The asymmetric unit of the title compound, C15H21N3OS, comprises of two crystallographically independent mol­ecules (A and B). Each mol­ecule consists of a cyclo­hexane ring and a 2-hy­droxy-3-methyl­benzyl­idene ring bridged by a hydrazinecarbo­thio­amine unit. Both mol­ecules exhibit an E configuration with respect to the azomethine C=N bond. There is an intra­molecular O—H⋯N hydrogen bond in each mol­ecule forming an S(6) ring motif. The cyclo­hexane ring in each mol­ecule has a chair conformation. The benzene ring is inclined to the mean plane of the cyclo­hexane ring by 47.75 (9)° in mol­ecule A and 66.99 (9)° in mol­ecule B. The mean plane of the cyclo­hexane ring is inclined to the mean plane of the thio­urea moiety [N—C(=S)—N] by 55.69 (9) and 58.50 (8)° in mol­ecules A and B, respectively. In the crystal, the A and B mol­ecules are linked by N—H⋯S hydrogen bonds, forming `dimers'. The A mol­ecules are further linked by a C—H⋯π inter­action, hence linking the A–B units to form ribbons propagating along the b-axis direction. The conformation of a number of related cyclo­hexa­nehydrazinecarbo­thio­amides are compared to that of the title compound.

This study is an investigation into the crystal structure of the biologically active drug mol­ecule riluzole [RZ, 6-(tri­fluoro­meth­oxy)-1,3-benzo­thia­zol-2-amine], C8H5F3N2OS, and its derivative, the riluzolium chloride salt [RZHCl, 2-amino-6-(tri­fluoro­meth­oxy)-1,3-benzo­thia­zol-3-ium chloride], C8H6F3N2OS+·Cl−. In spite of repeated efforts to crystallize the drug, its crystal structure has not been reported to date, hence the current study provides a method for obtaining crystals of both riluzole and its corresponding salt, riluzolium hydro­chloride. The salt was obtained by grinding HCl with the drug and crystallizing the obtained solid from di­chloro­methane. The crystals of riluzole were obtained in the presence of l-glutamic acid and d-glutamic acid in separate experiments. In the crystal structure of RZHCl, the –OCF3 moiety is perpendicular to the mol­ecular plane containing the riluzolium ion, as can be seen by the torsion angle of 107.4 (3)°. In the case of riluzole, the torsion angles of the four different mol­ecules in the asymmetric unit show that in three cases the tri­fluoro­meth­oxy group is perpendicular to the riluzole mol­ecular plane and only in one mol­ecule does the –OCF3 group lie in the same mol­ecular plane. The crystal structure of riluzole primarily consists of strong N—H⋯N hydrogen bonds along with weak C—H⋯F, C—H⋯S, F⋯F, C⋯C and C⋯S inter­actions, while that of its salt is stabilized by strong [N—H]+⋯Cl− and weak C—H⋯Cl−, N—H⋯S, C—H⋯F, C⋯C, S⋯N and S⋯Cl− inter­actions.

Five new crystal structures of perfluoro­pyridine substituted in the 4-position with phen­oxy, 4-bromo­phen­oxy, naphthalen-2-yl­oxy, 6-bromo­naphthalen-2-yl­oxy, and 4,4'-biphen­oxy are reported, viz. 2,3,5,6-tetra­fluoro-4-phen­oxy­pyridine, C11H5F4NO (I), 4-(4-bromo­phen­oxy)-2,3,5,6-tetra­fluoro­pyridine, C11H4BrF4NO (II), 2,3,5,6-tetra­fluoro-4-[(naphthalen-2-yl)­oxy]pyridine, C15H7F4NO (III), 4-[(6-bromo­naphthalen-2-yl)­oxy]-2,3,5,6-tetra­fluoropyridine, C15H6BrF4NO (IV), and 2,2'-bis­[(perfluoro­pyridin-4-yl)­oxy]-1,1'-biphenyl, C22H8F8N2O2 (V). The dihedral angles between the aromatic ring systems in I–IV are 78.74 (8), 56.35 (8), 74.30 (7), and 64.34 (19)°, respectively. The complete mol­ecule of V is generated by a crystallographic twofold axis: the dihedral angle between the pyridine ring and adjacent phenyl ring is 80.89 (5)° and the equivalent angle between the biphenyl rings is 27.30 (5)°. In each crystal, the packing is driven by C—H⋯F inter­actions, along with a variety of C—F⋯π, C—H⋯π, C—Br⋯N, C—H⋯N, and C—Br⋯π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing.

The title compound, C11H8O5·(CH3)2SO, is a new coumarin derivative. The asymmetric unit contains two coumarin mol­ecules (A and B) and two di­methyl­sulfoxide solvent mol­ecules (A and B). The dihedral angle between the pyran and benzene rings in the chromene moiety is 3.56 (2)° for mol­ecule A and 1.83 (2)° for mol­ecule B. In mol­ecule A, the dimethyl sulfoxide sulfur atom is disordered over two positions with a refined occupancy ratio of 0.782 (5):0.218 (5). In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains running along the c-axis direction. The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ac plane. In addition, there are also C—H⋯π and π–π inter­actions present within the layers. The inter­molecular contacts in the crystal have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots, which indicate that the most important contributions to the packing are from H⋯H (33.9%) and O⋯H/H⋯O (41.2%) contacts.

In the title metal–organic framework, [Fe(C6H8N2)2{Cu(CN)2}2]n, the low-spin FeII ion lies at an inversion centre and displays an elongated octa­hedral [FeN6] coordination environment. The axial positions are occupied by two symmetry-related bridging 2-ethyl­pyrazine ligands, while the equatorial positions are occupied by four N atoms of two pairs of symmetry-related cyanide groups. The CuI centre is coordinated by three cyanide carbon atoms and one N atom of a bridging 2-ethyl­pyrazine mol­ecule, which form a tetra­hedral coordination environment. Two neighbouring Cu atoms have a short Cu⋯Cu contact [2.4662 (7) Å] and their coordination tetra­hedra are connected through a common edge between two C atoms of cyanide groups. Each Cu2(CN)2 unit, formed by two neighbouring Cu atoms bridged by two carbons from a pair of μ-CN groups, is connected to six FeII centres via two bridging 2-ethyl­pyrazine mol­ecules and four cyanide groups, resulting in the formation of a polymeric three-dimensional metal–organic coordination framework.

