3-{[(Dibenzylcarbamothioyl)amino]carbonyl}benzamide

Two independent molecules with quite similar conformations, A and B, comprise the asymmetric unit of the title compound, C23H21N3O2S. The terminal amide substituent is coplanar with the attached benzene ring [the O—C—C—C torsion angles are 174.0 (2) (A) and 6.3 (3)° (B)]. In the same way, the central amide group [C—C—C—O = 7.8 (3) (A) and 11.5 (3)° (B)] is approximately coplanar with the ring to which it is attached. A major twist is noted between the amide and adjacent thioamide residues [C—N—C—S = −109.29 (19) (A) and −112.29 (19)° (B)]. In the crystal, supramolecular chains along [100] are formed by N—H⋯O and N—H⋯S hydrogen bonding. These are connected into a three-dimensional architecture by C—H⋯π and π–π interactions [inter-centroid distance = 3.9157 (12) Å].

supplementary materials  In an attempt to prepare a bipodal acylthiourea derivative (Bourne et al., 2005) from dibenzylamine, isophthaloyl dichloride and potassium thiocyanate in acetone, the title compound, (I), was obtained as a by-product.

Experimental
Isophthaloyl dichloride (2.0302 g, 10 mmol) dissolved in acetone (80 ml), was placed in a dropping funnel and added drop wise with stirring to potassium thiocyanate (1.9436 g, 20 mmol) dissolved in acetone (80 ml), under N 2 atmosphere, in a three-necked round bottom flask. The mixture was heated to reflux for 30 minutes and then allowed to cool. A solution of dibenzylamine (3.9456 g, 20 mmol) in acetone (80 ml) was added drop wise from a dropping funnel to the reaction mixture and the resulting mixture was stirred for 2 h at room temperature. Then, hydrochloric acid (0.1 N, 300 ml) was added and the resulting white solid was filtered off, washed with water and dried in vacuo. Single crystals were grown at room temperature from acetonitrile/dimethyl formamide mixture (

Figure 1
Molecular structures of the two independent molecules comprising the asymmetric unit of (I) showing atom-labelling scheme and displacement ellipsoids at the 70% probability level.

Figure 2
Overlay diagram of the two independent molecules in (I). The molecules have been superimposed so that the N-C-N atoms are overlapped. Red image: S1-containing molecule. Blue image, S2-containing molecule.

Figure 4
A view of the unit-cell contents in projection down the c axis in (I). The N-H···O, N-H···S, C-H···π and π-π interactions are shown as blue, orange, purple and pink dashed lines, respectively.

3-{[(Dibenzylcarbamothioyl)amino]carbonyl}benzamide
Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. 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 > 2σ(F 2 ) is used only for calculating R-factors(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.