Weak interactions in the crystal structures of two indole derivatives

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

doi:10.1107/S2056989016008616

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)

^*Corresponding author for this work

Chemistry

Instituto de Tecnologia em Fármacos, FarManguinhos

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

1 Citation (Scopus)

9 Downloads (Pure)

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 language	English
Pages (from-to)	964-968
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
Issue number	7
DOIs	https://doi.org/10.1107/S2056989016008616
Publication status	Published - 1 Jul 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 bonds
inversion dimers
weak interactions

Access to Document

10.1107/S2056989016008616Licence: CC BY

Weak interactions in the crystal structures of 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.
Final published version, 605 KBLicence: CC BY

Cite this

@article{96a0d015abf645c3b673e4928b30c9b2,

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",

month = jul,

day = "1",

doi = "10.1107/S2056989016008616",

language = "English",

volume = "72",

pages = "964--968",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "7",

}

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

SN - 2056-9890

VL - 72

SP - 964

EP - 968

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - 7

ER -

Weak interactions in the crystal structures of two indole derivatives

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this