5-(4-Chloro­phen­oxy)-1-methyl-3-tri­fluoro­methyl-1H-pyrazole-4-carbaldehyde O-[(2-chloro­pyridin-5-yl)meth­yl]oxime

Dai, H.; Zhu, P.-F.; Zhu, Y.-J.; Fang, J.-X.; Shi, Y.-J.

doi:10.1107/S1600536811046459

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3246

https://doi.org/10.1107/S1600536811046459

Open

access

5-(4-Chlorophenoxy)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-[(2-chloropyridin-5-yl)methyl]oxime

Hong Dai,^a,^b Peng-Fei Zhu,^a Yu-Jun Zhu,^a Jian-Xin Fang ^b ^* and Yu-Jun Shi ^a

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China, and ^bState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: nankaidx228@yahoo.com.cn

(Received 30 October 2011; accepted 3 November 2011; online 9 November 2011)

In the title molecule, C₁₈H₁₃Cl₂F₃N₄O₂, the intramolecular distance between the centroids of the benzene and pyridine rings is 3.953 (3) Å, and the trifluoromethyl group is rotationally disordered over two orientations in a 0.678 (19):0.322 (19) ratio. The crystal packing exhibits weak intermolecular C—H⋯F interactions.

Related literature

For the crystal structure of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₃Cl₂F₃N₄O₂
M_r = 445.22
Monoclinic, P 2₁ /c
a = 12.269 (3) Å
b = 10.443 (2) Å
c = 15.702 (3) Å
β = 108.93 (3)°
V = 1902.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 113 K
0.14 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.947, T_max = 0.969
10759 measured reflections
3356 independent reflections
2845 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.07
3356 reflections
291 parameters
66 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5C⋯F3ⁱ	0.96	2.55	3.488 (7)	165
C11—H11⋯F3′ⁱⁱ	0.93	2.56	3.358 (14)	144
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); 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: https://doi.org/10.1107/S1600536811046459/cv5190sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046459/cv5190Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046459/cv5190Isup3.cml

checkCIF report

Comment top

As a continuation of our structural study of pyrazole oximes (Dai et al., 2011), we report here the crystal structure of the title compound (I).

In (I) (Fig. 1), all bonds lengths and angles are similar to those observed in the related compound (Dai et al., 2011). The dihedral angles between the planes of the pyridyl and pyrazole rings, and between the benzene and the pyrazole rings are 91.0 (3)° and 95.8 (3)°, respectively. The crystal packing displays weak intermolecular C—H···F interactions (Table 1).

Related literature top

For the crystal structure of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011).

Experimental top

To a well stirred solution of 1-methyl-3-trifluoromethyl-5-(4-chlorophenoxy)- 1H-pyrazole-4-carbaldehyde oxime (3 mmol) and 2-chloro-5-chloromethylpyridine (3.6 mmol) in 40 ml of anhydrous DMF, was added powdered potassium carbonate (7.5 mmol). The resulting solution was heated to 363 K for 10 h and cooled to room temperature. The mixture was poured into water (180 ml) and extracted with dichloromethane (4 * 50 ml). The organic layer was washed with saturated brine (3 * 30 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was separated by column chromatography on silica gel with petroleum ether/ethyl acetate (10:1 v/v) as eluent, and then recrystallized from ethyl acetate to give a colourless crystal.

Structure description top

As a continuation of our structural study of pyrazole oximes (Dai et al., 2011), we report here the crystal structure of the title compound (I).

For the crystal structure of a related pyrazole oxime studied recently by our group, see: Dai et al. (2011).

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 50% probabilty displacement ellipsoids.

