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A short diversity oriented total synthesis (DOTS) of substituted rutaecarpines, homo-luotonins, homo-vasicinone, homo-isaindigotones and homo-vasnetine has been achieved from the key tricyclic intermediate. The [6,6,6] tricyclic ketone, the mackinazolindione, was accessed from simple substrates i.e., quinazolinone diester obtained from the disubstituted anthranilamide which in turn was prepared from the coupling of amino acid ester and ethyl oxalyl chloride with isatoic anhydride and Dieckmann condensation chemistry.

The solid-state structures of N-cyclohexyltryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine}, C16H22N2, and two of its salts, N-cyclohexyltryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium bromide}, C16H23N2+·Br−, and N-cyclohexyltryptammonium fumarate (III) (systematic name: bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium} (2E)-but-2-enedioate), 2C16H23N2+·C4H2O42−, were determined by single-crystal X-ray diffraction. The freebase compound forms infinite chains along [010] through N—H...N hydrogen bonds. The bromide salt is held together by N—H...Br interactions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N—H...O hydrogen bonds.

The reactions of MnSO4·H2O, CoSO4·7H2O, NiSO4·6H2O and ZnSO4·7H2O with 3,5-lutidine (3,5-dimethylpyridine) yield crystals of pentaaqua(3,5-dimethylpyridine-κN)manganese(II) sulfate, [Mn(C7H9N)(H2O)5]SO4, (1), pentaaqua(3,5-dimethylpyridine-κN)cobalt(II) sulfate, [Co(C7H9N)(H2O)5]SO4, (2), pentaaqua(3,5-dimethylpyridine-κN)nickel(II) sulfate, [Ni(C7H9N)(H2O)5]SO4, (3), and pentaaqua(3,5-dimethylpyridine-κN)zinc(II) sulfate, [Zn(C7H9N)(H2O)5]SO4, (4), which were characterized by single-crystal X-ray diffraction. The four crystals are isostructural, demonstrating near identical unit-cell parameters and atomic positions. The metal atoms are all octahedrally coordinated, with one lutidine ligand and five water ligands. The sulfate dianion hydrogen bonds with the coordinated water molecules of the dicationic metal complex salts, generating infinite three-dimensional networks.

The title compound, 4-hydroxy-N-isopropyltryptamine (4) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]ethyl}-1H-indol-4-ol), C13H18N2O, was synthesized in three steps from 4-benzyloxyindole (1) (systematic name: 4-phenoxy-1H-indole), C15H13NO. (1) was treated with oxalyl chloride and isopropylamine to produce N-isopropyl-4-benzyloxy-3-indoleglyoxylamide (2) {systematic name: 2-[4-(benzyloxy)-1H-indol-3-yl]-2-oxo-N-(propan-2-yl)acetamide}, C20H20N2O3. (2) was reduced to generate 4-benzyloxy-N-isopropyltryptamine (3) or 4-HO-NiPT, which was characterized as its chloride salt 4-benzyloxy-N-isopropyltryptammonium chloride (3a) (systematic name: {2-[4-(benzyloxy)-1H-indol-3-yl]ethyl}(propan-2-yl)azanium chloride), C20H25N2O·Cl. Finally the benzyl group of (3) was removed via hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.

The solid-state structure of the title salt/adduct (systemic name: bis{[2-(4-acetyloxy-1H-indol-3-yl)ethyl](ethyl)propylazanium} but-2-enedioate–(E)-butenedioic acid (1/1)), 2C17H25N2O2+·C4H2O42−·C4H4O4, was determined by single-crystal X-ray diffraction. The asymmetric unit consists of a singly protonated tryptammonium cation, one half of a fumarate dianion and one half of a fumaric acid molecule. In the crystal, the ions and molecules are linked together in infinite chains propagating along [001] through a series of N—H...O and O—H...O hydrogen bonds.

The solid-state structures of two solvated forms of 4-glutarato-N,N-diisopropyltryptamine were determined by single-crystal X-ray diffraction, namely, 5-[(3-{2-[bis(propan-2-yl)azaniumyl]ethyl}-1H-indol-4-yl)oxy]-5-oxopentanoate methanol monosolvate, C21H30N2O4·CH3OH, and the analogous ethanol monosolvate, C21H30N2O4·C2H6O. In both compounds, the 4-glutarato-N,N-diisopropyltryptamine exists as a zwitterion with a protonated tertiary ammonium and a deprotonated glutarato carboxylate. The tryptamine zwitterions and alcohol solvates in both structures combine to produce near identical hydrogen-bonding networks, with N—H...O and O—H...O hydrogen bonds joining the molecules together in two-dimensional networks parallel to the (100) plane.

