Persistence of C–H⋯π(chelate ring) interactions in the crystal structures of Pd(S2COR)2. The utility of Pd(S2COR)2as precursors for palladium sulphide materials

Tan, Yee Seng; Halim, Siti Nadiah Abdul; Molloy, Kieran C.; Sudlow, Anna L.; Otero-de-la-Roza, Alberto; Tiekink, Edward R. T.

doi:10.1039/c5ce02126j

Cited by 28 publications

(10 citation statements)

References 87 publications

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“…Such interactions are well known in the supramolecular chemistry of metal 1,1dithiolates in general and dithiocarbamates in particular owing to significant delocalization of -electron density over the chelate rings relative to other 1,1-dithiolate ligands such as those cited above (Tiekink & Zukerman-Schpector, 2011;Tiekink, 2017). The unusual feature in the present case is that the (pyridine)C-H hydrogen bond forming the interaction is bifurcated (Tan et al, 2016), Table 3. Finally, for completeness, it is noted that analogous but intramolecular (coordinating pyridine)C-HÁ Á Á(chelate ring) interactions also occur, Fig.…”

Section: Tablementioning

confidence: 58%

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ² S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Poplaukhin

Tiekink

2017

Acta Crystallogr E Cryst Commun

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The common structural feature of the title compounds, [Zn(C4H8NOS2)2(C5H5N)]·C5H5N (I) and [Zn(C5H10NOS2)2(C5H5N)]·C5H5N (II), which differ by having dithiocarbamate N-bound methyl (I) and ethyl (II) groups, is the coordination of each ZnII atom by two non-symmetrically chelating dithiocarbamate ligands and by a pyridine ligand; in each case, the non-coordinating pyridine molecule is connected to the Zn-containing molecule via a (hydroxy)O—H...N(pyridine) hydrogen bond. The resulting NS4 coordination geometry is closer to a square-pyramid than a trigonal bipyramid in the case of (I), but almost intermediate between the two extremes in (II). The molecular packing features (hydroxy)O—H...O(hydroxy) hydrogen bonds, leading to supramolecular chains with a zigzag arrangement along [10-1] (I) or a helical arrangement along [010] (II). In (I), π–π [inter-centroid distances = 3.4738 (10) and 3.4848 (10) Å] between coordinating and non-coordinating pyridine molecules lead to stacks comprising alternating rings along the a axis. In (II), weaker π–π contacts occur between centrosymmetrically related pairs of coordinating pyridine molecules [inter-centroid separation = 3.9815 (14) Å]. Further interactions, including C—H...π(chelate) interactions in (I), lead to a three-dimensional architecture in each case.

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Section: Tablementioning

confidence: 58%

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ² S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Poplaukhin

Tiekink

2017

Acta Crystallogr E Cryst Commun

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“…3.80 Å [38]. While the cut-off based on the sum of van der Waals radii is convenient, it does not imply no secondary-bonding interaction exists between the selenium atoms in 15 and 16 [61,62]. As seen from Fig.…”

Section: Nickel Group Complexesmentioning

confidence: 99%

Molecular and supramolecular chemistry of mono- and di-selenium analogues of metal dithiocarbamates

Lee

Heard

2018

Coordination Chemistry Reviews

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This bibliographic review summarises the coordination chemistry of mono-and diselenium analogues of metal dithiocarbamate ligands, [RRꞌNCS2]-, as revealed by X-ray crystallography and spectroscopy (77 Se NMR and infrared). The Se-ligands are usually chelating but, bridging modes, up to 4, are known. Reflecting the larger size, greater polarisability and presence of a polar-cap (-hole), selenium atoms are more likely to be 2 involved in secondary-bonding (chalcogen-bonding) than sulphur when a competition exists. Isostructural relationships are established across the series in about one-third of the structures.

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“…This arises as the resonance structure with a formal negative charge on each sulphur atom, i.e. 2-S2C=O + R, contributes about 20% to the overall electronic structure meaning the chelate ring is both aromatic and electron-rich, serves as an efficient acceptor for end-on C-H ... π interactions and provide energies of stabilisation akin to intermolecular M … S secondary bonding interactions [7,51].…”

Section: Contactmentioning

confidence: 99%

Steric control of supramolecular association in structures of Zn(S₂COR)₂withN,N′-bis(pyridin-4-ylmethyl)oxalamide

Tan

Chun

Jotani³

et al. 2018

Zeitschrift Für Kristallographie - Crystalline Materials

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The crystal and molecular structures of the one-dimensional coordination polymer [Zn(S2COEt)2(4LH2)]n (1) and binuclear [Zn(S2COCy)2]2(4LH2) (2) are described, where 4LH2 is N,N′-bis(pyridin-4-ylmethyl)ethanediamide. In 1, the Zn(S2COEt)2 entities are linked by bidentate bridging 4LH2 ligands through the pyridyl-N atoms to generate a twisted supramolecular chain. As a result of monodentate xanthate ligands, the N2S4 donor set defines a distorted tetrahedral coordination geometry and, crucially, allows the participation of the non-coordinating sulfur atoms in supramolecular association. Thus, in the crystal amide-N–H···O(amide) and amide-N–H···S(thione) hydrogen bonds link chains into a three-dimensional architecture. The substitution of the ethyl group in the xanthate ligand with a cyclohexyl group results in very different structural outcomes. In 2, a binuclear molecule is observed with the coordination geometry for zinc being defined by chelating xanthate ligands and a pyridyl-N atom with the NS4 donor set defining a highly distorted geometry. In the molecular packing, amide-N–H···S(thione) hydrogen bonds stabilise a supramolecular chain along the a-axis and these are connected into a three-dimensional arrangement by methylene-C–H···O and methylene-C–H···π(pyridyl) interactions. The relative importance of the specified intermolecular interactions and weaker, contributing contacts has been revealed by an analysis of the calculated Hirshfeld surfaces of 1 and 2.

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Persistence of C–H⋯π(chelate ring) interactions in the crystal structures of Pd(S₂COR)₂. The utility of Pd(S₂COR)₂as precursors for palladium sulphide materials

Abstract: The influence of C–H⋯π(PdS2C) interactions in the molecular packing of Pd(S2COR)2increases as the steric bulk ofRincreases.

Cited by 28 publications

References 87 publications

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ² S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ² S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Molecular and supramolecular chemistry of mono- and di-selenium analogues of metal dithiocarbamates

Steric control of supramolecular association in structures of Zn(S₂COR)₂withN,N′-bis(pyridin-4-ylmethyl)oxalamide

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Persistence of C–H⋯π(chelate ring) interactions in the crystal structures of Pd(S2COR)2. The utility of Pd(S2COR)2as precursors for palladium sulphide materials

Abstract: The influence of C–H⋯π(PdS2C) interactions in the molecular packing of Pd(S2COR)2increases as the steric bulk ofRincreases.

Cited by 28 publications

References 87 publications

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ2 S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ2 S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Molecular and supramolecular chemistry of mono- and di-selenium analogues of metal dithiocarbamates

Steric control of supramolecular association in structures of Zn(S2COR)2withN,N′-bis(pyridin-4-ylmethyl)oxalamide

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Persistence of C–H⋯π(chelate ring) interactions in the crystal structures of Pd(S₂COR)₂. The utility of Pd(S₂COR)₂as precursors for palladium sulphide materials

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ² S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Crystal structure of bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-κ² S,S′](pyridine)zinc(II) pyridine monosolvate and its N-ethyl analogue

Steric control of supramolecular association in structures of Zn(S₂COR)₂withN,N′-bis(pyridin-4-ylmethyl)oxalamide