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New pharmaceutical salts containing pyridoxine
Author(s) -
Cvetkovski Aleksandar,
Ferretti Valeria,
Bertolasi Valerio
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229617015765
Subject(s) - hydroxymethyl , hydrogen bond , chemistry , carboxylate , intermolecular force , pyridoxine hydrochloride , quinoxaline , stoichiometry , protonation , stereochemistry , medicinal chemistry , pyridoxine , organic chemistry , molecule , ion , biochemistry
Two mixed crystals were obtained by crystallizing the active pharmaceutical ingredient pyridoxine [systematic name: 4,5‐bis(hydroxymethyl)‐2‐methylpyridin‐3‐ol, PN] with ( E )‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enoic acid (ferulic acid) and 4‐hydroxy‐3,5‐dimethoxybenzoic acid (syringic acid). PN and the coformers crystallize in the form of pharmaceutical salts in a 1:1 stoichiometric ratio, namely 3‐hydroxy‐4,5‐bis(hydroxymethyl)‐2‐methylpyridin‐1‐ium ( E )‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enoate, C 8 H 12 NO 3 + ·C 9 H 9 O 5 − , and 3‐hydroxy‐4,5‐bis(hydroxymethyl)‐2‐methylpyridin‐1‐ium 4‐hydroxy‐3,5‐dimethoxybenzoate monohydrate, C 8 H 12 NO 3 + ·C 10 H 11 O 5 − ·H 2 O, the proton exchange between PN and the acidic partner being supported by the differences of the p K a values of the two components and by the C—O bond lengths of the carboxylate groups. Besides complex hydrogen‐bonding networks, π–π interactions between aromatic moieties have been found to be important for the packing architecture in both crystals. Hirshfeld surface analysis was used to explore the intermolecular interactions in detail and compare them with the interactions found in similar pyridoxine/carboxylic acid salts.