2-(1H-Benzotriazol-1-yl)-1-(2-fluoro­benzo­yl)ethyl 4-methyl­benzoate

Zeng, W.-L.; Jian, F.-F.

doi:10.1107/S1600536809029481

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2036

doi:10.1107/S1600536809029481

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2-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl 4-methylbenzoate

Wu-Lan Zeng ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: wulanzeng@163.com

(Received 17 June 2009; accepted 24 July 2009; online 29 July 2009)

In the crystal structure of the title compound, C₂₃H₁₈FN₃O₃, intermolecular C—H⋯N hydrogen bonds link the molecules into chains extended along the c axis. The packing is further stabilized by weak C—H⋯O and C—H⋯F interactions. The F atom is disordered over two equally occupied 1- and 5-positions of the benzene ring.

Related literature

For the pharmacological activity of 1H-benzotriazole and its derivatives, see: Chen & Wu (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₁₈FN₃O₃
M_r = 403.40
Monoclinic, C 2/c
a = 20.478 (4) Å
b = 19.570 (4) Å
c = 9.969 (2) Å
β = 107.12 (3)°
V = 3818.0 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.10 × 0.06 × 0.02 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.990, T_max = 0.998
19476 measured reflections
3368 independent reflections
2698 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.177
S = 1.08
3368 reflections
282 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯F1	0.98	2.24	2.938 (5)	127
C9—H9A⋯N2ⁱ	0.97	2.55	3.515 (3)	174
C12—H12⋯O1ⁱⁱ	0.93	2.48	3.118 (4)	126
C22—H22⋯O3ⁱⁱⁱ	0.93	2.48	3.259 (4)	142
C23—H23C⋯F1′^iv	0.96	2.37	3.090 (5)	131
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809029481/at2823sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029481/at2823Isup2.hkl

checkCIF report

Comment top

1H-Benzotriazoles and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

All the bond lengths (Allen et al., 1987) and angles in (I) are within their normal ranges. The dihedral angle between the triazole ring (N1–N3/C10/C15) and the benzene ring (C10–C15) is 2.86 (12)°. The dihedral angles between the triazole ring and the C1–C6 and C17–C22 aromatic rings are 4.78 (13)° and 65.34 (13)°, respectively. The dihedral angle between the C1—C6 and C17–C22 rings is 62.04 (14)°. Molecule (I) is chiral. In the crystal structure, intermolecular C—H···N hydrogen bonds (Table1) link the molecules into chains extended along the c axis. The packing (Fig. 2) is further stabilized by weak C—H···O and C—H···F interactions (Table 1).

Related literature top

For the pharmacological activity of 1H-benzotriazole and its derivatives, see: Chen & Wu (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

Bromine (3.2 g, 0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(2-fluorophenyl)propan-1-one (5.38 g, 0.02 mol) and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 4-methylbenzoic acid (2.72 g, 0.02 mol) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for 6 h. The solution was then filtered and concentrated. Single crystals of (I) were obtained by slow evaporation of an acetone-ethylacetate (3:1 v/v) solution at room temperature over a period of one week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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), drawn with 30% probability ellipsoids.

2-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl 4-methylbenzoate top

Crystal data top

C₂₃H₁₈FN₃O₃	F(000) = 1680
M_r = 403.40	D_x = 1.404 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3992 reflections
a = 20.478 (4) Å	θ = 2.1–25.0°
b = 19.570 (4) Å	µ = 0.10 mm⁻¹
c = 9.969 (2) Å	T = 293 K
β = 107.12 (3)°	Block, colourless
V = 3818.0 (13) Å³	0.10 × 0.06 × 0.02 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3368 independent reflections
Radiation source: fine-focus sealed tube	2698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −24→24
T_min = 0.990, T_max = 0.998	k = −23→23
19476 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.177	w = 1/[σ²(F_o²) + (0.0959P)² + 1.3136P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.031
3368 reflections	Δρ_max = 0.38 e Å⁻³
282 parameters	Δρ_min = −0.27 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (6)

