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Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
The crystal structures of the title adamantane-oxadiazole hybrid compounds, C(18)H(19)FN(2)O (I) and C(18)H(19)ClN(2)O (II), are built up from an adamantane unit and a halogenophenyl ring, [X = F (I), Cl (II)], in position 5 on the central 1,3,4-oxadiazole unit. The molecular structures are very...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6505599/ https://www.ncbi.nlm.nih.gov/pubmed/31110797 http://dx.doi.org/10.1107/S2056989019004651 |
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author | Al-Wahaibi, Lamya H. Alsfouk, Aisha El-Emam, Ali A. Blacque, Olivier |
author_facet | Al-Wahaibi, Lamya H. Alsfouk, Aisha El-Emam, Ali A. Blacque, Olivier |
author_sort | Al-Wahaibi, Lamya H. |
collection | PubMed |
description | The crystal structures of the title adamantane-oxadiazole hybrid compounds, C(18)H(19)FN(2)O (I) and C(18)H(19)ClN(2)O (II), are built up from an adamantane unit and a halogenophenyl ring, [X = F (I), Cl (II)], in position 5 on the central 1,3,4-oxadiazole unit. The molecular structures are very similar, only the relative orientation of the halogenophenyl ring in comparison with the central five-membered ring differs slightly. In the crystals of both compounds, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers with R (2) (2)(12) ring motifs. In (I) the dimers are connected by C—H⋯F interactions, forming slabs lying parallel to the bc plane. In (II), the dimers are linked by C—H⋯π and offset π–π interactions [interplanar distance = 3.4039 (9) Å], forming layers parallel to (10[Image: see text]). |
format | Online Article Text |
id | pubmed-6505599 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-65055992019-05-20 Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole Al-Wahaibi, Lamya H. Alsfouk, Aisha El-Emam, Ali A. Blacque, Olivier Acta Crystallogr E Crystallogr Commun Research Communications The crystal structures of the title adamantane-oxadiazole hybrid compounds, C(18)H(19)FN(2)O (I) and C(18)H(19)ClN(2)O (II), are built up from an adamantane unit and a halogenophenyl ring, [X = F (I), Cl (II)], in position 5 on the central 1,3,4-oxadiazole unit. The molecular structures are very similar, only the relative orientation of the halogenophenyl ring in comparison with the central five-membered ring differs slightly. In the crystals of both compounds, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers with R (2) (2)(12) ring motifs. In (I) the dimers are connected by C—H⋯F interactions, forming slabs lying parallel to the bc plane. In (II), the dimers are linked by C—H⋯π and offset π–π interactions [interplanar distance = 3.4039 (9) Å], forming layers parallel to (10[Image: see text]). International Union of Crystallography 2019-04-12 /pmc/articles/PMC6505599/ /pubmed/31110797 http://dx.doi.org/10.1107/S2056989019004651 Text en © Al-Wahaibi et al. 2019 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 Al-Wahaibi, Lamya H. Alsfouk, Aisha El-Emam, Ali A. Blacque, Olivier Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
title | Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
title_full | Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
title_fullStr | Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
title_full_unstemmed | Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
title_short | Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
title_sort | crystal structures and hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6505599/ https://www.ncbi.nlm.nih.gov/pubmed/31110797 http://dx.doi.org/10.1107/S2056989019004651 |
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