Optical properties of (Z)‐2‐(2‐phenylhydrazinylidene)acenaphthen‐1(2H)‐one: a potential electron donor in organic solar cells

Electron‐donating molecules play an important role in the development of organic solar cells. (Z )‐2‐(2‐Phenylhydrazinylidene)acenaphthen‐1(2H )‐one (PDAK), C₁₈H₁₂N₂O, was synthesized by a Schiff base reaction. The crystal structure shows that the molecules are planar and are linked together forming `face‐to‐face' assemblies held together by intermolecular C—H…O, π–π and C—H…π interactions. PDAK exhibits a broadband UV–Vis absorption (200–648 nm) and a low HOMO–LUMO energy gap (1.91 eV; HOMO is the highest occupied molecular orbital and LUMO is the lowest unoccupied molecular orbital), while fluorescence quenching experiments provide evidence for electron transfer from the excited state of PDAK to C₆₀. This suggests that the title molecule may be a suitable donor for use in organic solar cells.     

Supramolecular hydrogen‐bonding patterns in the organic–inorganic hybrid compound bis(4‐amino‐5‐chloro‐2,6‐dimethylpyrimidinium) tetrathiocyanatozinc(II)–4‐amino‐5‐chloro‐2,6‐dimethylpyrimidine–water (1/2/2)

Zinc thiocyanate complexes have been found to be biologically active compounds. Zinc is also an essential element for the normal function of most organisms and is the main constituent in a number of metalloenzyme proteins. Pyrimidine and aminopyrimidine derivatives are biologically very important as they are components of nucleic acids. Thiocyanate ions can bridge metal ions by employing both their N and S atoms for coordination. They can play an important role in assembling different coordination structures and yield an interesting variety of one‐, two‐ and three‐dimensional polymeric metal–thiocyanate supramolecular frameworks. The structure of a new zinc thiocyanate–aminopyrimidine organic–inorganic compound, (C₆H₉ClN₃)₂[Zn(NCS)₄]·2C₆H₈ClN₃·2H₂O, is reported. The asymmetric unit consist of half a tetrathiocyanatozinc(II) dianion, an uncoordinated 4‐amino‐5‐chloro‐2,6‐dimethylpyrimidinium cation, a 4‐amino‐5‐chloro‐2,6‐dimethylpyrimidine molecule and a water molecule. The Zn^II atom adopts a distorted tetrahedral coordination geometry and is coordinated by four N atoms from the thiocyanate anions. The Zn^II atom is located on a special position (twofold axis of symmetry). The pyrimidinium cation and the pyrimidine molecule are not coordinated to the Zn^II atom, but are hydrogen bonded to the uncoordinated water molecules and the metal‐coordinated thiocyanate ligands. The pyrimidine molecules and pyrimidinium cations also form base‐pair‐like structures with an R₂²(8) ring motif via N—H…N hydrogen bonds. The crystal structure is further stabilized by intermolecular N—H…O, O—H…S, N—H…S and O—H…N hydrogen bonds, by intramolecular N—H…Cl and C—H…Cl hydrogen bonds, and also by π–π stacking interactions.     

2‐Ethyl‐1‐[5‐(4‐methylphenyl)pyrazol‐3‐yl]‐3‐(thiophene‐2‐carbonyl)isothiourea: molecular ribbons containing three types of hydrogen‐bonded ring

The title compound, C₁₈H₁₈N₄OS₂, was prepared by reaction of S,S‐diethyl 2‐thenoylimidodithiocarbonate with 5‐amino‐3‐(4‐methylphenyl)‐1H‐pyrazole using microwave irradiation under solvent‐free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H...O hydrogen bond is present, forming an S(6) motif, and molecules are linked by N—H...O and N—H...N hydrogen bonds to form a ribbon in which centrosymmetric R₂²(4) rings, built from N—H...O hydrogen bonds and flanked by inversion‐related pairs of S(6) rings, alternate with centrosymmetric R₂²(6) rings built from N—H...N hydrogen bonds.     