5-(4-Chlorophenoxy)-1-methyl-3-trifluoromethyl-1H- pyrazole-4-carbaldehyde O-[(2-chloropyridin-5-yl)methyl]oxime top

Crystal data top

C₁₈H₁₃Cl₂F₃N₄O₂	F(000) = 904
M_r = 445.22	D_x = 1.554 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4362 reflections
a = 12.269 (3) Å	θ = 1.8–27.9°
b = 10.443 (2) Å	µ = 0.39 mm⁻¹
c = 15.702 (3) Å	T = 113 K
β = 108.93 (3)°	Monoclinic, colourless
V = 1902.9 (7) Å³	0.14 × 0.10 × 0.08 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	3356 independent reflections
Radiation source: rotating anode	2845 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.041
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −14→14
T_min = 0.947, T_max = 0.969	k = −12→12
10759 measured reflections	l = −14→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0531P)²] where P = (F_o² + 2F_c²)/3
3356 reflections	(Δ/σ)_max = 0.003
291 parameters	Δρ_max = 0.29 e Å⁻³
66 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₃Cl₂F₃N₄O₂	V = 1902.9 (7) Å³
M_r = 445.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.269 (3) Å	µ = 0.39 mm⁻¹
b = 10.443 (2) Å	T = 113 K
c = 15.702 (3) Å	0.14 × 0.10 × 0.08 mm
β = 108.93 (3)°

