4-(4-Chloro-5-methyl-3-trifluoro-meth-yl-1H-pyrazol-1-yl)-6-(prop-2-ynyl-oxy)pyrimidine.

The molecule of the title compound, C(12)H(8)ClF(3)N(4)O, is twisted as indicated by the C-O-C-C torsion angle of 76.9 (3)°. Moreover, the trifluoro-methyl group shows rotational disorder of the F atoms, with site-occupancy factors of 0.653 (6) and 0.347 (6). The dihedral angle between the rings is 1.88 (12) Å.

Related literature

For the applications of pyrazole derivatives, see: Hirai et al. (2002 ▶); Krishnaiah et al. (2002 ▶); Ohno et al. (2004 ▶); Li et al. (2008 ▶); Shiga et al. (2003 ▶); Vicentini et al. (2007 ▶).

Experimental

Crystal data

C12H8ClF3N4O

M = 316.67

Monoclinic,

a = 7.8331 (13) Å

b = 7.7258 (12) Å

c = 21.757 (4) Å

β = 99.270 (11)°

V = 1299.5 (4) Å3

Z = 4

Cu Kα radiation

μ = 3.02 mm−1

T = 173 K

0.20 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.583, T max = 0.752

8543 measured reflections

2361 independent reflections

2009 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.106

S = 1.07

2361 reflections

220 parameters

69 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031740/rn2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031740/rn2068Isup2.hkl

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

C12H8ClF3N4O	F(000) = 640
Mr = 316.67	Dx = 1.619 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54186 Å
a = 7.8331 (13) Å	Cell parameters from 564 reflections
b = 7.7258 (12) Å	θ = 2.2–68.3°
c = 21.757 (4) Å	µ = 3.02 mm−1
β = 99.270 (11)°	T = 173 K
V = 1299.5 (4) Å3	Platelet, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Rigaku R-AXIS RAPID IP area-detector diffractometer	2361 independent reflections
Radiation source: rotating anode	2009 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans at fixed χ = 45°	θmax = 68.3°, θmin = 4.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.583, Tmax = 0.752	k = −9→6
8543 measured reflections	l = −26→22

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.8523P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.016
2361 reflections	Δρmax = 0.31 e Å−3
220 parameters	Δρmin = −0.22 e Å−3
69 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: 0.0054 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
Cl1	0.05485 (8)	0.66461 (9)	0.12912 (3)	0.0419 (2)
F1	0.0581 (14)	1.0026 (19)	0.2067 (6)	0.068 (3)	0.65 (3)
F2	0.1586 (17)	1.2382 (8)	0.1787 (5)	0.066 (2)	0.65 (3)
F3	0.3301 (10)	1.040 (2)	0.2184 (4)	0.080 (3)	0.65 (3)
F1'	0.038 (2)	1.038 (4)	0.2018 (12)	0.062 (4)	0.35 (3)
F2'	0.229 (4)	1.227 (2)	0.1908 (8)	0.074 (4)	0.35 (3)
F3'	0.298 (3)	0.977 (3)	0.2215 (7)	0.076 (4)	0.35 (3)
O1	0.4744 (2)	1.4528 (2)	−0.08155 (7)	0.0328 (4)
N1	0.2473 (2)	1.0968 (3)	0.07612 (9)	0.0307 (5)
N2	0.2397 (2)	0.9953 (2)	0.02454 (9)	0.0273 (4)
N3	0.2814 (3)	0.9661 (3)	−0.07855 (9)	0.0339 (5)
N4	0.4008 (2)	1.1943 (3)	−0.13275 (9)	0.0300 (5)
C1	0.1864 (3)	0.9977 (3)	0.11729 (11)	0.0298 (5)
C2	0.1401 (3)	0.8333 (3)	0.09272 (11)	0.0292 (5)
C3	0.1757 (3)	0.8320 (3)	0.03301 (11)	0.0280 (5)
C4	0.1845 (3)	1.0661 (4)	0.18093 (13)	0.0407 (6)
C5	0.1542 (3)	0.6869 (3)	−0.01239 (12)	0.0369 (6)
H5A	0.2630	0.6681	−0.0282	0.055*
H5B	0.0626	0.7155	−0.0471	0.055*
H5C	0.1228	0.5814	0.0082	0.055*
C6	0.2966 (3)	1.0682 (3)	−0.02856 (10)	0.0261 (5)
C7	0.3362 (3)	1.0361 (3)	−0.12775 (12)	0.0349 (6)
H7A	0.3284	0.9648	−0.1637	0.042*
C8	0.4111 (3)	1.2901 (3)	−0.08172 (11)	0.0271 (5)
C9	0.3614 (3)	1.2338 (3)	−0.02663 (10)	0.0275 (5)
H9A	0.3714	1.3042	0.0096	0.033*
C10	0.5077 (3)	1.5223 (3)	−0.14053 (11)	0.0350 (6)
H10A	0.5662	1.4332	−0.1624	0.042*
H10B	0.5861	1.6231	−0.1325	0.042*
C11	0.3481 (3)	1.5756 (3)	−0.18034 (11)	0.0355 (6)
C12	0.2244 (4)	1.6239 (4)	−0.21331 (13)	0.0516 (8)
H12	0.1240	1.6632	−0.2401	0.062*