The solid-state structure of N-methylserotonin {systematic name: [2-(5-hydroxy-1H-indol-3-yl)ethyl](methyl)azanium hydrogen oxalate}, C11H15N2O+·C2HO4−, is reported. The structure possesses a singly protonated N-methylserotonin cation and one hydrogen oxalate anion in the asymmetric unit. In the crystal, the molecules are linked by N—H...O and O—H...O hydrogen bonds into a three-dimensional network.

The title compound, serotonin or 5-hydroxytryptamine (5-HT) [systematic name: 3-(2-aminoethyl)-1H-indol-5-ol], C10H12N2O, has one molecule in the asymmetric unit. The conformation of the ethylamino side chain is gauche–gauche [Ca—Ca—Cm—Cm and Ca—Cm—Cm—N (a = aromatic, m = methylene) torsion angles = −64.2 (3) and −61.9 (2)°, respectively]. In the crystal, the molecules are linked into a three-dimensional network by N—H...O and O—H...N hydrogen bonds.

The solid-state structure of the cobalt–β-picoline–sulfate complex tetra-μ3-sulfato-tetrakis[bis(3-methylpyridine)cobalt(II)], [Co4(SO4)4(C6H7N)8], is reported. The tetrameric cobalt cluster contains a cuboidal core comprised of four cobalt(II) cations and four sulfate anions at alternate cube vertices. The cobalt corners are each capped with two β-picoline ligands. The sulfate anions adopt a rare [3.2110] bridging motif, and the cuboidal cluster is unprecedented in coordination chemistry.

The solid-state structures of the synthetic psychedelic 5-methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT) {systematic name: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine}, C17H25N2O, and its fumarate salt, bis(5-methoxy-N,N-di-n-propyltryptammonium) fumarate (systematic name: bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-aminium} but-2-enedioate), 2C17H25N2O+·C4H2O42−, are reported. The freebase has a single tryptamine molecule in the asymmetric unit. The molecules are linked together by N—H...N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N—H...O hydrogen bonds. These chains are combinations of R44(22) rings, and C22(14) and C44(28) parallel chains along [001].

The title compound, bis(N,N-diallyl-5-methoxytryptammonium) (5-MeO-DALT) fumarate (systematic name: bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+·C4H2O42−, has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N—H...O hydrogen bonds. These chains are combinations of R44(22) rings, and C22(14) and C44(28) parallel chains along [111].

The solid-state structure of the bufotenine derivative bis(5-methoxy-2,N,N-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]dimethylazanium} (2E)-but-2-enedioate), 2C14H21N2O+·C4H2O42−, the bufotenidine derivative 5-methoxy-2,N,N,N-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]trimethylazanium iodide}, C15H23N2O+·I−, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C15H23N2O+·I−·H2O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked via N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers.

The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acetoxy-N-ethyl-N-methyltryptammonium (4-AcO-MET) hydrofumarate {systematic name: [2-(4-acetyloxy-1H-indol-3-yl)ethyl](methyl)ethylazanium 3-carboxyprop-2-enoate}, C15H21N2O2+·C4H3O4−, 4-acetoxy-N-allyl-N-methyltryptammonium (4-AcO-MALT) hydrofumarate {systematic name: [2-(4-acetyloxy-1H-indol-3-yl)ethyl](methyl)prop-2-enylazanium 3-carboxyprop-2-enoate}, C16H21N2O2+·C4H3O4−, and 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate–fumaric acid (1/1) (systematic name: bis{[2-(4-acetyloxy-1H-indol-3-yl)ethyl]diprop-2-enylazanium} but-2-enedioate–(E)-butenedioic acid (1/1)), 2C18H23N2O2+·C4H2O42−·C4H4O4, are reported. All three salts possess a protonated tryptammonium cation. The 4-AcO-MET and 4-AcO-MALT compounds are charge-balanced by 3-carboxyacrylate (hydrofumarate) anions. The 4-AcO-DALT complex crystallizes as a two-to-one tryptammonium-to-fumarate salt, which co-crystallizes with a fumaric acid molecule. Each structure is consolidated by N—H...O and O—H...O hydrogen bonds.

