4-Chloro-5-[(5,5-dimethyl-4,5-dihydro-isoxazol-3-yl)sulfonyl-meth-yl]-3-methyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazole.

The mol-ecule of the title compound, C(12)H(15)ClF(3)N(3)O(3)S, is twisted, as indicated by the C-S-C-C torsion angle of 66.00 (18)° for the atoms linking the ring systems. An intra-molecular C-H⋯F short contact occurs. In the crystal, non-classical C-H⋯O inter-actions, one of which has a short H⋯O contact of 2.28 Å, link the mol-ecules.

Related literature

For background to pyrazoles and their pharmacological and pharmaceutical applications, see: Hirai et al. (2002 ▶); Shiga et al. (2003 ▶); Ohno et al. (2004 ▶); Sabbagh et al. (2009 ▶); Sridhar et al. (2004 ▶); Zheng et al. (2009 ▶).

Experimental

Crystal data

C12H15ClF3N3O3S

M = 373.78

Monoclinic,

a = 16.034 (3) Å

b = 5.4319 (11) Å

c = 19.069 (4) Å

β = 106.71 (3)°

V = 1590.7 (6) Å3

Z = 4

Cu Kα radiation

μ = 3.83 mm−1

T = 173 K

0.39 × 0.26 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: numerical (NUMABS; Higashi, 2003 ▶) T min = 0.317, T max = 0.448

11348 measured reflections

2891 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.09

2891 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.36 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: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038471/hb5103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038471/hb5103Isup2.hkl

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

C12H15ClF3N3O3S	F(000) = 768
Mr = 373.78	Dx = 1.561 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 11348 reflections
a = 16.034 (3) Å	θ = 3.2–68.2°
b = 5.4319 (11) Å	µ = 3.83 mm−1
c = 19.069 (4) Å	T = 173 K
β = 106.71 (3)°	Block, colourless
V = 1590.7 (6) Å3	0.39 × 0.26 × 0.25 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2891 independent reflections
Radiation source: rotating anode	2568 reflections with I > 2σ(I)
graphite	Rint = 0.073
ω scans	θmax = 68.2°, θmin = 3.2°
Absorption correction: numerical (NUMABS; Higashi, 2003)	h = −16→19
Tmin = 0.317, Tmax = 0.448	k = −6→5
11348 measured reflections	l = −22→20

