The effect of Cl⋯π interactions on the conformations of 4-chloro-5-(2-phenoxyethoxy)phthalonitrile and 4-chloro-5-[2- (pentafluorophenoxy)ethoxy]phthalonitrile

Akiko Hori, Yuta Inoue, Hidetaka Yuge

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5 Citations (Scopus)

Abstract

4-Chloro-5-(2-phen-oxy-eth-oxy)phthalonitrile, C 16H 11ClN 2O 2, (I), and 4-chloro-5-[2-(penta-fluoro- phen-oxy)eth-oxy]phthalo-nitrile, C 16H6ClF 5N 2O 2, (II), show different types of electrostatic inter-action. In (I), the phen-oxy and phthalonitrile (benzene-1,2- dicarbonitrile) moieties are well separated in an open conformation and inter-molecular C - H⋯π inter-actions are observed in the crystal packing. On the other hand, in (II), the penta-fluoro-phen-oxy moiety inter-acts closely with the Cl atom to form a folded conformation containing an intra-molecular halogen-π inter-action.

Original languageEnglish
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume67
Issue number5
DOIs
Publication statusPublished - 2011 May
Externally publishedYes

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Conformations
Nitriles
Halogens
Benzene
Electrostatics
Atoms
Crystals

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

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title = "The effect of Cl⋯π interactions on the conformations of 4-chloro-5-(2-phenoxyethoxy)phthalonitrile and 4-chloro-5-[2- (pentafluorophenoxy)ethoxy]phthalonitrile",
abstract = "4-Chloro-5-(2-phen-oxy-eth-oxy)phthalonitrile, C 16H 11ClN 2O 2, (I), and 4-chloro-5-[2-(penta-fluoro- phen-oxy)eth-oxy]phthalo-nitrile, C 16H6ClF 5N 2O 2, (II), show different types of electrostatic inter-action. In (I), the phen-oxy and phthalonitrile (benzene-1,2- dicarbonitrile) moieties are well separated in an open conformation and inter-molecular C - H⋯π inter-actions are observed in the crystal packing. On the other hand, in (II), the penta-fluoro-phen-oxy moiety inter-acts closely with the Cl atom to form a folded conformation containing an intra-molecular halogen-π inter-action.",
author = "Akiko Hori and Yuta Inoue and Hidetaka Yuge",
year = "2011",
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doi = "10.1107/S0108270111008675",
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journal = "Acta Crystallographica Section C: Crystal Structure Communications",
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T1 - The effect of Cl⋯π interactions on the conformations of 4-chloro-5-(2-phenoxyethoxy)phthalonitrile and 4-chloro-5-[2- (pentafluorophenoxy)ethoxy]phthalonitrile

AU - Hori, Akiko

AU - Inoue, Yuta

AU - Yuge, Hidetaka

PY - 2011/5

Y1 - 2011/5

N2 - 4-Chloro-5-(2-phen-oxy-eth-oxy)phthalonitrile, C 16H 11ClN 2O 2, (I), and 4-chloro-5-[2-(penta-fluoro- phen-oxy)eth-oxy]phthalo-nitrile, C 16H6ClF 5N 2O 2, (II), show different types of electrostatic inter-action. In (I), the phen-oxy and phthalonitrile (benzene-1,2- dicarbonitrile) moieties are well separated in an open conformation and inter-molecular C - H⋯π inter-actions are observed in the crystal packing. On the other hand, in (II), the penta-fluoro-phen-oxy moiety inter-acts closely with the Cl atom to form a folded conformation containing an intra-molecular halogen-π inter-action.

AB - 4-Chloro-5-(2-phen-oxy-eth-oxy)phthalonitrile, C 16H 11ClN 2O 2, (I), and 4-chloro-5-[2-(penta-fluoro- phen-oxy)eth-oxy]phthalo-nitrile, C 16H6ClF 5N 2O 2, (II), show different types of electrostatic inter-action. In (I), the phen-oxy and phthalonitrile (benzene-1,2- dicarbonitrile) moieties are well separated in an open conformation and inter-molecular C - H⋯π inter-actions are observed in the crystal packing. On the other hand, in (II), the penta-fluoro-phen-oxy moiety inter-acts closely with the Cl atom to form a folded conformation containing an intra-molecular halogen-π inter-action.

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