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Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid
The title cyclobutyl compound, C(18)H(18)N(2)O(3)S, was synthesized by the interaction of 4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine and maleic anhydride, and crystallizes in the orthorhombic space group P2(1)2(1)2(1) with Z′ = 1. The molecular geometry is partially stabilized by an int...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8819446/ https://www.ncbi.nlm.nih.gov/pubmed/35145736 http://dx.doi.org/10.1107/S2056989022000032 |
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author | Simsek, Okan Dincer, Muharrem Dege, Necmi Saif, Eiad Yilmaz, Ibrahim Cukurovali, Alaaddin |
author_facet | Simsek, Okan Dincer, Muharrem Dege, Necmi Saif, Eiad Yilmaz, Ibrahim Cukurovali, Alaaddin |
author_sort | Simsek, Okan |
collection | PubMed |
description | The title cyclobutyl compound, C(18)H(18)N(2)O(3)S, was synthesized by the interaction of 4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine and maleic anhydride, and crystallizes in the orthorhombic space group P2(1)2(1)2(1) with Z′ = 1. The molecular geometry is partially stabilized by an intramolecular N—H⋯O hydrogen bond forming an S (1) (1)(7) ring motif. The molecule is non-planar with a dihedral angle of 88.29 (11)° between the thiazole and benzene rings. In the crystal, the molecules are linked by O—H⋯N hydrogen bonds, forming supramolecular ribbons with C (1) (1)(9) chain motifs. To further analyze the intermolecular interactions, a Hirshfeld surface analysis was performed. The results indicate that the most important contributions to the overall surface are from H⋯H (43%), C⋯H (18%), O⋯H (17%) and N⋯H (6%), interactions. |
format | Online Article Text |
id | pubmed-8819446 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-88194462022-02-09 Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid Simsek, Okan Dincer, Muharrem Dege, Necmi Saif, Eiad Yilmaz, Ibrahim Cukurovali, Alaaddin Acta Crystallogr E Crystallogr Commun Research Communications The title cyclobutyl compound, C(18)H(18)N(2)O(3)S, was synthesized by the interaction of 4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine and maleic anhydride, and crystallizes in the orthorhombic space group P2(1)2(1)2(1) with Z′ = 1. The molecular geometry is partially stabilized by an intramolecular N—H⋯O hydrogen bond forming an S (1) (1)(7) ring motif. The molecule is non-planar with a dihedral angle of 88.29 (11)° between the thiazole and benzene rings. In the crystal, the molecules are linked by O—H⋯N hydrogen bonds, forming supramolecular ribbons with C (1) (1)(9) chain motifs. To further analyze the intermolecular interactions, a Hirshfeld surface analysis was performed. The results indicate that the most important contributions to the overall surface are from H⋯H (43%), C⋯H (18%), O⋯H (17%) and N⋯H (6%), interactions. International Union of Crystallography 2022-01-07 /pmc/articles/PMC8819446/ /pubmed/35145736 http://dx.doi.org/10.1107/S2056989022000032 Text en © Simsek et al. 2022 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 Simsek, Okan Dincer, Muharrem Dege, Necmi Saif, Eiad Yilmaz, Ibrahim Cukurovali, Alaaddin Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
title | Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
title_full | Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
title_fullStr | Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
title_short | Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
title_sort | crystal structure and hirshfeld surface analysis of (z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8819446/ https://www.ncbi.nlm.nih.gov/pubmed/35145736 http://dx.doi.org/10.1107/S2056989022000032 |
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