(E)-1-Methyl-5-(3-methyl-4-chloro­phen­oxy)-3-trifluoro­meth­yl-1H-pyrazole-4-carbaldehyde O-acetyl­oxime

Dai, H.; Shen, Y.-F.; Chen, J.; Chen, H.-L.; Shen, Y.-J.

doi:10.1107/S1600536811006696

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o726

doi:10.1107/S1600536811006696

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(E)-1-Methyl-5-(3-methyl-4-chlorophenoxy)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-acetyloxime

Hong Dai,^a Yan-Fei Shen,^a Jiao Chen,^a Hong-Lian Chen ^a and Yong-Jun Shen ^a ^*

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China
^*Correspondence e-mail: gaofz2005@yahoo.com.cn

(Received 16 February 2011; accepted 22 February 2011; online 26 February 2011)

In the title molecule, C₁₅H₁₃ClF₃N₃O₃, the pyrazole and benzene rings form a dihedral angle of 77.6 (3)°. In the crystal, molecules related by translation along the a axis are linked into chains via C—H⋯O hydrogen bonds. The crystal packing is stabilized further by weak π–π [centroid–centroid distance = 3.734 (6) Å] and dipole–dipole interactions [C⋯O = 3.174 (2) Å].

Related literature

For the bioactivity of pyrazole derivatives, see: Hagiwara & Suzuki (1996 ); Ranatunge et al. (2004 ). For related structures, see: Fu et al. (2008 ); Li et al. (2006 ). For the biological activity of compounds containing an oxime ester fragment, see: Vonhoff et al. (1999 ); Wood et al. (1997 ).

Experimental

Crystal data

C₁₅H₁₃ClF₃N₃O₃
M_r = 375.73
Orthorhombic, P b c n
a = 11.951 (2) Å
b = 19.549 (4) Å
c = 13.726 (3) Å
V = 3206.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 113 K
0.16 × 0.12 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.955, T_max = 0.977
21575 measured reflections
3686 independent reflections
3208 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.115
S = 1.10
3686 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O3ⁱ	0.96	2.55	3.102 (2)	117
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006696/cv5055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006696/cv5055Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives have been paid much attention due to their diverse biological activities. Some of them are used as fungicide, insecticide, and antitumor agents (Hagiwara & Suzuki, 1996; Ranatunge et al., 2004). Several studies have recently reported the crystal structures of related pyrazole compounds (Li et al., 2006; Fu et al., 2008). On the other hand, oxime ester group as an efficient pharmacophore was widely used in the field of agricultural and medicinal chemistry (Wood et al. , 1997; Vonhoff et al., 1999). Motivated by the above observations and in continuation of research on the bioactivities of pyrazole derivatives, we synthesized the title compound (I).

In (I) (Fig. 1), the dihedral angle between the planes of the phenyl ring and the pyrazoe ring is 77.6 (3)°. In the crystal structure, the molecules related by translation along axis a are linked into chains via C—H···O hydrogen bonds (Table 2; Fig. 2). The crystal packing is stabilized further by the weak π—π and dipole-dipole interactions (Table 1).

Related literature top

For the bioactivity of pyrazole derivatives, see: Hagiwara & Suzuki (1996); Ranatunge et al. (2004). For related structures, see: Fu et al. (2008); Li et al. (2006). For the biological activity of compounds containing an oxime ester fragment, see: Vonhoff et al. (1999); Wood et al. (1997).

Experimental top

To a stirred solution of 1-methyl-3-(trifluoromethyl)-5-phenoxy-1H- pyrazole-4-carbaldehyde oxime (8 mmol),and sodium bicarbonate (20 mmol) in 80 ml of chloroform, was added dropwise acetyl chloride(10 mmol) at room temperature. The reaction mixture was heated to reflux for 8 h. After cooling to room temperature, the mixture was washed with water (3 * 10 ml) and then with saturated brine (3 * 20 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from petroleum ether/ethyl acetate (8:1 v/v) to obtain colourless crystals.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A portion of the crystal packing of (I). Hydrogen bonds drawn as dashed lines.

