1985); Kranz et al. (1980). For related structures, see: Lu et al. (2009); Wang et al. (2009). For a comment on the molecular shape, see: Hou et al. (2009).

Experimental top

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.

Refinement top

Hydrogen atoms were placed in calculated positions with C—H = 0.95Å (aromatic ring) with Uiso(H) = 1.2Ueq(C).

Structure description top

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.

For general background to chalcone derivatives, see: Detsi et al. (2009). For the synthesis, see: Erhardt et al. (1985); Kranz et al. (1980). For related structures, see: Lu et al. (2009); Wang et al. (2009). For a comment on the molecular shape, see: Hou et al. (2009).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing theatom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the CrystalStructure of (I), showing the formation of the three-dimensional network.
(E)-3-(9-Anthryl)-1-(4-fluorophenyl)-2-(4-nitro-1H-imidazol- 1-yl)prop-2-en-1-one top
Crystal data top
C26H16FN3O3Z = 2
Mr = 437.42F(000) = 452
Triclinic, P1Dx = 1.423 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3362 (6) ÅCell parameters from 8826 reflections
b = 10.9587 (6) Åθ = 2.8–27.0°
c = 11.6018 (5) ŵ = 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
Data collection top
Oxford Diffraction Xcaliber
diffractometer		4374 independent reflections
Radiation source: fine-focus sealed tube3193 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 0.01 pixels mm-1θmax = 27.0°, θmin = 2.8°
ω scansh = −11→11
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		k = −13→12
Tmin = 0.951, Tmax = 0.970l = −14→14
8826 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-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 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C26H16FN3O3γ = 66.781 (6)°
Mr = 437.42V = 1020.78 (10) Å3
Triclinic, P1Z = 2
a = 9.3362 (6) ÅMo Kα radiation
b = 10.9587 (6) ŵ = 0.10 mm−1
c = 11.6018 (5) ÅT = 173 K
α = 70.371 (5)°0.49 × 0.41 × 0.30 mm
β = 88.062 (4)°
Data collection top
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 = 0.970Rint = 0.020
8826 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.01Δρmax = 0.22 e Å−3
4374 reflectionsΔρmin = −0.19 e Å−3
298 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
xyzUiso*/Ueq
F10.40315 (10)0.15681 (10)1.18206 (7)0.0560 (3)
O10.12744 (13)−0.02448 (11)0.81580 (8)0.0455 (3)
N30.19905 (12)0.08673 (11)0.58002 (8)0.0261 (2)
C150.10394 (14)0.30540 (13)0.61663 (11)0.0282 (3)
H15A0.10640.34810.53090.034*
C170.16584 (14)0.07397 (13)0.79428 (10)0.0275 (3)
C230.33391 (14)0.16396 (13)0.87665 (11)0.0270 (3)
H23A0.36710.19290.79750.032*
C140.04204 (14)0.40033 (13)0.68792 (10)0.0272 (3)
C6−0.08868 (15)0.40198 (13)0.75307 (10)0.0282 (3)
C180.22475 (14)0.10459 (12)0.89378 (10)0.0244 (3)
C70.11980 (15)0.48598 (13)0.69277 (11)0.0291 (3)
C220.39456 (15)0.18126 (13)0.97408 (12)0.0333 (3)
H22A0.47040.22070.96360.040*
N20.18404 (14)0.02358 (13)0.41956 (9)0.0390 (3)
C190.17599 (15)0.06337 (14)1.01033 (10)0.0323 (3)
H19A0.10230.02161.02260.039*
C120.07161 (15)0.56901 (13)0.77072 (11)0.0326 (3)
C160.15658 (14)0.16506 (13)0.66238 (10)0.0255 (3)
C260.32395 (15)−0.05927 (13)0.49025 (10)0.0295 (3)
O20.56329 (12)−0.24366 (12)0.53163 (10)0.0525 (3)
C80.25072 (16)0.48911 (14)0.62676 (12)0.0368 (3)
