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

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Abstract

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
Volume72
Issue number5
Early online date15 Apr 2016
DOIs
Publication statusPublished - May 2016

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Keywords

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

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