(E)-1-Methyl-5-(3-methyl-4-chlorophenoxy)-3-trifluoromethyl- 1H-pyrazole-4-carbaldehyde O-acetyloxime top

Crystal data top

C₁₅H₁₃ClF₃N₃O₃	F(000) = 1536
M_r = 375.73	D_x = 1.557 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7040 reflections
a = 11.951 (2) Å	θ = 2.0–27.5°
b = 19.549 (4) Å	µ = 0.29 mm⁻¹
c = 13.726 (3) Å	T = 113 K
V = 3206.8 (11) Å³	Orthorhombic, colourless
Z = 8	0.16 × 0.12 × 0.08 mm

Data collection top

Rigaku Saturn diffractometer	3686 independent reflections
Radiation source: rotating anode	3208 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.061
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −12→15
T_min = 0.955, T_max = 0.977	k = −25→24
21575 measured reflections	l = −14→17

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0516P)² + 1.0705P] where P = (F_o² + 2F_c²)/3
3686 reflections	(Δ/σ)_max = 0.005
229 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₅H₁₃ClF₃N₃O₃	V = 3206.8 (11) Å³
M_r = 375.73	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 11.951 (2) Å	µ = 0.29 mm⁻¹
b = 19.549 (4) Å	T = 113 K
c = 13.726 (3) Å	0.16 × 0.12 × 0.08 mm