Experimental and Theoretical Studies of 4‐(1‐benzyl‐5‐methyl‐1H‐1,2,3‐triazol‐4‐yl)‐6‐(2,4‐dichlorophenyl)pyrimidin‐2‐amine: A Potential Antibacterial Agent

The title compound ( 1 ), 4‐(1‐benzyl‐5‐methyl‐1H‐1,2,3‐triazol‐4‐yl)‐6‐(2,4‐dichlorophenyl)pyrimidin‐2‐amine (C₂₀H₁₆Cl₂N₆), was synthesized and structurally characterized by elemental analysis, ¹H NMR and ¹³C NMR and single crystal X‐ray diffraction. The compound crystallizes as a colourless needle shaped in the triclinic system, space group P‐1 with cell constants: a = 10.7557(11) Å, b = 12.7078(17) Å, c = 15.511(2) Å, α = 68.029(4)0, β = 86.637(5)0, γ = 87.869(4)0; V = 1962.4 (4) ų, Z = 4. There are two structurally similar but crystallographically independent molecules (A and B) in the asymmetric unit of the title compound, which is linked via N‐H…Cl hydrogen bond. An intramolecular C‐H…N hydrogen also occurs in each molecule. In the crystal, each of independent molecules forms a centrosymmetric dimer with an R²₂(8) ring motifs through a pair of N‐H…N hydrogen bonds. These dimers are further connected by intermolecular N‐H…Cl and C‐H…Cl hydrogen bonds, forming an infinite two dimensional supramolecular network lying parallel to the [010] plane. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6‐311G (d, p) basis set and compared with the experimental data. Mulliken population analyses on atomic charges, HOMO‐LUMO energy levels, Molecular electrostatic potential and chemical reactivity of the title compound were investigated by theoretical calculations. The thermo dynamical properties of the title compound at different temperature have been calculated and corresponding relations between the properties and temperature have also been obtained. The in vitro antibacterial activity has been screened against Gram‐positive (Bacillus cerus and Staphylococcus epidermidis) and Gram‐Negative (Escherichia coli, Acinetobacter baumannii and Proteus vulgaris). The results revealed that the compound exhibited good to moderate antibacterial activity.     

Crystallographic study of self‐organization in the solid state including quasi‐aromatic pseudo‐ring stacking interactions in 1‐benzoyl‐3‐(3,4‐dimethoxyphenyl)thiourea and 1‐benzoyl‐3‐(2‐hydroxypropyl)thiourea

1‐Benzoylthioureas contain both carbonyl and thiocarbonyl functional groups and are of interest for their biological activity, metal coordination ability and involvement in hydrogen‐bond formation. Two novel 1‐benzoylthiourea derivatives, namely 1‐benzoyl‐3‐(3,4‐dimethoxyphenyl)thiourea, C₁₆H₁₆N₂O₃S, (I), and 1‐benzoyl‐3‐(2‐hydroxypropyl)thiourea, C₁₁H₁₄N₂O₂S, (II), have been synthesized and characterized. Compound (I) crystallizes in the space group P , while (II) crystallizes in the space group P 2₁/c . In both structures, intramolecular N—H…O hydrogen bonding is present. The resulting six‐membered pseudo‐rings are quasi‐aromatic and, in each case, interact with phenyl rings via stacking‐type interactions. C—H…O, C—H…S and C—H…π interactions are also present. In (I), there is one molecule in the asymmetric unit. Pairs of molecules are connected via two intermolecular N—H…S hydrogen bonds, forming centrosymmetric dimers. In (II), there are two symmetry‐independent molecules that differ mainly in the relative orientations of the phenyl rings with respect to the thiourea cores. Additional strong hydrogen‐bond donor and acceptor –OH groups participate in the formation of intermolecular N—H…O and O—H…S hydrogen bonds that join molecules into chains extending in the [001] direction.     

