Startseite Crystal structure of chlorido-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)(η6-1-isopropyl-4-methyl benzene) ruthenium (II) tetrafluoroborate, C22H22Cl3N2BF4Ru
Artikel Open Access

Crystal structure of chlorido-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)(η6-1-isopropyl-4-methyl benzene) ruthenium (II) tetrafluoroborate, C22H22Cl3N2BF4Ru

  • Joel M. Gichumbi , Bernard Omondi EMAIL logo und Holger B. Friedrich
Veröffentlicht/Copyright: 25. Februar 2017

Abstract

C22H22Cl3N2BF4Ru, monoclinic, P21/n (no. 14), a = 15.067(5) Å, b = 10.409(5) Å, c = 16.503(5) Å, β = 112.75(5)°, V = 2386.9(16) Å3, Z = 4, Rgt(F) = 0.0211, wRref(F2) = 0.0535, T = 173 K.

CCDC no.:: 1529917

The 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:Orange block
Size:0.39 × 0.31 × 0.22 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:10.4 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:57°, >99%
N(hkl)measured, N(hkl)unique, Rint:50255, 6008, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5533
N(param)refined:301
Programs:Bruker programs [11], SHELX [12], WinGX/ORTEP [13]
Table 2:

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

AtomxyzUiso*/Ueq
C10.21141(13)0.63994(17)−0.09754(11)0.0234(3)
H10.15830.5863−0.12910.028*
C20.23480(15)0.74018(18)−0.14118(12)0.0277(4)
H20.19880.753−0.20220.033*
C30.31037(14)0.82133(17)−0.09604(12)0.0250(4)
H30.32760.8893−0.12560.03*
C40.36081(12)0.80160(16)−0.00646(11)0.0194(3)
H40.41180.85740.02680.023*
C50.33509(11)0.69879(15)0.03322(10)0.0150(3)
C60.38313(11)0.66695(15)0.12561(10)0.0155(3)
H60.4350.71670.16440.019*
C70.39260(11)0.52476(14)0.24115(10)0.0154(3)
C80.48662(12)0.47874(16)0.27928(11)0.0186(3)
C90.52027(12)0.42681(17)0.36334(11)0.0222(3)
H90.58440.39550.38920.027*
C100.46092(13)0.42046(16)0.40955(11)0.0219(3)
H100.48340.38310.46650.026*
C110.36818(12)0.46926(15)0.37179(11)0.0189(3)
C120.33277(12)0.52001(15)0.28782(10)0.0169(3)
H120.26860.55120.26230.02*
C130.15081(12)0.32224(15)0.09941(12)0.0205(3)
C140.10672(11)0.34744(15)0.00667(12)0.0207(3)
H140.04110.387−0.0180.025*
C150.16007(11)0.33919(15)−0.04623(11)0.0180(3)
H150.13130.3739−0.10740.022*
C160.26086(11)0.30995(14)−0.00944(10)0.0161(3)
C170.30399(11)0.28527(14)0.08165(10)0.0160(3)
H170.37570.28070.11060.019*
C180.24886(12)0.28986(15)0.13521(11)0.0185(3)
H180.28360.29040.20050.022*
C190.09392(15)0.33736(18)0.15615(15)0.0320(4)
H19A0.04590.26870.14280.048*
H19B0.06140.42090.14450.048*
H19C0.13740.33230.21820.048*
C200.31647(12)0.30557(16)−0.06865(11)0.0208(3)
H200.28120.3583−0.12210.025*
C210.31846(14)0.16538(19)−0.09741(13)0.0295(4)
H21A0.35130.1119−0.04560.044*
H21B0.35290.1605−0.1370.044*
H21C0.25240.1345−0.1280.044*
C220.41840(14)0.35841(19)−0.02477(14)0.0306(4)
H22A0.41590.446−0.0040.046*
H22B0.44930.3594−0.06730.046*
H22C0.45560.30370.02520.046*
N10.35118(9)0.56710(12)0.15188(8)0.0139(2)
N20.26190(9)0.61693(12)−0.01196(8)0.0155(2)
F10.62155(9)0.06708(13)0.24436(7)0.0377(3)
F20.51661(9)−0.09791(11)0.21417(8)0.0358(3)
F30.49351(9)0.06110(13)0.11327(7)0.0388(3)
F40.47140(12)0.10205(15)0.23940(10)0.0573(4)
Cl10.14454(3)0.63747(4)0.09854(3)0.01937(8)
Cl20.29362(3)0.46504(4)0.42968(3)0.02548(9)
Cl30.56157(3)0.47832(5)0.22160(3)0.02758(9)
Ru10.23352(2)0.47333(2)0.06252(2)0.01190(4)
B10.52450(15)0.0343(2)0.20233(13)0.0242(4)

