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Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol
The title compound, C(13)H(14)N(4)O, was developed using the reaction of salicylaldehyde and 3-amino-5-cyclobutyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8647728/ https://www.ncbi.nlm.nih.gov/pubmed/34925895 http://dx.doi.org/10.1107/S2056989021011658 |
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author | Gumus, Mustafa Kemal Sen, Fatih Kansiz, Sevgi Dege, Necmi Saif, Eiad |
author_facet | Gumus, Mustafa Kemal Sen, Fatih Kansiz, Sevgi Dege, Necmi Saif, Eiad |
author_sort | Gumus, Mustafa Kemal |
collection | PubMed |
description | The title compound, C(13)H(14)N(4)O, was developed using the reaction of salicylaldehyde and 3-amino-5-cyclobutyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol in good yields and purity. The title compound is a Schiff base that exists in the phenol–imine tautomeric form and adopts an E configuration. The three independent molecules in the asymmetric unit (A, B and C) are not planar, the cyclobutyl and the phenol-imine rings are twisted to each other making a dihedral angle of 67.8 (4)° in molecule A, 69.1 (2)° in molecule B and 89.1 (2)° in molecule C. In each molecule an intramolecular O—H⋯N hydrogen bond is present, forming an S(6) ring motif. A Hirshfeld surface analysis was performed to investigate the contributions of the different intermolecular contacts within the supramolecular structure. The major interactions are H⋯H (53%), C⋯H (19%) and N⋯H (17%) for molecule A, H⋯H (50%), N⋯H (20%) and C⋯H (20%) for molecule B and H⋯H (57%), C⋯H (14%) and N⋯H (13%) for molecule C. |
format | Online Article Text |
id | pubmed-8647728 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-86477282021-12-16 Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol Gumus, Mustafa Kemal Sen, Fatih Kansiz, Sevgi Dege, Necmi Saif, Eiad Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(13)H(14)N(4)O, was developed using the reaction of salicylaldehyde and 3-amino-5-cyclobutyl-1,2,4-triazole in ethanol under microwave irradiation. This eco-friendly microwave-promoted method proved to be efficient in the synthesis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol in good yields and purity. The title compound is a Schiff base that exists in the phenol–imine tautomeric form and adopts an E configuration. The three independent molecules in the asymmetric unit (A, B and C) are not planar, the cyclobutyl and the phenol-imine rings are twisted to each other making a dihedral angle of 67.8 (4)° in molecule A, 69.1 (2)° in molecule B and 89.1 (2)° in molecule C. In each molecule an intramolecular O—H⋯N hydrogen bond is present, forming an S(6) ring motif. A Hirshfeld surface analysis was performed to investigate the contributions of the different intermolecular contacts within the supramolecular structure. The major interactions are H⋯H (53%), C⋯H (19%) and N⋯H (17%) for molecule A, H⋯H (50%), N⋯H (20%) and C⋯H (20%) for molecule B and H⋯H (57%), C⋯H (14%) and N⋯H (13%) for molecule C. International Union of Crystallography 2021-11-09 /pmc/articles/PMC8647728/ /pubmed/34925895 http://dx.doi.org/10.1107/S2056989021011658 Text en © Gumus et al. 2021 https://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. |
spellingShingle | Research Communications Gumus, Mustafa Kemal Sen, Fatih Kansiz, Sevgi Dege, Necmi Saif, Eiad Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol |
title | Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol |
title_full | Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol |
title_fullStr | Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol |
title_short | Crystal structure and Hirshfeld surface analysis of 2-{[(E)-(3-cyclobutyl-1H-1,2,4-triazol-5-yl)imino]methyl}phenol |
title_sort | crystal structure and hirshfeld surface analysis of 2-{[(e)-(3-cyclobutyl-1h-1,2,4-triazol-5-yl)imino]methyl}phenol |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8647728/ https://www.ncbi.nlm.nih.gov/pubmed/34925895 http://dx.doi.org/10.1107/S2056989021011658 |
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