Hydrogen bonding in two solid phases of phenazine-chloranilic acid (1/1) determined at 170 and 93 K

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Abstract

The crystal structures in two solid phases, i.e. phase II stable between 146 and 253 K and phase IV below 136 K, of the title compound [phenazine-chloranilic acid (1/1), C12H8N 2·C6H2Cl2O4, in phase II, and phenazinium hydrogen chloranilate, C12H 9N2+·C6HCl2O 4-, in phase IV], have been determined. Both phases crystallize in P21, and each structure was refined as an inversion twin. In phase II, the phenazine and chloranilic acid molecules are arranged alternately through two kinds of O-H⋯N hydrogen bonds. In phase IV, salt formation occurs by donation of one H atom from the chloranilic acid molecule to the phenazine molecule; the resulting monocation and monoanion are linked by N-H⋯O and O-H⋯N hydrogen bonds.

Original languageEnglish
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume63
Issue number1
DOIs
Publication statusPublished - 2007

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Hydrogen Bonding
solid phases
Hydrogen
Hydrogen bonds
acids
Molecules
hydrogen
hydrogen bonds
molecules
Salts
Crystal structure
inversions
salts
Atoms
crystal structure
atoms
chloranilic acid
phenazine

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

Cite this

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title = "Hydrogen bonding in two solid phases of phenazine-chloranilic acid (1/1) determined at 170 and 93 K",
abstract = "The crystal structures in two solid phases, i.e. phase II stable between 146 and 253 K and phase IV below 136 K, of the title compound [phenazine-chloranilic acid (1/1), C12H8N 2·C6H2Cl2O4, in phase II, and phenazinium hydrogen chloranilate, C12H 9N2+·C6HCl2O 4-, in phase IV], have been determined. Both phases crystallize in P21, and each structure was refined as an inversion twin. In phase II, the phenazine and chloranilic acid molecules are arranged alternately through two kinds of O-H⋯N hydrogen bonds. In phase IV, salt formation occurs by donation of one H atom from the chloranilic acid molecule to the phenazine molecule; the resulting monocation and monoanion are linked by N-H⋯O and O-H⋯N hydrogen bonds.",
author = "Kazuma Gotoh and Tetsuo Asaji and Hiroyuki Ishida",
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language = "English",
volume = "63",
journal = "Acta Crystallographica Section C: Crystal Structure Communications",
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T1 - Hydrogen bonding in two solid phases of phenazine-chloranilic acid (1/1) determined at 170 and 93 K

AU - Gotoh, Kazuma

AU - Asaji, Tetsuo

AU - Ishida, Hiroyuki

PY - 2007

Y1 - 2007

N2 - The crystal structures in two solid phases, i.e. phase II stable between 146 and 253 K and phase IV below 136 K, of the title compound [phenazine-chloranilic acid (1/1), C12H8N 2·C6H2Cl2O4, in phase II, and phenazinium hydrogen chloranilate, C12H 9N2+·C6HCl2O 4-, in phase IV], have been determined. Both phases crystallize in P21, and each structure was refined as an inversion twin. In phase II, the phenazine and chloranilic acid molecules are arranged alternately through two kinds of O-H⋯N hydrogen bonds. In phase IV, salt formation occurs by donation of one H atom from the chloranilic acid molecule to the phenazine molecule; the resulting monocation and monoanion are linked by N-H⋯O and O-H⋯N hydrogen bonds.

AB - The crystal structures in two solid phases, i.e. phase II stable between 146 and 253 K and phase IV below 136 K, of the title compound [phenazine-chloranilic acid (1/1), C12H8N 2·C6H2Cl2O4, in phase II, and phenazinium hydrogen chloranilate, C12H 9N2+·C6HCl2O 4-, in phase IV], have been determined. Both phases crystallize in P21, and each structure was refined as an inversion twin. In phase II, the phenazine and chloranilic acid molecules are arranged alternately through two kinds of O-H⋯N hydrogen bonds. In phase IV, salt formation occurs by donation of one H atom from the chloranilic acid molecule to the phenazine molecule; the resulting monocation and monoanion are linked by N-H⋯O and O-H⋯N hydrogen bonds.

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