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0203P)2 + 1.0073P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2891 reflections	Δρmax = 0.39 e Å−3
212 parameters	Δρmin = −0.36 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: 0.0054 (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
Cl1	0.44152 (4)	0.93466 (11)	0.09341 (4)	0.03950 (19)
S1	0.36881 (3)	0.46279 (10)	0.24281 (3)	0.02353 (17)
F1	0.10868 (10)	0.5476 (3)	0.06789 (10)	0.0610 (5)
F2	0.05756 (9)	0.1893 (3)	0.03398 (9)	0.0584 (5)
F3	0.09944 (9)	0.4206 (3)	−0.04032 (8)	0.0519 (5)
O1	0.35709 (10)	0.2075 (3)	0.22345 (9)	0.0320 (4)
O2	0.34961 (10)	0.5475 (3)	0.30760 (9)	0.0355 (4)
O3	0.60616 (9)	0.5020 (3)	0.23839 (9)	0.0295 (4)
N1	0.29777 (12)	0.3998 (4)	−0.01380 (10)	0.0308 (5)
N2	0.27450 (11)	0.4064 (3)	0.04952 (10)	0.0252 (4)
N3	0.52262 (11)	0.4070 (3)	0.22312 (10)	0.0273 (4)
C1	0.37126 (13)	0.6956 (4)	0.06043 (13)	0.0286 (5)
C2	0.35682 (14)	0.5758 (5)	−0.00755 (13)	0.0311 (5)
C3	0.31789 (13)	0.5852 (4)	0.09606 (12)	0.0238 (5)
C4	0.39748 (17)	0.6278 (6)	−0.06716 (14)	0.0478 (7)
H4A	0.3737	0.5148	−0.1081	0.072*
H4B	0.4606	0.6049	−0.0486	0.072*
H4C	0.3848	0.7979	−0.0840	0.072*
C5	0.20776 (14)	0.2398 (4)	0.05769 (12)	0.0277 (5)
H5A	0.2192	0.1968	0.1101	0.033*
H5B	0.2102	0.0861	0.0304	0.033*
C6	0.11822 (15)	0.3496 (5)	0.03000 (14)	0.0358 (6)
C7	0.30537 (13)	0.6436 (4)	0.16871 (12)	0.0252 (5)
H7A	0.2431	0.6211	0.1654	0.030*
H7B	0.3197	0.8193	0.1798	0.030*
C8	0.47791 (13)	0.5464 (4)	0.25218 (11)	0.0217 (5)
C9	0.61812 (13)	0.6994 (4)	0.29469 (12)	0.0262 (5)
C10	0.52374 (13)	0.7681 (4)	0.29159 (13)	0.0280 (5)
H10A	0.5161	0.7844	0.3411	0.034*
H10B	0.5045	0.9214	0.2635	0.034*
C11	0.66650 (17)	0.5831 (5)	0.36693 (14)	0.0415 (7)
H11A	0.7212	0.5121	0.3632	0.062*
H11B	0.6306	0.4531	0.3790	0.062*
H11C	0.6791	0.7087	0.4055	0.062*
C12	0.66893 (16)	0.9029 (5)	0.27166 (17)	0.0426 (7)
H12A	0.7249	0.8382	0.2688	0.064*
H12B	0.6791	1.0365	0.3077	0.064*
H12C	0.6357	0.9658	0.2236	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.0318 (3)	0.0362 (4)	0.0491 (4)	−0.0112 (2)	0.0094 (3)	0.0061 (3)
S1	0.0209 (3)	0.0256 (3)	0.0244 (3)	−0.0035 (2)	0.0071 (2)	−0.0022 (2)
F1	0.0316 (8)	0.0694 (12)	0.0759 (13)	0.0110 (8)	0.0057 (8)	−0.0260 (10)
F2	0.0300 (8)	0.0797 (13)	0.0579 (10)	−0.0223 (8)	0.0005 (7)	0.0141 (9)
F3	0.0366 (8)	0.0723 (12)	0.0408 (9)	0.0071 (8)	0.0018 (7)	0.0211 (8)
O1	0.0305 (9)	0.0225 (9)	0.0404 (10)	−0.0064 (7)	0.0060 (7)	−0.0002 (7)
O2	0.0297 (9)	0.0528 (12)	0.0271 (9)	−0.0028 (8)	0.0132 (7)	−0.0060 (8)
O3	0.0204 (8)	0.0306 (9)	0.0379 (10)	−0.0020 (6)	0.0091 (7)	−0.0091 (7)
N1	0.0277 (10)	0.0423 (12)	0.0227 (10)	0.0014 (9)	0.0077 (8)	0.0003 (9)
N2	0.0234 (9)	0.0295 (10)	0.0227 (10)	−0.0022 (8)	0.0066 (8)	0.0004 (8)
N3	0.0219 (9)	0.0281 (10)	0.0308 (10)	−0.0018 (8)	0.0060 (8)	−0.0038 (8)
C1	0.0193 (11)	0.0307 (13)	0.0338 (13)	−0.0010 (9)	0.0047 (9)	0.0068 (10)
C2	0.0226 (11)	0.0424 (14)	0.0279 (13)	0.0016 (10)	0.0068 (10)	0.0081 (10)
C3	0.0207 (10)	0.0237 (11)	0.0262 (12)	0.0025 (8)	0.0053 (9)	0.0014 (9)
C4	0.0345 (14)	0.079 (2)	0.0333 (15)	−0.0023 (14)	0.0147 (11)	0.0113 (14)
C5	0.0269 (11)	0.0280 (12)	0.0261 (12)	−0.0059 (9)	0.0043 (9)	0.0015 (9)
C6	0.0242 (12)	0.0444 (15)	0.0368 (14)	−0.0086 (11)	0.0054 (10)	0.0017 (12)
C7	0.0212 (10)	0.0238 (11)	0.0309 (12)	0.0018 (9)	0.0080 (9)	−0.0027 (9)
C8	0.0198 (10)	0.0211 (11)	0.0231 (11)	0.0010 (8)	0.0043 (9)	−0.0008 (8)
C9	0.0221 (11)	0.0208 (11)	0.0335 (13)	−0.0012 (9)	0.0048 (9)	−0.0038 (9)
C10	0.0221 (11)	0.0248 (12)	0.0365 (13)	−0.0030 (9)	0.0076 (9)	−0.0079 (10)
C11	0.0348 (14)	0.0444 (16)	0.0367 (15)	0.0013 (11)	−0.0034 (11)	−0.0013 (12)
C12	0.0295 (13)	0.0306 (14)	0.070 (2)	−0.0011 (10)	0.0186 (13)	0.0039 (13)

