Startseite Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru
Artikel Open Access

Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru

  • Joel M. Gichumbi , Bernard Omondi EMAIL logo und Holger B. Friedrich
Veröffentlicht/Copyright: 30. März 2018

Abstract

C22H22Cl4N2O4Ru, monoclinic, P21/c (no. 14), a = 15.0181(3) Å, b = 10.3983(2) Å, c = 16.6496(3) Å, β = 112.459(1)°, V = 2402.84(8) Å3, Z = 4, Rgt(F) = 0.0180, wRref(F2) = 0.0474, T = 173(2) K.

CCDC no.:: 1830403

The title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.26 × 0.23 × 0.22 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.13 mm−1
Diffractometer, scan mode:Bruker SMART APEX-II, φ and ω-scans
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:44260, 5964, 0.027
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5622
N(param)refined:301
Programs:Bruker programs [1], SHELX [2], WinGX & ORTEP [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
Ru10.73293(2)0.97102(2)0.06453(2)0.01087(4)
N10.76030(8)1.11564(11)−0.00928(7)0.0142(2)
N20.85109(7)1.06443(11)0.15235(7)0.0128(2)
O10.01825(8)0.40214(11)0.21584(7)0.0279(2)
O20.12567(8)0.57521(12)0.24527(7)0.0312(3)
O3−0.00697(8)0.56582(12)0.11131(7)0.0289(2)
O4−0.03102(10)0.60840(14)0.24073(9)0.0414(3)
Cl10.64386(2)1.13436(3)0.10190(2)0.01749(7)
Cl21.06256(2)0.97839(4)0.22049(2)0.02525(8)
Cl30.79524(3)0.96298(3)0.42910(2)0.02279(7)
Cl40.02582(2)0.53860(3)0.20303(2)0.01834(7)
C10.70876(10)1.13973(14)−0.09356(9)0.0206(3)
H10.6554941.085967−0.1244360.025*
C20.73111(11)1.24100(15)−0.13687(9)0.0243(3)
H20.6941881.254638−0.1968750.029*
C30.80704(11)1.32202(14)−0.09273(9)0.0222(3)
H30.8234391.390882−0.1219910.027*
C40.85903(10)1.30076(13)−0.00456(9)0.0177(3)
H40.9104501.3562120.0279590.021*
C50.83410(9)1.19684(12)0.03476(8)0.0140(2)
C60.88282(9)1.16419(13)0.12590(8)0.0145(2)
H60.9351651.2136260.1639010.017*
C70.89304(9)1.02237(12)0.24069(8)0.0143(2)
C80.98773(10)0.97846(13)0.27821(9)0.0170(3)
C91.02231(10)0.92808(14)0.36198(9)0.0205(3)
H91.0868140.8979340.3874000.025*
C100.96326(10)0.92166(13)0.40845(9)0.0200(3)
H100.9865140.8860660.4653100.024*
C110.86954(10)0.96787(12)0.37099(9)0.0172(3)
C120.83338(10)1.01688(12)0.28747(9)0.0156(2)
H120.7687091.0464380.2622500.019*
C130.65143(10)0.81852(13)0.10166(9)0.0181(3)
C140.74979(10)0.78628(12)0.13582(9)0.0167(2)
H140.7851590.7862510.2003310.020*
C150.80424(9)0.78390(12)0.08177(8)0.0146(2)
H150.8761340.7800600.1096820.018*
C160.76031(9)0.80956(12)−0.00819(8)0.0143(2)
C170.65915(9)0.83759(12)−0.04329(9)0.0161(2)
H170.6296210.872971−0.1036010.019*
C180.60638(9)0.84407(13)0.01014(9)0.0182(3)
H180.5405690.883204−0.0133690.022*
C190.81548(10)0.80802(14)−0.06756(9)0.0183(3)
H190.7805160.863671−0.1189720.022*
C200.91817(11)0.85847(16)−0.02393(10)0.0259(3)
H20A0.9168420.944551−0.0004470.039*
H20B0.9482910.862814−0.0667170.039*
H20C0.9553570.8004790.0234010.039*
C210.81590(12)0.66978(16)−0.09979(11)0.0282(3)
H21A0.8484880.613288−0.0500740.042*
H21B0.8500480.667337−0.1395230.042*
H21C0.7494200.640480−0.1303680.042*
C220.59511(12)0.83266(15)0.15891(11)0.0278(3)
H22A0.6390000.8267350.2199890.042*
H22B0.5468780.7640390.1457200.042*
H22C0.5627350.9164110.1483180.042*

Source of material

To a suspension of [(η6-p-cymene)Ru(μ—Cl)Cl]2 (0.2 mmol) in methanol (20 mL) was added the ligand N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine (0.42 mmol). The mixture was stirred at room temperature for 3 h followed by the reduction in volume of the solvent in vacuo to about 10 mL before adding NaClO4 in slight excess (0.42 mmol). The mixture was then cooled in an ice bath while stirring for 2 h leading to a precipitate, which was collected by filtration. The filtrate was washed with diethyl ether and dried in vacuo. Crystals of the title compound suitable for single-crystal X-ray diffraction studies were grown by the liquid diffusion method where the solutions of the compounds in acetone were layered with hexane and left undisturbed for 2 days. Orange crystals, yield 82%, m.p. 210 °C (decomp.).

