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Paracetamol is an important analgesic and antipyretic drug showing poor tabletability. Among the various approaches used to improve this property, understanding the forces that govern the crystal packing is revealed to be crucial. We prepared three stable compounds: (par) 2 ∙(nap) ( 1 ), (par)∙(quin) ( 2 ), and (par)∙(acr) ( 3 ) (nap-naphthalene, quin-quinoline, acr-acridine) being cocrystals or solvate. The structural studies showed that all the reported compounds are composed of alternately arranged layers of paracetamol and coformer. Several supramolecular motifs in the paracetamol layer were identified: R44(22) in ( 1 ); R64(20) and R22(8) in ( 2 ); and R22(8), R42(12), and R44(26) rings in ( 3 ). The stability of the crystal network was studied by interactions analysis performed by Hirshfeld surface and fingerprint approaches and the energy between the closest units in the crystal network was calculated. It showed that the strongest interactions were found between blocks connected by N-H⋯O=C and O-H⋯O/N hydrogen bonds due to an important coulombic factor. The dispersive energy becomes important for tail-to-tail (and head-to-tail) arranged paracetamol units, and it prevails in the case of stacking interactions between coformer molecules. The importance of dispersive forces increases with the size of the aromatic system of the coformer. XAS studies confirmed the successful preparation of compounds and provided some details about electron structure.

Norfloxacin (NORF) is a broad-spectrum quinolone that is widely utilized for the treatment of various bacterial infections and is considered one of the most commonly used fluoroquinolone antibiotics. However, NORF's clinical utility is limited by its poor water solubility and relatively low oral bioavailability. This study presents an optimization and synergistic enhancement approach through salt/co-crystal, aiming to maximize the biopharmaceutical properties of NORF with the use of phenolic acid. Following this strategy, two new hydrate salts of NORF with phenolic acid, namely, NORF-3,5-DBA hydrate (salt 1 ) and NORF-VA hydrate (salt 2 ), were prepared and systematically confirmed. Two hydrate salts were produced by means of the slow evaporation crystallization method, and the structures were determined through single-crystal X-ray diffraction (SCXRD). Additionally, powder X-ray diffraction (PXRD), Fourier-transform infrared (FT-IR) spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and high-performance liquid chromatography (HPLC) were applied to analyze the features of the two salts. The experimental results indicated that the formation of the two salts could enhance the solubility and improve the release behavior of NORF. Interestingly, the physicochemical properties of NORF were significantly improved as a result, leading to an enhancement in its antibacterial activity. This was demonstrated by the enhanced inhibition of bacterial strains and the lower minimum inhibitory concentration values.

In the title compound, C 27 H 19 O 3 N, the dihedral angle between the aromatic rings of the biphenyl unit is 38.14 (2)° and the C-O-C-C torsion angle in the benz-yloxy benzene fragment is 179.1 (2)°. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions forming S (9) chains propagating along [010]. The most important contributions to the Hirshfeld surface arise from H⋯H (32.4%) and C⋯H/H⋯C (37.0%) contacts., (© Harish Kumar et al. 2024.)

The present study focuses on the synthesis and structural characterization of a novel dinuclear Cu II complex, [tri-chlorido-copper(II)]-μ-chlorido-{bis-[2-hy-droxy- N '-(propan-2-yl-idene)benzohydrazide]copper(II)} monohydrate, [Cu 2 Cl 4 (C 10 H 12 N 2 O 2 ) 2 ]·H 2 O or [Cu(H 2 L ) 2 (μ-Cl)CuCl 3 ]·H 2 O [H 2 L = 2-hy-droxy- N '-(propan-2-yl-idene)benzohydrazide]. The complex crystallizes in the monoclinic space group P 2 1 / n with one mol-ecule of water, which forms inter-actions with the ligands. The first copper ion is penta-coordinated to two benzohydrazine-derived ligands via two nitro-gen and two oxygen atoms, and one bridging chloride, which is also coordinated by the second copper ion alongside three terminal chlorines in a distorted tetra-hedral geometry. The arrangement around the first copper ion exhibits a distorted geometry inter-mediate between trigonal bipyramidal and square pyramidal. In the crystal, chains are formed via inter-molecular inter-actions along the a- plane, resulting in a three-dimensional network. The inter-molecular inter-actions in the crystal structure were qu-anti-fied and analysed using Hirshfeld surface analysis. Residual electron density from disordered methanol mol-ecules in the void space could not be reasonably modelled, thus a solvent mask was applied.ac plane, and through slipped π-π stacking inter-actions parallel to the ab plane, resulting in a three-dimensional network. The inter-molecular inter-actions in the crystal structure were qu-anti-fied and analysed using Hirshfeld surface analysis. Residual electron density from disordered methanol mol-ecules in the void space could not be reasonably modelled, thus a solvent mask was applied., (© Boulguemh et al. 2024.)

Twelve spiro thiazolidinone compounds (A-L) were synthesized via either conventional thermal or ultrasonication techniques using Fe 2 O 3 nanoparticles. The modification of the traditional procedure by using Fe 2 O 3 nanoparticles led to enhancement of the yield of the desired candidates to 78-93% in approximately half reaction time compared with 58-79% without catalyst. The products were fully characterized using different analytical and spectroscopic techniques. The structure of the two derivatives 4-phenyl-1-thia-4-azaspirodecan-3-one (A) and 4-(p-tolyl)-1-thia-4-azaspirodecan-3-one (B) were also determined using single crystal X-ray diffraction and Hirshfeld surface analysis. The two compounds (A and B) were crystallized in the orthorhombic system with Pbca and P2 1 2 1 2 1 space groups, respectively. In addition, the crystal packing of compounds revealed the formation of supramolecular array with a net of intermolecular hydrogen bonding interactions. The energy optimized geometries of some selected derivatives were performed by density functional theory (DFT/B3LYP). The reactivity descriptors were also calculated and correlated with their biological properties. All the reported compounds were screened for antimicrobial inhibitions. The two derivatives, F and J, exhibited the highest levels of bacterial inhibition with an inhibition zone of 10-17 mm. Also, the two derivatives, F and J, displayed the most potent fungal inhibition with an inhibition zone of 15-23 mm. Molecular docking investigations of some selected derivatives were performed using a B-DNA (PDB: 1BNA) as a macromolecular target. Structure and activity relationship of the reported compounds were correlated with the data of antimicrobial activities and the computed reactivity parameters., (© 2024. The Author(s).)

Starting from [Mn(C 5 H 4 Br)(PPh 3 )(CO) 2 ] (1a), the cymantrenyl thioethers [Mn(C 5 H 4 SMe)(PPh 3 )(CO) 2 ] (1b) and [Mn{C 5 H 4-n Br(SMe) n }(PPh 3 )(CO) 2 ] (n = 1 for compound 2, n = 2 for 3 and n = 3 for 4) were obtained, using either n-butyllithium (n-BuLi), lithium diisopropylamide (LDA) or lithium tetramethylpiperidide (LiTMP) as base, followed by electrophilic quenching with MeSSMe. Stepwise consecutive reaction of [Mn(C 5 Br 5 )(PPh 3 )(CO) 2 ] with n-BuLi and MeSSMe led finally to [Mn{C 5 (SMe) 5 }(PPh 3 )(CO) 2 ] (11), only the fifth complex to be reported containing a perthiolated cyclopentadienyl ring. The molecular and crystal structures of 1b, 3, 4 and 11 were determined and were studied for the occurrence of S...S and S...Br interactions. It turned out that although some interactions of this type occurred, they were of minor importance for the arrangement of the molecules in the crystal., (open access.)

