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Rhodium-catalyzed [2+2+2] cycloaddition of carbon disulfide to o,N-dialkynyltosylanilines gives two isomeric indolothiopyranthiones, a violet and a red isomer. This is the first crystal structure of a red isomer, which crystallizes with one solvent molecule of dichloromethane in the asymmetric unit, C24H17NO2S3·CH2Cl2. In the extended structure, centrosymmetric pairs of the planar annulated system are arranged in strands and solvent molecules fill the space between the strands.

The Cadogan reaction of 2-aryl-3-nitropyridines leads to δ-carbolines. The title compound is a side product in this reaction, generated via a ring opening of a nitrene and cyclization. A crystal structure analysis gives an enormous unit cell.

The nearly planar molecule of the title compound, C70H112N6O6, is centrosymmetric with two all-s-trans chains, the other two chains have an s-cis unit starting with the oxygen atoms. The chains are interdigitated in the packing.

The crystal of the title compound, C10H16Br2O2S, is formed from layers built from centrosymmetric pairs of molecules. The molecule adopts a twist conformation with the carbon atoms next to sulfur above or below the mean plane.

Reaction of diphenylmethanol (4) with n-butyllithium and subsequent treatment with selenium resulted in 12H-dibenzo[d,g][1,2,3]triselenocin-12-ol (5) comprising a novel heterocyclic ring system. The title compound 5 was analyzed by 1H-NMR, 13C-NMR and HPLC. Additionally, the structure of 5 was confirmed by single crystal X-ray diffraction.

The synthesis and spectroscopic investigation of an acidochromic phenylenevinylene dye with two ferrocene groups is presented.

The title compound (S)-3-(3-((7-ethynyl-9H-pyrimido[4,5-b]indol-4-yl)amino)piperidin-1-yl)propanenitrile (2) was synthesized in five steps, starting from 4-chloro-7-iodo-9H-pyrimido[4,5-b]indole (3), and was characterized by 1H-NMR, 13C-NMR, MS and HPLC. Moreover, its structure was confirmed by single crystal X-ray diffraction. Pyrimido[4,5-b]indole 2 demonstrated an IC50 value of 2.24 µM in a NanoBRETTM TE intracellular glycogen synthase kinase-3β assay.

Abstract Exploration of novel biaryls consisting of two polycyclic aromatic hydrocarbon (PAH) units can be an important strategy toward further developments of organic materials with unique properties. In this study, 5,5′‐bibenzo[rst]pentaphene (BBPP) with two benzo[rst]pentaphene (BPP) units is synthesized in an efficient and versatile approach, and its structure is unambiguously elucidated by X‐ray crystallography. BBPP exhibits axial chirality, and the (M)‐ and (P)‐enantiomers are resolved by chiral high‐performance liquid chromatography and studied by circular dichroism spectroscopy. These enantiomers have a relatively high isomerization barrier of 43.6 kcal mol−1 calculated by density functional theory. The monomer BPP and dimer BBPP are characterized by UV‐vis absorption and fluorescence spectroscopy, cyclic voltammetry, and femtosecond transient absorption spectroscopy. The results indicate that both BPP and BBPP fluoresce from a formally dark S1 electronic state that is enabled by Herzberg–Teller intensity borrowing from a neighboring bright S2 state. While BPP exhibits a relatively low photoluminescence quantum yield (PLQY), BBPP exhibits a significantly enhanced PLQY due to a greater S2 intensity borrowing. Moreover, symmetry‐breaking charge transfer in BBPP is demonstrated by spectroscopic investigations in solvents of different polarity. This suggests high potential for singlet fission in such π‐extended biaryls through appropriate molecular design.

Potassium ion sensors are important for the study of concentration profiles in tissues. The synthesis of a cryptand suited for potassium ions and the crystal structure of it with a chelated sodium ion are presented.

The asymmetric unit of the title compound, C42H24, contains two almost identical molecules. The molecules have approximate D2 symmetry. They show a largely twisted double bond, the molecular halves enclosing dihedral angles of 62.86 (4) and 61.22 (3)°. The crystal studied was twinned by non-merohedry.

The title compound, C12H17I2O3P, was prepared in three steps from p-xylene. Heterodimers between nearly identical molecules are connected via three hydrogen bonds from benzylic and ester methylene groups to phosphonate. The dimers form chains along the a-axis direction, stabilized by C—H...O bridges.

The centrosymmetric title compound, C22H36N2O2, was prepared in five steps from diethyl succinate. The dipropylamino groups are almost orthogonal to the central phenylenedimethanol ring [dihedral angle = 87.62 (9)°]. In the crystal, the molecules are connected by O—H...N hydrogen bonds, forming (101) layers separated by the propyl chains.

