Crystal structure and Hirshfeld surface analysis of 6-methyl-2,3-di-hydro-1,3-benzo-thia-zol-2-iminium 3-(1,3-benzo-thia-zol-2-ylsulfan-yl)propanoate.

Abstract

In the title salt, C8H9N2S+·C10H8NO2S2-, formed by proton transfer from the carb-oxy-lic acid to the ring N atom of 6-methyl-1,3-benzo-thia-zol-2-amine, a 6-methyl-2,3-di-hydro-1,3-benzo-thia-zol-2-iminium cation (A) and a 3-(1,3-benzo-thia-zol-2-ylsulfan-yl)propano-ate anion (B) are present. Deprotonation of the carboxyl group is evidenced by its two distinctly different C-O bond lengths of 1.281 (6) and 1.220 (6) Å, while protonation of the ring N atom is confirmed by the localization of the corresponding H atom in a difference-Fourier map. Despite their different ionic states, the benzo-thia-zole fragments of the two components retain closely comparable bond lengths and angles. The cation and anion are linked by three charge-assisted N-H⋯O hydrogen bonds. Two of these, involving the ring N-H group and one of the amino N-H groups, bridge the two carboxyl-ate O atoms of a single anion to form an R22(8) graph-set motif; the third links these ion pairs into layers parallel to (100). Hirshfeld surface analysis, performed separately for components A and B, shows that H⋯H contacts dominate the surface for A (38.9%), followed by C⋯H/H⋯C (24.2%), O⋯H/H⋯O (13.0%) and S⋯H/H⋯S (11.9%) contacts. For anion B, the principal contributions are H⋯H (27.5%), S⋯H/H⋯S (25.7%), C⋯H/H⋯C (17.2%) and O⋯H/H⋯O (15.3%). The complementary H⋯O/O⋯H contributions are consistent with the important role of the charge-assisted N-H⋯O hydrogen bonds in consolidating the crystal packing.

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