Cargando…

1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)

In the solid state the title Schiff base, 0.58C(28)H(20)N(2)O(2)·0.42C(28)H(20)N(2)O(2), exists both as the keto–imino and as the enol–amino tautomer, which is manifested in the disorder of the H atom in the intra­molecular hydrogen-bonded ring. The naphthalene ring systems show some distortion, whi...

Descripción completa

Detalles Bibliográficos
Autores principales: Blagus, Anita, Kaitner, Branko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247324/
https://www.ncbi.nlm.nih.gov/pubmed/22219942
http://dx.doi.org/10.1107/S1600536811040918
_version_ 1782220081126703104
author Blagus, Anita
Kaitner, Branko
author_facet Blagus, Anita
Kaitner, Branko
author_sort Blagus, Anita
collection PubMed
description In the solid state the title Schiff base, 0.58C(28)H(20)N(2)O(2)·0.42C(28)H(20)N(2)O(2), exists both as the keto–imino and as the enol–amino tautomer, which is manifested in the disorder of the H atom in the intra­molecular hydrogen-bonded ring. The naphthalene ring systems show some distortion, which is consistent with the quinoid effect. The ratio of the enol form refined to 58 (5)%. The mol­ecule has crystallographically imposed symmetry: a twofold axis passes through the central benzene ring. Crystals are built up of layers parallel to (010). Stacking interactions between the layers involve only standard van der Waals attraction forces between apolar groups. The alignment of the aromatic rings in neighbouring layers shows a herringbone motif. A weak C—H⋯O inter­action is observed.
format Online
Article
Text
id pubmed-3247324
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-32473242012-01-04 1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42) Blagus, Anita Kaitner, Branko Acta Crystallogr Sect E Struct Rep Online Organic Papers In the solid state the title Schiff base, 0.58C(28)H(20)N(2)O(2)·0.42C(28)H(20)N(2)O(2), exists both as the keto–imino and as the enol–amino tautomer, which is manifested in the disorder of the H atom in the intra­molecular hydrogen-bonded ring. The naphthalene ring systems show some distortion, which is consistent with the quinoid effect. The ratio of the enol form refined to 58 (5)%. The mol­ecule has crystallographically imposed symmetry: a twofold axis passes through the central benzene ring. Crystals are built up of layers parallel to (010). Stacking interactions between the layers involve only standard van der Waals attraction forces between apolar groups. The alignment of the aromatic rings in neighbouring layers shows a herringbone motif. A weak C—H⋯O inter­action is observed. International Union of Crystallography 2011-10-12 /pmc/articles/PMC3247324/ /pubmed/22219942 http://dx.doi.org/10.1107/S1600536811040918 Text en © Blagus and Kaitner 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Blagus, Anita
Kaitner, Branko
1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)
title 1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)
title_full 1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)
title_fullStr 1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)
title_full_unstemmed 1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)
title_short 1,1′-[m-Phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1H)-one (0.58/0.42)
title_sort 1,1′-[m-phenyl­enebis(nitrilo­methanylyl­idene)]dinaphthalen-2-ol–1,1′-[m-phenyl­enebis(imino­methanylyl­idene)]dinaphthalen-2(1h)-one (0.58/0.42)
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247324/
https://www.ncbi.nlm.nih.gov/pubmed/22219942
http://dx.doi.org/10.1107/S1600536811040918
work_keys_str_mv AT blagusanita 11mphenylenebisnitrilomethanylylidenedinaphthalen2ol11mphenylenebisiminomethanylylidenedinaphthalen21hone058042
AT kaitnerbranko 11mphenylenebisnitrilomethanylylidenedinaphthalen2ol11mphenylenebisiminomethanylylidenedinaphthalen21hone058042