1-[2,6-Dichloro-4-(trifluoro-meth-yl)phen-yl]-5-iodo-4-trifluoro-methyl-sulfinyl-1H-pyrazole-3-carbonitrile.

In the title compound, C(12)H(2)Cl(2)F(6)IN(3)OS, the dihedral angle between the planes of the benzene and pyrazole rings is 77.8 (2)°. In the crystal, a short I⋯N contact of 2.897 (5) Å occurs.

Related literature

For related structures containing phenylpyrazole, see: Shi et al. (2009 ▶); Tang, Zhong, Li & Hu (2005 ▶). Tang, Zhong, Lin, Hu & Shi (2005 ▶).

Experimental

Crystal data

C12H2Cl2F6IN3OS

M = 548.03

Monoclinic,

a = 9.5879 (3) Å

b = 13.7798 (4) Å

c = 14.3145 (5) Å

β = 107.400 (3)°

V = 1804.68 (10) Å3

Z = 4

Cu Kα radiation

μ = 18.41 mm−1

T = 100 K

0.45 × 0.27 × 0.19 mm

Data collection

Oxford Diffraction Gemini (Cu) X-ray Ultra diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction 2006 ▶) T min = 0.016, T max = 0.213

8203 measured reflections

3132 independent reflections

3065 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.13

3132 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −1.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025082/bt2972sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025082/bt2972Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

C12H2Cl2F6IN3OS	F(000) = 1040
Mr = 548.03	Dx = 2.017 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3132 reflections
a = 9.5879 (3) Å	θ = 4.6–67.0°
b = 13.7798 (4) Å	µ = 18.41 mm−1
c = 14.3145 (5) Å	T = 100 K
β = 107.400 (3)°	Prism, colorless
V = 1804.68 (10) Å3	0.45 × 0.27 × 0.19 mm
Z = 4

Oxford Diffraction Gemini (Cu) X-ray Ultra diffractometer	3132 independent reflections
Radiation source: fine-focus sealed tube	3065 reflections with I > 2σ(I)
mirror	Rint = 0.041
ω and π scans	θmax = 67.0°, θmin = 4.6°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction 2006)	h = −10→11
Tmin = 0.016, Tmax = 0.213	k = −16→15
8203 measured reflections	l = −17→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0636P)2 + 4.9895P] where P = (Fo2 + 2Fc2)/3
3132 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −1.25 e Å−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
I1	0.32209 (3)	0.65606 (2)	0.31318 (2)	0.02325 (15)
Cl1	0.49232 (14)	0.42087 (8)	0.14823 (9)	0.0336 (3)
Cl2	0.37074 (16)	0.80256 (8)	0.09630 (9)	0.0364 (3)
S1	0.70639 (13)	0.70720 (8)	0.47083 (8)	0.0257 (3)
O1	0.8422 (4)	0.7630 (3)	0.4932 (3)	0.0360 (8)
N1	0.5348 (4)	0.6307 (3)	0.1980 (3)	0.0215 (8)
N2	0.6758 (4)	0.6311 (4)	0.1956 (3)	0.0312 (10)
N3	1.0327 (6)	0.6582 (4)	0.3373 (4)	0.0474 (15)
C1	0.1794 (5)	0.5669 (3)	−0.0465 (3)	0.0238 (10)
C2	0.2659 (5)	0.4911 (3)	0.0021 (3)	0.0230 (9)
H2A	0.2448	0.4273	−0.0183	0.028*
C3	0.3855 (5)	0.5134 (3)	0.0823 (3)	0.0219 (9)
C4	0.4171 (5)	0.6096 (3)	0.1111 (3)	0.0217 (9)
C5	0.3304 (6)	0.6833 (4)	0.0603 (4)	0.0263 (10)
C6	0.2084 (6)	0.6628 (3)	−0.0189 (4)	0.0279 (11)
H6A	0.1480	0.7124	−0.0523	0.034*
C7	0.0517 (6)	0.5443 (4)	−0.1351 (4)	0.0304 (11)
C8	0.5210 (5)	0.6523 (3)	0.2870 (4)	0.0182 (9)
C9	0.6611 (5)	0.6671 (3)	0.3484 (4)	0.0228 (10)
C10	0.7517 (6)	0.6527 (3)	0.2873 (4)	0.0276 (11)
C11	0.9089 (6)	0.6571 (4)	0.3153 (5)	0.0350 (14)
C12	0.7590 (6)	0.5852 (4)	0.5261 (4)	0.0391 (13)
F1	0.0028 (4)	0.4545 (3)	−0.1333 (3)	0.0488 (9)
F2	0.0883 (4)	0.5527 (3)	−0.2176 (2)	0.0439 (8)
F3	−0.0603 (4)	0.6042 (3)	−0.1430 (3)	0.0487 (9)
F4	0.6443 (4)	0.5270 (2)	0.4989 (3)	0.0503 (9)
F5	0.7988 (5)	0.5949 (3)	0.6227 (3)	0.0585 (11)
F6	0.8683 (4)	0.5472 (3)	0.5007 (3)	0.0624 (11)

