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

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

doi:10.1107/S1600536812023641

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1923

doi:10.1107/S1600536812023641

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

Ju Liu,^a Zhi-Qiang Cai,^b,^c ^* Yang Wang,^a Yu-Li Sang ^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

(Received 18 May 2012; accepted 24 May 2012; online 31 May 2012)

In the title compound, C₂₅H₁₃Cl₂F₄N₃, there are four planar systems, viz. three benzene rings and a pyrazolo[1,5-a]pyrimidine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichlorophenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluorophenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals interactions. A Cl⋯Cl interaction of 3.475 (3) Å also occurs.

Related literature

For background information and the related structures, see: Liu et al. (2012 ); Frizzo et al. (2008 ); Bui et al. (2009 ). For the synthesis of other pyrozolo[1,5-a]pyrimidine derivatives and for their pharmacological applications, see: Fraley et al. (2012 ); Dalinger et al. (2005 ); Dennis et al. (2004 ).

Experimental

Crystal data

C₂₅H₁₃Cl₂F₄N₃
M_r = 502.28
Monoclinic, P 2₁ /c
a = 9.0826 (18) Å
b = 9.0606 (18) Å
c = 27.259 (6) Å
β = 99.46 (3)°
V = 2212.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.922, T_max = 0.934
15847 measured reflections
3895 independent reflections
3056 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.143
S = 1.09
3895 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.46 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/S1600536812023641/kp2419sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023641/kp2419Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023641/kp2419Isup3.cml

checkCIF report

Comment top

The pyrazolo[1,5-a]pyrimidine structural motif may be found in a large number of pharmaceutical agents with a diverse range of physiological activities, for example, antiepileptic agents, anxiolytics, antidepressants, agents for treatment of sleep disorders and oncolytics. A series of antagonist of protease-activated PAR2 receptors were reported (Fraley, et al., 2012 and Dalinger, et al., 2005). As a part of our ongoing study of pyrazolo[1,5-a]pyrimidine derivatives containing 5-(4-fluorophenyl) and 3-(2,4-dichlorophenyl) substituents (Liu, et al., 2012), we report herein the crystal structure of the title compound.

The title molecule (Fig. 1) bond lengths and angles are generally within normal ranges. The dihedral angles between fluorobenzene ring and benzene ring is 7.97°. The dihedral angle between dichlorophenyl ring and benzene ring is 69.95°. The torsion angles C(16)—C(17)—C(18)—C(19), N(2)—N(1)—C(1)—C(2), C(21)—C(22)—C(23)—F(4) and C(10)—C(11)—C(12)—Cl(2) are -178.71 (19), 175.35 (17), -178.4 (2) and -179.9 (2), respectively. The crystal structure is held together by van der Waals forces and pronounced Cl···Cl interaction of 3.475 (3) Å (Bui, et al., 2009).

Related literature top

For background information and the related structures, see: Liu et al. (2012); Frizzo et al. (2008); Bui et al. (2009). For the synthesis of other pyrozolo[1,5-a]pyrimidine derivatives and for their pharmacological applications, see: Fraley et al. (2012); Dalinger et al. (2005); Dennis et al. (2004).

Experimental top

A mixture of the corresponding 4-(2,4-dichlorophenyl)-3-phenyl-1H-pyrazol-5-amine (1.50 g, 4.93 mmol) and the 4,4,4-trifluoro-1-(4-fluorophenyl)butane-1,3-dione (1.27 g, 5.42 6 mmol) in a flask (25 mL) was heated at 453–458 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 (1.55 g, 62.58%). Crystals suitable for X-ray analysis were obtained from EtOH : EtOAc(1:1) solution mixture 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 C₂₅H₁₃Cl₂F₄N₃ with all non-H atom-labelling scheme and ellipsoids drawn at the 50% probability level.

