A method for the prediction of the crystal structure of ionic organic compounds—the crystal structures of o-toluidinium chloride and bromide and polymorphism of bicifadine hydrochloride

McArdle, Patrick; Gilligan, Karen; Cunningham, Desmond; Dark, Rex; Mahon, Mary F.

doi:10.1039/b407861f

Cited by 134 publications

(105 citation statements)

References 17 publications

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“…43 The scattering factors were those given in the SHELXL program. Hydrogen atoms were located in the difference Fourier maps and refined isotropically.…”

Section: Methodsmentioning

confidence: 99%

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Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

McHugh

Erxleben

2011

Crystal Growth & Design

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Co-crystal and salt formation of the kinetin analogue N 6 -benzyladenine with the pharmaceutically acceptable co-crystal and salt formers maleic acid, oxalic acid, glutaric acid, succinic acid, benzoic acid and fumaric acid has been studied by solid-state and solvent-drop grinding in combination with X-ray powder diffraction. In all cases salt or co-crystal formation was observed. Single crystals of (bzadeH + )(mal -) (1) and (bzadeH + )2(ox 2-) (2) were obtained by solution crystallization and the X-ray structures are reported along with that of (adeH + )2(mal -)2 . ade . 2H2O (3) (bzadeH + = N 6 -benzyladeninium, adeH + = adeninium, ade = adenine, mal -= hydrogen maleate, ox 2-= oxalate). The hydrogen-bonding motifs in 1 -3 are discussed. The salts contain a robust bzadeH + -carboxylate or ade-carboxylate R2 2 (9) heterosynthon involving the protonated Hoogsteen sites (N6-H, N7-H) of bzadeH + and ade. Molecular recognition between the protonated Hoogsteen site and the carboxylate group stabilizes the unusual 7H,9H tautomer of bzadeH + in 2 and the non-canonical 7H-adenine tautomer in 3.* To whom correspondence should be addressed. ABSTRACT Co-crystal and salt formation of the kinetin analogue N 6 -benzyladenine with the pharmaceutically acceptable co-crystal and salt formers maleic acid, oxalic acid, glutaric acid, succinic acid, benzoic acid and fumaric acid has been studied by solid-state and solvent-drop grinding in combination with X-ray powder diffraction. In all cases salt or co-crystal formation was observed. Single crystals of (bzadeH + )(mal -) (1) and (bzadeH + )2(ox 2-) (2) were obtained by solution crystallization and the X-ray structures are reported along with that of (adeH + )2(mal -)2 . ade . 2H2O (3) (bzadeH + = N 6 -benzyladeninium, adeH + = adeninium, ade = adenine, mal -= hydrogen maleate, ox 2-= oxalate). The hydrogen-bonding motifs in 1 -3 are discussed. The salts contain a robust bzadeH + -carboxylate or ade-carboxylate R2 2 (9) heterosynthon involving the protonated Hoogsteen sites (N6-H, N7-H) of bzadeH + and ade. Molecular recognition between the protonated Hoogsteen site and the carboxylate group stabilizes the unusual 7H,9H tautomer of bzadeH + in 2 and the non-canonical 7H-adenine tautomer in 3.3

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“…43 The scattering factors were those given in the SHELXL program. Hydrogen atoms were located in the difference Fourier maps and refined isotropically.…”

Section: Methodsmentioning

confidence: 99%

“…Graphics were produced with ORTEX. 43 Crystallographic data and details of refinement are reported in Table 2. accepted that salts will be obtained, when the difference between the pKa values of the base and the acid, pKa, is > 3, while a pKa < 0 will lead to a co-crystal.…”

Section: Methodsmentioning

confidence: 99%

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

McHugh

Erxleben

2011

Crystal Growth & Design

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“…The structure was solved by direct methods and subsequent Fourier syntheses and refined by full-matrix least squares on F 2 using SHELXS-97, SHELXL-97 [18][19][20] and Oscail [21]. The scattering factors were those given in the SHELXL program.…”

Section: X-ray Analysismentioning

confidence: 99%

DNA damage and induction of apoptosis in pancreatic cancer cells by a new dinuclear bis(triazacyclonane) copper complex

