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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...

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Autores principales: Al-Wahaibi, Lamya H., Alsfouk, Aisha, El-Emam, Ali A., Blacque, Olivier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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]).
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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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