Different N—H···π interactions in two indole derivatives

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We describe the syntheses and crystal structures of two indole derivatives, namely 6-isopropyl-3-(2-nitro-1-phenyl- ethyl)-1H-indole, C19H20N2O2, (I) and 2-(4-methoxyphenyl)-3-(2-nitro-1-phenylethyl)-1H-indole, C23H20N2O3, (II): thelatter crystallises with two molecules A and B with similar conformations (r.m.s. overlay fit = 0.139Å) in the asymmetricunit. Despite the presence of O atoms as potential acceptors for classical hydrogen bonds, the dominant intermolecularinteraction 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 interactions ineach case but aromatic π–π stacking interactions are absent.
Original languageEnglish
Pages (from-to)699-703
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Issue number5
Early online date15 Apr 2016
Publication statusPublished - May 2016

Bibliographical note

We thank the EPSRC National Crystallography Service (University of Southampton) for the data collections and the EPSRC National Mass Spectrometry Service (University of Swansea) for the HRMS data


  • crystal structure
  • indole
  • N—H⋯π inter­action
  • chains
  • inversion dimers


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