Two single‐enantiomer amidophosphoesters: a database study on the chirality of (O)2P(O)(N)‐based structures

The crystal structures of two single‐enantiomer amidophosphoesters with an (O)₂P(O)(N) skeleton, i.e. diphenyl [(R)‐(+)‐α‐methylbenzylamido]phosphate, (I), and diphenyl [(S)‐(?)‐α‐methylbenzylamido]phosphate, (II), both C₂₀H₂₀NO₃P, are reported. In both structures, chiral one‐dimensional hydrogen‐bonded architectures, along [010], are mediated by N—H…OP interactions. The statistically identical assemblies include the noncentrosymmetric graph‐set motif C(4) and the compounds crystallize in the chiral space group P2₁. As a result of synergistic co‐operation from C—H…O interactions, a two‐dimensional superstructure is built including a noncentrosymmetric R₄⁴(22) hydrogen‐bonded motif. A Cambridge Structural Database survey was performed on (O)₂P(O)(N)‐based structures in order to review the frequency of space groups observed in this family of compounds; the hydrogen‐bond motifs in structures with chiral space groups and the types of groups inducing chirality are discussed. The ^2,3J_X–P (X = H or C) coupling constants from the NMR spectra of (I) and (II) have been studied. In each compound, the two diastereotopic C₆H₅O groups are different, which is reflected in the different chemical shifts and some coupling constants.     

2,2′‐[(Disulfanediyl)bis{5‐[(1E)‐(2‐hydroxybenzylidene)amino]‐1,3‐thiazole‐4,2‐diyl}]diphenol: synthesis,crystal structure and calculation of molecular hyperpolarizability

The title Schiff base compound {systematic name: 2‐[5‐[(E )‐(2‐hydroxybenzylidene)amino]‐4‐(2‐{5‐[(E )‐(2‐hydroxybenzylidene)amino]‐2‐(2‐hydroxyphenyl)‐1,3‐thiazol‐4‐yl}disulfanyl)‐1,3‐thiazol‐2‐yl]phenol}, C₃₂H₂₂N₄O₄S₄, incorporating a disulfanediyl (dithio) linkage, was obtained from the condensation reaction between two equivalents of salicylaldehyde and one equivalent of dithiooxamide in dimethylformamide, and was characterized by elemental analysis, IR spectroscopic analysis and single‐crystal X‐ray diffraction. A one‐dimensional chain is formed along the b axis via double intermolecular C—H…S hydrogen bonds. The HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energies and some related molecular parameters were calculated at the B3LYP/6‐311G(d,p) level of theory. The molecular hyperpolarizability was also calculated.     

Reactions between arylhydrazinium chlorides and 2‐chloroquinoline‐3‐carbaldehydes: molecular and supramolecular structures of a hydrazone,a 4,9‐dihydro‐1H‐pyrazolo[3,4‐b]quinoline and two 1H‐pyrazolo[3,4‐b]quinolines

Hydrazone derivatives exhibit a wide range of biological activities, while pyrazolo[3,4‐b]quinoline derivatives, on the other hand, exhibit both antimicrobial and antiviral activity, so that all new derivatives in these chemical classes are potentially of value. Dry grinding of a mixture of 2‐chloroquinoline‐3‐carbaldehyde and 4‐methylphenylhydrazinium chloride gives (E)‐1‐[(2‐chloroquinolin‐3‐yl)methylidene]‐2‐(4‐methylphenyl)hydrazine, C₁₇H₁₄ClN₃, (I), while the same regents in methanol in the presence of sodium cyanoborohydride give 1‐(4‐methylphenyl)‐4,9‐dihydro‐1H‐pyrazolo[3,4‐b]quinoline, C₁₇H₁₅N₃, (II). The reactions between phenylhydrazinium chloride and either 2‐chloroquinoline‐3‐carbaldehyde or 2‐chloro‐6‐methylquinoline‐3‐carbaldehyde give, respectively, 1‐phenyl‐1H‐pyrazolo[3,4‐b]quinoline, C₁₆H₁₁N₃, (III), which crystallizes in the space group Pbcn as a nonmerohedral twin having Z′ = 3, or 6‐methyl‐1‐phenyl‐1H‐pyrazolo[3,4‐b]quinoline, C₁₇H₁₃N₃, (IV), which crystallizes in the space group R. The molecules of compound (I) are linked into sheets by a combination of N—H…N and C—H…π(arene) hydrogen bonds, and the molecules of compound (II) are linked by a combination of N—H…N and C—H…π(arene) hydrogen bonds to form a chain of rings. In the structure of compound (III), one of the three independent molecules forms chains generated by C—H…π(arene) hydrogen bonds, with a second type of molecule linked to the chains by a second C—H…π(arene) hydrogen bond and the third type of molecule linked to the chain by multiple π–π stacking interactions. A single C—H…π(arene) hydrogen bond links the molecules of compound (IV) into cyclic centrosymmetric hexamers having (S₆) symmetry, which are themselves linked into a three‐dimensional array by π–π stacking interactions.     

