3-(2,4-Dichloro-phen-yl)-5-(4-fluoro-phen-yl)-2-phenyl-7-(trifluoro-meth-yl)pyrazolo-[1,5-a]pyrimidine.

In the title compound, C(25)H(13)Cl(2)F(4)N(3), there are four planar systems, viz. three benzene rings and a pyrazolo-[1,5-a]pyrim-idine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichloro-phenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluoro-phenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals inter-actions. A Cl⋯Cl inter-action of 3.475 (3) Å also occurs.

Related literature

For background inn class="Chemical">formation 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 = 502.28

Monoclinic,

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 difn class="Chemical">fractometer

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[F 2 > 2σ(n class="Chemical">F 2)] = 0.051

wR(F 2) = 0.143

S = 1.09

3895 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −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 ren class="Chemical">fine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023641/kp2419sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812023641/kp2419Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIn class="Chemical">F report

C25H13Cl2F4N3	F(000) = 1016
Mr = 502.28	Dx = 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

Rigaku Saturn diffractometer	3895 independent reflections
Radiation source: rotating anode	3056 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.041
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −10→10
Tmin = 0.922, Tmax = 0.934	k = −10→7
15847 measured reflections	l = −30→32

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(Fo2) + (0.0833P)2 + 0.040P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3895 reflections	Δρmax = 0.37 e Å−3
308 parameters	Δρmin = −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)

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
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*

	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)

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)