Crystal structure of 4-benzylcarbamoyl-1-methylpyridin-1-ium iodide: an efficient multimodal antiviral drug

Abstract

In the title compound, [MeC 5 H 4 NCONHCH 2 C 6 H 5 ]I or C 14 H 15 N 2 O + ÁI À , a cation and an anion form an ionic pair linked by a strong N-HÁ Á ÁI hydrogen bond. In the crystal, ionic pairs linked by weak C-HÁ Á ÁI hydrogen bonds form infinite ribbons along the crystallographic a axis. Polymorphism screening varying crystallization solvents (water, acetone 90%-water, ethanol 90%-water, 2-propanol 90%-water, DMF, DMSO, methanol, acetonitrile) and conditions (solution temperature, heating and cooling protocols) did not reveal any other polymorphs than the one reported in this work.

4-[(Benzylamino)carbonyl]-1-methylpyridinium halogenide salts: X-ray diffraction study and Hirshfeld surface analysis

“…The AmCl salt crystallizes in the centrosymmetric P2 1 /n space group while the AmBr salt crystallizes in the Sohncke space group P2 1 2 1 2 1 , similar to the AmI salt (Drebushchak et al, 2017). The cation does not contain an asymmetric atom.…”

“…A search of the Cambridge Structural Database (Version 5.42, update of November 2020; Groom et al, 2016) revealed the structure of the AmI salt (refcode BEBFIA; Drebushchak et al, 2017). A comparison with the AmBr and AmI crystal structures showed that they are isostructural.…”

“…4-[(Benzylamino)carbonyl]-1-methylpyridinium iodide is known as a multimodal antiviral drug (Buhtiarova et al, 2003;Frolov et al, 2004;Boltz et al, 2018;Cocking et al, 2018). This salt crystallized in the P2 1 2 1 2 1 orthorhombic space group and was studied by single-crystal X-ray diffraction, powder diffraction, IR spectroscopy and DSC (Drebushchak et al, 2017). Screening varying different solvents and crystallization conditions did not reveal the formation of any other polymorphs.…”

Salts of 4-[(benzylamino)carbonyl]-1-methylpyridinium and iodide anions with different cation:iodine stoichiometric ratios

“…4-[(Benzylamino)carbonyl]-1-methylpyridinium iodide, chemical formula C 14 H 15 N 2 O + ÁI À , is used as a multimodal antiviral drug (te Velthuis et al, 2020;Boltz et al, 2018;Buhtiarova et al, 2003;Frolov et al, 2004). Its molecular and crystal structure have been studied in detail by diffraction and spectroscopic methods (Drebushchak et al, 2017). The formation of different polymorphic modifications of an API is of great importance for the pharmaceutical industry (Bernstein, 2002;Brittain, 2009;Hilfiker, 2006).…”

“…Unfortunately, all attempts to find polymorphic modifications of 4-[(benzylamino)carbonyl]-1-methylpyridinium iodide resulting from varying the solvents and crystallization conditions have failed. Only one crystal form with the P2 1 2 1 2 1 orthorhombic space group has been determined by single-crystal X-ray diffraction (Drebushchak et al, 2017).…”