Supramolecular hydrogen-bonding patterns in 4′-substituted cyclohexane-5-spirohydantoin

Abstract

The preparation and single crystal structures of five derivatives of cyclohexane-5-spirohydantoin are described. A detailed analysis of Hirshfeld surfaces through the 2-D fingerprints has been carried out to facilitate comparison of the interactions established in the different structures. The derivatives of cyclohexane-5-spirohydantoin are characterized by the presence of cyclohexane-linked aromatic derivatives at position C4′, with this ring attached either directly or by different functional groups such as ethers or esters. The configuration of 1, 2, 4 and 5, as determined by X-ray diffraction, is cis while compound 3 is trans. All compounds have a Bucherer–Berg orientation of the hydantoin ring. In the Cambridge Structural Database (CSD) previous examples of 5-spirohydantoins with a trans configuration were not found. The crystal structures are compared with those previously described in the Cambridge Structural Database (CSD) and are classified according to the interactions between the hydantoin rings. Four types of structures are described, dimers and ribbons, which are common in hydantoin derivatives, and R₃³(10) and R₆⁶(26) supramolecular synthons, which are unprecedented in the literature.