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The title compound, (C9H8N)2[MnBr4], consists of two quinolinium cations and a [MnBr4]2− anion. The manganese(II) atom, which lies on a twofold rotation axis, is coordinated by four bromide ligands and exhibits a tetra­hedral coordination geometry. The [MnBr4]2− anion and the quinolinium cations are linked by N—H⋯Br hydrogen bonds. π–π stacking inter­actions are observed between the quinolinium cations.

The title compound, {(C9H11N2)[Mn(NCS)3]}n, has been obtained as a side product of the salt metathesis reaction of 1-ethyl-3-methyl­imidazolium bromide, (EMIm)Br, and K2[Mn(NCS)4]. The structure consists of discrete 1-ethyl-3-methyl­imidazolium cations and an anionic two-dimensional network of manganese(II)-based complex anions, inter­connected by thio­cyanate ions. Every Mn2+ ion is coordinated by three S atoms of three NCS− ions and three N atoms of further three NCS− ions in a meridional octa­hedral fashion.

The title compound, (C15H23N2)2[MnBr4], comprises two N-adamantyl-N'-ethyl­imidazolium cations and one tetra­hedral [MnBr4]2− anion. Next to Coulombic inter­actions, weak hydrogen bonds of the type C—H⋯Br consolidate the crystal packing, building up a three-dimensional network.

In the title compound, C61H15ClN2O3, the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-di­meth­oxy­phenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links mol­ecules related by a 41 screw axis to form a C(6) chain, and the other links inversion-related pairs of mol­ecules to form an R22(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.

The title compound, hexa­kis­(2-methyl-1H-imidazol-3-ium) hepta­molybdate 2-methyl-1H-imidazole disolvate dihydrate, (C4H7N2)6[Mo7O24]·2C4H6N2·2H2O, was prepared from 2-methyl­imidazole and ammonium hepta­molybdate tetra­hydrate in acid solution. The [Mo7O24]6− hepta­molybdate cluster anion is accompanied by six protonated (C4H7N2)+ 2-methyl­imidazolium cations, two neutral C4H6N2 2-methyl­imidazole mol­ecules and two water mol­ecules of crystallization. The cluster consists of seven distorted MoO6 octa­hedra sharing edges or vertices. In the crystal, the components are linked by N—H⋯N, N—H⋯O, O—H⋯O, N—H⋯(O,O) and O—H⋯(O,O) hydrogen bonds, generating a three-dimensional network. Weak C—H⋯O inter­actions consolidate the packing.

Phenanthroline ligands are important metal-binding mol­ecules which have been extensively researched for applications in both material science and medicinal chemistry. Azo­benzene and its derivatives have received significant attention because of their ability to be reversibly switched between the E and Z forms and so could have applications in optical memory and logic devices or as mol­ecular machines. Herein we report the formation and crystal structure of a highly unusual novel diazo-diphenanthroline compound, C24H14N6O2·2CHCl3.

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.

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.

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.

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.

Twelve 4-(4-meth­oxy­phen­yl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. The monohydrated benzoate, 4-fluoro­benzoate, 4-chloro­benzoate and 4-bromo­benzoate salts, C11H17N2O+·C7H5O2−·H2O (I), C11H17N2O+·C7H4FO2−·H2O (II), C11H17N2O+·C7H4ClO2−·H2O (III), and C11H17N2O+·C7H4BrO2−·H2O (IV), respectively, are isomorphous and all exhibit disorder in the 4-meth­oxy­phenyl unit: the components are linked by N—H⋯O and O—H⋯O hydrogen bond to form chains of rings. The unsolvated 2-hy­droxy­benzoate, pyridine-3-carboxyl­ate and 2-hy­droxy-3,5-di­nitro­benzoate salts, C11H17N2O+·C7H5O3− (V), C11H17N2O+·C6H4NO2− (VI) and C11H17N2O+·C7H3N2O7− (VII), respectively, are all fully ordered: the components of (V) are linked by multiple N—H⋯O hydrogen bonds to form a chain of rings; those of (VI) are linked into a three-dimensional framework by a combination of N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds and those of (VII), where the anion has a structure reminiscent of the picrate anion, are linked into a three-dimensional array by N—H⋯O and C—H⋯O hydrogen bonds. The hydrogensuccinate and hydrogenfumarate salts, C11H17N2O+·C4H5O4− (VIII) and C11H17N2O+·C4H3O3− (IX), respectively, are isomorphous, and both exhibit disorder in the anionic component: N—H⋯O and O—H⋯O hydrogen bonds link the ions into sheets, which are further linked by C—H⋯π(arene) inter­actions. The anion of the hydrogenmaleate salt, C11H17N2O+·C4H3O3− (X), contains a very short and nearly symmetrical O⋯H⋯O hydrogen bond, and N—H⋯O hydrogen bonds link the anions into chains of rings. The ions in the tri­chloro­acetate salt, C11H17N2O+·C2Cl3O2− (XI), are linked into simple chains by N—H⋯O hydrogen bonds. In the hydrated chloranilate salt, 2C11H17N2O+·C6Cl2O42−·2H2O (XII), which crystallizes as a non-merohedral twin, the anion lies across a centre of inversion in space group P21/n, and a combination of N—H⋯O and O—H⋯O hydrogen bonds generates complex sheets. Comparisons are made with the structures of some related compounds.

