2-Methyl-5-(4-tol-yl)-7-(trifluoro-meth-yl)pyrazolo[1,5-a]pyrimidine.

In the title compound, C(15)H(12)F(3)N(3), the pyrazolo[1,5-a]pyrimidine system ring is essentially planar with a maximum deviation from the mean plane of 0.014 (1) Å. The 4-tolyl group makes a dihedral angle of 14.1 (1)° with the pyrazolo[1,5-a]pyrimidine ring system. The crystal packing is stabilized mainly by van der Waals forces.

Related literature

For related pyrazolopyrimidine compounds, see: Wen et al. (2004 ▶, 2005 ▶); Oliveira-Campos et al. (2006 ▶). For related literature and the synthetic procedure, see: Martins et al. (2004 ▶, 2006 ▶). For the pharmacological activity, see: Almanza et al. (2001 ▶); Novinson et al. (1977 ▶); George (2001 ▶).

Experimental

Crystal data

C15H12F3N3

M = 291.28

Triclinic,

a = 4.8715 (2) Å

b = 11.2655 (5) Å

c = 13.5584 (6) Å

α = 110.225 (3)°

β = 96.808 (3)°

γ = 99.835 (3)°

V = 675.13 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.98 × 0.21 × 0.20 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (XPREP; Bruker, 2006 ▶) T min = 0.874, T max = 0.977

16787 measured reflections

3757 independent reflections

2200 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.227

S = 1.05

3757 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064318/xu2373sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064318/xu2373Isup2.hkl

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

C15H12F3N3	Z = 2
Mr = 291.28	F000 = 300
Triclinic, P1	Dx = 1.433 Mg m−3
Hall symbol: -P 1	Melting point = 415–416 K
a = 4.8715 (2) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.2655 (5) Å	Cell parameters from 150 reflections
c = 13.5584 (6) Å	θ = 3.0–24.6º
α = 110.225 (3)º	µ = 0.12 mm−1
β = 96.808 (3)º	T = 293 (2) K
γ = 99.835 (3)º	Block, yellow
V = 675.13 (5) Å3	0.98 × 0.21 × 0.20 mm

X8 APEXII diffractometer	2200 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 293(2) K	θmax = 29.7º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(XPREP; Bruker, 2006)	h = −6→6
Tmin = 0.874, Tmax = 0.977	k = −15→15
16787 measured reflections	l = −18→18
3757 independent reflections

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.227	w = 1/[σ2(Fo2) + (0.1373P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3757 reflections	Δρmax = 0.40 e Å−3
190 parameters	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N4	−0.1395 (3)	0.64063 (13)	0.15766 (10)	0.0437 (4)
C51	0.2301 (3)	0.60519 (16)	0.27094 (13)	0.0434 (4)
C5	0.0595 (3)	0.69036 (16)	0.24463 (12)	0.0427 (4)
N1A	−0.2415 (3)	0.85107 (14)	0.19699 (11)	0.0475 (4)
C3A	−0.2918 (3)	0.71919 (16)	0.13244 (13)	0.0443 (4)
C7	−0.0385 (4)	0.90322 (17)	0.28737 (15)	0.0517 (4)
N1	−0.4126 (3)	0.91420 (15)	0.15720 (13)	0.0560 (4)
C6	0.1130 (4)	0.82475 (17)	0.31325 (14)	0.0501 (4)
H6	0.2514	0.8577	0.3753	0.06*
C56	0.2277 (4)	0.48484 (18)	0.19505 (14)	0.0526 (5)
H56	0.1165	0.4575	0.1271	0.063*
C55	0.3880 (4)	0.40510 (18)	0.21898 (15)	0.0571 (5)
H55	0.381	0.3245	0.1668	0.069*
C52	0.4029 (4)	0.64261 (19)	0.37085 (15)	0.0584 (5)
H52	0.4097	0.723	0.4233	0.07*
C54	0.5592 (4)	0.44182 (19)	0.31862 (15)	0.0539 (5)
C3	−0.5081 (4)	0.69986 (19)	0.04969 (15)	0.0514 (4)
H3	−0.5939	0.622	−0.0068	0.062*
C2	−0.5725 (4)	0.81980 (18)	0.06756 (15)	0.0522 (5)
C53	0.5645 (5)	0.5626 (2)	0.39352 (16)	0.0631 (5)
H53	0.6796	0.5906	0.4608	0.076*
C8	0.7329 (5)	0.3537 (2)	0.34284 (18)	0.0700 (6)
H8A	0.7031	0.2754	0.2807	0.105*
H8B	0.6763	0.3327	0.4014	0.105*
H8C	0.9303	0.3967	0.3619	0.105*
C71	0.0064 (5)	1.0448 (2)	0.3532 (2)	0.0714 (6)
C21	−0.7881 (4)	0.8562 (2)	0.00171 (18)	0.0689 (6)
H21A	−0.7828	0.9471	0.0353	0.103*
H21B	−0.9738	0.8064	−0.0036	0.103*
H21C	−0.7457	0.8385	−0.0686	0.103*
F3	−0.2264 (3)	1.07474 (12)	0.38784 (11)	0.0893 (5)
F1	0.2076 (3)	1.07989 (12)	0.43939 (12)	0.1008 (6)
F2	0.0852 (3)	1.11914 (12)	0.29935 (14)	0.1004 (5)

