Crystal structure of N-[1-(2,6-dichloro-4-trifluoromethyl)phenyl-3- cyano-1H-pyrazol-5-yl]-N'-4-methoxybenzoyl thioureas, C20H12Cl2F3N5O2S

Abstract

Source of materialFollowing 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 the method [2], 4-methoxy-benzoyl chlordie (0.007 mol) with dry potassium thiocyanate (0.1.mol) was refluxed in anhydrous CH 3 CN 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 CH 3 CN for about 4 h to get the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of the solution in acetone (m.p. 473 -475 K). IR, 1 H NMR and 13 C NMR data are available in the CIF. Experimental detailsThe H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(Csp 2 -H) = 0.93 Å with U iso = 1.2 U eq (parent atom), d(Csp 3 -H) = 0.96 Å with U iso = 1.5 U eq (parent atom). The large U eq of C1 and fluorine atoms as compared to neighbours may be attributed to (rotational) disorder of the CF 3 group fluorine atoms. We want to refine the crystal structure taking into account the disorder, but failed to do it. DiscussionAcyl thiourea derivatives show good bioactivity and may be used in many fields, such as in antimicrobial, sterilization, insecticide and herbicidal [3][4][5]. Recently, same derivatives have been reported to be effective against HIV [6,7]. Futhermore, the pyrazoles with the groups of chloride and trifluoromethyl, like 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphenylpyrazole or 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole, show good bioactivities, too [1]. 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)°,r espectively. An intramolecular N4−H4···O1 hydrogen bond with an N4···O1 seperation of 2.577(4) Å,stablizes the molecule.