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.     

The sodium salt of 2‐hydroxy‐5‐nitrobenzylsulfonic acid

The structural data for sodium 2‐hydroxy‐5‐nitro­benzyl­sulfonate monohydrate, Na⁺·C₇H₆NO₆S^?·H₂O, which mimics an artificial substrate for human aryl­sulfatase A, viz. p‐­nitrocatechol sulfate, reveal that the geometric parameters of the substrate and its analogue are very similar. Two water mol­ecules, the phenolic O atom and three sulfonate O atoms form the coordination sphere of the Na⁺ ion, which is a distorted octahedron. The Na⁺ cations and the O atoms join to form a chain polymer.     

(8‐Dimethylamino‐1‐naphthyl)dimethylammonium 3‐carboxy‐1,4,5,‐6,7,7‐hexachlorobicyclo[2.2.1]hept‐5‐ene‐2‐carboxylate hydrate

The structure of the title compound, C₁₄H₁₉N₂⁺·C₉H₃Cl₆O₄^?·H₂O, consists of singly ionized 1,4,5,6,7,7‐hexachlorobicyclo[2.2.1]hept‐5‐ene‐2,3‐dicarboxylic acid anions and protonated 1,8‐bis(dimethylamino)naphthalene cations. In the (8‐dimethylamino‐1‐napthyl)dimethylammonium cat­ion, a strong disordered intramolecular hydrogen bond is formed with N?N = 2.589 (3) Å. The geometry and occupancy obtained in the final restrained refinement suggest that the disordered hydrogen bond may be asymmetric. Water mol­ecules link the anion dimers into infinite chains via hydrogen bonding.     

2(S)‐Amino‐3‐[1H‐imidazol‐4(5)‐yl]­propyl cyclo­hexylmethyl ether di­hydro­chloride and 2(S)‐amino‐3‐[1H‐imidazol‐4(5)‐yl]­propyl 4‐bromo­benzyl ether di­hydro­chloride

(Cyclo­hexyl­methyl­oxy­methyl)(1H‐imidazol‐4‐io­methyl)‐(S)‐ammonium dichloride, C₁₃H₂₅N₃O⁺·2Cl^?, and (4‐bromo­benzyl)(1H‐imidazol‐4‐io­methyl)‐(S)‐ammonium dichloride, C₁₃H₁₈BrN₃O⁺·2Cl^?, are model compounds with different biological activities for evaluation of the hist­amine H3‐receptor activation mechanism. Both title compounds occur in almost similar extended conformations.     

(Z)‐2‐Methylbuten‐1‐yl(aryl)iodonium trifluoromethanesulfonates containing electron‐withdrawing groups on the aryl moiety

The crystal structures of [(Z)‐2‐methyl­but‐1‐en‐1‐yl]­[4‐(tri­fluoro­methyl)­phenyl]­iodo­nium tri­fluoro­methane­sulfonate, C₁₂H₁₃F₃I⁺·CF₃O₃S^?, (I), (3,5‐di­chloro­phenyl)­[(Z)‐2‐methyl­but‐1‐en‐1‐yl]­iodo­nium tri­fluoro­methane­sulfonate, C₁₁H₁₂­Cl₂I⁺·CF₃O₃S^?, (II), and bis{[3,5‐bis­(tri­fluoro­methyl)­phenyl][(Z)‐2‐methyl­but‐1‐en‐1‐yl]­iodo­nium} bis­(tri­fluoro­methane­sulfonate) di­chloro­methane solvate, 2C₁₃H₁₂F₆I⁺·­2CF₃­O₃S^?·CH₂Cl₂, (III), are described. Neither simple acyclic β,β‐di­alkyl‐substituted alkenyl­(aryl)­idonium salts nor a series containing electron‐deficient aryl rings have been described prior to this work. Compounds (I)–(III) were found to have distorted square‐planar geometries, with each I atom interacting with two tri­fluoro­methane­sulfonate counter‐ions.     