Data collection top

Rigaku Saturn diffractometer	3356 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	2845 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.969	R_int = 0.041
10759 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	66 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	Δρ_max = 0.29 e Å⁻³
3356 reflections	Δρ_min = −0.26 e Å⁻³
291 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	Occ. (<1)
Cl1	0.42312 (4)	0.81673 (5)	1.05301 (4)	0.03177 (16)
Cl2	0.24719 (4)	0.78497 (5)	0.81487 (3)	0.02958 (16)
F1	1.0291 (4)	0.1147 (5)	1.0472 (5)	0.0485 (14)	0.678 (19)
F2	0.8486 (6)	0.0969 (7)	1.0153 (6)	0.0436 (15)	0.678 (19)
F3	0.9173 (8)	0.1880 (6)	0.9233 (3)	0.0509 (13)	0.678 (19)
F1'	0.8773 (14)	0.0850 (14)	1.0406 (10)	0.040 (3)	0.322 (19)
F2'	0.8654 (15)	0.1804 (12)	0.9205 (6)	0.052 (3)	0.322 (19)
F3'	1.0278 (9)	0.1329 (11)	1.0091 (13)	0.054 (3)	0.322 (19)
O1	0.89000 (10)	0.62356 (11)	1.10140 (8)	0.0181 (3)
O2	0.76286 (11)	0.60323 (12)	0.81549 (8)	0.0197 (3)
N1	0.97610 (13)	0.30373 (14)	1.14348 (10)	0.0184 (3)
N2	0.96106 (13)	0.42594 (15)	1.16558 (10)	0.0177 (3)
N3	0.80499 (12)	0.57770 (15)	0.90895 (9)	0.0180 (3)
N4	0.43641 (14)	0.66049 (15)	0.83015 (11)	0.0229 (4)
C1	0.92933 (16)	0.17597 (18)	1.00931 (12)	0.0217 (4)
C2	0.92895 (15)	0.30085 (17)	1.05422 (12)	0.0173 (4)
C3	0.88375 (15)	0.41957 (17)	1.01704 (12)	0.0163 (4)
C4	0.90697 (14)	0.49692 (17)	1.09258 (11)	0.0159 (4)
C5	1.00381 (17)	0.4675 (2)	1.25933 (11)	0.0254 (5)
H5A	0.9811	0.5546	1.2635	0.038*
H5B	1.0863	0.4615	1.2812	0.038*
H5C	0.9721	0.4137	1.2950	0.038*
C6	0.77559 (15)	0.66348 (17)	1.08527 (11)	0.0171 (4)
C7	0.69070 (16)	0.58030 (18)	1.09125 (11)	0.0189 (4)
H7	0.7065	0.4937	1.1029	0.023*
C8	0.58119 (17)	0.62885 (18)	1.07952 (12)	0.0206 (4)
H8	0.5226	0.5744	1.0827	0.025*
C9	0.55957 (17)	0.75740 (18)	1.06322 (12)	0.0204 (4)
C10	0.64499 (16)	0.84005 (18)	1.05618 (12)	0.0220 (4)
H10	0.6293	0.9266	1.0444	0.026*
C11	0.75420 (17)	0.79174 (17)	1.06702 (12)	0.0193 (4)
H11	0.8123	0.8455	1.0620	0.023*
C12	0.83287 (15)	0.46034 (18)	0.92371 (12)	0.0177 (4)
H12	0.8212	0.4026	0.8765	0.021*
C13	0.72665 (16)	0.73399 (18)	0.80495 (12)	0.0203 (4)
H13A	0.7263	0.7643	0.7465	0.024*
H13B	0.7817	0.7853	0.8505	0.024*
C14	0.60834 (16)	0.75256 (17)	0.81277 (11)	0.0173 (4)
C15	0.55696 (17)	0.87257 (19)	0.80193 (13)	0.0232 (4)
H15	0.5971	0.9441	0.7929	0.028*
C16	0.44578 (17)	0.88534 (19)	0.80457 (13)	0.0250 (5)
H16	0.4099	0.9649	0.7984	0.030*
C17	0.39031 (16)	0.77536 (19)	0.81674 (12)	0.0211 (4)
C18	0.54451 (16)	0.65150 (18)	0.82871 (12)	0.0211 (4)
H18	0.5794	0.5714	0.8392	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0236 (3)	0.0318 (3)	0.0403 (3)	0.0106 (2)	0.0108 (2)	0.0023 (2)
Cl2	0.0196 (3)	0.0357 (3)	0.0373 (3)	0.0061 (2)	0.0147 (2)	0.0090 (2)
F1	0.0318 (16)	0.0334 (17)	0.065 (3)	0.0189 (13)	−0.0060 (15)	−0.0266 (18)
F2	0.038 (2)	0.030 (2)	0.076 (4)	−0.0155 (17)	0.036 (2)	−0.021 (2)
F3	0.108 (4)	0.0256 (13)	0.0330 (16)	0.004 (3)	0.042 (2)	−0.0057 (12)
F1'	0.076 (7)	0.014 (3)	0.043 (5)	−0.016 (4)	0.037 (5)	−0.007 (3)
F2'	0.092 (7)	0.026 (3)	0.030 (3)	0.013 (5)	0.005 (4)	−0.008 (2)
F3'	0.029 (3)	0.047 (4)	0.103 (7)	−0.010 (3)	0.044 (4)	−0.041 (5)
O1	0.0169 (7)	0.0131 (6)	0.0238 (7)	−0.0001 (5)	0.0061 (5)	−0.0023 (5)
O2	0.0201 (7)	0.0238 (7)	0.0148 (6)	0.0045 (6)	0.0051 (5)	0.0026 (5)
N1	0.0178 (8)	0.0160 (8)	0.0231 (8)	0.0020 (7)	0.0087 (7)	0.0020 (6)
N2	0.0188 (8)	0.0169 (8)	0.0191 (8)	0.0020 (7)	0.0087 (7)	0.0009 (6)
N3	0.0167 (8)	0.0237 (9)	0.0135 (7)	0.0028 (7)	0.0049 (6)	0.0032 (7)
N4	0.0208 (9)	0.0206 (9)	0.0295 (9)	0.0007 (7)	0.0115 (7)	0.0026 (7)
C1	0.0201 (11)	0.0190 (10)	0.0277 (10)	−0.0003 (9)	0.0100 (9)	0.0008 (8)
C2	0.0151 (9)	0.0172 (10)	0.0229 (9)	−0.0008 (8)	0.0107 (8)	−0.0005 (8)
C3	0.0144 (9)	0.0161 (9)	0.0204 (9)	0.0002 (8)	0.0083 (8)	0.0001 (7)
C4	0.0132 (9)	0.0149 (9)	0.0210 (9)	0.0006 (7)	0.0074 (8)	0.0004 (7)
C5	0.0309 (12)	0.0278 (11)	0.0167 (9)	−0.0003 (9)	0.0065 (9)	0.0000 (8)
C6	0.0175 (10)	0.0197 (10)	0.0144 (9)	0.0025 (8)	0.0055 (8)	−0.0018 (7)
C7	0.0238 (10)	0.0138 (9)	0.0204 (9)	0.0007 (8)	0.0090 (8)	−0.0010 (8)
C8	0.0212 (10)	0.0208 (10)	0.0216 (9)	−0.0034 (8)	0.0094 (8)	−0.0014 (8)
C9	0.0198 (11)	0.0232 (10)	0.0179 (9)	0.0048 (8)	0.0058 (8)	−0.0020 (8)
C10	0.0288 (11)	0.0149 (9)	0.0221 (9)	0.0026 (8)	0.0079 (9)	0.0014 (8)
C11	0.0239 (10)	0.0151 (9)	0.0200 (9)	−0.0030 (8)	0.0086 (8)	−0.0012 (7)
C12	0.0155 (9)	0.0202 (10)	0.0178 (9)	−0.0014 (8)	0.0057 (8)	−0.0029 (8)
C13	0.0200 (11)	0.0200 (10)	0.0211 (9)	0.0015 (8)	0.0069 (8)	0.0051 (8)
C14	0.0189 (10)	0.0193 (10)	0.0135 (8)	−0.0018 (8)	0.0048 (8)	0.0012 (7)
C15	0.0242 (11)	0.0198 (10)	0.0277 (10)	−0.0022 (9)	0.0114 (9)	0.0028 (8)
C16	0.0280 (11)	0.0188 (10)	0.0311 (11)	0.0058 (9)	0.0136 (9)	0.0060 (8)
C17	0.0169 (10)	0.0275 (11)	0.0199 (9)	0.0022 (9)	0.0075 (8)	0.0023 (8)
C18	0.0208 (10)	0.0187 (10)	0.0248 (10)	0.0022 (8)	0.0090 (8)	0.0016 (8)

