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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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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 |
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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 |
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