3-(2,4-Dichloro­phen­yl)-5-(4-fluoro­phen­yl)-2-methyl-7-(trifluoro­meth­yl)pyrazolo­[1,5-a]pyrimidine

Liu, J.; Cai, Z.-Q.; Wang, Y.; Jiang, M.-J.; Xu, L.-F.

doi:10.1107/S1600536812017345

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1515

doi:10.1107/S1600536812017345

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3-(2,4-Dichlorophenyl)-5-(4-fluorophenyl)-2-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

Ju Liu,^a Zhi-Qiang Cai,^b,^c ^* Yang Wang,^a Ming-Jun Jiang ^a and Li-Feng Xu ^a

^aCollege of Pharmacy, Liaoning University, Shenyang 110036, People's Republic of China, ^bPanjin Vocational and Technical College, Panjin 120010, People's Republic of China, and ^cTianjin Key Laboratory of Molecular Design and Drug Discovery, State Key Laboratory of Drug Delivery Technology and Pharmacokinetics, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: caizq@tjipr.com,czq0601@gmail.com

(Received 16 April 2012; accepted 19 April 2012; online 25 April 2012)

In the title compound, C₂₀H₁₁Cl₂F₄N₃, the central pyrazolo[1,5-a]pyrimidine unit is almost planar [the mean deviation from the best least-square plane through the nine atoms is 0.006 (2) Å]. The fluorobenzene ring is rotated out of this plane by 10.3 (3)°, whereas the dichlorobenzene ring is rotated by 46.2 (3)°. The crystal packing is dominated by Cl⋯Cl interactions of 3.475 (3) Å and van der Waals interactions.

Related literature

For the synthesis of other pyrazolo[1,5-a]pyrimidine derivatives and for their pharmacological applications, see: Fraley et al. (2012 ); Novinson et al. (1976 ); Senga et al. (1981 ); Suzuki et al. (2001 ). For related structures, see: Liu et al. (2012 ); Bui et al. (2009 ).

Experimental

Crystal data

C₂₀H₁₁Cl₂F₄N₃
M_r = 440.22
Orthorhombic, P b c a
a = 9.5361 (19) Å
b = 15.941 (3) Å
c = 24.853 (5) Å
V = 3778.0 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.926, T_max = 0.940
34334 measured reflections
4477 independent reflections
3517 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.153
S = 1.08
4477 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2005); 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: 10.1107/S1600536812017345/kp2407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017345/kp2407Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017345/kp2407Isup3.cml

checkCIF report

Comment top

Pyrazolo[1,5-a]pyrimidines are purine analogues with useful properties as antimetabolites in purine biochemical reactions. They are used in a wide array of synthetic and medical chemistry, such as antitrypanosomal and antischistosomal activities, KDR kinase inhibitors, selective peripheral benzodiazepine receptor ligands (Fraley et al., 2012). We have adapted the known method and synthesised the compound. The new molecule is expected to exhibit enhanced biological activity. To characterize our product, its single-crystal structure was determined.

The title molecule (Fig. 1) bond lengths and angles are generally within normal ranges. The dihedral angles formed by the two benzene rings is 50.76 (3) °. The relatively small deviations from the ring planes of the attached substituents are defined by corresponding torsion angles: C(11)—C(18)—C(19)—C(20) of -176.8 (2) for the threefluromethyl group (C20); N(2)—N(3)—C(8)—C(9) of 177.5 (2) for methyl group (C9); C(13)—C(14)—C(15)—F(4) of -179.7 (2) for F4, and Cl(1)—C(3)—C(4)—C(5) of 179.2 (2) for Cl1; Cl(2)—C(5)—C(6)—C(1) of -174.8 (2)°. The crystal structure is held together by van der Waals forces and pronounced Cl···Cl interaction of 3.475()Å (Bui et al., 2009).

Related literature top

For the synthesis of other pyrazolo[1,5-a]pyrimidine derivatives and for their pharmacological applications, see: Fraley et al. (2012); Novinson et al. (1976); Senga et al. (1981); Suzuki et al. (2001). For related structures, see: Liu et al. (2012); Bui et al. (2009).