The title compound, bis(oxotremorine) fumarate bis(fumaric acid) {systematic name: 1-[4-(2-oxopyrrolidin-1-yl)but-2-ynyl]pyrrolidinium (2E)-but-2-enedioate bis[(2E)-but-2-enedioic acid]}, 2C12H19N2O+·C4H2O42−·2C4H4O4, has a single oxotremorine monocation protonated at the pyrrolidine nitrogen, one fumaric acid molecule and half of a fumarate dianion in the asymmetric unit. The ions and fumaric acid molecules are held together by N—H...O and O–H-...O hydrogen bonds in 40-membered rings with graph-set notation R66(40). The fumarate ions join these rings into infinite chains along [001].

Summary: Preventing spontaneous crystallization of supersaturated solutions by additives is of critical interest to successful process design and implementation, with numerous applications in chemical, pharmaceutical, medical, pigment, and food industries, but challenges remain in laboratory and industry settings and fundamental understanding is lacking. When copresented with antifreeze proteins (AFPs), otherwise spontaneously crystallizing osmolytes are maintained at high supersaturations for months in over-wintering organisms. Thus, we here explore the inhibition phenomenon by AFPs, using persistent crystallization of a common sugar alcohol, D-mannitol, as a case study. We report experimentally that DAFP1, an insect AFP, completely inhibits D-mannitol nucleation. Computer simulations reveal a new mechanism for crystallization inhibition where the population of the crystal-forming conformers are selectively bound and randomized in solution by hydrogen bonding to the protein surface. These results highlight the advantages of using natural polymers to address crystallization inhibition challenges and suggest new strategies in controlling the nucleation processes.

The solid-state structures of two quaternary trytpammonium salts, namely, N,N-dimethyl-N-n-propyltryptammonium (DMPT) iodide [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-propylazanium iodide], C15H23N2+·I−, and N-allyl-N,N-dimethyltryptammonium (DMALT) iodide, [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-(prop-2-en-1-yl)azanium iodide], C15H21N2+·I−, are reported. Both salts possess a trialkyltryptammonium cation and an iodide anion in the asymmetric unit, which are joined together through N—H...I interactions. The DMALT structure was refined as an inversion twin, and the allyl group is disordered over two orientations with a 0.70 (4):0.30 (4) ratio.

The solid-state structures of the hydrofumarate salts of two N,N-dialkyltryptamines, namely N-ethyl-N-propyltryptammonium (EPT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propylazanium 3-carboxyprop-2-enoate}, C15H23N2+·C4H3O4−, and N-allyl-N-methyltryptammonium (MALT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)(prop-2-en-1-yl)azanium 3-carboxyprop-2-enoate}, C14H19N2+·C4H3O4−, are reported. Both compounds possess a protonated tryptammonium cation, and a hydrofumarate anion in the asymmetric unit. The ethyl group of the EPT cation is modeled as a two-component disorder with 50% occupancy for each component. In the extended structure, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks parallel to the (001) plane for both compounds.

The title compound, bis(4-hydroxy-N-isopropyl-N-methyltryptammonium) (4-HO-MiPT) fumarate (systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium} but-2-enedioate), 2C14H21N2O+·C4H2O42−, has a singly protonated tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by N—H...O and O—H...O hydrogen bonds. These chains are a combination of R42(20) rings, and C22(15) and C44(30) parallel chains along (110). They are further consolidated by N—H...π interactions. There are two two-component types of disorder impacting the tryptammonium fragment with a 0.753 (7):0.247 (7) occupancy ratio and one of the fumarate oxygen atoms with a 0.73 (8):0.27 (8) ratio.

