Different N-H⋯π inter-actions in two indole derivatives.
We describe the syntheses and crystal structures of two indole derivatives, namely 6-isopropyl-3-(2-nitro-1-phenyl-eth-yl)-1H-indole, C19H20N2O2, (I), and 2-(4-meth-oxy-phen-yl)-3-(2-nitro-1-phenyl-eth-yl)-1H-indole, C23H20N2O3, (II); the latter crystallizes with two mol-ecules (A and B) with similar conformations (r.m.s. overlay fit = 0.139 Å) in the asymmetric unit. Despite the presence of O atoms as potential acceptors for classical hydrogen bonds, the dominant inter-molecular inter-action in each crystal is an N-H⋯π bond, which generates chains in (I) and A+A and B+B inversion dimers in (II). A different aromatic ring acts as the acceptor in each case. The packing is consolidated by C-H⋯π inter-actions in each case but aromatic π-π stacking inter-actions are absent.
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.
Jamie R
JR
Kerr
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.
Laurent
L
Trembleau
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.
John M D
JM
Storey
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland; Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil.
James L
JL
Wardell
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.
William T A
WT
Harrison
N—H⋯π inter­action; chains; crystal structure; indole; inversion dimers