(E)-3-(9-Anthr­yl)-1-(4-fluoro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Wang, G.-Z.; Su, M.; Zhou, C.-H.

doi:10.1107/S1600536809039178

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2598

https://doi.org/10.1107/S1600536809039178

Open

access

(E)-3-(9-Anthryl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Guang-Zhou Wang,^a Min Su ^b and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, and ^bCollege of Pharmacy, The Third Military Medical University, Chongqing 400038, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 26 September 2009; accepted 26 September 2009; online 3 October 2009)

The C=C double-bond in the title compound, C₂₅H₁₆FN₃O, has an E configuration. The dihedral angle between the fluorophenyl 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_r = 393.41
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.152
S = 1.14
4187 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039178/ng2652sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039178/ng2652Isup2.hkl

checkCIF report

Comment top

Chalcones have been investigated for a long time due to important biological activities. We have already synthesized and reported several related structures of chalcones (Lu et al., 2009; Wang et al., 2009; Yan et al., 2009). Azole compounds including imidazole and triazole derivatives are important types of antimicrobial drugs in clinical use, and are excellent ligands with several N-atoms which could coordinate with many kinds of metals (Luo et al., 2009; Zhou et al., 2009). The anthracene moiety is well known for its high absorption co-efficient as well as high fluorescence yields. These interesting properties lead us to develop the title anthryl-triazole chalcone derivatives containing the pharmacophore (triazole) and fluorophore (anthracene), and these compounds exhibit good antimicrobial, antitumor and fluorescent properties. Here we present the title compound (I) crystal structure.

The structure of title compound, C₂₅H₁₆FN₃O, has orthorhombic (Pbca) symmetry. It is of interest with respect to biological activity. In the structure, the dihedral angle between the benzene and triazole ring is 80.57 (2)°. Weak intermolecular C—H···O and C—H···N interactions contribute to the crystal packing.

Related literature top

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 top

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985) and Kranz et al. (1980). Single crystals used in X-ray diffraction studies were grown in dichlormethane by slow evaporation at room temperature.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

(E)-3-(9-Anthryl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1- yl)prop-2-en-1-one top

Crystal data top

C₂₅H₁₆FN₃O	F(000) = 1632
M_r = 393.41	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0581P)² + 1.3538P] where P = (F_o² + 2F_c²)/3
4187 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₅H₁₆FN₃O	V = 3833.9 (4) Å³
M_r = 393.41	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.1115 (8) Å	µ = 0.09 mm⁻¹
b = 13.4737 (8) Å	T = 298 K
c = 21.7019 (14) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART diffractometer	4187 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3550 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.991	R_int = 0.041
16309 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.14	Δρ_max = 0.24 e Å⁻³
4187 reflections	Δρ_min = −0.19 e Å⁻³
271 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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₆FN₃O
M_r	393.41
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.1115 (8), 13.4737 (8), 21.7019 (14)
V (Å³)	3833.9 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	16309, 4187, 3550
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.152, 1.14
No. of reflections	4187
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank Southwest University (SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (2007BB5369) for financial support.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Erhardt, H., Mildenberger, H., Handte, R., Sachse, B., Hartz, P. & Bürstell, H. (1985). German Patent No. DE3406908. Google Scholar
Kranz, E., Krämer, W., Büchel, K.-H., Brandes, W. & Forhberger, P.-E. (1980). German Patent No. DE2832233. Google Scholar
Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luo, Y., Lu, Y.-H., Gan, L.-L., Zhou, C.-H., Wu, J., Geng, R.-X. & Zhang, Y.-Y. (2009). Arch. Pharm. Chem. Life Sci. 342, 386–393. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yan, C.-Y., Wang, G.-Z. & Zhou, C.-H. (2009). Acta Cryst. E65, o2054. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhou, C.-H., Gan, L.-L., Zhang, Y.-Y., Zhang, F.-F., Wang, G.-Z., Jin, L. & Geng, R.-X. (2009). Sci. China Ser. Chem. 52, 415–458. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.