Sulfonate salts of the therapeutic agent dapsone: 4‐[(4‐aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and 4‐[(4‐aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate

Dapsone, formerly used to treat leprosy, now has wider therapeutic applications. As is the case for many therapeutic agents, low aqueous solubility and high toxicity are the main problems associated with its use. Derivatization of its amino groups has been widely explored but shows no significant therapeutic improvements. Cocrystals have been prepared to understand not only its structural properties, but also its solubility and dissolution rate. Few salts of dapsone have been described. The title salts, C₁₂H₁₃N₂O₂S⁺·C₆H₅O₃S⁻·H₂O and C₁₂H₁₃N₂O₂S⁺·CH₃SO₃⁻·H₂O, crystallize as hydrates and both compounds exhibit the same space group (monoclinic, P2₁/n). The asymmetric unit of each salt consists of a 4‐[(4‐aminophenyl)sulfonyl]anilinium monocation, the corresponding sulfonate anion and a water molecule. The cation, anion and water molecule form hydrogen‐bonded networks through N—H…O=S, N—H…O_water and O_water—H…O=S hydrogen bonds. For both salts, the water molecules interact with one sulfonate anion and two anilinium cations. The benzenesulfonate salt forms a two‐dimensional network, while the hydrogen bonding within the methanesulfonate salt results in a three‐dimensional network.     

Side‐chain conformations in the isomorphous polyfluorinated {4,4′‐bis[(2,2‐difluoroethoxy)methyl]‐2,2′‐bipyridine‐κ2N,N′}dichloridopalladium and ‐platinum complexes

The polyfluorinated title compounds, [M Cl₂(C₁₆H₁₆F₄N₂O₂)] or [4,4′‐(HCF₂CH₂OCH₂)₂‐2,2′‐bpy]M Cl₂ [M = Pd, ( 1 ), and M = Pt, ( 2 )], have –C(H_α)₂OC(H_β)₂CF₂H side chains with H‐atom donors at the α and β sites. The structures of ( 1 ) and ( 2 ) are isomorphous, with the nearly planar (bpy)M Cl₂ molecules stacked in columns. Within one column, π‐dimer pairs alternate between a π‐dimer pair reinforced with C—H…Cl hydrogen bonds (α,α) and a π‐dimer pair reinforced with C—H_β…F(—C) interactions (abbreviated as C—H_β…F—C,C—H_β…F—C). The compounds [4,4′‐(CF₃CH₂OCH₂)₂‐2,2′‐bpy]M Cl₂ [M = Pd, ( 3 ), and M = Pt, ( 4 )] have been reported to be isomorphous [Lu et al. (2012). J. Fluorine Chem. 137 , 54–56], yet with disorder in the fluorous regions. The molecules of ( 3 ) [or ( 4 )] also form similar stacks, but with alternating π‐dimer pairs between the (α,β; α,β) and (β,β) forms. Through (C—)H…Cl hydrogen‐bond interactions, one molecule of ( 1 ) [or ( 2 )] is expanded into an aggregate of two inversion‐related π‐dimer pairs, one pair in the (α,α) form and the other pair in the (C—H_β…F—C,C—H_β…F—C) form, with the plane normals making an interplanar angle of 58.24 (3)°. Due to the demands of maintaining a high coordination number around the metal‐bound Cl atoms in molecule ( 1 ) [or ( 2 )], the ponytails of molecule ( 1 ) [or ( 2 )] bend outward; in contrast, the ponytails of molecule ( 3 ) [or ( 4 )] bend inward.     

