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Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol)
In the title unsymmetrical tertiary amine, C(24)H(33)NO(2), which arose from the ring-opening reaction of a dihydrobenzoxazine, two 2,4-dimethylphenol moieties are linked by a 6,6′-(cyclohexylazanediyl)-bis(methylene) bridge: the dihedral angle between the dimethylphenol rings is 72.45 (7...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7405559/ https://www.ncbi.nlm.nih.gov/pubmed/32844006 http://dx.doi.org/10.1107/S2056989020009184 |
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author | Wannapaiboon, Suttipong Hanlumyuang, Yuranan Chansaenpak, Kantapat Pinyou, Piyanut Veranitisagul, Chatchai Laobuthee, Apirat Wattanathana, Worawat |
author_facet | Wannapaiboon, Suttipong Hanlumyuang, Yuranan Chansaenpak, Kantapat Pinyou, Piyanut Veranitisagul, Chatchai Laobuthee, Apirat Wattanathana, Worawat |
author_sort | Wannapaiboon, Suttipong |
collection | PubMed |
description | In the title unsymmetrical tertiary amine, C(24)H(33)NO(2), which arose from the ring-opening reaction of a dihydrobenzoxazine, two 2,4-dimethylphenol moieties are linked by a 6,6′-(cyclohexylazanediyl)-bis(methylene) bridge: the dihedral angle between the dimethylphenol rings is 72.45 (7)°. The cyclohexyl ring adopts a chair conformation with the exocyclic C—N bond in an equatorial orientation. One of the phenol OH groups forms an intramolecular O—H⋯N hydrogen bond, generating an S(6) ring, and a short intramolecular C—H⋯O contact is also present. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(10) chains propagating along the [100] direction. The Hirshfeld surface analysis of the title compound confirms the presence of these intra- and intermolecular interactions. The corresponding fingerprint plots indicate that the most significant contacts in the crystal packing are H⋯H (76.4%), H⋯C/C⋯H (16.3%), and H⋯O/O⋯H (7.2%). |
format | Online Article Text |
id | pubmed-7405559 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-74055592020-08-24 Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) Wannapaiboon, Suttipong Hanlumyuang, Yuranan Chansaenpak, Kantapat Pinyou, Piyanut Veranitisagul, Chatchai Laobuthee, Apirat Wattanathana, Worawat Acta Crystallogr E Crystallogr Commun Research Communications In the title unsymmetrical tertiary amine, C(24)H(33)NO(2), which arose from the ring-opening reaction of a dihydrobenzoxazine, two 2,4-dimethylphenol moieties are linked by a 6,6′-(cyclohexylazanediyl)-bis(methylene) bridge: the dihedral angle between the dimethylphenol rings is 72.45 (7)°. The cyclohexyl ring adopts a chair conformation with the exocyclic C—N bond in an equatorial orientation. One of the phenol OH groups forms an intramolecular O—H⋯N hydrogen bond, generating an S(6) ring, and a short intramolecular C—H⋯O contact is also present. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(10) chains propagating along the [100] direction. The Hirshfeld surface analysis of the title compound confirms the presence of these intra- and intermolecular interactions. The corresponding fingerprint plots indicate that the most significant contacts in the crystal packing are H⋯H (76.4%), H⋯C/C⋯H (16.3%), and H⋯O/O⋯H (7.2%). International Union of Crystallography 2020-07-10 /pmc/articles/PMC7405559/ /pubmed/32844006 http://dx.doi.org/10.1107/S2056989020009184 Text en © Wannapaiboon 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 Wannapaiboon, Suttipong Hanlumyuang, Yuranan Chansaenpak, Kantapat Pinyou, Piyanut Veranitisagul, Chatchai Laobuthee, Apirat Wattanathana, Worawat Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
title | Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
title_full | Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
title_fullStr | Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
title_short | Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
title_sort | crystal structure and hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol) |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7405559/ https://www.ncbi.nlm.nih.gov/pubmed/32844006 http://dx.doi.org/10.1107/S2056989020009184 |
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