Abstract A scalable, dehydrogenative, and electrochemical synthesis of novel highly fluorinated orthoesters is reported. This protocol provides easy and direct access to a wide variety of derivatives, using a very simple electrolysis setup. These compounds are surprisingly robust towards base and acid with an unusual high lipophilicity, making them interesting motifs for potentially active compounds in medicinal chemistry or agro applications. The use of electricity enables a safe and environmentally benign chemical transformation as only electrons serve as oxidants.

The title compound, C19H22FN5O, has been synthesized as an inhibitor of glycogen synthase kinase-3β. Two molecules interact via two N—H...N hydrogen bonds, forming centrosymmetric dimers.

Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2).

The title compound, C12H20N2OSe, crystallizes in strands of enantiomeric molecules connected via O—H...N hydrogen bonds. There are only slight deviations from an ideal gauche conformation in the decamethylene chain, indicating just a little strain.

In the title compound, a cyclooctene ring in a twist-boat conformation and a dioxolane ring with a distorted envelope conformation are annulated in a trans configuration. Alternating strands of single enantiomers build up the crystal. Within the strands, the molecules are connected by weak C—H...O hydrogen bonds.

The centrosymmetric crystal structure of the title compound, C11H16N2Se, is built up from alternating strands of (R,R)- and (S,S)-enantiomers. These strands, which propagate along the c-axis direction, are composed of homochiral molecules related to each other by twofold screw axes. The shape of the molecule is an almost planar unit around the selenadiazole ring with a hexamethylene chain as an arched handle.

The title molecule, C19H24O5, is built by annulation of a half-chair cyclohexenone and a twist-cyclohexenone to a flat 4-H-pyrane boat. In the crystal, molecules are connected via van der Waals interactions and C—H...O hydrogen bonds.

Irradiation of 1-(1-benzocyclobutenylidene)benzocyclobutene gives indenoindene and its head-to-head photodimer nonacyclo[9.7.7.72,10.01,11.02,10.03,8.012,17.019,24.026,31]dotriaconta-3,5,7,12,14,16,19,21,23,26,28,30-dodecaene, C32H24. The molecule is built from four essentially planar indane units attached to an elongated cyclobutane ring. In the crystal, C—H...π interactions connect molecules into layers parallel to the bc plane.

The molecule of the title compound, C30H22N4, exhibits inversion symmetry adopting the shape of a St Andrew's Cross. It shows dihedral angles between adjacent aryl units of around 50° whereas torsion angles of ca 10° are found along the arylene vinylene path.

Triazolopyridines are a family of compounds that, owing to their biological activity, have many pharmaceutical applications. In this study, 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine and 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine were synthesized by using the chlorinated agent NCS for hydrazones under very mild conditions. The characterization of these compounds was achieved by 1H NMR, 13C NMR, FTIR, MS and X-ray diffraction. The compound 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine was crystallized in the monoclinic space group P 21/c with a = 15.1413(12), b = 6.9179(4), c = 13.0938(8) Å, β = 105.102(6)°, V = 1324.16(16)Å3, Z = 4, and R = 0.0337. Also compound 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine was crystallized in the monoclinic space group P 21/c with a = 14.3213(11), b = 6.9452(4) (4), c = 12.6860(8)Å, β = 100.265(6)°, V = 1241.62(14)Å3, Z = 4, and R = 0.0561.

Three novel pyrazolo-[4,3-e][1,2,4]triazolopyrimidine derivatives (1, 2, and 3) were designed, synthesized, and evaluated for their in vitro biological activity. All three compounds exhibited different levels of cytotoxicity against cervical and breast cancer cell lines. However, compound 1 showed the best antiproliferative activity against all tested tumor cell lines, including HCC1937 and HeLa cells, which express high levels of wild-type epidermal growth factor receptor (EGFR). Western blot analyses demonstrated that compound 1 inhibited the activation of EGFR, protein kinase B (Akt), and extracellular signal-regulated kinase (Erk)1/2 in breast and cervical cancer cells at concentrations of 7 and 11 µM, respectively. The results from docking experiments with EGFR suggested the binding of compound 1 at the ATP binding site of EGFR. Furthermore, the crystal structure of compound 3 (7-(4-bromophenyl)-9-(pyridin-4-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine) was determined by single crystal X-ray analysis. Our work represents a promising starting point for the development of a new series of compounds targeting EGFR.

The synthetic cannabinoid MDMB-CHMCZCA was characterized by various spectroscopic techniques including NMR spectroscopy and tandem mass spectrometry. The synthetic sample was found to be of S-configuration by VCD spectroscopy and comparison of the data with DFT calculations, while ECD spectroscopy was found to be inconclusive in this case. The enantiomeric purity of samples from test purchases and police seizures was assessed by a self-developed chiral HPLC method.

