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The title compound, C8H11PS, which melts below room temperature, was crystallized at low temperature. The P—S bond length is 1.9623 (5) Å and the major contributors to the Hirshfeld surface are H...H (58.1%), S...H/H...S (13.4%) and C...H/H...C contacts (11.7%).

The crystal structure of the title 2:1 molecular complex between 2-(allylthio)pyridine and 1,2,4,5-tetrafluoro-3,6-diiodobenzene, C6F4I2·2C8H9NS, at 100 K has been determined in the monoclinic space group P21/c. The most noteworthy characteristic of the complex is the halogen bond between iodine and the pyridine ring with a short N...I contact [2.8628 (12) Å]. The Hirshfeld surface analysis shows that the hydrogen...hydrogen contacts dominate the crystal packing with a contribution of 32.1%.

Abstract The pseudo‐natural product (pseudo‐NP) concept aims to combine NP fragments in arrangements that are not accessible through known biosynthetic pathways. The resulting compounds retain the biological relevance of NPs but are not yet linked to bioactivities and may therefore be best evaluated by unbiased screening methods resulting in the identification of unexpected or unprecedented bioactivities. Herein, various NP fragments are combined with a tricyclic core connectivity via interrupted Fischer indole and indole dearomatization reactions to provide a collection of highly three‐dimensional pseudo‐NPs. Target hypothesis generation by morphological profiling via the cell painting assay guides the identification of an unprecedented chemotype for Aurora kinase inhibition with both its relatively highly 3D structure and its physicochemical properties being very different from known inhibitors. Biochemical and cell biological characterization indicate that the phenotype identified by the cell painting assay corresponds to the inhibition of Aurora kinase B.

In the title compound, (2-methylidene-1,2-dihydropyridinium-κN)tris(tetrahydrofuran-κO)lithium, [Li(C6H6N)(C4H8O)3], the lithium ion adopts a distorted LiNO3 tetrahedral coordination geometry and the 2-picolyl anion adopts its enamido form with the lithium ion lying close to the plane of the pyridine ring. A methylene group of one of the thf ligands is disordered over two orientations. In the crystal, a weak C—H...O interaction generates inversion dimers. A Hirshfeld surface analysis shows that H...H contacts dominate the packing (86%) followed by O...H/H...O and C...H/H...C contacts, which contribute 3% and 10.4%, respectively.

The thioether-functionalized 2-azabutadiene (iPrS)2C=C(H)-N=CPh2 L ligates to CdI2 and HgI2 to form the chelate compounds [CdI2{(iPrS)2C=C(H)-N=CPh2] (1) and [HgI2(iPrS)2C=C(H)-N=CPh2] (2). Their crystal structures were solved via X-ray diffraction. Both crystallize in the non-centrosymmetric space groups: monoclinic P21 (1) and orthorhombic P212121 (2), respectively. The closed-shell d10 metal centers are four-coordinated (two iodides and S and N coordinating atoms from the ligand L) in both complexes. The geometrical indexes τ indicate that a highly distorted trigonal pyramidal is adopted for 1 and a seesaw geometry for 2. The comparative nature of metal–ligand bonds is discussed on the basis of metric parameters and of QT-AIM (quantum theory of atoms in molecules) calculations. L was also treated with CuI to obtain the dinuclear species [LCu(μ2-I2)CuL] (3), in which the two Cu(I) centers are linked by a short metal–metal bond. The geometric and electronic properties of 3 are compared with those of 1 and 2.

To extend the existing library of arylidenerhodanines which display a potential biological activity, 3-N-allylrhodanine 1 was condensed under Knoevenagel conditions with p-nitrobenzaldehyde in acetic acid to afford the π-conjugated heterocyclic compound 3-allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 2. Compound 2 was characterized by IR and NMR spectroscopy, and its UV-vis spectrum was compared with that of compound 3-allyl-5-(4-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 3. The molecular structure is ascertained by a single-crystal X-ray diffraction study performed at 100 K.