Di­chloro­[(6R,7S,8S,14S)‐(–)‐sparteine‐κ2N,N′]­nickel(II)

In the title compound, [NiCl₂(C₁₅H₂₆N₂)], the chiral alkaloid (6R,7S,8S,14S)‐(−)‐l ‐sparteine acts as a bidentate ligand, with two chloride ligands occupying the remaining coordination sites, producing a slightly distorted tetrahedron. The N—Ni—N plane in the title complex is twisted by 81.31 (11)° from the Cl—Ni—Cl plane. Other distortions of the tetrahedron are discussed.     

Synthesis,crystal structure and photophysical properties of 1,4‐bis(1,3‐diazaazulen‐2‐yl)benzene: a new π building block

A dimerized 1,3‐diazaazulene derivative, namely 1,4‐bis(1,3‐diazaazulen‐2‐yl)benzene [or 2,2′‐(1,4‐phenylene)bis(1,3‐diazaazulene)], C₂₂H₁₄N₄, (I), has been synthesized successfully through the condensation reaction between 2‐methoxytropone and benzene‐1,4‐dicarboximidamide hydrochloride, and was characterized by ¹H NMR and ¹³C NMR spectroscopies, and ESI–MS. X‐ray diffraction analysis reveals that (I) has a nearly planar structure with good π‐electron delocalization, indicating that it might serve as a π building block. The crystal belongs to the monoclinic system. One‐dimensional chains were formed along the a axis through π–π interactions and adjacent chains are stabilized by C—H…N interactions, forming a three‐dimensional architecture. The solid emission of (I) in the crystalline form exhibited a 170 nm red shift compared with that in the solution state. The observed optical bandgap for (I) is 3.22 eV and a cyclic voltammetry experiment confirmed the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). The calculated bandgap for (I) is 3.37 eV, which is very close to the experimental result. In addition, the polarizability and hyperpolarizability of (I) were appraised for its further application in second‐order nonlinear optical materials.     

Effect of the position of a methoxy substituent on the antimicrobial activity and crystal structures of 4‐methyl‐1,6‐diphenylpyrimidine‐2(1H)‐selenone derivatives

Derivatives of pyrimidine‐2(1H)‐selenone are a group of compounds with very strong antimicrobial activity. In order to study the effect of the position of the methoxy substituent on biological activity, molecular geometry and intermolecular interactions in the crystal, three derivatives were prepared and evaluated with respect to their antimicrobial activities, and their crystal structures were determined by X‐ray diffraction. The investigated compounds, namely, 1‐(X‐methoxyphenyl)‐4‐methyl‐6‐phenylpyrimidine‐2(1H)‐selenones (X = 2, 3 and 4 for 1 , 2 and 3 , respectively), C₁₈H₁₆N₂OSe, showed very strong activity against selected strains of Gram‐positive bacteria and fungi. Two compounds, 1 and 2 , crystallize in the monoclinic space group P2₁/c, while 3 crystallizes in the space group P2₁/n; 1 has two molecules in the asymmetric unit and the other two ( 2 and 3 ) have one molecule. The geometries of the investigated compounds differ slightly in the mutual orientations of the aromatic and pyrimidineselenone rings. The O atom in 1 stabilizes the conformation of the molecules via intramolecular C—H…O hydrogen bonding. The packing of molecules is determined by weak C—H…N and C—H…Se intermolecular interactions and additionally in 1 and 2 by C—H…O intermolecular interactions. The introduction of the methoxy substituent results in greater selectivity of the investigated compounds.     