Geometric parameters (Å, º) top

Cl1—C9	1.743 (2)	C5—H5B	0.9600
Cl2—C17	1.7496 (19)	C5—H5C	0.9600
F1—C1	1.338 (4)	C6—C11	1.377 (3)
F2—C1	1.316 (5)	C6—C7	1.383 (3)
F3—C1	1.317 (4)	C7—C8	1.391 (3)
F1'—C1	1.324 (9)	C7—H7	0.9300
F2'—C1	1.362 (8)	C8—C9	1.376 (3)
F3'—C1	1.291 (7)	C8—H8	0.9300
O1—C4	1.353 (2)	C9—C10	1.389 (3)
O1—C6	1.406 (2)	C10—C11	1.390 (3)
O2—N3	1.4141 (18)	C10—H10	0.9300
O2—C13	1.429 (2)	C11—H11	0.9300
N1—C2	1.332 (2)	C12—H12	0.9300
N1—N2	1.351 (2)	C13—C14	1.509 (2)
N2—C4	1.345 (2)	C13—H13A	0.9700
N2—C5	1.459 (2)	C13—H13B	0.9700
N3—C12	1.273 (2)	C14—C18	1.384 (3)
N4—C17	1.314 (2)	C14—C15	1.388 (3)
N4—C18	1.337 (2)	C15—C16	1.384 (3)
C1—C2	1.483 (3)	C15—H15	0.9300
C2—C3	1.405 (3)	C16—C17	1.380 (3)
C3—C4	1.386 (2)	C16—H16	0.9300
C3—C12	1.458 (2)	C18—H18	0.9300
C5—H5A	0.9600

