2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl 4-bromobenzene-1-sulfonate

The title molecule, C22H17BrN2O4S, has a twisted U shape, the dihedral angle between the quinazolin-4-one and bromobenzene ring systems being 46.25 (8)°. In order to avoid steric clashes with adjacent substituents on the quinazolin-4-one ring, the N-bound tolyl group occupies an orthogonal position [dihedral angle = 89.59 (8)°]. In the crystal, molecules are connected into a three-dimensional architecture by C—H⋯O interactions, with the ketone O atom accepting two such bonds and a sulfonate O atom one.

The crystal structure determination of (I) is reported herein.
Overall, the shape of (I), Fig. 1, is of a twisted U as the bromobenzene ring is folded over towards the quinazolin-4-one group. The dihedral angle between the bromobenzene and quinazolin-4-one [r.m.s. deviation = 0.040 Å for the ten atoms] groups is 46.25 (8)°. The dihedral angle between the quinazolin-4-one and N-bound tolyl group is 89.59 (8)° indicating an orthogonal arrangement, an orientation which precludes steric clashes with the substituents on the quinazolin-4-one group.
In the crystal packing, C-H···O interactions involving bifurcated ketone-O and one of the sulfonate-O atoms are formed, Table 1. These lead to a three-dimensional architecture, Fig. 2.

Experimental
A mixture of 8-hydroxymethaqualone (532 mg, 0.0002 M) and 4-bromobenzenesulfonyl chloride (534 mg, 0.0021 mmol) in 15 ml pyridine was stirred at room temperature for 11 h. The solvent was removed under reduced pressure, and the residue was triturated with water and filtered. The solid obtained was dried and recrystallized from EtOH.  The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.  A view in projection down the a axis of the unit-cell contents for (I). The C-H···O interactions are shown as orange dashed lines.

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