The olefinic dithioether (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene Z-PyS(CH2CH=CHCH2)SPy (L) was prepared by the treatment of cis-ClCH2CH=CHCH2Cl with in situ generated potassium pyridine-2-thiolate Py-SK and analyzed by IR and NMR spectroscopy. To investigate the chemistry of polynuclear iodobismuthate complexes, two equivalents of BiI3 were reacted with L in the MeOH solution to afford the anionic tetranuclear title compound (C14H15S2N2)2(C9H10SN)2[Bi4I116] with a N-protonated (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene as a counterion. Compound 1 was characterized by IR and UV spectroscopy; the formation of a tetranuclear framework was ascertained by a single-crystal X-ray diffraction study performed at 100 K. Furthermore, an unusual Bi(III)-meditated cyclization of one Z-PyS(CH2CH=CHCH2)SPy ligand occurred, affording the bicyclic pyridinium salt 3-vinyl-2,3-dihydrothiazolo[3,2-a]pyridinium bearing a terminal vinyl group, compensating the second negative charge of the Bi4I164− cluster anion. The SCXRD characterization was completed by a Hirshfeld surface analysis, revealing some secondary interactions occurring in the crystal.

The title compounds Si(C4H5O)4 (1) and Ge(C4H5O)4 (2) are dihydrofuryl compounds of silicon and germanium and are useful building blocks for the functionalization of these elements. Both structures crystallize in space group P21/n in the monoclinic crystal system with two molecules in the asymmetric unit: the Si and Ge atoms adopt slightly distorted tetrahedral geometries, while the C4H5O moieties exhibit shallow envelope conformations. Through a Hirshfeld surface analysis of the structures, interactions within the crystal packing could be elucidated: compound 1 features a polymeric chain in the (101) plane via C—H...O hydrogen bonds whereas in 2 C—H...O hydrogen bonds create a polymeric chain in the (010) plane.

The title complex, [PtI2(C7H8I2)2], represents a further example of a square-planar PtII–dithioether complex. It crystallizes in the monoclinic space group P21/c. Additional Hirshfeld analyses indicate a C—H...π interaction along the [010] axis to be the most important packing factor.

Trimethyl({tris[(phenylsulfanyl)methyl]silyl}methoxy)silane (3), C26H32OS3Si, is a new ligand for transition-metal coordination chemistry derived from 3-bromo-2,2-bis(bromomethyl)propan-1-ol (1), C5H9Br3O, through silylation and following exchange of bromine groups with NaSPh. Silylated thioether ligand 3 crystallizes in the centrosymmetric space group C2/c. Bromomethylalcohol 1 crystallizes in the space group P\overline{1} in the triclinic crystal system with four molecules in the asymmetric unit. Analysis of the Hirshfeld surface shows structure-defining interactions for bromomethylalcohol 1, resulting in intermolecular hydrogen bonds between the hydroxyl groups along the a-axis direction.

N-{[Diphenyl(vinyl)silyl]methyl}-2-methylpropan-2-amine, C19H25NSi, is a newly synthesized secondary aminomethylsilane that can be used, for example, to study carbolithiation reactions of vinylsilanes. Because the neutral compound did not crystallize well, the hydrochloride salt, C19H26NSi+·Cl−, was formed, in which the two chloride ions in the asymmetric unit have crystallographic \overline{1} site symmetry. An unusually long Si—C bond of 1.9117 (10) Å is observed in the cation, which may be ascribed to electronic effects due to the β N+ species. In the crystal, the cations and anions are linked by N—H...Cl hydrogen bonds to generate [001] chains. To further investigate the intermolecular interactions, a Hirshfeld surface analysis was performed, which showed that H...H, C...H/H...C and H...Cl/Cl...H contacts contribute 70.4, 20.0 and 8.3%, respectively.

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands toward coinage metals, CuBr was reacted with one equivalent of MeOC(=S)N(H)Ph L in MeCN solution to afford the 1D-polymeric title compound [{Cu(μ2-Br)2Cu}{μ2-MeOC(=S)N(H)Ph}2]n CP1. Compound 1 was characterized by IR spectroscopy and an elemental analysis. The formation of a polymeric 1D ribbon built upon μ2-bridging bromido and thione ligands via the C=S bond was ascertained by a single-crystal X-ray diffraction study performed at 100 K. In the presence of PAr3 (Ar = Ph, p-Tol), the polymer chain was broken to yield the mononuclear complexes [(Ar3P)2Cu{MeOC(=S)N(H)Ph}Br] C1 and C2.

