Hydrogen bonding in two salts of 3‐methylthio‐4‐(propargylthio)quinoline

In 3‐methyl­thio‐4‐(propargyl­thio)­quinolinium chloride monohydrate, C₁₃H₁₂NS₂⁺·Cl^?·H₂O, and 3‐methyl­thio‐4‐(propargyl­thio)­quinolinium tri­chloro­acetate, C₁₃H₁₂­NS₂⁺·­C₂Cl₃O₂^?, the terminal alkyne group forms C[triple‐bond]C—H?O hydrogen bonds of favourable geometry. The conformation of the flexible propargyl­thio group is different in the two structures.     

Hydrogen bonding and π–π stacking in methyl­aminium 4′,7‐dihydroxy­isoflavone‐3′‐sulfonate dihydrate and hexa­aqua­iron(II) bis­(4′,7‐diethoxy­isoflavone‐3′‐sulfonate) tetra­hydrate

In methyl­aminium 4′,7‐dihydroxy­isoflavone‐3′‐sulfonate dihydrate, CH₆N⁺·C₁₅H₉O₇S⁻·2H₂O, 11 hydrogen bonds exist between the methyl­aminium cations, the iso­flavone‐3′‐sulfonate anions and the solvent water mol­ecules. In hexa­aqua­iron(II) bis­(4′,7‐diethoxy­isoflavone‐3′‐sulfonate) tetra­hydrate, [Fe(H₂O)₆](C₁₉H₁₇O₇S)₂·4H₂O, 12 hydrogen bonds exist between the centrosymmetric [Fe(H₂O)₆]²⁺ cation, the isoflavone‐3′‐sulfonate anions and the solvent water mol­ecules. Additional π–π stacking inter­actions generate three‐dimensional supramolecular structures in both compounds.     

1‐Methyl­piperazine‐1,4‐diium 4‐nitro­phthalate(2–) 4‐nitro­phthalic acid monohydrate

The title adduct, C₅H₁₄N₂²⁺·C₈H₃NO₆²⁻·C₈H₅NO₆·H₂O, crystallizes in the monoclinic space group P2₁. All O atoms of the 4‐nitro­phthalate anions and neutral 4‐nitro­phthalic acid mol­ecules are involved in hydrogen bonding with the piperazine dication and the water mol­ecule of crystallization.     

(μ‐2,6‐Bis{[(2‐hydroxy­phenyl)­(2‐pyri­dyl­methyl)­amino]­methyl}‐4‐methyl­phenolato)­bis­[di­aqua­nickel(II)] ace­tate dimethyl­formamide 0.75‐hy­drate

The binuclear cation of the title compound, [Ni₂(C₃₃H₂₉­N₄O₃)(H₂O)₄]C₂H₃O₂·C₃H₇NO·0.75H₂O, was synthesized as a model for the active site of urease. Two tridentate halves of the symmetrical 2,6‐bis{[(2‐hydroxy­phenyl)(2‐pyridyl­methyl)­amino]­methyl}‐4‐methyl­phenolate (BPPMP^3?) ligand are arranged in a meridional fashion around the two Ni^II ions, with the phenoxo O atom bridging the Ni^II ions. The cation has an approximate twofold rotation axis running through the C—O bond of the bridging phenolate group. Four water mol­ecules complete the octahedral environment of each Ni^II ion.     

A uranyl ion complex of N‐methyl‐p‐tert‐butyl­dihomo­ammonio­calix­[4]­arene with di­aqua­di­pyridine­lithium as counter‐ion

The title complex, di­aqua­di­pyridine­lithium (N‐methyl‐p‐tert‐butyl­dihomo­ammonio­calix­[4]­arene‐κ⁴O)­dioxouranium(VI) tri­pyridine solvate monohydrate, [Li(C₅H₅N)₂(H₂O)₂][UO₂(C₄₆H₅₈NO₄)]·3C₅H₅N·H₂O, contains an `internal' tetraphenoxide‐coordinated uranyl complex of the macrocycle, in which the protonated N atom is involved in an intramolecular hydrogen bond with the uranyl oxo group located in the cavity. The Li⁺ ion is in a tetrahedral environment and its two water ligands are involved in hydrogen bonds with two phenoxide O atoms, two pyridine mol­ecules and one water mol­ecule. This arrangement is compared with those obtained previously for other homo­aza­calixarenes and also for homo­oxa­calixarenes in the presence of alkali metal hydro­xides.     