Intramolecular cyclization of 4,7‐bis(2‐bromo­acetyl)‐1‐thia‐4,7‐di­azacyclo­nonane

The reaction of 1‐thia‐4,7‐di­azacyclo­nonane with bromo­acetyl bromide in CHCl₃ affords the unexpected salt 4‐(2‐bromo­acetyl)‐8‐oxo‐1‐thionia‐4,7‐di­aza­bi­cyclo­[5.2.2]­un­decane bromide, C₁₀H₁₆BrN₂O₂S⁺·Br⁻. Two units of the salt are linked by S⋯Br contacts about a crystallographic inversion centre, thus forming dimers that are linked by Br⋯Br contacts into extended ribbons. S⋯O contacts between these ribbons generate a two‐dimensional sheet.     

Ammonium 1‐hydroxy‐2‐(2‐pyridinio)ethane‐1,1‐diyldiphosphonate dihydrate and potassium 1‐hydroxy‐2‐(2‐pyridinio)ethane‐1,1‐diyldiphosphonate dihydrate

The crystal structures of the title compounds, ammonium risedronate dihydrate, NH₄⁺·C₇H₁₀NO₇P₂⁻·2H₂O, (I), and potassium risedronate dihydrate, K⁺·C₇H₁₀NO₇P₂⁻·2H₂O, (II), have been determined from single‐crystal X‐ray data collected at 120 K. Compound (I) forms a three‐dimensional hydrogen‐bonded network which connects the ammonium and risedronate ions and the water mol­ecules. In compound (II), the K⁺ ions are seven‐coordinated in a capped distorted trigonal prism. The coordination polyhedra form chains by corner‐sharing, and these chains are connected by phosphon­ate groups into layers in the ac plane. The layers are stacked and connected by hydrogen bonds in the b direction. The risedronate conformation is determined by intra­molecular inter­actions fine‐tuned by crystal packing effects. All H‐atom donors in both structures are involved in hydrogen bonding, with D⋯A distances between 2.510 (2) and 3.009 (2) Å.     

3β‐(1‐Allyl‐1‐pyrrolidinio)‐16‐(2‐pyridylmethylene)androst‐5‐en‐17β‐ol bromide hemihydrate

The title compound, C₃₂H₄₅N₂O⁺·Br^?·0.5H₂O, has the outer two six‐membered rings in chair conformations, while the central ring is in an 8β,9α‐half‐chair conformation. The five‐mem­bered ring of the steroid nucleus adopts a slightly deformed 14α‐envelope conformation. The pyridyl­methyl­ene moiety has an E configuration with respect to the hydroxyl group at position 17. The structure is stabilized by a network of O—H?Br‐type intermolecular hydrogen bonds.     

2‐[6‐(1H‐Benzimidazol‐2‐yl)‐2‐pyridyl]‐1H‐benzimidazol‐3‐ium perchlorate monohydrate

The title compound, C₁₉H₁₄N₅⁺·ClO₄^?·H₂O, contains planar C₁₉H₁₄N₅⁺ cations, perchlorate anions and water mol­ecules. The two closest parallel cations (plane‐to‐plane distance of 3.41 Å), together with two neighbouring perchlorate anions and two water mol­ecules, form an electrically neutral quasi‐dimeric unit. Two acidic H atoms of the cation, both H atoms of the water mol­ecule, the N atoms of the imidazole rings and three of the four O atoms of the perchlorate anion are involved in the hydrogen‐bonding network within the dimeric unit. The remaining third acidic H atom of the imidazole rings and the water mol­ecules complete a two‐dimensional network of hydrogen bonds, thus forming puckered layers of dimers. The angle between the planes of two neighbouring dimeric units in the same layer is 33.25 (3)°.     

(M)‐ and (P)‐8‐[(1S,2R)‐2‐hydroxy‐1‐methyl‐2‐phenylethyl]‐8‐methyl‐8,9‐dihydro‐7H‐dinaphth[2,1‐c:1′,2′‐e]azepinium bromide solvates

The title compounds are diastereoisomers with antipodean axial chirality. The M isomer crystallizes as a (1/3) acetone solvate, C₃₂H₃₀NO⁺·Br^?·3C₃H₆O, while the P isomer crystallizes as a (1/1) di­chloro­methane solvate, C₃₂H₃₀NO⁺·Br^?·CH₂Cl₂. In each structure, O—H?Br hydrogen bonds link the cations and anions to give ion pairs. The seven‐membered azepinium ring adopts the usual twisted‐boat conformation and its ring strain causes a slight curvature of the plane of each naphthyl ring.     