H8A0.28380.43650.57310.044*
C1−0.13552 (15)0.48673 (14)0.83035 (11)0.0330 (3)
C200.23331 (16)0.08250 (15)1.10757 (11)0.0368 (3)
H20A0.19860.05681.18660.044*
C210.34228 (15)0.13994 (14)1.08624 (11)0.0346 (3)
O30.41958 (15)−0.18717 (12)0.36400 (9)0.0656 (4)
C13−0.05363 (16)0.56575 (14)0.83786 (12)0.0358 (3)
H13A−0.08420.61950.89070.043*
C5−0.17915 (15)0.32560 (14)0.74550 (12)0.0343 (3)
H5A−0.15290.27150.69290.041*
C2−0.26464 (17)0.48480 (16)0.89925 (13)0.0437 (4)
H2A−0.29490.53860.95210.052*
C110.15633 (17)0.64982 (15)0.77975 (12)0.0405 (3)
H11A0.12420.70630.83030.049*
C90.32888 (18)0.56622 (15)0.63942 (13)0.0450 (4)
H9A0.41650.56590.59530.054*
C4−0.30200 (17)0.32892 (16)0.81208 (13)0.0433 (4)
H4A−0.36040.27700.80570.052*
C100.28170 (19)0.64686 (16)0.71722 (13)0.0472 (4)
H10A0.33840.69940.72570.057*
C3−0.34423 (18)0.40905 (17)0.89124 (14)0.0484 (4)
H3A−0.42920.40890.93870.058*
N10.44252 (15)−0.17030 (13)0.45944 (10)0.0389 (3)
C250.33644 (15)−0.02437 (13)0.58946 (11)0.0294 (3)
H25A0.4225−0.06810.65190.035*
C240.11069 (16)0.11104 (15)0.47696 (11)0.0357 (3)
H24A0.00770.18320.45000.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0625 (6)0.0621 (6)0.0440 (5)−0.0166 (5)−0.0174 (4)−0.0276 (5)
O10.0783 (8)0.0471 (6)0.0291 (5)−0.0426 (6)0.0100 (5)−0.0145 (5)
N30.0312 (6)0.0287 (6)0.0189 (5)−0.0111 (5)0.0027 (4)−0.0102 (4)
C150.0326 (7)0.0304 (7)0.0205 (6)−0.0121 (6)0.0030 (5)−0.0088 (5)
C170.0327 (7)0.0276 (7)0.0239 (6)−0.0126 (6)0.0054 (5)−0.0108 (5)
C230.0278 (6)0.0230 (6)0.0263 (6)−0.0074 (5)0.0035 (5)−0.0077 (5)
C140.0313 (7)0.0220 (6)0.0214 (6)−0.0051 (5)−0.0018 (5)−0.0057 (5)
C60.0308 (7)0.0245 (6)0.0234 (6)−0.0056 (6)−0.0015 (5)−0.0075 (5)
C180.0259 (6)0.0228 (6)0.0205 (6)−0.0052 (5)0.0008 (5)−0.0083 (5)
C70.0330 (7)0.0205 (6)0.0246 (6)−0.0057 (6)−0.0036 (5)−0.0026 (5)
C220.0286 (7)0.0277 (7)0.0419 (7)−0.0081 (6)−0.0036 (6)−0.0135 (6)
N20.0484 (7)0.0445 (7)0.0244 (5)−0.0142 (6)0.0014 (5)−0.0177 (5)
C190.0353 (7)0.0393 (8)0.0243 (6)−0.0178 (6)0.0060 (5)−0.0107 (6)
C120.0377 (7)0.0225 (6)0.0302 (6)−0.0066 (6)−0.0049 (6)−0.0065 (5)
C160.0290 (6)0.0291 (7)0.0209 (6)−0.0117 (6)0.0044 (5)−0.0122 (5)
C260.0372 (7)0.0302 (7)0.0245 (6)−0.0151 (6)0.0099 (5)−0.0127 (5)
O20.0431 (6)0.0485 (7)0.0645 (7)−0.0085 (6)0.0074 (6)−0.0305 (6)
C80.0407 (8)0.0285 (7)0.0353 (7)−0.0119 (6)0.0036 (6)−0.0069 (6)
C10.0354 (7)0.0281 (7)0.0298 (6)−0.0055 (6)0.0014 (6)−0.0121 (6)
C200.0419 (8)0.0438 (8)0.0208 (6)−0.0119 (7)0.0033 (6)−0.0131 (6)
C210.0353 (7)0.0334 (7)0.0298 (7)−0.0028 (6)−0.0101 (6)−0.0166 (6)
O30.0953 (9)0.0581 (7)0.0393 (6)−0.0133 (7)0.0112 (6)−0.0341 (6)
C130.0430 (8)0.0282 (7)0.0336 (7)−0.0073 (6)0.0005 (6)−0.0160 (6)
C50.0349 (7)0.0352 (7)0.0345 (7)−0.0116 (6)0.0036 (6)−0.0173 (6)
C20.0483 (9)0.0418 (8)0.0443 (8)−0.0138 (7)0.0155 (7)−0.0254 (7)
C110.0521 (9)0.0298 (7)0.0375 (7)−0.0148 (7)−0.0069 (7)−0.0100 (6)
C90.0450 (9)0.0385 (8)0.0485 (8)−0.0202 (7)0.0043 (7)−0.0077 (7)
C40.0401 (8)0.0457 (9)0.0535 (9)−0.0208 (7)0.0118 (7)−0.0253 (7)
C100.0545 (10)0.0359 (8)0.0505 (9)−0.0245 (8)−0.0082 (8)−0.0058 (7)
C30.0439 (9)0.0539 (10)0.0549 (9)−0.0196 (8)0.0226 (7)−0.0301 (8)
N10.0520 (8)0.0349 (7)0.0357 (6)−0.0196 (6)0.0167 (6)−0.0184 (6)
C250.0311 (7)0.0282 (7)0.0286 (6)−0.0099 (6)0.0008 (5)−0.0120 (6)
