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author:("hukka, Matti")
1.  Crystal structure of 2-hy­droxy­imino-2-(pyridin-2-yl)-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide 
The mol­ecule of the title compound is approximately planar with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. In the crystal, mol­ecules are linked by bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers, which are in turn linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502).
The mol­ecule of the title compound, C14H13N5O2, is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å), with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. The oxime group is syn to the amide group, probably due to the formation of an intra­molecular N—H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, mol­ecules are linked by pairs of bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers. The latter are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502). The sheets are linked via π–π stacking inter­actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol­ecules, forming a three-dimensional structure.
PMCID: PMC4257442  PMID: 25552998
crystal structure; hy­droxy­imino; acetohydrazide; pyridyl­ethyl­idene; hydrogen bonding; π–π stacking inter­actions
2.  Di­chlorido­[N-(N,N-di­methyl­carbamimido­yl)-N′,N′,4-tri­methyl­benzohydrazonamide]­platinum(II) nitro­methane hemisolvate 
In the title compound, [PtCl2(C13H21N5)]·0.5CH3NO2, the PtII atom is coordinated in a slightly distorted square-planar geometry by two Cl atoms and two N atoms of the bidentate ligand. The (1,3,5-tri­aza­penta­diene)PtII metalla ring is slightly bent and does not conjugate with the aromatic ring. In the crystal, N—H⋯Cl hydrogen bonds link the complex mol­ecules, forming chains along [001]. The nitromethane solvent molecule shows half-occupancy and is disordered over two sets of sites about an inversion centre.
PMCID: PMC3998624  PMID: 24826095
3.  (μ-Acetato-κ2 O:O′)[μ-2,6-bis­({bis­[(pyri­din-2-yl-κN)meth­yl]amino-κN}meth­yl)-4-methyl­phenolato-κ2 O:O](metha­nol-κO)dizinc bis­(perchlorate) 
The binuclear title complex, [Zn2(C33H33N6O)(CH3COO2)(CH3OH)](ClO4)2, was synthesized by the reaction between 2,6-bis­({[bis­(pyridin-2-yl)meth­yl]amino}­meth­yl)-4-methyl­phenol (H-BPMP), Zn(OAc)2 and NaClO4. The two ZnII ions are bridged by the phenolate O atom of the octadentate ligand and the acetate group. An additional methanol ligand is terminally coordinated to one of the ZnII ions, rendering the whole structure unsymmetric. Other symmetric dizinc complexes of BPMP have been reported. However, to the best of our knowledge, the present structure, in which the two ZnII ions are distinguishable by the number of coordinating ligands and the coordination geometries (octahedral and square-pyramidal), is unique. The dizinc complex is a dication, and two perchlorate anions balance the charge. The –OH group of the coordinating methanol solvent mol­ecule forms a hydrogen bond with a perchlorate counter-anion. One of the anions is disordered over two sets of sites with an occupancy ratio of 0.734 (2):0.266 (2).
PMCID: PMC3998612  PMID: 24826088
4.  2,3-Di­phenyl­male­imide 1-methyl­pyrrol­idin-2-one monosolvate 
In the title compound, C16H11NO2·C5H9NO, the dihedral angles between the male­imide and phenyl rings are 34.7 (2) and 64.8 (2)°. In the crystal, the 2,3-di­phenyl­male­imide and 1-methyl­pyrrolidin-2-one mol­ecules form centrosymmetrical dimers via pairs of strong N—H⋯O hydrogen bonds and π–π stacking inter­actions between the two neighboring male­imide rings [centroid–centroid distance = 3.495 (2) Å]. The dimers are further linked by weak C—H⋯O and C—H⋯π hydrogen bonds into a three-dimensional framework.
PMCID: PMC3998429  PMID: 24764976
5.  Tetra­kis[bis­(pyridin-2-yl)amine-κN 2](nitrato-κO)silver(I) 
In the title complex, [Ag(NO3)(C10H9N3)4], the nitrate ligand is found to be disordered over two sets of positions, with occupancy factors of 0.473 (5) and 0.527 (5). The AgI ion is located in a square-pyramidal coordination environment formed by four N atoms from four bis­(pyridin-2-yl)amine ligands and one O atom from a nitrate ligand. Weak inter­actions between the AgI ions and the nitrate anions acting in a monodentate mode [Ag⋯O = 2.791 (13) and 2.816 (9) Å for the major component of the nitrate ligand, and 2.865 (8) and 2.837 (8) Å for the minor component] link the complex mol­ecules into a chain along [001]. N—H⋯O hydrogen bonds are observed.
