title: Synthesis and structure of 1-(2-bromo-phen-yl)-2-chloro-3-(2-chloracet-yl)-1H-indole.
abstract: 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-bromo-phenyl 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 mol-ecules are face-to-face embracedviatwo weak C-H⋯O hydrogen bonds, forming inversion dimers with an inter-planar distance between two parallel indole planes of 3.360 (3) Å. These dimers are connected by head-to-head Cl⋯Cl inter-molecular contacts to build a two-dimensional mol-ecular sheet parallel to (101). Neighbouring mol-ecular sheets are stacked together to construct the three-dimensional structure by further short Cl⋯Cl inter-molecular contacts. The atoms of the bromo-phenyl group were refined as disordered over two sets of sites with refined occupancies of 0.61 (2) and 0.39 (2).
authors.affiliation: School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Bing
authors.initials: B
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Lu
authors.affiliation: Technical Institute of Physics and Chemistry, Chinese Academy of Science, Beijing 100190, People's Republic of China.
authors.forename: Jun-Fang
authors.initials: JF
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Hong
authors.initials: H
authors.lastname: Lei
authors.affiliation: State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Fang
keywords: centrosymmetric dimer; crystal structure; hydrogen bonding; indole derivative; synthesis