A new one-dimensional thiocyanate-bridged cobalt(III) Schiff base complex, namely, catena-poly[[[4-bromo-2-((Z)-{[2-(thiophen-2-yl)ethyl]imino}methyl)phenolato-κ 2 N,O]cobalt(III)]-μ-thiocyanato-κ 2 N:S], [Co(SCN)(C 13 H 11 BrNOS) 2 ] n or [Co(μ 1,3 -SCN)L 2 ] n (1), where HL is 4-bromo-2-((Z)-{[2-(thiophene-2-yl)ethyl]imino}methyl)phenol, a bidentate Schiff base prepared from the condensation reaction of 5-bromosalicylaldehyde and 2-(thiophen-2-yl)ethylamine, has been synthesized by stirring Co(ClO 4 ) 2 ·6H 2 O, the Schiff base HL and ammonium thiocyanate (in a 1:2:1 molar ratio) in ethanol medium. The complex was characterized by FT-IR, electronic spectra and single-crystal X-ray diffraction (SC-XRD) studies. The SC-XRD data suggest that the compound crystallizes in the orthorhombic space group Pca2 1 . The Co III ion in 1 adopts a distorted octahedral geometry, the metal sites being six-coordinated by one thiocyanate N atom and one thiocyanate S atom in apical positions, and by two imine N atoms and two phenolate O atoms from two anionic L - ligands which form the basal plane. The thiocyanate ligand acts as a μ-1,3 bridge, joining neighbouring Co III atoms and forming a uniform zigzag one-dimensional polymeric chain. The crystallographic data were also used in the Hirshfeld surface (HS) analysis, which aimed to investigate the nature and quantitative significance of any noncovalent intermolecular interactions inside the crystal lattice. The crystal void parameters have also been computed and show the molecules to be tightly packed.

Two ionic hydrogen-bonded organic frameworks (iHOFs) assembled from 4-cyano-N-(4-cyanobenzyl)pyridinium, have been crystallized with Br - and antimony(III) pentabromide, [SbBr 5 ] 2- , as counter-ions and characterized. These are 4-cyano-N-(4-cyanobenzyl)pyridinium bromide, C 14 H 10 N 3 + ·Br - , and bis[4-cyano-N-(4-cyanobenzyl)pyridinium] antimony(III) pentabromide, (C 14 H 10 N 3 ) 2 ]. The CH...NC interactions induced by templating anions construct disparate frameworks. Hirshfeld surface analysis indicated that these crystals exhibit two types of hydrogen-bonding interactions, specifically CH...NC and CH...Br. Consecutive reverse-parallel CH...NC hydrogen-bonding interactions in these crystals induced the formation of a large number of CH...NC bonds which exhibit both cis and trans configurations.5 ]. The CH...NC interactions induced by templating anions construct disparate frameworks. Hirshfeld surface analysis indicated that these crystals exhibit two types of hydrogen-bonding interactions, specifically CH...NC and CH...Br. Consecutive reverse-parallel CH...NC hydrogen-bonding interactions in these crystals induced the formation of a large number of CH...NC bonds which exhibit both cis and trans configurations.

Pure and chromium (Cr) doped L-asparagine monohydrate (LAM) single crystals were grown by using evaporation controlled solution growth technique. XRD analysis confirmed the orthorhombic crystal system with space group P2 1 2 1 2 1 of grown crystals. Cr-incorporation decreased the cell parameters and unit cell volume of the crystals. Intermolecular interactions were analysed through Hirshfeld and fingerprint studies. SEM analysis showed the appearance of pits on the smooth surface of pure crystal due to Cr-addition. UV-Vis analysis showed high transparency, low cut-off and direct band gap of 5.42 eV and 5.51 eV for pure and Cr doped crystals, respectively. Fundamental functional groups were identified by FTIR and Raman spectroscopy. The thermal stability and melting point of the crystals were investigated using TGA/DSC analysis. The dielectric constant for doped LAM was increased to 44 as compare to dielectric constant of pure crystal which was 32. Both crystals showed low dielectric loss, having values 0.04 and 0.006 for pure LAM and doped crystals, respectively. In Vickers microhardness test, Cr doping was found to change the nature of pure LAM crystal from 'soft' to 'hard' as Meyer's index changed from 2.48 to 1.24., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

The synthesis, crystal structure, and a Hirshfeld surface analysis of tris-{ N , N -diethyl- N '-[(4-nitro-phen-yl)(oxo)meth-yl]carbamimido-thio-ato}cobalt(III) conducted at 180 K are presented. The complex consists of three N , N -diethyl- N '-[(4-nitro-benzene)(oxo)meth-yl]carbamimido-thio-ato ligands, threefold sym-metric-ally bonded about the Co III ion, in approximately octa-hedral coordination, which generates a triple of individually near planar metallacyclic (Co-S-C-N-C-O) rings. The overall geometry of the complex is determined by the mutual orientation of each metallacycle about the crystallographically imposed threefold axis [dihedral angles = 81.70 (2)°] and by the dihedral angles between the various planar groups within each asymmetric unit [metallacycle to benzene ring = 13.83 (7)°; benzene ring to nitro group = 17.494 (8)°]. The complexes stack in anti-parallel columns about the axis of the space group ( P ), generating solvent-accessible channels along [001]. These channels contain ill-defined, multiply disordered, partial-occupancy solvent. Atom-atom contacts in the crystal packing predominantly (∼96%) involve hydrogen, the most abundant types being H⋯H (36.6%), H⋯O (31.0%), H⋯C (19.2%), H⋯N (4.8%), and H⋯S (4.4%)., (© Roecker and Parkin 2024.)

The current article reports the investigation of three new Ni(II) complexes with ONS -donor dithiocarbazate ligands: [Ni(L 1 )PPh 3 ] ( 1 ), [Ni(L 2 )PPh 3 ] ( 2 ), and [Ni(L 2 )Py] ( 3 ). Single-crystal X-ray analyses revealed mononuclear complexes with a distorted square planar geometry and the metal centers coordinated with a doubly deprotonated dithiocarbazate ligand and coligand pyridine or triphenylphosphine. The non-covalent interactions were investigated by the Hirshfeld surface and the results revealed that the strongest interactions were π⋅⋅⋅π stacking interactions and non-classical hydrogen bonds C-H···H and C-H···N. Physicochemical and spectroscopic methods indicate the same structures in the solid state and solution. The toxicity effects of the free ligands and Ni(II) complexes were tested on the human breast cancer cell line MCF-7 and non-malignant breast epithelial cell line MCF-10A. The half-maximal inhibitory concentration (IC 50 ) values, indicating that the compounds were potent in inhibiting cell growth, were obtained for both cell lines at three distinct time points. While inhibitory effects were evident in both malignant and non-malignant cells, all three complexes demonstrated lower IC 50 values for malignant breast cell lines than their non-malignant counterparts, suggesting a stronger impact on cancerous cell lines. Furthermore, molecular docking studies were performed showing the complex ( 2 ) as a promising candidate for further therapeutic exploration.

In the crystal of the title compound, C 15 H 16 O 4 , the mol-ecules are connected through C-H⋯O hydrogen bonds, generating [100] chains, which are crosslinked by weak π-π stacking inter-actions., (© Bationo et al. 2024.)

The crystal structure of 4-methylcatechol (4MEC) has, to date, never been solved, despite its very simple chemical formula C 7 O 2 H 8 and the many possible applications envisaged for this molecule. In this work, this gap is filled and the structure of 4MEC is obtained by combining X-ray powder diffraction and first principle calculations to carefully locate hydrogen atoms. Two molecules are present in the asymmetric unit. Hirshfeld analysis confirmed the reliability of the solved structure, since the two molecules show rather different environments and H-bond interactions of different directionality and strength. The packing is characterised by a peculiar hydrogen bond network with hydroxyl nests formed by two adjacent octagonal frameworks. It is noteworthy that the observed short contacts suggest strong inter-molecular interactions, further confirmed by strong inter-crystalline aggregation observed by microscopic images, indicating the growth, in many crystallization attempts, of single aggregates taller than half a centimetre and, often, with spherical shapes. These peculiarities are induced by the presence of methyl group in 4MEC, since the parent compound catechol, despite its chemical similarity, shows a standard layered packing alternating hydrophobic and polar layers. Finally, the complexity and peculiarity of the packing and crystal growth features explain why a single crystal could not be obtained for a standard structural analysis.

