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Vibrational spectroscopy (IR and Raman) reveals significant redshifts in the N\uf8ffH and C\uf8feO stretching bands, confirming the presence of strong intramolecular N\uf8ffH\u00b7\u00b7\u00b7O\uf8feC hydrogen bonds. Conformational analysis using molecular mechanics and DFT calculations identifies several conformers, with the most stable adopting an <jats:italic>S<\/jats:italic>\u2010shaped geometry where the C\uf8feO and C\uf8feS bonds are oppositely oriented\u2014a configuration that was experimentally validated by single\u2010crystal X\u2010ray diffraction. In the solid state, crystal packing is governed by hydrogen\u2010bonding interactions (H\u00b7\u00b7\u00b7O\uf8feC and H\u00b7\u00b7\u00b7S\uf8feC) facilitated by the acyl\u2010thiourea core. The bulky adamantyl\/noradamantyl groups impose steric constraints, whereas the halogenated phenyl rings promote stabilizing \u03c0\u2010stacking and halogen interactions. Biological evaluation demonstrates limited antimicrobial activity against <jats:italic>Escherichia coli<\/jats:italic>, <jats:italic>Pseudomonas aeruginosa<\/jats:italic>, <jats:italic>Burkholderia cenocepacia<\/jats:italic>, and <jats:italic>Staphylococcus aureus<\/jats:italic>, but moderate cytotoxicity against A549, 16HBE14o\u2010, and HaCaT cell lines (IC<jats:sub>50<\/jats:sub>\u2009=\u200925\u2013100\u2009\u03bcM).<\/jats:p>","DOI":"10.1002\/cplu.202500311","type":"journal-article","created":{"date-parts":[[2025,6,30]],"date-time":"2025-06-30T04:45:13Z","timestamp":1751258713000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Structural and Conformational Analysis and Biological Activity of Adamantyl\u2010Based Acyl\u2010Thioureas Bearing Trihalophenyl Substituents"],"prefix":"10.1002","volume":"90","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7915-0279","authenticated-orcid":false,"given":"Diana L.","family":"Nossa Gonz\u00e1lez","sequence":"first","affiliation":[{"name":"CEQUINOR (UNLP\u2010CONICET, CCT\u2010La Plata, associated with CIC) Departamento de Qu\u00edmica Facultad de Ciencias Exactas Universidad Nacional de La Plata  Boulevard 120 No 1465 1900 La Plata Rep\u00fablica Argentina"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6654-1315","authenticated-orcid":false,"given":"Jovanny A.","family":"G\u00f3mez Casta\u00f1o","sequence":"additional","affiliation":[{"name":"Grupo Qu\u00edmica\u2010F\u00edsica Molecular y Modelamiento Computacional (QUIMOL) Escuela de Ciencias Qu\u00edmicas Universidad Pedag\u00f3gica y Tecnol\u00f3gica de Colombia  Sede Tunja, Avenida Central del Norte Boyac\u00e1 050030 Colombia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7112-9296","authenticated-orcid":false,"given":"Aamer","family":"Saeed","sequence":"additional","affiliation":[{"name":"Department of Chemistry Quaid\u2010I\u2010Azam University  Islamabad 45320 Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7139-6685","authenticated-orcid":false,"given":"Gustavo A.","family":"Echeverria","sequence":"additional","affiliation":[{"name":"Departamento de F\u00edsica Facultad de Ciencias Exactas Universidad Nacional de La Plata e Instituto de F\u00edsica La Plata IFLP (UNLP, CONICET, CCT\u2010La Plata)  C. 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