In a sustained search for novel potential drug candidates with multispectrum therapeutic application, a series of novel spirooxindoles was designed and synthesized via regioselective three-component reaction between isatin derivatives, 2-phenylglycine and diverse arylidene-imidazolidine-2,4-diones (Hydantoins). The suggested stereochemistry was ascertained by an X-ray diffraction study and NMR spectroscopy. The resulting tetracyclic heterocycles were screened for their in vitro and in vivo anti-inflammatory and analgesic activity and for their in vitro antimicrobial potency. In vitro antibacterial screening revealed that several derivatives exhibited remarkable growth inhibition against different targeted microorganisms. All tested compounds showed excellent activity against the Micrococccus luteus strain (93.75 µg/mL ≤ MIC ≤ 375 µg/mL) as compared to the reference drug tetracycline (MIC = 500 µg/mL). Compound 4e bearing a p-chlorophenyl group on the pyrrolidine ring exhibited the greatest antifungal potential toward Candida albicans and Candida krusei (MIC values of 23.43 µg/mL and 46.87 µg/mL, respectively) as compared to Amphotericin B (MIC = 31.25 and 62.50 µg/mL, respectively). The target compounds were also tested in vitro against the lipoxygenase-5 (LOX-5) enzyme. Compounds 4i and 4l showed significant inhibitory activity with IC50 = 1.09 mg/mL and IC50 = 1.01 mg/mL, respectively, more potent than the parent drug, diclofenac sodium (IC50 = 1.19 mg/mL). In addition, in vivo evaluation of anti-inflammatory and analgesic activity of these spirooxindoles were assessed through carrageenan-induced paw edema and acetic acid-induced writhing assays, respectively, revealing promising results. In silico molecular docking and predictive ADMET studies for the more active spirocompounds were also carried out.

The title molecular salt, C17H30NSi+·C2H5O4S−, belongs to the class of a-aminosilanes and was synthesized by the alkylation of 1-[(benzyldimethylsilyl)methyl]piperidine using diethyl sulfate. This achiral salt crystallizes in the chiral space group P21. One of the Si—C bonds in the cation is unusually long [1.9075 (12) Å], which correlates with the adjacent quaternary N+ atom and was verified by quantum chemical calculations. In the crystal, the components are linked by weak C—H...O hydrogen bonds: a Hirshfeld surface analysis was performed to further investigate these intermolecular interactions and their effects on the crystal packing.

The title compound C9H14N+·Cl−, (1), can be synthesized starting from (S)-N-methyl-1-phenylethan-1-amine (2). Compound 2 upon addition of HCl·Et2O leads to crystallization of compound 1 as colorless blocks. The configuration of compound 1 is stable as well as preserved in space group P212121. Ammonium chlorides, like the title compound, are often observed as undesirable by-products in aminosilylation of chlorosilanes. Additionally, these by-products are usually soluble in selected organic solvents, which require difficult separation steps. Therefore, detailed studies on structural features and intermolecular interactions performed by Hirshfeld atom refinement (HAR) using NoSpherA2 [Kleemiss et al. (2021). Chem. Sci. 12, 1675–1692] and Hirshfeld surface analysis were used to address structural issues on that separation problem.

The title compounds, C10H16O2Si (1) and C17H18OSi (2), are classified as dihydrofurylsilanes, which show great potential as building blocks for various functionalized silanes. They both crystallize in the space group P\overline{1} in the triclinic crystal system. Analyses of the Hirshfeld surfaces show packing-determining interactions for both compounds, resulting in a polymeric chain along the [011] for silane 1 and a layered-interconnected structure along the b-axis direction for silane 2.

The title compound N,N,N′,N′-tetramethylethanediamine, C6H16N2, is a bidentate amine ligand commonly used in organolithium chemistry for deaggregation. Crystals were grown at 243 K from n-pentane solution. The complete molecule is generated by a crystallographic center of symmetry and the conformation of the diamine is antiperiplanar. To investigate the intermolecular interactions, a Hirshfeld surface analysis was performed. It showed that H...H (van der Waals) interactions dominate with a contact percentage of 92.3%.

The reaction of [Co2(CO)8] with an equimolar amount of the internal alkyne N-(2-butynyl)phthalimide (1-Phthalimido-2-butyne) 1 in heptane solution yields the title compound [Co2(CO)6(µ-phthalimidoCH2C≡CMe)] 2. Compound 2 has been characterized using IR, 1H and 13C NMR spectroscopy; the tetrahedrane-type cluster framework has been ascertained using a single-crystal X-ray diffraction study performed at 100 K.

