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

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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 languageEnglish
Article numberx152178
Pages (from-to)1-7
Number of pages7
JournalIUCrData
Volume1
Issue number1
Early online date1 Jan 2016
DOIs
Publication statusPublished - Jan 2016

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Conformations
Atoms
Dimers
Torsional stress
Hydrogen bonds
Crystals
cyclodrine

Keywords

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

Cite this

Ethyl 2-(5-bromo-2-iodo­anilino)cyclo­pent-1-ene-1-carboxyl­ate. / Barnes, Paul; Storey, John M. D.; Harrison, William T. A.

In: IUCrData, Vol. 1, No. 1, x152178, 01.2016, p. 1-7.

Research output: Contribution to journalArticle

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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) {\AA}; I⋯O = 3.211 (5) {\AA}; C—I⋯O = 152.4 (2)°] occur.",
keywords = "bifurcated hydrogen bond, cyclopentene, C—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.",
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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.

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KW - crystal structure

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