Two‐ and three‐dimensional hydrogen‐bonded structures in the 1:1 proton‐transfer compounds of 4,5‐dichlorophthalic acid with the isomeric monoaminobenzoic acids

The crystal structures of the 1:1 proton‐transfer compounds of 4,5‐dichlorophthalic acid with the three isomeric monoaminobenzoic acids, namely the hydrate 2‐carboxyanilinium 2‐carboxy‐4,5‐dichlorobenzoate dihydrate, C₇H₈NO₂⁺·C₈H₃Cl₂O₄⁻·2H₂O, (I), and the anhydrous salts 3‐carboxyanilinium 2‐carboxy‐4,5‐dichlorobenzoate, C₇H₈NO₂⁺·C₈H₃Cl₂O₄⁻, (II), and 4‐carboxyanilinium 2‐carboxy‐4,5‐dichlorobenzoate, C₇H₈NO₂⁺·C₈H₃Cl₂O₄⁻, (III), have been determined at 130 K. Compound (I) has a two‐dimensional hydrogen‐bonded sheet structure, while (II) and (III) are three‐dimensional. All three compounds feature sheet substructures formed through anilinium N⁺—H...O_carboxyl and anion carboxylic acid O—H...O_carboxyl interactions and, in the case of (I), additionally linked through the donor and acceptor associations of the solvent water molecules. However, (II) and (III) have additional lateral extensions of these substructures though cyclic R²₂(8) associations involving the carboxylic acid groups of the cations. Also, (II) and (III) have cation–anion π–π aromatic ring interactions. This work provides further examples illustrating the regular formation of network substructures in the 1:1 proton‐transfer salts of 4,5‐dichlorophthalic acid with the bifunctional aromatic amines.     

Low‐dimensional hydrogen‐bonded structures in the 1:1 and 1:2 proton‐transfer compounds of 4,5‐dichlorophthalic acid with the aliphatic Lewis bases triethylamine,diethylamine, n‐butylamine and piperidine

The structures of the proton‐transfer compounds of 4,5‐dichlorophthalic acid (DCPA) with the aliphatic Lewis bases triethylamine, diethylamine, n‐butylamine and piperidine, namely triethylaminium 2‐carboxy‐4,5‐dichlorobenzoate, C₆H₁₆N⁺·C₈H₃Cl₂O₄⁻, (I), diethylaminium 2‐carboxy‐4,5‐dichlorobenzoate, C₄H₁₂N⁺·C₈H₃Cl₂O₄⁻, (II), bis(butanaminium) 4,5‐dichlorobenzene‐1,2‐dicarboxylate monohydrate, 2C₄H₁₂N⁺·C₈H₂Cl₂O₄²⁻·H₂O, (III), and bis(piperidinium) 4,5‐dichlorobenzene‐1,2‐dicarboxylate monohydrate, 2C₅H₁₂N⁺·C₈H₂Cl₂O₄²⁻·H₂O, (IV), have been determined at 200 K. All compounds have hydrogen‐bonding associations, giving discrete cation–anion units in (I) and linear chains in (II), while (III) and (IV) both have two‐dimensional structures. In (I), a discrete cation–anion unit is formed through an asymmetric R₁²(4) N⁺—H...O₂ hydrogen‐bonding association, whereas in (II), chains are formed through linear N—H...O associations involving both aminium H‐atom donors. In compounds (III) and (IV), the primary N—H...O‐linked cation–anion units are extended into a two‐dimensional sheet structure via amide–carboxyl N—H...O and amide–carbonyl N—H...O interactions. In the 1:1 salts (I) and (II), the hydrogen 4,5‐dichlorophthalate anions are essentially planar with short intramolecular carboxyl–carboxyl O—H...O hydrogen bonds [O...O = 2.4223 (14) and 2.388 (2) Å, respectively]. This work provides a further example of the uncommon zero‐dimensional hydrogen‐bonded DCPA–Lewis base salt and the one‐dimensional chain structure type, while even with the hydrate structures of the 1:2 salts with the primary and secondary amines, the low dimensionality generally associated with 1:1 DCPA salts is also found.     