In toluene solution, the reaction of [Co2(CO)8] with an equimolar amount of [P(OPh)3] yields first [Co2(CO)7{P(OPh)3}] 1. Following heating of 1, an alternative synthetic access to the tetranuclear cluster [{Co4(μ2-CO)3(CO)8{P(OPh)3}] 2 is provided in a condensation reaction. Compound 2 has been characterized by IR and 31P NMR spectroscopy. The tetranuclear cluster framework has been ascertained by a single-crystal X-ray diffraction study performed at 100 K.

The first title compound, C29H24S2, L1, represents an example of an anthracene-based functionalized dithioether, which may be useful as a potential chelating or terminal ligand for coordination chemistry. This dithioacetal L1 crystallizes in the monoclinic space group P21/c. The phenyl rings of the benzyl groups and that of the anthracene unit form dihedral angles of 49.21 (4) and 58.79 (5)° and the crystal structure displays short C–H...π contacts. Surprisingly, when attempting to coordinate L1 to [PdCl2(PhCN)2], instead of the targeted chelate complex [PdCl2(κ2-L1)], a cleavage reaction leads to the formation of the centrosymmetric hexanuclear cyclic cluster of composition [Pd6(μ2-SCH2Ph)12] Pd6, or [Pd6(C7H7S)12]·C14H8O2. This tiara-shaped hexamer crystallizing in the triclinic space group P\overline{1} consists of six approximately square planar Pd(II)S4 centers, which are interconnected through twelve μ2-bridging benzyl thiolate groups. The Pd...Pd contacts range from 3.0892 (2) to 3.1609 (2) Å and can be considered as weakly bonding. The unit cell of Pd6 contains also a co-crystallized anthracene-9,10-dione molecule.

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, BiI3 was reacted with two equivalents of MeOC(=S)N(H)Ph in MeCN solution to afford the dinuclear title compound complexes [{I2Bi(μ2-I)2BiI2}{κ1-MeOC(=S)N(H)Ph}4] 1. Compound 1 was characterized by IR, UV and NMR spectroscopy, the formation of a dinuclear framework is ascertained by a single-crystal X-ray diffraction study performed at 100 K.

Natural products inspire the development of pseudo-natural products through combinations of fragments of compound classes that are chemically and biologically distinct. Here, the authors report a library of 244 pseudo-natural products, evaluate them in the cell painting essays and identify the phenotypic role of individual fragments.

The title compounds, C13H18O3Si (1) and C18H20O3Si (2), represent functionalizable dihydrofuranylsilanes, which permit substitution by a variety of nucleophiles. The crystal structures of 1 and 2 display weak intermolecular C—H...O hydrogen-bonding interactions (quantified by Hirshfeld surface analysis), leading to a two-dimensional supramolecular network for 1 and a one-dimensional supramolecular network for 2. The crystal structures of 1 and 2 were refined both on the basis of the independent atom model (IAM) and the Hirshfeld atom refinement (HAR) approach, and the results are comparatively discussed.

The title compound [(N,N-dimethylamino)methyl]ferrocene, [Fe(C5H5)(C8H12N)], (1), is an interesting starting material for the synthesis of planar chiral 1,2-disubstituted ferrocenes, as demonstrated by the preparation of (Rp,Rp)-bis{2-[(dimethylamino)methyl]ferrocenyl}dimethylsilane, [Fe2(C5H5)2(C18H18N2Si)], (2), from the lithiated derivative of 1. The configuration of the lithium compound is unchanged after the substitution reaction and the chirality is preserved in space group P212121. In both compounds, the Cp rings adopt eclipsed conformations. Hirshfeld surface analysis was used to investigate the intermolecular interactions, and showed that H...H (van der Waals) interactions dominate in both structures with contact percentages of 83.9 and 88.4% for 1 and 2, respectively.

The complete molecule of the hexametallic title complex, namely, tetrabromidotetra-μ-hydroxido-hexakis[μ-2-methyl-3-(pyrrolidin-1-yl)propan-2-olato]hexazinc(II) acetone disolvate, [Zn6Br4(C9H18NO)4(OH)4]·2C3H6O2, is generated by a crystallographic centre of symmetry. Two of the unique zinc atoms adopt distorted ZnO2NBr tetrahedral coordination geometries and the other adopts a ZnO3N tetrahedral arrangement. Both unique alkoxide ligands are N,O-chelating and both hydroxide ions are μ2 bridging. The crystal structure displays an O—H...O hydrogen bond between a μ2-OH group and an acetone solvent molecule. The Hirshfeld surface has been calculated and is described.