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

Crystal data top

C₂₅H₁₃Cl₂F₄N₃	F(000) = 1016
M_r = 502.28	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5009 reflections
a = 9.0826 (18) Å	θ = 2.3–27.9°
b = 9.0606 (18) Å	µ = 0.35 mm⁻¹
c = 27.259 (6) Å	T = 293 K
β = 99.46 (3)°	Prism, yellow
V = 2212.7 (8) Å³	0.24 × 0.22 × 0.20 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	3895 independent reflections
Radiation source: rotating anode	3056 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.041
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −10→10
T_min = 0.922, T_max = 0.934	k = −10→7
15847 measured reflections	l = −30→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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.143	w = 1/[σ²(F_o²) + (0.0833P)² + 0.040P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
3895 reflections	Δρ_max = 0.37 e Å⁻³
308 parameters	Δρ_min = −0.46 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: 0.028 (3)

Crystal data top

C₂₅H₁₃Cl₂F₄N₃	V = 2212.7 (8) Å³
M_r = 502.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0826 (18) Å	µ = 0.35 mm⁻¹
b = 9.0606 (18) Å	T = 293 K
c = 27.259 (6) Å	0.24 × 0.22 × 0.20 mm
β = 99.46 (3)°

Data collection top

Rigaku Saturn diffractometer	3895 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3056 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.934	R_int = 0.041
15847 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.09	Δρ_max = 0.37 e Å⁻³
3895 reflections	Δρ_min = −0.46 e Å⁻³
308 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	1.31929 (9)	0.44828 (10)	0.47969 (3)	0.0868 (3)
Cl2	0.94948 (12)	0.20741 (11)	0.59085 (3)	0.1024 (4)
F1	1.09069 (17)	0.35785 (15)	0.20644 (5)	0.0619 (4)
F2	1.2102 (2)	0.5478 (2)	0.23496 (6)	0.0886 (6)
F3	0.9955 (2)	0.56762 (17)	0.18909 (5)	0.0831 (6)
F4	0.24299 (18)	0.7892 (2)	0.32444 (6)	0.0917 (6)
N1	1.2012 (2)	0.33960 (19)	0.31669 (6)	0.0413 (4)
N2	1.0698 (2)	0.41358 (18)	0.31156 (6)	0.0385 (4)
N3	0.8699 (2)	0.47095 (19)	0.35650 (6)	0.0401 (4)
C1	1.2191 (2)	0.2873 (2)	0.36384 (7)	0.0388 (5)
C2	1.3488 (2)	0.1903 (2)	0.37979 (8)	0.0432 (5)
C3	1.4710 (3)	0.1954 (3)	0.35534 (9)	0.0542 (6)
H3	1.4737	0.2649	0.3304	0.065*
C4	1.5895 (3)	0.0981 (3)	0.36768 (10)	0.0670 (8)
H4	1.6707	0.1023	0.3509	0.080*
C5	1.5865 (3)	−0.0044 (3)	0.40471 (11)	0.0727 (9)
H5	1.6655	−0.0701	0.4129	0.087*
C6	1.4674 (4)	−0.0098 (3)	0.42954 (11)	0.0731 (8)
H6	1.4664	−0.0782	0.4549	0.088*
C7	1.3487 (3)	0.0857 (3)	0.41720 (9)	0.0594 (7)
H7	1.2678	0.0802	0.4341	0.071*
C8	1.1017 (2)	0.3286 (2)	0.38894 (7)	0.0395 (5)
C9	1.0711 (2)	0.2977 (2)	0.43952 (7)	0.0402 (5)
C10	1.1586 (3)	0.3478 (2)	0.48288 (8)	0.0468 (6)
C11	1.1222 (3)	0.3204 (3)	0.52918 (8)	0.0553 (7)
H11	1.1831	0.3551	0.5576	0.066*
C12	0.9960 (3)	0.2419 (3)	0.53295 (8)	0.0592 (7)
C13	0.9050 (3)	0.1923 (3)	0.49108 (10)	0.0747 (9)
H13	0.8181	0.1407	0.4936	0.090*
C14	0.9437 (3)	0.2199 (3)	0.44528 (9)	0.0620 (7)
H14	0.8820	0.1849	0.4170	0.074*
C15	1.0032 (2)	0.4081 (2)	0.35423 (7)	0.0378 (5)
C16	0.8006 (2)	0.5390 (2)	0.31605 (7)	0.0386 (5)
C17	0.8643 (3)	0.5463 (2)	0.27171 (8)	0.0424 (5)
H17	0.8129	0.5937	0.2438	0.051*
