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

The C=C double-bond in the title compound, C(25)H(16)FN(3)O, has an E configuration. The dihedral angle between the fluoro-phenyl and triazole rings is 80.57 (2)°.

Related literature

For the synthesis, see: Erhardt et al. (1985 ▶); Kranz et al. (1980 ▶). For the pharmacological activity of azoles including imidazole and triazole derivatives, see: Luo et al. (2009 ▶); Zhou et al. (2009 ▶). For related structures, see: Lu et al. (2009 ▶); Wang et al. (2009 ▶); Yan et al. (2009 ▶).

Experimental

Crystal data

C25H16FN3O

M = 393.41

Orthorhombic,

a = 13.1115 (8) Å

b = 13.4737 (8) Å

c = 21.7019 (14) Å

V = 3833.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.991

16309 measured reflections

4187 independent reflections

3550 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.152

S = 1.14

4187 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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/S1600536809039178/ng2652sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039178/ng2652Isup2.hkl

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

C25H16FN3O	F(000) = 1632
Mr = 393.41	Dx = 1.363 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5206 reflections
a = 13.1115 (8) Å	θ = 2.4–27.6°
b = 13.4737 (8) Å	µ = 0.09 mm−1
c = 21.7019 (14) Å	T = 298 K
V = 3833.9 (4) Å3	Block, yellow
Z = 8	0.20 × 0.10 × 0.10 mm

Bruker SMART diffractometer	4187 independent reflections
Radiation source: fine-focus sealed tube	3550 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→6
Tmin = 0.982, Tmax = 0.991	k = −12→17
16309 measured reflections	l = −27→26

