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The crystal structures of the title adamantane-oxa-diazole 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-oxa-diazole unit. The mol-ecular 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, mol-ecules 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 inter-actions, forming slabs lying parallel to the bc plane. In (II), the dimers are linked by C-H⋯π and offset π-π inter-actions [inter-planar distance = 3.4039 (9) Å], forming layers parallel to (10).

acta crystallographica. section e, crystallographic communications

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