Zero‐, one‐ and two‐dimensional hydrogen‐bonded structures in the 1:1 proton‐transfer compounds of 4,5‐dichlorophthalic acid with the monocyclic heteroaromatic Lewis bases 2‐aminopyrimidine,nicotinamide and isonicotinamide

The structures of the anhydrous 1:1 proton‐transfer compounds of 4,5‐dichlorophthalic acid (DCPA) with the monocyclic heteroaromatic Lewis bases 2‐aminopyrimidine, 3‐(aminocarbonyl)pyridine (nicotinamide) and 4‐(aminocarbonyl)pyridine (isonicotinamide), namely 2‐aminopyrimidinium 2‐carboxy‐4,5‐dichlorobenzoate, C₄H₆N₃⁺·C₈H₃Cl₂O₄⁻, (I), 3‐(aminocarbonyl)pyridinium 2‐carboxy‐4,5‐dichlorobenzoate, C₆H₇N₂O⁺·C₈H₃Cl₂O₄⁻, (II), and the unusual salt adduct 4‐(aminocarbonyl)pyridinium 2‐carboxy‐4,5‐dichlorobenzoate–methyl 2‐carboxy‐4,5‐dichlorobenzoate (1/1), C₆H₇N₂O⁺·C₈H₃Cl₂O₄⁻·C₉H₆Cl₂O₄, (III), have been determined at 130 K. Compound (I) forms discrete centrosymmetric hydrogen‐bonded cyclic bis(cation–anion) units having both R₂²(8) and R₁²(4) N—H...O interactions. In (II), the primary N—H...O‐linked cation–anion units are extended into a two‐dimensional sheet structure via amide–carboxyl and amide–carbonyl N—H...O interactions. The structure of (III) reveals the presence of an unusual and unexpected self‐synthesized methyl monoester of the acid as an adduct molecule, giving one‐dimensional hydrogen‐bonded chains. In all three structures, the hydrogen phthalate anions are essentially planar with short intramolecular carboxyl–carboxylate O—H...O hydrogen bonds [O...O = 2.393 (8)–2.410 (2) Å]. This work provides examples of low‐dimensional 1:1 hydrogen‐bonded DCPA structure types, and includes the first example of a discrete cyclic `heterotetramer.' This low dimensionality in the structures of the 1:1 aromatic Lewis base salts of the parent acid is generally associated with the planar DCPA anion species.     

Three‐dimensional hydrogen‐bonded structures in the 1:1 proton‐transfer compounds of l‐tartaric acid with the associative‐group monosubstituted pyridines 3‐aminopyridine, 3‐carboxypyridine (nicotinic acid) and 2‐carboxypyridine (picolinic acid)

The 1:1 proton‐transfer compounds of l ‐tartaric acid with 3‐aminopyridine [3‐aminopyridinium hydrogen (2R,3R)‐tartrate dihydrate, C₅H₇N₂⁺·C₄H₅O₆⁻·2H₂O, (I)], pyridine‐3‐carboxylic acid (nicotinic acid) [anhydrous 3‐carboxypyridinium hydrogen (2R,3R)‐tartrate, C₆H₆NO₂⁺·C₄H₅O₆⁻, (II)] and pyridine‐2‐carboxylic acid [2‐carboxypyridinium hydrogen (2R,3R)‐tartrate monohydrate, C₆H₆NO₂⁺·C₄H₅O₆⁻·H₂O, (III)] have been determined. In (I) and (II), there is a direct pyridinium–carboxyl N⁺—H...O hydrogen‐bonding interaction, four‐centred in (II), giving conjoint cyclic R₁²(5) associations. In contrast, the N—H...O association in (III) is with a water O‐atom acceptor, which provides links to separate tartrate anions through O_hydroxy acceptors. All three compounds have the head‐to‐tail C(7) hydrogen‐bonded chain substructures commonly associated with 1:1 proton‐transfer hydrogen tartrate salts. These chains are extended into two‐dimensional sheets which, in hydrates (I) and (III) additionally involve the solvent water molecules. Three‐dimensional hydrogen‐bonded structures are generated via crosslinking through the associative functional groups of the substituted pyridinium cations. In the sheet struture of (I), both water molecules act as donors and acceptors in interactions with separate carboxyl and hydroxy O‐atom acceptors of the primary tartrate chains, closing conjoint cyclic R₄⁴(8), R₃⁴(11) and R₃³(12) associations. Also, in (II) and (III) there are strong cation carboxyl–carboxyl O—H...O hydrogen bonds [O...O = 2.5387 (17) Å in (II) and 2.441 (3) Å in (III)], which in (II) form part of a cyclic R₂²(6) inter‐sheet association. This series of heteroaromatic Lewis base–hydrogen l ‐tartrate salts provides further examples of molecular assembly facilitated by the presence of the classical two‐dimensional hydrogen‐bonded hydrogen tartrate or hydrogen tartrate–water sheet substructures which are expanded into three‐dimensional frameworks via peripheral cation bifunctional substituent‐group crosslinking interactions.     

