(Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate

The bis-Schiff base title compound, C20H16N2O4·C7H8, crystallized as a toluene solvate. In the solid state, it is present as its prototropic tautomer formed by transfer of one of the ortho-hydroxyl H atoms. The proton transfer is accompanied by a shift of electron pairs, as is evident from...

Full description

Bibliographic Details
Main Authors: Hasan Zargoshi, Valiollah Mirkhani, Reza Kia, Hoong-Kun Fun
Format: Article
Language:English
Published: International Union of Crystallography 2008-09-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536808026305
id doaj-0caf12c1693f46488d793505dab53000
record_format Article
spelling doaj-0caf12c1693f46488d793505dab530002020-11-25T00:50:37ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682008-09-01649o1790o179110.1107/S1600536808026305(Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvateHasan ZargoshiValiollah MirkhaniReza KiaHoong-Kun FunThe bis-Schiff base title compound, C20H16N2O4·C7H8, crystallized as a toluene solvate. In the solid state, it is present as its prototropic tautomer formed by transfer of one of the ortho-hydroxyl H atoms. The proton transfer is accompanied by a shift of electron pairs, as is evident from the observed C—O and C—N bond distances of 1.305 (2) and 1.315 (2) Å, which are largely consistent with C=O and C—N distances. The actual molecule present in the solid state is thus the charge-neutral β-keto amine, with a small contribution of its zwitterionic valence tautomer via partial delocalization of electron pairs along the N—C—C—C—O atom chain. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 51.99 (8) and 12.95 (9)°. Intramolecular O—H...N and N—H...O hydrogen bonds generate S(6) ring motifs, whereas intramolecular N—H...N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O—H...O hydrogen bonds and weak C—H...O interactions link the molecules into one-dimensional zigzag chains along the b axis; these chains are further stacked by O—H...O and weak C—H...O interactions along the c axis, forming two-dimensional extended networks parallel to the bc plane. In addition, the crystal structure is further stabilized by weak C—H...π and π–π interactions.http://scripts.iucr.org/cgi-bin/paper?S1600536808026305
collection DOAJ
language English
format Article
sources DOAJ
author Hasan Zargoshi
Valiollah Mirkhani
Reza Kia
Hoong-Kun Fun
spellingShingle Hasan Zargoshi
Valiollah Mirkhani
Reza Kia
Hoong-Kun Fun
(Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
Acta Crystallographica Section E
author_facet Hasan Zargoshi
Valiollah Mirkhani
Reza Kia
Hoong-Kun Fun
author_sort Hasan Zargoshi
title (Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
title_short (Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
title_full (Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
title_fullStr (Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
title_full_unstemmed (Z)-6-{2-[(E)-2,4-Dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
title_sort (z)-6-{2-[(e)-2,4-dihydroxybenzylideneamino]phenylaminomethylene}-3-hydroxycyclohexa-2,4-dienone toluene solvate
publisher International Union of Crystallography
series Acta Crystallographica Section E
issn 1600-5368
publishDate 2008-09-01
description The bis-Schiff base title compound, C20H16N2O4·C7H8, crystallized as a toluene solvate. In the solid state, it is present as its prototropic tautomer formed by transfer of one of the ortho-hydroxyl H atoms. The proton transfer is accompanied by a shift of electron pairs, as is evident from the observed C—O and C—N bond distances of 1.305 (2) and 1.315 (2) Å, which are largely consistent with C=O and C—N distances. The actual molecule present in the solid state is thus the charge-neutral β-keto amine, with a small contribution of its zwitterionic valence tautomer via partial delocalization of electron pairs along the N—C—C—C—O atom chain. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 51.99 (8) and 12.95 (9)°. Intramolecular O—H...N and N—H...O hydrogen bonds generate S(6) ring motifs, whereas intramolecular N—H...N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O—H...O hydrogen bonds and weak C—H...O interactions link the molecules into one-dimensional zigzag chains along the b axis; these chains are further stacked by O—H...O and weak C—H...O interactions along the c axis, forming two-dimensional extended networks parallel to the bc plane. In addition, the crystal structure is further stabilized by weak C—H...π and π–π interactions.
url http://scripts.iucr.org/cgi-bin/paper?S1600536808026305
work_keys_str_mv AT hasanzargoshi z62e24dihydroxybenzylideneaminophenylaminomethylene3hydroxycyclohexa24dienonetoluenesolvate
AT valiollahmirkhani z62e24dihydroxybenzylideneaminophenylaminomethylene3hydroxycyclohexa24dienonetoluenesolvate
AT rezakia z62e24dihydroxybenzylideneaminophenylaminomethylene3hydroxycyclohexa24dienonetoluenesolvate
AT hoongkunfun z62e24dihydroxybenzylideneaminophenylaminomethylene3hydroxycyclohexa24dienonetoluenesolvate
_version_ 1725247557500665856