The asymmetric unit of the title com­pound, catena-poly[[[(perchlorato-κO)copper(II)]-μ-3-(3-carb­oxy­prop­yl)-1,5,8,12-tetra­aza-3-azonia­cyclo­tetra­decane-κ4N1,N5,N8,N12] bis­(per­chlorate)], {[Cu(C13H30N5O2)(ClO4)](ClO4)2}n, (I), consists of a macrocyclic cation, one coordinated per­chlorate anion and two per­chlorate ions as counter-anions. The metal ion is coordinated in a tetra­gonally distorted octa­hedral geometry by the four secondary N atoms of the macrocyclic ligand, the mutually trans O atoms of the per­chlorate anion and the carbonyl O atom of the protonated carb­oxy­lic acid group of a neighbouring cation. The average equatorial Cu—N bond lengths [2.01 (6) Å] are significantly shorter than the axial Cu—O bond lengths [2.379 (8) Å for carboxyl­ate and average 2.62 (7) Å for disordered per­chlorate]. The coordinated macrocyclic ligand in (I) adopts the most energetically favourable trans-III conformation with an equatorial orientation of the substituent at the protonated distal 3-position N atom in a six-membered chelate ring. The coordination of the carb­oxy­lic acid group of the cation to a neighbouring com­plex unit results in the formation of infinite chains running along the b-axis direction, which are cross­linked by N—H⋯O hydrogen bonds between the secondary amine groups of the macrocycle and O atoms of the per­chlorate counter-anions to form sheets lying parallel to the (001) plane. Additionally, the extended structure of (I) is consolidated by numerous intra- and interchain C—H⋯O contacts.

The non-porous three-dimensional structure of poly[(μ5-2-amino­benzene-1,4-di­carboxyl­ato)(μ6-oxalato)(oxomium)europium(III)], [Eu(C8H5NO4)(C2O4)(H3O)]n or [EuIII(NH2–BDC)(ox)(H3O)]n (NH2–BDC2− = 2-amino­terephthalate and ox2− = oxalate) is constructed from two-dimensional layers of EuIII–carboxyl­ate–oxalate, which are connected by NH2–BDC2− pillars. The basic structural unit of the layer is an edge-sharing dimer of TPRS-{EuIIIO9}, which is assembled through the ox2− moiety. The intra­layer void is partially occupied by TPR-{EuIIIO6} motifs. Weak C—H⋯O and strong, classical intra­molecular N—H⋯O and inter­molecular O—H⋯O hydrogen-bonding inter­actions, as well as weak π–π stacking inter­actions, affix the organic pillars within the framework. The two-dimensional layer can be simplified to a uninodal 4-connected sql/Shubnikov tetra­gonal plane net with point symbol {44.62}.

In the title compound, (2,2'-bi­pyridine-κ2N,N')bis­(2-meth­oxy­ethyl xanthato-κS)zinc(II), [Zn(C4H7O2S2)2(C10H8N2)], the ZnII ion is coordinated to two N atoms of the 2,2'-bi­pyridine ligand and two S atoms from two 2-meth­oxy­ethyl xanthate ligands. The ZnII ion lies on a crystallographic twofold rotation axis and has distorted tetra­hedral coordination geometry. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming supramolecular chains propagating along the a-axis direction. Weak intra­molecular C—H⋯S hydrogen bonds are also observed. The inter­molecular contacts in the crystal were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H⋯H (36.3%), followed by S⋯H/H⋯S (24.7%), C⋯H/H⋯C (15.1%), O⋯H/H⋯O (14.4%), N⋯H/H⋯N (4.1%) and C⋯C (2.9%).