Structural insights into methyl‐ or methoxy‐substituted 1‐(α‐aminobenzyl)‐2‐naphthol structures: the role of C—H…π interactions

Aminobenzylnaphthols are a class of compounds containing a large aromatic molecular surface which makes them suitable candidates to study the role of C—H…π interactions. We have investigated the effect of methyl or methoxy substituents on the assembling of aromatic units by preparing and determining the crystal structures of (S,S)‐1‐{(4‐methylphenyl)[(1‐phenylethyl)amino]methyl}naphthalen‐2‐ol, C₂₆H₂₅NO, and (S,S)‐1‐{(4‐methoxyphenyl)[(1‐phenylethyl)amino]methyl}naphthalen‐2‐ol, C₂₆H₂₅NO₂. The methyl group influenced the overall crystal packing even if the H atoms of the methyl group did not participate directly either in hydrogen bonding or C—H…π interactions. The introduction of the methoxy moiety caused the formation of new hydrogen bonds, in which the O atom of the methoxy group was directly involved. Moreover, the methoxy group promoted the formation of an interesting C—H…π interaction which altered the orientation of an aromatic unit.     

Di­bromo­[(–)‐sparteine‐κ2N,N′]­zinc(II)

In the title compound, di­bromo­[(6R,7S,8S,14S)‐1,3,4,7,7a,8,9,10,11,13,14,14a‐dodeca­hydro‐7,14‐methano‐2H,6H‐dipyrido­[1,2‐a:1′,2′‐e][1,5]­diazo­cine‐κ²N,N′]­zinc(II), [ZnBr₂(C₁₅H₂₆N₂)], the chiral nitro­gen‐chelating alkaloid (?)‐l ‐sparteine acts as a bidentate ligand, with two bromide ligands occupying the remaining coordination sites, producing a slightly distorted tetrahedral structure. The dihedral angle between the N—Zn—N and Br—Zn—Br planes is 82.4 (1)°. The distortion of the tetrahedral coordination is demonstrated by the fact that the midpoint of the N?N line does not lie in the Br—Zn—Br plane, but is tilted towards one of the N atoms by 0.164 Å. Similarly, the midpoint of the Br?Br line is tilted towards one of the Br atoms by 0.117 Å.     

Hydrogen bonding and π–π interactions in the cocrystal salt [Fe(bpe)2(H2O)4](TCEP)2·2(bpe) [bpe is trans‐1,2‐bis(pyridin‐4‐yl)ethene and TCEP is 1,1,3,3‐tetracyano‐2‐ethoxypropenide]

The cocrystal salt tetraaquabis[trans‐1,2‐bis(pyridin‐4‐yl)ethene‐κN]iron(II) bis(1,1,3,3‐tetracyano‐2‐ethoxypropenide)–trans‐1,2‐bis(pyridin‐4‐yl)ethene (1/2), [Fe(C₁₂H₁₀N₂)₂(H₂O)₄](C₉H₅N₄O)₂·2C₁₂H₁₀N₂, is a rare example of a mononuclear Fe^II compound with trans‐1,2‐bis(pyridin‐4‐yl)ethane (bpe) ligands. The complex cation resides on a crystallographically imposed inversion center and exhibits a tetragonally distorted octahedral coordination geometry. Both the symmetry‐independent bpe ligand and the cocrystallized bpe molecule are essentially planar. The 1,1,3,3‐tetracyano‐2‐ethoxypropenide counter‐ion is nonplanar and the bond lengths are consistant with significant electron delocalization. The extended structure exhibits an extensive O—H…N hydrogen‐bonding network with layers of complex cations joined by the cocrystallized bpe. Both the coordinated and the cocrystallized bpe are involved in π–π interactions. Hirshfeld and fingerprint plots reveal the important intermolecular interactions. Density functional theory was used to estimate the strengths of the hydrogen‐bonding and π–π interactions, and suggest that the O—H…N hydrogen bonds enhance the strength of the π‐interactions by increasing the polarization of the pyridine rings.     

