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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-...

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Autores principales: Gumus, Mustafa Kemal, Sen, Fatih, Kansiz, Sevgi, Dege, Necmi, Saif, Eiad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
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.
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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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