C18	0.9989 (2)	0.4847 (2)	0.27000 (7)	0.0394 (5)
C19	1.0751 (3)	0.4900 (3)	0.22528 (8)	0.0461 (6)
C20	0.6539 (2)	0.6071 (2)	0.31877 (7)	0.0396 (5)
C21	0.5912 (3)	0.7106 (3)	0.28349 (9)	0.0493 (6)
H21	0.6427	0.7381	0.2581	0.059*
C22	0.4542 (3)	0.7726 (3)	0.28576 (9)	0.0573 (7)
H22	0.4130	0.8419	0.2623	0.069*
C23	0.3796 (3)	0.7307 (3)	0.32307 (10)	0.0576 (7)
C24	0.4372 (3)	0.6316 (3)	0.35902 (9)	0.0564 (6)
H24	0.3848	0.6061	0.3844	0.068*
C25	0.5753 (3)	0.5702 (2)	0.35670 (8)	0.0473 (6)
H25	0.6163	0.5030	0.3809	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0765 (6)	0.1313 (7)	0.0511 (4)	−0.0570 (5)	0.0062 (4)	−0.0089 (4)
Cl2	0.1446 (9)	0.1281 (8)	0.0411 (4)	−0.0592 (6)	0.0350 (5)	−0.0028 (4)
F1	0.0830 (11)	0.0617 (9)	0.0432 (8)	0.0200 (7)	0.0171 (7)	−0.0052 (6)
F2	0.0899 (13)	0.1194 (15)	0.0648 (10)	−0.0465 (11)	0.0371 (9)	−0.0103 (9)
F3	0.1145 (14)	0.0927 (12)	0.0507 (9)	0.0534 (10)	0.0388 (9)	0.0330 (8)
F4	0.0567 (10)	0.1403 (16)	0.0836 (12)	0.0343 (10)	0.0276 (9)	0.0172 (11)
N1	0.0423 (11)	0.0467 (10)	0.0346 (9)	−0.0032 (8)	0.0056 (8)	−0.0020 (8)
N2	0.0449 (11)	0.0409 (10)	0.0303 (9)	0.0002 (8)	0.0075 (8)	0.0001 (7)
N3	0.0425 (10)	0.0471 (10)	0.0315 (9)	−0.0027 (8)	0.0083 (8)	−0.0011 (8)
C1	0.0382 (12)	0.0458 (12)	0.0321 (11)	−0.0077 (9)	0.0049 (9)	−0.0040 (9)
C2	0.0425 (13)	0.0500 (13)	0.0356 (11)	−0.0023 (10)	0.0021 (10)	−0.0076 (10)
C3	0.0491 (14)	0.0662 (15)	0.0459 (14)	−0.0023 (12)	0.0033 (11)	−0.0048 (12)
C4	0.0484 (16)	0.087 (2)	0.0648 (17)	0.0074 (14)	0.0059 (13)	−0.0123 (16)
C5	0.0590 (19)	0.0739 (18)	0.080 (2)	0.0197 (15)	−0.0047 (16)	−0.0118 (16)
C6	0.080 (2)	0.0664 (17)	0.0702 (19)	0.0159 (16)	0.0042 (16)	0.0117 (15)
C7	0.0614 (16)	0.0612 (15)	0.0560 (16)	0.0081 (13)	0.0108 (13)	0.0055 (12)
C8	0.0430 (12)	0.0447 (12)	0.0299 (10)	−0.0063 (9)	0.0036 (9)	−0.0008 (9)
C9	0.0408 (12)	0.0465 (12)	0.0320 (11)	−0.0018 (10)	0.0028 (9)	0.0022 (9)
C10	0.0486 (14)	0.0560 (14)	0.0344 (12)	−0.0109 (11)	0.0024 (10)	−0.0003 (10)
C11	0.0632 (16)	0.0666 (16)	0.0337 (12)	−0.0140 (13)	0.0010 (11)	−0.0032 (11)
C12	0.0747 (18)	0.0703 (16)	0.0346 (13)	−0.0133 (14)	0.0148 (12)	0.0029 (11)
C13	0.0732 (19)	0.104 (2)	0.0478 (15)	−0.0433 (17)	0.0131 (14)	0.0027 (15)
C14	0.0591 (16)	0.0897 (19)	0.0355 (13)	−0.0285 (14)	0.0028 (11)	−0.0048 (12)
C15	0.0424 (12)	0.0442 (12)	0.0274 (10)	−0.0045 (9)	0.0071 (9)	−0.0028 (9)
C16	0.0439 (12)	0.0378 (11)	0.0338 (11)	−0.0055 (9)	0.0052 (9)	−0.0028 (9)
C17	0.0494 (14)	0.0440 (12)	0.0341 (11)	0.0012 (10)	0.0074 (10)	0.0014 (9)
C18	0.0518 (14)	0.0371 (11)	0.0303 (11)	−0.0035 (10)	0.0095 (10)	−0.0006 (9)
C19	0.0576 (15)	0.0468 (13)	0.0358 (12)	0.0053 (11)	0.0133 (11)	0.0039 (10)
C20	0.0407 (12)	0.0421 (12)	0.0362 (11)	−0.0068 (9)	0.0064 (9)	−0.0043 (9)
C21	0.0441 (13)	0.0639 (15)	0.0404 (12)	−0.0012 (11)	0.0080 (10)	0.0047 (11)
C22	0.0495 (14)	0.0713 (16)	0.0504 (14)	0.0128 (12)	0.0064 (12)	0.0111 (12)
C23	0.0412 (14)	0.0759 (17)	0.0563 (15)	0.0061 (12)	0.0093 (12)	−0.0060 (13)
C24	0.0552 (15)	0.0684 (16)	0.0504 (14)	−0.0040 (13)	0.0227 (12)	−0.0013 (13)
C25	0.0540 (14)	0.0510 (13)	0.0389 (12)	−0.0036 (11)	0.0134 (11)	0.0012 (10)

