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Combining X\u2010ray crystallography and vibrational spectroscopy, along with Hirshfeld surface analysis and calculations (CE\u2010B3LYP\/6\u201031G(d,p)) of pairwise interaction energies of intermolecular contacts existing in the crystal structure, may deepen the understanding of relative reactivity and properties of these endoperoxides classes. In the crystal, the tetraoxane ring in <jats:bold>2<\/jats:bold> and the trioxolane\u2010adamantyl fragment in <jats:bold>1<\/jats:bold> are disordered, with molecules <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> existing as two distinct, stable conformations. Whereas the dominant C\u2212H\u22c5\u22c5\u22c5O H\u2010bonds in <jats:bold>1<\/jats:bold> connect an adamantyl C\u2212H and O1 or O2 of the trioxolane ring, in <jats:bold>2<\/jats:bold> they involve the carbonyl oxygen, acting as a double acceptor from phenyl ring C\u2212H groups. C\u2212H\u22c5\u22c5\u22c5O and C\u2212H\u22c5\u22c5\u22c5\u03c0 H\u2010bonds define the molecular packing of <jats:bold>2<\/jats:bold>, while C\u2212H\u22c5\u22c5\u22c5H\u2212C van der Waals interactions determine the packing of <jats:bold>1<\/jats:bold>. The dispersive component dominates the interaction energies calculated for the most representative molecular pairs.<\/jats:p>","DOI":"10.1002\/cplu.202200207","type":"journal-article","created":{"date-parts":[[2022,8,10]],"date-time":"2022-08-10T15:58:02Z","timestamp":1660147082000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Unravelling the Structure of Peroxides with Antiparasitic Activity: The Relative Impact of a Trioxolane or a Tetraoxane Pharmacophore on the Overall Molecular Structure"],"prefix":"10.1002","volume":"87","author":[{"given":"Patr\u00edcia S. 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