Synthesis of 1,1′-(2,6-dihydroxy-2,6-dimethyl-3,7-dioxabicyclo [3.3.1]nonane-1,5-diyl)diethanone dihydrate: crystal structure and quantitative analysis of molecular interaction via molecular electrostatic potential and Hirshfeld surface analysis

Abstract

ABSTRACTA new bicyclononane derivative, 1,1′-(2,6-dihydroxy-2,6-dimethyl-3,7-dioxa-bicyclo[3.3.1]nonane-1,5-diyl) diethanone dihydrate (1), has been synthesized and structurally characterized by the single-crystal X-ray diffraction technique. In the solid-state structure of the compound, molecular units are interlinked via strong hydrogen bonds as well as non-classical weak hydrogen bonds leading to a three-dimensional supramolecular architecture. Solid-state DFT optimized geometry in (1) agrees closely with that obtained from the crystallographic analysis. The C(dioxa-bicyclononane)–H … O(hydroxy) hydrogen bond generates cyclic (10) ring in (1) which are further connected through C–H … O and O–H … O hydrogen bonds into a three-dimensional framework in the title compound. Hirshfeld surface analysis of the title compound along with some related nonane derivatives retrieved from the Cambridge Structural Database shows that the most of the Hirshfeld surface area in this class of compounds is due to H … H and O … H interactions.