(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...
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International Union of Crystallography
2008-09-01
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Series: | Acta Crystallographica Section E |
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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 |