Context: The controlled slow evaporation process conducted at room temperature has produced a novel hybrid material denoted as (2-hydroxyethyl) trimethylammonium dihydrogen phosphate [2-HDETDHP] (C 5 H 14 NO + , H 2 PO 4 ), synthesized through the solution growth method. X-ray crystallography analysis reveals a triclinic structure with a filling rate of P and a Z value of 2. This hybrid material displays noteworthy absorption characteristics in the middle and far ultraviolet regions. UV-visible spectroscopy further establishes its transparency in the visible and near-visible ultraviolet domains. FT-IR spectroscopy examines various vibration modes, elucidating their relationships with the functional groups within the structure. Two- and three-dimensional fingerprint maps, coupled with three-dimensional crystal structures through Hirshfeld Surface Analysis, unveil the dominance of O•••H and H•••H interactions in the structure, comprising 49.40% and 50.40%, respectively. Fingerprint plots derived from the Hirshfeld surface assess the percentages of hydrogen bonding interactions, with 80.6% attributed to a fragment patch. The experiment of antimicrobial efficacy of a synthesized product, conducted in triplicate, demonstrated the synthesized product's potential antimicrobial activity.- ), synthesized through the solution growth method. X-ray crystallography analysis reveals a triclinic structure with a filling rate of P and a Z value of 2. This hybrid material displays noteworthy absorption characteristics in the middle and far ultraviolet regions. UV-visible spectroscopy further establishes its transparency in the visible and near-visible ultraviolet domains. FT-IR spectroscopy examines various vibration modes, elucidating their relationships with the functional groups within the structure. Two- and three-dimensional fingerprint maps, coupled with three-dimensional crystal structures through Hirshfeld Surface Analysis, unveil the dominance of O•••H and H•••H interactions in the structure, comprising 49.40% and 50.40%, respectively. Fingerprint plots derived from the Hirshfeld surface assess the percentages of hydrogen bonding interactions, with 80.6% attributed to a fragment patch. The experiment of antimicrobial efficacy of a synthesized product, conducted in triplicate, demonstrated the synthesized product's potential antimicrobial activity., Methods: Hirshfeld surfaces are employed to investigate intermolecular hydrogen bonding, specifically within single phosphate groups. The molecular structure of 2-HDETDHP was refined using single-crystal X-ray analysis, while its optical characteristics were examined through UV-visible spectroscopy. FT-IR spectroscopy is employed for the assignment of molecular vibrations of functional groups in the affined structure. Quantum calculations were executed with the GAUSSIAN 09 software package at B3LYP/6-311G level of theory, to optimize the molecular geometries. The antimicrobial efficacy of a synthesized product was evaluated using the disc diffusion method against antibiotic-resistant Candida albicans, Candida tropicalis, Aspergillus niger, Staphylococcus aureus, and Escherichia coli. Microorganisms were cultured on nutrient agar, and inhibition zones were measured after incubation, with streptomycin and amphotericin as positive controls., (© 2024. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

In the crystal of the title compound, C 18 H 14 O 10 ·2H 2 O, the arene rings of the biphenyl moiety are tilted at an angle of 24.3 (1)°, while the planes passing through the carboxyl groups are rotated at angles of 8.6 (1) and 7.7 (1)° out of the plane of the benzene ring to which they are attached. The crystal structure is essentially stabilized by O-H⋯O bonds. Here, the carboxyl groups of neighbouring host mol-ecules are connected by cyclic R 2 -axis (chain-like water clusters). The second H atom of each water mol-ecule provides a link to a meth-oxy O atom of the host mol-ecule. A Hirshfeld surface analysis was performed to qu-antify the contributions of the different inter-molecular inter-actions, indicating that the most important contributions to the crystal packing are from H⋯O/O⋯H (37.0%), H⋯H (26.3%), H⋯C/C⋯H (18.5%) and C⋯O/O⋯C (9.5%) inter-actions.2 (8) synthons, leading to the formation of a three-dimensional network. The water mol-ecules in turn form helical supra-molecular strands running in the direction of the crystallographic c -axis (chain-like water clusters). The second H atom of each water mol-ecule provides a link to a meth-oxy O atom of the host mol-ecule. A Hirshfeld surface analysis was performed to qu-antify the contributions of the different inter-molecular inter-actions, indicating that the most important contributions to the crystal packing are from H⋯O/O⋯H (37.0%), H⋯H (26.3%), H⋯C/C⋯H (18.5%) and C⋯O/O⋯C (9.5%) inter-actions., (© Hanauer et al. 2024.)

The present work reports the influence of the presence of different ions (Cl - , Br - , NO 3 - , or SO 4 2- ) on the formation and proprieties of Cu(II) complexes with pyridoxal-benzoylhydrazone (PLBHZ). Four new complexes were successfully synthesized, [CuCl 2 (PLBHZ)] (1), [CuBr 2 (PLBHZ)] (2), [CuCl(PLBHZ)H 2 O]⋅NO 3 ⋅H 2 O (3), and [CuSO 4 (PLBHZ)H 2 -donor system, resulting in distorted square pyramidal coordination geometries. Noncovalent interactions were investigated by 3D Hirshfeld surface analysis by the 2 O (4), and characterized by spectroscopic and physicochemical methods. A single-crystal X-ray study reveals the Schiff base coordinated to the metal center tridentate by the ONS -donor system, resulting in distorted square pyramidal coordination geometries. Noncovalent interactions were investigated by 3D Hirshfeld surface analysis by the d norm function, 2D fingerprint plots, and full interaction maps. The ion exchange is important in forming three-dimensional networks with π⋅⋅⋅π stacking interactions and intermolecular hydrogen bonds. The in vitro biological activity of the free ligand and metal complexes was evaluated against Gram-positive and Gram-negative bacterial strains and the free pyridoxal-hydrazone ligand showed higher activity than their Cu(II) complexes. Molecular docking was used to predict the inhibitory activity of the ligand and complexes against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli bacteria., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2024 Gatto, Dias, Paiva, da Silva, Freire, Tormena, Nascimento and Martins.)

The title compound, C 27 H 20 N 4 O 3 S, crystallizes in the monoclinic system, space group P 2 1 / n , with Z = 4. The global shape of the mol-ecule is determined by the orientation of the substituents on the central 4 H -1,2,4-triazole ring. The nitro-phenyl ring, phenyl ring, and naphthalene ring system are oriented at dihedral angles of 82.95 (17), 77.14 (18) and 89.46 (15)°, respectively, with respect to the triazole ring. The crystal packing features chain formation in the b -axis direction by S⋯O inter-actions. A Hirshfeld surface analysis indicates that the highest contributions to surface contacts arise from contacts in which H atoms are involved., (© Le et al. 2024.)

The crystal structure of the new triclinic polymorph of miconazole {MIC; C 18 H 14 Cl 4 N 2 O; systematic name: ( RS )-1-[2-(2,4-di-chloro-benz-yloxy)-2-(2,4-di-chloro-phen-yl)eth-yl]-1 H -imidazole} is reported and compared with the monoclinic form of solvent-free miconazole previously reported [Kaspiaruk & Chęcińska (2022 ▸). Acta Cryst. C 78 , 343-350]. A comparison shows a different orientation of imidazole and one di-chloro-phenyl ring between polymorphic mol-ecules. In the crystal structure of the title compound, only weak halogen bonds and C-H⋯π(arene) inter-actions are found. Hirshfeld surface analysis and energy framework calculations complement the comparison of the two polymorphic forms of the miconazole drug., (© Kaspiaruk and Chęcińska 2024.)

In the title compound, C 20 H 18 O 4 , the dihedral angle between the 2 H -chromen-2-one ring system and the phenyl ring is 89.12 (5)°. In the crystal, the mol-ecules are connected through C-H⋯O hydrogen bonds to generate [010] double chains that are reinforced by weak aromatic π-π stacking inter-actions. The unit-cell packing can be described as a tilted herringbone motif. The H⋯H, H⋯O/O⋯H, H⋯C/C⋯H and C⋯C contacts contribute 46.7, 24.2, 16.7 and 7.6%, respectively, to its Hirshfeld surface., (© Kenfack Tsobnang et al. 2024.)