The asymmetric unit of the title compound, C17H20O5, contains two independent molecules, A and B, with similar geometries [dihedral angles between the phenyl rings = 56.19 (8) and 54.98 (7)°, respectively]. Intramolecular O—H...O hydrogen bonds occur in both molecules. In the crystal, the A molecules form [1\overline{1}0] chains linked by O—H...O hydrogen bonds from the hydroxyl group to one of the methoxy O atoms. The B molecules form O—H...O hydrogen bonds to the hydroxyl O atoms of the A molecules and thus act as fixed spacers between the chains of molecule A. Some weak C—H...O contacts are also present.

The title compound, C16H12, crystallizes with four half molecules in the asymmetric unit, each of which is located on a crystallographic centre of inversion. The molecules are essentially planar. The crystal studied was a non-merohedral twin.

In the crystal structure of the solvated pentacyclic title compound, C21H10Cl4·0.5C6H12, the pentacyclic chloroaromatic rings are arranged in parallel layers, with the chlorine atoms protruding from these planes. Channels orthogonal to these layers are filled with disordered cyclohexane molecules.

The title compound N1-{4-[2-(methylthio)-1H-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine (2) was synthesized via nucleophilic aromatic substitution of 2-chloro-4-[2-(methylthio)-1H-imidazol-5-yl]pyridine (3) and p-phenylenediamine under acidic conditions. The synthesized compound 2 was characterized by 1H-NMR, 13C-NMR, MS HPLC, IR and UV-VIS. Additionally, the structure of 2 was confirmed by single crystal X-ray diffraction. Pyridinylimidazole 2 displays moderate affinity towards the c-Jun N-terminal kinase 3 and shows selectivity versus the closely related p38α mitogen-activated protein kinase.

Condensation of ethyl acetoacetate and phenetidine gives the title compound, C24H26N2O4. The planar ethoxyphenyl group attached to the pyridine ring is twisted about 77.96 (11)° out of the plane of the N-ethoxycarboxamidopyridine unit. The carboxamide unit forms a dihedral angle of about 28.1 (2)° with the pyridine ring.

A single crystal of the rel-R,R-enantiomer of the title compound, C16H14O2, was analyzed. The molecular structure is characterized by nearly planar cyclobutene rings and a torsion angle of the diol unit of 68.3 (2)°. Strands parallel to the b axis are built from diols connected via hydrogen bonds.

The side product of the cyclocondensation reaction between ethyl benzimidazole-2-carboxylate and the nitrile imine of the corresponding hydrazonyl chloride, C20H11BrClN5O, crystallized in two crystal forms. Form (1) is a co-crystal of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromophenyl group, C20H12BrN5O·0.143C20H11BrClN5O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by π–π interactions.

The asymmetric unit of the title compound, C22H36N2, comprises one half-molecule, the other half being generated by a center of inversion. The piperidine ring adopts a chair conformation, with the exocyclic N—C bond in an equatorial orientation. A short intramolecular C—H...N hydrogen bond occurs and forms an S(6) motif. No directional interactions beyond van der Waals contacts are observed between the molecules, which form a wave-like supramolecular architecture.

Abstract The severely ozone‐depleting trichlorofluoromethane is still appearing in several recycling processes or industrial applications. A simple and selective supramolecular complex formation of per‐methylated α‐cyclodextrin (1) with the highly volatile trichlorofluoromethane (2) is reported. This interaction moreover leads to thermally stable crystals. Per‐methylated α‐cyclodextrin is successfully exploited as a reversible and selective adsorption material for liquid and airborne trichlorofluoromethane as well as an affinity material for the chemical sensing and detection of this particular volatile organic component.

The title compound, which crystallized as a methanol and water solvate, C24H41NO5·CH4O·H2O, was obtained by heterologous expression of the brasilicardin gene cluster in the bacterium Amycolatopsis japonicum. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.

Three very similar and nearly planar molecules are present in the asymmetric unit of the title compound, C6Cl3N9. Whereas the threefold 1,5-annulation of the chlorotriazole moieties is obvious, all of the C and N atoms in the central triazine ring are equally disordered on the same site, approaching D3h symmetry for each of the molecules.

Four tetracyclic molecules of the title compound, C14H8N2SSe, are present in the asymmetric unit. Their molecular structures are very similar, adopting the shape of a saddle. The selenadiazole moiety of one of the molecules is disordered over two set of sites [occupancy ratio 0.618 (6):0.382 (6)]. In the crystal, layers of molecules with hydrogen surfaces extend parallel to the ab plane and are stacked along the c axis. The crystal studied was refined as an inversion twin.

