N-(Diphenylcarbamothioyl)-3-methylbenzamide

Abstract

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.

Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

“…Over the past couple of years we have been focusing on the preparation and characterization of new carboxamides which are bonded with a thiourea group [1,2,3,4,5,25,26,27,28,29,30,31,32]. Taking into consideration all the features described above, we focused our efforts in the present work on the synthesis of carboxamide derivatives.…”