	U11	U22	U33	U12	U13	U23
Cl1	0.0394 (4)	0.0400 (4)	0.0474 (4)	−0.0066 (3)	0.0100 (3)	0.0144 (3)
F1	0.087 (5)	0.079 (5)	0.049 (3)	−0.028 (4)	0.042 (4)	−0.006 (3)
F2	0.111 (5)	0.046 (2)	0.048 (3)	0.007 (3)	0.035 (3)	−0.0082 (17)
F3	0.055 (2)	0.137 (6)	0.046 (3)	0.014 (3)	−0.0046 (18)	−0.036 (3)
F1'	0.040 (5)	0.092 (9)	0.058 (6)	0.002 (5)	0.021 (4)	−0.015 (6)
F2'	0.128 (9)	0.058 (5)	0.044 (5)	−0.048 (6)	0.034 (6)	−0.014 (4)
F3'	0.089 (7)	0.092 (8)	0.038 (4)	0.028 (5)	−0.015 (4)	0.006 (5)
O1	0.0436 (10)	0.0302 (9)	0.0243 (9)	−0.0109 (8)	0.0043 (7)	0.0016 (7)
N1	0.0350 (11)	0.0304 (11)	0.0280 (11)	−0.0009 (9)	0.0088 (8)	−0.0017 (8)
N2	0.0286 (10)	0.0263 (10)	0.0275 (10)	−0.0011 (8)	0.0057 (8)	0.0002 (8)
N3	0.0423 (12)	0.0294 (11)	0.0307 (11)	−0.0047 (9)	0.0079 (9)	−0.0037 (9)
N4	0.0310 (10)	0.0307 (11)	0.0288 (11)	−0.0015 (9)	0.0064 (8)	−0.0027 (8)
C1	0.0274 (12)	0.0326 (13)	0.0302 (13)	0.0023 (10)	0.0070 (9)	0.0035 (10)
C2	0.0239 (11)	0.0312 (13)	0.0329 (13)	−0.0002 (10)	0.0058 (9)	0.0075 (10)
C3	0.0220 (11)	0.0263 (12)	0.0350 (13)	0.0006 (9)	0.0023 (9)	0.0026 (10)
C4	0.0404 (14)	0.0476 (17)	0.0370 (15)	−0.0060 (13)	0.0149 (12)	0.0012 (12)
C5	0.0393 (13)	0.0305 (13)	0.0405 (15)	−0.0069 (11)	0.0053 (11)	−0.0012 (11)
C6	0.0237 (11)	0.0276 (12)	0.0269 (12)	0.0016 (9)	0.0040 (9)	0.0013 (9)
C7	0.0447 (14)	0.0318 (14)	0.0292 (13)	−0.0044 (11)	0.0095 (11)	−0.0075 (10)
C8	0.0243 (11)	0.0260 (12)	0.0305 (13)	−0.0012 (9)	0.0032 (9)	0.0005 (10)
C9	0.0320 (12)	0.0254 (12)	0.0248 (12)	−0.0024 (10)	0.0035 (9)	−0.0017 (9)
C10	0.0406 (14)	0.0362 (14)	0.0290 (13)	−0.0099 (11)	0.0078 (10)	0.0053 (11)
C11	0.0497 (15)	0.0310 (14)	0.0269 (13)	0.0004 (12)	0.0093 (11)	−0.0015 (10)
C12	0.0613 (19)	0.0503 (18)	0.0402 (16)	0.0150 (15)	−0.0008 (14)	−0.0051 (14)