Synthesis and crystallization

To a suspension of [(η6-p-cymene)Ru(μ –Cl)Cl]2 (0.2 mmol) in methanol (20 mL) was added 2,5-dichlorophenyl(pyridin-2-yl) methylene amine (0.42 mmol). The mixture was stirred at room temperature for 3 h followed by the reduction of the solvent volume in vacuo to about (10 mL) before adding NaBF4 (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 were obtained by slow diffusion of hexane in a solution of the title compound in acetone over 2 days.

Orange crystals, yield 82%, m.p. 210 °C decomp. 1H-NMR (400 MHz, DMSO-d6). δ: 9.67 (d, JHH = 5.4 Hz 1H, py); 9.08 (s, 1H, CH = N); 8.37 (t, 2H, py); 7.99 (m, 1H, py); 7.88 (t, 2H, Ar), 7.68 (m, 1H, Ar); 6.07 (d, JHH = 6.28 Hz, 1H, (p-cyAr)); 5.83 (d,JHH = 6.32 Hz, 1H, (p-cyAr)); 5.80 (d, JHH = 6.2 Hz, 1H, (p-cyAr)), 5.50 (d, JHH = 6.12 Hz, 1H, (p-cyAr)), 2.64 (m, 1H, CH(Me)2); 2.09 (s, 3H, (p-cyMe)); 1.028 (d, JHH = 6.88 Hz, 3H, (p-cyMe); 0.94 (d, JHH = 6.88 Hz, 3H, (p-cyMe). 13C-NMR (400 MHz, DMSO-d6). δ: 173.64 (CH = N); 156.37 (py); 153.55 (py); 149.41 (py); 140.33 (py); 130.18 (py); 132.37 (Ar); 132.22 (Ar); 130.05 (Ar); 124.11 (Ar); 106.38 (Ar); 101.63 (Ar); 87.04 p-cyAr); 85.83 (p-cyAr); 83.9 (p-cyAr); 30.47 (p-cyiPro); 21.74 (p-cyMe); 21.20 (p-cyMe); 18.07 (p-cyMe). IR (solid state): γ (C = N) 1612.1 cm−1. MS (ESI, M/Z): 520.98 [C22H22Cl3N2Ru]+

Experimental details

The methyl groups were idealized and refined using rigid groups allowed to rotate about the C—C bond (AFIX 137 option of the SHELXL-2013 program [12]). The Uiso values of the hydrogen atoms of methyl groups and the aromatic protons were set to 1.5Ueq(C). All other hydrogen atoms were also included using a riding model.

Discussion

Piano-stool complexes have applications in catalysis, supramolecular assemblies, molecular devices and have shown antiviral, antibiotic and anticancer activities [1, 2] . Three-legged piano stool complexes of Ru possess a pseudo octahedral geometry at the ruthenium atom arene ligand occupying three coordinating sites (the seat) with three other ligands. Their unique properties, which includes the mild reaction conditions required for their synthesis, high yields and good stability and solubility under aqueous conditions have enabled them be of interest in organometallic chemistry [3]. The coordinated arene ligands are relatively inert towards substitution and act as spectator ligands [3]. They stabilize and protect the metal centre and thereby prevent rapid oxidation of the Ru(II) to Ru(III) [4].

The title compound is part of our continuing studies of half-sandwich ruthenium(II) complexes [5], [6], [7], [8], in which the cationic species of the complex feature the known “pseudo-octahedral three-legged piano stool” structure. As expected, the ruthenium centre is coordinated to the N,N′-bidentate ligand through the nitrogen atoms and the chlorido ligand and the three atoms serve as the base of the piano stool. The p-cymene ring occupies the remaining coordination sites of the Ru(II) center and serve as the seat of the stool. The Ru—N bond lengths are 2.061(15) and 2.082(15) Å. These values are comparable to those reported for other arene ruthenium complexes with N,N′-ligands [5], [6], [7]. The N—Ru—N bond angles are 76.48(6)° while the N—Ru—Cl bond angles are 83.89(5) and 84.05(5)° and are also close to those values reported for related compounds [5; 6; 7, 9, 10].

