Crystal structure of the tetra-ethyl-ammonium salt of the non-steroidal anti-inflammatory drug nimesulide (polymorph II)

Acta Crystallogr E Crystallogr Commun. 2024 Feb 20;80(Pt 3):314-317. doi: 10.1107/S2056989024001300. eCollection 2024 Mar 1.

Abstract

The crystal structure of the tetra-ethyl-ammonium salt of the non-steroidal anti-inflammatory drug nimesulide (polymorph II) (systematic name: tetra-ethyl-ammonium N-methane-sulfonyl-4-nitro-2-phen-oxy-anilinide), C8H20N+·C13H11N2O5S-, was determined using single-crystal X-ray diffraction. The title compound crystallizes in the monoclinic space group P21/c with one tetra-ethyl-ammonium cation and one nimesulide anion in the asymmetric unit. In the crystal, the ions are linked by C-H⋯N and C-H⋯O hydrogen bonds and C-H⋯π inter-actions. There are differences in the geometry of both the nimesulide anion and the tetra-ethyl-ammonium cation in polymorphs I [Rybczyńska & Sikorski (2023 ▸). Sci. Rep. 13, 17268] and II of the title compound.

Keywords: API; N-(4-nitro-2-phen­oxy­phen­yl)methane­sulfonamide; crystal structure; nimesulide; polymorphism; tetra­ethyl­ammonium salt.

Grants and funding

Funding for this research was provided by: Research of Young Scientists grant (BMN) No. 539-T080-B063-23 (University of Gdańsk), DS No. 531-T080-D738-23 (University of Gdańsk), and project ‘Innovation Incubator 4.0’ established by the announcement of the Minister of Science and Higher Education in Poland on 5 June 2020.