(S,S,S,S)-Nebivolol hydrochloride hemihydrate

Yoann Rousselin,Amelie Bruel,Alexandre Clavel

doi:10.1107/s1600536812045813

Yoann Rousselin, Amelie Bruel + Show 1 more

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https://doi.org/10.1107/s1600536812045813

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Abstract

The asymmetric unit of the title hydrated salt, C22H26F2NO4 +·Cl−·0.5H2O, consists of an (S,S,S,S)-nebivolol {nebivol = bis[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]ammonium} cation, a chloride anion and a half-occupancy water molecule. The dihedral angle between the mean planes of the benzene rings is 50.34 (12)°. The pyran rings adopt half-chair conformations. The crystal packing features O—H⋯O hydrogen bonds and weak N—H⋯Cl, O—H⋯Cl, and O—H⋯Cl interactions, producing layers along (010).

Highlights

Universite de Bourgogne, ICMUB–UMR6302, 9 avenue Alain Savary, 21000 Dijon, France, and bCordenPharma–Synkem, 47 rue de Longvic, 21301, Chenove, France
H atoms treated by a mixture of independent and constrained refinement max = 0.43 e Å3
The combination of all the centers results in 16 theoretical stereoisomers and the total number of isomeric structures is reduced to 10 due to the symmetry plane through the N atom of the molecule. 9 of 10 isomeric structures are known and well described [Tuchalski et al (2006)], here we report the last unknown structure of the title compound, (I), C22H26F2NO4+Cl-.0.5H2O, the hydrochloride salt of (S,S,S,S)-nebivolol, obtained by total enantio selective synthesis

Summary

Nonius Kappa APEXII diffractometer

H atoms treated by a mixture of independent and constrained refinement max = 0.43 e Å3. Universite de Bourgogne, ICMUB–UMR6302, 9 avenue Alain Savary, 21000 Dijon, France, and bCordenPharma–Synkem, 47 rue de Longvic, 21301, Chenove, France. Key indicators: single-crystal X-ray study; T = 115 K; mean (C–C) = 0.006 Å; disorder in solvent or counterion; R factor = 0.072; wR factor = 0.137; data-toparameter ratio = 16.5. The asymmetric unit of the title hydrated salt, C22H26F2NO4+Cl0.5H2O, consists of an (S,S,S,S)-nebivolol {nebivol = bis[2(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]ammonium} cation, a chloride anion and a half-occupancy water molecule. The dihedral angle between the mean planes of the benzene rings is 50.34 (12). The crystal packing features O—H O hydrogen bonds and weak N—H Cl, O—H Cl, and O—. H Cl interactions, producing layers along (010)

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