Crystal structure of bis(1,4-diazabicyclo[2.2.2]octan-1-ium) thiosulfate dihydrate

Seck, Gorgui Awa; Sene, Aboubacary; Diop, Libasse; Maris, Thierry

doi:10.1107/s2056989016001535

Cited by 3 publications

(3 citation statements)

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“…By replacing the metal or ammonium cation with organic species we obtain compounds with new properties. Thiosulfates of protonated amines, which were often received by chance, have been the subject of merely a few publications (Leyten et al, 1988;Yang & Ng, 2011;Jiang et al, 1998;Srinivasan et al, 2011;Okuniewski et al, 2013;Seck et al, 2016). Aminium thiosulfates are the focus of our research due to their interesting supramolecular organization in the solid state.…”

Section: Introductionmentioning

confidence: 99%

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Brozdowska

Chojnacki

2017

Acta Crystallogr Sect B

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A series of diaminium thiosulfates, derivatives of diamines: NHCHCH(CH)NH (1) and NH(CH)NH, n = 3-6 [(2)-(5)] and thiosulfuric acid were prepared and their structures determined by single-crystal X-ray diffraction analysis. Compounds (1), (2) and (4) turned out to be hydrates. The crystal structure of 1,2-propylenediaminium thiosulfate is chiral and exhibits spontaneous resolution. Crystals for both enantiomers [(1a) and (1b)] were obtained with high enantiometric excess and examined. An extended network of strong, charge-assisted hydrogen bonding of the N-H...O type (also O-H...O and O-H...S for hydrates) is most likely the main factor defining crystal packing and the variable conformation of the cations. The formation of chiral hydrogen-bond motifs - distorted cubans - seems to induce the formation of chiral solid-state structure from achiral components in the case of (4). Diaminium thiosulfates with an odd number of C atoms in the alkyl chain [compounds (1), (2) and (4)] form three-dimensional supramolecular networks, while in the case of diaminium salts with an even number of C atoms [(3) and (5)], two-dimensional layers of hydrogen-bond domains are observed. The aminium thiosulfates were also characterized by elemental analysis, NMR and Fourier transform (FT)-IR spectroscopy. The conformations of α,ω-alkyldiaminium cations in the solid state are discussed and rationalized by DFT calculations.

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Section: Introductionmentioning

confidence: 99%

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Brozdowska

Chojnacki

2017

Acta Crystallogr Sect B

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“…[51] Since its introduction, the MetalJet X-ray source has been used in single crystal X-ray diffraction studies involving all kinds of different compounds. From small organic molecules [59][60][61][62][63][64] to proteins, [65][66][67][68] polymers [69,70] and metal organic frameworks. [71] Furthermore inorganic compounds containing p-block elements [72,73] as well as d-metal complexes [74][75][76][77][78][79][80] have been investigated.…”

Section: Metaljet X-ray Sourcementioning

confidence: 99%

“…A set of objects prepared in this way and a laboratory stand at hand, in principle all types of screw axes can be modelled, if the correct number of ducks is arranged in a suitable manner. With certain screw axes (42,62,63,64) two or more objects occupy positions at the same height. To be able to accurately model this, special mounts were designed, which have several pieces of sheet metal attached to the same aluminium block (see Figure 2 -18).…”

Section: Screw Axesmentioning

confidence: 99%

Bis(benzoxazol-2-yl)methanides in main group organometallic syntheses and enquiry-based education

Graw¹

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A contribution to the crystal chemistry and topology of organic thiosulfates: bis(1-methylpiperazinium)·S₂O₃·H₂O versus 1-methylpiperazinediium·S₂O₃·3H₂O

Charkin,

Banaru,

Ivanov

et al. 2024

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Single crystals of two new compounds, (C5H14N2)S2O3·H2O (1) and (C5H13N2)2S2O3·3H2O (2), were isolated from the reaction products of 1-methylpiperazine, sulfuric acid, and barium thiosulfate in aqueous media. The crystal structures have been determined by single-crystal X-ray diffraction. In agreement to the previous observations, the organic template may contribute to the formation of thiosulfates both as mono- and diprotonated species, but this is the first case where both products are reported for the same organic compound. In both structures 1 and 2, complex nets of hydrogen bonds involve all cations, anions and water molecules. Comparisons are made to the structures of other thiosulfates containing mono- or diprotonated diamine species.

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Crystal structure of bis(1,4-diazabicyclo[2.2.2]octan-1-ium) thiosulfate dihydrate

Abstract: The crystal structure of the title salt hydrate contains discrete DABCOH+ cations (DABCO = 1,4-diazabicyclo[2.2.2]octane), thiosulfate anions and lattice water molecules. The three molecular components are held together through hydrogen bonds.

Cited by 3 publications

References 15 publications

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Bis(benzoxazol-2-yl)methanides in main group organometallic syntheses and enquiry-based education

A contribution to the crystal chemistry and topology of organic thiosulfates: bis(1-methylpiperazinium)·S₂O₃·H₂O versus 1-methylpiperazinediium·S₂O₃·3H₂O

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Crystal structure of bis(1,4-diazabicyclo[2.2.2]octan-1-ium) thiosulfate dihydrate

Abstract: The crystal structure of the title salt hydrate contains discrete DABCOH+ cations (DABCO = 1,4-di­aza­bicyclo­[2.2.2]octa­ne), thio­sulfate anions and lattice water mol­ecules. The three mol­ecular components are held together through hydrogen bonds.

Cited by 3 publications

References 15 publications

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates

Bis(benzoxazol-2-yl)methanides in main group organometallic syntheses and enquiry-based education

A contribution to the crystal chemistry and topology of organic thiosulfates: bis(1-methylpiperazinium)·S2O3·H2O versus 1-methylpiperazinediium·S2O3·3H2O

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Abstract: The crystal structure of the title salt hydrate contains discrete DABCOH+ cations (DABCO = 1,4-diazabicyclo[2.2.2]octane), thiosulfate anions and lattice water molecules. The three molecular components are held together through hydrogen bonds.

A contribution to the crystal chemistry and topology of organic thiosulfates: bis(1-methylpiperazinium)·S₂O₃·H₂O versus 1-methylpiperazinediium·S₂O₃·3H₂O