Poly[tetrasodium(I)‐tetra‐μ2‐bis(butane‐1,4‐diyldioxy)borato‐μ2‐1,4‐butane­diol]

In the title compound, [Na₄(C₈H₁₆BO₄)₄(C₄H₁₀O₂)]_n, there are two coordination types for the four independent Na⁺ cations: two Na⁺ cations bond to six diolate O atoms [Na—O = 2.305 (2)–2.609 (2) Å], while the other two are five‐coordinate via one 1,4‐butane­diol [2.289 (2) and 2.349 (3) Å] and four diolate O atoms [2.295 (2)–2.408 (2) Å]. Corresponding to this, there are three‐ and four‐coordinate diolate O atoms, the latter bridging Na atoms. The 1,4‐butane­diol mol­ecules lie on inversion centres. The boron stereochemistry shows minor local perturbations from its usual tetrahedral state [B—O = 1.457 (4)–1.503 (4) Å]. The resulting polymer packs as sheets parallel to the (10) plane crosslinked by the butane­diol mol­ecules. The structure was solved using data from a multiple crystal.     

Mono­alkyl­ated 4′‐aryl‐substituted terpyridines

1‐Methyl‐2‐[4‐phenyl‐6‐(pyridinium‐2‐yl)­pyridin‐2‐yl]­pyridinium diperchlorate, C₂₂H₁₉N₃²⁺·2ClO₄⁻, (I), and 2‐[4‐(methoxy­phenyl)‐2,2′‐bipyridin‐6‐yl]‐1‐methyl­pyridinium iodide, C₂₃H₂₀N₃O⁺·I⁻, (II), both crystallize in the monoclinic space group P2₁/c. In contrast with the monocharged mol­ecule of (II), the doubly charged mol­ecule of (I) contains an additional protonated pyridine ring. One of the two perchlorate counter‐anions of (I) interacts with the cation of (I) via an N—H⋯O hydrogen bond. In (II), two mol­ecules related by a centre of symmetry are connected by weak π–π interactions, forming dimers in the crystal structure.     

Hydrogen bonding in 1:1 proton‐transfer compounds of 5‐sulfosalicylic acid with 4‐X‐substituted anilines (X = F,Cl or Br)

The crystal structures of three proton‐transfer compounds of 5‐sulfosalicylic acid (3‐carboxy‐4‐hydroxy­benzene­sulfonic acid) with 4‐X‐substituted anilines (X = F, Cl and Br), namely 4‐fluoro­anilinium 5‐sulfosalicylate (3‐carboxy‐4‐hydroxybenzenesulfonate) monohydrate, C₆H₇FN⁺·C₇H₅O₆S⁻·H₂O, (I), 4‐chloro­anilinium 5‐sulfosalicylate hemihydrate, C₆H₇ClN⁺·C₇H₅O₆S⁻·0.5H₂O, (II), and 4‐bromo­anilinium 5‐sulfosalicylate monohydrate, C₆H₇BrN⁺·C₇H₅O₆S⁻·H₂O, (III), have been determined. The asymmetric unit in (II) contains two formula units. All three compounds have three‐dimensional hydrogen‐bonded polymeric structures in which both the water molecule and the carboxylic acid group are involved in structure extension. With both (II) and (III), which are structurally similar, the common cyclic (8) dimeric carboxylic acid association is present, whereas in (I), an unusual cyclic (8) association involving all three hetero‐species is found.     

Ammonium 3‐cyano‐4‐(dicyano­methyl­ene)‐5‐oxo‐4,5‐dihydro‐1H‐pyrrol‐2‐olate monohydrate

Each anion of the title salt, NH₄⁺·C₈HN₄O₂⁻·H₂O, is linked by two N—H⋯O hydrogen bonds to another anion, thus forming an essentially planar centrosymmetric dimer. The dimers are considered to be mol­ecular building blocks of an anionic wall. The building blocks form infinite ribbons via–C—N⋯N—C– dipole–dipole and π–π inter­actions. Adjacent ribbons are stacked by means of π–π inter­actions, thus forming an anionic wall. Neighbouring walls are connected by (NH₄⁺…H₂O)_n chains running along the b axis.     