The title compound, [FePt(C19H18OS2)(C18H15P)(C25H22P2)(CO)2], 1, [(OC)2Fe(μ-dppm)(μ-C(=O)C(CH2SC6H4Me-4)=CCH2SC6H4Me-4)Pt(PPh3)], represents the first example of a diphosphane-bridged heterobimetallic Fe—Pt dimetallacyclopentenone complex resulting from a bimetallic activation of metal-coordinated carbonyl ligand with an internal alkyne, namely 1,4-bis(p-tolylthio)but-2-yne. The bridging μ2-C(=O)C(CH2SC6H4Me-4)=CCH2SC6H4Me-4 unit (stemming from a carbon–carbon coupling reaction between CO and the triple bond of the alkyne dithioether) forms a five-membered dimetallacyclopentenone ring, in which the C=C bond is π-coordinated to the Fe center. The latter is connected to the Pt center through a short metal–metal bond of 2.5697 (6) Å.

The title compounds, hexakis[μ3-2-(dimethylamino)ethanolato]hexa-μ2-isopropanolato-μ4-oxido-tetradecalithium(I), [Li7(i-PrO)3(C4H10NO)3]2O (1), and {3-[(2-methoxyethyl)(methyl)amino]-1,1-dimethylpropanolato}diisopropanolsodium(I), [Na(i-PrOH)2(C8H18NO2)] (2), were crystallized in the presence of 2-propanol (i-PrOH, C3H7OH). The structure 1 has monoclinic symmetry (C2/c) and the asymmetric unit contains half of the compound. Title compound 2 has triclinic symmetry (P\overline{1}) and the asymmetric unit is half of an inversion-symmetric aggregate. Both compounds consist of an alkali metal, an aminoalkoxide and a 2-propanol compound. Furthermore, the dimeric sodium aggregate 2 is build up by hydrogen bonding through the 2-propanol and the alkoxides. Compound 1 does not exhibit hydrogen bonding, due to the fact that the 2-propanol is deprotonated. In compound 1, benzene appeared as co-crystallate, but was suppressed by solvent masking because of strong disorder. The formula mass and density do not take account of the solvent.

The title compound, C22H22O2S2, 1, represents an example of an ortho-vanillin-based functionalized dithioether, which could be useful as a potential chelating ligand or bridging ligand for coordination chemistry. This dithioacetal 1 crystallizes in the orthorhombic space group Pbca. The phenyl rings of the benzyl groups and that of the vanillin unit form dihedral angles of 35.38 (6) and 79.77 (6)°, respectively. The crystal structure, recorded at 100 K, displays both weak intramolecular O—H...O and intermolecular O—H...S hydrogen bonding.

The crystal structure of the title compound, C10H13N·3H2O, a heterocyclic amine, was determined in the presence of water. The compound co-crystallizes with three water molecules in the asymmetric unit, which leads to the formation of hydrogen bonding in the crystal.

The polymeric title compound, [Cu2(C2H3N)2(C3H6S2)2](PF6)2, represents an example of a one-dimensional coordination polymer resulting from the reaction of [Cu(MeCN)4][PF6] with 1,3-dithiolane. The cationic one-dimensional ribbon consists of two copper(I) centers each ligated by one acetonitrile molecule and interconnected through two bridging 1,3-dithiolane ligands. One S-donor site of each ligand is κ1-bound to Cu, whereas the second S atom acts as a four-electron donor, bridging two Cu atoms in a κ4-bonding mode. The positive charge of each copper cation is compensated for by a hexafluoridophosphate counter-ion. In the crystal, the polymer chains are linked by a series of C—H...F hydrogen bonds, forming a supramolecular framework.

The title compound, [FePt(C12H12O)(C18H15P)(C25H22P2)(CO)2]·2C7H8·CH2Cl2 or [(OC)2Fe(μ-dppm)(μ-C(=O)C(2,4,5-C6H2Me3)=CH)Pt(PPh3)], represents an example of a diphosphane-bridged heterobimetallic dimetallacyclopentenone complex resulting from a bimetallic activation of 1-ethynyl-2,4,5-trimethylbenzene and a metal-coordinated carbonyl ligand. The bridging μ2-C(=O)C(2,4,5-C6H2Me3)=CH unit (stemming from a carbon–carbon coupling reaction between CO and the terminal alkyne) forms a five-membered dimetallacyclopentenone ring, in which the C=C bond is π-coordinated to the Fe centre. The latter is connected to the Pt centre through a short metal–metal bond of 2.5770 (5) Å. In the crystal, the complex is solvated by one dichloromethane and two toluene molecules.