Three‐dimensional hydrogen‐bonded structures in the hydrated proton‐transfer salts of isonipecotamide with the dicarboxylic oxalic and adipic acid homologues

The structures of the 1:1 hydrated proton‐transfer compounds of isonipecotamide (piperidine‐4‐carboxamide) with oxalic acid, 4‐carbamoylpiperidinium hydrogen oxalate dihydrate, C₆H₁₃N₂O⁺·C₂HO₄⁻·2H₂O, (I), and with adipic acid, bis(4‐carbamoylpiperidinium) adipate dihydrate, 2C₆H₁₃N₂O⁺·C₆H₈O₄²⁻·2H₂O, (II), are three‐dimensional hydrogen‐bonded constructs involving several different types of enlarged water‐bridged cyclic associations. In the structure of (I), the oxalate monoanions give head‐to‐tail carboxylic acid O—H...O_carboxyl hydrogen‐bonding interactions, forming C(5) chain substructures which extend along a. The isonipecotamide cations also give parallel chain substructures through amide N—H...O hydrogen bonds, the chains being linked across b and down c by alternating water bridges involving both carboxyl and amide O‐atom acceptors and amide and piperidinium N—H...O_carboxyl hydrogen bonds, generating cyclic R₄³(10) and R₃²(11) motifs. In the structure of (II), the asymmetric unit comprises a piperidinium cation, half an adipate dianion, which lies across a crystallographic inversion centre, and a solvent water molecule. In the crystal structure, the two inversion‐related cations are interlinked through the two water molecules, which act as acceptors in dual amide N—H...O_water hydrogen bonds, to give a cyclic R₄²(8) association which is conjoined with an R₄⁴(12) motif. Further N—H...O_water, water O—H...O_amide and piperidinium N—H...O_carboxyl hydrogen bonds give the overall three‐dimensional structure. The structures reported here further demonstrate the utility of the isonipecotamide cation as a synthon for the generation of stable hydrogen‐bonded structures. The presence of solvent water molecules in these structures is largely responsible for the non‐occurrence of the common hydrogen‐bonded amide–amide dimer, promoting instead various expanded cyclic hydrogen‐bonding motifs.     

The three‐dimensional hydrogen‐bonded framework structure in the 1:1 proton‐transfer compound of the drug quinacrine with 5‐sulfosalicylic acid

For the hydrated proton‐transfer compound 6‐chloro‐9‐[(4‐diethylammonio‐2‐methylbutyl)amino]‐2‐methoxyacridinium 3‐carboxylato‐4‐hydroxybenzenesulfonate dihydrate, C₂₃H₃₂ClN₃O²⁺·C₇H₄O₆S²⁻·2H₂O, (I), the conformational features, specifically those of the extended side chain at the 9‐position of the acridine parent, have been compared with those of quinacrinium dichloride dihydrate (the drug atabrine or mepacrine). Racemic compound (I) has a three‐dimensional hydrogen‐bonded framework structure similar to atabrine but also involves the water molecules and both the carboxylate and sulfonate groups of the anion in structure extension. The comparable conformational features found in this uncommon derivative of quinacrine indicate that (I) has potential as a possible pharmaceutical substitute for atabrine.     

4,6‐Diaminopyrimidine‐2(1H)‐thione hemihydrate: a three‐dimensional hydrogen‐bonded framework

In the title compound, C₄H₆N₄S·0.5H₂O, there are two independent pyrimidinethione units, both of which lie across mirror planes in the space group Cmca. Hence, the H atoms bonded to the ring N atoms in each molecule are disordered over two symmetry‐related sites, each having an occupancy of 0.5. The water molecule lies across a twofold rotation axis parallel to [010]. The molecular components of (I) are linked by seven independent hydrogen bonds, of N—H...N, N—H...S, N—H...O and O—H...S types. A combination of disordered N—H...N hydrogen bonds and ordered N—H...S hydrogen bonds links the pyrimidinethione units into a continuous tubular structure. The water molecule acts as both a double donor of hydrogen bonds and a double acceptor, forming hydrogen bonds with components of four distinct pyrimidinethione tubes, thus linking these tubes into a three‐dimensional structure.     