	U11	U22	U33	U12	U13	U23
I1	0.0165 (2)	0.0296 (2)	0.0220 (2)	−0.00092 (10)	0.00320 (13)	−0.00227 (10)
Cl1	0.0314 (6)	0.0221 (6)	0.0387 (7)	0.0056 (5)	−0.0026 (5)	0.0011 (5)
Cl2	0.0574 (8)	0.0171 (6)	0.0285 (6)	−0.0045 (5)	0.0033 (5)	−0.0014 (4)
S1	0.0264 (6)	0.0222 (6)	0.0230 (6)	−0.0021 (4)	−0.0008 (4)	−0.0002 (4)
O1	0.038 (2)	0.0290 (19)	0.036 (2)	−0.0106 (16)	0.0032 (16)	−0.0038 (16)
N1	0.0142 (18)	0.0247 (19)	0.0225 (19)	−0.0027 (16)	0.0008 (15)	−0.0014 (16)
N2	0.025 (2)	0.034 (2)	0.035 (2)	−0.0073 (17)	0.010 (2)	−0.0099 (19)
N3	0.021 (3)	0.064 (4)	0.058 (3)	−0.011 (2)	0.013 (2)	−0.035 (3)
C1	0.025 (2)	0.024 (2)	0.021 (2)	−0.0014 (19)	0.0050 (19)	−0.0004 (19)
C2	0.024 (2)	0.019 (2)	0.024 (2)	−0.0002 (18)	0.0043 (19)	−0.0038 (18)
C3	0.022 (2)	0.020 (2)	0.023 (2)	−0.0009 (18)	0.0050 (18)	−0.0004 (18)
C4	0.019 (2)	0.023 (2)	0.021 (2)	−0.0055 (18)	0.0039 (18)	−0.0053 (18)
C5	0.040 (3)	0.018 (2)	0.020 (2)	−0.002 (2)	0.007 (2)	−0.0022 (19)
C6	0.034 (3)	0.022 (2)	0.024 (2)	0.0029 (19)	0.002 (2)	0.0020 (18)
C7	0.025 (2)	0.031 (3)	0.030 (3)	0.003 (2)	0.000 (2)	−0.004 (2)
C8	0.010 (2)	0.018 (2)	0.025 (2)	0.0004 (15)	0.0038 (18)	0.0011 (16)
C9	0.021 (2)	0.017 (2)	0.027 (3)	−0.0013 (17)	0.002 (2)	−0.0014 (17)
C10	0.019 (3)	0.027 (3)	0.036 (3)	−0.0075 (18)	0.007 (2)	−0.009 (2)
C11	0.025 (3)	0.038 (3)	0.043 (3)	−0.008 (2)	0.012 (2)	−0.022 (2)
C12	0.034 (3)	0.029 (3)	0.042 (3)	−0.002 (2)	−0.008 (2)	0.009 (2)
F1	0.047 (2)	0.0386 (18)	0.0447 (19)	−0.0169 (16)	−0.0112 (15)	−0.0053 (15)
F2	0.0371 (18)	0.069 (2)	0.0202 (14)	0.0001 (16)	−0.0001 (12)	−0.0055 (15)
F3	0.0321 (17)	0.055 (2)	0.048 (2)	0.0130 (16)	−0.0052 (15)	−0.0163 (16)
F4	0.056 (2)	0.0313 (17)	0.053 (2)	−0.0147 (16)	0.0008 (17)	0.0124 (15)
F5	0.070 (3)	0.054 (2)	0.0337 (18)	−0.0074 (19)	−0.0127 (17)	0.0158 (16)
F6	0.047 (2)	0.049 (2)	0.084 (3)	0.0264 (18)	0.009 (2)	0.021 (2)