Abstract Chemical and biological limitations in bioactive compound design based on natural product (NP) structure can be overcome by the combination of NP‐derived fragments in unprecedented arrangements to afford “pseudo‐natural products” (pseudo‐NPs). A new pseudo‐NP design principle is described, i.e., the combination of NP‐fragments by transformations that are not part of current biosynthesis pathways. A collection of indofulvin pseudo‐NPs is obtained from 2‐hydroxyethyl‐indoles and ketones derived from the fragment‐sized NP griseofulvin by means of an iso‐oxa‐Pictet‐Spengler reaction. Cheminformatic analysis indicates that the indofulvins reside in an area of chemical space sparsely covered by NPs, drugs, and drug‐like compounds and they may combine favorable properties of these compound classes. Biological evaluation of the compound collection in different cell‐based assays and the unbiased high content cell painting assay reveal that the indofulvins define a new autophagy inhibitor chemotype that targets mitochondrial respiration.

Despite the effectiveness of COVID-19 vaccines, there is still an urgent need for discovering new anti-viral drugs to address the awful spread and transmission of the rapidly modifiable virus. In this study, the ability of a small library of enantiomerically pure spirooxindolopyrrolidine-grafted piperidones to inhibit the main protease of SARS-CoV-2 (Mpro) is evaluated. These spiroheterocycles were synthesized by 1,3-dipolar cycloaddition of various stabilized azomethine ylides with chiral dipolarophiles derived from N-[(S)-(-)-methylbenzyl]-4-piperidone. The absolute configuration of contiguous carbons was confirmed by a single crystal X-ray diffraction analysis. The binding of these compounds to SARS-CoV-2 Mpro was investigated using molecular docking and molecular dynamics simulation. Three compounds 4a, 4b and 4e exhibited stable binding modes interacting with the key subsites of the substrate-binding pocket of SARS-CoV-2 Mpro. The synthesized compounds represent potential leads for the development of novel inhibitors of SARS-CoV-2 main protease protein for COVID-19 treatment.

The presence of metal centers with often highly conserved coordination environments is crucial for roughly half of all proteins, having structural, regulatory, or enzymatic function. To understand and mimic the function of metallo-enzymes, bioinorganic chemists pursue the challenge of synthesizing model compounds with well-defined, often heteroleptic metal sites. Recently, we reported the design of tailored homoleptic coordination environments for various transition metal cations based on unimolecular DNA G-quadruplex structures, templating the regioselective positioning of imidazole ligandosides LI. Here, we expand this modular system to more complex, heteroleptic coordination environments by combining LI with a new benzoate ligandoside LB within the same oligonucleotide. The modifications still allow the correct folding of parallel tetramolecular and antiparallel unimolecular G-quadruplexes. Interestingly, the incorporation of LB results in strong destabilization expressed in lower thermal denaturation temperatures Tm. While no transition metal cations could be bound by G-quadruplexes containing only LB, heteroleptic derivatives containing both LI and LB were found to complex CuII, NiII, and ZnII. Especially in case of CuII we found strong stabilizations of up to ΔTm = +34°C. The here shown system represents an important step toward the design of more complex coordination environments inside DNA scaffolds, promising to culminate in the preparation of functional metallo-DNAzymes.

A novel series of 14 spiropyrrolidines bearing thiochroman-4-one/chroman-4-one, and oxindole/acenaphthylene-1,2-dione moieties were synthesized and characterized by spectroscopic techniques, as well as by three X-ray diffraction studies, corroborating the stereochemistry. Quantum chemical calculations studies, using the DFT approach, were performed to rationalize the stereochemical outcome. These N-heterocycles were evaluated for their antibacterial and antifungal activities against some pathogenic organisms. Several compounds displayed moderate to excellent activity towards the screened microbe strains in the study compared to Amoxicillin (AMX), Ampicillin (AMP), and Amphotericin B. Furthermore, a structural activity relationship (SAR) was established considering the synthesized compounds. Pharmacokinetic studies reveal that these derivatives exhibit an acceptable predictive ADMET profile (Absorption, Distribution, Metabolism, Excretion and Toxicity) and good drug-likeness.