PMCID: PMC3998263  PMID: 24764824
6.  5-Imino-3,4-diphenyl-1H-pyrrol-2-one 
The title compound, C16H12N2O, exists in the crystalline state as the 5-imino-3,4-di­phenyl­-1H-pyrrol-2-one tautomer. The dihedral angles between the pyrrole and phenyl rings are 35.3 (2) and 55.3 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate a graph-set motif of R 2 2(8) via N—H⋯N hydrogen bonds.
PMCID: PMC3998320  PMID: 24764881
7.  Bis(hy­droxy­ammonium) hexa­chlorido­platinate(IV)–18-crown-6 (1/2) 
In the title complex, (NH3OH)2[PtCl6]·2C12H24O6, the PtIV atom is coordinated by six chloride anions in a slightly distorted octa­hedral geometry. The Pt—Cl bond lengths are comparable to those reported for other hexa­chlorido­platinate(IV) species. The hy­droxy­ammonium groups act as linkers between the [PtCl6]2− anion and the crown ether mol­ecules. The anion is linked to two hy­droxy­ammonium cations via O—H⋯Cl hydrogen bonds and each hy­droxy­ammonium moiety is linked to a crown ether mol­ecule by hydrogen bonds between ammonium H atoms and 18-crown-6 O atoms. The crown ether mol­ecules have the classic crown shape in which all O atoms are located in the inner part of the crown ether ring and all –CH2– groups are turned to the outside.
PMCID: PMC3914042  PMID: 24526958
8.  Pyridinium bis­(pyridine-κN)tetra­kis­(thio­cyanato-κN)ferrate(III) 
In the title compound, (C5H6N)[Fe(NCS)4(C5H5N)2], the FeIII ion is coordinated by four thio­cyanate N atoms and two pyridine N atoms in a trans arrangement, forming an FeN6 polyhedron with a slightly distorted octa­hedral geometry. Charge balance is achieved by one pyridinium cation bound to the complex anion via N—H⋯S hydrogen bonding. The asymmetric unit consists of one FeIII cation, four thio­cyanate anions, two coordinated pyridine mol­ecules and one pyridinium cation. The structure exhibits π–π inter­actions between pyridine rings [centroid–centroid distances = 3.7267 (2), 3.7811 (2) and 3.8924 (2) Å]. The N atom and a neighboring C atom of the pyridinium cation are statistically disordered with an occupancy ratio of 0.58 (2):0.42 (2).
PMCID: PMC3684869  PMID: 23794971
9.  Pyridinium bis­(pyridine-κN)tetra­kis­(thio­cyanato-κN)ferrate(III)–pyrazine-2-carbo­nitrile–pyridine (1/4/1) 
In the title compound, (C5H6N)[Fe(NCS)4(C5H5N)2]·4C5H3N3·C5H5N, the FeIII ion is located on an inversion centre and is six-coordinated by four N atoms of the thio­cyanate ligands and two pyridine N atoms in a trans arrangement, forming a slightly distorted octa­hedral geometry. A half-occupied H atom attached to a pyridinium cation forms an N—H⋯N hydrogen bond with a centrosymmetrically-related pyridine unit. Four pyrazine-2-carbo­nitrile mol­ecules crystallize per complex anion. In the crystal, π–π stacking inter­actions are present [centroid–centroid distances = 3.6220 (9), 3.6930 (9), 3.5532 (9), 3.5803 (9) and 3.5458 (8) Å].
PMCID: PMC3647816  PMID: 23723782
10.  A second monoclinic polymorph of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-hy­droxy­imino-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide 
The title compound, C14H16N6O2, is a second monoclinic polymorph of 2-[1-(3,5-dimeth­yl)pyrazol­yl]-2-hy­droxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene] acetohydrazide, with two crystallographically independent mol­ecules per asymmetric unit. The non-planar mol­ecules are chemically equal having similar geometric parameters. The previously reported polymorph [Plutenko et al. (2012 ▶). Acta Cryst. E68, o3281] was described in space group Cc (Z = 4). The oxime group and the O atom of the amide group are anti with respect to the C—C bond. In the crystal, mol­ecules are connected by N—H⋯N hydrogen bonds into zigzag chains extending along the b axis.
