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Open AccessArticle

Investigating Differences and Similarities between Betaxolol Polymorphs

1
Department of Industrial Engineering, University of Florence, via Santa Marta 3, 50139 Florence, Italy
2
Centro di Cristallografia Strutturale, University of Florence, via della Lastruccia 3, Sesto F.no, 50019 Florence, Italy
3
Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti OrganoMetallici (CNR-ICCOM), via Madonna del Piano 10, Sesto F.no, 50019 Florence, Italy
4
Department of Chemistry “U. Schiff”, University of Florence, via della Lastruccia 3, Sesto F.no, 50019 Florence, Italy
*
Author to whom correspondence should be addressed.
Crystals 2019, 9(10), 509; https://doi.org/10.3390/cryst9100509
Received: 29 August 2019 / Revised: 13 September 2019 / Accepted: 19 September 2019 / Published: 29 September 2019
Betaxolol belongs to the class of β1-adrenergic blocking agent. Several polymorphs of racemic betaxolol have been reported in the literature, but only one of them (BE_I) had the crystal structure determined from single-crystal X-ray diffraction. Here, we present a new crystalline phase of betaxolol (BE_IV). Its solid-state structure has been obtained from single-crystal X-ray diffraction data. The molecular and crystal arrangements of betaxolol in BE_IV have been further investigated by molecular modelling, by Cambridge Structural Database (CSD) surveys and by Hirshfeld surface analysis. A comparison with the solid-state structure of BE_I have been carried out. In the two polymorphs the 2-hydroxy-3-(isopropylamino)-propoxy chain, which is common to other β-blocker drugs, adopts a different conformation. In addition, the rotational isomer found in BE_IV is different with respect to the four already observed in the solid-state structure of analogous compounds. In both the polymorphs, the most significant interaction is due to the H-bonds involving the OH group as donor and the NH as acceptor, while the interaction where OH works as acceptor (NH acts as donor) is definitely less important. The resulting H-bond patterns are however different: Alternate R2,2(10) a > a (OH donors) and R2,2(10) b > b (OH acceptors) in BE_I vs. alternate R4,4 (8) a > b > a > b (OH donors) and R2,2 (10) b > b (OH acceptor) in BE_IV. View Full-Text
Keywords: betaxolol; polymorph; crystal structure; β1 blockers betaxolol; polymorph; crystal structure; β1 blockers
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MDPI and ACS Style

Rossi, P.; Paoli, P.; Milazzo, S.; Chelazzi, L.; Ienco, A.; Conti, L. Investigating Differences and Similarities between Betaxolol Polymorphs. Crystals 2019, 9, 509.

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