Weak interactions in the crystal structures of two indole derivatives

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

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Abstract

We describe the syntheses and crystal structures of two indole derivatives, namely a second monoclnic polymorph of ethyl 5-chloro-1H-indole-2-carboxylate (I) and ethyl 5-chloro-3-iodo-1H-indole-2-carboxylate (II). In their crystal structures, both compounds form inversion dimers linked by pairs of N—H···O hydrogen bonds, which generate R2 2(10) loops. The dimers are linked into double chains in (I) and sheets in (II) by a variety of weak interactions, including π-π stacking, C—I···π, C—Cl—π interactions and I···Cl halogen bonds.
Original languageEnglish
Pages (from-to)964-968
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
Issue number7
DOIs
Publication statusPublished - 1 Jul 2016

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indoles
Dimers
Crystal structure
Derivatives
carboxylates
crystal structure
Halogens
Polymorphism
dimers
Hydrogen bonds
halogens
inversions
hydrogen bonds
synthesis
indole
indole-2-carboxylate
interactions

Keywords

  • crystal structure
  • indole
  • N-H...O hydrogen bonds
  • inversion dimers
  • weak interactions

Cite this

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title = "Weak interactions in the crystal structures of two indole derivatives",
abstract = "We describe the syntheses and crystal structures of two indole derivatives, namely a second monoclnic polymorph of ethyl 5-chloro-1H-indole-2-carboxylate (I) and ethyl 5-chloro-3-iodo-1H-indole-2-carboxylate (II). In their crystal structures, both compounds form inversion dimers linked by pairs of N—H···O hydrogen bonds, which generate R2 2(10) loops. The dimers are linked into double chains in (I) and sheets in (II) by a variety of weak interactions, including π-π stacking, C—I···π, C—Cl—π interactions and I···Cl halogen bonds.",
keywords = "crystal structure, indole, N-H...O hydrogen bonds, inversion dimers, weak interactions",
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",
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language = "English",
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pages = "964--968",
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TY - JOUR

T1 - Weak interactions in the crystal structures of 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 - 2016/7/1

Y1 - 2016/7/1

N2 - We describe the syntheses and crystal structures of two indole derivatives, namely a second monoclnic polymorph of ethyl 5-chloro-1H-indole-2-carboxylate (I) and ethyl 5-chloro-3-iodo-1H-indole-2-carboxylate (II). In their crystal structures, both compounds form inversion dimers linked by pairs of N—H···O hydrogen bonds, which generate R2 2(10) loops. The dimers are linked into double chains in (I) and sheets in (II) by a variety of weak interactions, including π-π stacking, C—I···π, C—Cl—π interactions and I···Cl halogen bonds.

AB - We describe the syntheses and crystal structures of two indole derivatives, namely a second monoclnic polymorph of ethyl 5-chloro-1H-indole-2-carboxylate (I) and ethyl 5-chloro-3-iodo-1H-indole-2-carboxylate (II). In their crystal structures, both compounds form inversion dimers linked by pairs of N—H···O hydrogen bonds, which generate R2 2(10) loops. The dimers are linked into double chains in (I) and sheets in (II) by a variety of weak interactions, including π-π stacking, C—I···π, C—Cl—π interactions and I···Cl halogen bonds.

KW - crystal structure

KW - indole

KW - N-H...O hydrogen bonds

KW - inversion dimers

KW - weak interactions

U2 - 10.1107/S2056989016008616

DO - 10.1107/S2056989016008616

M3 - Article

VL - 72

SP - 964

EP - 968

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 7

ER -