{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T01:58:51Z","timestamp":1767923931960,"version":"3.49.0"},"reference-count":47,"publisher":"International Union of Crystallography (IUCr)","issue":"2","license":[{"start":{"date-parts":[[2019,1,15]],"date-time":"2019-01-15T00:00:00Z","timestamp":1547510400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2019,1,15]],"date-time":"2019-01-15T00:00:00Z","timestamp":1547510400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2018,11,30]]},"published-print":{"date-parts":[[2019,2,1]]},"abstract":"<jats:p>Metoprolol {systematic name: (<jats:italic>RS<\/jats:italic>)-1-isopropylamino-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol}, C<jats:sub>15<\/jats:sub>H<jats:sub>25<\/jats:sub>NO<jats:sub>3<\/jats:sub>, is a cardioselective \u03b2<jats:sub>1<\/jats:sub>-adrenergic blocking agent that shares part of its molecular skeleton with a large number of other \u03b2-blockers. Results from its solid-state characterization by single-crystal and variable-temperature powder X-ray diffraction and differential scanning calorimetry are presented. Its molecular and crystal arrangements have been further investigated by molecular modelling, by a Cambridge Structural Database (CSD) survey and by Hirshfeld surface analysis. In the crystal, the side arm bearing the isopropyl group, which is common to other \u03b2-blockers, adopts an <jats:italic>all-trans<\/jats:italic> conformation, which is the most stable arrangement from modelling data. The crystal packing of metoprolol is dominated by an O\u2014H...N\/N...H\u2014O pair of hydrogen bonds (as also confirmed by a Hirshfeld surface analysis), which gives rise to chains containing alternating <jats:italic>R<\/jats:italic> and <jats:italic>S<\/jats:italic> metoprolol molecules extending along the <jats:italic>b<\/jats:italic> axis, supplemented by a weaker O...H\u2014N\/N\u2014H...O pair of interactions. In addition, within the same stack of molecules, a C\u2014H...O contact, partially oriented along the <jats:italic>b<\/jats:italic> and <jats:italic>c<\/jats:italic> axes, links homochiral molecules. Amongst the solid-state structures of molecules structurally related to metoprolol deposited in the CSD, the \u03b2-blocker drug betaxolol shows the closest analogy in terms of three-dimensional arrangement and interactions. Notwithstanding their close similarity, the crystal lattices of the two drugs respond differently on increasing temperature: metoprolol expands anisotropically, while for betaxolol, an isotropic thermal expansion is observed.<\/jats:p>","DOI":"10.1107\/s2053229618017084","type":"journal-article","created":{"date-parts":[[2019,1,15]],"date-time":"2019-01-15T11:00:23Z","timestamp":1547550023000},"page":"87-96","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":14,"title":["The solid-state structure of the \u03b2-blocker metoprolol: a combined experimental and <i>in silico<\/i> investigation"],"prefix":"10.1107","volume":"75","author":[{"given":"Patrizia","family":"Rossi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paola","family":"Paoli","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Laura","family":"Chelazzi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0402-1293","authenticated-orcid":true,"given":"Luca","family":"Conti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrea","family":"Bencini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,1,15]]},"reference":[{"key":"ky3155_bb1","unstructured":"Accelrys (2018). 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