Crystal structures of the anhydrous and two solvated forms of methyl 4‐(4‐fluorophenyl)‐6‐methyl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate

Methyl 4‐(4‐fluorophenyl)‐6‐methyl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate, ( I ), was found to exhibit solvatomorphism. The compound was prepared using a classic Biginelli reaction under mild conditions, without using catalysts and in a solvent‐free environment. Single crystals of two solvatomorphs and one anhydrous form of ( I ) were obtained through various crystallization methods. The anhydrous form, C₁₃H₁₃FN₂O₃, was found to crystallize in the monoclinic space group C2/c. It showed one molecule in the asymmetric unit. The solvatomorph with included carbon tetrachloride, C₁₃H₁₃FN₂O₃·0.25CCl₄, was found to crystallize in the monoclinic space group P2/n. The asymmetric unit revealed two molecules of ( I ) and one disordered carbon tetrachloride solvent molecule that lies on a twofold axis. A solvatomorph including ethyl acetate, C₁₃H₁₃FN₂O₃·0.5C₄H₈O₂, was found to crystallize in the triclinic space group P with one molecule of ( I ) and one solvent molecule on an inversion centre in the asymmetric unit. The solvent molecules in the solvatomorphs were found to be disordered, with a unique case of crystallographically induced disorder in ( I ) crystallized with ethyl acetate. Hydrogen‐bonding interactions, for example, N—H…O=C, C—H…O=C, C—H…F and C—H…π, contribute to the crystal packing with the formation of a characteristic dimer through N—H…O=C interactions in all three forms. The solvatomorphs display additional interactions, such as C—F…N and C—Cl…π, which are responsible for their molecular arrangement. The thermal properties of the forms were analysed through differential scanning calorimetry (DSC), hot stage microscopy (HSM) and thermogravimetric analysis (TGA) experiments.     

Dichloro­[(6R,7S,8S,14S)‐(–)‐sparteine‐κ2N,N′]mercury(II)

In the title compound, [HgCl₂(C₁₅H₂₆N₂)], the chiral alkaloid (6R,7S,8S,14S)‐(−)‐l ‐sparteine acts as a bident­ate ligand, with two Cl⁻ ligands occupying the remaining coordination sites, producing a distorted tetra­hedron. The N—Hg—N plane is twisted by 81.1 (2)° from the Cl—Hg—Cl plane. The mid‐point of the N⋯N line does not lie exactly on the Cl—Hg—Cl plane but is tilted towards one of the N atoms by 0.346 Å. Similarly, the mid‐point of the Cl⋯Cl line is tilted toward one of the Cl atoms by 0.163 Å. The packing structure shows that the complex is stabilized by two inter­atomic Cl⋯H contacts involving both Cl atoms and the methyl­ene or methine H atoms of the (−)‐sparteine ligand.     

Helical supramolecular assembly of N2,N2′‐bis[3‐(morpholin‐4‐yl)propyl]‐N1,N1′‐(1,2‐phenylene)dioxalamide dimethyl sulfoxide monosolvate

In the title compound, C₂₄H₃₆N₆O₆·C₂H₆OS, the carbonyl groups are in an antiperiplanar conformation, with O=C—C=O torsion angles of 178.59 (15) and −172.08 (16)°. An intramolecular hydrogen‐bonding pattern is depicted by four N—H...O interactions, which form two adjacent S(5)S(5) motifs, and an N—H...N interaction, which forms an S(6) ring motif. Intermolecular N—H...O hydrogen bonding and C—H...O soft interactions allow the formation of a meso‐helix. The title compound is the first example of a helical 1,2‐phenylenedioxalamide. The oxalamide traps one molecule of dimethyl sulfoxide through N—H...O hydrogen bonding. C—H...O soft interactions give rise to the two‐dimensional structure.     

(1R,2R)‐1,2‐Di­phenyl‐1,2‐bis(8‐quinoline­sulfonyl­amino)ethyl­enedi­amine–acetone (1/1)

The crystal structure of the new chiral complex (1R,2R)‐1,2‐di­phenyl‐1,2‐bis(8‐quinoline­sulfonyl­amino)‐ ethyl­enedi­amine–acetone (1/1), C₃₂H₂₆N₄O₄S₂^.C₃H₆O, is reported. The conformation of the C₃₂H₂₆N₄O₄S₂ (BQSDA) mol­ecule is determined by a bifurcated N—H?N hydrogen‐bond system. The acetone of solvation is linked to the BQSDA mol­ecule by an N—H?O hydrogen bond.