Crystal structure of N-[1-(2,6-dichloro-4-trifluoromethyl)phenyl-3- cyano-1H-pyrazol-5-yl]-N'-4-methoxybenzoyl thioureas, C20H12Cl2F3N5O2S
Zeitschrift für Kristallographie - New Crystal Structures
C20H12CI2F3N5O2S, monoclinic, Clcl (no. 9 ), a = 12.501(5) Â, b = 24.987(9) Â, c = 7.667(3) k,ß= 108.185(7)°, V = 2275.3 Â 3 , Ζ = 4, R gt (F) = 0.063, wR^F) = 0.144, Γ =298 Κ. Source of material Following the method of [ 1 ] reaction of 2,6-dichloro-4-trifluoromethylamine (0.01 mol) with a suspension of nitrosyl sulfuric acid, followed by reaction with a solution of ethyl 2,3-dicyanopropionate (0.01 mol) in acetic acid, gave the title compound (about 0.005 mol) (1). Further more, according to
... more, according to the method , 4-methoxy-benzoyl chlordie (0.007 mol) with dry potassium thiocyanate (0.1 mol) was refluxed in anhydrous CH3CN for 2 h at the temperature 80 °C, which was then filtrated to obtain acylisothiocyanate solution (2). The obtained products 1 and 2 were reacted in anhydrous CH3CN for about 4 h to get the tide compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of the solution in acetone (m.p. 473 -475 K). IR, 'H NMR and 13 C NMR data are available in the CIF. Experimental details The H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of ¿(Csp 2 -H) = 0.93 Â with C/iso = 1.2 i/eq(parent atom), d(Csp 3 -H) = 0.96 Â with î/ iso = 1.5 C/eq(parent atom). The large U e q of CI and fluorine atoms as com-pared to neighbours may be attributed to (rotational) disorder of the CF3 group fluorine atoms. We want to refine the crystal structure taking into account the disorder, but failed to do it. Discussion Acyl thiourea derivatives show good bioactivity and may be used in many fields, such as in antimicrobial, sterilization, insecticide and herbicidal    . Recently, same derivatives have been reported to be effective against HIV [6, 7] . Futhermore, the pyrazoles with the groups of chloride and trifluoromethyl, like 5amino-3-cyano-1 -(2,6-dichloro-4-trifluoromethylphenyl)-4trifluoromethylsulphenylpyrazole or 5-amino-3-cyano-l-(2,6dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole, show good bioactivities, too  . Hence it is necessary to combine these two parts into new acyl thioureas. The molecule of the title compound an acylthioureas with an overall U-shape. In the crystal structure, the dihedral angles between the pyrazole and attached phenyl ring and the methoxyphenyl are 88.9(1)° and 30.5(1)°, respectively. An intramolecular N4-H4-01 hydrogen bond with an N4-01 seperation of 2.577(4) Â, stablizes the molecule.