2-Chloro-N-(2-chlorobenzoyl)-N-(2-ethyl-4-oxo-3,4-dihydroquinazolin-3-yl)benzamide

In the title compound, C24H17Cl2N3O3, the quinazolinone ring system is close to planar (r.m.s. deviation = 0.0132 Å), with the imide unit almost perpendicular to it, subtending a dihedral angle of 89.1 (1)°. However, the imide unit itself is not planar, the dihedral angle between the two O=C—N components being 34.6 (1)°. The dihedral angle between the two chlorobenzene rings is 40.50 (7)°, while the angles between these rings and the imide moiety are 54.6 (1) and 58.2 (1)°, respectively. The dihedral angles between the 2-chlorophenyl rings and the quinazolinone ring system are 48.77 (5) and 32.92 (7)° for rings A and B, respectively. In the crystal, weak C—H⋯O interactions link the molecules into a three-dimensional array.


Structural commentary
In the title compound, C 24 H 17 Cl 2 N 3 O 3 , the quinazolinone ring is planar with the imide moiety (O1A C1A N C1B O1B) almost perpendicular with a dihedral angle of 89.1 (1)°. However, the imide moiety itself is not strictly planar. The dihedral angle between the two components (O1A C1A N and O1B C1B N) is 34.6 (1)°. The dihedral angle between the two 2-chlorophenyl rings is 40.50 (7)° while the angles between these and the imide moiety are 54.6 (1)° and 58.2 (1)° for rings A and B respectively. The dihedral angles between the 2-chlorophenyl rings and the quinazolinone ring are 48.77 (5)° and 32.92 (7)° for A and B respectively. Weak C-H···O interactions link the molecules into a 3-D array.

Supramolecular features
Weak C-H···O interactions link the molecules into a 3-D array.

Database survey
For the synthesis and biological evaluation of some imido-substituted 1,4-naphthoquinone derivatives, see; Bakare et al.

Synthesis and crystallization
To a solution of 3-amino-2-ethyl-4(3H) quinazolinone (186 mg) in tetrahydrofuran (15 mL) was added NaH (70.7 mg) and the mixture stirred at room temperature for 15 min. 2-Chloro-benzoyl chloride (0.273 mL) was added drop wise and the resulting mixture stirred at room temperature for 20 hr. The reaction mixture was poured into a mixture of ice (10 g) and water (10 mL) and then extracted with dichloromethane (25 mL). The organic layer was washed with water (3X20 mL), saturated sodium chloride solution (20 mL), dried over anhydrous MgSO 4 and the solvent removed in vacuo to give a white solid. The crude white solid was dissolved in hot ethanol:water mixture (2:3, 5 mL) from which the title sup-2 . E70, o503-o504 compound crystallized at room temperature after 6 days.

Refinement
H atoms were placed in geometrically idealized positions with a C-H distances of 0.95 and 0.99 Å U iso (H) = 1.2U eq (C) and 0.98 Å for CH 3 [U iso (H) = 1.5U eq (C)].  Packing diagram for the complex viewed along the b axis. C-H···O interactions shown by dashed lines. 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.