6-Chloro-2-chloromethyl-4-phenylquinazoline 3-oxide

In the title compound, C15H10Cl2N2O, the dihedral angle between the mean planes of the phenyl ring and the 10-membered quinazoline ring is 63.3 (4)°. In the crystal, pairs of weak C—H⋯O interactions link the molecules into centrosymmetric dimers, forming R 2 2(10) graph-set ring motifs. In addition, weak π–π stacking interactions [minimum centroid–centroid separation = 3.6810 (8) Å] are observed, which contribute to the formation of a supramolecular assembly in the packing array.

In the title compound, C 15 H 10 Cl 2 N 2 O, the dihedral angle between the mean planes of the phenyl ring and the 10membered quinazoline ring is 63.3 (4) . In the crystal, pairs of weak C-HÁ Á ÁO interactions link the molecules into centrosymmetric dimers, forming R 2 2 (10) graph-set ring motifs. In addition, weakstacking interactions [minimum centroidcentroid separation = 3.6810 (8) Å ] are observed, which contribute to the formation of a supramolecular assembly in the packing array.
TSY thanks the University of Mysore for research facilities and also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
Supporting information for this paper is available from the IUCr electronic archives (Reference: ZS2289).
In the title compound the dihedral angle between the mean planes of the phenyl ring and the 10-membered quinazolin ring is 63.3 (4)° (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, a weak C15-H15A···O1 intermolecular interaction link the molecules into centrosymmetric dimers forming R 2 2 (10) graph set ring motifs (Fig. 2).

Experimental
6-chloro-2-(chloromethyl)-3,4-dihydro-4-phenylquinazoline (10 g, 0.03434 mol) was dissolved in 40 ml of methanol and stirred for 5 mins at room temperature. To this mixture, 10 g of 50% H 2 O 2 solution (5 g, 0.147 mol) was added dropwise over 30 mins, maintaining the temperature below 313 K, then stirred for 6 hrs in a RB flask, cooled, filtered and dried at 333 K (Fig. 3). The precipitate was dissolved in a (1:1) mixture of toluene and methylene dichloride at 313 K. After a few days, X-ray quality crystals appeared on slow evaporation.

Refinement
All of the H atoms were placed in their calculated positions and then refined using the riding model with C-H bond lengths of 0.93Å (CH) or 0.97Å (CH 2 ). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH 2 ) supplementary materials sup-2 Acta Cryst. (2014). E70, o440-o441 times U eq of the parent atom.

Figure 3
Synthesis scheme of (I). Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq  (17)