The solid-state structures of the naturally occurring psychoactive tryptamine norpsilocin {4-hydroxy-N-methyltryptamine (4-HO-NMT); systematic name: 3-[2-(methylamino)ethyl]-1H-indol-4-ol}, C11H14N2O, and its fumarate salt (4-hydroxy-N-methyltryptammonium fumarate; systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]methylazanium} but-2-enedioate), C11H15N2O+·0.5C4H2O42−, are reported. The freebase of 4-HO-NMT has a single molecule in the asymmetric unit joined together by N—H...O and O—H...O hydrogen bonds in a two-dimensional network parallel to the (100) plane. The ethylamine arm of the tryptamine is modeled as a two-component disorder with a 0.895 (3) to 0.105 (3) occupancy ratio. The fumarate salt of 4-HO-NMT crystallizes with a tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The ions are joined together by N—H...O and O—H...O hydrogen bonds to form a three-dimensional framework, as well as π–π stacking between the six-membered rings of inversion-related indoles (symmetry operation: 2 − x, 1 − y, 2 – z).

The solid-state structures of two cobalt–pyridine–sulfate compounds, namely catena-poly[[tetrakis(pyridine-κN)cobalt(II)]-μ-sulfato-κ2O:O′], [Co(SO4)(C5H5N)4]n, (1), and catena-poly[[tetrakis(pyridine-κN)cobalt(II)]-μ-sulfato-κ3O:O′,O′′-[bis(pyridine-κN)cobalt(II)]-μ-sulfato-κ3O,O′:O′′]n, [Co2(SO4)2(C5H5N)6]n, (2), are reported. Compound (1) displays a polymeric structure, with infinite chains of CoII cations adopting octahedral N4O2 coordination environments that involve four pyridine ligands and two bridging sulfate ions. Compound (2) is also polymeric with infinite chains of CoII cations. The first Co center has an octahedral N4O2 coordination environment that involves four pyridine ligands and two bridging sulfate ligands. The second Co center has an octahedral N2O4 coordination environment that involves two pyridine ligands and two bridging sulfate ions that chelate the Co atom. The structure of (2) was refined as a two-component inversion twin.

The solid-state structures of the salts of two substituted tryptamines, namely N-isopropyl-N-methyltryptaminium (MiPT) fumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C14H21N2+·C4H3O4−, and 4-hydroxy-N-isopropyl-N-methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4-hydroxy-1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate}, C14H21N2O+·C4H3O4−·H2O, are reported. Both salts possess a protonated tryptammonium cation and a 3-carboxyacrylate (hydrogen fumarate) anion in the asymmetric unit; the 4-HO-MiPT structure also contains a water molecule of crystallization. Both cations feature disorder of the side chain over two orientations, in a 0.630 (3):0.370 (3) ratio for MiPT and a 0.775 (5):0.225 (5) ratio for 4-HO-MiPT. In both extended structures, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks.

The title compound, 5-hydroxy-N,N,N-trimethyltryptammonium (5-HTQ) iodide {systematic name: [2-(5-hydroxy-1H-indol-3-yl)ethyl]trimethylazanium iodide}, C13H19N2O+·I−, has a single tryptammonium cation and one iodide anion in the asymmetric unit. The ions are held together by N—H...I and O—H...I hydrogen bonds in infinite chains along [100].

The title compound, 4-hydroxy-N,N-di-n-propyltryptammonium (4-HO-DPT) chloride {systematic name: N-[2-(4-hydroxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-aminium chloride}, C16H25N2O+·Cl−, has a singly protonated tryptammonium cation and one chloride anion in the asymmetric unit. A series of N—H...Cl and O—H...Cl hydrogen bonds connect the ions together in ladder chains along [010].

The title compound {systematic name: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine), C17H22N2O, has a single tryptamine molecule in the asymmetric unit. The molecules are linked by strong N—H...N hydrogen bonds into zigzag chains with graph-set notation C(7) along the [010] direction.

The title compound (systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium} but-2-enedioate tetrahydrate), 2C16H25N2O+·C4H2O42−·4H2O, has a singly protonated DPT cation, one half of a fumarate dianion (completed by a crystallographic centre of symmetry) and two water molecules of crystallization in the asymmetric unit. A series of N—H...O and O—H...O hydrogen bonds form a three-dimensional network in the solid state.