I1—C8	2.051 (4)	C2—H2A	0.9300
Cl1—C3	1.728 (5)	C3—C4	1.394 (6)
Cl2—C5	1.731 (5)	C4—C5	1.375 (7)
S1—O1	1.463 (4)	C5—C6	1.392 (7)
S1—C9	1.764 (5)	C6—H6A	0.9300
S1—C12	1.863 (6)	C7—F1	1.327 (6)
N1—C8	1.353 (6)	C7—F3	1.332 (6)
N1—N2	1.363 (6)	C7—F2	1.333 (6)
N1—C4	1.438 (6)	C8—C9	1.382 (7)
N2—C10	1.330 (7)	C9—C10	1.419 (7)
N3—C11	1.134 (8)	C10—C11	1.440 (8)
C1—C2	1.384 (7)	C12—F6	1.316 (8)
C1—C6	1.384 (7)	C12—F4	1.322 (7)
C1—C7	1.508 (6)	C12—F5	1.327 (7)
C2—C3	1.393 (7)
O1—S1—C9	108.7 (2)	C5—C6—H6A	120.8
O1—S1—C12	105.8 (2)	F1—C7—F3	107.4 (4)
C9—S1—C12	95.4 (2)	F1—C7—F2	106.6 (4)
C8—N1—N2	113.6 (4)	F3—C7—F2	106.9 (4)
C8—N1—C4	126.0 (4)	F1—C7—C1	112.2 (4)
N2—N1—C4	120.5 (4)	F3—C7—C1	112.0 (4)
C10—N2—N1	103.3 (4)	F2—C7—C1	111.4 (4)
C2—C1—C6	122.5 (5)	N1—C8—C9	106.3 (4)
C2—C1—C7	118.7 (4)	N1—C8—I1	122.4 (3)
C6—C1—C7	118.7 (5)	C9—C8—I1	131.3 (4)
C1—C2—C3	118.0 (4)	C8—C9—C10	104.2 (4)
C1—C2—H2A	121.0	C8—C9—S1	125.6 (4)
C3—C2—H2A	121.0	C10—C9—S1	129.9 (4)
C2—C3—C4	120.4 (4)	N2—C10—C9	112.6 (5)
C2—C3—Cl1	119.7 (4)	N2—C10—C11	120.1 (5)
C4—C3—Cl1	119.9 (4)	C9—C10—C11	127.2 (5)
C5—C4—C3	120.2 (4)	N3—C11—C10	178.4 (6)
C5—C4—N1	120.1 (4)	F6—C12—F4	109.8 (5)
C3—C4—N1	119.6 (4)	F6—C12—F5	108.9 (5)
C4—C5—C6	120.6 (4)	F4—C12—F5	108.8 (5)
C4—C5—Cl2	119.9 (4)	F6—C12—S1	112.3 (4)
C6—C5—Cl2	119.5 (4)	F4—C12—S1	109.1 (4)
C1—C6—C5	118.3 (5)	F5—C12—S1	107.9 (4)
C1—C6—H6A	120.8
C8—N1—N2—C10	0.7 (6)	C2—C1—C7—F2	−94.0 (5)
C4—N1—N2—C10	−179.8 (4)	C6—C1—C7—F2	83.8 (6)
C6—C1—C2—C3	0.7 (7)	N2—N1—C8—C9	−0.7 (5)
C7—C1—C2—C3	178.4 (4)	C4—N1—C8—C9	179.9 (4)
C1—C2—C3—C4	−0.9 (7)	N2—N1—C8—I1	−179.5 (3)
C1—C2—C3—Cl1	177.4 (4)	C4—N1—C8—I1	1.1 (6)
C2—C3—C4—C5	−0.2 (7)	N1—C8—C9—C10	0.3 (5)
Cl1—C3—C4—C5	−178.5 (4)	I1—C8—C9—C10	178.9 (3)
C2—C3—C4—N1	175.7 (4)	N1—C8—C9—S1	174.4 (3)
Cl1—C3—C4—N1	−2.6 (6)	I1—C8—C9—S1	−6.9 (6)
C8—N1—C4—C5	75.7 (6)	O1—S1—C9—C8	−149.2 (4)
N2—N1—C4—C5	−103.6 (5)	C12—S1—C9—C8	102.1 (4)
C8—N1—C4—C3	−100.2 (6)	O1—S1—C9—C10	23.4 (5)
N2—N1—C4—C3	80.4 (6)	C12—S1—C9—C10	−85.3 (5)
C3—C4—C5—C6	1.6 (7)	N1—N2—C10—C9	−0.5 (6)
N1—C4—C5—C6	−174.3 (5)	N1—N2—C10—C11	178.0 (5)
C3—C4—C5—Cl2	−179.8 (4)	C8—C9—C10—N2	0.2 (6)
N1—C4—C5—Cl2	4.3 (6)	S1—C9—C10—N2	−173.6 (4)
C2—C1—C6—C5	0.7 (8)	C8—C9—C10—C11	−178.3 (5)
C7—C1—C6—C5	−177.1 (5)	S1—C9—C10—C11	7.9 (8)
C4—C5—C6—C1	−1.8 (8)	O1—S1—C12—F6	−50.8 (5)
Cl2—C5—C6—C1	179.6 (4)	C9—S1—C12—F6	60.4 (4)
C2—C1—C7—F1	25.4 (6)	O1—S1—C12—F4	−172.7 (4)
C6—C1—C7—F1	−156.8 (5)	C9—S1—C12—F4	−61.5 (5)
C2—C1—C7—F3	146.3 (5)	O1—S1—C12—F5	69.2 (5)
C6—C1—C7—F3	−35.9 (7)	C9—S1—C12—F5	−179.6 (4)