Synthetic methods that efficiently construct structurally diverse molecular scaffolds are attractive routes to diversely bioactive molecules. Here the authors report a method whereby common starting materials are converted to structurally and functionally diverse products by changing the catalyst ligand.

The title compounds, [Sn3(CH3)9(OH)2(H2O)2][Sn(CH3)3(CHO2)2] (1) and [Sn3(CH3)9(OH)2]Cl·H2O (2), are partially condensed products of hydrolysed trimethyltin chloride. In the structures of 1 and 2, short cationic tristannatoxanes (C9H29O2Sn3) are bridged by a diformatotrimethyltin anion or a chloride anion, respectively. Hydrogen bridges are present and supposedly stabilize these structures against further polymerization to the known polymeric trimethyltin hydroxide. Especially noteworthy is that the formate present in this structure was formed from atmospheric CO2.

A novel one-pot [3+2]-cycloaddition reaction of (E)-3-arylidene-1-phenyl-succinimides, cyclic 1,2-diketones (isatin, 5-chloro-isatin and acenaphtenequinone), and diverse α-aminoacids such as 2-phenylglycine or sarcosine is reported. The reaction provides succinimide-substituted dispiropyrrolidine derivatives with high regio- and diastereoselectivities under mild reaction conditions. The stereochemistry of these N-heterocycles has been confirmed by four X-ray diffraction studies. Several synthetized compounds show higher inhibition on acetylcholinesterase (AChE) than butyrylcholinesterase (BChE). Of the 17 synthesized compounds tested, five exhibit good AChE inhibition with IC50 of 11.42 to 22.21 µM. A molecular docking study has also been undertaken for compound 4n possessing the most potent AChE inhibitory activity, disclosing its binding to the peripheral anionic site of AChE enzymes.

The title compound, C18H22, is a coupling product of two metallated mesitylene molecules. The dihedral angle between the aromatic rings is 11.10 (5)° and the Car—Cm—Cm—Car (ar = aromatic and m = methylene) torsion angle is 179.60 (14)°. No directional interactions beyond normal van der Waals contacts could be identified in the crystal. To our best knowledge, it is the first known coupling product of metallated mesitylene.

The title compound, C15H18O4, which crystallizes with two molecules in the asymmetric unit, was obtained in the course of the total synthesis of curvicollides A–C and fusaequisin A. It features the relative configuration of the Western aldol part of the natural products. In the crystal, molecules are linked by C—H...O hydrogen bonds.

The title compound, [Ge(CH3)3(C7H5O2)], was obtained as a by-product in the synthesis of the corresponding aldehyde. Two slightly different molecules are present in the asymmetric unit. In both molecules, the geometry of the aromatic ring plane is distorted by varying intensities. Additionally, the Ge atoms deviate from the mean aromatic ring planes. Whereas the distance of the Ge atom to the ring plane is only 0.101 (4) Å in the first molecule, this distance is increased to 0.210 (4) Å in the second. In the crystal structure, centrosymmetric O—H...O hydrogen-bonded dimers are formed. The title compound is isostructural with the Si analogue [Haberecht et al. (2004). Acta Cryst. E60, o329–0330].

The title compound, C11H20O3, was obtained in the course of the total syntheses of curvicollides A–C and features the same relative configuration for the central lactone moiety as that reported for the latter compounds. In the crystal, molecules are linked via O—H...O hydrogen bonds: all of the OH groups act as donors as well as acceptors for these bonds, hence each molecule is bound to six surrounding molecules and a three-dimensional network is formed. The absolute structure was confirmed by refinement of the Flack parameter.

The title compound, C17H24N2O3S, was synthesized in order to determine the relative configuration of the corresponding β-keto aldehyde. In the U-shaped molecule, the five-membered ring approximates an envelope, with the methylene C atom adjacent to the quaternary C atom being the flap, and the methyl and isopropyl substituents lying to the same side of the ring. The dihedral angles between the four nearly coplanar atoms of the five-membered ring and the flap and the aromatic ring are 35.74 (15) and 55.72 (9)°, respectively. The bond angles around the S atom are in the range from 103.26 (12) to 120.65 (14)°. In the crystal, molecules are linked via N—H...O hydrogen bonds, forming a chain along the a axis.