The asymmetric unit of the title compound, {[Mn2Sb2S5(C15H11N3)2]·4H2O}n, consists of two crystallographically independent MnII ions, two unique terpyridine ligands, one [Sb2S5]4− anion and four solvent water mol­ecules, all of which are located in general positions. The [Sb2S5]4− anion consists of two SbS3 units that share common corners. Each of the MnII ions is fivefold coordinated by two symmetry-related S atoms of [Sb2S5]4− anions and three N atoms of a terpyridine ligand within an irregular coordination. Each two anions are linked by two [Mn(terpyridine)]2+ cations into chains along the c-axis direction that consist of eight-membered Mn2Sb2S4 rings. These chains are further connected into a three-dimensional network by inter­molecular O—H⋯O and O—H⋯S hydrogen bonds. The crystal investigated was twinned and therefore, a twin refinement using data in HKLF-5 [Sheldrick (2015). Acta Cryst. C71, 3–8] format was performed.

The complete mol­ecule of the binuclear title complex, bis­[μ-1H-1,2,4-triazole-5(4H)-thione-κ2S:S]bis­{(thio­cyanato-κS)[1H-1,2,4-triazole-5(4H)-thione-κS]silver(I)}, [Ag2(SCN)2(C2H3N3S)4], is generated by crystallographic inversion symmetry. The independent triazole-3-thione ligands employ the exocyclic-S atoms exclusively in coordination. One acts as a terminal S-ligand and the other in a bidentate (μ2) bridging mode to provide a link between two AgI centres. Each AgI atom is also coordinated by a terminal S-bound thio­cyanate ligand, resulting in a distorted AgS4 tetra­hedral coordination geometry. An intra­molecular N—H⋯S(thio­cyanate) hydrogen bond is noted. In the crystal, amine-N—H⋯S(thione), N—H⋯N(triazol­yl) and N—H⋯N(thio­cyanate) hydrogen bonds give rise to a three-dimensional architecture. The packing is consolidated by triazolyl-C—H⋯S(thio­cyanate), triazolyl-C—H⋯N(thiocyanate) and S⋯S [3.2463 (9) Å] inter­actions as well as face-to-face π–π stacking between the independent triazolyl rings [inter-centroid separation = 3.4444 (15) Å]. An analysis of the calculated Hirshfeld surfaces shows the three major contributors are due to N⋯H/H⋯N, S⋯H/H⋯S and C⋯H/H⋯C contacts, at 35.8, 19.4 and 12.7%, respectively; H⋯H contacts contribute only 7.6% to the overall surface.

Two new mononuclear metal complexes involving the bidentate Schiff base ligand 2,4,6-trimethyl-N-[(pyridin-2-yl)methyl­idene]aniline (C15H16N2 or PM-TMA), [Mn(NCS)2(PM-TMA)2] (I) and [Ni(NCS)2(PM-TMA)2] (II), were synthesized and their structures determined by single-crystal X-ray diffraction. Although the title compounds crystallize in different crystal systems [triclinic for (I) and monoclinic for (II)], both asymmetric units consist of one-half of the complex mol­ecule, i.e. one metal(II) cation, one PM-TMA ligand, and one N-bound thio­cyanate anion. In both complexes, the metal(II) cation is located on a centre of inversion and adopts a distorted octa­hedral coordination environment defined by four N atoms from two symmetry-related PM-TMA ligands in the equatorial plane and two N atoms from two symmetry-related NCS− anions in a trans axial arrangement. The tri­methyl­benzene and pyridine rings of the PM-TMA ligand are oriented at dihedral angles of 74.18 (7) and 77.70 (12)° for (I) and (II), respectively. The subtle change in size of the central metal cations leads to a different crystal packing arrangement for (I) and (II) that is dominated by weak C—H⋯S, C—H⋯π, and π–π inter­actions. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to qu­antify these inter­molecular contacts, and indicate that the most significant contacts in packing are H⋯H [48.1% for (I) and 54.9% for (II)], followed by H⋯C/C⋯H [24.1% for (I) and 15.7% for (II)], and H⋯S/S⋯H [21.1% for (I) and 21.1% for (II)].

