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Crystal structures of μ-oxalato-bis-[azido-(hista-mine)-copper(II)] and μ-oxalato-bis-[(dicyan-amido)(hista-mine)-copper(II)].

Liu C, Abboud KA - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The apical coordination site in compound (II) is occupied by a monodentate dicyanamide anion through one of its terminal N atoms.The mol-ecules in both structures are centrosymmetric.The coordinatively unsaturated copper ions in compound (II) inter-act via a weak N⋯Cu inter-action with the dicyanamide ligand of a neighboring mol-ecule.

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Affiliation: Department of Chemistry and Environmental Science, Grenfell Campus, Memorial University of Newfoundland, Corner Brook, Newfoundland, A2H 6P9, Canada.

ABSTRACT
The title compounds, μ-oxalato-κ(4) O (1),O (2):O (1'),O (2')-bis-[[4-(2-amino-eth-yl)-1H-imid-azole-κ(2) N (3),N (4)](azido-κN (1))copper(II)], [Cu2(C2O4)(N3)2(C5H9N3)2], (I), and μ-ox-al-ato-κ(4) O (1),O (2):O (1'),O (2')-bis-[[4-(2-amino-eth-yl)-1H-imidazole-κ(2) N (3),N (4)](dicyanamido-κN (1))copper(II)], [Cu2(C2O4)(C2N3)2(C5H9N3)2], (II), are two oxalate-bridged dinuclear copper complexes. Each Cu(II) ion adopts a five-coordinate square-pyramidal coordination sphere where the basal N2O2 plane is formed by two O atoms of the oxalate ligand and two N atoms of a bidentate chelating histamine mol-ecule. The apical coordination site in compound (I) is occupied by a monodentate azide anion through one of its terminal N atoms. The apical coordination site in compound (II) is occupied by a monodentate dicyanamide anion through one of its terminal N atoms. The mol-ecules in both structures are centrosymmetric. In the crystals of compounds (I) and (II), the dinuclear complexes are linked through N-H⋯X and C-H⋯X (X = N, O) hydrogen bonds where the donors are provided by the histamine ligand and the acceptor atoms are provided by the azide, dicyanamide, and oxalate ligands. In compound (I), the coordinatively unsaturated copper ions inter-act with the histamine ligand via a C-H⋯Cu inter-action. The coordinatively unsaturated copper ions in compound (II) inter-act via a weak N⋯Cu inter-action with the dicyanamide ligand of a neighboring mol-ecule. The side chain of the histamine ligand is disordered over three sets of sites in (II).

No MeSH data available.


The crystal packing of compound (II), showing the hydrogen bonds as dashed lines. Atoms of disordered components have been omitted for clarity.
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fig4: The crystal packing of compound (II), showing the hydrogen bonds as dashed lines. Atoms of disordered components have been omitted for clarity.

Mentions: The two title compounds exhibit a common set of hydrogen bonds between dinuclear complexes where the histamine mol­ecule is the sole source of hydrogen-bond donors. The NH2 group of the histamine ethyl­amino side chain functions as a donor to form an N—H⋯O hydrogen bond where the acceptor is the O1 atom of the oxalate ligand. This hydrogen bond results in the formation of rows of parallel dinuclear complexes along the crystallographic b axis in compound (I) and along the crystallographic c axis in compound (II). Within each row, dinuclear complexes are placed side-to-side with each other rather than stacking directly above and below each other. As a result, there is essentially no overlap between the dinuclear planes. The same NH2 group of histamine is also the donor for a N—H⋯N hydrogen bond where the acceptor is the N3 atom of the azide in compound (I) and N4 of the dicyanamide in compound (II). This hydrogen bond links rows of dinuclear complexes to form sheets parallel to the ab plane in compound (I) (Fig. 3 ▸) and to the bc plane in compound (II) (Fig. 4 ▸). The protonated N—H group on the imidazole ring is another hydrogen-bond donor for a second N—H⋯N hydrogen bond, where the acceptor is N1 of azide in compound (I) and N6 of dicyanamide in compound (II). This hydrogen bond operates between dinuclear complexes from neighboring sheets and assembles the sheets into a three-dimensional network. For numerical values and symmetry operators for (I) and (II), see Tables 2 ▸ and 3 ▸.