Acknowledgement

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: 2016-8-22
Accepted: 2017-1-31
Published Online: 2017-2-25
Published in Print: 2017-3-1

©2017 Joel M. Gichumbi et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. The crystal structure of triphenylphosphineoxide – 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione (2/1), C42H32Cl2O6P2
  3. Crystal structure of poly-[diaqua-[bis(μ2-hydroxy)-bis(μ4-3,4,5,6-tetrachlorophthalato-κ3O,O′:O′; κ2O′′:O′′′)dilanthanum(III)], C8H3Cl4LaO6
  4. Crystal structure of 1,1′-(3,4-diphenylthieno[2,3-b]thiophene-2,5-diyl)bis[1-phenyl-methanone], C32H20O2S2
  5. Crystal structure of 4a-hydroxy-9-(3,5-dibromo-phenyl)-3,4,4a,5,6,7,9,9a-octahydro-2H-xanthene-1,8-dione, C19H18Br2O4
  6. Crystal structure of 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl 2-((2-methyl-1-(3-methylbenzamido)propan-2-yl)thio)acetate, C34H49NO5S
  7. Crystal structure of pyridinium bis(naphthalane-2,3-diolato-κ2O,O′)borate monohydrate, C25H20BNO5
  8. 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)nickel(II), C72H52N4O8Ni2
  9. The crystal structure of 3-(2-acetyl-4-butyramido-phenoxy)-2-hydroxy-N-isopropylpropan-1-aminium tetraphenylborate, C42H49BN2O4
  10. Crystal structure of 4-bromobenzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C28H34BrN3S
  11. Crystal structure of poly-[(μ6-benzene-1,2,4,5-tetracarboxylato)-(μ2-1,2-bis(imidazol-1-ylmethyl)benzene)dicobalt(II)], Co2C24H16N4O8
  12. Crystal structure of catena-(bis(μ2-1, 2-bis(imidazole-1-ylmethyl)benzene-κN:N′)-dichlororido-nickel(II)), C28H28Cl2N8Ni
  13. Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(4-methoxyphenyl)prop-2-en-1-one, C15H16N2O3
  14. Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-phenylprop-2-en-1-one, C14H14N2O2
  15. Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H18O4
  16. Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-(4-ethoxyphenyl)-3-hydroxyprop-2-en-1-one, C16H18N2O3
  17. Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(p-toly)prop-2-en-1-one, C15H16N2O2
  18. Crystal structure of 1-acetyl-3-(3-chlorophenyl)-5-(4-isopropylphenyl)-4,5-dihydro-(1H)-pyrazole, C20H21ClN2O
  19. The crystal structure of 1-methyl-2,4-dinitro-5-iodoimidazole, C4H3IN4O4
  20. The crystal structure of 4-chloro-3,5-dinitroaniline, C6H4ClN3O4
  21. Crystal structure of N,N-dimethyl-N′-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)formimidamide, C14H18N4OS
  22. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis[μ3-4-chloro-2,6-bis((methylimino)methyl)phenolato-κ2N,O:O,N′]-(μ4-oxido)tetracopper(II), C28H32Cl2Cu4N4O11
  23. Crystal structure of catena-poly[diaqua-bis(μ2-ethane-1,2-diyl-bis(pyridine-3-carboxylate-κ2N:N′))copper(II)] dinitrate, C28H28CuN6O16
  24. Synthesis and crystal structure of catena-poly[(μ2-nicotinato-κ2O,O′: κ1N)-(nitrato-κ1O)-(bis(2-benzimidazol-ylmethyl)amine-κ3N,N′,N′′)lead(II)], C22H18N7O5Pb
  25. The twinned crystal structure of (4SR)-7-benzyl-2,4,8,8-tetramethyl-7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione, C16H20N4O2
  26. Crystal structure of (Z)-3-hydroxy-3-(4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one, C15H13NO3
  27. Crystal structure of 2-amino-4-(2,3-dichlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12Cl2N2O2
  28. Crystal structure of catena-poly[(μ2-butane-1,4-diyl-bis(pyridine-3-carboxylato-κN))silver(I)] tetrafluoroborate, C16H16AgN2O4BF4
  29. Crystal structure of poly[diaqua-(1,10-phenanthroline-κ2N,N′)-(μ2-2,5-dihydroxytere-phthalato)-bis(μ4-2,5-dihydroxyterephthalato)dicerium(III)], C24H16CeN2O10
  30. Crystal structure of 5,7,4′-trihydroxy-3,8,3′-trymethoxyflavone, C18H16O8