Geometric parameters (Å, º) top

Cl1—C10	1.734 (2)	C8—C9	1.477 (3)
Cl2—C12	1.728 (2)	C9—C14	1.386 (3)
F1—C19	1.320 (3)	C9—C10	1.387 (3)
F2—C19	1.320 (3)	C10—C11	1.379 (3)
F3—C19	1.325 (2)	C11—C12	1.367 (3)
F4—C23	1.356 (3)	C11—H11	0.9300
N1—C1	1.354 (3)	C12—C13	1.370 (3)
N1—N2	1.356 (2)	C13—C14	1.375 (3)
N2—C18	1.369 (3)	C13—H13	0.9300
N2—C15	1.397 (3)	C14—H14	0.9300
N3—C16	1.328 (3)	C16—C17	1.425 (3)
N3—C15	1.349 (3)	C16—C20	1.481 (3)
C1—C8	1.409 (3)	C17—C18	1.352 (3)
C1—C2	1.477 (3)	C17—H17	0.9300
C2—C3	1.386 (3)	C18—C19	1.498 (3)
C2—C7	1.392 (3)	C20—C25	1.390 (3)
C3—C4	1.389 (4)	C20—C21	1.396 (3)
C3—H3	0.9300	C21—C22	1.376 (3)
C4—C5	1.375 (4)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.365 (4)
C5—C6	1.369 (4)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.368 (4)
C6—C7	1.380 (4)	C24—C25	1.384 (3)
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—H25	0.9300
C8—C15	1.391 (3)