Crystal structures of μ-oxalato-bis-[azido-(hista-mine)-copper(II)] and μ-oxalato-bis-[(dicyan-amido)(hista-mine)-copper(II)].

Liu C, Abboud KA - Acta Crystallogr E Crystallogr Commun (2015)

The crystal packing of compound (II), showing the hydrogen bonds as dashed lines. Atoms of disordered components have been omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645080&req=5

fig4: The crystal packing of compound (II), showing the hydrogen bonds as dashed lines. Atoms of disordered components have been omitted for clarity.
Mentions: The two title compounds exhibit a common set of hydrogen bonds between dinuclear complexes where the histamine mol­ecule is the sole source of hydrogen-bond donors. The NH2 group of the histamine ethyl­amino side chain functions as a donor to form an N—H⋯O hydrogen bond where the acceptor is the O1 atom of the oxalate ligand. This hydrogen bond results in the formation of rows of parallel dinuclear complexes along the crystallographic b axis in compound (I) and along the crystallographic c axis in compound (II). Within each row, dinuclear complexes are placed side-to-side with each other rather than stacking directly above and below each other. As a result, there is essentially no overlap between the dinuclear planes. The same NH2 group of histamine is also the donor for a N—H⋯N hydrogen bond where the acceptor is the N3 atom of the azide in compound (I) and N4 of the dicyanamide in compound (II). This hydrogen bond links rows of dinuclear complexes to form sheets parallel to the ab plane in compound (I) (Fig. 3 ▸) and to the bc plane in compound (II) (Fig. 4 ▸). The protonated N—H group on the imidazole ring is another hydrogen-bond donor for a second N—H⋯N hydrogen bond, where the acceptor is N1 of azide in compound (I) and N6 of dicyanamide in compound (II). This hydrogen bond operates between dinuclear complexes from neighboring sheets and assembles the sheets into a three-dimensional network. For numerical values and symmetry operators for (I) and (II), see Tables 2 ▸ and 3 ▸.

Bottom Line: The apical coordination site in compound (II) is occupied by a monodentate dicyanamide anion through one of its terminal N atoms.The mol-ecules in both structures are centrosymmetric.The coordinatively unsaturated copper ions in compound (II) inter-act via a weak N⋯Cu inter-action with the dicyanamide ligand of a neighboring mol-ecule.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry and Environmental Science, Grenfell Campus, Memorial University of Newfoundland, Corner Brook, Newfoundland, A2H 6P9, Canada.

ABSTRACT
The title compounds, μ-oxalato-κ(4) O (1),O (2):O (1'),O (2')-bis-[[4-(2-amino-eth-yl)-1H-imid-azole-κ(2) N (3),N (4)](azido-κN (1))copper(II)], [Cu2(C2O4)(N3)2(C5H9N3)2], (I), and μ-ox-al-ato-κ(4) O (1),O (2):O (1'),O (2')-bis-[[4-(2-amino-eth-yl)-1H-imidazole-κ(2) N (3),N (4)](dicyanamido-κN (1))copper(II)], [Cu2(C2O4)(C2N3)2(C5H9N3)2], (II), are two oxalate-bridged dinuclear copper complexes. Each Cu(II) ion adopts a five-coordinate square-pyramidal coordination sphere where the basal N2O2 plane is formed by two O atoms of the oxalate ligand and two N atoms of a bidentate chelating histamine mol-ecule. The apical coordination site in compound (I) is occupied by a monodentate azide anion through one of its terminal N atoms. The apical coordination site in compound (II) is occupied by a monodentate dicyanamide anion through one of its terminal N atoms. The mol-ecules in both structures are centrosymmetric. In the crystals of compounds (I) and (II), the dinuclear complexes are linked through N-H⋯X and C-H⋯X (X = N, O) hydrogen bonds where the donors are provided by the histamine ligand and the acceptor atoms are provided by the azide, dicyanamide, and oxalate ligands. In compound (I), the coordinatively unsaturated copper ions inter-act with the histamine ligand via a C-H⋯Cu inter-action. The coordinatively unsaturated copper ions in compound (II) inter-act via a weak N⋯Cu inter-action with the dicyanamide ligand of a neighboring mol-ecule. The side chain of the histamine ligand is disordered over three sets of sites in (II).

No MeSH data available.