The title compound, di­aqua­[tris­(2-amino­eth­yl)amine]­nickel(II) hexa­aqua­nickel(II) bis­(sulfate), [Ni(C6H18N4)(H2O)2][Ni(H2O)6](SO4)2 or [Ni(tren)(H2O)2][Ni(H2O)6](SO4)2, consists of two octa­hedral nickel complexes within the same unit cell. These metal complexes are formed from the reaction of [Ni(H2O)6](SO4) and the ligand tris­(2-amino­eth­yl)amine (tren). The crystals of the title compound are purple, different from those of the starting complex [Ni(H2O)6](SO4), which are turquoise. The reaction was performed both in a 1:1 and 1:2 metal–ligand molar ratio, always yielding the co-precipitation of the two types of crystals. The asymmetric unit of the title compound, which crystallizes in the space group Pnma, consists of two half NiII complexes and a sulfate counter-anion. The mononuclear cationic complex [Ni(tren)(H2O)2]2+ comprises an Ni ion, the tren ligand and two water mol­ecules, while the mononuclear complex [Ni(H2O)6]2+ consists of another Ni ion surrounded by six coordinated water mol­ecules. The [Ni(tren)(H2O)2] and [Ni(H2O)6] subunits are connected to the SO42− counter-anions through hydrogen bonding, thus consolidating the crystal structure.

The whole mol­ecule of the cadmium(II) complex, di­iodido­{N,N',N'',N'''-[pyrazine-2,3,5,6-tetra­yltetra­kis­(methyl­ene)]tetra­kis­(N-methyl­aniline)-κ3N2,N1,N6}cadmium(II), [CdI2(C36H40N6)], (I), of the ligand N,N',N'',N'''-[pyrazine-2,3,5,6-tetra­yltetra­kis­(methyl­ene)]tetra­kis­(N-methyl­aniline) (L), is generated by a twofold rotation symmetry; the twofold axis bis­ects the cadmium atom and the nitro­gen atoms of the pyrazine ring. The ligand coordinates in a mono-tridentate manner and the cadmium atom has a fivefold CdN3I2 coordination environment with a distorted shape. In the zinc(II) complex, dichlorido{N,N',N'',N'''-[pyrazine-2,3,5,6-tetra­yltetra­kis­(methyl­ene)]tetra­kis­(N-methyl­aniline)-κ3N2,N1,N6}zinc(II) di­chloro­methane 0.6-solvate, [ZnCl2(C36H40N6)]·0.6CH2Cl2, (II), ligand L also coordinates in a mono-tridentate manner and the zinc atom has a fivefold ZnN3Cl2 coordination environment with a distorted shape. It crystallized as a partial di­chloro­methane solvate. In the crystal of I, the complex mol­ecules are linked by weak C—H⋯I contacts, forming ribbons propagating along [100]. In the crystal of II, the complex mol­ecules are linked by a series of C—H⋯π inter­actions, forming layers lying parallel to the (1overline{1}1) plane. In the crystals of both compounds there are metal–halide⋯π(pyrazine) contacts present. The Hirshfeld analyses confirm the importance of the C—H⋯halide contacts in the crystal packing of both compounds.

The crystal structures of tris­[9,9-dihexyl-2-(5-meth­oxy­pyridin-2-yl-κN)-9H-fluoren-3-yl-κC3]iridium pentane monosolvate, [Ir(C31H38NO)3]·C5H12, (I), di-μ2-chlorido-bis­{bis­[2-(5-fluoro­pyridin-2-yl)-9,9-dihexyl-9H-fluoren-3-yl]iridium} pentane 0.3-solvate, [Ir2(C30H35FN)4Cl2]·0.3C5H12, (II), di-μ2-cyanato-bis­{bis­[9,9-dihexyl-2-(5-meth­oxy­pyridin-2-yl)-9H-fluoren-1-yl]iridium} pentane monosolvate, [Ir2(C31H38NO)4(NCO)2(NCO)2]·C5H12, (III), and {μ-N,N'-bis­[3,5-bis­(tri­fluoro­meth­yl)phen­yl]oxamidato}bis(bis{2-[4-(2,4,6-trimethylphenyl)pyridin-2-yl]phenyl-κ2C1,N'}iridium)–chloro­benzene–pentane (1/2.3/0.4), [Ir2(C20H19N)4(C18H6F12N2O2)]·2.3C6H5Cl·0.4C5H12, (IV), synthesized in the quest for organic light-emitting devices, were determined. The bis-μ2-chloro and bis-μ2-cyanato complexes have ΔΔ and ΛΛ configurations of the distorted octa­hedral Ir centres in racemic crystals, whereas the oxamido complex has a centrosymmetric (meso) structure with the ΔΛ configuration. The bridging oxamido moiety has a nearly planar anti geometry. All structures show substantial disorder of both host mol­ecules and solvents of crystallization.