Crystal data top

C₂₃H₁₈FN₃O₃	V = 3818.0 (13) Å³
M_r = 403.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.478 (4) Å	µ = 0.10 mm⁻¹
b = 19.570 (4) Å	T = 293 K
c = 9.969 (2) Å	0.10 × 0.06 × 0.02 mm
β = 107.12 (3)°

Data collection top

Bruker SMART CCD diffractometer	3368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2698 reflections with I > 2σ(I)
T_min = 0.990, T_max = 0.998	R_int = 0.058
19476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	2 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.08	Δρ_max = 0.38 e Å⁻³
3368 reflections	Δρ_min = −0.27 e Å⁻³
282 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	Occ. (<1)
F1	0.46661 (19)	0.21126 (19)	0.3054 (4)	0.0709 (10)	0.50
F1'	0.24580 (17)	0.2535 (2)	0.3171 (4)	0.0717 (12)	0.50
O1	0.29447 (10)	0.12509 (10)	0.30001 (18)	0.0462 (5)
O2	0.35449 (9)	0.05690 (8)	0.13268 (16)	0.0371 (5)
O3	0.43939 (11)	0.06667 (10)	0.3332 (2)	0.0622 (7)
N1	0.23322 (11)	0.12861 (10)	−0.02778 (19)	0.0326 (5)
N2	0.19010 (12)	0.17037 (10)	0.0132 (2)	0.0378 (5)
N3	0.13058 (12)	0.14092 (11)	−0.0135 (2)	0.0401 (6)
C1	0.41929 (16)	0.25100 (14)	0.3243 (3)	0.0452 (7)
H1A	0.4518	0.2210	0.3024	0.054*	0.50
C2	0.44099 (19)	0.31500 (17)	0.3776 (3)	0.0602 (9)
H2	0.4862	0.3286	0.3936	0.072*
C3	0.3935 (2)	0.35812 (16)	0.4063 (3)	0.0649 (10)
H3	0.4064	0.4018	0.4405	0.078*
C4	0.3281 (2)	0.33705 (15)	0.3850 (3)	0.0603 (9)
H4	0.2964	0.3662	0.4053	0.072*
C5	0.30868 (16)	0.27283 (14)	0.3337 (3)	0.0487 (8)
H5A	0.2624	0.2585	0.3204	0.058*	0.50
C6	0.35371 (14)	0.22830 (13)	0.3012 (2)	0.0367 (6)
C7	0.33146 (13)	0.15790 (13)	0.2505 (2)	0.0349 (6)
C8	0.35328 (14)	0.12962 (12)	0.1289 (2)	0.0358 (6)
H8	0.3989	0.1469	0.1339	0.043*
C9	0.30282 (13)	0.15017 (12)	−0.0110 (2)	0.0365 (6)
H9A	0.3036	0.1995	−0.0199	0.044*
H9B	0.3178	0.1307	−0.0864	0.044*
C10	0.20015 (13)	0.07007 (12)	−0.0843 (2)	0.0312 (6)
C11	0.21918 (14)	0.01290 (12)	−0.1472 (2)	0.0361 (6)
H11	0.2632	0.0075	−0.1538	0.043*
C12	0.16911 (14)	−0.03490 (13)	−0.1989 (3)	0.0397 (7)
H12	0.1795	−0.0740	−0.2417	0.048*
C13	0.10262 (14)	−0.02655 (14)	−0.1889 (3)	0.0435 (7)
H13	0.0701	−0.0600	−0.2261	0.052*
C14	0.08430 (14)	0.02928 (14)	−0.1262 (3)	0.0418 (7)
H14	0.0403	0.0342	−0.1187	0.050*
C15	0.13458 (13)	0.07866 (12)	−0.0740 (2)	0.0341 (6)
C16	0.40188 (14)	0.03020 (14)	0.2459 (3)	0.0439 (7)
C17	0.40226 (13)	−0.04463 (13)	0.2469 (2)	0.0382 (6)
C18	0.36063 (14)	−0.08304 (13)	0.1382 (3)	0.0391 (6)
H18	0.3305	−0.0613	0.0618	0.047*
C19	0.36382 (15)	−0.15284 (13)	0.1430 (3)	0.0397 (6)
H19	0.3358	−0.1781	0.0692	0.048*
C20	0.40830 (14)	−0.18695 (14)	0.2562 (3)	0.0418 (7)
C21	0.44946 (15)	−0.14802 (15)	0.3646 (3)	0.0448 (7)
