Iclaprim mesylate displaying a hydrogen-bonded mol-ecular tape

Acta Crystallogr E Crystallogr Commun. 2023 Jan 1;79(Pt 1):24-27. doi: 10.1107/S2056989022011689.

Abstract

The title compound, 2,6-di-amino-5-[(2-cyclo-propyl-7,8-dimeth-oxy-2H-1-benzo-pyran-5-yl)meth-yl]pyrimidin-1-ium methane-sulfonate, C19H23N4O3 +·CH3O3S-, is a salt made up from a protonated iclaprim mol-ecule and a mesylate anion. The pyrimidine and chromene units of the iclaprim mol-ecule form an orthogonal arrangement [inter-planar angle of 89.67 (6)°], and the 3-nitro-gen position of the pyrimidine ring is protonated. Four distinct N-H⋯O inter-actions and an additional N-H⋯N hydrogen bond connect iclaprim and mesylate mol-ecules to one another, resulting in an infinite hydrogen-bonded mol-ecular tape structure. The central section of the tape is formed by a sequence of fused hydrogen-bonded rings involving four distinct ring types.

Keywords: crystal structure; hydrogen bonding; pharmaceuticals.