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0581P)2 + 1.3538P] where P = (Fo2 + 2Fc2)/3
4187 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.24 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
C1	0.33997 (13)	−0.03462 (14)	0.19230 (8)	0.0395 (4)
C2	0.28391 (14)	−0.00708 (17)	0.14089 (9)	0.0471 (5)
H2	0.2586	0.0572	0.1377	0.057*
C3	0.26557 (17)	−0.0751 (2)	0.09435 (10)	0.0613 (6)
H3	0.2296	−0.0569	0.0592	0.074*
C4	0.30156 (18)	−0.1692 (2)	0.10137 (12)	0.0676 (7)
C5	0.35496 (19)	−0.19944 (19)	0.15162 (13)	0.0710 (7)
H5	0.3771	−0.2648	0.1551	0.085*
C6	0.37565 (16)	−0.13104 (16)	0.19739 (11)	0.0544 (5)
H6	0.4136	−0.1498	0.2317	0.065*
C7	0.35581 (14)	0.03737 (14)	0.24300 (8)	0.0385 (4)
C8	0.45641 (13)	0.03523 (13)	0.27672 (8)	0.0360 (4)
C9	0.37480 (17)	0.02786 (19)	0.38130 (9)	0.0587 (6)
H9	0.3100	0.0069	0.3697	0.070*
C10	0.50043 (18)	0.07070 (17)	0.43119 (9)	0.0542 (5)
H10	0.5415	0.0867	0.4647	0.065*
C11	0.54642 (14)	0.03428 (14)	0.24860 (8)	0.0394 (4)
H11	0.6044	0.0310	0.2732	0.047*
C12	0.56121 (13)	0.03800 (14)	0.18104 (8)	0.0376 (4)
C13	0.53007 (13)	0.12230 (14)	0.14735 (8)	0.0392 (4)
C14	0.48685 (16)	0.20863 (15)	0.17516 (9)	0.0475 (5)
H14	0.4783	0.2104	0.2177	0.057*
C15	0.45807 (18)	0.28783 (18)	0.14105 (11)	0.0589 (6)
H15	0.4301	0.3430	0.1605	0.071*
C16	0.46980 (19)	0.28793 (19)	0.07665 (11)	0.0634 (6)
H16	0.4485	0.3424	0.0537	0.076*
C17	0.51180 (17)	0.20924 (18)	0.04815 (10)	0.0576 (6)
H17	0.5198	0.2105	0.0056	0.069*
C18	0.54443 (14)	0.12368 (16)	0.08176 (8)	0.0437 (5)
C19	0.58943 (16)	0.04302 (16)	0.05307 (9)	0.0488 (5)
H19	0.5968	0.0439	0.0105	0.059*
C20	0.62388 (14)	−0.03901 (15)	0.08563 (9)	0.0437 (5)
C21	0.67370 (18)	−0.12021 (18)	0.05638 (10)	0.0583 (6)
H21	0.6821	−0.1195	0.0138	0.070*
C22	0.7087 (2)	−0.19767 (19)	0.08895 (12)	0.0696 (7)
H22	0.7412	−0.2498	0.0689	0.083*
C23	0.6965 (2)	−0.20059 (18)	0.15352 (12)	0.0667 (7)
H23	0.7214	−0.2545	0.1757	0.080*
C24	0.64870 (17)	−0.12541 (16)	0.18361 (10)	0.0532 (5)
H24	0.6408	−0.1288	0.2261	0.064*
C25	0.61067 (14)	−0.04183 (14)	0.15128 (8)	0.0405 (4)
F1	0.28332 (14)	−0.23601 (15)	0.05633 (9)	0.1089 (7)
N1	0.45059 (11)	0.04595 (11)	0.34187 (7)	0.0386 (4)
N2	0.40276 (16)	0.04324 (16)	0.43811 (8)	0.0624 (5)
N3	0.53431 (13)	0.07357 (14)	0.37481 (7)	0.0507 (4)
