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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...

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Detalles Bibliográficos
Autores principales: Tan, Daniel Teoh-Chuan, Osman, Hasnah, Kamaruddin, Azlina Harun, Kia, Reza, Fun, Hoong-Kun
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
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.
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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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