Experimental top

A mixture of the corresponding 4-(2,4-dichlorophenyl)-3-methyl-1H-pyrazol -5-amine (1.40 g, 5.78 mmol) and the 4,4,4-trifluoro-1-(4-fluorophenyl) butane-1,3-dione (1.49 g, 6.36 mmol) in a flask (25 mL) was heated at 433-438 K for 2.5 h, allowing elimination of the water evolved. After cooling to room temperature, the solid in the flask was recrystallised from methanol to yield the title compound as a yellow solid (1.70 g, 66.78%). Crystals suitable for X-ray analysis were obtained from a mixture of solvents ethanol/acetone(1:1) by slow evaporation.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 structure of C₂₀H₁₁Cl₂F₄N₃ with all non-H atom-labelling scheme and ellipsoids drawn at the 50% probability level.

3-(2,4-Dichlorophenyl)-5-(4-fluorophenyl)-2-methyl-7- (trifluoromethyl)pyrazolo[1,5-a]pyrimidine top

Crystal data top

C₂₀H₁₁Cl₂F₄N₃	F(000) = 1776
M_r = 440.22	D_x = 1.548 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8300 reflections
a = 9.5361 (19) Å	θ = 2.3–27.9°
b = 15.941 (3) Å	µ = 0.39 mm⁻¹
c = 24.853 (5) Å	T = 298 K
V = 3778.0 (13) Å³	Block, yellow
Z = 8	0.20 × 0.18 × 0.16 mm

Data collection top

Rigaku Saturn diffractometer	4477 independent reflections
Radiation source: rotating anode	3517 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.049
ω scans	θ_max = 27.9°, θ_min = 2.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −11→12
T_min = 0.926, T_max = 0.940	k = −20→20
34334 measured reflections	l = −32→32

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0762P)² + 0.9456P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.002
4477 reflections	Δρ_max = 0.27 e Å⁻³
264 parameters	Δρ_min = −0.34 e Å⁻³
0 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: 0.0093 (10)

Crystal data top

C₂₀H₁₁Cl₂F₄N₃	V = 3778.0 (13) Å³
M_r = 440.22	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.5361 (19) Å	µ = 0.39 mm⁻¹
b = 15.941 (3) Å	T = 298 K
c = 24.853 (5) Å	0.20 × 0.18 × 0.16 mm

