Crystal structure and Hirshfeld surface analysis of 6-methyl-2,3-dihydro-1,3-benzothiazol-2-iminium 3-(1,3-benzothiazol-2-ylsulfanyl)propanoate
Year: 2026
Type: article
Abstract: In the title salt, C 8 H 9 N 2 S + ·C 10 H 8 NO 2 S 2 − , formed by proton transfer from the carboxylic acid to the ring N atom of 6-methyl-1,3-benzothiazol-2-amine, a 6-methyl-2,3-dihydro-1,3-benzothiazol-2-iminium cation ( A ) and a 3-(1,3-benzothiazol-2-ylsulfanyl)propanoate 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 benzothiazole 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 carboxylate O atoms of a single anion to form an R 2 2 (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.
Language: English
Subfield: Inorganic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $500
OpenAlex ID: W7223007953