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5-Hydroxy-8-nitro-1,4-naphthoquinone
The title compound, C(10)H(5)NO(5), features an intramolecular O—H⋯O hydrogen bond, forming a six-membered ring with an S(6) ring motif. The nitro group makes a dihedral angle of 71.66 (5)° with the plane of the benzene ring to which it is bound. The two rings are almost coplanar, with a dihedral a...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962149/ https://www.ncbi.nlm.nih.gov/pubmed/21203231 http://dx.doi.org/10.1107/S1600536808021594 |
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author | Tan, Daniel Teoh-Chuan Osman, Hasnah Kamaruddin, Azlina Harun Kia, Reza Fun, Hoong-Kun |
author_facet | Tan, Daniel Teoh-Chuan Osman, Hasnah Kamaruddin, Azlina Harun Kia, Reza Fun, Hoong-Kun |
author_sort | Tan, Daniel Teoh-Chuan |
collection | PubMed |
description | The title compound, C(10)H(5)NO(5), features an intramolecular O—H⋯O hydrogen bond, forming a six-membered ring with an S(6) ring motif. The nitro group makes a dihedral angle of 71.66 (5)° with the plane of the benzene ring to which it is bound. The two rings are almost coplanar, with a dihedral angle of 4.44 (5)°. Short intermolecular distances between the centroids of the six-membered rings [3.7188 (6)–3.8299 (6) Å] indicate the existence of π–π interactions. The interesting features of the crystal structure are the short intermolecular O⋯O and O⋯N interactions. The crystal packing is stabilized by intramolecular O—H⋯O and intermolecular C—H⋯O (×3) hydrogen bonds, and C—H⋯π interactions. |
format | Text |
id | pubmed-2962149 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29621492010-12-30 5-Hydroxy-8-nitro-1,4-naphthoquinone Tan, Daniel Teoh-Chuan Osman, Hasnah Kamaruddin, Azlina Harun Kia, Reza Fun, Hoong-Kun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(10)H(5)NO(5), features an intramolecular O—H⋯O hydrogen bond, forming a six-membered ring with an S(6) ring motif. The nitro group makes a dihedral angle of 71.66 (5)° with the plane of the benzene ring to which it is bound. The two rings are almost coplanar, with a dihedral angle of 4.44 (5)°. Short intermolecular distances between the centroids of the six-membered rings [3.7188 (6)–3.8299 (6) Å] indicate the existence of π–π interactions. The interesting features of the crystal structure are the short intermolecular O⋯O and O⋯N interactions. The crystal packing is stabilized by intramolecular O—H⋯O and intermolecular C—H⋯O (×3) hydrogen bonds, and C—H⋯π interactions. International Union of Crystallography 2008-07-19 /pmc/articles/PMC2962149/ /pubmed/21203231 http://dx.doi.org/10.1107/S1600536808021594 Text en © Tan et al. 2008 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 Tan, Daniel Teoh-Chuan Osman, Hasnah Kamaruddin, Azlina Harun Kia, Reza Fun, Hoong-Kun 5-Hydroxy-8-nitro-1,4-naphthoquinone |
title | 5-Hydroxy-8-nitro-1,4-naphthoquinone |
title_full | 5-Hydroxy-8-nitro-1,4-naphthoquinone |
title_fullStr | 5-Hydroxy-8-nitro-1,4-naphthoquinone |
title_full_unstemmed | 5-Hydroxy-8-nitro-1,4-naphthoquinone |
title_short | 5-Hydroxy-8-nitro-1,4-naphthoquinone |
title_sort | 5-hydroxy-8-nitro-1,4-naphthoquinone |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962149/ https://www.ncbi.nlm.nih.gov/pubmed/21203231 http://dx.doi.org/10.1107/S1600536808021594 |
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