(E)-1-Methyl-5-(3-methyl-4-chloro-phen-oxy)-3-trifluoro-meth-yl-1H-pyrazole-4-carbaldehyde O-acetyl-oxime.

In the title mol-ecule, C(15)H(13)ClF(3)N(3)O(3), the pyrazole and benzene rings form a dihedral angle of 77.6 (3)°. In the crystal, mol-ecules 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 inter-actions [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 = 375.73

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.115

S = 1.10

3686 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

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.

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

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

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

C15H13ClF3N3O3	F(000) = 1536
Mr = 375.73	Dx = 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

Rigaku Saturn diffractometer	3686 independent reflections
Radiation source: rotating anode	3208 reflections with I > 2σ(I)
confocal	Rint = 0.061
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −12→15
Tmin = 0.955, Tmax = 0.977	k = −25→24
21575 measured reflections	l = −14→17

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(Fo2) + (0.0516P)2 + 1.0705P] where P = (Fo2 + 2Fc2)/3
3686 reflections	(Δ/σ)max = 0.005
229 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 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
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*

	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)

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)

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

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) .