C4—O1—C6	116.69 (14)	H5B—C5—H5C	109.5
N3—O2—C13	107.19 (13)	C11—C6—C7	121.89 (17)
C2—N1—N2	104.05 (14)	C11—C6—O1	115.95 (16)
C4—N2—N1	111.86 (14)	C7—C6—O1	122.10 (16)
C4—N2—C5	127.74 (16)	C6—C7—C8	118.58 (17)
N1—N2—C5	120.38 (15)	C6—C7—H7	120.7
C12—N3—O2	110.88 (14)	C8—C7—H7	120.7
C17—N4—C18	116.05 (16)	C9—C8—C7	119.98 (18)
F3'—C1—F2	120.6 (6)	C9—C8—H8	120.0
F3'—C1—F3	79.8 (6)	C7—C8—H8	120.0
F2—C1—F3	107.2 (4)	C8—C9—C10	121.05 (18)
F3'—C1—F1'	108.4 (9)	C8—C9—Cl1	119.03 (15)
F2—C1—F1'	19.8 (7)	C10—C9—Cl1	119.91 (15)
F3—C1—F1'	122.8 (7)	C9—C10—C11	119.14 (18)
F3'—C1—F1	27.4 (6)	C9—C10—H10	120.4
F2—C1—F1	105.6 (4)	C11—C10—H10	120.4
F3—C1—F1	106.5 (3)	C6—C11—C10	119.32 (17)
F1'—C1—F1	88.5 (7)	C6—C11—H11	120.3
F3'—C1—F2'	103.7 (5)	C10—C11—H11	120.3
F2—C1—F2'	84.1 (6)	N3—C12—C3	117.79 (16)
F3—C1—F2'	27.1 (6)	N3—C12—H12	121.1
F1'—C1—F2'	102.5 (8)	C3—C12—H12	121.1
F1—C1—F2'	127.7 (6)	O2—C13—C14	112.62 (15)
F3'—C1—C2	117.1 (5)	O2—C13—H13A	109.1
F2—C1—C2	113.5 (4)	C14—C13—H13A	109.1
F3—C1—C2	112.8 (3)	O2—C13—H13B	109.1
F1'—C1—C2	112.2 (8)	C14—C13—H13B	109.1
F1—C1—C2	110.6 (2)	H13A—C13—H13B	107.8
F2'—C1—C2	111.6 (5)	C18—C14—C15	116.70 (17)
N1—C2—C3	113.29 (16)	C18—C14—C13	122.17 (17)
N1—C2—C1	116.93 (16)	C15—C14—C13	121.11 (17)
C3—C2—C1	129.77 (17)	C16—C15—C14	119.73 (18)
C4—C3—C2	102.40 (15)	C16—C15—H15	120.1
C4—C3—C12	126.31 (17)	C14—C15—H15	120.1
C2—C3—C12	131.13 (16)	C17—C16—C15	117.33 (18)
N2—C4—O1	120.07 (15)	C17—C16—H16	121.3
N2—C4—C3	108.40 (15)	C15—C16—H16	121.3
O1—C4—C3	131.42 (16)	N4—C17—C16	125.19 (17)
N2—C5—H5A	109.5	N4—C17—Cl2	115.64 (14)
N2—C5—H5B	109.5	C16—C17—Cl2	119.18 (15)
H5A—C5—H5B	109.5	N4—C18—C14	124.88 (18)
N2—C5—H5C	109.5	N4—C18—H18	117.6
H5A—C5—H5C	109.5	C14—C18—H18	117.6