	U11	U22	U33	U12	U13	U23
N4	0.0444 (8)	0.0425 (8)	0.0452 (7)	0.0121 (6)	0.0056 (6)	0.0175 (6)
C51	0.0427 (9)	0.0434 (9)	0.0449 (9)	0.0114 (7)	0.0059 (6)	0.0177 (7)
C5	0.0430 (9)	0.0401 (9)	0.0447 (9)	0.0100 (6)	0.0078 (6)	0.0155 (7)
N1A	0.0449 (8)	0.0430 (8)	0.0557 (8)	0.0131 (6)	0.0048 (6)	0.0197 (7)
C3A	0.0449 (9)	0.0425 (9)	0.0476 (9)	0.0113 (7)	0.0081 (7)	0.0191 (7)
C7	0.0478 (10)	0.0399 (9)	0.0606 (11)	0.0105 (7)	0.0043 (8)	0.0121 (8)
N1	0.0507 (9)	0.0533 (10)	0.0723 (10)	0.0189 (7)	0.0068 (7)	0.0318 (8)
C6	0.0472 (10)	0.0425 (9)	0.0522 (10)	0.0106 (7)	−0.0016 (7)	0.0109 (8)
C56	0.0583 (11)	0.0473 (10)	0.0510 (10)	0.0183 (8)	0.0021 (8)	0.0168 (8)
C55	0.0628 (12)	0.0511 (11)	0.0613 (11)	0.0257 (9)	0.0107 (9)	0.0201 (9)
C52	0.0654 (12)	0.0500 (11)	0.0530 (10)	0.0179 (9)	−0.0029 (9)	0.0133 (8)
C54	0.0471 (10)	0.0617 (12)	0.0653 (11)	0.0200 (8)	0.0125 (8)	0.0346 (9)
C3	0.0495 (10)	0.0514 (10)	0.0526 (9)	0.0108 (7)	0.0018 (7)	0.0213 (8)
C2	0.0453 (9)	0.0570 (11)	0.0617 (11)	0.0134 (8)	0.0080 (8)	0.0310 (9)
C53	0.0654 (12)	0.0637 (13)	0.0580 (11)	0.0204 (9)	−0.0065 (9)	0.0233 (10)
C8	0.0662 (13)	0.0779 (14)	0.0844 (15)	0.0355 (11)	0.0151 (11)	0.0438 (12)
C71	0.0619 (13)	0.0448 (11)	0.0919 (16)	0.0169 (9)	−0.0039 (11)	0.0104 (11)
C21	0.0577 (12)	0.0765 (15)	0.0826 (14)	0.0196 (10)	0.0006 (10)	0.0442 (12)
F3	0.0826 (10)	0.0650 (9)	0.1014 (10)	0.0344 (7)	0.0122 (8)	0.0017 (7)
F1	0.0906 (11)	0.0543 (8)	0.1095 (11)	0.0197 (7)	−0.0302 (9)	−0.0132 (7)
F2	0.0970 (11)	0.0468 (8)	0.1534 (14)	0.0113 (7)	0.0153 (10)	0.0378 (8)