Hydrogen‐bonding motifs in 4‐carboxy­phenyl­ammonium nitrate and perchlorate monohydrate,and in bis(4‐carboxy­phenyl­ammonium) sulfate

In the title compounds, C₇H₈NO₂⁺·NO₃⁻, (I), C₇H₈NO₂⁺·ClO₄⁻·H₂O, (II), and 2C₇H₈NO₂⁺·SO₄²⁻, (III), the carboxyl planes of the 4‐carboxy­phenyl­ammonium cations are twisted from the aromatic plane. A homonuclear C(8) hydrogen‐bonding motif of 4‐carboxy­phenyl­ammonium cations is observed in both (I) and (II), leading to `head‐to‐tail' layers. The cations in (III) form carboxyl group dimers, making a graph‐set motif of R₂²(8). In all the structures, anions connect the cationic layers and an infinite chain running along the c axis is observed, having the C₂²(6) graph‐set motif. Inter­estingly, in (II), the anions are connected through weak hydrogen bonds involving the water mol­ecules, leading to a graph‐set motif of R₄⁴(12). Alternate hydro­phobic and hydro­philic layers are observed in all three compounds as a result of the column‐like arrangement of the aromatic rings of the cations and the anions. Furthermore, in (I), head‐to‐tail N—H⋯O inter­actions and inter­actions linking the cations and anions form an R₆⁴(16) hydrogen‐bonding motif, resulting in a pseudo‐inversion centre at (, , 0).     

Brucine salts of l‐α‐hydr­oxy acids: brucinium hydrogen (S)‐malate penta­hydrate and anhydrous brucinium hydrogen (2R,3R)‐tartrate at 130 K

The structures of two brucinium (2,3‐dimeth­oxy‐10‐oxostrychnidinium) salts of the α‐hydr­oxy acids l ‐malic acid and l ‐tartaric acid, namely brucinium hydrogen (S)‐malate penta­hydrate, C₂₃H₂₇N₂O₄⁺·C₄H₅O₅⁻·5H₂O, (I), and anhydrous brucinium hydrogen (2R,3R)‐tartrate, C₂₃H₂₇N₂O₄⁺·C₄H₅O₆⁻,(II), have been determined at 130 K. Compound (I) has two brucinium cations, two hydrogen malate anions and ten water mol­ecules of solvation in the asymmetric unit, and forms an extensively hydrogen‐bonded three‐dimensional framework structure. In compound (II), the brucinium cations form the common undulating brucine sheet substructures, which accommodate parallel chains of head‐to‐tail hydrogen‐bonded tartrate anion species in the inter­stitial cavities.     

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.     

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.     

Sodium pyridine‐3‐carboxyl­ate

The title compound, also known as sodium nicotinate, Na⁺·C₆H₄NO₂⁻, consists of two unique Na atoms coordinated to two unique pyridine‐3‐­carboxyl­ate ligands through the N atoms and carboxylate groups. One Na atom and one pyridine‐3‐­carboxyl­ate ligand lie on a twofold axis. Extensive Na coordination results in a three‐dimensional array comprising infinite NaO₂CR chains linked by intrachain Na—N bonds.     

2,2′‐(Iminodimethylene)bis(1H‐benzimidazolium)(1+) chloride

The title compound, C₁₆H₁₆N₅⁺·Cl⁻ (nbbH⁺·Cl⁻), displays N—H⋯N, N—H⋯Cl and π–π inter­actions in the crystal packing. The Cl⁻ anion is chelated by the nbbH⁺ cation via two N—H⋯Cl hydrogen bonds. Inter‐ion N—H⋯N and N—H⋯Cl hydrogen bonds link ions related by 2₁ screw axes into chains along the c axis. These chains are further linked by glide‐plane operations to generate a three‐dimensional network, which is additionally stabilized by inter­chain π–π inter­actions.