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Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone
The title compound, C(9)H(10)O(3), is a bioactive secondary metabolite, isolated from the endophytic fungus Nodulisporium sp. The compound exhibits an intramolecular O—H⋯O hydrogen bond between the phenolic H atom and the carbonyl O atom of the adjacent acetyl group. In the crystal, molecules are...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571424/ https://www.ncbi.nlm.nih.gov/pubmed/26396824 http://dx.doi.org/10.1107/S2056989015013468 |
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author | Prabpai, Samran Kongsaeree, Palangpon |
author_facet | Prabpai, Samran Kongsaeree, Palangpon |
author_sort | Prabpai, Samran |
collection | PubMed |
description | The title compound, C(9)H(10)O(3), is a bioactive secondary metabolite, isolated from the endophytic fungus Nodulisporium sp. The compound exhibits an intramolecular O—H⋯O hydrogen bond between the phenolic H atom and the carbonyl O atom of the adjacent acetyl group. In the crystal, molecules are linked by hydrogen bonds involving the 4-phenolic H atom and a symmetry-related carbonyl O atom of a neighboring molecule, resulting in extended supramolecular chains along the a-axis direction. Aromatic π–π stacking interactions between the nearly parallel benzene rings of adjacent chains [centroid–centroid distance = 3.7478 (8) Å] further stabilize the three-dimensional supramolecular framework. |
format | Online Article Text |
id | pubmed-4571424 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45714242015-09-22 Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone Prabpai, Samran Kongsaeree, Palangpon Acta Crystallogr E Crystallogr Commun Data Reports The title compound, C(9)H(10)O(3), is a bioactive secondary metabolite, isolated from the endophytic fungus Nodulisporium sp. The compound exhibits an intramolecular O—H⋯O hydrogen bond between the phenolic H atom and the carbonyl O atom of the adjacent acetyl group. In the crystal, molecules are linked by hydrogen bonds involving the 4-phenolic H atom and a symmetry-related carbonyl O atom of a neighboring molecule, resulting in extended supramolecular chains along the a-axis direction. Aromatic π–π stacking interactions between the nearly parallel benzene rings of adjacent chains [centroid–centroid distance = 3.7478 (8) Å] further stabilize the three-dimensional supramolecular framework. International Union of Crystallography 2015-07-29 /pmc/articles/PMC4571424/ /pubmed/26396824 http://dx.doi.org/10.1107/S2056989015013468 Text en © Prabpai and Kongsaeree 2015 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 | Data Reports Prabpai, Samran Kongsaeree, Palangpon Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
title | Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
title_full | Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
title_fullStr | Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
title_full_unstemmed | Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
title_short | Crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
title_sort | crystal structure of 1-(2,4-dihydroxy-6-methylphenyl)ethanone |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571424/ https://www.ncbi.nlm.nih.gov/pubmed/26396824 http://dx.doi.org/10.1107/S2056989015013468 |
work_keys_str_mv | AT prabpaisamran crystalstructureof124dihydroxy6methylphenylethanone AT kongsaereepalangpon crystalstructureof124dihydroxy6methylphenylethanone |