Cargando…
Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate
The bis(anil) molecule of the title compound, C(47)H(32)N(2)O(2)·C(6)H(4)Cl(2), contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H⋯N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)°...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7534250/ https://www.ncbi.nlm.nih.gov/pubmed/33117567 http://dx.doi.org/10.1107/S2056989020012104 |
_version_ | 1783590280695382016 |
---|---|
author | Wodajo, Ayalew Tskhovrebov, Alexander G. Le, Tuan Anh Kubasov, Alexey S. Grishina, Maria M. Krutius, Oleg N. Khrustalev, Victor N. |
author_facet | Wodajo, Ayalew Tskhovrebov, Alexander G. Le, Tuan Anh Kubasov, Alexey S. Grishina, Maria M. Krutius, Oleg N. Khrustalev, Victor N. |
author_sort | Wodajo, Ayalew |
collection | PubMed |
description | The bis(anil) molecule of the title compound, C(47)H(32)N(2)O(2)·C(6)H(4)Cl(2), contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H⋯N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C—H⋯O interactions. The dimers arrange in a one-dimensional column along the b axis via another C—H⋯O interaction and a π–π stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) Å. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—H⋯Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-l-gulonate decarboxylase and glutathione thiolesterase. |
format | Online Article Text |
id | pubmed-7534250 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-75342502020-10-27 Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate Wodajo, Ayalew Tskhovrebov, Alexander G. Le, Tuan Anh Kubasov, Alexey S. Grishina, Maria M. Krutius, Oleg N. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications The bis(anil) molecule of the title compound, C(47)H(32)N(2)O(2)·C(6)H(4)Cl(2), contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H⋯N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C—H⋯O interactions. The dimers arrange in a one-dimensional column along the b axis via another C—H⋯O interaction and a π–π stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) Å. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—H⋯Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-l-gulonate decarboxylase and glutathione thiolesterase. International Union of Crystallography 2020-09-04 /pmc/articles/PMC7534250/ /pubmed/33117567 http://dx.doi.org/10.1107/S2056989020012104 Text en © Wodajo et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Wodajo, Ayalew Tskhovrebov, Alexander G. Le, Tuan Anh Kubasov, Alexey S. Grishina, Maria M. Krutius, Oleg N. Khrustalev, Victor N. Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
title | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
title_full | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
title_fullStr | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
title_full_unstemmed | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
title_short | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
title_sort | crystal structure of 1,1′-{(1e,1′e)-[4,4′-(9h-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7534250/ https://www.ncbi.nlm.nih.gov/pubmed/33117567 http://dx.doi.org/10.1107/S2056989020012104 |
work_keys_str_mv | AT wodajoayalew crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate AT tskhovrebovalexanderg crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate AT letuananh crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate AT kubasovalexeys crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate AT grishinamariam crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate AT krutiusolegn crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate AT khrustalevvictorn crystalstructureof111e1e449hfluorene99diylbis41phenylenebisazanylylidenebismethanylylidenebisnaphthalen2oldichlorobenzenemonosolvate |