Two salts of di‐p‐toluoyltartaric acid with aromatic amines

The structures of bis­[(R)‐(+)‐1‐phenyl­ethyl­ammonium] (2R,3R)‐(−)‐2,3‐di‐p‐toluoyloxybutane­dioate methanol disolvate monohydrate, 2C₈H₁₂N⁺·C₂₀H₁₆O₈²⁻·2CH₄O·H₂O, (I), and bis­(benzyl­ammonium) (2R,3R)‐(−)‐2,3‐di‐p‐toluoyl­oxy­butane­­dioate dihydrate, 2C₇H₁₀N⁺·C₂₀H₁₆O₈²⁻·2H₂O, (II), exhibit extensive hydrogen bonding, with (N—)H⋯O and (O—)H⋯O distances in the ranges 2.716 (2)–2.929 (3) and 2.687 (2)–2.767 (2) Å, respectively, in (I), and 2.673 (2)–2.888 (2) and 2.785 (2)–2.931 (2) Å, respectively, in (II). The amine groups are protonated and the carboxyl­ate groups of the tartrate anions are fully deprotonated. The conformation of the toluoyltartrate anion and its mol­ecular parameters are similar in both structures.     

Hydro­gen bonding in proton‐transfer compounds of 5‐sulfosalicylic acid with bicyclic heteroaromatic Lewis bases

The crystal structures of quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate trihydrate, C₉H₈N⁺·C₇H₅O₆S⁻·3H₂O, (I), 8‐hydroxy­quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate monohydrate, C₉H₈NO⁺·C₇H₅O₆S⁻·H₂O, (II), 8‐amino­quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate dihydrate, C₉H₉N₂⁺·C₇H₅O₆S⁻·2H₂O, (III), and 2‐carboxy­quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate quinolinium‐2‐carboxylate, C₁₀H₈NO₂⁺·C₇H₅O₆S⁻·C₁₀H₇NO₂, (IV), four proton‐transfer compounds of 5‐sulfosalicylic acid with bicyclic heteroaromatic Lewis bases, reveal in each the presence of variously hydrogen‐bonded polymers. In only one of these compounds, viz. (II), is the protonated quinolinium group involved in a direct primary N⁺—H⋯O(sulfonate) hydrogen‐bonding interaction, while in the other hydrates, viz. (I) and (III), the water mol­ecules participate in the primary intermediate interaction. The quinaldic acid (quinoline‐2‐carboxylic acid) adduct, (IV), exhibits cation–cation and anion–adduct hydrogen bonding but no direct formal heteromolecular interaction other than a number of weak cation–anion and cation–adduct π–π stacking associations. In all other compounds, secondary interactions give rise to network polymer structures.     

Oxonium 5‐amino­uracil‐6‐sulfonate hydrate

In the title compound, oxonium 5‐amino‐2,6‐dioxo‐1,2,3,6‐tetra­hydro­pyrimidine‐4‐sulfonate hydrate, H₃O⁺·­C₄H₄­N₃­O₅S^?·­H₂O, the sulfonate group is in the anionic form and charge balance is provided by an o­xonium cation, H₃O⁺. Screw‐related mol­ecules overlap significantly and are hydrogen bonded to form a zigzag chain of the uracil skeleton along the direction of the c screw axis. The partially stacked bases and their glide‐related equivalents run parallel to the a axis to form hydro­phobic zones separated by hydro­philic zones built up by a network of hydrogen bonds.     

Isomorphous brucinium 4‐nitro­benzoate methanol solvate and brucinium 4‐nitro­benzoate dihydrate

In isomorphous crystals of brucinium 4‐nitro­benzoate methanol solvate, C₂₃H₂₇N₂O₄⁺·C₇H₄NO₄⁻·CH₃OH, and brucinium 4‐nitro­benzoate dihydrate, C₂₃H₂₇N₂O₄⁺·C₇H₄NO₄⁻·2H₂O, the brucinium cations form reverse corrugated layers, in which the amine N and amide O atoms of the brucinium cations are located in the grooves and at convex points of the layer surface, respectively. Similarly, as observed for the commonly occurring corrugated brucinium layers, the amide O atoms of the cations are involved in hydrogen bonds in which solvent mol­ecules are the donors.     

Cobalt(II) and nickel(II) complexes of quinoline‐2‐carboxyl­ate

The title complexes, trans‐di­aqua­bis­(quinoline‐2‐carboxyl­ato‐κ²N,O)­cobalt(II)–water–methanol (1/2/2), [Co(C₁₀H₆NO₂)₂(H₂O)₂]·2CH₄O·2H₂O, and trans‐di­aqua­bis­(quinoline‐2‐car­box­yl­ato‐κ²N,O)­nickel(II)–water–methanol (1/2/2), [Ni(C₁₀H₆NO₂)₂(H₂O)₂]·2CH₄O·2H₂O, are isomorphous and contain Co^II and Ni^II ions at centers of inversion. Both complexes have the same distorted octahedral coordination geometry, and each metal ion is coordinated by two quinoline N atoms, two carboxyl­ate O atoms and two water O atoms. The quinoline‐2‐carboxyl­ate ligands lie in trans positions with respect to one another, forming the equatorial plane, with the two water ligands occupying the axial positions. The complex mol­ecules are linked together by hydrogen bonding involving a series of ring patterns which include the uncoordinated water and methanol mol­ecules.     