Experimental details

All hydrogen atoms were placed in idealized positions and refined in riding models with Uiso assigned the values of 1.2 times those of their parent atoms and the distances of C—H were constrained to 0.93 Å for all the aromatic H atoms, 0.96 Å for methyl hydrogens and 0.98 Å for methine hydrogen.

Discussion

Half-sandwich arene ruthenium complexes represent one of the most sought after organometallic compounds due to their potential applications in catalytic and biological applications [4]. Their unique properties, which include mild reaction conditions required for synthesis, high yields and, for some, a wide range of stability and solubility under aqueous conditions, have made them be of great interest in organometallic chemistry [5], [6], [7], [8]. The coordinated arene moiety is relatively inert towards substitution and acts as spectator ligand [6]. These stabilize and protect the metal centre and thereby prevent rapid oxidation of the Ru(II) to Ru(III) [6].

The asymmetric unit of the title compound contains a Ru(II) title complex and one perchlorate anion. The title compound is similar to our previously published compounds in a series of half-sandwich ruthenium(II) complexes [7], [8], [9], [10], [11].

The cationic complex features the known “pseudo-octahedral three-legged piano stool” structure. In this arrangement, the ruthenium centre is coordinated to the N,N′-bidentate ligand through the N atom of the pyridine and the N atom of the imine group and a chlorido ligand at the base of the stool and the p-cymene ring at the apex of the stool. The Ru—N bond lengths are 2.0606(12) and 2.0804(13) Å. This value is comparable to those reported for other arene ruthenium complexes with N,N′ donor ligands [9], [10], [11], [12], [13], [14], [15], [16]. The N—Ru—N bond angles was 76.52(6)°. The N—Ru—Cl bond angles were 84.04(4)° and 84.05(5)°. These values are close to those reported for related compounds [9], [10], [11], [12], [13], [14], [15], [16].

Acknowledgements

We wish to extend our sincere thanks to the NRF, THRIP (Grant No. Tp 1208035643) and UKZN (URF) for financial support. Gichumbi, M. Joel thanks Prof. E.N. Njoka for his support.

References

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Received: 2017-12-19
Accepted: 2018-3-16
Published Online: 2018-3-30
Published in Print: 2018-5-24