The asymmetric unit of the title 1:1 solvate, C14H14N4O2·C6H6 [systematic name of the oxalamide mol­ecule: N,N'-bis­(pyridin-4-ylmeth­yl)ethanedi­amide], comprises a half mol­ecule of each constituent as each is disposed about a centre of inversion. In the oxalamide mol­ecule, the central C2N2O2 atoms are planar (r.m.s. deviation = 0.0006 Å). An intra­molecular amide-N—H⋯O(amide) hydrogen bond is evident, which gives rise to an S(5) loop. Overall, the mol­ecule adopts an anti­periplanar disposition of the pyridyl rings, and an orthogonal relationship is evident between the central plane and each terminal pyridyl ring [dihedral angle = 86.89 (3)°]. In the crystal, supra­molecular layers parallel to (10overline{2}) are generated owing the formation of amide-N—H⋯N(pyrid­yl) hydrogen bonds. The layers stack encompassing benzene mol­ecules which provide the links between layers via methyl­ene-C—H⋯π(benzene) and benzene-C—H⋯π(pyrid­yl) inter­actions. The specified contacts are indicated in an analysis of the calculated Hirshfeld surfaces. The energy of stabilization provided by the conventional hydrogen bonding (approximately 40 kJ mol−1; electrostatic forces) is just over double that by the C—H⋯π contacts (dispersion forces).

In the title polymeric complex, {[Fe(CN)2(C10H8N2)2(H2O)2][Au(CN)2]}n, the FeII ion, which is located on a twofold rotation axis, has a slightly distorted FeN4O2 octa­hedral geometry. It is coordinated by two phenyl­pyrazine mol­ecules, two water mol­ecules and two di­cyano­aurate anions, the Au atom also being located on a second twofold rotation axis. In the crystal, the coordinated di­cyano­aurate anions bridge the FeII ions to form polymeric chains propagating along the b-axis direction. In the crystal, the chains are linked by Owater—H⋯Ndi­cyano­aurate anions hydrogen bonds and aurophillic inter­actions [Au⋯Au = 3.5661 (3) Å], forming layers parallel to the bc plane. The layers are linked by offset π–π stacking inter­actions [inter­centroid distance = 3.643 (3) Å], forming a supra­molecular metal–organic framework.

The syntheses and crystal structures of the title compounds, C14H8F4N2O2 and C14H8F4N2O3, are reported. In each crystal, the packing is driven by C—H⋯F inter­tactions, along with a variety of C—H⋯O, C—O⋯π, and C—F⋯π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing: they showed that the largest contributions to the surface contacts arise from H⋯F/F⋯H inter­actions, followed by H⋯H and O⋯H/H⋯O.

The title coordination polymer, {[Cu3(C4H4N3O9)3(SeO4)(OH)]·2H2O}n or ([Cu3(μ3-OH)(trgly)3(SeO4)]·2H2O), crystallizes in the monoclinic space group P21/c. The three independent Cu2+ cations adopt distorted square-pyramidal geometries with {O2N2+O} polyhedra. The three copper centres are bridged by a μ3-OH anion, leading to a triangular [Cu3(μ3-OH)] core. 2-(1,2,4-Triazol-4-yl)acetic acid (trgly-H) acts in a deprotonated form as a μ3-κ3N1:N2:O ligand. The three triazolyl groups bridge three copper centres of the hydroxo-cluster in an N1:N2 mode, thus supporting the triangular geometry. The [Cu3(μ3-OH)(tr)3] clusters serve as secondary building units (SBUs). Each SBU can be regarded as a six-connected node, which is linked to six neighbouring triangles through carboxyl­ate groups, generating a two-dimensional uninodal (3,6) coordination network. The selenate anion is bound in a μ3-κ3O1:O2:O3 fashion to the trinuclear copper platform. The [Cu3(OH)(trgly)3(SeO4)] coordination layers and guest water mol­ecules are linked together by numerous O—H⋯O and C—H⋯O hydrogen bonds, leading to a three-dimensional structure.

In the title compound, C27H30N4O6·H2O, the two dioxolo rings are in envelope conformations, while the pyran ring is in a twisted-boat conformation. The pyradizine ring is oriented at dihedral angles of 9.23 (6) and 12.98 (9)° with respect to the pyridine rings, while the dihedral angle between the two pyridine rings is 13.45 (10)°. In the crystal, O—Hwater⋯Opyran, O—Hwater⋯Ometh­oxy­meth­yl and O—Hwater⋯Npyridazine hydrogen bonds link the mol­ecules into chains along [010]. In addition, weak C—Hdioxolo⋯Odioxolo hydrogen bonds and a weak C—Hmeth­oxy­meth­yl⋯π inter­action complete the three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (55.7%), H⋯C/C⋯H (14.6%), H⋯O/O⋯H (14.5%) and H⋯N/N⋯H (9.6%) inter­actions. Hydrogen-bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Electrochemical measurements are also reported.

