5-(3,5-Di-fluoro-phen-yl)-1-(4-fluoro-phen-yl)-3-tri-fluoro-methyl-1H-pyrazole.

In the title compound, C16H8F6N2, the dihedral angle between the pyrazole and di-fluoro-benzene rings is 50.30 (13)°, while those between the pyrazole and fluoro-benzene rings and between the di-fluoro-benzene and fluoro-benzene rings are 38.56 (13) and 53.50 (11)°, respectively. Aromatic π-π stacking inter-actions between adjacent di-fluoro-benzene rings [centroid-centroid separation = 3.6082 (11) Å] link the mol-ecules into dimers parallel to [21-2].

Related literature

For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999 ▶). For a similar structure, see: Sreenivasa et al. (2013 ▶).

Experimental

Crystal data

C16H8F6N2

M = 342.24

Triclinic,

a = 7.2535 (3) Å

b = 8.6686 (4) Å

c = 11.7690 (5) Å

α = 70.909 (1)°

β = 80.139 (1)°

γ = 88.077 (1)°

V = 688.78 (5) Å3

Z = 2

Cu Kα radiation

μ = 1.39 mm−1

T = 293 K

0.39 × 0.35 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.611, T max = 0.669

7069 measured reflections

2181 independent reflections

2040 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.181

S = 1.11

2181 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813032650/wm2788sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032650/wm2788Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032650/wm2788Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H8F6N2	F(000) = 344
Mr = 342.24	Prism
Triclinic, P1	Dx = 1.650 Mg m−3
Hall symbol: -P 1	Melting point: 456 K
a = 7.2535 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.6686 (4) Å	Cell parameters from 1234 reflections
c = 11.7690 (5) Å	θ = 4.0–64.8°
α = 70.909 (1)°	µ = 1.39 mm−1
β = 80.139 (1)°	T = 293 K
γ = 88.077 (1)°	Prism, yellow
V = 688.78 (5) Å3	0.39 × 0.35 × 0.29 mm
Z = 2

Bruker APEXII CCD diffractometer	2181 independent reflections
Radiation source: fine-focus sealed tube	2040 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 64.8°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.611, Tmax = 0.669	k = −9→10
7069 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1212P)2 + 0.5142P] where P = (Fo2 + 2Fc2)/3
2181 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F5	0.4695 (2)	0.16122 (18)	0.61518 (14)	0.0259 (4)
F4	0.0082 (2)	0.5540 (2)	0.60896 (14)	0.0277 (4)
F3	0.8754 (2)	1.09529 (19)	0.57955 (14)	0.0311 (4)
F2	0.8448 (2)	1.0637 (2)	0.77056 (15)	0.0338 (5)
F6	0.7353 (3)	−0.0365 (2)	1.12881 (15)	0.0368 (5)
F1	1.0813 (2)	0.9640 (2)	0.68380 (16)	0.0329 (5)
N2	0.7064 (3)	0.5860 (3)	0.80633 (18)	0.0181 (5)
C8	0.7111 (3)	0.4265 (3)	0.8934 (2)	0.0178 (6)
C2	0.5326 (3)	0.3904 (3)	0.6683 (2)	0.0186 (6)
H2	0.6510	0.3520	0.6815	0.022*
C10	0.5548 (4)	0.1787 (3)	1.0287 (2)	0.0231 (6)
H10	0.4464	0.1152	1.0651	0.028*
C7	0.6008 (3)	0.6408 (3)	0.7159 (2)	0.0178 (5)
C3	0.4110 (4)	0.3037 (3)	0.6324 (2)	0.0188 (5)
C14	0.7893 (3)	0.8337 (3)	0.7149 (2)	0.0191 (6)
C4	0.2343 (3)	0.3540 (3)	0.6116 (2)	0.0196 (6)
H4	0.1552	0.2928	0.5875	0.024*
C5	0.1808 (3)	0.5007 (3)	0.6286 (2)	0.0196 (6)
N1	0.8244 (3)	0.7042 (3)	0.80627 (19)	0.0197 (5)
C16	0.8973 (3)	0.9877 (3)	0.6872 (2)	0.0222 (6)
C11	0.7271 (4)	0.1186 (3)	1.0535 (2)	0.0252 (6)
C6	0.2943 (3)	0.5943 (3)	0.6650 (2)	0.0191 (6)
H6	0.2529	0.6918	0.6763	0.023*
C1	0.4720 (3)	0.5386 (3)	0.6844 (2)	0.0174 (5)
C13	0.8827 (4)	0.3653 (3)	0.9218 (2)	0.0230 (6)
H13	0.9914	0.4288	0.8860	0.028*
C15	0.6500 (3)	0.8044 (3)	0.6551 (2)	0.0187 (6)
H15	0.6018	0.8771	0.5902	0.022*
C9	0.5463 (3)	0.3358 (3)	0.9483 (2)	0.0207 (6)
H9	0.4315	0.3799	0.9314	0.025*
C12	0.8922 (4)	0.2094 (4)	1.0036 (2)	0.0276 (6)
H12	1.0060	0.1672	1.0243	0.033*

