2-[2-(2-Anilino-4-oxo-3,4-dihydroquinazolin-3-yl)phenoxy]-3-phenylquinazolin-4(3H)-one methanol hemisolvate

In the title compound, C34H23N5O3·0.5CH3OH, each pyrimidinone heterocycle and its adjacent benzene ring are almost coplanar, making dihedral angles of 0.69 (13) and 1.87 (13)°. The lower pyrimidinone ring makes a dihedral angle of 40.41 (15)° with the —NH— bonded phenyl ring. O—H⋯O hydrogen bonds and weak C—H⋯π interactions are observed in the crystal structure. The methanol solvent molecule is disordered over two positions of equal occupancy.

In the title compound, C 34 H 23 N 5 O 3 Á0.5CH 3 OH, each pyrimidinone heterocycle and its adjacent benzene ring are almost coplanar, making dihedral angles of 0.69 (13) and 1.87 (13) . The lower pyrimidinone ring makes a dihedral angle of 40.41 (15) with the -NH-bonded phenyl ring. O-HÁ Á ÁO hydrogen bonds and weak C-HÁ Á Á interactions are observed in the crystal structure. The methanol solvent molecule is disordered over two positions of equal occupancy.   Table 1 Hydrogen-bond geometry (Å , ).

Related literature
Cg1 is the centroid of the C29-C34 ring.

Experimental
To a solution of iminophosphorane (1.40 g, 3.0 mmol) in anhydrous THF (10 ml) was added isocyanatobenzene (3 mmol) under nitrogen at room temperature. After reaction, the mixture was allowed to stand for 10 h at 273-278 K, the solvent was removed under reduced pressure and diethyl ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed to give 1-phenyl-3-(2-ethoxycarbonylphenyl) carbodiimide, which was used directly without further purification. To a solution of 1-phenyl-3-(2-ethoxycarbonylphenyl) carbodiimide in THF (15 ml) was added 2-aminophenol (1.5 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 2 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound. The product was recrystallized from methanol-dichloromethane (1:2 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction (yield 74%).

Refinement
All the carbon-bonded hydrogen atoms were located at theire ideal positons with C-H=0.93Å (aromatic) and 0.96Å (methyl), and U iso (H) = 1.2U eq C for aromatic and 1.5 U eq C for methyl hydrogen atoms, respectively. H atoms bonded to N and O atoms were found from the difference maps and then refined with distance restraints of N-H=0.91 (2)Å and O-H=0.96 (2) Å. The thermal factors were set k times of their carriar atoms (k =1.2 for N and 1.5 for O atoms). H20 and H35 was set attached to N1 and O5 atoms, respectively, and they were both constrained to be at their ideal positions.
supplementary materials sup-2 Figures Fig. 1. View of the molecular structure of (I), showing the atom labelling schemeand with displacement ellipsoids drawn at the 50% probability level.