Bis(4,4′-bipyridinium) bis(8-hydroxyquinoline-5-sulfonate) bipyridine pentahydrate

Reaction of 4,4′-bipyridine (4,4′-bipy) with barbituric (BAH), orotic (ORH), and uracil-5-carboxylic acids (U5CAH) yielded three new products, which have been characterized by single-crystal X-ray diffraction. The products include a co-crystal of neutral species with Z′ = 2 (4,4′-bipy/BAH), an organic complex ion pair (4,4′-bipy/ORH) and a compound containing both ionic and hydrogen-bonded neutral species (4,4′-bipy/U5CAH). Partial proton transfer is observed in both of the ionic cases, and in all three structures the crystal packing arrangement is such that weak hydrogen bonding, π···π and molecular dipole interactions are optimized.

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Crystal structure of the 1:1 co-crystal 4-(dimethylamino)pyridin-1-ium 8-hydroxyquinoline-5-sulfonate–N,N-dimethylpyridin-4-amine

Isobe,

Kashiwagi,

Kubono

2024

Acta Crystallogr E Cryst Commun

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The asymmetric unit of the title compound is composed of two independent ion pairs of 4-(dimethylamino)pyridin-1-ium 8-hydroxyquinoline-5-sulfonate (HDMAP+·HqSA−, C7H11N2 +·C9H6NO4S−) and neutral N,N-dimethylpyridin-4-amine molecules (DMAP, C7H10N2), co-crystallized as a 1:1:1 HDMAP+:HqSA−:DMAP adduct in the monoclinic system, space group Pc. The compound has a layered structure, including cation layers of HDMAP+ with DMAP and anion layers of HqSA− in the crystal. In the cation layer, there are intermolecular N—H...N hydrogen bonds between the protonated HDMAP+ molecule and the neutral DMAP molecule. In the anion layer, each HqSA− is surrounded by other six HqSA−, where the planar network structure is formed by intermolecular O—H...O and C—H...O hydrogen bonds. The cation and anion layers are linked by intermolecular C—H...O hydrogen bonds and C—H...π interactions.

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Bis(4,4′-bipyridinium) bis(8-hydroxyquinoline-5-sulfonate) bipyridine pentahydrate

Abstract: Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.003 A Ê R factor = 0.061 wR factor = 0.174 Data-to-parameter ratio = 17.6For details of how these key indicators were automatically derived from the article, see

Cited by 3 publications

References 6 publications

Spectroscopic and DFT investigations of 8-hydroxy quinoline-5-sulfonic acid-5-chloro-8-hydroxyquinoline cocrystal

Spectroscopic and DFT investigations of 8-hydroxy quinoline-5-sulfonic acid-5-chloro-8-hydroxyquinoline cocrystal

Classical and Weak Hydrogen Bonding Interactions between 4,4′-Bipyridine and Organic Acids: From Co-Crystal to Organic Complex

Crystal structure of the 1:1 co-crystal 4-(dimethylamino)pyridin-1-ium 8-hydroxyquinoline-5-sulfonate–N,N-dimethylpyridin-4-amine

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