The solid-state structures of two metal–pyridine–sulfate compounds, namely catena-poly[[tetrakis(pyridine-κN)iron(II)]-μ-sulfato-κ2O:O′], [Fe(SO4)(C5H5N)4]n, (1), and catena-poly[[tetrakis(pyridine-κN)cobalt(II)]-μ-sulfato-κ2O:O′-[tetrakis(pyridine-κN)cobalt(II)]-μ-sulfato-κ3O,O′:O′′-[tris(pyridine-κN)cobalt(II)]-μ-sulfato-κ2O:O′], [Co3(SO4)3(C5H5N)11]n, (2), are reported. The iron compound (1) displays a polymeric structure, with infinite chains of FeII atoms adopting octahedral N4O2 coordination environments that involve four pyridine ligands and two bridging sulfate ligands. The cobalt compound (2) displays a polymeric structure, with infinite chains of CoII atoms. Two of the three Co centers have an octahedral N4O2 coordination environment that involves four pyridine ligands and two bridging sulfate ligands. The third Co center has an octahedral N3O3 coordination environment that involves three pyridine ligands, and two bridging sulfate ligands with one sulfate chelating the cobalt atom.

The title compound (systematic name: bis{2-[4-(acetyloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C14H19N2O2+·C4H2O42−, has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N—H...O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N—H...O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].

In the present work, the synthesis and characterization of two new phosphoric triamide (PT) compounds: one iron(III)-PT complex, Fe(NO3)3[OP(NC5H10)3]2 (1) and one PT ligand, OP(NHC5H9)3 (2) are surveyed. The structure of compound 2 has been determined by X-ray crystallography. For 1, the crystallographic data were collected in temperature 100 (2) K (crystal system: monoclinic; space group: P21/c; a = 18.5257 (6) Å; b = 15.7698 (5) Å; c = 14.2471 (4) Å; β = 106.7950 (2)°; V = 3984.7 (2) Å3 and Z = 4) that confirm the formula (NO3)3Fe[OP(NC5H10)3]2 for this compound. However, these crystallographic data don’t reported here due to poor quality and high R factor. In structure of compound 2, the asymmetric unit is composed of one complete molecule. In this structure, adjacent molecules are linked via [N—H]2•••O═P hydrogen bonds in a linear arrangement along b axis in which the P═O group acts as a double hydrogen-bond acceptor.

In present work, new phosphoric triamide N-(2-fluorobenzoyl)-N′,N"-diisopropylphosphoric triamide, [2-F-C6H4C(O)NH]P(O)[NHCH(CH3)2]2, was synthesized and characterized by X-ray crystallography analysis. The asymmetric unit consists of two independent molecules P1 and P2 which aggregate through NCP—Hâ¯OâC and [N—H]2â¯OâP hydrogen bonds, giving loops and forming two independent chains parallel to the a axis. For further investigation on intermolecular interactions in the studied compound, 3D Hirshfeld surfaces (HSs) mapped with dnorm and corresponding 2D fingerprint plots (FPs) were employed for two molecules P1 and P2. Hirshfeld surface analysis shows that the Hâ¯H (62.3% of total Hirshfeld surface area for molecule P1 and 62.8% for P2), Hâ¯O/Oâ¯H (13.1% for P1 and 12.8 % for P2), Hâ¯C/Câ¯H (12.4% for P1 and 12.7 % for P2) and Hâ¯F/Fâ¯H (8.2% for P1 and 7.8 % for P2) contacts are the dominant intermolecular interactions in the crystal structure.

The title compound {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propylamine}, C14H20N2, has a single molecule in the asymmetric unit. The molecules in the unit cell are held together in infinite one-dimensional chains along [010] through N—H...N hydrogen bonds between indole H atoms and trialkylamine N atoms.

A new cytotoxic thiodepsipeptide, verrucosamide (1), was isolated along with the known, related cyclic peptide thiocoraline, from the extract of a marine-derived actinomycete, a Verrucosispora sp., our strain CNX-026. The new peptide, which is composed of two rare seven-membered 1,4-thiazepane rings, was elucidated by a combination of spectral methods and the absolute configuration was determined by a single X-ray diffraction study. Verrucosamide (1) showed moderate cytotoxicity and selectivity in the NCI 60 cell line bioassay. The most susceptible cell lines were MDA-MB-468 breast carcinoma with an LD50 of 1.26 µM, and COLO 205 colon adenocarcinoma with an LD50 of 1.4 µM. Also isolated along with verrucosamide were three small 3-hydroxy(alkoxy)-quinaldic acid derivatives that appear to be products of the same biosynthetic pathway.