Proton‐transfer compounds of isonipecotamide with the aromatic dicarboxylic acids 4‐nitrophthalic, 4,5‐dichlorophthalic, 5‐nitroisophthalic and terephthalic acid

The structures of the 1:1 proton‐transfer compounds of isonipecotamide (piperidine‐4‐carboxamide) with 4‐nitrophthalic acid [4‐carbamoylpiperidinium 2‐carboxy‐4‐nitrobenzoate, C₆H₁₃N₂O₈⁺·C₈H₄O₆⁻, (I)], 4,5‐dichlorophthalic acid [4‐carbamoylpiperidinium 2‐carboxy‐4,5‐dichlorobenzoate, C₆H₁₃N₂O₈⁺·C₈H₃Cl₂O₄⁻, (II)] and 5‐nitroisophthalic acid [4‐carbamoylpiperidinium 3‐carboxy‐5‐nitrobenzoate, C₆H₁₃N₂O₈⁺·C₈H₄O₆⁻, (III)], as well as the 2:1 compound with terephthalic acid [bis(4‐carbamoylpiperidinium) benzene‐1,2‐dicarboxylate dihydrate, 2C₆H₁₃N₂O₈⁺·C₈H₄O₄²⁻·2H₂O, (IV)], have been determined at 200 K. All salts form hydrogen‐bonded structures, viz. one‐dimensional in (II) and three‐dimensional in (I), (III) and (IV). In (I) and (III), the centrosymmetric R₂²(8) cyclic amide–amide association is found, while in (IV) several different types of water‐bridged cyclic associations are present [graph sets R₄²(8), R₄³(10), R₄⁴(12), R₃³(18) and R₆⁴(22)]. The one‐dimensional structure of (I) features the common `planar' hydrogen 4,5‐dichlorophthalate anion, together with enlarged cyclic R₃³(13) and R₄³(17) associations. In the structures of (I) and (III), the presence of head‐to‐tail hydrogen phthalate chain substructures is found. In (IV), head‐to‐tail primary cation–anion associations are extended longitudinally into chains through the water‐bridged cation associations, and laterally by piperidinium–carboxylate N—H...O and water–carboxylate O—H...O hydrogen bonds. The structures reported here further demonstrate the utility of the isonipecotamide cation as a synthon for the generation of stable hydrogen‐bonded structures. An additional example of cation–anion association with this cation is also shown in the asymmetric three‐centre piperidinium–carboxylate N—H...O,O′ interaction in the first‐reported structure of a 2:1 isonipecotamide–carboxylate salt.     

Three‐dimensional hydrogen‐bonded structures in the guanidinium salts of the monocyclic dicarboxylic acids rac‐trans‐cyclohexane‐1,2‐dicarboxylic acid (2:1, anhydrous), isophthalic acid (1:1, monohydrate) and terephthalic acid (2:1, trihydrate)