The crystal structure of the title compound, [Ni(C63H31F10N5S2)]·xCH2Cl2 (x > 1/2), consists of Ni–porphyrin complexes that are located in general positions and di­chloro­methane solvent mol­ecules that are disordered around centers of inversion. The NiII ions are in a square-pyramidal (CN5) coordination, with four porphyrin N atoms in the equatorial and a pyridine N atom in the apical position and are shifted out of the porphyrine N4 plane towards the coordinating pyridine N atom. The pyridine substituent is not exactly perpendicular to the N4 plane with an angle of inter­section between the planes planes of 80.48 (6)°. The di­chloro­methane solvent mol­ecules are hydrogen bonded to one of the four porphyrine N atoms. Two complexes are linked into dimers by two symmetry-equivalent C—H⋯S hydrogen bonds. These dimers are closely packed, leading to cavities in which additional di­chloro­methane solvent mol­ecules are embedded. These solvent mol­ecules are disordered and because no reasonable split model was found, the data were corrected for disordered solvent using the PLATON SQUEEZE routine [Spek (2015). Acta Cryst. C71, 9–18].

The title salt, C16H15ClN3S+·Br−, is isotypic with (E)-3-[(4-fluoro­benzyl­idene)amino]-5-phenyl­thia­zolidin-2-iminium bromide [Khalilov et al. (2019). Acta Cryst. E75, 662–666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thia­zolidine ring and the atom joining the thia­zolidine ring to the benzene ring are disordered over two sets of sites with occupancies of 0.570 (3) and 0.430 (3). The major and minor components of the disordered thia­zolidine ring adopt slightly distorted envelope conformations, with the C atom bearing the phenyl ring as the flap atom. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N—H⋯Br hydrogen bonds, which are further connected by weak C—H⋯Br contacts into chains parallel to the a axis. Furthermore, not existing in the earlier report of (E)-3-[(4-fluoro­benzyl­idene)amino]-5-phenyl­thia­zolidin-2-iminium bromide, C—H⋯π inter­actions and π–π stacking inter­actions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the mol­ecular packing. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions for the crystal packing are from H⋯H (30.5%), Br⋯H/H⋯Br (21.2%), C⋯H/H⋯C (19.2%), Cl⋯H/H⋯Cl (13.0%) and S⋯H/H⋯S (5.0%) inter­actions.

The monocation product of the oxidative condensation–cyclization between two mol­ecules of pyridine-2-carbaldehyde and one mol­ecule of CH3NH2·HCl in methanol, 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium, was isolated in the presence of metal ions as bis­[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] tetra­iodo­cadmate, (C13H12N3)2[CdI4], (I), and the mixed chloride/nitrate salt, bis­[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] 1.5-chlor­ide 0.5-nitrate trihydrate, 2C13H12N3+·1.5Cl−·0.5NO3−·3H2O, (II). Hybrid salt (I) crystallizes in the space group P21/n with two [L]2[CdI4] mol­ecules in the asymmetric unit related by pseudosymmetry. In the crystal of (I), layers of organic cations and of tetra­halometallate anions are stacked parallel to the ab plane. Anti­parallel L+ cations disposed in a herring-bone pattern form π-bonded chains through aromatic stacking. In the inorganic layer, adjacent tetra­hedral CdI4 units have no connectivity but demonstrate close packing of iodide anions. In the crystal lattice of (II), the cations are arranged in stacks propagating along the a axis; the one-dimensional hydrogen-bonded polymer built of chloride ions and water mol­ecules runs parallel to a column of stacked cations.

The asymmetric unit of the title compound, C12H22N+·CH3O3S−, consists of three (3,5-di­methyl­adamantan-1-yl)ammonium cations, C12H22N+, and three methane­sulfonate anions, CH3O3S−. In the crystal, the cations and anions associate via N—H⋯O hydrogen bonds into layers, parallel to the (001) plane, which include large supra­molecular hydrogen-bonded rings.

The title compound, C8H4Br2O4·C2H6O2, crystallizes with one-half of a 2,5-di­bromo­terephthalic acid (H2Br2tp) mol­ecule and one-half of an ethyl­ene glycol (EG) mol­ecule in the the asymmetric unit. The whole mol­ecules are generated by application of inversion symmetry. The H2Br2tp mol­ecule is not planar, with the di­bromo­benzene ring system inclined by a dihedral angle of 18.62 (3)° to the carb­oxy­lic group. In the crystal, the H2Br2tp and EG mol­ecules are linked into sheets propagating parallel to (overline{1}01) through O—H⋯O hydrogen bonds, thereby forming R44 (12) and R44 (28) graph-set motifs. Br⋯O and weak π–π stacking inter­actions are also observed. Hirshfeld surface analysis was used to confirm the existence of these inter­actions.

The syntheses and crystal structures of three hybrid perovskites, viz. poly[1-methyl­piperizine-1,4-diium [tri-μ-bromido-potassium] hemihydrate], {(C5H14N2)[KBr3]·0.5H2O}n, (I), poly[1-methyl­piperizine-1,4-diium [tri-μ-bromido-rubidium] hemihydrate], {(C5H14N2)[RbBr3]·0.5H2O}n, (II), and poly[1-methyl­piperizine-1,4-diium [tri-μ-bromido-caesium] hemihydrate], {(C5H14N2)[CsBr3]·0.5H2O}n, (III), are described. These isostructural (space group Amm2) phases contain a three-dimensional, corner-sharing network of distorted ABr6 octa­hedra (A = K, Rb, Cs) with the same topology as the classical perovskite structure. The doubly protonated C5H14N22+ cations occupy inter­stices bounded by eight octa­hedra and the water mol­ecules lie in square sites bounded by four octa­hedra. N—H⋯Br, N—H⋯(Br,Br), N—H⋯O and O—H⋯Br hydrogen bonds consolidate the structures.

The isostructural title compounds, poly[piperazin-1-ium [di-μ-bromido-caesium]], {(C4H11N2)[CsBr2]}n, and poly[piperazin-1-ium [di-μ-bromido-rubidium]], {(C4H11N2)[RbBr2]}n, contain singly-protonated piperazin-1-ium cations and unusual ABr6 (A = Cs or Rb) trigonal prisms. The prisms are linked into a distinctive `curtain wall' arrangement propagating in the (010) plane by face and edge sharing. In each case, a network of N—H⋯N, N—H⋯Br and N—H⋯(Br,Br) hydrogen bonds consolidates the structure.

