1-Benzoyl-3,3-bis(propan-2-yl)thiourea

Two independent thiourea derivatives comprise the asymmetric unit of the title compound, C14H20N2OS. The major difference between the molecules relates to a twist in the relative orientation of the benzene rings [torsion angles = 4.5 (2) and −19.9 (2)° for the two independent molecules]. The thiocarbonyl and carbonyl groups lie to opposite sides of the molecule as there are twists about the central N—S bond [torsion angles = 83.90 (15) and 81.77 (15)°]. Supramolecular chains extending parallel to [101] with a stepped topology and mediated by N—H⋯O hydrogen bonding feature in the crystal structure. C—H⋯O and C—H⋯π interactions are also present.

Two independent thiourea derivatives comprise the asymmetric unit of the title compound, C 14 H 20 N 2 OS. The major difference between the molecules relates to a twist in the relative orientation of the benzene rings [torsion angles = 4.5 (2) and À19.9 (2) for the two independent molecules]. The thiocarbonyl and carbonyl groups lie to opposite sides of the molecule as there are twists about the central N-S bond [torsion angles = 83.90 (15) and 81.77 (15) ]. Supramolecular chains extending parallel to [101] with a stepped topology and mediated by N-HÁ Á ÁO hydrogen bonding feature in the crystal structure. C-HÁ Á ÁO and C-HÁ Á Á interactions are also present.   Table 1 Hydrogen-bond geometry (Å , ).

Related literature
Cg is the centroid of the C1-C6 ring.  -tumour, anti-fungal, anti-bacterial, insecticidal, herbicidal, pesticidal agents, and plant-growth regulators (Venkatachalam et al., 2004;Yuan et al., 2001;Zhou et al., 2004). N-[Di(alkyl/ aryl)carbamothioyl]benzamide derivatives provide immense opportunities for altering electronic and steric effects in its metal complexes. This might help in designing effective catalysts. Ruthenium(III) complexes containing these ligands have recently been used as catalysts for oxidation of alcohols to carbonyl compounds (Gunasekaran et al., 2010). The structure of the title thiourea derivative, (I), was investigated to provide reference data for subsequent studies.

D-HÁ
Two independent molecules comprise the asymmetric unit of (I). The first independent molecule, Fig. 1, is virtually super-imposable upon the second, Fig. 2, with the major difference between them being a twist in the benzene rings, Fig. 3. This is quantified by the C2-C1-C7-O1 and C16-C15-C21-O2 torsion angles of 4.5 (2) and -19.9 (2) °, respectively. This is also reflected in the r.m.s. deviation for bond distances and angles of 0.0035 Å and 0.903 °, respectively (Spek, 2009). The molecules are twisted about the central thiourea bond as seen in the C7-N1-C8-S1 and C21-N3-C22-S2 torsion angles of 83.90 (15) and 81.77 (15) °, respectively, indicating that the thiocarbonyl and carbonyl groups lie to opposite sides of the molecule.
The most notable feature in the crystal packing is the formation of supramolecular chains mediated by N-H···O hydrogen bonding, Table 1; chains are reinforced by C-H···O contacts involving the O2 atom, Table 1. The chains comprise alternating pairs of molecules of opposite orientation so that the topology is stepped. Chains aggregate into layers in the ac plane with the primary interactions between them along the b axis being of the type C-H···π, Fig. 5 and Table 1.

Experimental
A solution of benzoyl chloride (0.70285 g, 5 mmol) in acetone (50 ml) was added drop wise to a suspension of potassium thiocyanate (0.4859 g, 5 mmol) in anhydrous acetone (50 ml). The reaction mixture was heated under reflux for 45 minutes and then cooled to room temperature. A solution of diisopropyl amine (0.5059 g, 5 mmol) in acetone (30 ml) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and the resulting white solid was filtered, washed with water and dried in vacuo. Single crystals for X-ray diffraction were grown at room temperature

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2 to 1.5U equiv (C). The N-bound H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N-H 0.86±0.01 Å; their U iso values were freely refined supplementary materials sup-2 Figures Fig. 1. The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.     Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.