Four new coordination polymers, including 1D, 2D and 3D structures, were synthesized via a hydrothermal method using Cd 2+ /Zn 2+ /Cu 2+ metal salts as nodes. These polymers were formed through self-assembly of four different dicarboxylic acid ligands, namely adamantane-1,3-dicarboxylic acid (H 2 adc), glutaric acid (H 2 glu), 5-hydroxyisophthalic acid (H 2 hip) and fumaric acid (H 2 fum), in conjunction with the auxiliary ligand [1,4-bis(pyridin-4-ylmethyl)piperazine (bpmp). The corresponding formulae are [Cd 3 (adc) 2 (bpmp)Cl 2 (H 2 O) 2 ] n (1), {[Cd 2 (glu) 2 (bpmp) 2 (H 2 O) 2 ]·8H 2 O·2CH 3 OH} n (2), [Zn(hip)(bpmp)(H 2 O)] n (3) and [Cu(fum)(bpmp)(H 2 O) 2 ] n (4). Single-crystal X-ray diffraction studies revealed that the Cd 2+ centers in complex 1 all adopt a six-coordinate mode but two distinct {CdO 2 N 2 Cl 2 } and {CuO 5 Cl} units. The 3D network of complex 1 can be simplified to a binodal (4.6)-connected underlying net with the point symbol (3·4 2 ·5·6 2 ) 4 (3 2 ·6 2 ·7 2 ·8 8 ·10). Each Cd 2+ cation in complex 2 adopts a seven-coordinate {CdO 5 N 2 } center, forming an asymmetric pentagonal bipyramidal coordination. Its stacking structure is formed by the interaction of hydrogen bonds between 2D supramolecular layers, with the adjacent layers exhibiting mirror symmetry. Each Zn 2+ ion in complex 3 displays a {ZnO 3 N} four-coordinate unit. Its stacking structure is formed by one-dimensional [Zn(hip)(bpmp)(H 2 O)] n chains connected through hydrogen bonds. On the other hand, complex 4 features a Jahn-Teller distorted {CuO 4 N 2 } octahedral coordination. Subsequently, the thermal stability of these complexes was investigated. The solid-state fluorescence spectroscopy was employed to analyze complexes 1, 2 and 3. Additionally, a Hirshfeld surface analysis was performed on complex 3.

Despite extensive genetic and biochemical characterization, the molecular genetic basis underlying the biosynthesis of β-diketones remains largely unexplored. β-Diketones and their complexes find broad applications as biologically active compounds. In this study, in silico molecular docking results revealed that two β-diketone derivatives, namely 2-(2-(4-fluorophenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione and 5,5-dimethyl-2-(2-(2-(trifluoromethyl)phenyl)hydrazono)cyclohexane-1,3-dione, exhibit anti-COX-2 activities. However, recent docking results indicated that the relative anti-COX-2 activity of these two studied β-diketones was influenced by the employed docking programs. For improved design of COX-2 inhibitors from β-diketones, we conducted molecular dynamics simulations, density functional theory (DFT) calculations, Hirshfeld surface analysis, energy framework, and ADMET studies. The goal was to understand the interaction mechanisms and evaluate the inhibitory characteristics. The results indicate that 5,5-dimethyl-2-(2-(2-(trifluoromethyl)phenyl)hydrazono)cyclohexane-1,3-dione shows greater anti-COX-2 activity compared to 2-(2-(4-fluorophenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione.

Coordination polymers (CPs) are an assorted class of coordination complexes that are gaining attention for the safe and sustainable removal of organic dyes from wastewater discharge by either adsorption or photocatalytic degradation. Herein, three different coordination polymers with compositions [Ni(HL)(H 2 O) 2 ·1.9H 2 O] ( 1 ), [Mn 3 (HL)(L)(μ 3 -OH)(H 2 O)(phen) 2 ·2H 2 O] ( 2 ), and [Cd(HL) 4 (H 2 O)]·H 2 O ( 3 ) (H 3 L = 2-(3,5-dicarboxyphenyl)-6-carboxybenzimidazole; phen = 1,10-phenanthroline) have been synthesized and characterized spectroscopically and by single crystal X-ray diffraction. Single crystal X-ray diffraction results indicated that 1 forms a 2D layer-like framework, while 2 exhibits a 3-connected net with the Schläfli symbol of (4 4 .6), and 3 displays a 3D supramolecular network in which two adjacent 2D layers are held by π···π interactions. All three compounds have been used as photocatalysts to catalyze the photodegradation of antibiotic dinitrozole (DTZ) and rhodamine B (RhB). The photocatalytic results suggested that the Mn-based CP 2 exhibited better photodecomposition of DTZ (91.1%) and RhB (95.0%) than the other two CPs in the time span of 45 min. The observed photocatalytic mechanisms have been addressed using Hirshfeld surface analyses.

The reaction of o -phenyl-enedi-amine (OPD), sodium naphthalene1,5-di-sulfonate (Na 2 NDS) and nickel sulfate in an ethanol-water mixture yielded the title compound, [Ni(OPD) 2 (H 2 O) 2 ]·NDS or [Ni(C 6 H 8 N 2 ) 2 (H 2 O) 2 ](C 10 H 6 O 6 S 2 ). This salt consists of a complex [Ni(OPD) 2 (H 2 O) 2 ] 2+ cation with two bidentate OPD ligands and trans aqua ligands, and a non-coordinating NDS 2- anion, which is the double-deprotonated form of H 2 NDS. The Ni II atom is situated at a center of inversion and exhibits a slightly tetra-gonally distorted {O 2 N 4 } octa-hedral coordination environment, with four shorter equatorial Ni-N bonds [2.0775 (17) and 2.0924 (18) Å] and a longer axial Ni-O bond [2.1381 (17) Å]. The OPD ligand is located about an inversion center and is nearly coplanar with the NiN 4 plane [dihedral angle 0.95 (9)°]. In the crystal, the cations and anions are connected by charge-assisted inter-molecular N-H⋯O and O-H⋯O hydrogen-bonding inter-actions into the tri-periodic network structure. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (44.1%), O⋯H/H⋯O (34.3%), C⋯H/H⋯C (14.8%) C⋯C (6.5%) (involving the cations) and O⋯H/H⋯O (50%), H⋯H (25%), C⋯H/H⋯C (15.3%), C⋯C (8.2%) (involving the anions) inter-actions., (© Suyunov et al. 2023.)

Overall, drug design is a dynamic and evolving field, with researchers constantly working to improve their understanding of molecular interactions, develop new computational methods, and explore innovative techniques for creating effective and safe medications. The process can involve steps such as the identification of targets, the discovery of lead compounds, lead optimization, preliminary testing, human trials, regulatory approval and finally post-marketing surveillance, all aimed at bringing a new drug from concept to market. In this article, the synthesis of the novel triazolequinoxalin ( TZQ ) 1-((1-hexyl-1H-1,2,3-triazol-5-yl)methyl)-3-phenylquinoxalin-2(1H)-one ( 4 ) is reported. The structure has been identified with a variety of spectroscopic methods (1H, 13C NMR, and LC-MS) and finally, the structure has been determined by X-ray diffraction (XRD) studies. The TZQ molecule has crystallized in the monoclinic space C 2/ c group with unit cell dimensions a  = 41.201(2) Å, b  = 10.6339(6) Å, c  = 9.4997(4) Å, β  = 93.904(4). The crystal structure is stabilized by intermolecular interactions (N-H ⋯ O and N-H … Cg) occurring within the molecule. The presence of these intermolecular interactions is evaluated through analysis of Hirshfeld surfaces (HS) and two-dimensional (2D) chemical fingerprints map. Additionally, energy frameworks were employed to identify the prevailing interaction energy influencing the molecular arrangement. Density Functional Theory (DFT) calculations were computed to establish concurrence between theoretical and experimental results. Furthermore, the HOMO-LUMO energy levels were determined using the B3LYP/6-31+G(d, p) level of theory. Finally, molecular docking was used to predict the anti-cancer activity of the compound ( 4 ) against PFKFB3 kinase and presented noticeable hydrophilic and hydrophobic interactions at the active site region., Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (© 2023 The Authors.)