The structures of bis(guanidinium) rac‐trans‐cyclohexane‐1,2‐dicarboxylate, 2CH₆N₃⁺·C₈H₁₀O₄²⁻, (I), guanidinium 3‐carboxybenzoate monohydrate, CH₆N₃⁺·C₈H₅O₄⁻·H₂O, (II), and bis(guanidinium) benzene‐1,4‐dicarboxylate trihydrate, 2CH₆N₃⁺·C₈H₄O₄²⁻·3H₂O, (III), all reveal three‐dimensional hydrogen‐bonded framework structures. In anhydrous (I), both guanidinium cations form classic cyclic R₂²(8) N—H...O,O′_carboxylate and asymmetric cyclic R₂¹(6) hydrogen‐bonding interactions, while one cation forms an unusual enlarged cyclic interaction with O‐atom acceptors of separate ortho‐related carboxylate groups [graph set R₂²(11)]. Cations and anions also associate across inversion centres, giving cyclic R₄²(8) motifs. In the 1:1 guanidinium salt, (II), the cation forms two separate cyclic R₂¹(6) interactions, one with a carboxyl O‐atom acceptor and the other with the solvent water molecule. The structure is unusual in that both carboxyl groups form short interanion O...H...O contacts, one across a crystallographic inversion centre [O...O = 2.483 (2) Å] and the other about a twofold axis of rotation [O...O = 2.462 (2) Å], representing shared sites on these elements for the single acid H atom. The water molecule links the cation–anion ribbon structures into a three‐dimensional framework. In (III), the repeating molecular unit comprises a benzene‐1,4‐dicarboxylate dianion which lies across a crystallographic inversion centre, two guanidinium cations and two solvent water molecules (each set related by twofold rotational symmetry), and a single water molecule which lies on a twofold axis. Each guanidinium cation forms three types of cyclic interaction with the dianions: one R₂¹(6), the others R₃²(8) and R₃³(10) (both of these involving the water molecules), giving a three‐dimensional structure through bridges down the b‐cell direction. The water molecule at the general site also forms an unusual cyclic R₂²(4) homodimeric association across an inversion centre [O...O = 2.875 (2) Å]. The work described here provides further examples of the common cyclic guanidinium–carboxylate hydrogen‐bonding associations, as well as featuring other less common cyclic motifs.     

Phenyl‐ring rotational disorder in the two‐dimensional hydrogen‐bonded structure of the 1:1 proton‐transfer salt of the diazo‐dye precursor 4‐(phenyldiazenyl)aniline (aniline yellow) with l‐tartaric acid

In the structure of the 1:1 proton‐transfer compound from the reaction of l ‐tartaric acid with the azo‐dye precursor aniline yellow [4‐(phenyldiazenyl)aniline], namely 4‐(phenyldiazenyl)anilinium (2R,3R)‐3‐carboxy‐2,3‐dihydroxypropanoate, C₁₂H₁₂N₃⁺·C₄H₅O₆⁻, the asymmetric unit contains two independent 4‐(phenyldiazenyl)anilinium cations and two hydrogen l ‐tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen l ‐tartrate anions form independent but similar chains through head‐to‐tail carboxyl–carboxylate O—H...O hydrogen bonds [graph set C(7)], which are then extended into a two‐dimensional hydrogen‐bonded sheet structure through hydroxy O—H...O hydrogen‐bonded links. The anilinium groups of the 4‐(phenyldiazenyl)anilinium cations are incorporated into the sheets and also provide internal hydrogen‐bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π–π interactions [minimum ring centroid separation = 3.844 (3) Å]. The hydrogen l ‐tartrate residues of both anions exhibit the common short intramolecular hydroxy–carboxylate O—H...O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in molecular assembly processes.     

Three‐dimensional hydrogen‐bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4‐toluenesulfonate) dihydrate

The structures of two salts of flunarizine, namely 1‐bis[(4‐fluorophenyl)methyl]‐4‐[(2E)‐3‐phenylprop‐2‐en‐1‐yl]piperazine, C₂₆H₂₆F₂N₂, are reported. In flunarizinium nicotinate {systematic name: 4‐bis[(4‐fluorophenyl)methyl]‐1‐[(2E)‐3‐phenylprop‐2‐en‐1‐yl]piperazin‐1‐ium pyridine‐3‐carboxylate}, C₂₆H₂₇F₂N₂⁺·C₆H₄NO₂⁻, (I), the two ionic components are linked by a short charge‐assisted N—H...O hydrogen bond. The ion pairs are linked into a three‐dimensional framework structure by three independent C—H...O hydrogen bonds, augmented by C—H...π(arene) hydrogen bonds and an aromatic π–π stacking interaction. In flunarizinediium bis(4‐toluenesulfonate) dihydrate {systematic name: 1‐[bis(4‐fluorophenyl)methyl]‐4‐[(2E)‐3‐phenylprop‐2‐en‐1‐yl]piperazine‐1,4‐diium bis(4‐methylbenzenesulfonate) dihydrate}, C₂₆H₂₈F₂N₂²⁺·2C₇H₇O₃S⁻·2H₂O, (II), one of the anions is disordered over two sites with occupancies of 0.832 (6) and 0.168 (6). The five independent components are linked into ribbons by two independent N—H...O hydrogen bonds and four independent O—H...O hydrogen bonds, and these ribbons are linked to form a three‐dimensional framework by two independent C—H...O hydrogen bonds, but C—H...π(arene) hydrogen bonds and aromatic π–π stacking interactions are absent from the structure of (II). Comparisons are made with some related structures.     

