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

Jamie R. Kerr; Laurent Trembleau; John M. D. Storey; James L. Wardell; William T. A. Harrison

doi:10.1107/S2056989016006162

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

Jamie R. Kerr, Laurent Trembleau, John M. D. Storey, James L. Wardell, William T. A. Harrison

Chemistry

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

11 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 language	English
Pages (from-to)	699-703
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
Issue number	5
Early online date	15 Apr 2016
DOIs	https://doi.org/10.1107/S2056989016006162
Publication status	Published - May 2016

Keywords

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

Access to Document

10.1107/S2056989016006162Licence: CC BY

Different N—H⋯π interactions in two indole derivatives
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. http://creativecommons.org/licenses/by/4.0/
Final published version, 878 KBLicence: CC BY

Cite this

@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 = may,

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 -

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this