O1	0.29069 (10)	0.09647 (12)	0.25734 (7)	0.0580 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0319 (9)	0.0475 (11)	0.0392 (9)	−0.0033 (8)	0.0027 (7)	−0.0032 (8)
C2	0.0384 (10)	0.0588 (12)	0.0442 (11)	−0.0026 (9)	−0.0005 (8)	−0.0006 (9)
C3	0.0460 (11)	0.0943 (19)	0.0437 (11)	−0.0103 (12)	−0.0051 (9)	−0.0090 (12)
C4	0.0497 (12)	0.0877 (19)	0.0653 (15)	−0.0100 (13)	0.0023 (11)	−0.0383 (14)
C5	0.0600 (14)	0.0563 (14)	0.097 (2)	0.0019 (12)	−0.0040 (14)	−0.0270 (14)
C6	0.0499 (12)	0.0502 (12)	0.0632 (13)	0.0028 (10)	−0.0088 (10)	−0.0064 (10)
C7	0.0342 (9)	0.0441 (10)	0.0372 (9)	−0.0024 (8)	0.0023 (7)	−0.0008 (8)
C8	0.0386 (9)	0.0398 (10)	0.0297 (8)	−0.0014 (7)	−0.0009 (7)	−0.0012 (7)
C9	0.0463 (11)	0.0879 (17)	0.0418 (11)	−0.0146 (11)	0.0088 (9)	0.0002 (11)
C10	0.0641 (13)	0.0643 (14)	0.0343 (10)	−0.0054 (11)	−0.0020 (9)	−0.0053 (9)
C11	0.0350 (9)	0.0499 (11)	0.0334 (9)	−0.0006 (8)	−0.0030 (7)	0.0003 (8)
C12	0.0307 (8)	0.0506 (11)	0.0315 (9)	−0.0065 (8)	0.0011 (7)	−0.0026 (8)
C13	0.0324 (8)	0.0494 (11)	0.0358 (9)	−0.0089 (8)	−0.0008 (7)	−0.0002 (8)
C14	0.0499 (11)	0.0516 (12)	0.0411 (10)	−0.0046 (9)	0.0025 (9)	−0.0013 (9)
C15	0.0624 (14)	0.0503 (13)	0.0641 (14)	0.0032 (10)	0.0060 (11)	0.0028 (11)
C16	0.0622 (14)	0.0642 (15)	0.0637 (14)	0.0088 (12)	0.0056 (11)	0.0229 (12)
C17	0.0559 (13)	0.0763 (16)	0.0405 (11)	−0.0025 (12)	0.0027 (9)	0.0155 (11)
C18	0.0378 (9)	0.0573 (12)	0.0360 (10)	−0.0068 (9)	0.0002 (8)	0.0032 (9)
C19	0.0485 (11)	0.0691 (14)	0.0288 (9)	−0.0086 (10)	0.0025 (8)	−0.0007 (9)
C20	0.0389 (10)	0.0542 (12)	0.0381 (10)	−0.0091 (8)	0.0022 (8)	−0.0093 (9)
C21	0.0662 (14)	0.0628 (15)	0.0460 (12)	−0.0052 (12)	0.0095 (10)	−0.0147 (11)
C22	0.0804 (17)	0.0574 (15)	0.0710 (16)	0.0056 (13)	0.0183 (13)	−0.0151 (13)
C23	0.0755 (16)	0.0506 (13)	0.0741 (16)	0.0068 (12)	0.0109 (13)	0.0064 (12)
C24	0.0554 (12)	0.0562 (13)	0.0481 (12)	0.0005 (10)	0.0085 (10)	0.0039 (10)
C25	0.0355 (9)	0.0472 (11)	0.0389 (10)	−0.0084 (8)	0.0027 (7)	−0.0014 (8)
F1	0.0917 (12)	0.1308 (15)	0.1043 (13)	−0.0117 (11)	−0.0058 (10)	−0.0780 (12)
N1	0.0392 (8)	0.0445 (9)	0.0321 (8)	−0.0036 (7)	0.0021 (6)	−0.0009 (6)
N2	0.0652 (12)	0.0856 (14)	0.0365 (9)	−0.0080 (11)	0.0098 (8)	0.0014 (9)
N3	0.0491 (9)	0.0681 (12)	0.0350 (8)	−0.0111 (8)	−0.0023 (7)	−0.0072 (8)
O1	0.0419 (8)	0.0665 (10)	0.0657 (10)	0.0116 (7)	−0.0041 (7)	−0.0224 (8)