The title compound, C8H3Br2NO2, crystallizes with two near planar molecules in the asymmetric unit, with non-H atoms possessing mean deviations from planarity of 0.012 and 0.014 Å. The two molecules are connected by an N—H...O and a C—H...O hydrogen bond. In the crystal, molecules connect through a series of bifurcated N—(H,H)...O hydrogen bonds, forming chains propagating along the [1-1-1] direction. The molecules are further linked through intermolecular halogen interactions, including a Br...O close contact of 2.9409 (3) Å, and two C—H...Br interactions of 3.777 (3) and 3.845 (3) Å. These interactions link the chains into sheets lying parallel to the (1-23) plane.

The title compound, [Na(C8H4NO5S)(H2O)2]n, is a one-dimensional coordination polymer extending along the c axis. It consist of isatin sulfonate molecules linking pairs of sodium cations with Na—O bonds to both carbonyl and sulfonate oxygen atoms whereby two oxygen atoms of symmetry-related carbonyl groups bridge two sodium cations. The sodium cation possesses an octahedral coordination environment, including one sulfonate and three carbonyl oxygen atoms bound in the equatorial plane, and two water molecules bound axially. The isatin moiety of the organic ligand is nearly planar, with a mean deviation from planarity of 0.038 Å. The chains of the coordination polymer are further linked into a three-dimensional network with eight distinct interactions, including one N—H...O and four O—H...O hydrogen bonds, two C—H...O interactions and one π–π interaction.

The title compound, C10H9NO2, crystallizes with four molecules in the asymmetric unit. The molecules are all near planar, with the non-H atoms possessing mean deviations from planarity of 0.017, 0.026, 0.020 and 0.007 Å. In the crystal, the molecules form two dimers, each linked by a pair of N—H...O hydrogen bonds.

The title compound, C9H7NO2, has a single molecule in the asymmetric unit, with the non-H atoms possessing a mean deviation from planarity of 0.034 Å. In the crystal, the molecules dimerize through pairs of N—H...O hydrogen bonds. The nine-membered rings of the isatins stack along the b axis, through parallel slipped π–π interactions [intercentroid distance = 3.8832 (4) Å, interplanar distance = 3.4038 (7) Å and slippage = 1.8690 (12) Å].

The title compound, C10H12O3, has a single near planar molecule in the asymmetric unit, with the non-H atoms possessing a mean deviation from planarity of 0.132 Å. The molecules dimerize in the solid state through C—H...O interactions. These dimers are further linked through parallel slipped π–π interactions of the aryl rings [intercentroid distance = 3.5444 (11) Å, interplanar distance = 3.3998 (12) Å, slippage = 1.002 (2) Å].

The title compound, C8H3Cl2NO2, has a single near-planar molecule in the asymmetric unit, with the non-H atoms having a mean deviation from planarity of 0.042 Å. In the crystal, the molecules dimerize through two N—H...O hydrogen bonds. The molecules are further linked through slipped π–π interactions that propagate along the a axis [inter-centroid distance = 3.8639 (10) Å, interplanar distance = 3.3478 (10) Å and slippage = 1.9292 (15) Å].

The title compound, C8H3Cl2NO2, has a single molecule in the asymmetric unit that is close to planar, with the non-H atoms having a mean deviation from planarity of 0.035 Å. The molecules dimerize through two N—H...O hydrogen bonds. A weak intermolecular offset π–π interaction is also observed between the five- and six-membered rings, with a centroid–centroid separation of 3.8444 (16) Å.

The title compound, C8H3Cl2NO2, has a single, almost planar, molecule in the asymmetric unit, with the non-H atoms having a mean deviation from planarity of 0.027 Å. In the crystal, N—H...O hydrogen bonds form infinite C(4) chains along [100]. No π–π interactions were observed in the structure.

The molecule of the title compound, C8H4ClNO2, is planar, with the non-H atoms possessing an r.m.s. deviation from planarity of 0.062 Å. In the crystal, molecules are linked through N—H...O hydrogen bonds, forming chains along [010]. The chains are further linked through C—H...O hydrogen bonds, forming layers parallel to (001).