PMCID: PMC3648291  PMID: 23723911
11.  cis-Dichlorido(dimethyl sulfoxide-κS)(N,N,N′,N′-tetra­methyl­guanidine-κN′′)platinum(II) 
In the title compound, cis-[PtCl2(C5H13N3)(C2H6OS)], the four-coordinate PtII atom is bonded to one N atom of the N,N,N′,N′-tetra­methyl­guanidine ligand, one dimethyl sulfoxide S atom and two chloride ligands, forming a cis-square-planar geometry. The bond lengths and angles of the N—Pt—Cl functionality are typical for imine dichloridoplatinum(II) complexes. The H atom of the imino group is oriented towards the O atom of the sulfoxide group of a neighboring mol­ecule and forms an N—H⋯O hydrogen bond.
PMCID: PMC3569208  PMID: 23424410
12.  Diammine{N-[2-(hy­droxy­imino)­propion­yl]-N′-[2-(oxidoimino)­propion­yl]propane-1,3-diaminido-κ4 N,N′,N′′,N′′′}iron(III) 
In the title compound, [Fe(C9H13N4O4)(NH3)2], the FeIII atom, lying on a mirror plane, is coordinated by four N atoms of a triply deprotonated tetra­dentate N-[2-(hy­droxy­imino)­propion­yl]-N′-[2-(oxidoimino)­propion­yl]propane-1,3-diaminide ligand in the equatorial plane and two N atoms of two ammonia mol­ecules at the axial positions in a distorted octa­hedral geometry. A short intra­molecular O—H⋯O hydrogen bond between the cis-disposed oxime O atoms stabilizes the pseudo-macrocyclic configuration of the ligand. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into a three-dimensional network. The ligand has a mirror-plane symmetry. One of the methyl­ene groups of the propane bridge is disordered over two sets of sites with equal occupancy factors.
PMCID: PMC3588803  PMID: 23468768
13.  2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hy­droxy­imino-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide 
In the title compound, C14H16N6O2, the dihedral angles formed by the mean plane of the acetohydrazide group [maximum deviation 0.0629 (12) Å] with the pyrazole and pyridine rings are 81.62 (6) and 38.38 (4)° respectively. In the crystal, mol­ecules are connected by N—H⋯O and O—H⋯N hydrogen bonds into supra­molecular chains extending parallel to the c-axis direction.
PMCID: PMC3588977  PMID: 23476213
14.  cis-Dichloridobis(2-isocyano­phenyl 4-meth­oxy­benzoate)palladium(II) chloro­form monosolvate 
In the title compound, [PdCl2(C15H11NO3)2]·CHCl3, the PdII atom adopts a slightly distorted square-planar coordination geometry composed of two Cl atoms in cis positions and two C atoms from isocyano­phenyl ligands. The mol­ecular conformation is stabilized by π–π stacking inter­actions [shortest centroid–centroid distance = 3.600 (1) Å] between substituted benzene rings of different ligands. The crystal packing is characterized by C—H⋯O and C—H⋯Cl inter­actions involving the chloro­form solvent mol­ecules.
PMCID: PMC3588737  PMID: 23468702
15.  Bis­{(E)-3-[2-(hy­droxy­imino)­propan­amido]-2,2-dimethyl­propan-1-aminium} bis[μ-(E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamido­(2−)]bis­{[(E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide]­copper(II)} bis­((E)-{3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­prop­yl}carbamate) acetonitrile disolvate 
The reaction between copper(II) nitrate and (E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide led to the formation of the dinuclear centrosymmetric copper(II) title complex, (C8H18N3O2)2[Cu2(C8H15N3O2)2(C8H17N3O2)2](C9H16N3O4)2·2CH3CN, in which an inversion center is located at the midpoint of the Cu2 unit in the center of the neutral [Cu2(C8H15N3O2)2(C8H17N3O2)2] complex fragment. The Cu2+ ions are connected by two N—O bridging groups [Cu⋯Cu separation = 4.0608 (5) Å] while the CuII ions are five-coordinated in a square-pyramidal N4O coordination environment. The complex mol­ecule co-crystallizes with two mol­ecules of acetonitrile, two mol­ecules of the protonated ligand (E)-3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­propan-1-aminium and two negatively charged (E)-{3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­prop­yl}carbamate anions, which were probably formed as a result of condensation between (E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide and hydro­gencarbonate anions. In the crystal, the complex fragment [Cu2(C8H15N3O2)2(C8H17N3O2)2] and the ion pair C8H18N3O2 +.C9H16N3O4 − are connected via an extended system of hydrogen bonds.