Bidentate and tridentate coordination of a 2,4-di-tert-butyl-substituted bridging amine bis­(phenolate) ligand to a palladium(II) center are observed within the same crystal structure, namely di­chlorido­({6,6'-[(ethane-1,2-diylbis(methyl­aza­nedi­yl)]bis­(methyl­ene)}bis­(2,4-di-tert-butyl­phenol))palladium(II) chlorido­(2,4-di-tert-butyl-6-{[(2-{[(3,5-di-tert-butyl-2-hy­droxy­phen­yl)meth­yl](meth­yl)amino}­eth­yl)(meth­yl)amino]­meth­yl}phenolato)palladium(II) methanol 1.685-solvate 0.315-hydrate, [PdCl2(C34H56N2O2)][PdCl(C34H55N2O2)]·1.685CH3OH·0.315H2O. Both complexes exhibit a square-planar geometry, with unbound phenol moieties participating in inter­molecular hydrogen bonding with co-crystallized water and methanol. The presence of both κ2 and κ3 coordination modes arising from the same solution suggest a dynamic process in which phenol donors may coordinate or dissociate from the metal center, and offers insight into catalyst speciation throughout Pd-mediated processes. The unit cell contains di­chlorido­({6,6'-[(ethane-1,2-diylbis(methyl­aza­nedi­yl)]bis­(methyl­ene)}bis­(2,4-di-tert-butyl­phenol))palladium(II), {(L2)PdCl2}, and chlorido­(2,4-di-tert-butyl-6-{[(2-{[(3,5-di-tert-butyl-2-hy­droxy­phen­yl)meth­yl](methyl)amino}eth­yl)(meth­yl)amino]­meth­yl}phenolato)palladium(II), {(L2X)PdCl}, mol­ecules as well as fractional water and methanol solvent mol­ecules.

In the title benzohydrazide derivative, C14H12N2O4, the azomethine C=N double bond has an E configuration. The hydrazide connecting bridge, (C=O)—(NH)—N=(CH), is nearly planar with C—C—N—N and C—N—N=C torsion angles of −177.33 (10) and −174.98 (12)°, respectively. The 4-hy­droxy­phenyl and 3,4-di­hydroxy­phenyl rings are slightly twisted, making a dihedral angle of 9.18 (6)°. In the crystal, mol­ecules are connected by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional network, while further consolidated via π–π inter­actions [centroid–centroid distances = 3.6480 (8) and 3.7607 (8) Å]. The conformation is compared to those of related benzyl­idene-4-hy­droxy­benzohydrazide derivatives.

Four manganese(II) bromide coordination complexes have been prepared with four pyridine N-oxides, viz. pyridine N-oxide (PNO), 2-methyl­pyridine N-oxide (2MePNO), 3-methyl­pyridine N-oxide (3MePNO), and 4-methyl­pyridine N-oxide (4MePNO). The compounds are bis­(μ-pyridine N-oxide)bis­[aqua­dibromido­(pyridine N-oxide)manganese(II)], [Mn2Br4(C5H5NO)4(H2O)2] (I), bis­(μ-2-methyl­pyridine N-oxide)bis­[di­aqua­dibromido­manganese(II)]–2-methyl­pyridine N-oxide (1/2), [Mn2Br4(C6H7NO)2(H2O)4]·2C6H7NO (II), bis­(μ-3-methyl­pyridine N-oxide)bis­[aqua­dibromido­(3-methyl­pyridine N-oxide)manganese(II)], [Mn2Br4(C6H7NO)4(H2O)2] (III), and bis­(μ-4-methyl­pyridine N-oxide)bis­[di­bromido­methanol(4-methyl­pyridine N-oxide)manganese(II)], [Mn2Br4(C6H7NO)4(CH3OH)2] (IV). All the compounds have one unique MnII atom and form a dimeric complex that contains two MnII atoms related by a crystallographic inversion center. Pseudo-octa­hedral six-coordinate manganese(II) centers are found in all four compounds. All four compounds form dimers of Mn atoms bridged by the oxygen atom of the PNO ligand. Compounds I, II and III exhibit a bound water of solvation, whereas compound IV contains a bound methanol mol­ecule of solvation. Compounds I, III and IV exhibit the same arrangement of mol­ecules around each manganese atom, ligated by two bromide ions, oxygen atoms of two PNO ligands and one solvent mol­ecule, whereas in compound II each manganese atom is ligated by two bromide ions, one O atom of a PNO ligand and two water mol­ecules with a second PNO mol­ecule inter­acting with the complex via hydrogen bonding through the bound water mol­ecules. All of the compounds form extended hydrogen-bonding networks, and compounds I, II, and IV exhibit offset π-stacking between PNO ligands of neighboring dimers.

A cadmium germanium arsenide compound, Cd3Ge2As4, was synthesized using a double-containment fused quartz ampoule method within a rocking furnace and a melt-quench technique. The crystal structure was determined from single-crystal X-ray diffraction (SC-XRD), scanning and transmission electron microscopies (i.e. SEM, STEM, and TEM), and selected area diffraction (SAD) and confirmed with electron backscatter diffraction (EBSD). The chemistry was verified with electron energy loss spectroscopy (EELS).

In the title di­thio­glycoluril derivative, C19H20N4O3S2, there is a difference in the torsion angles between the thio­imidazole moiety and the meth­oxy­phenyl groups on either side of the mol­ecule [C—N—Car—Car = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the di­thio­glycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H⋯S hydrogen bonds link adjacent mol­ecules to form chains propagating along the c-axis direction. The chains are linked by C—H⋯S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H⋯π inter­actions, leading to the formation of a three-dimensional supra­molecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the mol­ecular inter­actions in the crystal.

