Crystal structures of four indole derivatives with a phenyl substituent at the 2-position and a carbonyl group at the 3-position: the C(6) N-H⋯O chain remains the same, but the weak reinforcing inter-actions are different

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Abstract

We describe the crystal structures of four indole derivatives with a phenyl ring at the 2-position and different carbonyl-linked substituents at the 3-position, namely 1-(2-phenyl-1H-indol-3-yl)ethanone, C16H13NO, (I), 2-cyclo-hexyl-1-(2-phenyl-1H-indol-3-yl)ethanone, C22H23NO, (II), 3,3-dimethyl-1-(2-phenyl-1H-indol-3-yl)butan-1-one, C20H21NO, (III), and 3-benzoyl-2-phenyl-1H-indole, C21H15NO, (IV). In each case, the carbonyl-group O atom lies close to the indole-ring plane and points towards the benzene ring. The dihedral angles between the indole ring system and 2-phenyl ring for these structures are clustered in a narrow range around 65°. The dominant inter-molecular inter-action in each case is an N-H⋯O hydrogen bond, which generates a C(6) chain, although each structure possesses a different crystal symmetry. The C(6) chains are consolidated by different (C-H⋯O, C-H⋯π and π-π stacking) weak inter-actions, with little consistency between the structures.

Original languageEnglish
Pages (from-to)363-369
Number of pages7
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
Issue number3
DOIs
Publication statusPublished - 1 Mar 2016

Bibliographical note

Acknowledgements
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.

Keywords

  • crystal structure
  • indole
  • N—H⋯O hydrogen bond
  • C(6) chain
  • weak inter­actions

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