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

Hong Dai; Peng-Fei Zhu; Yu-Jun Zhu; Jian-Xin Fang; Yu-Jun Shi

doi:10.1107/S1600536811046459

. 2011 Nov 9;67(Pt 12):o3246. doi: 10.1107/S1600536811046459

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,^*, Yu-Jun Shi ^a

PMCID: PMC3238903 PMID: 22199756

Abstract

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,
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[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 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

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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046459/cv5190sup1.cif

e-67-o3246-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046459/cv5190Isup2.hkl

e-67-o3246-Isup2.hkl^{(164.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046459/cv5190Isup3.cml

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

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.