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

In the title compound, C(20)H(11)Cl(2)F(4)N(3), 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 fluoro-benzene ring is rotated out of this plane by 10.3 (3)°, whereas the dichloro-benzene ring is rotated by 46.2 (3)°. The crystal packing is dominated by Cl⋯Cl inter-actions of 3.475 (3) Å and van der Waals inter-actions.

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 = 440.22

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.153

S = 1.08

4477 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017345/kp2407sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812017345/kp2407Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H11Cl2F4N3	F(000) = 1776
Mr = 440.22	Dx = 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

Rigaku Saturn diffractometer	4477 independent reflections
Radiation source: rotating anode	3517 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.049
ω scans	θmax = 27.9°, θmin = 2.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −11→12
Tmin = 0.926, Tmax = 0.940	k = −20→20
34334 measured reflections	l = −32→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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0762P)2 + 0.9456P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
4477 reflections	Δρmax = 0.27 e Å−3
264 parameters	Δρmin = −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)

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	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)

	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)

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)