Data collection top

Rigaku Saturn diffractometer	3686 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	3208 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.977	R_int = 0.061
21575 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.10	Δρ_max = 0.29 e Å⁻³
3686 reflections	Δρ_min = −0.33 e Å⁻³
229 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	0.78669 (4)	1.02584 (3)	1.15028 (4)	0.03467 (15)
F1	1.04265 (9)	0.54780 (6)	0.90733 (11)	0.0422 (3)
F2	0.89699 (11)	0.56763 (6)	0.82078 (10)	0.0429 (3)
F3	0.88936 (10)	0.57911 (6)	0.97538 (10)	0.0415 (3)
O1	0.97587 (11)	0.84054 (6)	0.85735 (9)	0.0258 (3)
O2	0.62455 (10)	0.75817 (7)	0.87263 (9)	0.0254 (3)
O3	0.45722 (10)	0.80203 (7)	0.86552 (10)	0.0311 (3)
N1	1.09611 (12)	0.67936 (8)	0.88946 (11)	0.0254 (3)
N2	1.09519 (12)	0.74822 (8)	0.88089 (11)	0.0236 (3)
N3	0.74122 (12)	0.77434 (8)	0.87076 (11)	0.0233 (3)
C1	0.95593 (15)	0.58904 (10)	0.89804 (14)	0.0282 (4)
C2	0.98845 (14)	0.66220 (9)	0.88872 (13)	0.0221 (4)
C3	0.91641 (14)	0.71893 (9)	0.87938 (12)	0.0216 (4)
C4	0.99049 (14)	0.77333 (9)	0.87439 (12)	0.0214 (4)
C5	1.19918 (15)	0.78688 (11)	0.87754 (15)	0.0302 (4)
H5A	1.2122	0.8025	0.8122	0.045*
H5B	1.2600	0.7581	0.8978	0.045*
H5C	1.1939	0.8255	0.9204	0.045*
C6	0.93017 (13)	0.88174 (9)	0.93094 (12)	0.0204 (3)
C7	0.89984 (14)	0.94648 (9)	0.90188 (13)	0.0240 (4)
H7	0.9087	0.9602	0.8375	0.029*
C8	0.85584 (14)	0.99074 (9)	0.97051 (14)	0.0252 (4)
H8	0.8353	1.0349	0.9529	0.030*
C9	0.84251 (14)	0.96877 (9)	1.06574 (13)	0.0231 (4)
C10	0.87284 (13)	0.90360 (9)	1.09597 (13)	0.0217 (4)
C11	0.91814 (13)	0.85973 (9)	1.02608 (13)	0.0215 (4)
H11	0.9402	0.8158	1.0435	0.026*
C12	0.85611 (16)	0.87976 (10)	1.19861 (14)	0.0293 (4)
H12A	0.8918	0.9111	1.2426	0.044*
H12B	0.8882	0.8351	1.2063	0.044*
H12C	0.7775	0.8778	1.2128	0.044*
C13	0.79576 (14)	0.71860 (9)	0.87804 (13)	0.0227 (4)
H13	0.7574	0.6773	0.8825	0.027*
C14	0.55571 (14)	0.81436 (10)	0.86479 (13)	0.0246 (4)
C15	0.60736 (15)	0.88311 (10)	0.85610 (16)	0.0309 (4)
H15A	0.5496	0.9172	0.8527	0.046*
H15B	0.6522	0.8850	0.7981	0.046*
H15C	0.6537	0.8916	0.9119	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0395 (3)	0.0301 (3)	0.0343 (3)	0.00681 (19)	−0.00035 (19)	−0.0103 (2)
F1	0.0363 (6)	0.0256 (6)	0.0646 (9)	0.0072 (5)	−0.0057 (6)	0.0028 (6)
F2	0.0556 (8)	0.0291 (7)	0.0440 (7)	−0.0061 (5)	−0.0190 (6)	−0.0062 (6)
F3	0.0475 (7)	0.0326 (7)	0.0446 (8)	−0.0076 (5)	0.0115 (6)	0.0049 (6)
O1	0.0355 (7)	0.0212 (7)	0.0206 (6)	0.0024 (5)	0.0072 (5)	0.0023 (5)
O2	0.0190 (6)	0.0244 (7)	0.0328 (7)	−0.0022 (5)	0.0000 (5)	0.0013 (6)
O3	0.0209 (6)	0.0340 (8)	0.0382 (8)	−0.0022 (5)	0.0028 (5)	0.0006 (6)
N1	0.0260 (8)	0.0245 (8)	0.0259 (8)	0.0014 (6)	−0.0005 (6)	−0.0024 (6)
N2	0.0237 (7)	0.0239 (8)	0.0232 (8)	−0.0007 (6)	0.0008 (6)	−0.0026 (6)
N3	0.0172 (7)	0.0284 (8)	0.0243 (8)	−0.0022 (6)	−0.0002 (6)	0.0002 (6)
C1	0.0285 (9)	0.0261 (10)	0.0300 (10)	0.0009 (7)	−0.0038 (8)	−0.0008 (8)
C2	0.0228 (8)	0.0224 (9)	0.0211 (9)	0.0010 (7)	−0.0004 (7)	−0.0019 (7)
C3	0.0230 (8)	0.0234 (9)	0.0183 (8)	0.0011 (7)	−0.0002 (6)	−0.0025 (7)
C4	0.0255 (8)	0.0230 (9)	0.0158 (8)	0.0026 (7)	0.0017 (6)	−0.0015 (7)
C5	0.0261 (9)	0.0350 (11)	0.0295 (10)	−0.0078 (8)	0.0024 (7)	−0.0038 (8)
C6	0.0194 (7)	0.0210 (9)	0.0208 (8)	−0.0014 (6)	0.0006 (6)	−0.0018 (7)
C7	0.0242 (8)	0.0247 (9)	0.0231 (9)	−0.0015 (7)	−0.0013 (7)	0.0052 (7)
C8	0.0240 (8)	0.0195 (9)	0.0321 (10)	0.0019 (7)	−0.0046 (7)	0.0011 (8)
C9	0.0207 (8)	0.0228 (9)	0.0258 (9)	−0.0004 (6)	−0.0006 (7)	−0.0054 (7)
C10	0.0183 (7)	0.0249 (9)	0.0219 (9)	−0.0030 (6)	−0.0015 (6)	−0.0003 (7)
C11	0.0216 (8)	0.0198 (8)	0.0230 (9)	−0.0002 (7)	−0.0004 (7)	0.0007 (7)
C12	0.0318 (9)	0.0332 (11)	0.0230 (9)	0.0005 (8)	0.0019 (7)	−0.0009 (8)
C13	0.0244 (8)	0.0231 (9)	0.0206 (8)	−0.0027 (7)	−0.0002 (6)	0.0000 (7)
C14	0.0237 (9)	0.0285 (10)	0.0216 (9)	0.0012 (7)	0.0019 (7)	−0.0009 (7)
C15	0.0253 (9)	0.0240 (10)	0.0436 (12)	0.0007 (7)	0.0045 (8)	−0.0007 (9)