PMCID: PMC3588739  PMID: 23468704
16.  Ruthenium(II) arene complexes with chelating chloroquine analogue ligands: Synthesis, characterization and in vitro antimalarial activity† 
Three new ruthenium complexes with bidentate chloroquine analogue ligands, [Ru(η6-cym)(L1)Cl]Cl (1, cym = p-cymene, L1 = N-(2-((pyridin-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine), [Ru(η6-cym)(L2)Cl]Cl (2, L2 = N-(2-((1-methyl-1H-imidazol-2-yl)methylamino)ethyl)-7-chloroquinolin-4-amine) and [Ru(η6-cym)(L3)Cl] (3, L3 = N-(2-((2-hydroxyphenyl)methylimino)ethyl)-7-chloroquinolin-4-amine) have been synthesized and characterized. In addition, the X-ray crystal structure of 2 is reported. The antimalarial activity of complexes 1–3 and ligands L1, L2 and L3, as well as the compound N-(2-(bis((pyridin-2-yl)methyl)amino)ethyl)-7-chloroquinolin-4-amine (L4), against chloroquine sensitive and chloroquine resistant Plasmodium falciparum malaria strains was evaluated. While 1 and 2 are less active than the corresponding ligands, 3 exhibits high antimalarial activity. The chloroquine analogue L2 also shows good activity against both the choloroquine sensitive and the chloroquine resistant strains. Heme aggregation inhibition activity (HAIA) at an aqueous buffer/n-octanol interface (HAIR50) and lipophilicity (D, as measured by water/n-octanol distribution coefficients) have been measured for all ligands and metal complexes. A direct correlation between the D and HAIR50 properties cannot be made because of the relative structural diversity of the complexes, but it may be noted that these properties are enhanced upon complexation of the inactive ligand L3 to ruthenium, to give a metal complex (3) with promising antimalarial activity.
PMCID: PMC3303165  PMID: 22249579
17.  Tris(2,2′-bipyridine-κ2 N,N′)cobalt(III) bis­[bis­(pyridine-2,6-dicarboxyl­ato-κ3 O 2,N,O 6)cobaltate(III)] perchlorate dimethyl­formamide hemisolvate 1.3-hydrate 
In the title compound, [Co(C10H8N2)3][Co(C7H3NO4)2]2(ClO4)·0.5C3H7NO·1.3H2O, the CoIII atom in the complex cation is pseudoocta­hedrally coordinated by six N atoms of three chelating bipyridine ligands. The CoIII atom in the complex anion is coordinated by two pyridine N atoms and four carboxyl­ate O atoms of two doubly deprotonated pyridine-2,6-dicarboxyl­ate ligands in a distorted octa­hedral geometry. One dimethyl­formamide solvent mol­ecule and two water mol­ecules are half-occupied and one water mol­ecule is 0.3-occupied. O—H⋯O hydrogen bonds link the water mol­ecules, the perchlorate anions and the complex anions. π–π inter­actions between the pyridine rings of the complex anions are also observed [centroid–centroid distance = 3.804 (3) Å].
PMCID: PMC3470129  PMID: 23125573
18.  cis-Tetra­chloridobis(1H-imidazole-κN 3)platinum(IV) 
In the title complex, cis-[PtCl4(C3H4N2)2], the PtIV ion lies on a twofold rotation axis and is coordinated in a slightly distorted octa­hedral geometry. The dihedral angle between the imidazole rings is 69.9 (2)°. In the crystal, mol­ecules are linked by N—H⋯Cl hydrogen bonds, forming a three-dimensional network.
PMCID: PMC3344304  PMID: 22590070
19.  [μ-Bis(diphenyl­phosphan­yl-κP)methane]­deca­carbonyl­tri-μ-hydrido-trirhenium(I)(3 Re—Re) dichloromethane solvate 
In the title compound, [Re3(μ-H)3(C25H22P2)(CO)10]·CH2Cl2, the three Re atoms form a triangle bearing ten terminal carbonyl groups and three edge-bridging hydrides. The bis­(diphenyl­phosphan­yl)methane ligand bridges two Re atoms. Neglecting the Re—Re inter­actions, each Re atom is in a slightly distorted octa­hedral coordination environment. The dichloro­methane solvent mol­ecule is disordered over two sets of sites with fixed occupancies of 0.6 and 0.4.