H21	0.4795	−0.1697	0.4412	0.054*
C22	0.44658 (14)	−0.07813 (14)	0.3607 (3)	0.0449 (7)
H22	0.4745	−0.0529	0.4346	0.054*
C23	0.41090 (17)	−0.26339 (14)	0.2594 (3)	0.0553 (8)
H23A	0.4499	−0.2781	0.3338	0.083*
H23B	0.4145	−0.2801	0.1714	0.083*
H23C	0.3700	−0.2809	0.2751	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.056 (2)	0.074 (2)	0.086 (3)	−0.018 (2)	0.027 (2)	−0.013 (2)
F1'	0.034 (2)	0.099 (3)	0.070 (2)	0.0195 (19)	−0.0037 (17)	−0.037 (2)
O1	0.0466 (12)	0.0547 (12)	0.0385 (10)	−0.0151 (9)	0.0143 (9)	−0.0042 (9)
O2	0.0374 (10)	0.0336 (9)	0.0341 (9)	0.0032 (8)	0.0012 (8)	−0.0012 (7)
O3	0.0624 (15)	0.0522 (12)	0.0512 (13)	0.0025 (11)	−0.0156 (11)	−0.0096 (10)
N1	0.0364 (12)	0.0303 (11)	0.0287 (11)	0.0038 (9)	0.0059 (9)	0.0007 (8)
N2	0.0453 (14)	0.0351 (11)	0.0301 (11)	0.0105 (10)	0.0065 (10)	−0.0004 (9)
N3	0.0426 (14)	0.0419 (13)	0.0333 (12)	0.0087 (10)	0.0069 (10)	−0.0014 (9)
C1	0.0571 (19)	0.0436 (16)	0.0391 (15)	−0.0061 (14)	0.0209 (14)	0.0011 (12)
C2	0.078 (2)	0.060 (2)	0.0430 (17)	−0.0303 (18)	0.0181 (16)	0.0019 (14)
C3	0.113 (3)	0.0395 (17)	0.0376 (17)	−0.0130 (19)	0.0156 (19)	0.0022 (13)
C4	0.089 (3)	0.0447 (17)	0.0426 (17)	0.0191 (18)	0.0129 (17)	−0.0022 (14)
C5	0.057 (2)	0.0470 (17)	0.0339 (14)	0.0092 (14)	0.0009 (13)	−0.0034 (12)
C6	0.0462 (17)	0.0371 (14)	0.0244 (12)	−0.0004 (12)	0.0069 (11)	0.0021 (10)
C7	0.0308 (14)	0.0422 (14)	0.0285 (12)	−0.0025 (11)	0.0039 (11)	0.0057 (11)
C8	0.0369 (15)	0.0328 (13)	0.0361 (14)	−0.0027 (11)	0.0082 (12)	−0.0007 (11)
C9	0.0429 (16)	0.0329 (13)	0.0321 (13)	−0.0008 (11)	0.0082 (12)	0.0018 (10)
C10	0.0348 (14)	0.0309 (13)	0.0245 (12)	0.0034 (10)	0.0034 (10)	0.0022 (10)
C11	0.0377 (15)	0.0378 (14)	0.0314 (13)	0.0071 (11)	0.0079 (11)	−0.0006 (11)
C12	0.0440 (17)	0.0340 (14)	0.0365 (14)	0.0032 (11)	0.0046 (12)	−0.0061 (11)
C13	0.0387 (16)	0.0416 (15)	0.0413 (15)	−0.0038 (12)	−0.0020 (12)	−0.0023 (12)
C14	0.0334 (15)	0.0512 (17)	0.0378 (14)	0.0042 (12)	0.0058 (12)	0.0023 (12)
C15	0.0370 (15)	0.0344 (13)	0.0268 (12)	0.0075 (11)	0.0029 (11)	0.0016 (10)
C16	0.0405 (16)	0.0475 (16)	0.0356 (15)	0.0056 (13)	−0.0012 (13)	−0.0016 (12)
C17	0.0388 (15)	0.0419 (15)	0.0310 (13)	0.0085 (12)	0.0058 (11)	−0.0004 (11)
C18	0.0425 (16)	0.0430 (15)	0.0285 (13)	0.0082 (12)	0.0055 (12)	0.0028 (11)
C19	0.0514 (17)	0.0407 (15)	0.0268 (13)	0.0093 (12)	0.0110 (12)	−0.0001 (11)
C20	0.0509 (18)	0.0456 (16)	0.0364 (14)	0.0138 (13)	0.0244 (13)	0.0071 (12)
C21	0.0438 (17)	0.0564 (18)	0.0339 (14)	0.0192 (14)	0.0109 (13)	0.0098 (13)
C22	0.0388 (16)	0.0559 (18)	0.0347 (14)	0.0100 (13)	0.0025 (12)	0.0005 (12)
C23	0.072 (2)	0.0493 (17)	0.0518 (17)	0.0197 (15)	0.0292 (16)	0.0130 (14)