Aquachlorobis[4,4,5,5‐tetramethyl‐2‐(2‐pyridyl)‐4,5‐dihydro‐1H‐imidazol‐1‐oxyl 3‐oxide‐κ2O1,N2]nickel(II) nitrate methanol disolvate monohydrate

The title complex, [NiCl(C₁₂H₁₆N₃O₂)₂(H₂O)]NO₃·2CH₄O·H₂O, was obtained from a methano­lic solution of Ni(NO₃)₂·6H₂O, 2‐pyridyl nitro­nyl nitro­xide (2‐NITpy) and (NEt₄)₂[CoCl₄]. The equatorial coordination sites of the octahedral Ni^II centre are occupied by two chelating radical ligands, with the axial positions occupied by the Cl^? and water ligands. The H₂O—Ni—Cl axis of the complex lies along a crystallographic twofold axis, so that only half the cation is present in the asymmetric unit. The Ni—Cl bond length [2.3614 (17) Å] is significantly shorter than distances typical of octahedral Ni^II centres [2.441 (5) Å]. However, with only one nitrate anion per formula unit, the oxidation state of the metal must be assigned as Ni^II. The 2‐NITpy ligands bend away from the equatorial plane, forming a hydro­phobic region around the Cl atoms. Conversely, the ligated water mol­ecule forms moderately strong hydrogen bonds with the disordered methanol solvent mol­ecules, which in turn form interactions with the water of crystallization and the disordered nitrate anion. These interactions combine to give hydro­philic regions throughout the crystal structure.     

Thia­mine tetra­phenyl­borate monohydrate: a two‐dimensional hydrogen‐bonded network with (4,4)‐topology

The title compound, 3‐[(4‐amino‐2‐methyl­pyrimidin‐5‐yl)­meth­yl]‐5‐(2‐hydroxy­eth­yl)‐4‐methyl­thia­zolium tetra­phenyl­borate monohydrate, C₁₂H₁₇N₄OS⁺·C₂₄H₂₀B⁻·H₂O, is a salt in which the thiamine cations are linked by hydrogen bonds into a two‐dimensional network having (4,4)‐topology. The stacked sheets form channels, which are occupied by the anions; the cations and anions are linked by C—H⋯π(arene) hydrogen bonds.     

The hydrogen‐bonded adduct 7,16‐diazonia‐18‐crown‐6–4‐aminobenzenesulfonate–water (1/2/2)

In the title hydrated adduct, 1,4,10,13‐tetraoxa‐7,16‐diazo­nia­cyclo­octa­decane bis(4‐amino­benzene­sulfonate) dihydrate, C₁₂H₂₈N₂O₄²⁺·2C₆H₆NO₃S⁻·2H₂O, formed between 7,16‐di­aza‐18‐crown‐6 and the dihydrate of 4‐amino­benzene­sulfonic acid, the macrocyclic cations lie across centres of inversion in the orthorhombic space group Pbca. The anions alone form zigzag chains, and the cations and anions together form sheets that are linked via water mol­ecules and anions to form a three‐dimensional grid.     

Sodium 2‐oxo‐3‐semicarbazono‐2,3‐dihydro‐1H‐indole‐5‐sulfonate dihydrate

The title compound, Na⁺·C₉H₇N₄O₅S⁻·2H₂O, presents a Z configuration around the imine C=N bond and an E configuration around the C(O)NH₂ group, stabilized by two intra­molecular hydrogen bonds. The packing is governed by ionic inter­actions between the Na⁺ cation and the surrounding O atoms. The ionic unit, Na⁺ and 2‐oxo‐3‐semicarbazono‐2,3‐dihydro‐1H‐indole‐5‐sulfonate, forms layers extending in the bc plane. The layers are connected by hydrogen bonds involving the water mol­ecules.     

Solid‐state architecture of saccharin salts of some diamines

Hydrazinium saccharinate, N₂H₅⁺·C₇H₄NO₃S⁻, crystallizes in a 1:1 ratio, while ethyl­ene­diaminium bis­(saccharinate), C₂H₁₀N₂²⁺·2C₇H₄NO₃S⁻, and butane‐1,4‐diaminium bis­(sac­charin­ate), C₄H₁₄N₂²⁺·2C₇H₄NO₃S⁻, form in a 1:2 cation–anion stoichiometry. The structures contain many strong hydrogen bonds of the N⁺—H⋯N⁻, N⁺—H⋯O, N—H⋯O and N—H⋯N types, with auxiliary C—H⋯O inter­actions.     