	U11	U22	U33	U12	U13	U23
F5	0.0287 (8)	0.0245 (8)	0.0340 (9)	0.0044 (6)	−0.0110 (6)	−0.0196 (7)
F4	0.0148 (7)	0.0429 (10)	0.0349 (9)	0.0067 (6)	−0.0103 (6)	−0.0230 (8)
F3	0.0322 (9)	0.0291 (9)	0.0316 (9)	−0.0068 (7)	−0.0084 (7)	−0.0073 (7)
F2	0.0414 (10)	0.0309 (9)	0.0371 (10)	−0.0063 (7)	−0.0009 (7)	−0.0241 (8)
F6	0.0465 (10)	0.0285 (10)	0.0311 (9)	−0.0012 (8)	−0.0096 (8)	−0.0021 (7)
F1	0.0195 (8)	0.0299 (9)	0.0533 (11)	−0.0036 (6)	−0.0088 (7)	−0.0169 (8)
N2	0.0154 (10)	0.0240 (12)	0.0198 (11)	−0.0024 (8)	−0.0037 (8)	−0.0131 (9)
C8	0.0225 (12)	0.0211 (13)	0.0150 (11)	−0.0015 (10)	−0.0050 (9)	−0.0116 (10)
C2	0.0149 (11)	0.0263 (14)	0.0191 (12)	0.0019 (10)	−0.0053 (9)	−0.0125 (10)
C10	0.0284 (13)	0.0241 (14)	0.0184 (13)	−0.0058 (10)	0.0013 (10)	−0.0113 (11)
C7	0.0135 (11)	0.0257 (13)	0.0197 (12)	0.0001 (9)	−0.0044 (9)	−0.0140 (10)
C3	0.0215 (12)	0.0192 (12)	0.0195 (12)	0.0013 (9)	−0.0033 (9)	−0.0116 (10)
C14	0.0180 (12)	0.0240 (13)	0.0197 (12)	−0.0010 (10)	−0.0027 (9)	−0.0135 (11)
C4	0.0178 (12)	0.0267 (14)	0.0180 (12)	−0.0040 (10)	−0.0036 (9)	−0.0114 (10)
C5	0.0115 (11)	0.0315 (14)	0.0173 (12)	0.0010 (10)	−0.0032 (9)	−0.0098 (10)
N1	0.0175 (10)	0.0232 (12)	0.0227 (11)	−0.0031 (8)	−0.0043 (8)	−0.0127 (9)
C16	0.0202 (12)	0.0267 (14)	0.0246 (14)	0.0011 (10)	−0.0054 (10)	−0.0140 (11)
C11	0.0373 (16)	0.0224 (14)	0.0167 (12)	0.0003 (11)	−0.0061 (11)	−0.0067 (10)
C6	0.0182 (12)	0.0235 (13)	0.0194 (12)	0.0025 (10)	−0.0047 (9)	−0.0116 (10)
C1	0.0157 (11)	0.0241 (13)	0.0159 (12)	−0.0018 (9)	−0.0030 (9)	−0.0108 (10)
C13	0.0214 (13)	0.0283 (14)	0.0219 (13)	−0.0032 (10)	−0.0057 (10)	−0.0103 (11)
C15	0.0182 (12)	0.0215 (13)	0.0208 (12)	0.0022 (10)	−0.0059 (9)	−0.0116 (10)
C9	0.0180 (12)	0.0303 (14)	0.0192 (12)	0.0001 (10)	−0.0018 (9)	−0.0157 (11)
C12	0.0278 (14)	0.0321 (15)	0.0258 (14)	0.0027 (11)	−0.0109 (11)	−0.0105 (12)