  31. Crystal structure of N-(3,4-dichlorobenzylidene)-4-methylaniline, C14H11Cl2N
  32. Crystal structure of 4-(3-Methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester, C22H27NO4
  33. Crystal structure of 2-amino-4-(3-fluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13FN2O2
  34. Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C10H6Br2O4S2
  35. The crystal structure of N,N′-(4,4′-oxydibenzyl)-bisisonicotinamide 3.5 hydrate, C24H24N4O6
  36. Crystal structure of catena-poly[hexakis(μ2-chlorido)-hexakis(4-(1H-pyrazol-5-yl)pyridine-κN)tricadmium(II)], Cd3C48H42Cl6N18
  37. Crystal structure of 2-(4-(dimethylamino)phenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C21H22I1N3
  38. Crystal structure of 4-(1,3-dimethyl-2,3-dihydro-1H-perimidin-2-yl)benzonitrile, C20H17N3
  39. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis(2,2′-sulfonyldipyrazine-κ1N)dicopper(II), C24H24Cu2N8O12S2
  40. Crystal structure of 1-(4-chlorophenyl)-6,8-diphenyl-1H-pyrazolo[4,3-c]quinoline, C28H18ClN3
  41. Crystal structure of methyl 3-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-naphthoate, C24H21N3O5
  42. Crystal structure of (tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′′)-chloranilato-κO,O′-zinc(II) – methanol (1/1), C25H22Cl2N4O5Zn
  43. Crystal structure of 1,1-dimethyl-3-(4-methoxyphenyl)urea, C10H14N2O2
  44. Crystal structure of 4a-Hydroxy-9-(2-nitro-phenyl)-3,4,4a,5,6,7,9,9a-octahydro-2H-xanthene-1,8-dione, C19H19NO6
  45. Crystal structure of chlorido-(η6–1-isopropyl-4-methyl benzene)-(1-(pyridin-2-yl)-N-(p-tolyl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C23H26ClF6N2PRu
  46. Crystal structure of phenyl(2-phenyl-2,3-dihydro-1H-perimidin-2-yl)methanone, C24H18N2O
  47. Crystal structure of (E)-3-methyl-4-((3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one, C29H23N7O
  48. Crystal structure of 2-(4-(2-butyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)piperazin-1-yl)-2-oxoethyldiethylcarbamodithioate, C27H34N4O3S2
  49. Crystal structure of poly-[diaqua-bis(μ-4,4′-bipyridine-κ2N:N′)cobalt(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2), C42H40Cl2CoN6O10S2
  50. Crystal structure of (η6-benzene)-(N-(2,6-dimethylphenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate monohydrate, C20H20Cl2N2O5Ru
  51. Crystal structure of 4,10,16,22-tetrahydroxy-6,12,18,24-tetramethoxy-2,8,14,20-tetraethylphenylresorcin[4]arene – ethyl acetate (1/1), C68H72O10
  52. Crystal structure of chlorido-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)(η6-1-isopropyl-4-methyl benzene) ruthenium (II) tetrafluoroborate, C22H22Cl3N2BF4Ru
  53. Crystal structure of 3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde, a rare Z′ = 3 structure, C20H17N5O
  54. Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-1,3,4-thiadiazol-2-amine, C23H16ClN5S
  55. Crystal structure of 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one-N,N-dimethylformamide (1/1), C18H17NO5
  56. Crystal structure of halogen-bonded 2-chloro-1,10-phenanthroline—1,4-diiodotetrafluorobenzene (2/1), C30H14Cl2F4I2N4
  57. Crystal structure of 1-(4,4-dimethyl-2,6-dithioxo-1,3,5-triazinan-1-yl)-3-(diethylaminocarbonyl)thiourea, C11H20N6OS3
  58. Crystal structure of methyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C18H15FN2O2
  59. Crystal structure of 1,1-dimethyl-3-(4-methylphenyl)urea, C10H14N2O
  60. Crystal structure of yttrium gallium antimonide, Y5Ga1.24Sb2.77
  61. Crystal structure of 2-(bis(4-methoxyphenyl)amino)-2-oxoacetic acid, C16H15NO5
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