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The vibrational shifts due to crystal packing interactions are evaluated from ab initio calculations for a set of suitable molecular pairs, using the B3LYP\/6\u201031G* approach.The proposed methodology provides an answer to the current demand for a reliable assignment of the vibrational spectra of these methyl\u2010xanthines, and clarifies several misleading assignments. The most relevant intermolecular interactions in each system and their effect on the vibrational spectra are considered and discussed. Based on these results, significant insights are obtained for the structure of caffeine in the anhydrous form (stable at room temperature), for which no X\u2010ray structure has been reported. A possible structure based on C<jats:sub>(8)<\/jats:sub>\uf8ffH\u22c5\u22c5\u22c5N<jats:sub>(9)<\/jats:sub> and C<jats:sub>(1,3)<\/jats:sub>\uf8ffH\u22c5\u22c5\u22c5O intermolecular interactions is suggested.<\/jats:p>","DOI":"10.1002\/cphc.200600308","type":"journal-article","created":{"date-parts":[[2006,9,19]],"date-time":"2006-09-19T03:27:25Z","timestamp":1158636445000},"page":"2150-2161","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":78,"title":["Computationally\u2010Assisted Approach to the Vibrational Spectra of Molecular Crystals: Study of Hydrogen\u2010Bonding and Pseudo\u2010Polymorphism"],"prefix":"10.1002","volume":"7","author":[{"given":"Mariela M.","family":"Nolasco","sequence":"first","affiliation":[]},{"given":"Ana M.","family":"Amado","sequence":"additional","affiliation":[]},{"given":"Paulo J. 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