PMCID: PMC3238719  PMID: 22199596
20.  Poly[di-μ2-aqua-μ5-(pyridine-2,6-dicarboxyl­ato)-μ3-(pyridine-2,6-dicarboxyl­ato)-cobalt(II)disodium] 
In the title compound, [CoNa2(C7H3NO4)2(H2O)2]n, the CoII atom is coordinated by two pyridine N atoms and four carboxyl­ate O atoms from two doubly deprotonated pyridine-2,6-dicarboxyl­ate ligands in a distorted octa­hedral geometry. One Na+ cation is coordinated by three carboxyl­ate O atoms and two water mol­ecules and the other is coordinated by five carboxyl­ate O atoms and two water mol­ecules in an irregular geometry. The bis­(pyridine-2,6-dicarboxyl­ato)cobalt complex units are connected by Na+ cations and bridging water mol­ecules into a three-dimensional coordination network. O—H⋯O hydrogen bonds are formed between the water mol­ecules and the carboxyl­ate O atoms.
PMCID: PMC3238695  PMID: 22199572
21.  (Tris{2-[(5-hy­droxy­pyridin-2-yl-κN)methyl­idene­imino-κN]eth­yl}amine)­zinc dinitrate 
In the complex cation of the title compound, [Zn(C24H27N7O3)](NO3)2, the tripodal tris­{[2-(5-hy­droxy­pyridin-2-yl)methyl­idene­imino]­eth­yl}amine ligand is coordin­ated to the Zn atom through the three pyridine and three imino N atoms. The coordination sphere of the Zn atom is based on an octahedron with a significant distortion towards trigonal prismatic, the twist angle being 45.58 (9)°. The crystal packing is formed by L and D anti­podes arranged in layers disposed parallel to the b axis. Strong O—H⋯O hydrogen bonding exists between the hy­droxy groups of the ligand and the nitrate anion.
PMCID: PMC3238702  PMID: 22199579
22.  N′-(2-Hy­droxy­benzyl­idene)-2-(hy­droxy­imino)­propano­hydrazide 
The mol­ecule of the title compound, C10H11N3O3, adopts an all-trans conformation and is approxomately planar, the largest deviation from the least-squares plane through all non-H atoms being 0.261 (1) Å. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, the mol­ecules are packed into layers lying parallel to the ab plane by π-stacking inter­actions between the benzene ring of one molecule and the C—N bond of the oxime group of another molecule; the shortest inter­molecular C⋯C separation within the layer is 3.412 (1) Å. The layers are connected by O—H⋯O and N—H⋯O hydrogen bonds.
PMCID: PMC3238939  PMID: 22199788
23.  4-Chloro­selanyl-3,5-diethyl-1H-pyrazol-2-ium chloride 
In the cation of the title compound, C7H12ClN2Se+·Cl−, the ethyl­ene groups and the Se–Cl fragment adopt a cis configuration with a C—Se—Cl angle of 96.09 (6)°. In the crystal, inter­molecular N—H⋯Cl hydrogen bonds link two cations and two chlorine anions into centrosymmetric clusters. π–π inter­actions between the pyrazole rings [centroid–centroid distance of 3.530 (2) Å] link these clusters into columns along [001] with short inter­molecular Se⋯Cl− contacts of 2.995 (1) Å.
PMCID: PMC3247471  PMID: 22220089
24.  fac-Tris(pyridine-2-carboxyl­ato-κ2 N,O)cobalt(III) 
In the title compound, [Co(C6H4NO2)3], the CoIII ion lies on a threefold rotation axis and is in a distorted octa­hedral environment defined by three N and three O donor atoms from three fac-disposed pyridine-2-carboxyl­ate ligands. The ligands are coordinated in a chelate fashion, forming three five-membered rings. In the crystal, translationally related complex molecules are organized into columns along [001] via C—H⋯O hydrogen bonds.
PMCID: PMC3247521  PMID: 22219826
25.  Diaqua­bis­(pyridine-2-carboxyl­ato-κ2 N,O)manganese(II) dimethyl­formamide hemisolvate 
There are two crystallographically independent complex mol­ecules with very similar geometries in the unit cell of the title compound, [Mn(C6H4NO2)2(H2O)2]·0.5C3H7NO. The central ion is situated in a distorted octa­hedral environment of two N- and four O-donor atoms from two pyridine-2-carboxyl­ate ligands and two cis-disposed water mol­ecules. The carboxyl­ate ligands are coordinated in a chelate fashion with the formation of two five-membered rings. In the crystal, the complex mol­ecules are connected by O—H⋯O hydrogen bonds between the coordinated water mol­ecules and the uncoordinated carboxyl­ate O atoms, thus forming hydrogen-bonded walls disposed perpendicularly to the bc plane.
PMCID: PMC3246979  PMID: 22219799

Results 1-25 (40)