Silyl-substituted pyrrolidines have gained increased interest for the design of new catalyst scaffolds. The molecular structures of four enantiomerically-pure 2-silylpyrrolidinium salts are reported. The perchlorate salts of (S)-2-(triphenylsilyl)pyrrolidine [(S)-1·HClO4] and (S)-2-(methyldiphenylsilyl)pyrrolidine [(S)-2·HClO4], the trifluoroacetate (S)-2·TFA, and the methanol-including hydrochloride (S)-1·HCl·MeOH were elucidated by X-ray crystallography and discussed in terms of hydrogen-bond interactions.

The title compound, [Cu2I2(CH3CN)4], exhibits a centrosymmetric Cu2I2 core [Cu...Cu distance = 2.7482 (11) Å], the CuI atoms of which are further coordinated by four molecules of acetonitrile. The CuI atom has an overall distorted tetrahedral coordination environment evidenced by L—Cu—L angles (L = N or I) ranging from 100.47 (10) to 117.06 (2)°. The coordination geometries of the acetonitrile ligands deviate slightly from linearity as shown by Cu—N—C angles of 167.0 (2) and 172.7 (2)°. In the crystal, there are no significant hydrogen-bonding interactions present, so the crystal packing seems to be formed predominantly by van der Waals forces.

The title compound, [Cu2I2(C11H22N2)2], crystallizes as a symmetric dimer with one quarter of the molecule in the asymmetric unit. The copper(I) atom, the iodine atom and the central methylene C atom of the di(piperidin-1-yl)methane ligand lie on a mirror plane and the complete molecule exhibits point group symmetry 2/m. To the best of our knowledge it is the first diamine copper(I) complex containing a four-membered chelate ring. Compared to other diamine copper(I) iodide dimers, the title compound has a short Cu...Cu distance of 2.5137 (11) Å, but a long Cu—N bond length of 2.213 (3) Å. The I—Cu—I angle [121.84 (2)°] is large, and the N—Cu—N angle = 66.61 (13)° is the smallest one found for copper(I) diamine complexes. As a result of the four-membered ring, the ligands around the copper(I) atom have an extremely distorted tetrahedral arrangement. In the crystal, there are no significant intermolecular interactions present.

The title compound, C20H29NSi+·Br−, contains a chiral silicon atom but crystallizes as a racemate. The C—Si—C bond angles in the range of 103.64 (8)–111.59 (9)° are usual for tetrahedral geometry. The piperidine ring shows a regular chair conformation with an equatorially positioned exocyclic N—C bond. In the crystal, there is a hydrogen bond between the ammonium cation and the bromide anion. The crystal packing shows the dominant intermolecular interaction to be the electrostatic attraction between the ammonium cation and the bromide anion.

In the title compound, {[(dimethylamino)methyl]dimethylamine}trihydridoboron, C5H17BN2, the tetrahedral geometry of the N—C—N unit is slightly disorted. As a result of the bulky amine substituents, a wider N—C—N angle of 113.6 (1)° is observed. The bond lengths between the N atom and methyl groups are slighly elongated to 1.481 (2) and 1.482 (2) Å at the borated N atom, whereas the distances between the other N atom and its methyl groups are only 1.461 (2) and 1.462 (2) Å. The studied crystal was twinned. The twin data refinement was subsequently carried out with a scale factor of 0.263 (1). The two lattices of the twin domains were rotated by 179.84°.

The title hydrate, C17H28O2·H2O, was synthesized in order to determine the relative configuration of the tetracyclic framework. The fused 5,6,7-tricarbocyclic core exhibits an entire cis-annulation, featuring a 1,4-cis-relation of the angular methyl groups in the six-membered ring. The oxa bridge of the epoxycycloheptane moiety is oriented towards the concave face of the boat-shaped molecule, whereas the angular methyl groups are directed towards the convex face. The asymmetric unit of the crystal contains two nearly identical formula units, which are related via a pseudo-centre of symmetry. The structure could be solved in the space groups I-4 and I41/a. The refinement in the acentric space group, however, gave significantly better results and these are used in this paper. O—H...O hydrogen bonds are observed between the organic molecules, between the organic molecules and the water molecules, and between the water molecules, forming a chain along the c-axis direction.