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...

Full description

Bibliographic Details
Main Authors: Lamya H. Al-Wahaibi, Aisha Alsfouk, Ali A. El-Emam, Olivier Blacque
Format: Article
Language:English
Published: International Union of Crystallography 2019-05-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989019004651
id doaj-7eb5097d97e34b61a72aa4ef2743a6a8
record_format Article
spelling 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
_version_ 1725231626006298624