Montagner

Gandin

Marzano

et al. 2015

Journal of Inorganic Biochemistry

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The dinuclear copper(II) complex [Cu 2 {bcmp(-H)}(μ-OH)](NO 3 ) 2 ·H 2 O (1, bcmp = 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol) has been synthesized and characterized by electrospray ionization mass spectrometry, potentiometric titration and cyclovoltammetry. The X-ray structure of the analogous perchlorate salt [Cu 2 {bcmp(-H)}(μ-OH)](ClO 4 ) 2 ·2.5H 2 O (2) was determined. Cytotoxicity studies showed very promising activity of 1 against various pancreatic tumor cell lines with IC 50 values comparable or even lower than those of cisplatin. The Cu complex displayed low toxicity against a human non-tumor cell line (HEK 293) demonstrating selectivity for cancer cells. 1 converts supercoiled pUC19 plasmid DNA into the nicked form at micromolar concentrations in the absence of added reductants. A detailed kinetic study on the hydrolysis of the DNA model bis(2,4-dinitrophenyl) phosphate (BDNPP) has been performed. 1 hydrolyses BDNPP with a second order rate constant of 0.047 M s −1 at pH 8 and 40°C. Finally, single cell electrophoresis (comet assay) and fluorescence microscopy analysis showed that 1 interacts with cellular DNA and induces apoptotic cell death of Capan-1 pancreatic cancer cells. Western blotting analysis indicated that the Cu complex activates the p53 dependent pathway of apoptosis.

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“…The observed extinctions are consistent with the space groups P6 3 mc, P 62c or P6 3 /mmc. The crystal structure has been solved employing direct methods (using SHELX [30] in the program OSCAIL [31] ) in the hexagonal space group with highest symmetry P6 3 /mmc (Nr.194; a = 0.52012(1), c = 0.63315(3) nm). Although direct methods prompt the crystallographic sites 2c (1/3, 2/3,1/4) and 2b (0,0,1/4) for the heavy scatterers i.e.…”

Section: The Crystal Structure Of W 1àx Bmentioning

confidence: 99%

Crystal Structure of W1−x B3 and Phase Equilibria in the Boron-Rich Part of the Systems Mo-Rh-B and W-{Ru,Os,Rh,Ir,Ni,Pd,Pt}-B

Zeiringer

Rogl

Grytsiv

et al. 2014

J. Phase Equilib. Diffus.

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The crystal structure of W 12x B 3 has been reinvestigated by x-ray single crystal diffraction and revealed isotypism with the Mo 12x B 3 structure type (space group P6 3 /mmc; a = 0.52012(1), c = 0.63315(3) nm; R F = 0.040). As a characteristic feature of the structure, planar hexagonal metal layers (1/3 of atoms removed from ordered positions) sandwich planar boron honeycomb layers. One of the two W-sites shows a random defect of about 73%. Strong metal boron and boron-boron bonds are responsible for high mechanical stability. Although W 12x B 3 at about 80 at.% B is the metal boride richest in boron, it contains no directly linked three-dimensional boron framework. The solubility of Rh, Ir, Ni, Pd and Pt in W 12x B 3 as well as of Rh in Mo 12x B 3 has been investigated in as cast state and after annealing. Furthermore, phase equilibria in the boron rich part of the corresponding isothermal sections W-TM-B (TM = Rh, Ir at 1100°C, TM = Ni, Pd at 900°C and TM = Pt at 800°C) and Mo-Rh-B (at 1100°C) have been established. A ternary compound only forms in the system W-Ir-B: s 1 -W 12x Ir x B 2 with ReB 2 structure type (space group P6 3 /mmc; a = 0.2900, c = 0.7475 nm). The type of formation and crystal structure of diborides W 12x TM x B 2 (TM = Ru, Os, Ir) isotypic with ReB 2 were studied by x-ray powder diffraction and electron probe microanalysis in as cast state and after annealing at 1500°C. Accordingly, W 0.5 Os 0.5 B 2 (a = 0.29127(1), c = 0.7562(1) nm) forms directly from the melt, whereas W 0.4 Ru 0.6 B 2 (a = 0.29027(1), c = 0.74673(2) nm) and W 0.6 Ir 0.4 B 2 (a = 0.29263(1), c = 0.75404(8) nm) are incongruently melting. Annealing at 1500°C leads in case of the iridium compound to an almost single-phase product but the same procedure does not increase the amount of the ruthenium diboride.

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A method for the prediction of the crystal structure of ionic organic compounds—the crystal structures of o-toluidinium chloride and bromide and polymorphism of bicifadine hydrochloride

Cited by 134 publications

References 17 publications

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

DNA damage and induction of apoptosis in pancreatic cancer cells by a new dinuclear bis(triazacyclonane) copper complex

Crystal Structure of W1−x B3 and Phase Equilibria in the Boron-Rich Part of the Systems Mo-Rh-B and W-{Ru,Os,Rh,Ir,Ni,Pd,Pt}-B

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A method for the prediction of the crystal structure of ionic organic compounds—the crystal structures of o-toluidinium chloride and bromide and polymorphism of bicifadine hydrochloride

Cited by 134 publications

References 17 publications

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N6-Substituted Adenine

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N6-Substituted Adenine

DNA damage and induction of apoptosis in pancreatic cancer cells by a new dinuclear bis(triazacyclonane) copper complex

Crystal Structure of W1−x B3 and Phase Equilibria in the Boron-Rich Part of the Systems Mo-Rh-B and W-{Ru,Os,Rh,Ir,Ni,Pd,Pt}-B

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Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N⁶-Substituted Adenine