Ethyl 2-(5-bromo-2-iodo­anilino)cyclo­pent-1-ene-1-carboxyl­ate

Paul Barnes; John M. D. Storey; William T. A. Harrison

doi:10.1107/S2414314615021781

Ethyl 2-(5-bromo-2-iodoanilino)cyclopent-1-ene-1-carboxylate

Paul Barnes
, John M. D. Storey
, William T. A. Harrison

Chemistry

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

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Abstract

In the title compound, C14H15BrINO2, the conformation of the C—O—CH2—CH3 grouping is anti [torsion angle = 173.8 (6)°] and the bond-angle sum at the N atom bridging the two rings is 360°. An unusual intramolecular bifurcated N—H⋯(O,I) hydrogen bond helps to establish the molecular conformation, in which the I atom and the C=O grouping are syn. In the crystal, inversion dimers created by pairs of short intermolecular C—I⋯O interactions [C—I = 2.080 (7) Å; I⋯O = 3.211 (5) Å; C—I⋯O = 152.4 (2)°] occur.

Original language	English
Article number	x152178
Pages (from-to)	1-7
Number of pages	7
Journal	IUCrData
Volume	1
Issue number	1
Early online date	1 Jan 2016
DOIs	https://doi.org/10.1107/S2414314615021781
Publication status	Published - Jan 2016

Bibliographical note

Acknowledgements
We thank the EPSRC National Crystallography Service
(University of Southampton) for the data collection.

Keywords

bifurcated hydrogen bond
cyclopentene
C—I⋯O interaction
crystal structure

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Ethyl 2-(5-bromo-2-iodoanilino)cyclopent-1-ene-1-carboxylate
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Cite this

@article{623e70299efd40c5986eec4be5c6362d,

title = "Ethyl 2-(5-bromo-2-iodoanilino)cyclopent-1-ene-1-carboxylate",

abstract = "In the title compound, C14H15BrINO2, the conformation of the C{\textemdash}O{\textemdash}CH2{\textemdash}CH3 grouping is anti [torsion angle = 173.8 (6)°] and the bond-angle sum at the N atom bridging the two rings is 360°. An unusual intramolecular bifurcated N{\textemdash}H⋯(O,I) hydrogen bond helps to establish the molecular conformation, in which the I atom and the C=O grouping are syn. In the crystal, inversion dimers created by pairs of short intermolecular C{\textemdash}I⋯O interactions [C{\textemdash}I = 2.080 (7) {\AA}; I⋯O = 3.211 (5) {\AA}; C{\textemdash}I⋯O = 152.4 (2)°] occur.",

keywords = "bifurcated hydrogen bond, cyclopentene, C{\textemdash}I⋯O interaction, crystal structure",

author = "Paul Barnes and Storey, \{John M. D.\} and Harrison, \{William T. A.\}",

note = "Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the data collection.",

year = "2016",

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doi = "10.1107/S2414314615021781",

language = "English",

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TY - JOUR

T1 - Ethyl 2-(5-bromo-2-iodoanilino)cyclopent-1-ene-1-carboxylate

AU - Barnes, Paul

AU - Storey, John M. D.

AU - Harrison, William T. A.

N1 - Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the data collection.

PY - 2016/1

Y1 - 2016/1

N2 - In the title compound, C14H15BrINO2, the conformation of the C—O—CH2—CH3 grouping is anti [torsion angle = 173.8 (6)°] and the bond-angle sum at the N atom bridging the two rings is 360°. An unusual intramolecular bifurcated N—H⋯(O,I) hydrogen bond helps to establish the molecular conformation, in which the I atom and the C=O grouping are syn. In the crystal, inversion dimers created by pairs of short intermolecular C—I⋯O interactions [C—I = 2.080 (7) Å; I⋯O = 3.211 (5) Å; C—I⋯O = 152.4 (2)°] occur.

AB - In the title compound, C14H15BrINO2, the conformation of the C—O—CH2—CH3 grouping is anti [torsion angle = 173.8 (6)°] and the bond-angle sum at the N atom bridging the two rings is 360°. An unusual intramolecular bifurcated N—H⋯(O,I) hydrogen bond helps to establish the molecular conformation, in which the I atom and the C=O grouping are syn. In the crystal, inversion dimers created by pairs of short intermolecular C—I⋯O interactions [C—I = 2.080 (7) Å; I⋯O = 3.211 (5) Å; C—I⋯O = 152.4 (2)°] occur.

KW - bifurcated hydrogen bond

KW - cyclopentene

KW - C—I⋯O interaction

KW - crystal structure

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DO - 10.1107/S2414314615021781

M3 - Article

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