Geometric parameters (Å, º) top

F1—C1	1.298 (4)	C9—H9A	0.9700
F1—H1A	0.3515	C9—H9B	0.9700
F1'—C5	1.305 (4)	C10—C15	1.387 (3)
F1'—H5A	0.3449	C10—C11	1.393 (3)
O1—C7	1.204 (3)	C11—C12	1.371 (4)
O2—C16	1.358 (3)	C11—H11	0.9300
O2—C8	1.424 (3)	C12—C13	1.403 (4)
O3—C16	1.209 (3)	C12—H12	0.9300
N1—N2	1.352 (3)	C13—C14	1.365 (4)
N1—C10	1.365 (3)	C13—H13	0.9300
N1—C9	1.448 (3)	C14—C15	1.396 (4)
N2—N3	1.303 (3)	C14—H14	0.9300
N3—C15	1.373 (3)	C16—C17	1.465 (4)
C1—C6	1.368 (4)	C17—C18	1.387 (4)
C1—C2	1.382 (4)	C17—C22	1.390 (4)
C1—H1A	0.9599	C18—C19	1.368 (3)
C2—C3	1.379 (5)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.394 (4)
C3—C4	1.357 (5)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.386 (4)
C4—C5	1.371 (4)	C20—C23	1.497 (4)
C4—H4	0.9300	C21—C22	1.369 (4)
C5—C6	1.375 (4)	C21—H21	0.9300
C5—H5A	0.9601	C22—H22	0.9300
C6—C7	1.492 (4)	C23—H23A	0.9600
C7—C8	1.515 (3)	C23—H23B	0.9600
C8—C9	1.525 (3)	C23—H23C	0.9600
C8—H8	0.9800