This study systematically investigates the molecular structure and electronic properties of 2-methoxy-4,6-diphenylnicotinonitrile, employing X-ray diffraction (XRD) and sophisticated computational methodologies. XRD findings validate the compound's orthorhombic crystallization in the P21212 space group, composed of a pyridine core flanked by two phenyl rings. Utilizing the three-dimensional Hirshfeld surface, the research decodes the molecule's spatial attributes, further supported by exhaustive statistical assessments. Key interactions, such as π-π stacking and H⋯X contacts, are spotlighted, underscoring their role in the crystal's inherent stability and characteristics. Energy framework computations and density functional theory (DFT) analyses elucidate the prevailing forces in the crystal and reveal geometric optimization facets and molecular reactivity descriptors. Emphasis is given to the exploration of frontier molecular orbitals (FMOs), aromaticity, and π-π stacking capacities. The research culminates in distinguishing electron density distributions, aromatic nuances, and potential reactivity hotspots, providing a holistic view of the compound's structural and electronic landscape. Concurrently, molecular docking investigates its interaction with the lipoprotein-associated phospholipase A2 protein. Notably, the compound showcases significant interactions with the protein's active site. Molecular dynamics simulations reveal the compound's influence on protein stability and flexibility. Although the molecule exhibits strong inhibitory potential against Lp-PLA2, its drug development prospects face challenges related to solubility and interactions with drug transport proteins.

The reaction of 8-amino-quinoline, zinc chloride and hydro-chloric acid in ethanol yielded the title salt, (C 9 H 10 N 2 )[ZnCl 4 ], which consists of a planar 8-aza-n-ium-yl-quinolinium dication and a tetra-hedral tetra-chloro-zincate dianion. The 8-amino-quinoline moiety is protonated at both the amino and the ring N atoms. In the crystal, the cations and anions are connected by inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming sheets parallel to (001). Adjacent sheets are linked through π-π inter-actions involving the pyridine and arene rings of the 8-aza-niumylquinolinium dication. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯Cl (48.1%), H⋯H (19.9%), H⋯C/C⋯H (14.3%) (involving the cations) and H⋯Cl (82.6%) (involving the anions) interactions., (© Umirova et al. 2023.)

3-ferrocenyl-estra-1,3,5 (10)-triene-17-one ( 2 ), [Fe(C 5 H 5 )(C 24 H 25 O 3 )], crystallizes in the monoclinic space group C2. The cyclopentadienyl (Cp) rings adopt a nearly eclipsed conformation, and the Cp plane is tilted by 87.66° with respect to the substituted phenyl plane. An average Fe-C(Cp) bond length of 2.040(13) Å was determined, similar to the one reported for ferrocene. Hirshfeld surfaces and two-dimensional fingerprint plots were generated to analyze weak intermolecular C-H···π and C-H···O interactions. Density functional theory studies revealed a 1.15 kcal/mol rotational barrier for the C3-O1 single bound. Fluorescence quenching studies and in silico docking studies suggest that human serum albumin forms a complex with 2 via a static mechanism dominated by van der Waals interactions and hydrogen bonding interactions.

In this investigation a single crystal of ( 4 - o xo- p iperidinium e thylene a cetal) trioxo n itrate ( 4-OPEAN ) was synthesized by modifying the mechanism of gradual evaporation at ambient temperature. The operational groupings are found in the complex material in the elaborate substance, according to the infrared spectrum. Single crystal X-ray diffraction suggests, (4 - OPEAN) with the chemical formula (C 7 H 12 NO 2 )NO 3 belongs to the orthorhombic space group P nma and is centrosymmetric in three dimensions with the aforementioned network configurations, a = 11.7185(8) Å, b = 7.2729(6) Å, c = 11.0163(8) Å, Z = 4, V = 938.89(12) Å 3 , R = 0.0725 and wR = 0.1762. Many N-H…O and C-H…O hydrogen bridges, both bifurcated and non-bifurcated, link the 4-oxo-piperidinium ethylene acetal cations to the trigonal (NO 3 - OPEAN) have been determined via DFT computations at the theory-level B3LYP/6-311 ++ G(d, p), these have been contrasted with the X-ray data already available. Hirshfeld surface analysis has made it possible for the visualization and quantification of relationships between molecules in the crystal composition. Quantum theory atoms in molecules, electron location function, decreased density gradient, and localized orbital locator research have all been used to explore non-covalent interactions in crystal structure. In order to pinpoint both the nucleophilic and electrophilic locations that support hydrogen bond formation, the molecule electrostatic potential was determined. The greatest and lowest energies of occupied and unfilled molecular orbitals, together with additional derived atomic characteristics, show the material to be extremely stable and hard. According to a molecular docking study, 4 - OPEAN) have been determined via DFT computations at the theory-level B3LYP/6-311 ++ G(d, p), these have been contrasted with the X-ray data already available. Hirshfeld surface analysis has made it possible for the visualization and quantification of relationships between molecules in the crystal composition. Quantum theory atoms in molecules, electron location function, decreased density gradient, and localized orbital locator research have all been used to explore non-covalent interactions in crystal structure. In order to pinpoint both the nucleophilic and electrophilic locations that support hydrogen bond formation, the molecule electrostatic potential was determined. The greatest and lowest energies of occupied and unfilled molecular orbitals, together with additional derived atomic characteristics, show the material to be extremely stable and hard. According to a molecular docking study, 4 - OPEAN may exhibit inhibiting effects on the 6Y84 and 7EJY virus proteins from corona (COVID-19)., Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (© 2023 Published by Elsevier B.V. on behalf of King Saud University.)

The current research describes the synthesis and characterization of 2-acetylpyridine N(4)-cyclohexyl-thiosemicarbazone ligand (HL) and their two metal complexes, [Au(L)Cl][AuCl 2 ] (1) and [Pd(L)Cl]·DMF (2) . The molecular structures of the compounds were determined by physicochemical and spectroscopic methods. Single crystal X-ray diffraction was employed in the structural elucidation of the new complexes. The complexes showed a square planar geometry to the metal center Au(III) and Pd(II), coordinated with a thiosemicarbazone molecule by the NNS -donor system and a chloride ion. Complex (1) also shows the [AuCl 2 ] - counter-ion in the asymmetric unit, and complex (2) has one DMF solvent molecule. These molecules play a key role in the formation of supramolecular structures due to different interactions. Noncovalent interactions were investigated through the 3D Hirshfeld surface by the d norm function and the 2D fingerprint plots. The biological activity of the compounds was evaluated in vitro against the human glioma U251 cells. The cytotoxicity results revealed great antitumor activity in complex (1) compared with complex (2) and the free ligand. Molecular docking simulations were used to predict interactions and properties with selected proteins and DNA of the synthesized compounds.

Context: The design and synthesis of safe and highly active sulfonylurea herbicides is still a challenge. Therefore, following some principles of structure-activity relationship (SAR) of sulfonylurea herbicides, this work focuses on evaluating two sulfonylurea derivatives bearing electron-withdrawing substituents, namely, -(CO)OCH 3 and -NO 2 on the aryl group, on herbicidal activity. To understand the effects caused by the substituent groups, the molecular and electronic structures of the sulfonylureas were evaluated by density functional theory. Likewise, the crystalline supramolecular arrangements of both compounds were analyzed by Hirshfeld surface, QTAIM, and NBO, with the aim of verifying changes in intermolecular interactions caused by substituent groups. Finally, through a toxicophoric analysis, we were able to predict the interacting groups in their biological target, acetolactate synthase, and verify the interactions with the binding site., Methods: All theoretical calculations were conducted using the highly parameterized empirical exchange-correlation functional M06-2X accompanied by the diffuse and polarized basis set 6-311++G(d,p). The atomic coordinates were obtained directly from the crystalline structures, and from the energies of the frontier molecular orbitals (HOMO and LUMO), chemical descriptors were obtained that indicated the influence of the functional groups in the sulfonylureas on the reactivity of the molecules. The intermolecular interactions in the crystals were analyzed using the Hirshfeld, QTAIM, and NBO surfaces. Toxicophoric modeling was performed by the PharmaGist webserver and molecular docking calculations were performed by the GOLD 2022.1.0 software package so that the ligand was fitted to the binding site in a 10 Å sphere. For this, genetic algorithm parameters were used using the ChemPLP scoring function for docking and ASP for redocking., (© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

A supramolecular self-assembly of semiconducting polymers and small molecules plays an important role in charge transportation, performance, and lifetime of an optoelectronic device. Tremendous efforts have been put into the strategies to self-organize these materials. In this regard, here, we present the self-organization of terthiophene and its methyl alcohol derivative with 4,4'-bipyridine (44BiPy). An unexpected 2D layered organization of 5,5″-dimethyl-2,2':5',2″-terthiophene (DM3T) and 44BiPy was obtained and analyzed. Single-crystal X-ray diffraction analysis revealed that DM3T and 44BiPy consist of stacked, almost independent, infinite 2D layers while held together by weak hydrogen bonds. In addition to this peculiar supramolecular arrangement of these compounds, the investigation of their photophysical properties showed strong fluorescence quenching of DM3T by 44BiPy in the solid state, suggesting an efficient charge transfer. On the other hand, the methyl alcohol derivative of terthiophene, DM3TMeOH, organized in a closed cyclic motif with 44BiPy via hydrogen bonds.