A new mononuclear NiII complex with bis­(pyridin-2-yl)amine (dpyam) and benzoate (benz), [Ni(C7H5O2)2(C10H9N3)], crystallizes in the monoclinic space group P21/c. The NiII ion adopts a cis-distorted octa­hedral geometry with an [NiN2O4] chromophore. In the crystal, the complex mol­ecules are linked together into a one-dimensional chain by symmetry-related π–π stacking inter­actions [centroid-to-centroid distance = 3.7257 (17) Å], along with N—H⋯O and C—H⋯O hydrogen bonds. The crystal packing is further stabilized by C—H⋯π inter­actions, which were investigated by Hirshfeld surface analysis.

Two compounds, 1,3-diethyl-5-{(2E,4E)-6-[(E)-1,3,3-tri­methyl­indolin-2-yl­idene]hexa-2,4-dien-1-yl­idene}pyrimidine-2,4,6(1H,3H,5H)-trione or TMI, C25H29N3O3, and 1,3-diethyl-2-sulfanyl­idene-5-[2-(1,3,3-tri­methyl­indolin-2-yl­idene)ethyl­idene]di­hydro­pyrimidine-4,6(1H,5H)-dione or DTB, C21H25N3O2S, have been crystallized and studied. These compounds contain the same indole derivative donor group and differ in their acceptor groups (in TMI it contains oxygen in the para position, and in DTB sulfur) and the length of the π-bridge. In both materials, mol­ecules are packed in a herringbone manner with differences in the twist and fold angles. In both structures, the mol­ecules are connected by weak C—H⋯O and/or C—H⋯S bonds.

Imidazolium salts are common building blocks for functional materials and in the synthesis of N-heterocyclic carbene (NHC) as σ-donor ligands for stable metal complexes. The title salt, 1,3-bis­(4-hy­droxy­phen­yl)-1H-imidazol-3-ium chloride (IOH·Cl), C15H13N2O2+·Cl−, is a new imidazolium salt with a hy­droxy functionality. The synthesis of IOH·Cl was achieved in high yield via a two-step procedure involving a di­aza­butadiene precursor followed by ring closure using tri­methylchloro­silane and paraformaldehyde. The structure of IOH·Cl consists of a central planar imidazolium ring (r.m.s. deviation = 0.0015 Å), with out-of-plane phenolic side arms. The dihedral angles between the 4-hy­droxy­phenyl substituents and the imidazole ring are 55.27 (7) and 48.85 (11)°. In the crystal, O—H⋯Cl hydrogen bonds connect the distal hy­droxy groups and Cl− anions in adjacent asymmetric units, one related by inversion (−x + 1, −y + 1, −z + 1) and one by the n-glide (x − {1over 2}, −y + {1over 2}, z − {1over 2}), with donor–acceptor distances of 2.977 (2) and 3.0130 (18) Å, respectively. The phenolic rings are each π–π stacked with their respective inversion-related [(−x + 1, −y + 1, −z + 1) and (−x, −y + 1, −z + 1)] counterparts, with inter­planar distances of 3.560 (3) and 3.778 (3) Å. The only other noteworthy inter­molecular inter­action is an O⋯O (not hydrogen bonded) close contact of 2.999 (3) Å between crystallographically different hy­droxy O atoms on translationally adjacent mol­ecules (x + 1, y, x + 1).

The title compound, C18H16N4O, consists of a 3,6-bis­(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl­oxy)meth­yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C—HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C—HPrp­oxy⋯π (Prp­oxy = prop-2-en-1-yl­oxy) inter­actions link the mol­ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter­actions being the dominant inter­actions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

The title compound, C4H12N+·C11H5N4−, contains one tetra­methyl­ammonium cation and one 1,1,7,7-tetra­cyano­hepta-2,4,6-trienide anion in the asymmetric unit. The anion is in an all-trans conjugated C=C bonds conformation. Two terminal C(CN)2 di­nitrile moieties are slightly twisted from the polymethine main chain to which they are attached [C(CN)2/C5 dihedral angles = 6.1 (2) and 7.1 (1)°]. The C—C bond distances along the hepta­dienyl chain vary in the narrow range 1.382 (2)–1.394 (2) Å, thus indicating the significant degree of conjugation. In the crystal, the anions are linked into zigzag chains along the [10overline{1}] direction by C—H⋯N(nitrile) short contacts. The anti­parallel chains stack along the [110] direction with alternating separations between the neighboring anions in stacks of 3.291 and 3.504 Å. The C—H⋯N short contacts and stacking inter­actions combine to link the anions into layers parallel to the (overline{1}01) plane and separated by columns of tetra­methyl­ammonium cations.

Reaction of 2-(anthracen-9-yl)phenol (HOPhAn, 1) with divalent Yb[N(SiMe3)2]2·2THF in THF–toluene mixtures affords the mixed-valence YbII–YbIII dimer {[2-(anthracen-9-yl)phenolato-κO]bis­(tetra­hydro­furan)­ytterbium(III)}-tris­[μ-2-(anthracen-9-yl)phenolato]-κ4O:O;κO:1,2-η,κO-{[2-(anthracen-9-yl)phenolato-κO]ytterbium(II)} toluene tris­olvate, [Yb2(C20H13O)5(C4H8O)2]·3C7H7 or [YbIII(THF)2(OPhAn)](μ-OPhAn)3[YbII(OPhAn)]·3C7H7 (2), as the major product. It crystallized as a toluene tris­olvate. The Yb—O bond lengths in the crystal structure of this dimer clearly identify the YbII and YbIII centres. Inter­estingly, the formally four-coordinate YbII centre shows a close contact with one anthracene C—C bond of a bridging OPhAn ligand, bringing the formal coordination number to five.

In this paper, we describe the synthesis of a new di­hydro-2H-pyridazin-3-one derivative. The mol­ecule, C18H16N2O, is not planar; the benzene and pyridazine rings are twisted with respect to each other, making a dihedral angle of 11.47 (2)°, and the toluene ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 89.624 (1)°. The mol­ecular conformation is stabilized by weak intra­molecular C—H⋯N contacts. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R22(8) ring motif. The inter­molecular inter­actions were investigated using Hirshfeld surface analysis and two-dimensional (2D) fingerprint plots, revealing that the most important contributions for the crystal packing are from H⋯H (56.6%), H⋯C/C⋯H (22.6%), O⋯H/H⋯O (10.0%) and N⋯C/C⋯N (3.5%) inter­actions.