©2018 Joel M. Gichumbi et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14
  3. Crystal structure of 4-methoxy-6-phenyl-2H-pyran-2-one, C12H10O3
  4. Crystal structure of tris{(3-((E)-(((E)-2-oxidobenzylidene)hydrazono)methyl)-2-oxo-2H-chromen-4-olato-κ3O,N:N′)}dicobalt(III)tris(dimethylformamide), C60H50Co2N9O15
  5. Crystal structure of poly[bis(1-methyl-[4,4′-bipyridin]-1-ium-κN)-tetrakis(μ3-sulfato-κ3O:O′:O′′)trizinc(II)], C22H22Zn3N4O16S4
  6. Crystal structure of (5Z,10Z)-3,13-dichloro-17,18-dioxo-5,11-diphenyl-8,9,17,18-tetrahydro-7H-dibenzo[e,n][1,4,8,12]tetraazacyclopentadecine-16,19-diido-κ4N,N′,N′′,N′′′)copper(II), C31H22N4O2Cl2Cu
  7. Crystal structure of bis{5-methoxy-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2N,O}zinc(II), C34H24N2O8Zn
  8. Crystal structure of 2,2′-((((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenolato-κ2N4O)nickel(II), C28H22N2O4Ni
  9. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato)cobalt(II), C36H26N2O4Co
  10. Crystal structure of camptothecin, C20H16N2O4
  11. Crystal structure of (2-(chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato–κ2O,O′)(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, Ni(C16H36N4)(C12H12O4Cl)ClO4⋅H2O
  12. Crystal structure of 3-(2-chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (C19H13ClN2O2)
  13. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis{[(E)-2,6-diisopropyl-N-(pyridin-3-ylmethylene)aniline]copper (II)}, C44H56Cu2N4O8
  14. Crystal structure of diethyl 2-(2-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19Cl1O6
  15. Crystal structure of (μ2-2,2′-bipyridine-3,3′-dicarboxylato)-bis(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)-di-nickel(II) perchlorate N,N′-dimethylformamide solvate, C50H92Cl2N12Ni2O14
  16. Crystal structure of catena-poly[triaqua(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)-(1,2-bis(4-pyridyl)ethane-κN)nickel(II)] 2-aminonicotinate nitrate – 1,2-bis(4-pyridyl)ethane – water (2/1/8), C36H44N8NiO12
  17. Hydrothermal synthesis and crystal structure of poly[bis(μ2-3-(3,5-dicarboxyphenoxy)phthalato-κ3O,O′:O′′)-(μ2-1,2-di(pyridin-4-yl)ethane-κ2N:N′)copper(II)], C22H14CuNO9
  18. Crystal structure of catena-poly[aqua-(methanol-κO)-bis(μ2-4-(pyridin-4-yl)benzoato-κ2N:O)-bis(triphenylphospine-κP)disilver(I)], C61H52Ag2N2O6P2
  19. The crystal structure of 6-(4-bromobenzyl)-1,3,5-trimethyl-7-phenyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione, C22H20BrN3O2
  20. Synthesis and crystal structure of catena-poly[bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κO2O′,O′′)-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)zinc(II)], C44H32N4ZnCl4O4
  21. Crystal structure of diaqua-bis[N-phenyl-2-(quinolin-8-yloxy)acetamide-κ3-N,O,O′]-nitrato(κ2O,O′)-cerium(III) dinitrate - acetone (1/2), C40H44N7O17Ce
  22. Crystal structure of the 2D coordination polymer poly[aqua(μ2-2,2′-(1,2-phenylene)diacetato-κ3O,O′:O′)-(μ2-4,4′-bis((1H-1,2,4-triazol-1-yl)methyl)-1,1′-biphenyl-κ2N:N′)cobalt(II)], C28H26CoN6O5
  23. Crystal structure of (dimethylformamide-κO)(perchlorato-κ2O,O′){μ2-6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-methoxyphenolate)-κ8N,N′,O:O,O′:O′,O′′,O′′′}sodium(I)nickel(II), C25H23Br2ClN3NaNiO9
  24. The crystal structure of catena-poly[bis((4-aminophenyl)sulfonyl)(pyrimidin-2-yl)amido-κ2N,N′)-bis(μ2-4,4′-bipyridine-N,N′2N:N′)zinc(II) – methanol (1/2), C32H34N10O6S2Zn
  25. Synthesis and crystal structure poly[aqua(μ3-2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetate-κ4O,O′:O′′:O′′′) sodium] monohydrate, C18H18NNaO11S
  26. Crystal structure of methyl 4′-amino-3′,5′-diisopropyl-[1,1′-biphenyl]-4-carboxylate, C20H25NO2
  27. Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru
  28. Crystal structure of 2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione, C14H15Cl2N3OS
  29. Crystal structure of methyl 4′-amino-3′,5′-dimethyl-[1,1′-biphenyl]-4-carboxylate, C16H17NO2
  30. The crystal structure of 1-(5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pentan-1-on, C19H19F3FeN2O
  31. The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C34H56O6
  32. Crystal structure of methyl 10-(pyridin-4-yl)-anthracene-9-carboxylate, C21H15NO2
  33. Crystal structure of catena-poly[diaqua-bis(di(N2,N6-dihydroxypyridine-2,6-dicarboxamide))potassium(I)]tetrahydrate, C14H25N6O14K
  34. Crystal structure of poly{[μ2-(E)-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′][μ3–cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′:O′′′]cadmium(II)}, C26H26CdN4O4
  35. Crystal structure of poly[aqua(μ3-[2,2′-bipyridine]-3,3′-dicarboxylato-κ4N,N′:O:O′)zinc(II)] – dimethylformamide (1/1), C15H15N3O6Zn
  36. The crystal structure of poly[tetraaqua-tris(μ2-2,6-di(1H-imidazol-1-yl)naphthalene-κ2N:N′)-bis(thiophene-2,5-dicarboxylato-κ1O)]dicobalt(II), C30H24CoN6O6S
  37. Crystal structure of (S)-1-(5-(anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O
  38. Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
  39. Synthesis and crystal structure of μ-[1,1′-di(mesitylphosphanido)ferrocene]bis[η5-cyclopentadienylnickel(II)] tetrahydrofurane solvate, C42H48FeNi2OP2
  40. Synthesis and crystal structure of (E)-1-(4-(((E)-5-chloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15ClN2O2
  41. Crystal structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)nickel(II), C24H22N8O4S2Ni
  42. Crystal Structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)copper(II), C24H22N8O4S2Cu
  43. Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O,O′:O′′:O′′′}sodium(I)] monohydrate, C21H22NNaO11S
  44. Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
  45. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ2S:S′) bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dizinc(II), C28H56N4S8Zn2
  46. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ3S,S′:S)bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dicadmium(II), C28H56Cd2N4S8
  47. Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
  48. Crystal structure of 7-(4-methylphenyl)imidazo[1,2-a][1,3,5]triazin-4-amine, C12H11N5
  49. Crystal structure of the co-crystal O-isopropyl phenylcarbamothioate – 4,4′-bipyridine (2/1), C15H17N2OS
  50. Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
  51. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-di(ethanol)-bis{μ2-5-(N,N′-diethylamine)-5′-methoxyl-2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato-κ6O:O,N,N,O′:O′}trinickel(II) – ethanol – acetonitrile (1/2/2), C58H86Ni3N8O18
  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
Heruntergeladen am 21.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2017-0327/html
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