F5—C3	1.359 (3)	C7—C15	1.390 (4)
F4—C5	1.351 (3)	C7—C1	1.478 (3)
F3—C16	1.336 (3)	C3—C4	1.376 (4)
F2—C16	1.349 (3)	C14—N1	1.329 (3)
F6—C11	1.353 (3)	C14—C15	1.399 (3)
F1—C16	1.339 (3)	C14—C16	1.483 (3)
N2—N1	1.357 (3)	C4—C5	1.383 (4)
N2—C7	1.367 (3)	C4—H4	0.9300
N2—C8	1.430 (3)	C5—C6	1.383 (3)
C8—C13	1.388 (4)	C11—C12	1.385 (4)
C8—C9	1.390 (4)	C6—C1	1.390 (3)
C2—C3	1.378 (3)	C6—H6	0.9300
C2—C1	1.404 (4)	C13—C12	1.387 (4)
C2—H2	0.9300	C13—H13	0.9300
C10—C11	1.378 (4)	C15—H15	0.9300
C10—C9	1.387 (4)	C9—H9	0.9300
C10—H10	0.9300	C12—H12	0.9300
N1—N2—C7	112.0 (2)	F3—C16—F1	107.1 (2)
N1—N2—C8	118.73 (19)	F3—C16—F2	106.1 (2)
C7—N2—C8	129.3 (2)	F1—C16—F2	106.02 (19)
C13—C8—C9	121.0 (2)	F3—C16—C14	111.8 (2)
C13—C8—N2	118.7 (2)	F1—C16—C14	112.6 (2)
C9—C8—N2	120.3 (2)	F2—C16—C14	112.7 (2)
C3—C2—C1	117.9 (2)	F6—C11—C10	118.5 (2)
C3—C2—H2	121.1	F6—C11—C12	118.7 (2)
C1—C2—H2	121.1	C10—C11—C12	122.8 (3)
C11—C10—C9	118.7 (2)	C5—C6—C1	118.2 (2)
C11—C10—H10	120.6	C5—C6—H6	120.9
C9—C10—H10	120.6	C1—C6—H6	120.9
N2—C7—C15	106.9 (2)	C6—C1—C2	120.5 (2)
N2—C7—C1	125.3 (2)	C6—C1—C7	119.4 (2)
C15—C7—C1	127.6 (2)	C2—C1—C7	120.0 (2)
F5—C3—C4	118.0 (2)	C12—C13—C8	120.0 (2)
F5—C3—C2	118.2 (2)	C12—C13—H13	120.0
C4—C3—C2	123.8 (2)	C8—C13—H13	120.0
N1—C14—C15	113.4 (2)	C7—C15—C14	103.6 (2)
N1—C14—C16	118.8 (2)	C7—C15—H15	128.2
C15—C14—C16	127.8 (2)	C14—C15—H15	128.2
C3—C4—C5	116.2 (2)	C10—C9—C8	119.3 (2)
C3—C4—H4	121.9	C10—C9—H9	120.3
C5—C4—H4	121.9	C8—C9—H9	120.3
F4—C5—C4	117.9 (2)	C11—C12—C13	118.0 (2)
F4—C5—C6	118.7 (2)	C11—C12—H12	121.0
C4—C5—C6	123.4 (2)	C13—C12—H12	121.0
C14—N1—N2	104.07 (19)
N1—N2—C8—C13	−37.8 (3)	C9—C10—C11—F6	−177.9 (2)
C7—N2—C8—C13	139.9 (2)	C9—C10—C11—C12	1.4 (4)
N1—N2—C8—C9	142.0 (2)	F4—C5—C6—C1	−179.7 (2)
C7—N2—C8—C9	−40.3 (3)	C4—C5—C6—C1	0.7 (4)
N1—N2—C7—C15	−1.2 (3)	C5—C6—C1—C2	−0.6 (4)
C8—N2—C7—C15	−179.0 (2)	C5—C6—C1—C7	176.2 (2)
N1—N2—C7—C1	174.1 (2)	C3—C2—C1—C6	0.3 (4)
C8—N2—C7—C1	−3.7 (4)	C3—C2—C1—C7	−176.5 (2)
C1—C2—C3—F5	179.2 (2)	N2—C7—C1—C6	134.5 (2)
C1—C2—C3—C4	0.0 (4)	C15—C7—C1—C6	−51.2 (3)
F5—C3—C4—C5	−179.2 (2)	N2—C7—C1—C2	−48.6 (3)
C2—C3—C4—C5	0.0 (4)	C15—C7—C1—C2	125.7 (3)
C3—C4—C5—F4	180.0 (2)	C9—C8—C13—C12	1.8 (4)
C3—C4—C5—C6	−0.4 (4)	N2—C8—C13—C12	−178.4 (2)
C15—C14—N1—N2	0.5 (3)	N2—C7—C15—C14	1.4 (2)
C16—C14—N1—N2	−179.3 (2)	C1—C7—C15—C14	−173.8 (2)
C7—N2—N1—C14	0.5 (2)	N1—C14—C15—C7	−1.2 (3)
C8—N2—N1—C14	178.55 (19)	C16—C14—C15—C7	178.5 (2)
N1—C14—C16—F3	167.2 (2)	C11—C10—C9—C8	1.3 (3)
C15—C14—C16—F3	−12.5 (3)	C13—C8—C9—C10	−2.9 (3)
N1—C14—C16—F1	46.5 (3)	N2—C8—C9—C10	177.3 (2)
C15—C14—C16—F1	−133.1 (3)	F6—C11—C12—C13	176.8 (2)
N1—C14—C16—F2	−73.3 (3)	C10—C11—C12—C13	−2.4 (4)
C15—C14—C16—F2	107.0 (3)	C8—C13—C12—C11	0.8 (4)