2‐(Hydro­xy­methyl)­pyridinium di­hydrogenphosphate

The title compound, C₆H₈NO⁺·H₂PO₄⁻, consists of 2‐(hy­droxy­methyl)­pyridinium and di­hydrogen­phosphate ions. The di­hydrogen­phosphate moieties are linked into chains by pairs of P—O—H⃛O—P hydrogen bonds. The 2‐(hydroxy­methyl)­pyridinium cations are connected to the di­hydrogen­phosphate units by O—H⃛O and N—H⃛O hydrogen bonds. Weak π–π interactions help to determine the interchain packing.     

4‐(4‐Hydro­xy­benzyl­idene­amino)‐4H‐1,2,4‐triazole hemihydrate

In the title compound, 4‐(4H‐1,2,4‐triazol‐4‐yl­imino­methyl)­phenol hemi­hydrate, C₉H₈N₄O·0.5H₂O or (I)·0.5H₂O, mol­ecules of (I) are arranged as layers running along the b axis through intermolecular O—H?N and C—H?O hydrogen bonds. These layers are stabilized by hydrogen‐bonded water mol­ecules to form three‐dimensional networks.     

Two N,N‐dimethylbiguanidium salts displaying double hydrogen bonds to the counter‐ions

The crystal structures of N,N‐di­methyl­biguanidium oxalate monohydrate, C₄H₁₃N₅²⁺·C₂O₄²⁻·H₂O, (I), and N,N‐di­methyl­biguanidium sulfate monohydrate, C₄H₁₃N₅²⁺·SO₄²⁻·H₂O, (II), show that both compounds contain the same N,N‐di­methyl­biguanidium dication. In (I), two independent oxalate ions lie about inversion centres. Strong double hydrogen bonds, with D⋯A distances of 2.658 (2) and 2.830 (3) Å in (I), and 2.722 (3) and 2.815 (3) Å in (II), are present between N atoms of the N,N‐di­methyl­biguanidium moieties and either the carboxyl­ate group of the oxalate anion or the sulfate anion.     

Hydrogen phosphate and dihydrogen phosphate salts of 4‐amino­azobenzene

4‐Amino‐trans‐azobenzene {or 4‐[(E)‐phenyl­diazen­yl]aniline} can form isomeric salts depending on the site of protonation. Both orange bis{4‐[(E)‐phenyl­diazen­yl]anilinium} hydrogen phos­phate, 2C₁₂H₁₂N₃⁺·HPO₄²⁻, and purple 4‐[(E)‐phenyl­diazen­yl]­anilinium dihydrogen phosphate phosphoric acid solvate, C₁₂H₁₂N₃⁺·H₂PO₄⁻·H₃PO₄, (II), have layered structures formed through O—H⋯O and N—H⋯O hydrogen bonds. Additionally, azobenzene fragments in (I) are assembled through C—H⋯π inter­actions and in (II) through π–π inter­actions. Arguments for the colour difference are tentatively proposed.     

Layered structures in proton‐transfer compounds of 5‐sulfosalicylic acid with the aromatic polyamines 2,6‐diamino­pyridine and 1,4‐phenyl­ene­diamine

The crystal structures of two proton‐transfer compounds of 3‐carb­oxy‐4‐hydroxy­benzene­sulfonic acid (5‐sulfosalicylic acid) with the aromatic polyamines 2,6‐diamino­pyridine [namely 2,6‐diamino­pyridinium 3‐carb­oxy‐4‐hydroxy­benzene­sulfonate monohydrate, C₅H₈N₃⁺·C₇H₅O₆S⁻·H₂O, (I)] and 1,4‐phenyl­ene­diamine [namely 1,4‐phenyl­ene­diaminium 3‐carboxyl­ato‐4‐hydroxy­benzene­sulfonate, C₆H₁₀N₂²⁺·C₇H₄O₆S²⁻, (II)] have been determined. Both compounds feature extensively hydrogen‐bonded three‐dimensional layered polymer structures having significant inter­layer π–π inter­actions between the cation and anion species. In (I), the pyridine N atom of the Lewis base is protonated and forms a direct hydrogen‐bonding inter­action with the water mol­ecule, which together with the two amine groups of the cation and the carboxylic acid group of the anion also give additional inter­actions with O‐atom acceptors of the sulfonate group. In (II), a dianionic species results from deprotonation of both the sulfonic and the carboxylic acid groups, and all available O‐atom acceptors inter­act with all dication donors, which lie about inversion centres.