C1—F1—H1A	13.4	H9A—C9—H9B	107.6
C5—F1'—H5A	1.9	N1—C10—C15	104.0 (2)
C16—O2—C8	114.16 (19)	N1—C10—C11	133.5 (2)
N2—N1—C10	110.1 (2)	C15—C10—C11	122.4 (2)
N2—N1—C9	119.8 (2)	C12—C11—C10	116.1 (2)
C10—N1—C9	130.1 (2)	C12—C11—H11	122.0
N3—N2—N1	109.03 (19)	C10—C11—H11	122.0
N2—N3—C15	108.0 (2)	C11—C12—C13	121.9 (2)
F1—C1—C6	121.2 (3)	C11—C12—H12	119.1
F1—C1—C2	115.4 (3)	C13—C12—H12	119.1
C6—C1—C2	123.2 (3)	C14—C13—C12	121.9 (3)
F1—C1—H1A	4.9	C14—C13—H13	119.0
C6—C1—H1A	118.4	C12—C13—H13	119.0
C2—C1—H1A	118.4	C13—C14—C15	116.9 (3)
C3—C2—C1	117.9 (3)	C13—C14—H14	121.5
C3—C2—H2	121.1	C15—C14—H14	121.5
C1—C2—H2	121.1	N3—C15—C10	108.9 (2)
C4—C3—C2	120.3 (3)	N3—C15—C14	130.2 (2)
C4—C3—H3	119.8	C10—C15—C14	120.8 (2)
C2—C3—H3	119.8	O3—C16—O2	121.2 (2)
C3—C4—C5	120.1 (3)	O3—C16—C17	125.7 (2)
C3—C4—H4	119.9	O2—C16—C17	113.1 (2)
C5—C4—H4	119.9	C18—C17—C22	119.0 (2)
F1'—C5—C4	118.7 (3)	C18—C17—C16	122.4 (2)
F1'—C5—C6	119.5 (3)	C22—C17—C16	118.6 (2)
C4—C5—C6	121.8 (3)	C19—C18—C17	120.1 (2)
F1'—C5—H5A	0.7	C19—C18—H18	119.9
C4—C5—H5A	119.1	C17—C18—H18	119.9
C6—C5—H5A	119.1	C18—C19—C20	121.3 (2)
C1—C6—C5	116.6 (3)	C18—C19—H19	119.3
C1—C6—C7	122.9 (2)	C20—C19—H19	119.4
C5—C6—C7	120.4 (3)	C21—C20—C19	118.0 (2)
O1—C7—C6	121.3 (2)	C21—C20—C23	121.5 (3)
O1—C7—C8	120.2 (2)	C19—C20—C23	120.4 (3)
C6—C7—C8	118.4 (2)	C22—C21—C20	121.0 (2)
O2—C8—C7	110.6 (2)	C22—C21—H21	119.5
O2—C8—C9	106.83 (19)	C20—C21—H21	119.5
C7—C8—C9	110.8 (2)	C21—C22—C17	120.4 (3)
O2—C8—H8	109.5	C21—C22—H22	119.8
C7—C8—H8	109.5	C17—C22—H22	119.8
C9—C8—H8	109.5	C20—C23—H23A	109.5
N1—C9—C8	114.0 (2)	C20—C23—H23B	109.5
N1—C9—H9A	108.7	H23A—C23—H23B	109.5
C8—C9—H9A	108.7	C20—C23—H23C	109.5
N1—C9—H9B	108.7	H23A—C23—H23C	109.5
C8—C9—H9B	108.7	H23B—C23—H23C	109.5