In the title compound, C 38 H 28 O 6 , the dihedral angles between the naphthalene ring system and its pendant benz-yloxy rings A and B are 88.05 (7) and 80.84 (7)°, respectively. The dihedral angles between the A and B rings and their attached phenyl rings are 49.15 (8) and 80.78 (8)°, respectively. In the extended structure, the mol-ecules are linked by weak C-H⋯O and C-H⋯π hydrogen bonds, and π-π stacking inter-actions, which variously generate C (11) chains and R (12) loops as part of a three-dimensional network. The Hirshfeld surface [fingerprint contributions = H⋯H (42.3%), C⋯H/H⋯C (40.3%) and O⋯H/H⋯O (15.7%)] and inter-molecular inter-action energies are reported, with dispersion ( 2 2 (12) loops as part of a three-dimensional network. The Hirshfeld surface [fingerprint contributions = H⋯H (42.3%), C⋯H/H⋯C (40.3%) and O⋯H/H⋯O (15.7%)] and inter-molecular inter-action energies are reported, with dispersion ( E dis = -428.6 kJ mol -1 ) being the major contributor., (© Anil Kumar et al. 2023.)

A single crystal X-ray diffraction analysis was performed on two positional isomers ( m -tolyl and p -tolyl) of acrylonitrile derivatives, namely, (Z)-3-(4-(pyridin-2-yl) phenyl)-2-(m-tolyl) acrylonitrile ( 1 ) and (Z)-3-(4-(pyridin-2-yl)phenyl)-2-(p-tolyl) acrylonitrile ( 2 ). Compound 1 crystallized in the monoclinic P 2 1 /n space group with two crystallographically independent molecules. Compound 2 also possesses two crystallographically independent molecules and crystallized in the triclinic P -1 space group. The Hirshfeld surface analysis revealed that, in both isomers, intermolecular H⋅⋅⋅H/C/N contacts contribute significantly to the crystal packing. More than 40% of the contribution arises from intermolecular C-H⋅⋅⋅C(π) contacts. In both compounds, the relative contribution of these contacts is comparable, indicating that the positional isomeric effects are marginal. The structures in which these isomers are arranged in the solid state are very similar, and the lattice energies are also comparable between the isomers. The Coulomb-London-Pauli-PIXEL (CLP-PIXEL) energy analysis identified the energetically significant dimers. The strength of the intra- and intermolecular interactions was evaluated using the quantum theory of atoms in molecules approach. The UV-Vis absorbance in three different solvents (chloroform, ethanol, and ethyl acetate) for isomers 1 and 2 are very similar. This result is in good agreement with the time-dependent density-functional theory (TD-DFT) calculations., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Percino, Udayakumar, Cerón, Pérez-Gutiérrez, Venkatesan and Thamotharan.)

The synthesis and crystal structure of a monoclinic polymorph of 2-amino-5-chloro-benzo-phenone oxime, C 13 H 11 ClN 2 O, are presented. The mol-ecular conformation results from twisting of the phenyl and 2-amino-5-chloro benzene rings attached to the oxime group, which subtend a dihedral angle of 80.53 (4)°. In the crystal, centrosymmetric dimers are formed as a result of pairs of strong O-H⋯N hydrogen bonds. A comparison is made to a previously known triclinic polymorph, including differences in atom-atom contacts obtained via a Hirshfeld-surface analysis., (© Geetha et al. 2023.)

Introduction: Enalapril maleate is an antihypertensive ethyl ester pro-drug with two crystalline forms. A network of hydrogen bonds in both polymorphs plays an important role on solid-state stability, charge transfer process and degradation reactions (when exposed to high humidity, temperature and/or pH changes)., Computational Procedures: Supramolecular arrangement was proposed by Hirshfeld surface using the CrystalExplorer17 software and quantum theory of atoms in molecules. The electronic structure properties were calculated using the functional hybrid M06-2X with 6-311++G** base function employing diffuse and polarization functions to improve the description of hydrogen atoms on intermolecular interactions. Also, the H+ charge transfer between enalapril and maleate molecules was performed using Car-Parrinello molecular dynamics with the Verlet algorithm. In both simulations, the temperature of the ionic system was maintained around 300 K using the Nosé-Hoover thermostat and the electronic system evolved without the use of the thermostat., Results: This work evaluates the effect of maleate on the structural stability of enalapril maleate solid state. The electronic structural analysis points out a partially covalent character for N1-H∙∙∙O7 interaction; and the molecular dynamic showed a decentralized hydrogen on maleate driving a decomposition by charge transfer process while a centered hydrogen driving the stabilization. The charge transfer process and the mobility of the proton (H+) between enalapril and maleate molecules was demonstrated using supramolecular modeling analyses and molecular dynamics calculations., (© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

Novel materials of (E)-N'-(4-chlorobenzylidene)-4-hydroxybenzohydrazide (CBHB) and (E)-N'-(4-(diethylamino) benzylidene)-4-hydroxybenzohydrazide (DEABHB) were synthesized by condensation reaction process and solvent evaporation method was employed to grow CBHB and DEABHB single crystals at room temperature. Lattice parameters of CBHB and DEABHB compounds were recorded using single crystal X-ray diffraction method. The presence of functional groups of the synthesized CBHB and DEABHB compounds were confirmed by Fourier transform infrared and Fourier transform Raman spectral analyses. Various intermolecular interactions were studied using Hirshfeld surface analysis. Thermal stability of the hydrazone Schiff base compounds CBHB and DEABHB were studied by thermogravimetric and differential thermal analyses. Third order nonlinear optical properties of CBHB and DEABHB were measured using open aperature Z scan technique. Two photon absorption coefficient and optical limiting properties of the crystals were reported from the Z scan studies., (© 2022. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)

In this study, polynuclear Cu(II) complex (1) , Mn(II) and Mn(III) complex (2) have been prepared with a Schiff base ligand derived from 2-Hydroxy-3-methoxybenzaldehyde with 2-amino-2-methyl-1-propanol. The compounds were characterized by elemental analysis, FT-IR, and UV-Vis spectroscopy. The molecular and crystal structures of (1-2) were determined by the single-crystal x-ray diffraction technique. It turned out that Cu(II) complex ( 1 ) forms an S 4 -symmetrical tetrameric cage structure, with square-planar coordinated Cu and bridging O atoms at the vertexes of the approximate cube. In the crystal structure of 1, there are large channels along the c-axis, between the tetramers; the solvent- DMSO molecules, occupies these channels. In turn, the complex (2) creates a centrosymmetric trimeric structure, with three octahedrally coordinated Mn ions bridged by O atoms from ligand molecules and acetate ions. The electrochemical behavior studies of the complexes in DMSO displayed the electronic effects of the groups on the redox potential. The redox behavior of Schiff base (1) and (2) complexes included quasi -reversible and irreversible voltammograms, respectively. Intermolecular interactions in the solid states were studied by Hirshfeld surface analysis. These studies provide a comprehensive description of these inter-contact exchanges using an attractive graphical representation using Hirshfeld surfaces and fingerprint plots, along with enrichment ratios. Furthermore, assessment of the inhibitory effect against coronavirus (main protease SARS-CoV-2) was performed by a molecular docking study for both complexes ( 1 and 2 ). Both complexes showed a good affinity for CoV-2 for PDB protein ID: 6M03 and 6Y2F., Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (© 2022 Elsevier B.V. All rights reserved.)