Cl1—C1	1.716 (2)	C4—H4B	0.9800
S1—O2	1.4324 (16)	C4—H4C	0.9800
S1—O1	1.4333 (16)	C5—C6	1.503 (3)
S1—C8	1.766 (2)	C5—H5A	0.9900
S1—C7	1.780 (2)	C5—H5B	0.9900
F1—C6	1.329 (3)	C7—H7A	0.9900
F2—C6	1.324 (3)	C7—H7B	0.9900
F3—C6	1.344 (3)	C8—C10	1.496 (3)
O3—N3	1.386 (2)	C9—C12	1.511 (3)
O3—C9	1.490 (3)	C9—C11	1.511 (3)
N1—C2	1.327 (3)	C9—C10	1.543 (3)
N1—N2	1.363 (2)	C10—H10A	0.9900
N2—C3	1.364 (3)	C10—H10B	0.9900
N2—C5	1.444 (3)	C11—H11A	0.9800
N3—C8	1.274 (3)	C11—H11B	0.9800
C1—C3	1.374 (3)	C11—H11C	0.9800
C1—C2	1.409 (3)	C12—H12A	0.9800
C2—C4	1.491 (3)	C12—H12B	0.9800
C3—C7	1.490 (3)	C12—H12C	0.9800
C4—H4A	0.9800
O2—S1—O1	119.23 (10)	F2—C6—C5	111.2 (2)
O2—S1—C8	106.40 (10)	F1—C6—C5	112.21 (19)
O1—S1—C8	109.12 (10)	F3—C6—C5	112.4 (2)
O2—S1—C7	106.96 (10)	C3—C7—S1	114.93 (15)
O1—S1—C7	109.07 (10)	C3—C7—H7A	108.5
C8—S1—C7	105.17 (10)	S1—C7—H7A	108.5
N3—O3—C9	109.60 (15)	C3—C7—H7B	108.5
C2—N1—N2	105.74 (19)	S1—C7—H7B	108.5
N1—N2—C3	112.16 (18)	H7A—C7—H7B	107.5
N1—N2—C5	118.62 (18)	N3—C8—C10	116.13 (19)
C3—N2—C5	129.16 (19)	N3—C8—S1	117.92 (16)
C8—N3—O3	108.56 (17)	C10—C8—S1	125.96 (16)
C3—C1—C2	107.0 (2)	O3—C9—C12	106.57 (19)
C3—C1—Cl1	125.86 (19)	O3—C9—C11	106.36 (18)
C2—C1—Cl1	127.13 (18)	C12—C9—C11	113.1 (2)
N1—C2—C1	109.9 (2)	O3—C9—C10	103.00 (16)
N1—C2—C4	121.7 (2)	C12—C9—C10	114.63 (19)
C1—C2—C4	128.5 (2)	C11—C9—C10	112.1 (2)
N2—C3—C1	105.2 (2)	C8—C10—C9	99.16 (17)
N2—C3—C7	125.2 (2)	C8—C10—H10A	111.9
C1—C3—C7	129.5 (2)	C9—C10—H10A	111.9
C2—C4—H4A	109.5	C8—C10—H10B	111.9
C2—C4—H4B	109.5	C9—C10—H10B	111.9
H4A—C4—H4B	109.5	H10A—C10—H10B	109.6
C2—C4—H4C	109.5	C9—C11—H11A	109.5
H4A—C4—H4C	109.5	C9—C11—H11B	109.5
H4B—C4—H4C	109.5	H11A—C11—H11B	109.5
N2—C5—C6	112.07 (19)	C9—C11—H11C	109.5
