Abstract
The crystal structures of the title adamantane-oxa-diazole 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-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).
Highlights
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 1,3,4oxadiazole unit
In the crystals of both compounds, molecules are linked by pairs of C—HÁ Á ÁN hydrogen bonds, forming inversion dimers with R22(12) ring motifs
In (I) the dimers are connected by C—HÁ Á ÁF interactions, forming slabs lying parallel to the bc plane
Summary
Considerable attention has been devoted to adamantane derivatives, which have long been known for their diverse biological properties (Liu et al, 2011; Lamoureux & Artavia, 2010). The C—N bonds in the oxadiazole rings have double-bond character [C7 N1 = 1.279 (5) and 1.292 (3) A , and C8 N2 = 1.288 (5) and 1.288 (3) Ain (I) and (II), respectively], while the N—N and C—O bonds exhibit single-bond character [N1—N2 = 1.408 (4) and 1.417 (3) A , C7—O1 = 1.366 (4) and 1.360 (2) A , and C8—O1 = 1.369 (4) and 1.359 (2) Ain (I) and (II), respectively]. In compound (II), the rings are almost coplanar with their mean planes being inclined to each other by 9.5 (1), while in compound (I) the equivalent dihedral angle is 20.8 (2)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have