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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...

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Autores principales: Wannapaiboon, Suttipong, Hanlumyuang, Yuranan, Chansaenpak, Kantapat, Pinyou, Piyanut, Veranitisagul, Chatchai, Laobuthee, Apirat, Wattanathana, Worawat
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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%).
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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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