Data collection top

Rigaku Saturn diffractometer	4477 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3517 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.940	R_int = 0.049
34334 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.08	Δρ_max = 0.27 e Å⁻³
4477 reflections	Δρ_min = −0.34 e Å⁻³
264 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
Cl1	0.65368 (10)	−0.11103 (5)	0.54765 (3)	0.0819 (3)
Cl2	0.61073 (8)	0.22387 (4)	0.56049 (3)	0.0626 (2)
F1	0.25116 (18)	0.44152 (9)	0.75453 (7)	0.0707 (4)
F2	0.06282 (16)	0.37077 (10)	0.75226 (7)	0.0726 (5)
F3	0.1688 (2)	0.39016 (11)	0.82698 (6)	0.0841 (6)
F4	0.6356 (2)	−0.01913 (11)	0.96188 (6)	0.0839 (5)
N1	0.44109 (19)	0.15634 (11)	0.74870 (6)	0.0430 (4)
N2	0.30004 (19)	0.27037 (11)	0.71649 (6)	0.0416 (4)
N3	0.2542 (2)	0.30511 (11)	0.66969 (7)	0.0467 (4)
C1	0.4349 (2)	0.03787 (14)	0.64421 (9)	0.0495 (5)
H1	0.3749	0.0312	0.6734	0.059*
C2	0.4924 (3)	−0.03226 (14)	0.62119 (10)	0.0557 (6)
H2	0.4712	−0.0854	0.6343	0.067*
C3	0.5822 (3)	−0.02252 (15)	0.57820 (9)	0.0540 (6)
C4	0.6166 (3)	0.05579 (15)	0.55899 (9)	0.0534 (6)
H4	0.6785	0.0617	0.5303	0.064*
C5	0.5576 (2)	0.12577 (13)	0.58318 (8)	0.0442 (5)
C6	0.4625 (2)	0.11903 (13)	0.62578 (8)	0.0409 (5)
C7	0.3930 (2)	0.19044 (13)	0.65241 (8)	0.0414 (5)
C8	0.3106 (2)	0.25618 (13)	0.63129 (8)	0.0440 (5)
C9	0.2755 (3)	0.27527 (16)	0.57386 (8)	0.0575 (6)
H9A	0.1841	0.3003	0.5720	0.086*
H9B	0.2763	0.2243	0.5533	0.086*
H9C	0.3437	0.3135	0.5595	0.086*
C10	0.3844 (2)	0.20017 (13)	0.70785 (8)	0.0407 (4)
C11	0.4124 (2)	0.18080 (13)	0.79856 (8)	0.0417 (5)
C12	0.4725 (2)	0.12953 (13)	0.84255 (8)	0.0422 (5)
C13	0.4680 (3)	0.15520 (15)	0.89601 (9)	0.0566 (6)
H13	0.4272	0.2064	0.9048	0.068*
C14	0.5237 (3)	0.10527 (17)	0.93628 (9)	0.0644 (7)
H14	0.5217	0.1227	0.9720	0.077*
C15	0.5813 (3)	0.03045 (15)	0.92273 (9)	0.0557 (6)
C16	0.5893 (3)	0.00274 (14)	0.87055 (10)	0.0562 (6)
H16	0.6305	−0.0486	0.8624	0.067*
C17	0.5345 (3)	0.05311 (14)	0.83055 (9)	0.0499 (5)
H17	0.5392	0.0355	0.7949	0.060*
C18	0.3272 (2)	0.25229 (13)	0.80901 (8)	0.0448 (5)
H18	0.3090	0.2685	0.8443	0.054*
C19	0.2727 (2)	0.29661 (13)	0.76758 (8)	0.0428 (5)
C20	0.1884 (3)	0.37488 (14)	0.77517 (9)	0.0499 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1165 (7)	0.0593 (4)	0.0700 (5)	0.0266 (4)	0.0131 (4)	−0.0112 (3)
Cl2	0.0768 (5)	0.0527 (4)	0.0582 (4)	−0.0109 (3)	0.0173 (3)	0.0097 (3)
F1	0.0777 (10)	0.0447 (8)	0.0896 (11)	0.0045 (7)	0.0037 (8)	0.0058 (7)
F2	0.0491 (9)	0.0751 (10)	0.0938 (12)	0.0153 (7)	−0.0084 (8)	−0.0075 (9)
F3	0.1183 (15)	0.0839 (11)	0.0501 (9)	0.0531 (10)	0.0102 (8)	−0.0051 (7)
F4	0.1151 (14)	0.0751 (11)	0.0615 (9)	0.0177 (10)	−0.0265 (9)	0.0221 (8)
N1	0.0519 (10)	0.0432 (9)	0.0341 (8)	0.0063 (8)	0.0011 (7)	0.0031 (7)
N2	0.0484 (10)	0.0413 (9)	0.0350 (8)	0.0070 (7)	−0.0006 (7)	0.0019 (7)
N3	0.0564 (11)	0.0457 (10)	0.0382 (9)	0.0073 (8)	−0.0067 (8)	0.0046 (7)
C1	0.0567 (14)	0.0476 (12)	0.0442 (11)	−0.0017 (10)	0.0107 (10)	0.0050 (9)
C2	0.0717 (16)	0.0405 (11)	0.0549 (13)	−0.0022 (11)	0.0065 (11)	0.0046 (10)
C3	0.0676 (15)	0.0467 (12)	0.0476 (12)	0.0093 (11)	0.0010 (11)	−0.0059 (10)
C4	0.0631 (15)	0.0569 (14)	0.0403 (11)	0.0036 (11)	0.0107 (10)	−0.0007 (9)
C5	0.0525 (13)	0.0451 (11)	0.0352 (10)	−0.0032 (9)	0.0033 (9)	0.0032 (8)
C6	0.0475 (12)	0.0417 (10)	0.0335 (9)	−0.0014 (9)	−0.0009 (8)	−0.0003 (8)
C7	0.0485 (12)	0.0413 (11)	0.0345 (9)	0.0007 (9)	0.0022 (8)	0.0017 (8)
C8	0.0518 (13)	0.0428 (11)	0.0374 (10)	−0.0006 (9)	−0.0029 (8)	0.0024 (8)
C9	0.0748 (17)	0.0587 (14)	0.0389 (11)	0.0084 (12)	−0.0087 (11)	0.0016 (10)
C10	0.0463 (11)	0.0394 (10)	0.0364 (10)	0.0042 (8)	0.0017 (8)	0.0035 (8)
C11	0.0481 (12)	0.0412 (11)	0.0357 (10)	0.0035 (9)	0.0029 (8)	0.0023 (8)
C12	0.0501 (12)	0.0402 (10)	0.0363 (10)	0.0005 (9)	−0.0005 (8)	0.0034 (8)
C13	0.0766 (17)	0.0541 (13)	0.0392 (11)	0.0139 (12)	0.0002 (11)	0.0021 (10)
C14	0.089 (2)	0.0681 (16)	0.0360 (11)	0.0103 (14)	−0.0060 (12)	0.0032 (10)
C15	0.0661 (15)	0.0544 (13)	0.0465 (12)	0.0013 (11)	−0.0125 (11)	0.0155 (10)
C16	0.0677 (16)	0.0443 (12)	0.0567 (14)	0.0089 (11)	−0.0113 (11)	0.0048 (10)
C17	0.0630 (15)	0.0459 (12)	0.0409 (11)	0.0067 (10)	−0.0064 (10)	0.0000 (9)
C18	0.0529 (13)	0.0452 (11)	0.0362 (10)	0.0071 (9)	0.0056 (9)	0.0022 (8)
C19	0.0463 (12)	0.0432 (11)	0.0388 (10)	0.0033 (9)	0.0033 (8)	0.0009 (8)
C20	0.0559 (14)	0.0485 (12)	0.0453 (12)	0.0114 (10)	0.0021 (10)	0.0000 (9)