The structure of the title complex, [Ag(C11H15N3S)2]PF6, has monoclinic (P21/c) symmetry, and the silver atom has a distorted square-planar geometry. The coordination complex crystallized from mixing silver hexa­fluorido­phosphate with a concentrated tetra­hydro­furan solution of N,N-di­ethyl­phenyl­azo­thio­formamide [ATF; systematic name: 3,3-diethyl-1-(phenyl­imino)­thio­urea] under ambient conditions. The resultant coordination complex exhibits a 2:1 ligand-to-metal ratio, with the silver(I) atom having a fourfold AgN2S2 coordination sphere, with a single PF6 counter-ion. In the crystal, however, one sulfur atom from an ATF ligand of a neighboring complex coordinates to the silver atom, with a bond distance of 2.9884 (14) Å. This creates a polymeric zigzag chain propagating along the c-axis direction. The chains are linked by C—H⋯F hydrogen bonds, forming slabs parallel to the ac plane.

The title salt, C10H21N2O+·C7H12NO4S−, comprises a 3-methacryl­amido-N,N,N-tri­methyl­propan-1-aminium cation and a 2-acryl­amido-2-methyl­propane-1-sulfonate anion. The salt crystallizes with two unique cation–anion pairs in the asymmetric unit of the ortho­rhom­bic unit cell. The crystal studied was an inversion twin with a 0.52 (4):0.48 (4) domain ratio. In the crystal, the cations and anions stack along the b-axis direction and are linked by an extensive series of N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network. Hirshfeld surface analysis was carried out on both the asymmetric unit and the two individual salts. The contribution of inter­atomic contacts to the surfaces of the individual cations and anions are also compared.

The crystal structures of the disordered hemi-DMSO solvate of (E)-2-oxo-N'-(3,4,5-tri­meth­oxy­benzyl­idene)-2H-chromene-3-carbohydrazide, C20H18N2O6·0.5C2H6OS, and (E)-N'-benzyl­idene-2-oxo-2H-chromene-3-carbohydrazide, C17H12N2O3 (4: R = C6H5), are discussed. The non-hydrogen atoms in compound [4: R = (3,4,5-MeO)3C6H2)] exhibit a distinct curvature, while those in compound, (4: R = C6H5), are essential coplanar. In (4: R = C6H5), C—H⋯O and π–π intra­molecular inter­actions combine to form a three-dimensional array. A three-dimensional array is also found for the hemi-DMSO solvate of [4: R = (3,4,5-MeO)3C6H2], in which the mol­ecules of coumarin are linked by C—H⋯O and C—H⋯π inter­actions, and form tubes into which the DMSO mol­ecules are cocooned. Hirshfeld surface analyses of both compounds are reported, as are the lattice energy and inter­molecular inter­action energy calculations of compound (4: R = C6H5).

The title Schiff base compound, C14H10Cl2N2O, features an E configuration about each of the C=N imine bonds. Overall, the mol­ecule is approximately planar with the dihedral angle between the central C2N2 residue (r.m.s. deviation = 0.0371 Å) and the peripheral hy­droxy­benzene and chloro­benzene rings being 4.9 (3) and 7.5 (3)°, respectively. Nevertheless, a small twist is evident about the central N—N bond [the C—N—N—C torsion angle = −172.7 (2)°]. An intra­molecular hy­droxy-O—H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, π–π stacking inter­actions between hy­droxy- and chloro­benzene rings [inter-centroid separation = 3.6939 (13) Å] lead to a helical supra­molecular chain propagating along the b-axis direction; the chains pack without directional inter­actions between them. The calculated Hirshfeld surfaces point to the importance of H⋯H and Cl⋯H/H⋯Cl contacts to the overall surface, each contributing approximately 29% of all contacts. However, of these only Cl⋯H contacts occur at separations less than the sum of the van der Waals radii. The aforementioned π–π stacking inter­actions contribute 12.0% to the overall surface contacts. The calculation of the inter­action energies in the crystal indicates significant contributions from the dispersion term.

In the title compound, C27H29BrN2, the carbazole ring system is essentially planar, with an r.m.s. deviation of 0.0781 (16) Å. An intra­molecular N—H⋯N hydrogen bond forms an S(6) ring motif. One of the tert-butyl substituents shows rotational disorder over two sites with occupancies of 0.592 (3) and 0.408 (3). In the crystal, two mol­ecules are associated into an inversion dimer through a pair of C—H⋯π inter­actions. The dimers are further linked by another pair of C—H⋯π inter­actions, forming a ribbon along the c-axis direction. A C—H⋯π inter­action involving the minor disordered component and the carbazole ring system links the ribbons, generating a network sheet parallel to (100).

The reaction of bis­(3-oxo-1,3-di­phenyl­prop-1-enolato-κ2O,O')zinc(II), [Zn(dbm)2], with tris­[4-(pyridin-3-yl)phen­yl]amine (T3PyA) in tetra­hydro­furan (THF) afforded the title crystalline coordination polymer, {[Zn(C15H11O2)2(C33H24N4)]·C4H8O}n. The asymmetric unit contains two independent halves of Zn(dbm)2, one T3PyA and one THF. Each ZnII atom is located on an inversion centre and adopts an elongated octa­hedral coordination geometry, ligated by four O atoms of two dbm ligands in equatorial positions and by two N atoms of pyridine moieties from two different bridging T3PyA ligands in axial positions. The crystal packing shows a one-dimensional polymer chain in which the two pyridyl groups of the T3PyA ligand bridge two independent Zn atoms of Zn(dbm)2. In the crystal, the coordination polymer chains are linked via C—H⋯π inter­actions into a sheet structure parallel to (010). The sheets are cross-linked via further C—H⋯π inter­actions into a three-dimensional network. The solvate THF mol­ecule shows disorder over two sets of atomic sites having occupancies of 0.631 (7) and 0.369 (7).

