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Acta Crystallogr E Crystallogr Commun. 2016 Apr 05;72:612-5. doi: 10.1107/S2056989016004916. eCollection 2016 May 01.

Crystal structure of levomepromazine maleate.

Acta crystallographica. Section E, Crystallographic communications

Gyula Tamás Gál, Nóra Veronika May, Petra Bombicz

Affiliations

  1. Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1519 Budapest, POB 206, Hungary.

PMID: 27308001 PMCID: PMC4908531 DOI: 10.1107/S2056989016004916

Abstract

The asymmetric unit of the title salt, C19H25N2OS(+)·C4H3O4 (-) [systematic name: (S)-3-(2-meth-oxy-pheno-thia-zin-10-yl)-N,N,2-tri-methyl-propanaminium hydrogen maleate], comprises two (S)-levomepromazine cations and two hydrogen maleate anions. The conformations of the two cations are similar. The major difference relates to the orientation of the meth-oxy substituent at the pheno-thia-zine ring system. The crystal components form a three-dimensional supra-molecular network via N-H⋯O, C-H⋯O and C-H⋯π inter-actions. A comparison of the conformations of the levomepromazine cations with those of the neutral mol-ecule and similar protonated mol-ecules reveals significant conformational flexibility of the pheno-thia-zine ring system and the substituent at the pheno-thia-zine N atom.

Keywords: C—H⋯π inter­actions; crystal structure; hydrogen bonding; maleate; pheno­thia­zine

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