1-Benzoyl-3-(5-quinolyl)thiourea

The title compound, C17H13N3OS, was obtained by the reaction of benzoyl chloride, ammonium thiocyanate and 5-aminoquinoline in the presence of polyethyleneglycol-400 (PEG-400) as a phase-transfer catalyst. The compound crystallized as discrete molecules linked by N—H⋯N and C—H⋯N hydrogen bonds involving all the potential donors, generating sheets parallel to (100). An intramolecular N—H⋯O bond is also present.

The title compound, C 17 H 13 N 3 OS, was obtained by the reaction of benzoyl chloride, ammonium thiocyanate and 5aminoquinoline in the presence of polyethyleneglycol-400 (PEG-400) as a phase-transfer catalyst. The compound crystallized as discrete molecules linked by N-HÁ Á ÁN and C-HÁ Á ÁN hydrogen bonds involving all the potential donors, generating sheets parallel to (100). An intramolecular N-HÁ Á ÁO bond is also present.

Experimental
The title compound was synthesized as following. A mixture of benzoyl chloride (1400 mg, 10 mmol), ammonium thiocyanate (1140 mg, 15 mmol), 5-aminoquinoline (1300 mg, 9 mmol) and dichloromethane (50 ml) in the presence of PEG-400 (1200 mg, 3 mmol) as phase transfer catalyst at room temperature for 8h with stirring. The reaction mixture was evaporated to give a residue. Singles crystals suitable for X-ray analysis were obtained by slow evaporation of a mixture solution of dichloromethane and ethanol.

Refinement
The atom H6 attached to N1 and the atom H7 attached to N2 was located in a difference Fourier map and refined with N-H distance restrained to 0.87 (2)Å, and with U iso (H) = 0.85U eq (N) and U iso (H) = 1.91U eq (N) All H atoms bound to carbon were refined using riding models with d(C-H) = 0.93Å and U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.