3-Benzoyl-1-(2-methoxyphenyl)thiourea

In the title compound, C15H14N2O2S, the central C2N2OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å). This is ascribed to the formation of an S(6) loop stabilized by an intramolecular N—H⋯O hydrogen bond; additional intramolecular N—H⋯O and C—H⋯S contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5)°, respectively. The thione S and ketone O atoms are mutually anti, as are the N—H H atoms; the O atoms lie to the same side of the molecule. Centrosymmetric eight-membered {⋯HNC=S}2 synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C—H⋯O and C—H⋯π interactions.

In the title compound, C 15 H 14 N 2 O 2 S, the central C 2 N 2 OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å ). This is ascribed to the formation of an S(6) loop stabilized by an intramolecular N-HÁ Á ÁO hydrogen bond; additional intramolecular N-HÁ Á ÁO and C-HÁ Á ÁS contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5) , respectively. The thione S and ketone O atoms are mutually anti, as are the N-H H atoms; the O atoms lie to the same side of the molecule. Centrosymmetric eight-membered {Á Á ÁHNC S} 2 synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C-HÁ Á ÁO and C-HÁ Á Á interactions.
The most significant interaction in the crystal packing is the formation of centrosymmetric eight-membered {···HNC=S} 2 synthons owing to the presence of N-H···S hydrogen bonds (Table ). These inversion dimers stack along the a axis and are connected into a three-dimensional architecture by C-H···O and C-H···π interactions ( Fig. 2 and Table 1).

Experimental
A solution of benzoyl chloride (0.005 mol, 0.7029 g) in acetone (30 ml) was added drop wise to a suspension of potassium thiocyanate (0.005 mol, 0.4859 g) in anhydrous acetone (30 ml). The reaction mixture was heated under reflux for 45 minutes and then cooled to room temperature. A solution of substituted 2-methoxyaniline (0.005 mol, 0.6158 g). 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 resulting solid was filtered, washed with water and dried in vacuo. The resulting solid product was recrystallized from ethanol/dichloromethane (1:2 ratio) solution. Yield: 87%, M. pt: 409 K. Anal. Calcd. for C 15 H 14 N 2 O 2 S (%): C, 62.9; H,4.9;N,9.8;Found: C,63.1;H,5.1;N,9.6. Spectroscopic data for the title compound are given in the archived CIF.

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95 to 0.98 Å, U iso (H) = 1.2U eq (C) or 1.5U eq (C methyl )] and were included in the refinement in the riding model approximation. The N-bound H-atoms were refined freely.

Computing details
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).    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 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.