1-Methyl-3-trifluoro­methyl-5-[(3-chloro­phen­yl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chloro­benzo­yl)oxime

Hong Dai; Hai-Jun Zhang; Lei Shi; Kun-Peng Luo; Yu-Jun Shi

doi:10.1107/S1600536811047970

. 2011 Nov 19;67(Pt 12):o3343. doi: 10.1107/S1600536811047970

1-Methyl-3-trifluoromethyl-5-[(3-chlorophenyl)sulfanyl]-1H-pyrazole-4-carbaldehyde O-(4-chlorobenzoyl)oxime

Hong Dai ^a, Hai-Jun Zhang ^a, Lei Shi ^a, Kun-Peng Luo ^a, Yu-Jun Shi ^a,^*

PMCID: PMC3238989 PMID: 22199838

Abstract

In the title compound, C₁₉H₁₂Cl₂F₃N₃O₂S, the 3-chlorophenyl and 4-chlorophenyl rings form dihedral angles 89.5 (2) and 11.4 (2)°, respectively, with the pyrazole ring. In the crystal, molecules related by translation along the a axis are linked into chains via C—H⋯N hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₉H₁₂Cl₂F₃N₃O₂S
M _r = 474.28
Monoclinic,
a = 8.1405 (16) Å
b = 18.680 (4) Å
c = 13.737 (3) Å
β = 96.10 (3)°
V = 2077.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 113 K
0.18 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T _min = 0.922, T _max = 0.947
11802 measured reflections
3654 independent reflections
2794 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.137
S = 1.10
3654 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 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.

Supplementary Material

Crystal structure: contains datablock(s) r80421a, I. DOI: 10.1107/S1600536811047970/cv5193sup1.cif

e-67-o3343-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047970/cv5193Isup2.hkl

e-67-o3343-Isup2.hkl^{(179.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047970/cv5193Isup3.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—H5⋯N2ⁱ	0.93	2.49	3.365 (4)	156

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Symmetry code: (i) Inline graphic .

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 Nos. K2010016 and AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010 and 09C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

supplementary crystallographic information

Comment

As a continuation of our structural investigation of pyrazole oxime esters (Dai et al., 2011), we report here the structure of the title compound (I).

In (I) (Fig. 1), all bonds lengths and angles are comparable with those observed in the related compound (Dai et al., 2011). The mean planes p1 (C7/C8/C9/N2/N1), p2 (C1/C2/C3/C4/C5/C6) and p3 (C13/C14/C15/C16/C17/C18) form the following dihedral angles - p2/p1 89.5 (2)°, p3/p1 11.4 (3)°. The crystal packing shows weak intermolecular C—H···N interactions (Table 1), which link molecules into chains along the a axis.

Experimental

To a well stirred solution of 1-methyl-3-trifluoromethyl-5-(3-chlorophenthio)- 1H-pyrazole-4-carbaldehyde oxime (4 mmol), and pyridine (5 ml) in 40 ml of dichloromethane, was added dropwise 4-chlorobenzoyl chloride (5 mmol) at room temperature. The resulting solution was heated to reflux for 7 h and cooled to room temperature. The mixture 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 (12:1 v/v) as eluent, and then recrystallized from petroleum ether/ethyl acetate acetate to give a colourless crystal.