In recent years, fluorescent compounds that emit efficiently in the solid state have become particularly interesting, especially those that are easily prepared and inexpensive. Hence, exploring the photophysical properties of stilbene derivatives, supported by a detailed analysis of molecular packing obtained from single-crystal X-ray diffraction data, is a relevant area of research. A complete understanding of the interactions to determine the molecular packing in the crystal lattice and their effect on the material's physicochemical properties is essential to tune various properties effectively. In the present study, we examined a series of methoxy- trans -stilbene analogs with substitution pattern-dependent fluorescence lifetimes between 0.82 and 3.46 ns and a moderate-to-high fluorescence quantum yield of 0.07-0.69. The relationships between the solid-state fluorescence properties and the structure of studied compounds based on X-ray analysis were investigated. As a result, the QSPR model was developed using PLSR (Partial Least Squares Regression). Decomposition of the Hirshfeld surfaces (calculated based on the arrangement of molecules in the crystal lattice) revealed the various types of weak intermolecular interactions that occurred in the crystal lattice. The obtained data, in combination with global reactivity descriptors calculated using HOMO and LUMO energy values, were used as explanatory variables. The developed model was characterized by good validation metrics (RMSE CAL = 0.017, RMSE CV = 0.029, R 2 CAL = 0.989, and R 2 CV = 0.968) and indicated that the solid-state fluorescence quantum yield of methoxy- trans -stilbene derivatives was mainly dependent on weak intermolecular C…C contacts corresponding to π-π stacking and C…O/O…C interactions. To a lesser extent and inversely proportional, the fluorescence quantum yield was affected by the interactions of the type O…H/H…O and H…H and the electrophilicity of the molecule.

The new compound 4-hydroxy-1-[(4-nitrophenyl)sulfonyl]pyrrolidine-2-carboxyllic acid was obtained by the reaction of 4-hydroxyproline with 4-nitrobenzenesulfonyl chloride. The compound was characterized using single crystal X-ray diffraction studies. Spectroscopic methods including NMR, FTIR, ES-MS, and UV were employed for further structural analysis of the synthesized compound. The title compound was found to have crystallized in an orthorhombic crystal system with space group P2 1 2 1 2 1 . The S1-N1 bond length of 1.628 (2) Å was a strong indication of the formation of the title compound. The absence of characteristic downfield 1 H NMR peak of pyrrolidine ring and the presence of S-N stretching vibration at 857.82 cm -1 on the FTIR are strong indications for the formation of the sulfonamide. The experimental study was complemented with computations at the B3LYP/6-311G +  + (d,p) level of theory to gain more understanding of interactions in the compound at the molecular level. Noncovalent interaction, Hirsfeld surface analysis and interaction energy calculations were employed in the analysis of the supramolecular architecture of the compound. Predicted ADMET parameters, awarded suitable bioavailability credentials, while the molecular docking study indicated that the compound enchants promising inhibition prospects against dihydropteroate synthase, DNA topoisomerase, and SARS-CoV-2 spike., Graphical Abstract: Herein we present the solid state structure, noncovalent interaction and spectroscopic analysis of a prospective bioactive compound 4-hydroxy-1-[(4-nitrophenyl)sulphonyl]pyrrolidine-2-carboxyllic acid., Supplementary Information: The online version contains supplementary material available at 10.1007/s10870-023-00978-0., Competing Interests: Competing interestsThe authors declare no competing interests., (© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023, Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.)

In the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H 2 L 1 ) and (H 2 L 2 ) and four Ni(II) complexes, [Ni(L 1 )PPh 3 ] (1), [Ni(L 1 )Py] (2), [Ni(L 2 )PPh 3 ] (3), and [Ni(L 2 )Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H 2 L 1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H 2 L 1 confirms the cyclization reaction and formation of the pyrazoline derivative. The results showed square planar geometry to the metal centers, in which dithiocarbazates coordinated by the ONS donor system and a triphenylphosphine or pyridine molecule complete the coordination sphere. Hirshfeld surface analysis by d norm function was investigated and showed π-π stacking interactions upon the molecular packing of H 2 L 1 and non-classical hydrogen bonds for all compounds. Fingerprint plots showed the main interactions attributed to H⋅H C⋅H, O⋅H, Br⋅H, and F⋅H, with contacts contributing between 1.9% and 38.2%. The mass spectrometry data indicated the presence of molecular ions [M + H] + and characteristic fragmentations of the compounds, which indicated the same behavior of the compounds in solution and solid state. Molecular docking simulations were studied to evaluate the properties and interactions of the free dithiocarbazates and their Ni(II) complexes with selected proteins and DNA. These results were supported by in vitro cytotoxicity assays against four cancer cell lines, showing that the synthesized metal complexes display promising biological activity., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Cavalcante, da Mota, de Oliveira, Nascimento, Martins, Pittella-Silva and Gatto.)

The title coordination compound, [Ni(C 6 H 14 N 2 O) 2 (H 2 O) 2 ]Cl 2 , was synthesized by mixing 4-(2-amino-eth-yl)morpholine and nickel chloride in double-distilled water. The asymmetric unit comprises one half of an Ni II cation (located on an inversion centre), one 4-(2-amino-eth-yl)morpholine ligand, one coordinated water mol-ecule and one chloride ion outside the metal coordination sphere. The nickel ion is in a octa-hedral environment of the N 4 O 2 type, coordinating four N atoms from two 4-(2-amino-eth-yl)morpholine ligands and two trans -located O atoms from two water mol-ecules. The morpholine ligand was found disordered over two positions with a site occupancy ratio of 0.708 (8):0.292 (8). The crystal structure is consolidated by N-H⋯Cl, N-H⋯O, C-H⋯Cl and C-H⋯O hydrogen bonds. Hirshfeld surface analysis confirms that van der Waals inter-actions are prevalent in the crystal packing of the synthesized complex., (© Chidambaranathan et al. 2023.)

The crystal structure of the title compound, C 13 H 9 Br 2 N [systematic name: ( E )- N ,1-bis-(4-bromo-phen-yl)methanimine], is a second polymorph (Form II) crystallizing in the ortho-rhom-bic space group Pccn . The first polymorph (Form I) crystallizes in the monoclinic space group P 2 1 / c [Bernstein & Izak (1975 ▸). J. Cryst. Mol. Struct. 5 , 257-266; Marin et al. (2013 ▸). J. Mol. Struct. axis direction and are linked by C-H⋯π inter-actions. The inter-atomic contacts in the crystal for both polymorphs were studied by Hirshfeld surface analysis and have notable differences. The solid-state fluorescence spectrum of Form II shows an emission peak at 1049 , 377-385]. The mol-ecule is disordered about an inversion center situated in the middle of the C=N bond, similar to the situation in the monoclinic polymorph: the C=N bond length is 1.243 (7) Å. In the crystal, mol-ecules stack along the b- axis direction and are linked by C-H⋯π inter-actions. The inter-atomic contacts in the crystal for both polymorphs were studied by Hirshfeld surface analysis and have notable differences. The solid-state fluorescence spectrum of Form II shows an emission peak at ca 469 nm. The two-photon absorption coefficient measured from the open aperture Z -scan technique is 1.3 × 10 -11 m W -1 , hence, Form II shows optical limiting behaviour., (© Subashini et al. 2023.)