C240.0371 (8)0.0422 (8)0.0240 (6)−0.0100 (7)−0.0023 (6)−0.0140 (6)
Geometric parameters (Å, º) top
F1—C211.3626 (13)C12—C111.4288 (18)
O1—C171.2135 (14)C26—C251.3508 (15)
N3—C251.3521 (16)C26—N11.4272 (17)
N3—C241.3641 (15)O2—N11.2312 (15)
N3—C161.4367 (14)C8—C91.3583 (18)
C15—C161.3273 (17)C8—H8A0.9500
C15—C141.4739 (16)C1—C131.3854 (18)
C15—H15A0.9500C1—C21.4270 (19)
C17—C181.4821 (15)C20—C211.3696 (19)
C17—C161.5034 (16)C20—H20A0.9500
C23—C221.3806 (16)O3—N11.2210 (13)
C23—C181.3869 (16)C13—H13A0.9500
C23—H23A0.9500C5—C41.3563 (18)
C14—C71.4095 (17)C5—H5A0.9500
C14—C61.4109 (17)C2—C31.339 (2)
C6—C51.4260 (17)C2—H2A0.9500
C6—C11.4389 (16)C11—C101.351 (2)
C18—C191.3963 (16)C11—H11A0.9500
C7—C81.4262 (18)C9—C101.411 (2)
C7—C121.4319 (17)C9—H9A0.9500
C22—C211.3682 (18)C4—C31.4192 (19)
C22—H22A0.9500C4—H4A0.9500
N2—C241.3082 (16)C10—H10A0.9500
N2—C261.3565 (16)C3—H3A0.9500
C19—C201.3752 (16)C25—H25A0.9500
C19—H19A0.9500C24—H24A0.9500
C12—C131.3885 (18)
C25—N3—C24106.98 (10)C13—C1—C2121.72 (11)
C25—N3—C16126.08 (10)C13—C1—C6119.74 (12)
C24—N3—C16126.93 (11)C2—C1—C6118.54 (12)
C16—C15—C14125.33 (11)C21—C20—C19117.49 (12)
C16—C15—H15A117.3C21—C20—H20A121.3
C14—C15—H15A117.3C19—C20—H20A121.3
O1—C17—C18121.96 (11)F1—C21—C22117.71 (12)
O1—C17—C16118.70 (10)F1—C21—C20118.41 (11)
C18—C17—C16119.33 (10)C22—C21—C20123.89 (11)
C22—C23—C18120.32 (11)C1—C13—C12122.18 (11)
C22—C23—H23A119.8C1—C13—H13A118.9
C18—C23—H23A119.8C12—C13—H13A118.9
C7—C14—C6120.79 (10)C4—C5—C6121.13 (12)
C7—C14—C15118.37 (11)C4—C5—H5A119.4
C6—C14—C15120.80 (11)C6—C5—H5A119.4
C14—C6—C5123.66 (11)C3—C2—C1121.60 (12)
C14—C6—C1118.58 (11)C3—C2—H2A119.2
C5—C6—C1117.76 (11)C1—C2—H2A119.2
C23—C18—C19119.36 (11)C10—C11—C12120.76 (13)
C23—C18—C17122.07 (10)C10—C11—H11A119.6
C19—C18—C17118.43 (11)C12—C11—H11A119.6
C14—C7—C8122.54 (11)C8—C9—C10120.93 (14)
C14—C7—C12119.57 (11)C8—C9—H9A119.5
C8—C7—C12117.84 (11)C10—C9—H9A119.5
C21—C22—C23118.05 (12)C5—C4—C3120.74 (13)
C21—C22—H22A121.0C5—C4—H4A119.6
C23—C22—H22A121.0C3—C4—H4A119.6
C24—N2—C26103.31 (10)C11—C10—C9120.38 (13)
C20—C19—C18120.87 (12)C11—C10—H10A119.8
C20—C19—H19A119.6C9—C10—H10A119.8
C18—C19—H19A119.6C2—C3—C4120.17 (13)
C13—C12—C11121.85 (12)C2—C3—H3A119.9
C13—C12—C7119.02 (11)C4—C3—H3A119.9
C11—C12—C7119.10 (12)O3—N1—O2123.78 (12)
C15—C16—N3119.29 (10)O3—N1—C26118.88 (12)
C15—C16—C17127.06 (10)O2—N1—C26117.34 (11)
N3—C16—C17113.45 (10)C26—C25—N3104.56 (11)
C25—C26—N2112.89 (11)C26—C25—H25A127.7
C25—C26—N1125.20 (12)N3—C25—H25A127.7
N2—C26—N1121.91 (11)N2—C24—N3112.26 (12)
C9—C8—C7120.97 (12)N2—C24—H24A123.9
C9—C8—H8A119.5N3—C24—H24A123.9
C7—C8—H8A119.5

Experimental details

Crystal data
Chemical formulaC26H16FN3O3
Mr437.42
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.3362 (6), 10.9587 (6), 11.6018 (5)
α, β, γ (°)70.371 (5), 88.062 (4), 66.781 (6)
V (Å3)1020.78 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.49 × 0.41 × 0.30
Data collection
DiffractometerOxford Diffraction Xcaliber
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.951, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections		8826, 4374, 3193
Rint0.020
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.090, 1.01
No. of reflections4374
No. of parameters298
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

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