C10—N1—N2—N3	0.5 (2)	C9—N1—C10—C15	−178.9 (2)
C9—N1—N2—N3	179.16 (19)	N2—N1—C10—C11	176.5 (2)
N1—N2—N3—C15	−0.3 (2)	C9—N1—C10—C11	−2.0 (4)
F1—C1—C2—C3	−176.8 (3)	N1—C10—C11—C12	−176.5 (2)
C6—C1—C2—C3	−1.2 (4)	C15—C10—C11—C12	−0.1 (3)
C1—C2—C3—C4	1.3 (4)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—C5	−0.5 (4)	C11—C12—C13—C14	−0.6 (4)
C3—C4—C5—F1'	178.6 (3)	C12—C13—C14—C15	1.0 (4)
C3—C4—C5—C6	−0.6 (4)	N2—N3—C15—C10	0.0 (3)
F1—C1—C6—C5	175.6 (3)	N2—N3—C15—C14	−177.3 (2)
C2—C1—C6—C5	0.1 (4)	N1—C10—C15—N3	0.2 (2)
F1—C1—C6—C7	−1.4 (4)	C11—C10—C15—N3	−177.1 (2)
C2—C1—C6—C7	−176.8 (2)	N1—C10—C15—C14	177.9 (2)
F1'—C5—C6—C1	−178.4 (3)	C11—C10—C15—C14	0.5 (4)
C4—C5—C6—C1	0.8 (4)	C13—C14—C15—N3	176.1 (2)
F1'—C5—C6—C7	−1.4 (4)	C13—C14—C15—C10	−1.0 (4)
C4—C5—C6—C7	177.8 (2)	C8—O2—C16—O3	−0.7 (4)
C1—C6—C7—O1	137.2 (3)	C8—O2—C16—C17	−179.7 (2)
C5—C6—C7—O1	−39.6 (4)	O3—C16—C17—C18	−175.6 (3)
C1—C6—C7—C8	−46.1 (3)	O2—C16—C17—C18	3.4 (4)
C5—C6—C7—C8	137.1 (2)	O3—C16—C17—C22	3.7 (4)
C16—O2—C8—C7	−65.0 (3)	O2—C16—C17—C22	−177.3 (2)
C16—O2—C8—C9	174.4 (2)	C22—C17—C18—C19	−0.5 (4)
O1—C7—C8—O2	−28.4 (3)	C16—C17—C18—C19	178.8 (2)
C6—C7—C8—O2	154.9 (2)	C17—C18—C19—C20	0.2 (4)
O1—C7—C8—C9	89.9 (3)	C18—C19—C20—C21	0.0 (4)
C6—C7—C8—C9	−86.8 (3)	C18—C19—C20—C23	179.9 (3)
N2—N1—C9—C8	90.5 (3)	C19—C20—C21—C22	0.0 (4)
C10—N1—C9—C8	−91.1 (3)	C23—C20—C21—C22	−179.9 (3)
O2—C8—C9—N1	63.0 (3)	C20—C21—C22—C17	−0.3 (4)
C7—C8—C9—N1	−57.5 (3)	C18—C17—C22—C21	0.5 (4)
N2—N1—C10—C15	−0.4 (2)	C16—C17—C22—C21	−178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F1	0.98	2.24	2.938 (5)	127
C9—H9A···N2ⁱ	0.97	2.55	3.515 (3)	174
C12—H12···O1ⁱⁱ	0.93	2.48	3.118 (4)	126
C18—H18···O2	0.93	2.43	2.741 (3)	100
C22—H22···O3ⁱⁱⁱ	0.93	2.48	3.259 (4)	142
C23—H23C···F1′^iv	0.96	2.37	3.090 (5)	131

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, −y, z−1/2; (iii) −x+1, −y, −z+1; (iv) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈FN₃O₃
M_r	403.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	20.478 (4), 19.570 (4), 9.969 (2)
β (°)	107.12 (3)
V (Å³)	3818.0 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.10 × 0.06 × 0.02

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.990, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	19476, 3368, 2698
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.177, 1.08
No. of reflections	3368
No. of parameters	282
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F1	0.9800	2.2400	2.938 (5)	127.00
C9—H9A···N2ⁱ	0.9700	2.5500	3.515 (3)	174.00
C12—H12···O1ⁱⁱ	0.9300	2.4800	3.118 (4)	126.00
C18—H18···O2	0.9300	2.4300	2.741 (3)	100.00
C22—H22···O3ⁱⁱⁱ	0.9300	2.4800	3.259 (4)	142.00
C23—H23C···F1'^iv	0.9600	2.3700	3.090 (5)	131.00

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, −y, z−1/2; (iii) −x+1, −y, −z+1; (iv) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This research has been supported by the Foundation of Weifang University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1997). SADABS, SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar