(E)-3-(9-Anthr-yl)-1-(4-fluoro-phen-yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one.

In the title compound, C(26)H(16)FN(3)O(3), the dihedral angle between the anthryl and fluoro-phenyl 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 fluoro-phenyl group are 64.4 (1) and 74.5 (1)°, respectively.

Related literature

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

Crystal data

C26H16FN3O3

M = 437.42

Triclinic,

a = 9.3362 (6) Å

b = 10.9587 (6) Å

c = 11.6018 (5) Å

α = 70.371 (5)°

β = 88.062 (4)°

γ = 66.781 (6)°

V = 1020.78 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.49 × 0.41 × 0.30 mm

Data collection

Oxford Diffraction Xcaliber diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.951, T max = 0.970

8826 measured reflections

4374 independent reflections

3193 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.01

4374 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055524/ng2707sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055524/ng2707Isup2.hkl

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

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

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