Geometric parameters (Å, º) top

Cl1—C3	1.741 (2)	C7—C10	1.389 (3)
Cl2—C5	1.738 (2)	C7—C8	1.411 (3)
F1—C20	1.323 (3)	C8—C9	1.497 (3)
F2—C20	1.328 (3)	C9—H9A	0.9600
F3—C20	1.324 (3)	C9—H9B	0.9600
F4—C15	1.356 (3)	C9—H9C	0.9600
N1—C11	1.327 (2)	C11—C18	1.424 (3)
N1—C10	1.346 (2)	C11—C12	1.480 (3)
N2—N3	1.360 (2)	C12—C17	1.386 (3)
N2—C19	1.362 (2)	C12—C13	1.391 (3)
N2—C10	1.395 (3)	C13—C14	1.385 (3)
N3—C8	1.345 (3)	C13—H13	0.9300
C1—C2	1.370 (3)	C14—C15	1.355 (4)
C1—C6	1.397 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.372 (3)
C2—C3	1.378 (3)	C16—C17	1.381 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.376 (3)	C17—H17	0.9300
C4—C5	1.387 (3)	C18—C19	1.353 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.398 (3)	C19—C20	1.496 (3)
C6—C7	1.474 (3)

C11—N1—C10	117.98 (18)	N1—C10—N2	122.14 (18)
N3—N2—C19	127.64 (17)	C7—C10—N2	106.04 (17)
N3—N2—C10	112.34 (16)	N1—C11—C18	121.53 (18)
C19—N2—C10	120.02 (17)	N1—C11—C12	116.59 (18)
C8—N3—N2	104.03 (16)	C18—C11—C12	121.88 (18)
C2—C1—C6	122.9 (2)	C17—C12—C13	118.5 (2)
C2—C1—H1	118.6	C17—C12—C11	119.43 (19)
C6—C1—H1	118.6	C13—C12—C11	122.08 (19)
C1—C2—C3	118.7 (2)	C14—C13—C12	120.6 (2)
C1—C2—H2	120.6	C14—C13—H13	119.7
C3—C2—H2	120.6	C12—C13—H13	119.7
C4—C3—C2	121.3 (2)	C15—C14—C13	118.8 (2)
C4—C3—Cl1	119.35 (19)	C15—C14—H14	120.6
C2—C3—Cl1	119.35 (19)	C13—C14—H14	120.6
C3—C4—C5	118.8 (2)	C14—C15—F4	119.3 (2)
C3—C4—H4	120.6	C14—C15—C16	122.7 (2)
C5—C4—H4	120.6	F4—C15—C16	118.0 (2)
C4—C5—C6	122.00 (19)	C15—C16—C17	118.2 (2)
C4—C5—Cl2	117.68 (16)	C15—C16—H16	120.9
C6—C5—Cl2	120.28 (16)	C17—C16—H16	120.9
C1—C6—C5	116.20 (19)	C16—C17—C12	121.2 (2)
C1—C6—C7	118.89 (18)	C16—C17—H17	119.4
C5—C6—C7	124.89 (18)	C12—C17—H17	119.4
C10—C7—C8	104.67 (18)	C19—C18—C11	119.89 (19)
C10—C7—C6	123.92 (18)	C19—C18—H18	120.1
C8—C7—C6	131.06 (18)	C11—C18—H18	120.1
N3—C8—C7	112.92 (18)	C18—C19—N2	118.42 (19)
N3—C8—C9	118.01 (19)	C18—C19—C20	123.09 (19)
C7—C8—C9	129.0 (2)	N2—C19—C20	118.45 (18)
C8—C9—H9A	109.5	F1—C20—F3	107.1 (2)
C8—C9—H9B	109.5	F1—C20—F2	106.34 (19)
H9A—C9—H9B	109.5	F3—C20—F2	107.4 (2)
C8—C9—H9C	109.5	F1—C20—C19	112.21 (19)
H9A—C9—H9C	109.5	F3—C20—C19	110.62 (18)
H9B—C9—H9C	109.5	F2—C20—C19	112.9 (2)
N1—C10—C7	131.82 (19)