Geometric parameters (Å, º) top

Cl1—C9	1.7425 (18)	C5—H5C	0.9600
F1—C1	1.319 (2)	C6—C7	1.376 (2)
F2—C1	1.340 (2)	C6—C11	1.382 (2)
F3—C1	1.341 (2)	C7—C8	1.383 (3)
O1—C4	1.346 (2)	C7—H7	0.9300
O1—C6	1.403 (2)	C8—C9	1.385 (3)
O2—C14	1.377 (2)	C8—H8	0.9300
O2—N3	1.4299 (18)	C9—C10	1.388 (3)
O3—C14	1.201 (2)	C10—C11	1.396 (2)
N1—C2	1.330 (2)	C10—C12	1.497 (2)
N1—N2	1.351 (2)	C11—H11	0.9300
N2—C4	1.347 (2)	C12—H12A	0.9600
N2—C5	1.455 (2)	C12—H12B	0.9600
N3—C13	1.274 (2)	C12—H12C	0.9600
C1—C2	1.488 (3)	C13—H13	0.9300
C2—C3	1.410 (2)	C14—C15	1.484 (3)
C3—C4	1.385 (3)	C15—H15A	0.9600
C3—C13	1.442 (2)	C15—H15B	0.9600
C5—H5A	0.9600	C15—H15C	0.9600
C5—H5B	0.9600

C14···O3ⁱ	3.174 (2)	Cg···Cgⁱⁱ	3.734 (6)

C4—O1—C6	119.07 (13)	C6—C7—H7	120.7
C14—O2—N3	113.89 (13)	C8—C7—H7	120.7
C2—N1—N2	104.05 (14)	C7—C8—C9	119.51 (17)
C4—N2—N1	112.11 (14)	C7—C8—H8	120.2
C4—N2—C5	127.00 (16)	C9—C8—H8	120.2
N1—N2—C5	120.88 (15)	C8—C9—C10	122.46 (17)
C13—N3—O2	107.97 (14)	C8—C9—Cl1	118.29 (14)
F1—C1—F2	107.37 (16)	C10—C9—Cl1	119.25 (14)
F1—C1—F3	107.53 (16)	C9—C10—C11	117.37 (16)
F2—C1—F3	105.63 (15)	C9—C10—C12	122.14 (16)
F1—C1—C2	112.99 (15)	C11—C10—C12	120.48 (16)
F2—C1—C2	111.69 (16)	C6—C11—C10	119.89 (16)
F3—C1—C2	111.24 (16)	C6—C11—H11	120.1
N1—C2—C3	113.16 (16)	C10—C11—H11	120.1
N1—C2—C1	119.65 (15)	C10—C12—H12A	109.5
C3—C2—C1	127.19 (16)	C10—C12—H12B	109.5
C4—C3—C2	102.59 (15)	H12A—C12—H12B	109.5
C4—C3—C13	129.93 (17)	C10—C12—H12C	109.5
C2—C3—C13	127.47 (17)	H12A—C12—H12C	109.5
O1—C4—N2	119.20 (16)	H12B—C12—H12C	109.5
O1—C4—C3	132.45 (16)	N3—C13—C3	120.59 (17)
N2—C4—C3	108.10 (16)	N3—C13—H13	119.7
N2—C5—H5A	109.5	C3—C13—H13	119.7
N2—C5—H5B	109.5	O3—C14—O2	115.13 (17)
H5A—C5—H5B	109.5	O3—C14—C15	126.16 (18)
N2—C5—H5C	109.5	O2—C14—C15	118.71 (15)
H5A—C5—H5C	109.5	C14—C15—H15A	109.5
H5B—C5—H5C	109.5	C14—C15—H15B	109.5
C7—C6—C11	122.19 (16)	H15A—C15—H15B	109.5
C7—C6—O1	114.96 (15)	C14—C15—H15C	109.5
C11—C6—O1	122.83 (15)	H15A—C15—H15C	109.5
C6—C7—C8	118.57 (17)	H15B—C15—H15C	109.5