N2—C5—H5A	109.2	H11A—C11—H11C	109.5
C6—C5—H5A	109.2	H11B—C11—H11C	109.5
N2—C5—H5B	109.2	C9—C12—H12A	109.5
C6—C5—H5B	109.2	C9—C12—H12B	109.5
H5A—C5—H5B	107.9	H12A—C12—H12B	109.5
F2—C6—F1	107.5 (2)	C9—C12—H12C	109.5
F2—C6—F3	106.76 (19)	H12A—C12—H12C	109.5
F1—C6—F3	106.4 (2)	H12B—C12—H12C	109.5
C2—N1—N2—C3	0.1 (2)	N2—C3—C7—S1	86.0 (2)
C2—N1—N2—C5	177.64 (19)	C1—C3—C7—S1	−95.8 (3)
C9—O3—N3—C8	11.2 (2)	O2—S1—C7—C3	178.87 (16)
N2—N1—C2—C1	0.0 (2)	O1—S1—C7—C3	−50.91 (19)
N2—N1—C2—C4	−179.3 (2)	C8—S1—C7—C3	66.00 (18)
C3—C1—C2—N1	−0.2 (3)	O3—N3—C8—C10	1.4 (3)
Cl1—C1—C2—N1	180.00 (17)	O3—N3—C8—S1	−178.52 (13)
C3—C1—C2—C4	179.0 (2)	O2—S1—C8—N3	148.32 (18)
Cl1—C1—C2—C4	−0.8 (4)	O1—S1—C8—N3	18.5 (2)
N1—N2—C3—C1	−0.2 (2)	C7—S1—C8—N3	−98.41 (19)
C5—N2—C3—C1	−177.4 (2)	O2—S1—C8—C10	−31.6 (2)
N1—N2—C3—C7	178.34 (19)	O1—S1—C8—C10	−161.43 (18)
C5—N2—C3—C7	1.2 (3)	C7—S1—C8—C10	81.7 (2)
C2—C1—C3—N2	0.2 (2)	N3—O3—C9—C12	−139.32 (18)
Cl1—C1—C3—N2	−179.92 (16)	N3—O3—C9—C11	99.8 (2)
C2—C1—C3—C7	−178.3 (2)	N3—O3—C9—C10	−18.3 (2)
Cl1—C1—C3—C7	1.6 (3)	N3—C8—C10—C9	−12.4 (3)
N1—N2—C5—C6	−89.8 (2)	S1—C8—C10—C9	167.48 (16)
C3—N2—C5—C6	87.3 (3)	O3—C9—C10—C8	17.0 (2)
N2—C5—C6—F2	176.34 (19)	C12—C9—C10—C8	132.3 (2)
N2—C5—C6—F1	−63.3 (3)	C11—C9—C10—C8	−96.9 (2)
N2—C5—C6—F3	56.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···F1	0.99	2.44	3.229 (3)	136
C4—H4A···O3i	0.98	2.60	3.325 (3)	131
C5—H5A···O2ii	0.99	2.31	3.146 (3)	141
C7—H7B···O1iii	0.99	2.28	3.265 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯F1	0.99	2.44	3.229 (3)	136
C4—H4A⋯O3i	0.98	2.60	3.325 (3)	131
C5—H5A⋯O2ii	0.99	2.31	3.146 (3)	141
C7—H7B⋯O1iii	0.99	2.28	3.265 (3)	171

Symmetry codes: (i) ; (ii) ; (iii) .