In the title compound, [Cd(NO3)2(C13H11N3)2], the CdII atom lies on a twofold rotation axis and is coordinated by four N atoms and two O atoms, provided by two bidentate 2-(1H-benzimidazol-2-yl)aniline ligands, and two nitrato O atoms, forming a distorted octa­hedral geometry [range of bond angles around the Cd atom = 73.82 (2)–106.95 (8)°]. In the ligand, the dihedral angle between the aniline ring and the benzimidazole ring system is 30.43 (7)°. The discrete complex mol­ecule is stabilized by an intra­molecular N—H⋯O hydrogen bond. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional network.

The title compound, [Ni(C64H33F10N5S2)]·xCH2Cl2, consists of discrete NiII porphyrin complexes, in which the five-coordinate NiII cations are in a distorted square-pyramidal coordination geometry. The four porphyrin nitro­gen atoms are located in the basal plane of the pyramid, whereas the pyridine N atom is in the apical position. The porphyrin plane is strongly distorted and the NiII cation is located above this plane by 0.241 (3) Å and shifted in the direction of the coordinating pyridine nitro­gen atom. The pyridine ring is not perpendicular to the N4 plane of the porphyrin moiety, as observed for related compounds. In the crystal, the complexes are linked via weak C—H⋯F hydrogen bonds into zigzag chains propagating in the [001] direction. Within this arrangement cavities are formed, in which highly disordered di­chloro­methane solvate mol­ecules are located. No reasonable structural model could be found to describe this disorder and therefore the contribution of the solvent to the electron density was removed using the SQUEEZE option in PLATON [Spek (2015). Acta Cryst. C71, 9–18].

In the title compound, C24H31N3O2, the mean plane of the central pyrazole ring [r.m.s. deviation = 0.095 Å] makes dihedral angles of 11.93 (9) and 84.53 (8)°, respectively, with the phenyl and benzene rings. There is a short intra­molecular N—H⋯N contact, which generates an S(5) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds link inversion-related mol­ecules into dimers, generating an R22(8) ring motif. The Hirshfeld surface analysis indicates that the most significant contribution involves H⋯H contacts of 68.6%

Single crystals of the title compound barium zinc copper, BaCu2.6Zn2.4, were obtained from a sample prepared by heating metal chips of Ba, Cu, and Zn in an Ar atmosphere up to 973 K, followed by slow cooling. Single-crystal X-ray structure analysis revealed that BaCu2.6Zn2.4 crystallizes in an ortho­rhom­bic cell [a = 12.9858 (3), b = 5.2162 (1), and c = 6.6804 (2) Å] with an α-SrZn5-type structure (space group Pnma). The three-dimensional framework consists of Cu and Zn atoms, with Ba atoms in the tunnels extending in the b-axis direction. Although the Ba atom is larger than the Sr atom, the cell volume of BaCu2.6Zn2.4 [452.507 (19) Å3] is smaller than that of α-SrZn5 [466.08 Å3]. This decrease in volume can be attributed to the partial substitution of Cu atoms by Zn atoms in the framework because the Cu—Zn and Cu—Cu bonds are shorter than the Zn—Zn bond. The increase in Ba—Zn inter­atomic distances from the Sr—Zn distances is cancelled out by the partial replacement of Zn with Cu atoms, which leads to shorter average Ba—Zn/Cu distances.

The PtII atom in the title complex, [Pt(C15H18N4O4S)(C2H6OS)], exists within a square-planar NS2O donor set provided by the N, S, O atoms of the di-anionic tridentate thio­semicarbazo ligand and a dimethyl sulfoxide S atom. The two chelate rings are coplanar, subtending a dihedral angle of 1.51 (7)°. The maximum deviation from an ideal square-planar geometry is seen in the five-membered chelate ring with an S—Pt—S bite angle of 96.45 (2)°. In the crystal, mol­ecules are linked via N—H⋯O, C—H⋯O, C—H⋯N and C—H⋯π inter­actions into two-dimensional networks lying parallel to the ab plane. The conformations of related cyclo­hexyl­hydrazine-1-carbo­thio­amide ligands are compared to that of the title compound.

In the title inorganic mol­ecular salt, (N2H5)2SiF6, the silicon atom at the centre of the slightly distorted SiF6 octa­hedron [range of Si—F distances = 1.6777 (4)–1.7101 (4) Å] lies on a crystallographic inversion centre. In the crystal, the ions are connected by N—H⋯N and N—H⋯F hydrogen bonds; the former link the cations into [010] chains and the latter (some of which are bifurcated or trifurcated) link the ions into a three-dimensional network. The two-dimensional fingerprint plots show that F⋯H/H⋯F inter­actions dominate the Hirshfeld surface (75.5%) followed by H⋯H (13.6%) and N⋯H/H⋯N (8.4%) whereas F⋯F (1.9%) and F⋯N/N⋯F (0.6%) have negligible percentages. The title compound is isostructural with its germanium-containing analogue.

In the title compound, C24H22N4O4, the four pyridine rings are tilted slightly with respect to each other. The dihedral angles between the inner and outer pyridine rings are 12.51 (8) and 9.67 (9)°, while that between inner pyridine rings is 20.10 (7)°. Within the mol­ecule, intra­molecular C—H⋯O and C—H⋯N contacts are observed. In the crystal, adjacent mol­ecules are linked by π–π stacking inter­actions between pyridine rings and weak C—H⋯π inter­actions between a methyl H atom and the centroid of a pyridine ring, forming a two-dimensional layer structure extending parallel to the ac plane. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (52.9%) and H⋯C/C⋯H (17.3%) contacts.

