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Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
The title compound, C(29)H(33)NO(3), crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyrid...
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/PMC9361379/ https://www.ncbi.nlm.nih.gov/pubmed/35974826 http://dx.doi.org/10.1107/S2056989022007022 |
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author | Yıldırım, Sema Öztürk Akkurt, Mehmet Çetin, Gökalp Şimşek, Rahime Butcher, Ray J. Bhattarai, Ajaya |
author_facet | Yıldırım, Sema Öztürk Akkurt, Mehmet Çetin, Gökalp Şimşek, Rahime Butcher, Ray J. Bhattarai, Ajaya |
author_sort | Yıldırım, Sema Öztürk |
collection | PubMed |
description | The title compound, C(29)H(33)NO(3), crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyridine ring adopts a distorted boat conformation. The cyclohexene ring has an envelope conformation in molecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered molecule C. In the crystal, molecules are linked by C—H⋯O and N—H⋯O hydrogen bonds, forming layers parallel to (100) defining R (1) (4)(6) and C(7) graph-set motifs. Additional C—H⋯π interactions consolidate the layered structure. Between the layers, van der Waals interactions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H⋯H (69.6% in A, 69.9% in B, 70.1% in C), C⋯H/H⋯C (20.3% in A, 20.6% in B, 20.3% in C) and O⋯H/H⋯O (8.6% in A, 8.6% in B, 8.4% in C) interactions. |
format | Online Article Text |
id | pubmed-9361379 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-93613792022-08-15 Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate Yıldırım, Sema Öztürk Akkurt, Mehmet Çetin, Gökalp Şimşek, Rahime Butcher, Ray J. Bhattarai, Ajaya Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(29)H(33)NO(3), crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyridine ring adopts a distorted boat conformation. The cyclohexene ring has an envelope conformation in molecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered molecule C. In the crystal, molecules are linked by C—H⋯O and N—H⋯O hydrogen bonds, forming layers parallel to (100) defining R (1) (4)(6) and C(7) graph-set motifs. Additional C—H⋯π interactions consolidate the layered structure. Between the layers, van der Waals interactions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H⋯H (69.6% in A, 69.9% in B, 70.1% in C), C⋯H/H⋯C (20.3% in A, 20.6% in B, 20.3% in C) and O⋯H/H⋯O (8.6% in A, 8.6% in B, 8.4% in C) interactions. International Union of Crystallography 2022-07-14 /pmc/articles/PMC9361379/ /pubmed/35974826 http://dx.doi.org/10.1107/S2056989022007022 Text en © Yıldırım 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 Yıldırım, Sema Öztürk Akkurt, Mehmet Çetin, Gökalp Şimşek, Rahime Butcher, Ray J. Bhattarai, Ajaya Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
title | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
title_full | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
title_fullStr | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
title_full_unstemmed | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
title_short | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
title_sort | synthesis, characterization, crystal structure and hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361379/ https://www.ncbi.nlm.nih.gov/pubmed/35974826 http://dx.doi.org/10.1107/S2056989022007022 |
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