N4—C5	1.316 (2)	C52—C53	1.379 (3)
N4—C3A	1.351 (2)	C52—H52	0.93
C51—C56	1.387 (2)	C54—C53	1.382 (3)
C51—C52	1.391 (2)	C54—C8	1.502 (3)
C51—C5	1.475 (2)	C3—C2	1.385 (3)
C5—C6	1.435 (2)	C3—H3	0.93
N1A—C7	1.357 (2)	C2—C21	1.499 (3)
N1A—N1	1.3609 (19)	C53—H53	0.93
N1A—C3A	1.400 (2)	C8—H8A	0.96
C3A—C3	1.375 (2)	C8—H8B	0.96
C7—C6	1.351 (2)	C8—H8C	0.96
C7—C71	1.496 (3)	C71—F1	1.326 (2)
N1—C2	1.347 (2)	C71—F2	1.328 (3)
C6—H6	0.93	C71—F3	1.330 (3)
C56—C55	1.380 (2)	C21—H21A	0.96
C56—H56	0.93	C21—H21B	0.96
C55—C54	1.386 (3)	C21—H21C	0.96
C55—H55	0.93
C5—N4—C3A	118.71 (14)	C53—C54—C8	121.90 (18)
C56—C51—C52	117.46 (16)	C55—C54—C8	120.90 (18)
C56—C51—C5	120.61 (15)	C3A—C3—C2	106.06 (16)
C52—C51—C5	121.91 (15)	C3A—C3—H3	127
N4—C5—C6	121.31 (15)	C2—C3—H3	127
N4—C5—C51	118.72 (14)	N1—C2—C3	113.05 (16)
C6—C5—C51	119.96 (15)	N1—C2—C21	117.78 (17)
C7—N1A—N1	127.00 (15)	C3—C2—C21	129.17 (17)
C7—N1A—C3A	120.58 (14)	C52—C53—C54	121.53 (17)
N1—N1A—C3A	112.42 (14)	C52—C53—H53	119.2
N4—C3A—C3	133.62 (16)	C54—C53—H53	119.2
N4—C3A—N1A	121.23 (15)	C54—C8—H8A	109.5
C3—C3A—N1A	105.15 (15)	C54—C8—H8B	109.5
C6—C7—N1A	118.36 (16)	H8A—C8—H8B	109.5
C6—C7—C71	123.34 (17)	C54—C8—H8C	109.5
N1A—C7—C71	118.31 (16)	H8A—C8—H8C	109.5
C2—N1—N1A	103.32 (14)	H8B—C8—H8C	109.5
C7—C6—C5	119.78 (16)	F1—C71—F2	107.13 (18)
C7—C6—H6	120.1	F1—C71—F3	106.74 (19)
C5—C6—H6	120.1	F2—C71—F3	107.32 (18)
C55—C56—C51	120.88 (17)	F1—C71—C7	110.86 (17)
C55—C56—H56	119.6	F2—C71—C7	112.3 (2)
C51—C56—H56	119.6	F3—C71—C7	112.17 (18)
C56—C55—C54	121.77 (17)	C2—C21—H21A	109.5
C56—C55—H55	119.1	C2—C21—H21B	109.5
C54—C55—H55	119.1	H21A—C21—H21B	109.5
C53—C52—C51	121.14 (17)	C2—C21—H21C	109.5
C53—C52—H52	119.4	H21A—C21—H21C	109.5
C51—C52—H52	119.4	H21B—C21—H21C	109.5
C53—C54—C55	117.20 (17)
N4—C51—C5—C56	−14.5 (3)	N4—C51—C5—C52	166.90 (16)