Crystal structure,characterization and catalytic activities of Cu(II) coordination complexes with 8‐hydroxyquinoline and pyrazine‐2‐carboxylic acid

Green and blue crystals of the coordination complexes [Cu(8‐hquin)₂(H₂O)₂], 1 and [Cu(pyzca)₂(H₂O)₂], 2 were obtained by the reaction of copper chloride with 8‐hydroxyquinoline (8‐hquinH) or pyrazine‐2‐carboxylic acid (pyzcaH) as ligands. The structures of 1 and 2 were characterized by elemental analyses, electronic absorption, Infrared (IR) and thermal studies. The luminescent behavior complexes 1 and 2 was also discussed. The coordination environment of copper(II) center displays distorted octahedral coordination geometry. The structure of the complexes 1 and 2 is constructed by an infinite number of discrete mononuclear molecules extending along the a‐axis to form a 1D‐chain via H‐bonds. The extensive hydrogen bonds and short contacts develop the structures of 1 and 2 to 3D‐network. The catalytic behavior of the complexes 1 and 2 was utilized for degradation of methylene blue dye (MB). The kinetic data indicated that the complexes 1 and 2 are effective catalysts for degradation of MB dye. Photoluminescence probing technology was used as a sensitive probe for detecting ^?OH radicals.     

The three‐dimensional hydrogen‐bonded structures in the ammonium and sodium salt hydrates of 4‐aminophenylarsonic acid

The structures of two hydrated salts of 4‐aminophenylarsonic acid (p‐arsanilic acid), namely ammonium 4‐aminophenylarsonate monohydrate, NH₄⁺·C₆H₇AsNO₃⁻·H₂O, (I), and the one‐dimensional coordination polymer catena‐poly[[(4‐aminophenylarsonato‐κO)diaquasodium]‐μ‐aqua], [Na(C₆H₇AsNO₃)(H₂O)₃]_n, (II), have been determined. In the structure of the ammonium salt, (I), the ammonium cations, arsonate anions and water molecules interact through inter‐species N—H...O and arsonate and water O—H...O hydrogen bonds, giving the common two‐dimensional layers lying parallel to (010). These layers are extended into three dimensions through bridging hydrogen‐bonding interactions involving the para‐amine group acting both as a donor and an acceptor. In the structure of the sodium salt, (II), the Na⁺ cation is coordinated by five O‐atom donors, one from a single monodentate arsonate ligand, two from monodentate water molecules and two from bridging water molecules, giving a very distorted square‐pyramidal coordination environment. The water bridges generate one‐dimensional chains extending along c and extensive interchain O—H...O and N—H...O hydrogen‐bonding interactions link these chains, giving an overall three‐dimensional structure. The two structures reported here are the first reported examples of salts of p‐arsanilic acid.     

Hydro­gen bonding in proton‐transfer compounds of 8‐quinolinol (oxine) with aromatic sulfonic acids

The crystal structures of the proton‐transfer compounds of 8‐quinolinol (oxine) with the aromatic sulfonic acids 2‐amino­benzene­sulfonic acid (orthanilic acid) and 8‐hydroxy‐7‐iodo­quinoline‐5‐sulfonic acid (ferron) have been determined. In both 8‐hydroxy­quinolinium 2‐amino­benzene­sulfonate, C₉H₈NO⁺·C₆H₆NO₃S⁻, (I), and 8‐hydroxyquino­linium 8‐hydroxy‐7‐iodo­quinoline‐5‐sulfonate ses­qui­hydrate, C₉H₈NO⁺·C₉H₆INO₄S⁻·1.5H₂O, (II), extensive hydrogen‐bonding interactions, together with significant cation–cation [in (I)] and cation–anion [in (II)] π–π stacking associations, give rise to layered polymer structures.     

(2S)‐1‐Carbamoylpyrrolidine‐2‐carboxylic acid

In the title compound, also known as N‐carbamoyl‐l ‐proline, C₆H₁₀N₂O₃, the pyrrolidine ring adopts a half‐chair conformation, whereas the carboxyl group and the mean plane of the ureide group form an angle of 80.1 (2)°. Molecules are joined by N—H...O and O—H...O hydrogen bonds into cyclic structures with graph‐set R²₂(8), forming chains in the b‐axis direction that are further connected via N—H...O hydrogen bonds into a three‐dimensional network.     