The title compound, C 16 H 11 N 3 O 3 , belongs to the family of azo dyes. In the light of a single-crystal X-ray study, it is evident that of the tautomeric forms (azo-hydrazone), the hydrazone form is the predominant form in the solid state, namely, (1 E )-1-[2-(3-nitro-phen-yl)hydrazin-1-yl-idene]-1,2-di-hydro-naphthalen-2-one. The naphthol and benzene fragments attached to the -N=N- moiety adopt the s-trans conformation. Furthermore, the mol-ecules are nearly coplanar, subtending a dihedral angle of 2.63 (5)°. An intra-molecular N-H⋯O hydrogen bond occurs. There are only two types of inter-molecular inter-actions in the crystal structure: strong hydrogen-bonding C-H⋯O inter-actions and π-π stacking inter-actions. The importance of C-H⋯O inter-actions in the mol-ecular packing is reflected by the relatively high contributions (28.5%) made by O⋯H/H⋯O contacts to the Hirshfeld surface., (© Benaouida et al. 2023.)

The nature of intra- and intermolecular non-covalent interactions was studied in four naphthalene derivatives commonly referred to as "proton sponges". Special attention was paid to an intramolecular hydrogen bond present in the protonated form of the compounds. The unsubstituted "proton sponge" served as a reference structure to study the substituent influence on the hydrogen bond (HB) properties. We selected three compounds substituted by methoxy, amino, and nitro groups. The presence of the substituents either retained the parent symmetry or rendered the compounds asymmetric. In order to reveal the non-covalent interaction properties, the Hirshfeld surface (HS) was computed for the crystal structures of the studied compounds. Next, quantum-chemical simulations were performed in vacuo and in the crystalline phase. Car-Parrinello molecular dynamics (CPMD), Path Integral Molecular Dynamics (PIMD), and metadynamics were employed to investigate the time-evolution changes of metric parameters and free energy profile in both phases. Additionally, for selected snapshots obtained from the CPMD trajectories, non-covalent interactions and electronic structure were studied. Quantum theory of atoms in molecules (QTAIM) and the Density Overlap Regions Indicator (DORI) were applied for this purpose. It was found based on Hirshfeld surfaces that, besides intramolecular hydrogen bonds, other non-covalent interactions are present and have a strong impact on the crystal structure organization. The CPMD results obtained in both phases showed frequent proton transfer phenomena. The proton was strongly delocalized in the applied time-scale and temperature, especially in the PIMD framework. The use of metadynamics allowed for tracing the free energy profiles and confirming that the hydrogen bonds present in "proton sponges" are Low-Barrier Hydrogen Bonds (LBHBs). The electronic and topological analysis quantitatively described the temperature dependence and time-evolution changes of the electronic structure. The covalency of the hydrogen bonds was estimated based on QTAIM analysis. It was found that strong hydrogen bonds show greater covalency, which is additionally determined by the proton position in the hydrogen bridge.

In the crystal, mol-ecules of the title compound, C 10 H 8 FIN 2 O 3 S, are connected through C-H⋯N and C-H⋯O hydrogen bonds, I⋯O halogen bonds, π-π stacking inter-actions between the benzene and pyrimidine rings, and edge-to-edge electrostatic inter-actions, as shown by the analysis of the Hirshfeld surface and two-dimensional fingerprint plots, as well as inter-molecular inter-action energies calculated using the electron-density model at the HF/3-21 G level of theory., (© Ganesha et al. 2023.)

The title compound, C 6 H 15 N 2 O + ·C 6 H 2 N 3 O 7 - ·H 2 O, was synthesized via slow evaporation of an aqueous solution of picric acid with the substituted morpholine base and crystallized with one cation (C 6 H 15 N 2 O) + , one anion (C 6 H 2 N 3 O 7 and a water mol-ecule in the asymmetric unit. The morpholine ring in the cation adopts a chair conformation. The structure is stabilized by C-H⋯O, O-H⋯O, O-H⋯N and N-H⋯O hydrogen-bonding inter-actions and π-π stacking. The inter-molecular inter-actions of the synthesized compound were qu-anti-fied by Hirshfeld surface analysis.- and a water mol-ecule in the asymmetric unit. The morpholine ring in the cation adopts a chair conformation. The structure is stabilized by C-H⋯O, O-H⋯O, O-H⋯N and N-H⋯O hydrogen-bonding inter-actions and π-π stacking. The inter-molecular inter-actions of the synthesized compound were qu-anti-fied by Hirshfeld surface analysis., (© Chidambaranathan et al. 2023.)

Novel 6-bromo-imidazo[4,5-b]pyridine derivatives ( 2 - 4 , 5a -1 3a , and 6b , 8b - 13b ) have been synthesized based on a developed systematic approach involving the condensation of 5-Bromo-2,3-diaminopyridine with a suitable aromatic aldehyde in the presence of molecular iodine in water, followed by alkylation reactions using different alkyl dibromide agents. The synthesized compounds were characterized by the NMR spectroscopy technique. The structures of 8a , 9a , 12a, and 11b were confirmed using monocrystalline X-ray crystallography. Theoretical calculations have been carried out using DFT and TD-DFT methods at the B3LYP/6-31G++(d,p) level of theory. Intermolecular contacts between units of 8a , 9a , 12a , and 11b were determined through the Hirshfeld surface analysis. The molecular docking study has been performed to determine the binding affinity of 8a , 9a , 12a, and 11b into the binding site of S. aureus tyrosyl-tRNA synthetase as a target enzyme, and the results revealed that 9a is the most potent compound among the selected compounds with a binding affinity of -8.74 Kcal/mol.Communicated by Ramaswamy H. Sarma.

In this work, a novel crystal, (E)-4-(4-methylbenzyl)-6-styrylpyridazin-3(2H)-one ( E-BSP ) was synthesized via Knoevenagel condensation of benzaldehyde and (E)-6-(4-methoxystyryl)-4,5-dihydropyridazin-3(2H)-one. The molecular structure of E - BSP was confirmed by using FT-IR, 1 H-NMR, 13 C-NMR, UV-vis, ESI-MS, TGA/DTA thermal analyses and single crystal X-ray diffraction. The DFT/B3LYP methods with the 6-311++G(d,p) basis set were used to determine the vibrational modes over the optimized structure. Potential energy distribution (PED) and the VEDA 4 software were used to establish the theoretical mode assignments. The same approach was used to compute the energies of frontier molecular orbitals (HOMO-LUMO), global reactivity descriptors, and molecular electrostatic potential (MEP). Additionally, experimental and computed UV spectral parameters were determined in methanol and the obtained outputs were supported by FMO analysis. Molecular docking and molecular dynamics (MD) simulation analyses of the E-BSP against six proteins obtained from different cancer pathways were carried out. The proteins include; epidermal growth factor receptor (EGFR), Estrogen receptor (ERα), Mammalian target of rapamycin (mTOR), Progesterone receptor (PR) (Breast cancer), Human cyclin-dependent kinase 2 (CDK2) (Colorectal cancer), and Survivin (Squamous cell carcinoma/Non-small cell lung cancer). The results of the analyses showed that the compound had less binding energies ranging between -6.30 to -9.09 kcal/mol and formed stable complexes at the substrate-binding site of the proteins after the 50 ns MD simulation. Therefore, E-BSP was considered a potential inhibitor of different cancer pathways and should be used for the treatment of cancer after experimental validation and clinical trial.Communicated by Ramaswamy H. Sarma.

Background: As an effective strategy to improve the basic properties of drugs, salt formation was less used in the field of pesticides than the medicine field. It is worth trying to improve the inherent shortcomings of cyprodinil (high K ow values; polymorphism) in this way to enhance its practicality., Results: Eight cyprodinil salts (CYP-Salts) were prepared. The properties of CYP-Salts, including solubility in various solvents, polymorphic behavior, soil absorption, photolysis in aquatic water, in vitro fungicidal activity and curative activity, were assessed. It was observed that compared with those of cyprodinil, CYP-Salts had lower soil adsorption, while also having lower log K ow values and could be more easily photodegraded in water. That is, CYP-Salts have lower impacts on water bodies and aquatic organisms than cyprodinil. Three CYP-Salts showed higher in vitro antifungal activities and curative activity. CYP-Salts have enhanced practicality, as they could avoid possible agglomeration caused by recrystallization., Conclusion: Salt forming enhanced the properties of Cyprodinil in many aspects. CYP-Salts may potentially become a better substitute for cyprodinil. This study offers a more economical and effective strategy to prepare better alternatives to existing fungicides. © 2022 Society of Chemical Industry., (© 2022 Society of Chemical Industry.)