The bicyclic imidazo[1,2-a]pyridine core of the title compound, C19H19N3, is relatively planar with an r.m.s. deviation of 0.040 Å. The phenyl ring is inclined to the mean plane of the imidazo[1,2-a]pyridine unit by 18.2 (1)°. In the crystal, mol­ecules are linked by N—H⋯H hydrogen bonds, forming chains along the c-axis direction. The chains are linked by C—H⋯π inter­actions, forming slabs parallel to the ac plane. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal structure is dominated by H⋯H (54%) and C⋯H/H⋯C (35.6%) contacts. The crystal studied was refined as an inversion twin

The structures of three compounds of 3-chloro-2-nitro­benzoic acid with 5-nitro­quinoline, (I), 6-nitro­quinoline, (II), and 8-hy­droxy­quinoline, (III), have been determined at 190 K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base mol­ecules are held together by O—H⋯N and C—H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4−, an acid–base inter­action involving H-atom transfer occurs and the H atom is located at the N site of the base mol­ecule. In the crystal of (I), the hydrogen-bonded acid–base units are linked by C—H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C—H⋯O hydrogen bond, forming wide ribbons parallel to the (overline{1}03) plane. These ribbons are stacked via π–π inter­actions between the quinoline ring systems [centroid–centroid distances = 3.4935 (5)–3.7721 (6) Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid–base units are also linked into a tape structure along the b-axis direction via C—H⋯O hydrogen bonds. Inversion-related tapes are linked by further C—H⋯O hydrogen bonds to form wide ribbons parallel to the (overline{3}08) plane. The ribbons are linked by weak π–π inter­actions [centroid–centroid distances = 3.8016 (8)–3.9247 (9) Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N—H⋯O and O—H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π–π inter­actions [centroid–centroid distances = 3.8016 (8)–3.9247 (9) Å], and the mol­ecular chains are linked into layers parallel to the ab plane through these inter­actions.

The title compound, C18H18F2N2O3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the pyridine ring with respect to the benzene ring; these two rings are inclined to each other by 53.3 (2)° in mol­ecule A and by 72.9 (2)° in mol­ecule B. The 3-(cyclo­propyl­meth­oxy) side chain has an extended conformation in both mol­ecules. The two mol­ecules are linked by a pair of C—H⋯O hydrogen bonds and two C—H⋯π inter­actions, forming an A–B unit. In the crystal, this unit is linked by N—H⋯O hydrogen bonds, forming a zigzag –A–B–A–B– chain along [001]. The chains are linked by C—H⋯N and C—H⋯F hydrogen bonds to form layers parallel to the ac plane. Finally, the layers are linked by a third C—H⋯π inter­action, forming a three-dimensional structure. The major contributions to the Hirshfeld surface are those due to H⋯H contacts (39.7%), followed by F⋯H/H⋯F contacts (19.2%).

In the title polymeric complex, {[FePt(CN)4(H2O)2]·2C3H6O}n, the FeII cation has an octa­hedral [FeN4O2] geometry being coordinated by two water mol­ecules and four cyanide anions. The Pt cation is located on an inversion centre and has a square-planar coordination environment formed by four cyanide groups. The tetra­cyano­platinate anions bridge the FeII cations to form infinite two-dimensional layers that propagate in the bc plane. Two guest mol­ecules of acetone per FeII are located between the layers. These guest acetone mol­ecules inter­act with the coordinated water mol­ecules by O—H⋯O hydrogen bonds.

In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring of the meth­oxy­phenyl group. Two intra­molecular N—H⋯O and N—H⋯N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with R22(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C—H⋯π and π–π-stacking inter­actions [centroid-to-centroid distances = 3.631 (2) and 3.631 (2) Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H⋯H (39.3%), C⋯H/H⋯C (18.0%), O⋯H/H⋯O (15.6) and S⋯H/H⋯S (10.2%) inter­actions.

Amino­pyridine and phthalic acid are well known synthons for supra­molecular architectures for the synthesis of new materials for optical applications. The 2-amino­pyridinium hydrogen phthalate title salt, C5H7N2+·C8H5O4−, crystallizes in the non-centrosymmetric space group P21. The nitro­gen atom of the –NH2 group in the cation deviates from the fitted pyridine plane by 0.035 (7) Å. The plane of the pyridinium ring and phenyl ring of the anion are oriented at an angle of 80.5 (3)° to each other in the asymmetric unit. The anion features a strong intra­molecular O—H⋯O hydrogen bond, forming a self-associated S(7) ring motif. The crystal packing is dominated by inter­molecular N—H⋯O hydrogen bonds leading to the formation of 21 helices, with a C(11) chain motif. They propagate along the b axis and enclose R22(8) ring motifs. The helices are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ab plane. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate and qu­antify the inter­molecular inter­actions in the crystal.

The title phospho­nate-based organic–inorganic hybrid framework, poly[bis(dimethylammonium) [(μ4-2,5-dihydroxybenzene-1,4-diphosphonato)zinc(II)]], {(C2H8N)2[Zn(C6H4O8P2)]}n, was formed unexpectedly when di­methyl­ammonium cations were formed from the in situ deca­rbonylation of the N,N-di­methyl­formamide solvent. The framework is built up from ZnO4 tetra­hedra and bridging di­phospho­nate tetra-anions to generate a three-dimensional network comprising [100] channels occupied by the (CH3)2NH2+ cations. Within the channels, an array of N—H⋯O hydrogen bonds help to establish the structure. In addition, intra­molecular O—H⋯O hydrogen bonds between the appended –OH groups of the phenyl ring and adjacent PO32− groups are observed.

In the cation of the title salt, C9H12N3S+·Br−, the thia­zolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N—H⋯Br hydrogen bonds link the components into a three-dimensional network. Weak π–π stacking inter­actions between the phenyl rings of adjacent cations also contribute to the mol­ecular packing. A Hirshfeld surface analysis was conducted to qu­antify the contributions of the different inter­molecular inter­actions and contacts.