C1—N1—N2	103.71 (17)	C12—C13—H13	120.4
N1—N2—C18	127.17 (18)	C14—C13—H13	120.4
N1—N2—C15	112.99 (16)	C13—C14—C9	122.6 (2)
C18—N2—C15	119.81 (18)	C13—C14—H14	118.7
C16—N3—C15	117.66 (18)	C9—C14—H14	118.7
N1—C1—C8	112.68 (18)	N3—C15—C8	131.98 (19)
N1—C1—C2	116.95 (19)	N3—C15—N2	122.52 (18)
C8—C1—C2	130.22 (19)	C8—C15—N2	105.50 (19)
C3—C2—C7	118.2 (2)	N3—C16—C17	121.5 (2)
C3—C2—C1	120.1 (2)	N3—C16—C20	117.33 (19)
C7—C2—C1	121.6 (2)	C17—C16—C20	121.14 (19)
C2—C3—C4	120.8 (2)	C18—C17—C16	120.4 (2)
C2—C3—H3	119.6	C18—C17—H17	119.8
C4—C3—H3	119.6	C16—C17—H17	119.8
C5—C4—C3	119.9 (3)	C17—C18—N2	118.08 (19)
C5—C4—H4	120.0	C17—C18—C19	123.80 (19)
C3—C4—H4	120.0	N2—C18—C19	118.1 (2)
C6—C5—C4	119.9 (3)	F1—C19—F2	106.4 (2)
C6—C5—H5	120.0	F1—C19—F3	105.79 (17)
C4—C5—H5	120.0	F2—C19—F3	108.3 (2)
C5—C6—C7	120.4 (3)	F1—C19—C18	112.40 (18)
C5—C6—H6	119.8	F2—C19—C18	112.87 (18)
C7—C6—H6	119.8	F3—C19—C18	110.76 (19)
C6—C7—C2	120.7 (3)	C25—C20—C21	118.2 (2)
C6—C7—H7	119.6	C25—C20—C16	120.87 (19)
C2—C7—H7	119.6	C21—C20—C16	120.9 (2)
C15—C8—C1	105.08 (18)	C22—C21—C20	120.9 (2)
C15—C8—C9	122.3 (2)	C22—C21—H21	119.6
C1—C8—C9	132.56 (19)	C20—C21—H21	119.6
C14—C9—C10	116.2 (2)	C23—C22—C21	118.9 (2)
C14—C9—C8	119.36 (18)	C23—C22—H22	120.6
C10—C9—C8	124.3 (2)	C21—C22—H22	120.6
C11—C10—C9	122.1 (2)	F4—C23—C22	118.7 (2)
C11—C10—Cl1	118.08 (17)	F4—C23—C24	118.7 (2)
C9—C10—Cl1	119.85 (17)	C22—C23—C24	122.6 (2)
C12—C11—C10	119.5 (2)	C23—C24—C25	118.3 (2)
C12—C11—H11	120.2	C23—C24—H24	120.9
C10—C11—H11	120.2	C25—C24—H24	120.9
C11—C12—C13	120.4 (2)	C24—C25—C20	121.2 (2)
C11—C12—Cl2	119.78 (19)	C24—C25—H25	119.4
C13—C12—Cl2	119.8 (2)	C20—C25—H25	119.4
C12—C13—C14	119.2 (2)