The molecule of the title compound, C8H4INO2, is almost planar, having an r.m.s. deviation from planarity of 0.019 Å for all non-H atoms. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are further linked by I...O close contacts of 3.078 (2) Å, forming chains along [10-1]. The nine-membered fused rings of the isatin molecules stack along the b axis, with parallel slipped π–π interactions [intercentroid distance = 3.594 (2) Å, interplanar distance = 3.379 (1) Å and slippage = 1.243 Å]. These interactions lead to the formation of a three-dimensional network.

The title compound, C8H4ClNO2, has two planar molecules in the asymmetric unit, with the non-H atoms showing a mean deviation from planarity of 0.015 and 0.022 Å, respectively. In the crystal, the molecules are linked through N—H...O hydrogen bonds to form infinite chains along [010]. They are further connected through C—H...Cl close contacts with a donor–acceptor distance of 3.682 (5) Å. No π–π interactions are observed in the structure.

The title compound, C8H4INO2, has a single planar molecule in the asymmetric unit, with the non-H atoms possessing a mean deviation from planarity of 0.058 Å. The molecules dimerize in the solid state through N—H...O hydrogen bonds. There are intermolecular I...O close contacts of 3.193 (4) Å that link the molecules into infinite chains along [20-1]. No π–π interactions were observed in the structure.

The title compound, C14H20O3S, demonstrates a trans conformation. The cyclohexyl ring in the structure exhibits a flattening, with average C—C—C angles of 111.2° and average C—C—C—C torsion angles of 55.6°. No significant intermolecular interactions are noted in the solid state.

The title compound, C8H4INO2, is an almost planar molecule having an r.m.s. deviation of 0.03 Å for all non-H atoms. In the crystal, molecules dimerize through pairs of N—H...O hydrogen bonds. These inversion dimers are linked through pairs of weak I...O interactions [3.184 (4) Å] to form zigzag chains along [010]. The chains are linked in the c-axis direction by parallel-slipped π–π interactions [intercentroid distance = 3.623 (3) Å, interplanar distance = 3.423 (2) Å and slippage = 1.667 (5) Å], forming corrugated sheets parallel to (011).

The title compound, [Ni2Cl2(μ-Cl)2(C10H8N2)2(C3H7NO)2], exists as a centrosymmetric dimer of two octahedral nickel centers. In the crystal, two chloride ions bridge the two nickel centers with one terminal chloride ion bound to each nickel atom. Coupled with a chelating bipyridine ligand and an O-bound N,N-dimethylformamide solvent molecule, each nickel center exhibits an slightly distorted octahedral coordination environment. The meridional chloride ions all sit in equatorial positions, with the bipyridine ligand occupying one equatorial and one axial position, and the N,N-dimethylformamide ligand occupying the final axial position. The 2,2′-bipyridine ligand binds to nickel in a near planar fashion, with the non-H atoms possessing a mean devation from planarity of 0.046 Å. No π–π interactions are observed in the crystal.

The title compound, C8H4BrNO2, has a single planar molecule in the asymmetric unit with the non-H atoms possessing a mean deviation from planarity of 0.034 Å. The molecules dimerize in the solid state through N—H...O hydrogen bonds. These dimers are further linked by intermolecular Br...O close contacts of 3.085 (2) Å to yield infinite chains along [20-1]. The nine-membered rings of the isatins stack along the a axis, with parallel slipped π–π interactions [intercentroid distance = 3.8320 (7) Å, interplanar distance = 3.341 (2) Å and slippage = 1.876 (4) Å].

The title compound, C8H4FNO2, has a single, almost planar, molecule in the asymmetric unit, with the non-H atoms having a mean deviation from planarity of 0.042 Å. Intermolecular N—H...O hydrogen bonds result in infinite chains along [100]. The molecules are further linked through weak C—H...O and C—H...F interactions.

The title compound, C8H4BrNO2, has a single planar molecule in the asymmetric unit with the non-H atoms possessing a mean deviation from planarity of 0.024 Å. The molecules dimerize in the solid state through N—H...O hydrogen bonds. There are intermolecular Br...O close contacts at 3.0430 (14) Å. The nine-membered rings of the isatins stack along [001] with parallel slipped π–π interactions [inter-centroid distance: 3.7173 (6) Å, inter-planar distance: 3.3110 (8) Å, slippage: 1.6898 (14) Å].