4-Chloro-5-[(5,5-dimethyl-4,5-dihydro­isoxazol-3-yl)sulfonyl­meth­yl]-3-methyl-1-(2,2,2-trifluoro­ethyl)-1H-pyrazole

Ma, H.-J.; Zhao, Q.-F.; Mei, X.-D.; Ning, J.

doi:10.1107/S1600536809038471

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2567

doi:10.1107/S1600536809038471

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4-Chloro-5-[(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)sulfonylmethyl]-3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole

Hong-Ju Ma,^a Qian-Fei Zhao,^a Xiang-Dong Mei ^a and Jun Ning ^a ^*

^aKey Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China
^*Correspondence e-mail: jning502@yahoo.com.cn

(Received 14 September 2009; accepted 23 September 2009; online 30 September 2009)

The molecule of the title compound, C₁₂H₁₅ClF₃N₃O₃S, is twisted, as indicated by the C—S—C—C torsion angle of 66.00 (18)° for the atoms linking the ring systems. An intramolecular C—H⋯F short contact occurs. In the crystal, non-classical C—H⋯O interactions, one of which has a short H⋯O contact of 2.28 Å, link the molecules.

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_r = 373.78
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.097
S = 1.09
2891 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) -x+1, -y+1, -z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Pyrazoles are an important class of compounds, which possess widespread pharmacological properties in pharmaceuticals (Sridhar et al., 2004; Zheng et al., 2009; Sabbagh et al., 2009) and agrochemicals (Shiga et al., 2003; Ohno et al., 2004). Various pyrazole derivatives with potent herbicidal activity have been synthesized and some are in use as herbicides such as pyrazolate, pyrazoxyfen, benzofenap, pyraflufen-ethyl, fluazolate and pyrazosulfuron-ethyl (Hirai et al., 2002). Recently, the new title compound (I) was synthesized in our group with high herbicidal activity. The crystal structure of the title compound is shown in Fig. 1.

Related literature top

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 top

The title compound (0.2 g) was dissolved in acetone (50 ml) at room temperature. Colourless blocks of (I) were obtained through slow evaporation after two weeks.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

4-Chloro-5-[(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)sulfonylmethyl]- 3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole top

Crystal data top

C₁₂H₁₅ClF₃N₃O₃S	F(000) = 768
M_r = 373.78	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0203P)² + 1.0073P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2891 reflections	Δρ_max = 0.39 e Å⁻³
212 parameters	Δρ_min = −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)

Crystal data top

C₁₂H₁₅ClF₃N₃O₃S	V = 1590.7 (6) Å³
M_r = 373.78	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 16.034 (3) Å	µ = 3.83 mm⁻¹
b = 5.4319 (11) Å	T = 173 K
c = 19.069 (4) Å	0.39 × 0.26 × 0.25 mm
β = 106.71 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2891 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 2003)	2568 reflections with I > 2σ(I)
T_min = 0.317, T_max = 0.448	R_int = 0.073
11348 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.09	Δρ_max = 0.39 e Å⁻³
2891 reflections	Δρ_min = −0.36 e Å⁻³
212 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅ClF₃N₃O₃S
M_r	373.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	16.034 (3), 5.4319 (11), 19.069 (4)
β (°)	106.71 (3)
V (Å³)	1590.7 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.83
Crystal size (mm)	0.39 × 0.26 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 2003)
T_min, T_max	0.317, 0.448
No. of measured, independent and observed [I > 2σ(I)] reflections	11348, 2891, 2568
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.097, 1.09
No. of reflections	2891
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.36

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y+1, z.

Acknowledgements

This work was supported by the Major State Basic Research Development Program of China (No. 2010CB126106 and No. 2006CB101907), and the 863 high-tech key project of China (2006AA10A203).

References

Higashi, T. (2003). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hirai, K., Uchida, A. & Ohno, R. (2002). Herbicide Classes in Development, edited by P. Boger, K. Hirai & K. Wakabyashi, pp. 179–289. Heidelberg: Springer-Verlag. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sabbagh, O. I., Raraka, M. M., Ibrahim, S. M., Pannecouque, C., Andrei, G., Snoeck, R., Balzarini, J. & Rashad, A. A. (2009). Eur. J. Med. Chem. 44, 3746–3753. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shiga, Y., Okada, I., Ikeda, Y., Takizawa, E. & Fukuchi, T. (2003). J. Pestic. Sci. 28, 313–314. Web of Science CrossRef CAS Google Scholar
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Volume 65| Part 10| October 2009| Page o2567

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Chloro-5-[(5,5-di­methyl-4,5-di­hydro­isoxazol-3-yl)sulfonyl­meth­yl]-3-methyl-1-(2,2,2-tri­fluoro­ethyl)-1H-pyrazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Chloro-5-[(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)sulfonylmethyl]-3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole