N-(Diphenylcarbamothioyl)-3-methylbenzamide

The synthesis of the title compound, C21H18N2OS, involves the reaction of 3-methylbenzoyl chloride with potassium thiocyanate in dry acetone followed by condensation of the 3-methylbenzoyl isothiocyanate with diphenylamine. The carbonyl [C—O = 1.215 (2) Å] and thiocarbonyl [C—S = 1.6721 (17) Å] distances indicate that these correspond to double bonds. The short C—N bonds at the center of the molecule reveal the effects of resonance in this part of the molecule. The conformation of the molecule with respect to the thiocarbonyl and carbonyl groups is twisted. The 3-methylphenyl and two phenyl rings are also twisted, with dihedral angles of 75.67 (9) and 14.91 (9)°. The phenyl rings are rotated out of the mean plane of the N—C—S—N atoms by 66.87 (8) and 78.40 (9)°. Pairs of molecules are linked into centrosymmetric dimers via intermolecular N—H⋯S interactions and a C—H⋯O link also occurs. The dimers are stacked along the a axis.

[1]  H. Arslan,et al.  Synthesis and characterization of nickel and copper complexes with 2,2-diphenyl- N -(alkyl(aryl)carbamothioyl)acetamide: The crystal structures of HL1 and cis -[Ni(L1)2] , 2008 .

[2]  K. R. Koch.  New chemistry with old ligands: N-alkyl- and N,N-dialkyl-N′-acyl(aroyl)thioureas in co-ordination, analytical and process chemistry of the platinum group metals , 2001 .

[3]  Michael Bolte,et al.  1-(4-Chlorobenzoyl)-3-(2,4,6-trichlorophenyl)thiourea hemihydrate , 2008, Acta crystallographica. Section E, Structure reports online.

[4]  Anilesh Kumar,et al.  LIQUID-LIQUID EXTRACTION OF GOLD(III) AND ITS SEPARATION OVER COPPER(II), IRON(III), AND ZINC(II) USING THIOUREA DERIVATIVES FROM CHLORIDE MEDIA , 1998 .

[5]  H. Arslan,et al.  Synthesis and characterization of copper(II), nickel(II) and cobalt(II) complexes with novel thiourea derivatives , 2003 .

[6]  H. Arslan,et al.  Synthesis, characterization, and crystal structure of 1-(4-chloro-benzoyl)-3-naphthalen-1-yl-thiourea , 2003 .

[7]  H. Arslan,et al.  Synthesis, characterization and thermal behavior of 1,1-dialkyl-3-(4-(3,3-dialkylthioureidocarbonyl)-benzoyl)thiourea and its Cu(II), Ni(II), and Co(II) complexes , 2006 .

[8]  S. Anwar,et al.  1-(2,6-Dichlorobenzoyl)-3-(2,3,5,6-tetrachlorophenyl)thiourea trichloromethane hemisolvate , 2009, Acta crystallographica. Section E, Structure reports online.

[9]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[10]  Anil Kumar,et al.  Solvent extraction of copper(II) from chloride media using N-(thiocarbamoyl)benzamidine and N-benzoylthiourea derivatives , 1999 .

[11]  Michael Bolte,et al.  1-(3-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea , 2009, Acta crystallographica. Section E, Structure reports online.

[12]  Michael Bolte,et al.  1-(3-Chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea , 2009, Acta crystallographica. Section E, Structure reports online.

[13]  D. VanDerveer,et al.  Synthesis and characterization of N -(alky(aryl)carbamothioyl)cyclohexanecarboxamide derivatives and their Ni(II) and Cu(II) complexes , 2009 .