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, C18H19FN2O (I) and C18H19ClN2O (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 t...
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doaj-7eb5097d97e34b61a72aa4ef2743a6a82020-11-25T00:55:11ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-05-0175561161510.1107/S2056989019004651su5492Crystal 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-oxadiazoleLamya H. Al-Wahaibi0Aisha Alsfouk1Ali A. El-Emam2Olivier Blacque3Department of Chemistry, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi ArabiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EgyptDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, SwitzerlandThe crystal structures of the title adamantane-oxadiazole hybrid compounds, C18H19FN2O (I) and C18H19ClN2O (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 R22(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\overline{1}).http://scripts.iucr.org/cgi-bin/paper?S2056989019004651crystal structureadamantyl derivatives1,3,4-oxadiazolesC—H...N hydrogen bondsC—H...F interactionsHirshfeld surface analysis. |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Lamya H. Al-Wahaibi Aisha Alsfouk Ali A. El-Emam Olivier Blacque |
spellingShingle |
Lamya H. Al-Wahaibi Aisha Alsfouk Ali A. El-Emam Olivier Blacque 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 Acta Crystallographica Section E: Crystallographic Communications crystal structure adamantyl derivatives 1,3,4-oxadiazoles C—H...N hydrogen bonds C—H...F interactions Hirshfeld surface analysis. |
author_facet |
Lamya H. Al-Wahaibi Aisha Alsfouk Ali A. El-Emam Olivier Blacque |
author_sort |
Lamya H. Al-Wahaibi |
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_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_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_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 |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2019-05-01 |
description |
The crystal structures of the title adamantane-oxadiazole hybrid compounds, C18H19FN2O (I) and C18H19ClN2O (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 R22(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\overline{1}). |
topic |
crystal structure adamantyl derivatives 1,3,4-oxadiazoles C—H...N hydrogen bonds C—H...F interactions Hirshfeld surface analysis. |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989019004651 |
work_keys_str_mv |
AT lamyahalwahaibi crystalstructuresandhirshfeldsurfaceanalysisof2adamantan1yl54fluorophenyl134oxadiazoleand2adamantan1yl54chlorophenyl134oxadiazole AT aishaalsfouk crystalstructuresandhirshfeldsurfaceanalysisof2adamantan1yl54fluorophenyl134oxadiazoleand2adamantan1yl54chlorophenyl134oxadiazole AT aliaelemam crystalstructuresandhirshfeldsurfaceanalysisof2adamantan1yl54fluorophenyl134oxadiazoleand2adamantan1yl54chlorophenyl134oxadiazole AT olivierblacque crystalstructuresandhirshfeldsurfaceanalysisof2adamantan1yl54fluorophenyl134oxadiazoleand2adamantan1yl54chlorophenyl134oxadiazole |
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