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

Research output: Contribution to journalArticle

2 Citations (Scopus)
4 Downloads (Pure)

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

Fingerprint

indoles
Dimers
Conformations
Hydrogen bonds
Crystal structure
Derivatives
Atoms
Crystals
Molecules
interactions
dimers
methylidyne
inversions
hydrogen bonds
crystal structure
rings
synthesis
crystals
atoms
indole

Keywords

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

Cite this

Different N—H···π interactions in two indole derivatives. / Kerr, Jamie R.; Trembleau, Laurent; Storey, John M. D.; Wardell, James L.; Harrison, William T. A.

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 72, No. 5, 05.2016, p. 699-703.

Research output: Contribution to journalArticle

@article{58f91c5c56d74d0ba76ff2dc32ef6da8,
title = "Different N—H···π interactions in two indole derivatives",
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 = 0.139{\AA}) 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.",
keywords = "crystal structure, indole, N—H⋯π inter­action, chains, inversion dimers",
author = "Kerr, {Jamie R.} and Laurent Trembleau and Storey, {John M. D.} and Wardell, {James L.} and Harrison, {William T. A.}",
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",
year = "2016",
month = "5",
doi = "10.1107/S2056989016006162",
language = "English",
volume = "72",
pages = "699--703",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "5",

}

TY - JOUR

T1 - Different N—H···π interactions in two indole derivatives

AU - Kerr, Jamie R.

AU - Trembleau, Laurent

AU - Storey, John M. D.

AU - Wardell, James L.

AU - Harrison, William T. A.

N1 - 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

PY - 2016/5

Y1 - 2016/5

N2 - 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.

AB - 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.

KW - crystal structure

KW - indole

KW - N—H⋯π inter­action

KW - chains

KW - inversion dimers

U2 - 10.1107/S2056989016006162

DO - 10.1107/S2056989016006162

M3 - Article

VL - 72

SP - 699

EP - 703

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 5

ER -