3-Bromomethyl-2-chloromethyl-1-phenylsulfonyl-1H-indole

In the title compound, C16H13BrClNO2S, the indole mean plane forms a dihedral angle of 73.59 (19)° with the phenyl ring. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions. The Br atom is disordered over two positions with site occupancy factors of 0.7 and 0.3.

In the title compound, C 16 H 13 BrClNO 2 S, the indole mean plane forms a dihedral angle of 73.59 (19) with the phenyl ring. The molecular structure is stabilized by weak intramolecular C-HÁ Á ÁO interactions. The Br atom is disordered over two positions with site occupancy factors of 0.7 and 0.3.

S1. Comment
In continuation of our studies of indole derivatives, which are known to exhibit anti-oxidant activity (Olgen & Coban, 2003), antihepatitis B virus activities (Chai et al., 2006) and antibacterial (Nieto et al., 2005) activities, we report the crystal structure of the title compound (I).
The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007(Chakkaravarthi et al., , 2008. The indole mean plane forms a dihedral angle of 73.59 (19)° with the phenyl ring. The N1-S1-C1 plane is almost orthogonal to indole ring (dihedral angle 82.30 (22)°) and makes 76.93 (22)° with the phenyl ring. The indole mean plane and C8-C16-BR1 plane are nearly orthogonal to each other forming a dihedral angle of 82.23 (0.29)°.

S2. Experimental
1-(Phenylsulfonyl)-3-(bromomethyl)-2-methylindole (0.5 g, 1.37 mmol) was dissolved in dry ccl 4 (10 ml) and then powdered N-chloro succinimide was added. To this, azobisisobutyronitrle (50 mg) was also added and then refluxed for 2 h on a waterbath. After the reaction was completed, succinimide was floated on the surface of the reaction mixture. It was then filtered off and washed with CCl 4 (3 ml). The solvent was removed carefully under vacuo. The crude product was recrystallized from CCl 4 . Yield:76 percentage.
Only major parts of the disordered atoms are drawn. Intramolecular H-bonds are shown as dashed lines.