Synthesis and Cyclization of 8‐Formyl‐2‐(phenoxymethyl)quinoline‐3‐carboxylic Acids

A facile synthesis of a series of new quinoline‐8‐carbaldehyde compounds, namely 8‐formyl‐2‐(phenoxymethyl)quinoline‐3‐carboxylic acids ( 4a – 4h ) and 13‐oxo‐6,13‐dihydro[1]benzoxepino[3,4‐b]quinoline‐8‐carbaldehyde ( 5a – 5g ) is described, involving the one‐pot synthesis reaction of ethyl 2‐(chloromethyl)‐8‐formylquinoline‐3‐carboxylate ( 3 ) with substituted phenols followed by the intramolecular cyclization reaction via the treatment with polyphosphoric acid (PPA). Quinoline‐8‐carbaldehydes 4a – 4h and 5a – 5g are novel and their structures were supported by IR, ¹H NMR, ¹³C NMR, MS and elemental analysis.     

A three‐dimensional hydrogen‐bonded network in bis(4‐hydroxyanilinium) selenate(VI) dihydrate

The title compound, 2C₆H₈NO⁺·SeO₄²⁻·2H₂O, contains 4‐hydroxyanilinium cations, selenate(VI) anions and water molecules. One of the two independent cations is nearly planar (excluding the ammonium H atoms), while the other is markedly nonplanar, with the hydroxy and ammonium groups displaced from the plane of the benzene ring. This results from the antiparallel orientation of the cations, which interact through oppositely polarized ammonium and hydroxy groups. Ionic and hydrogen‐bonding interactions join the oppositely charged units into a three‐dimensional network. This work demonstrates the usefulness of 4‐aminophenol in the crystal engineering of organic–inorganic hybrid compounds.     

3‐(1H‐Pyrrol‐2‐yl)‐1H‐pyrazole forms an unusual hydrogen‐bonded two‐dimensional (3,4)‐connected net

The title compound, C₇H₇N₃, is the first crystallographically characterized 1H‐pyrrolyl‐1H‐pyrazole derivative and contains two unique molecules in its asymmetric unit (Z′ = 2). These molecules associate into centrosymmetric tetramers through N—H...N hydrogen bonding, including a cyclic dimerization of one of the two unique pyrazole rings. These tetramers are linked further by two weaker N—H...π contacts to give a novel two‐dimensional (3,4)‐connected net with a (3².8)₂(3.8²)₂ topology.     

Three‐dimensional hydrogen‐bonded framework in bis(melamin‐1‐ium) naphthalene‐1,5‐disulfonate melamine pentahydrate

Crystals of the title compound, 2C₃H₇N₆⁺·C₁₀H₆O₆S₂²⁻·C₃H₆N₆·5H₂O, are built up of neutral 2,4,6‐triamino‐1,3,5‐triazine (melamine), singly protonated melaminium cations, naphthalene‐1,5‐disulfonate dianions and water molecules. Two independent anions lie across centres of inversion in the space group P. The melamine molecules are connected by N—H...N hydrogen bonds into two different one‐dimensional polymers almost parallel to the (010) plane, forming a stacking structure along the b axis. The centrosymmetric naphthalene‐1,5‐disulfonate anions interact with water molecules via O—H...O hydrogen bonds, forming layers parallel to the (001) plane. The cations and anions are connected by N—H...O and O—H...N hydrogen bonds to form a three‐dimensional supramolecular framework.     

A hydrogen‐bonded heterodimer of 1‐(4‐hexyloxyphenyl)pyridin‐4(1H)‐one with 4‐cyano­benzoic acid

The two components of the title heterodimer, C₁₇H₂₁NO₂·C₈H₅NO₂, are linked end‐to‐end via O—H⋯O(=C) and C—H⋯O(=C) hydrogen‐bond inter­actions. Additional lateral C—H⋯O inter­actions link the dimers in a side‐by‐side fashion to produce wide infinite mol­ecular ribbons. Adjacent ribbons are inter­connected viaπ–π stacking and C—H⋯π(arene) inter­actions. This structure represents the first evidence of robust hydrogen‐bond formation between the moieties of pyridin‐4(1H)‐one and benzoic acid.