C2—N1—N2—C4	−0.33 (19)	C12—C3—C4—O1	0.4 (3)
C2—N1—N2—C5	−179.09 (15)	C4—O1—C6—C11	−160.71 (15)
C13—O2—N3—C12	176.22 (14)	C4—O1—C6—C7	22.0 (2)
N2—N1—C2—C3	0.4 (2)	C11—C6—C7—C8	−0.8 (3)
N2—N1—C2—C1	−178.44 (14)	O1—C6—C7—C8	176.26 (15)
F3'—C1—C2—N1	−69.1 (10)	C6—C7—C8—C9	−0.6 (3)
F2—C1—C2—N1	78.6 (5)	C7—C8—C9—C10	1.5 (3)
F3—C1—C2—N1	−159.1 (5)	C7—C8—C9—Cl1	−177.60 (14)
F1'—C1—C2—N1	57.1 (8)	C8—C9—C10—C11	−0.9 (3)
F1—C1—C2—N1	−40.0 (5)	Cl1—C9—C10—C11	178.20 (13)
F2'—C1—C2—N1	171.6 (10)	C7—C6—C11—C10	1.4 (3)
F3'—C1—C2—C3	112.2 (10)	O1—C6—C11—C10	−175.83 (15)
F2—C1—C2—C3	−100.0 (5)	C9—C10—C11—C6	−0.6 (3)
F3—C1—C2—C3	22.2 (5)	O2—N3—C12—C3	176.84 (14)
F1'—C1—C2—C3	−121.5 (8)	C4—C3—C12—N3	−1.1 (3)
F1—C1—C2—C3	141.4 (5)	C2—C3—C12—N3	−175.70 (18)
F2'—C1—C2—C3	−7.1 (10)	N3—O2—C13—C14	−81.09 (17)
N1—C2—C3—C4	−0.4 (2)	O2—C13—C14—C18	0.2 (2)
C1—C2—C3—C4	178.33 (17)	O2—C13—C14—C15	−178.18 (16)
N1—C2—C3—C12	175.19 (17)	C18—C14—C15—C16	−2.0 (3)
C1—C2—C3—C12	−6.1 (3)	C13—C14—C15—C16	176.44 (17)
N1—N2—C4—O1	−176.49 (14)	C14—C15—C16—C17	−1.0 (3)
C5—N2—C4—O1	2.2 (3)	C18—N4—C17—C16	−2.2 (3)
N1—N2—C4—C3	0.12 (19)	C18—N4—C17—Cl2	177.86 (13)
C5—N2—C4—C3	178.76 (16)	C15—C16—C17—N4	3.3 (3)
C6—O1—C4—N2	−111.17 (17)	C15—C16—C17—Cl2	−176.79 (14)
C6—O1—C4—C3	73.1 (2)	C17—N4—C18—C14	−1.2 (3)
C2—C3—C4—N2	0.13 (18)	C15—C14—C18—N4	3.3 (3)
C12—C3—C4—N2	−175.71 (16)	C13—C14—C18—N4	−175.16 (17)
C2—C3—C4—O1	176.22 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5C···F3ⁱ	0.96	2.55	3.488 (7)	165
C11—H11···F3′ⁱⁱ	0.93	2.56	3.358 (14)	144

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Cl₂F₃N₄O₂
M_r	445.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	12.269 (3), 10.443 (2), 15.702 (3)
β (°)	108.93 (3)
V (Å³)	1902.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.14 × 0.10 × 0.08

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.947, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	10759, 3356, 2845
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.07
No. of reflections	3356
No. of parameters	291
No. of restraints	66
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.26

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—H5C···F3ⁱ	0.96	2.55	3.488 (7)	165
C11—H11···F3'ⁱⁱ	0.93	2.56	3.358 (14)	144

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20772068), the Science and Technology Projects Fund of Nantong City (grant No. K2010016, AS2010005), the Science Foundation of Nantong University (grant No. 09Z010, 09C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

References

Dai, H., Miao, W.-K., Wu, S.-S., Qin, X. & Fang, J.-X. (2011). Acta Cryst. E67, o775. Web of Science CSD CrossRef IUCr Journals 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3246

https://doi.org/10.1107/S1600536811046459

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

5-(4-Chloro­phen­­oxy)-1-methyl-3-tri­fluoro­methyl-1H-pyrazole-4-carbaldehyde O-[(2-chloro­pyridin-5-yl)meth­yl]oxime

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-(4-Chlorophenoxy)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-[(2-chloropyridin-5-yl)methyl]oxime