Crystal structure, Hirshfeld surface analysis and DFT studies of Euphorbioside monohydrate a major bisnorsesquiterpene isolated from Euphorbia resinifera latex

The structure of this new derivative of Euphorbioside [systematic name: (1S,2R,3R,5R,8R)-8-((R,E)-3-hydroxybut-1-en-1-yl)-1,5-dimethyl-6-oxabicyclo[3.2.1]octane-2,3-diol hydrate] was determined by its single-crystal X-ray structure, and to studies with the use of NMR, LC/HRMS and IR spectra. The title compound is built up from two fused five- and six-membered rings, with an additional hydroxybut-1-en-1-yl group and water molecule. The five-membered ring, which has an envelope conformation, makes dihedral angles of 77.46(13)degrees with the benzene ring. The water molecule forms O-H center dot center dot center dot O hydrogen bond. In the crystal, intermolecular O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds lead to the formation of three-dimensional framework. The nature of intermolecular interactions in the supramolecular structure Hirshfeld surface analysis and 2D fingerprint was carried out. The most important contributions for the crystal packing are from H center dot center dot center dot H (75.2%) and O center dot center dot center dot H/H center dot center dot center dot O (24.6%) interactions. Additionally, DFT calculations have been used to analyze the electronic and geometric frontier molecular orbital, Molecular Electrostatic Potential map analyses, Mulliken and Natural bond charges were produced by using the optimized structures. (C) 2021 Elsevier B.V. All rights reserved.