Synthesis and structure of 1-(2-bromophenyl)-2-chloro-3-(2-chloracetyl)-1H-indole

In the title indole derivative, C16H10BrCl2NO, the dihedral angle between the mean plane of the indole ring system and the mean plane of the disordered 2-bromophenyl ring is 77.6 (1)°. The non-H atoms of the chloracetyl group are essentially coplanar with the indole core. In the crystal, pairs of molecules are face-to-face embraced via two weak C—H...O hydrogen bonds, forming inversion dimers with an interplanar distance between two parallel indole planes of 3.360 (3) Å. These dimers are connected by head-to-head Cl...Cl intermolecular contacts to build a two-dimensional molecular sheet parallel to (101). Neighbouring molecular sheets are stacked together to construct the three-dimensional structure by further short Cl...Cl intermolecular contacts. The atoms of the bromophenyl group were refined as disordered over two sets of sites with refined occupancies of 0.61 (2) and 0.39 (2).