C19—N2—N3—C8	179.8 (2)	N3—N2—C10—C7	0.4 (2)
C10—N2—N3—C8	0.0 (2)	C19—N2—C10—C7	−179.44 (19)
C6—C1—C2—C3	0.5 (4)	C10—N1—C11—C18	−1.4 (3)
C1—C2—C3—C4	1.3 (4)	C10—N1—C11—C12	178.00 (18)
C1—C2—C3—Cl1	−178.8 (2)	N1—C11—C12—C17	−10.3 (3)
C2—C3—C4—C5	−1.0 (4)	C18—C11—C12—C17	169.2 (2)
Cl1—C3—C4—C5	179.13 (19)	N1—C11—C12—C13	170.2 (2)
C3—C4—C5—C6	−1.1 (4)	C18—C11—C12—C13	−10.3 (3)
C3—C4—C5—Cl2	176.46 (19)	C17—C12—C13—C14	−0.3 (4)
C2—C1—C6—C5	−2.4 (4)	C11—C12—C13—C14	179.2 (2)
C2—C1—C6—C7	178.6 (2)	C12—C13—C14—C15	−0.8 (4)
C4—C5—C6—C1	2.7 (3)	C13—C14—C15—F4	−179.7 (3)
Cl2—C5—C6—C1	−174.81 (17)	C13—C14—C15—C16	1.4 (5)
C4—C5—C6—C7	−178.3 (2)	C14—C15—C16—C17	−0.9 (4)
Cl2—C5—C6—C7	4.2 (3)	F4—C15—C16—C17	−179.8 (2)
C1—C6—C7—C10	46.2 (3)	C15—C16—C17—C12	−0.2 (4)
C5—C6—C7—C10	−132.7 (2)	C13—C12—C17—C16	0.8 (4)
C1—C6—C7—C8	−125.9 (3)	C11—C12—C17—C16	−178.7 (2)
C5—C6—C7—C8	55.2 (3)	N1—C11—C18—C19	0.4 (3)
N2—N3—C8—C7	−0.4 (2)	C12—C11—C18—C19	−179.0 (2)
N2—N3—C8—C9	177.5 (2)	C11—C18—C19—N2	0.9 (3)
C10—C7—C8—N3	0.6 (3)	C11—C18—C19—C20	−176.8 (2)
C6—C7—C8—N3	173.9 (2)	N3—N2—C19—C18	179.1 (2)
C10—C7—C8—C9	−177.0 (2)	C10—N2—C19—C18	−1.1 (3)
C6—C7—C8—C9	−3.8 (4)	N3—N2—C19—C20	−3.2 (3)
C11—N1—C10—C7	−179.4 (2)	C10—N2—C19—C20	176.65 (19)
C11—N1—C10—N2	1.2 (3)	C18—C19—C20—F1	115.6 (2)
C8—C7—C10—N1	−180.0 (2)	N2—C19—C20—F1	−62.1 (3)
C6—C7—C10—N1	6.1 (4)	C18—C19—C20—F3	−3.9 (3)
C8—C7—C10—N2	−0.6 (2)	N2—C19—C20—F3	178.4 (2)
C6—C7—C10—N2	−174.44 (19)	C18—C19—C20—F2	−124.3 (2)
N3—N2—C10—N1	179.88 (19)	N2—C19—C20—F2	58.1 (3)
C19—N2—C10—N1	0.0 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₁Cl₂F₄N₃
M_r	440.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	9.5361 (19), 15.941 (3), 24.853 (5)
V (Å³)	3778.0 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.926, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	34334, 4477, 3517
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.153, 1.08
No. of reflections	4477
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.34

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the State Key Laboratory of Elemento-organic Chemistry Nankai University, for the X-ray data collection.

References

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