1-Benzoyl-3-(4-hydroxyphenyl)thiourea

In the title compound, C14H12N2O2S, the aminophenol and the benzoyl groups adopt a syn–anti configuration with respect to the thiono C=S group across the thiourea C—N. The dihedral angle between the mean planes of the benzoyl and hydroxyphenyl rings is 36.77 (8)°. The molecules are stabilized by intramolecular N—H⋯O hydrogen bonds. In the crystal, weak intermolecular C—H⋯O, O—H⋯S and N—H⋯O hydrogen bonds link the molecules into a chain along the c axis.

In the title compound, C 14 H 12 N 2 O 2 S, the aminophenol and the benzoyl groups adopt a syn-anti configuration with respect to the thiono C S group across the thiourea C-N. The dihedral angle between the mean planes of the benzoyl and hydroxyphenyl rings is 36.77 (8) . The molecules are stabilized by intramolecular N-HÁ Á ÁO hydrogen bonds. In the crystal, weak intermolecular C-HÁ Á ÁO, O-HÁ Á ÁS and N-HÁ Á ÁO hydrogen bonds link the molecules into a chain along the c axis.

Comment
The title compound, I, is closely related to the previously reported N-benzoyl-N'-(3-hydroxyphenyl)thiourea (II) (Abosadiya et al., 2007) compound. As in most benzoylthiourea derivatives of the type R 1 C(O)NHC(S)NHR 2 , the title compound has a syn-anti configuration for the hydroxyphenyl and benzoyl groups with respect to the thiono C=S bond across the thiourea C-N bond (Fig 1). The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable to those in (II). All C-N bond lengths are shorter than the normal value for C-N single bond, and the bond lengths C7-O1 and C8-S1 become longer than normal values for a double bond, which suggests the presence of delocalized π-electrons.

Experimental
The title compound was first synthesized by (Zhang et al., 2001) under the condition of solid-liquid phase transfer catalysis using polyethylene glycol as catalyst, however, a much simpler method was used to synthesize the title compound. The reaction scheme involved a reaction of benzoyl chloride (10 mmol) with ammonium thiocyanate (10 mmol) in dry acetone.
The product, benzoyl isothiocyanate was reacted with 4-hydroxy aniline (10 mmol) to give the title compound with a 56% yield. A slow evaporation of ethanolic solution of the compound gave light brawn crystals suitable for X-ray diffraction.

Refinement
All the non hydrogen atom were refined anisotropically. the hydrogen positions were calculated to give an idealized geometry fixed to ride on their respective atoms, with U iso =1.2U eq (C) for aromatic (CH = 0.93 Å), U iso =1.2U eq (N) for N (NH = 0.86 Å) and U iso =1.5U eq (O) for OH (OH = 0.82 Å).  Fig. 1. The molecular structure of (I), with displacement ellipsods drawn at the 50% probability level. Dashed lines indicate intramolecular N-H···O hydrogen bonds.  as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1