Cycloalkanes and cycloalkenes in dispersive force oriented inclusion crystals by a functionalized acyclic host molecule

Abstract

A disubstituted adamantane derivative bearing chloropyrimidine units (1) was synthesized as an acyclic host molecule to construct guest-inclusion crystalline materials, and the molecular structures of these crystalline materials were determined by X-ray crystallographic analysis. The crystallization of 1 and trans-decahydronaphthalene (a) in chloroform afforded co-crystal (1a) with 2 : 1 host : guest complexation stoichiometry. The guest molecule was accommodated within the cavity of the cyclic dimers of 1 built from Cl⋯π interactions between the chloropyrimidine units. These complexes were assembled into network structures through intermolecular interactions. From the Hirshfeld surface analysis and the 2D fingerprint plot of a in co-crystal 1a, the maximum contribution is from the H⋯H contacts between 1 and a, indicating that the main driving force for the guest inclusion is dispersive force. Co-crystals containing cycloalkanes and cycloalkenes (b–f) and having the same stoichiometry were obtained under identical conditions. In all the co-crystals, the shapes and sizes of the cyclic dimers and the molecular networks were similar to those of crystal 1a, and the molecular structures of the guests were characterized.