C1—C6	1.385 (3)	C12—C25	1.412 (3)
C1—C2	1.387 (3)	C13—C14	1.428 (3)
C1—C7	1.481 (3)	C13—C18	1.436 (3)
C2—C3	1.385 (3)	C14—C15	1.352 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.362 (4)	C15—C16	1.406 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—F1	1.350 (3)	C16—C17	1.345 (3)
C4—C5	1.358 (4)	C16—H16	0.9300
C5—C6	1.382 (3)	C17—C18	1.430 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.385 (3)
C7—O1	1.208 (2)	C19—C20	1.387 (3)
C7—C8	1.509 (2)	C19—H19	0.9300
C8—C11	1.329 (2)	C20—C21	1.424 (3)
C8—N1	1.423 (2)	C20—C25	1.436 (3)
C9—N2	1.303 (3)	C21—C22	1.342 (3)
C9—N1	1.334 (2)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.411 (4)
C10—N3	1.302 (3)	C22—H22	0.9300
C10—N2	1.341 (3)	C23—C24	1.358 (3)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.480 (2)	C24—C25	1.417 (3)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.411 (3)	N1—N3	1.362 (2)
C6—C1—C2	119.61 (18)	C15—C14—H14	119.3
C6—C1—C7	120.50 (17)	C13—C14—H14	119.3
C2—C1—C7	119.78 (18)	C14—C15—C16	120.9 (2)
C3—C2—C1	120.1 (2)	C14—C15—H15	119.5
C3—C2—H2	119.9	C16—C15—H15	119.5
C1—C2—H2	119.9	C17—C16—C15	120.1 (2)
C4—C3—C2	118.3 (2)	C17—C16—H16	120.0
C4—C3—H3	120.8	C15—C16—H16	120.0
C2—C3—H3	120.8	C16—C17—C18	121.6 (2)
F1—C4—C5	118.2 (3)	C16—C17—H17	119.2
F1—C4—C3	118.6 (3)	C18—C17—H17	119.2
C5—C4—C3	123.2 (2)	C19—C18—C17	122.07 (18)
C4—C5—C6	118.6 (2)	C19—C18—C13	119.44 (18)
C4—C5—H5	120.7	C17—C18—C13	118.49 (19)
C6—C5—H5	120.7	C18—C19—C20	122.34 (17)
C5—C6—C1	120.1 (2)	C18—C19—H19	118.8
C5—C6—H6	119.9	C20—C19—H19	118.8
C1—C6—H6	119.9	C19—C20—C21	122.31 (19)
O1—C7—C1	121.59 (17)	C19—C20—C25	119.16 (18)
O1—C7—C8	120.36 (17)	C21—C20—C25	118.53 (19)
C1—C7—C8	118.06 (16)	C22—C21—C20	121.3 (2)
C11—C8—N1	120.33 (16)	C22—C21—H21	119.3
C11—C8—C7	123.64 (16)	C20—C21—H21	119.3
N1—C8—C7	115.66 (15)	C21—C22—C23	120.4 (2)
N2—C9—N1	111.61 (19)	C21—C22—H22	119.8
N2—C9—H9	124.2	C23—C22—H22	119.8
N1—C9—H9	124.2	C24—C23—C22	120.6 (2)
N3—C10—N2	116.04 (19)	C24—C23—H23	119.7
N3—C10—H10	122.0	C22—C23—H23	119.7
N2—C10—H10	122.0	C23—C24—C25	121.1 (2)
C8—C11—C12	124.83 (16)	C23—C24—H24	119.4
C8—C11—H11	117.6	C25—C24—H24	119.4
C12—C11—H11	117.6	C12—C25—C24	122.70 (17)
C13—C12—C25	120.59 (16)	C12—C25—C20	119.28 (17)
C13—C12—C11	120.18 (17)	C24—C25—C20	118.02 (18)
C25—C12—C11	119.17 (17)	C9—N1—N3	108.28 (15)
C12—C13—C14	123.48 (17)	C9—N1—C8	131.20 (16)
C12—C13—C18	119.09 (17)	N3—N1—C8	120.40 (14)
C14—C13—C18	117.41 (17)	C9—N2—C10	101.93 (17)
C15—C14—C13	121.49 (19)	C10—N3—N1	102.13 (16)
C6—C1—C2—C3	−1.3 (3)	C14—C13—C18—C19	177.72 (18)
C7—C1—C2—C3	−177.61 (18)	C12—C13—C18—C17	179.52 (17)
C1—C2—C3—C4	1.7 (3)	C14—C13—C18—C17	−2.0 (3)
C2—C3—C4—F1	179.6 (2)	C17—C18—C19—C20	178.12 (19)
C2—C3—C4—C5	−0.3 (4)	C13—C18—C19—C20	−1.6 (3)
F1—C4—C5—C6	178.8 (2)	C18—C19—C20—C21	−177.50 (19)
C3—C4—C5—C6	−1.3 (4)	C18—C19—C20—C25	1.4 (3)
C4—C5—C6—C1	1.6 (4)	C19—C20—C21—C22	178.3 (2)
C2—C1—C6—C5	−0.4 (3)	C25—C20—C21—C22	−0.6 (3)
C7—C1—C6—C5	175.9 (2)	C20—C21—C22—C23	0.2 (4)
C6—C1—C7—O1	−141.0 (2)	C21—C22—C23—C24	0.3 (4)
C2—C1—C7—O1	35.2 (3)	C22—C23—C24—C25	−0.5 (4)
C6—C1—C7—C8	39.1 (2)	C13—C12—C25—C24	176.20 (17)
C2—C1—C7—C8	−144.71 (18)	C11—C12—C25—C24	−1.1 (3)
O1—C7—C8—C11	−131.1 (2)	C13—C12—C25—C20	−3.5 (3)
C1—C7—C8—C11	48.8 (3)	C11—C12—C25—C20	179.16 (16)
O1—C7—C8—N1	41.8 (3)	C23—C24—C25—C12	−179.6 (2)
C1—C7—C8—N1	−138.21 (17)	C23—C24—C25—C20	0.2 (3)
N1—C8—C11—C12	−170.82 (17)	C19—C20—C25—C12	1.2 (3)
C7—C8—C11—C12	1.8 (3)	C21—C20—C25—C12	−179.87 (18)
C8—C11—C12—C13	63.7 (3)	C19—C20—C25—C24	−178.53 (18)
C8—C11—C12—C25	−118.9 (2)	C21—C20—C25—C24	0.4 (3)
C25—C12—C13—C14	−175.05 (17)	N2—C9—N1—N3	1.0 (3)
C11—C12—C13—C14	2.2 (3)	N2—C9—N1—C8	176.88 (19)
C25—C12—C13—C18	3.3 (3)	C11—C8—N1—C9	−163.3 (2)
C11—C12—C13—C18	−179.43 (16)	C7—C8—N1—C9	23.5 (3)
C12—C13—C14—C15	179.98 (19)	C11—C8—N1—N3	12.2 (3)
C18—C13—C14—C15	1.6 (3)	C7—C8—N1—N3	−160.99 (17)
C13—C14—C15—C16	0.0 (3)	N1—C9—N2—C10	−0.7 (3)
C14—C15—C16—C17	−1.2 (4)	N3—C10—N2—C9	0.2 (3)
C15—C16—C17—C18	0.7 (4)	N2—C10—N3—N1	0.4 (3)
C16—C17—C18—C19	−178.8 (2)	C9—N1—N3—C10	−0.8 (2)
C16—C17—C18—C13	0.9 (3)	C8—N1—N3—C10	−177.23 (17)
C12—C13—C18—C19	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O1i	0.93	2.48	3.354 (3)	156
C5—H5···N3i	0.93	2.55	3.434 (3)	158