C1—N1—N2—C18	−178.37 (19)	C1—C8—C15—N3	177.8 (2)
C1—N1—N2—C15	−0.6 (2)	C9—C8—C15—N3	−0.1 (3)
N2—N1—C1—C8	−0.7 (2)	C1—C8—C15—N2	−2.0 (2)
N2—N1—C1—C2	175.35 (17)	C9—C8—C15—N2	−179.81 (18)
N1—C1—C2—C3	22.1 (3)	N1—N2—C15—N3	−178.07 (17)
C8—C1—C2—C3	−162.6 (2)	C18—N2—C15—N3	−0.1 (3)
N1—C1—C2—C7	−153.9 (2)	N1—N2—C15—C8	1.7 (2)
C8—C1—C2—C7	21.4 (3)	C18—N2—C15—C8	179.63 (17)
C7—C2—C3—C4	0.4 (3)	C15—N3—C16—C17	−0.2 (3)
C1—C2—C3—C4	−175.6 (2)	C15—N3—C16—C20	179.71 (17)
C2—C3—C4—C5	−0.3 (4)	N3—C16—C17—C18	−0.7 (3)
C3—C4—C5—C6	−0.4 (4)	C20—C16—C17—C18	179.40 (18)
C4—C5—C6—C7	1.0 (4)	C16—C17—C18—N2	1.2 (3)
C5—C6—C7—C2	−0.8 (4)	C16—C17—C18—C19	−178.71 (19)
C3—C2—C7—C6	0.1 (4)	N1—N2—C18—C17	176.86 (18)
C1—C2—C7—C6	176.1 (2)	C15—N2—C18—C17	−0.8 (3)
N1—C1—C8—C15	1.8 (2)	N1—N2—C18—C19	−3.3 (3)
C2—C1—C8—C15	−173.7 (2)	C15—N2—C18—C19	179.10 (19)
N1—C1—C8—C9	179.3 (2)	C17—C18—C19—F1	−115.6 (2)
C2—C1—C8—C9	3.9 (4)	N2—C18—C19—F1	64.6 (3)
C15—C8—C9—C14	59.2 (3)	C17—C18—C19—F2	124.1 (2)
C1—C8—C9—C14	−118.0 (3)	N2—C18—C19—F2	−55.8 (3)
C15—C8—C9—C10	−117.6 (2)	C17—C18—C19—F3	2.5 (3)
C1—C8—C9—C10	65.3 (3)	N2—C18—C19—F3	−177.34 (19)
C14—C9—C10—C11	0.7 (4)	N3—C16—C20—C25	−15.9 (3)
C8—C9—C10—C11	177.6 (2)	C17—C16—C20—C25	164.1 (2)
C14—C9—C10—Cl1	−179.21 (19)	N3—C16—C20—C21	163.79 (19)
C8—C9—C10—Cl1	−2.3 (3)	C17—C16—C20—C21	−16.3 (3)
C9—C10—C11—C12	−0.2 (4)	C25—C20—C21—C22	−1.1 (3)
Cl1—C10—C11—C12	179.8 (2)	C16—C20—C21—C22	179.3 (2)
C10—C11—C12—C13	−0.9 (4)	C20—C21—C22—C23	−0.3 (4)
C10—C11—C12—Cl2	−179.9 (2)	C21—C22—C23—F4	−178.4 (2)
C11—C12—C13—C14	1.3 (5)	C21—C22—C23—C24	1.4 (4)
Cl2—C12—C13—C14	−179.7 (2)	F4—C23—C24—C25	178.7 (2)
C12—C13—C14—C9	−0.7 (5)	C22—C23—C24—C25	−1.1 (4)
C10—C9—C14—C13	−0.3 (4)	C23—C24—C25—C20	−0.3 (4)
C8—C9—C14—C13	−177.3 (3)	C21—C20—C25—C24	1.4 (3)
C16—N3—C15—C8	−179.1 (2)	C16—C20—C25—C24	−179.0 (2)
C16—N3—C15—N2	0.6 (3)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₃Cl₂F₄N₃
M_r	502.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.0826 (18), 9.0606 (18), 27.259 (6)
β (°)	99.46 (3)
V (Å³)	2212.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.922, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	15847, 3895, 3056
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.143, 1.09
No. of reflections	3895
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.46

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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