Cl1—C2	1.715 (2)	C1—C2	1.403 (3)
F1—C4	1.309 (7)	C1—C4	1.484 (4)
F2—C4	1.344 (6)	C2—C3	1.372 (3)
F3—C4	1.306 (7)	C3—C5	1.486 (3)
F1'—C4	1.316 (12)	C5—H5A	0.9800
F2'—C4	1.300 (11)	C5—H5B	0.9800
F3'—C4	1.339 (10)	C5—H5C	0.9800
O1—C8	1.352 (3)	C6—C9	1.374 (3)
O1—C10	1.452 (3)	C7—H7A	0.9500
N1—C1	1.324 (3)	C8—C9	1.389 (3)
N1—N2	1.362 (3)	C9—H9A	0.9500
N2—C3	1.380 (3)	C10—C11	1.461 (3)
N2—C6	1.420 (3)	C10—H10A	0.9900
N3—C7	1.330 (3)	C10—H10B	0.9900
N3—C6	1.333 (3)	C11—C12	1.170 (4)
N4—C8	1.326 (3)	C12—H12	0.9500
N4—C7	1.334 (3)
C8—O1—C10	117.33 (18)	F3—C4—C1	112.9 (4)
C1—N1—N2	104.57 (19)	F1—C4—C1	112.9 (7)
N1—N2—C3	112.62 (19)	F1'—C4—C1	113.8 (12)
N1—N2—C6	117.62 (18)	F3'—C4—C1	109.1 (8)
C3—N2—C6	129.8 (2)	F2—C4—C1	110.0 (4)
C7—N3—C6	114.7 (2)	C3—C5—H5A	109.5
C8—N4—C7	114.6 (2)	C3—C5—H5B	109.5
N1—C1—C2	111.4 (2)	H5A—C5—H5B	109.5
N1—C1—C4	119.0 (2)	C3—C5—H5C	109.5
C2—C1—C4	129.5 (2)	H5A—C5—H5C	109.5
C3—C2—C1	106.7 (2)	H5B—C5—H5C	109.5
C3—C2—Cl1	125.8 (2)	N3—C6—C9	124.0 (2)
C1—C2—Cl1	127.46 (19)	N3—C6—N2	115.5 (2)
C2—C3—N2	104.7 (2)	C9—C6—N2	120.5 (2)
C2—C3—C5	128.1 (2)	N3—C7—N4	127.9 (2)
N2—C3—C5	127.3 (2)	N3—C7—H7A	116.1
F2'—C4—F3	81.9 (8)	N4—C7—H7A	116.1
F2'—C4—F1	119.3 (10)	N4—C8—O1	119.6 (2)
F3—C4—F1	108.6 (7)	N4—C8—C9	124.1 (2)
F2'—C4—F1'	109.0 (14)	O1—C8—C9	116.3 (2)
F3—C4—F1'	118.7 (11)	C6—C9—C8	114.7 (2)
F1—C4—F1'	14.2 (15)	C6—C9—H9A	122.6
F2'—C4—F3'	104.4 (9)	C8—C9—H9A	122.6
F3—C4—F3'	24.2 (8)	O1—C10—C11	111.7 (2)
F1—C4—F3'	89.7 (10)	O1—C10—H10A	109.3
F1'—C4—F3'	102.3 (13)	C11—C10—H10A	109.3
F2'—C4—F2	25.2 (10)	O1—C10—H10B	109.3
F3—C4—F2	106.6 (5)	C11—C10—H10B	109.3
F1—C4—F2	105.4 (7)	H10A—C10—H10B	107.9
F1'—C4—F2	92.4 (11)	C12—C11—C10	177.0 (3)
F3'—C4—F2	127.7 (7)	C11—C12—H12	180.0
F2'—C4—C1	116.8 (7)
C1—N1—N2—C3	−0.5 (2)	C2—C1—C4—F1'	−49.2 (13)
C1—N1—N2—C6	179.62 (18)	N1—C1—C4—F3'	−112.0 (12)
N2—N1—C1—C2	0.1 (2)	C2—C1—C4—F3'	64.2 (13)
N2—N1—C1—C4	177.0 (2)	N1—C1—C4—F2	32.5 (7)
N1—C1—C2—C3	0.3 (3)	C2—C1—C4—F2	−151.3 (7)
C4—C1—C2—C3	−176.2 (2)	C7—N3—C6—C9	0.6 (3)
N1—C1—C2—Cl1	−179.60 (17)	C7—N3—C6—N2	−179.65 (19)
C4—C1—C2—Cl1	3.9 (4)	N1—N2—C6—N3	−177.90 (19)
C1—C2—C3—N2	−0.6 (2)	C3—N2—C6—N3	2.3 (3)
Cl1—C2—C3—N2	179.31 (16)	N1—N2—C6—C9	1.8 (3)
C1—C2—C3—C5	178.3 (2)	C3—N2—C6—C9	−178.0 (2)
Cl1—C2—C3—C5	−1.8 (4)	C6—N3—C7—N4	−1.0 (4)
N1—N2—C3—C2	0.7 (2)	C8—N4—C7—N3	0.4 (4)
C6—N2—C3—C2	−179.5 (2)	C7—N4—C8—O1	−179.9 (2)
N1—N2—C3—C5	−178.1 (2)	C7—N4—C8—C9	0.6 (3)
C6—N2—C3—C5	1.7 (4)	C10—O1—C8—N4	7.7 (3)
N1—C1—C4—F2'	6.0 (16)	C10—O1—C8—C9	−172.72 (19)
C2—C1—C4—F2'	−177.7 (16)	N3—C6—C9—C8	0.2 (3)
N1—C1—C4—F3	−86.4 (9)	N2—C6—C9—C8	−179.49 (19)
C2—C1—C4—F3	89.9 (9)	N4—C8—C9—C6	−0.9 (3)
N1—C1—C4—F1	150.0 (8)	O1—C8—C9—C6	179.58 (19)
C2—C1—C4—F1	−33.8 (8)	C8—O1—C10—C11	76.9 (3)
N1—C1—C4—F1'	134.5 (13)	O1—C10—C11—C12	149 (6)