The title compound, C12H9BrN2O3, was prepared in two steps from 2-chloro-3-nitropyridine. The nitrobiaryl unit is twisted, with dihedral angles of 35.4 (5)° between the nitro substituent and the pyridine ring to which it is bound, and 51.0 (5)° between the nitro group and the benzene ring. In the crystal, the molecules are connected via C—H...O hydrogen bonds, forming strands along the b-axis direction.

The title compound, C15H16N2O3S, was obtained by the reaction of (E)-1-(pyridin-4-yl)propan-1-one oxime and para-toluenesulfonic acid. The pyridine ring makes a dihedral angle of 54.70 (10)° with the benzene ring. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming a chain along the c-axis direction.

The title compound, C12H14Br2, was prepared by bromination/dehydrobromination of E,E,Z-cyclododecatriene. The crystal is composed of C2-symmetrical molecules with an E conformation of the bromoalkene fragments and nearly linear alkyne units. The torsion angles in the ring suggest significant ring strain.

The asymmetric unit of the title compound, C6H4Cl6O2·0.5H2O, contains one molecule of 1,1,1,6,6,6-hexachlorohex-3-yne-2,5-diol and half a water molecule located on a twofold rotation axis. In the crystal, pairs of hexachlorohexynediol molecules form centrosymmetric dimers connected via pairwise O—H...O hydrogen bonds. These dimers are connected by water molecules, resulting in layers parallel to the ab plane.

The title compound, 2C36H39N3O4·H2O, is a linear π-conjugated ladder oligomer with an alkyl chain on the central nitrogen atom. This diindolocarbazole, prepared via a twofold Cadogan reaction, adopts a sligthly convex shape, anti to the disordered octyl group. The unit cell contains nine molecules of the title compound and half a water molecule per main molecule. The water molecule forms hydrogen bridges, connecting the carbazole-NH and methoxy groups of different molecules. The crystal contains solvent molecules which are located in a channel parallel to the c axis. It was not possible to determine the position and nature of the solvent (a mixure of choroform, n-pentane and DMSO). The SQUEEZE [Spek (2015). Acta Cryst. C71, 9–18] option of PLATON was used to model the missing electron density. The given chemical formula and other crystal data do not take into account these solvent molecules.

The asymmetric unit of the title compound, C9H3Cl9, contains one molecule. Two slightly different conformations with nearly C3h symmetry are mutually disordered in a 1:1 ratio. This disorder enhances the overall structural symmetry to D3h.

The title solvated salt, 4C9H15N2Se+·4I−·CHCl3, co-crystallizes with chloroform. The asymmetric unit contains four very similar ion pairs and one solvent molecule. In the crystal, layers of parallel chloroform-filled channels formed by two different ion pairs alternate with layers formed by the other two ion pairs. Disorder is observed for some C and H atoms in two of the cations with occupancy ratios of 0.68:0.32 and 0.62:0.38.

The title compound, C32H48O8P2S2, was prepared by the nickel-catalyzed reaction of bis(5-bromothienyl)dipropoxybenzene and triisopropyl phosphite. The thiophene rings are inclined to the benzene ring by 14.6 (2) and 25.3 (3)°. One propyloxy group is disordered. Four hydrogen bonds connect the molecules, which are arranged in ribbons parallel to the bc plane.

The title compound, 3C9H15N2Se+·I3−·2I−, was prepared by methylation of the selenadiazole with methyl iodide. The asymmetric unit is composed of three independent selenadiazolium ions arranged in layers and connected via I3−·(I−)2 anion layers. The distances between the iodine and selenium atoms are significantly shorter than the nitrogen-to-iodine distances.

The title compound, C17H14ClN3O4, was prepared by the Huisgen reaction of 4-chloro-2-nitrobenzoyl chloride and 5-(4-propyloxyphenyl)tetrazole. The diphenyl-1,3,4-oxadiazole unit is nearly planar. The oxadiazole ring is inclined to the 4-chloro-2-nitrophenyl ring by 7.77 (8)°, and by 7.93 (8)° to the 4-propyloxyphenyl ring. The benzene rings are inclined to one another by 1.32 (7)°. The nitro group is twisted out of the plane of the benzene ring to which it is attached by 73.59 (16)°. The propoxy chain mean plane is inclined to the benzene ring to which it is attached by 4.46 (13)°. In the crystal, C—H...O and C—H...N hydrogen bonds connect the molecules, forming ribbons propagating along the b-axis direction. The ribbons are linked by C—H...π interactions, forming slabs parallel to the ab plane.

In the title compound, C20H10Cl3N5O, the 13-membered ring system makes dihedral angles of 78.64 (9)° with the trichlorophenyl ring and 62.60 (10)° with the pyridine ring. The crystal packing is dominated by π–π interactions between the 13-membered ring systems [centroid–centroid distance = 3.6655 (11)°].