C2—N1—N2—C4	−0.38 (19)	C2—C3—C4—N2	−0.22 (18)
C2—N1—N2—C5	−179.17 (16)	C13—C3—C4—N2	178.40 (17)
C14—O2—N3—C13	−179.70 (14)	C4—O1—C6—C7	−168.95 (15)
N2—N1—C2—C3	0.2 (2)	C4—O1—C6—C11	12.2 (2)
N2—N1—C2—C1	−179.32 (16)	C11—C6—C7—C8	0.0 (3)
F1—C1—C2—N1	0.6 (2)	O1—C6—C7—C8	−178.92 (15)
F2—C1—C2—N1	−120.56 (18)	C6—C7—C8—C9	−0.6 (3)
F3—C1—C2—N1	121.68 (18)	C7—C8—C9—C10	0.7 (3)
F1—C1—C2—C3	−178.87 (17)	C7—C8—C9—Cl1	−179.94 (13)
F2—C1—C2—C3	60.0 (2)	C8—C9—C10—C11	−0.1 (3)
F3—C1—C2—C3	−57.8 (2)	Cl1—C9—C10—C11	−179.43 (12)
N1—C2—C3—C4	0.0 (2)	C8—C9—C10—C12	−178.78 (16)
C1—C2—C3—C4	179.51 (17)	Cl1—C9—C10—C12	1.8 (2)
N1—C2—C3—C13	−178.68 (17)	C7—C6—C11—C10	0.7 (3)
C1—C2—C3—C13	0.8 (3)	O1—C6—C11—C10	179.45 (15)
C6—O1—C4—N2	−112.02 (17)	C9—C10—C11—C6	−0.6 (2)
C6—O1—C4—C3	74.6 (2)	C12—C10—C11—C6	178.15 (16)
N1—N2—C4—O1	−174.50 (14)	O2—N3—C13—C3	−179.26 (15)
C5—N2—C4—O1	4.2 (3)	C4—C3—C13—N3	0.5 (3)
N1—N2—C4—C3	0.4 (2)	C2—C3—C13—N3	178.78 (17)
C5—N2—C4—C3	179.09 (17)	N3—O2—C14—O3	179.52 (15)
C2—C3—C4—O1	173.74 (18)	N3—O2—C14—C15	−0.3 (2)
C13—C3—C4—O1	−7.6 (3)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3ⁱⁱⁱ	0.96	2.55	3.102 (2)	117

Symmetry code: (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClF₃N₃O₃
M_r	375.73
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	113
a, b, c (Å)	11.951 (2), 19.549 (4), 13.726 (3)
V (Å³)	3206.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.16 × 0.12 × 0.08

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.955, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	21575, 3686, 3208
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.115, 1.10
No. of reflections	3686
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.33

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3ⁱ	0.960	2.547	3.102 (2)	117

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by the Science and Technology Projects Fund of Nantong City (grant Nos. K2010016, AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010, 09 C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

References

Fu, N., Zou, X.-M., Lin, D.-Y., Zhu, Y.-Q. & Yang, H.-Z. (2008). Acta Cryst. E64, o192. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hagiwara, K. & Suzuki, H. (1996). Jpn Patent No. 08193067. Google Scholar
Li, Y., Yang, X.-P., Zhang, H.-Q., Meng, X.-G. & Liu, Z.-J. (2006). Acta Cryst. E62, o2027–o2029. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ranatunge, R. R., Augustyniak, M., Bandarage, U. K., Earl, R. A., Ellis, J. L., Garvey, D. S., Janero, D. R., Letts, L. G., Martino, A. M., Murty, M. G., Richardson, S. K., Schroeder, J. D., Shumway, M. J., Tam, S. W., Trocha, A. M. & Young, D. V. (2004). J. Med. Chem. 47, 2180–2193. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vonhoff, S., Piens, K., Pipelier, M., Braet, C., Claeyssens, M. & Vasella, A. (1999). Helv. Chim. Acta, 82, 963–980. CrossRef CAS Google Scholar
Wood, J. L., Stoltz, B. M., Goodman, S. N. & Onwueme, K. (1997). J. Am. Chem. Soc. 119, 9652–9661. CSD CrossRef CAS Web of Science Google Scholar

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Volume 67| Part 3| March 2011| Page o726

doi:10.1107/S1600536811006696

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

(E)-1-Methyl-5-(3-methyl-4-chloro­phen­­oxy)-3-tri­fluoro­meth­yl-1H-pyrazole-4-carbaldehyde O-acetyl­oxime

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-1-Methyl-5-(3-methyl-4-chlorophenoxy)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-acetyloxime