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Open Access A rare positively charged nicotinic acid disulfide: 2,2′-dithiodinicotinic acid hydrochloride monohydrate

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The title compound {systematic name: 3-carboxy-2-[2-(3-carboxypyridin-2-yl)disulfan-1-yl)]pyridin-1-ium chloride monohydrate}, C12H9N2O4S2+·Cl−·H2O, crystallizes in the triclinic space group Poverline{1}. A pair of 2-mercaptonicotinic acid moieties is connected by a 2,2′-disulfide bond with a dihedral angle of 78.79 (3)°. One of the N atom is protonated, as are both carboxylate groups, resulting in an overall +1 charge on the dimer. The structure comprises a zigzagging layer of the dimerized dithiodinicotinic acid rings, with charge-balancing chloride ions and water molecules between the layers. Hydrogen bonding between the chloride and water sites with the dimer appears to hold the structure together. Nearest neighbor nicotinic acid rings are offset when viewed down the a axis, suggesting no added stability from ring stacking. The asymmetric unit corresponds to the empirical formula of the compound, and it packs with two formula units per unit cell.
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Document Type: Research Article

Affiliations: Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way Tallahassee, FL 32306, USA

Publication date: January 1, 2018

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