3-(3-Methoxybenzoyl)-1,1-diphenylthiourea

The thiono and carbonyl groups in the title compound, C21H18N2O2S, adopt an anti disposition with respect to the central C—N bond. The diphenylamine rings are twisted relative to each other by a dihedral angle of 82.55 (10)°. The 3-methoxybenzoyl fragment is twisted relative to one of the diphenylamine rings, forming a dihedral angle of 74.04 (9)°. In the crystal, pairs of intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers, forming columns parallel to the a axis.

The thiono and carbonyl groups in the title compound, C 21 H 18 N 2 O 2 S, adopt an anti disposition with respect to the central C-N bond. The diphenylamine rings are twisted relative to each other by a dihedral angle of 82.55 (10) . The 3methoxybenzoyl fragment is twisted relative to one of the diphenylamine rings, forming a dihedral angle of 74.04 (9) . In the crystal, pairs of intermolecular N-HÁ Á ÁS hydrogen bonds link the molecules into centrosymmetric dimers, forming columns parallel to the a axis.
In the crystal structure, Intermolecular N1-H1A···S1 hydrogen bond link the molecules into a centrosymmetric dimers forming channel parallel to the a-axis.

Experimental
The title compound was prepared according to a previously reported procedure (Al-abbasi et al., 2010) using 3-methoxybenzoyl chloride and diphenylamine as the appropriate starting materials. A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from ethanol solution at room temperature (yield 75%).

Refinement
Hydrogen atom of the amide group was determined from the difference Fourier map and N-H was initially fixed at 0.86(0.01) Å and allowed to be refined on the parent N atom with U iso (H) = 1.2U eq (N). All other H atoms were positioned geometrically with C-H bond lengths in the range 0.93 -0.97 Å and refined in the riding model approximation with U iso (H)=1.2U eq (C,N), except for methyl group where U iso (H)= 1.5U eq (C).
Figures Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Fig. 2. A packing diagram of the title compound viewed down the a-axis
showing the intermolecular hydrogen bonds N1-H1···S1 (-x + 1, -y + 1, -z + 1) centrosymmetric dimers along a-axis. as those based on F, and R-factors based on ALL data will be even larger.