Crystal structure and anti-mycobacterial evaluation of 2-(cyclo-hexyl-meth-yl)-7-nitro-5-(tri-fluoro-meth-yl)benzo[ d]iso-thia-zol-3(2 H)-one

Adrian Richter; Richard Goddard; Peter Imming; Rüdiger W Seidel

doi:10.1107/S2056989023010137

Crystal structure and anti-mycobacterial evaluation of 2-(cyclo-hexyl-meth-yl)-7-nitro-5-(tri-fluoro-meth-yl)benzo[ d]iso-thia-zol-3(2 H)-one

Acta Crystallogr E Crystallogr Commun. 2023 Nov 30;79(Pt 12):1194-1198. doi: 10.1107/S2056989023010137. eCollection 2023 Dec 1.

Authors

Adrian Richter¹, Richard Goddard², Peter Imming¹, Rüdiger W Seidel¹

Affiliations

¹ Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), Germany.
² Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

Abstract

The title compound, C₁₅H₁₅F₃N₂O₃S, crystallizes in the monoclinic system, space group I2/a, with Z = 8. As expected, the nine-membered heterobicyclic system is virtually planar and the cyclo-hexyl group adopts a chair conformation. There is structural evidence for intra-molecular N-S⋯O chalcogen bonding between the benziso-thia-zolinone S atom and one O atom of the nitro group, approximately aligned along the extension of the covalent N-S bond [N-S⋯O = 162.7 (1)°]. In the crystal, the mol-ecules form centrosymmetric dimers through C-H⋯O weak hydrogen bonding between a C-H group of the electron-deficient benzene ring and the benzo-thia-zolinone carbonyl O atom with an R ² ₂(10) motif. In contrast to the previously described N-acyl 7-nitro-5-(tri-fluoro-meth-yl)benzo[d]iso-thia-zol-3(2H)-ones, the title N-cyclo-hexyl-methyl analogue does not inhibit growth of Mycobacterium aurum and Mycobacterium smegmatis in vitro.

Keywords: benzisothiazolinone; benzothiazinone; crystal structure; hydrogen bonding; mycobacteria.