Startseite Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
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Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2

  • Wen-Ze Zhao ORCID logo EMAIL logo und Hua Tian
Veröffentlicht/Copyright: 2. November 2023

Abstract

C24H50N8O18S2Zn2, triclinic, P1̄ (no. 2), a = 7.9797(5) Å, b = 10.4923(6) Å, c = 11.4835(7) Å, α = 97.512(2)°, β = 100.089(2)°, γ = 94.156(2)°, V = 933.98(10) Å3, Z = 1, Rgt(F) = 0.0382, wRref(F2) = 0.1202, T = 293(2) K.

CCDC no.: 2303478

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.20 × 0.17 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.48 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.0°, 97 %
N(hkl)measured, N(hkl)uniqueRint: 7866, 3200, 0.028
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2755
N(param)refined: 255
Programs: Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.2052 (5) −0.4475 (4) 0.5896 (4) 0.0425 (10)
H1 0.0954 −0.4273 0.5610 0.051*
C2 0.2347 (5) −0.5778 (4) 0.5857 (4) 0.0425 (10)
H2 0.1470 −0.6433 0.5554 0.051*
C3 0.3960 (5) −0.6048 (4) 0.6276 (4) 0.0400 (10)
H3 0.4182 −0.6906 0.6276 0.048*
C4 0.5280 (5) −0.5089 (4) 0.6702 (3) 0.0316 (8)
C5 0.4864 (5) −0.3818 (4) 0.6707 (3) 0.0320 (9)
H5 0.5725 −0.3147 0.6988 0.038*
C6 0.8346 (5) −0.4657 (4) 0.7694 (3) 0.0320 (9)
C7 1.1257 (5) −0.4551 (4) 0.8785 (4) 0.0359 (9)
H7A 1.0999 −0.4003 0.9467 0.043*
H7B 1.1717 −0.3995 0.8281 0.043*
C8 1.2589 (5) −0.5405 (4) 0.9221 (4) 0.0380 (9)
H8A 1.2782 −0.6010 0.8554 0.046*
H8B 1.2190 −0.5897 0.9795 0.046*
C9 1.4272 (5) −0.4587 (4) 0.9809 (4) 0.0395 (10)
H9A 1.4611 −0.4044 0.9252 0.047*
H9B 1.4086 −0.4026 1.0507 0.047*
C10 0.7090 (6) −0.1217 (5) 0.9892 (4) 0.0495 (12)
H10A 0.8070 −0.0984 1.0521 0.074*
H10B 0.6120 −0.1477 1.0226 0.074*
H10C 0.7317 −0.1920 0.9336 0.074*
C11 0.7904 (7) 0.1065 (5) 0.9626 (5) 0.0627 (15)
H11A 0.8761 0.0955 1.0295 0.094*
H11B 0.8442 0.1231 0.8969 0.094*
H11C 0.7282 0.1780 0.9847 0.094*
C12 0.5438 (5) −0.0197 (4) 0.8374 (3) 0.0348 (9)
H12 0.5293 0.0510 0.7967 0.042*
N1 0.6728 (4) −0.0108 (3) 0.9273 (3) 0.0386 (8)
N2 0.3258 (4) −0.3525 (3) 0.6321 (3) 0.0322 (7)
N3 0.6893 (4) −0.5447 (3) 0.7129 (3) 0.0359 (8)
H3A 0.7000 −0.6262 0.7029 0.043*
N4 0.9696 (4) −0.5265 (3) 0.8119 (3) 0.0358 (8)
H4 0.9629 −0.6094 0.7992 0.043*
O1 0.3017 (3) −0.1835 (2) 0.3221 (2) 0.0332 (6)
O2 0.1760 (3) 0.0086 (2) 0.3853 (2) 0.0311 (6)
O3 −0.0024 (3) −0.1750 (3) 0.2652 (2) 0.0352 (6)
O4 0.1210 (3) −0.1854 (2) 0.4695 (2) 0.0288 (6)
O5 0.4951 (4) −0.1289 (3) 0.5568 (3) 0.0333 (6)
H5A 0.4633 −0.1374 0.4806 0.050*
O6 0.2550 (4) 0.0506 (3) 0.6395 (3) 0.0321 (6)
H6A 0.1720 0.0833 0.6811 0.048*
O7 0.0580 (3) −0.1626 (3) 0.7150 (2) 0.0348 (6)
H7C 0.0078 −0.2409 0.7029 0.052*
H7D −0.0185 −0.1194 0.6783 0.052*
O8 0.4399 (3) −0.1170 (3) 0.8035 (2) 0.0334 (6)
O9 0.8409 (4) −0.3468 (2) 0.7824 (3) 0.0402 (7)
S1 0.14856 (11) −0.13440 (8) 0.35894 (8) 0.0251 (2)
Zn1 0.27788 (5) −0.15537 (4) 0.63905 (4) 0.02635 (17)
H6B 0.222 (5) 0.050 (4) 0.577 (4) 0.019 (11)*
H5B 0.581 (6) −0.092 (4) 0.576 (4) 0.032 (13)*

1 Source of materials

Weigh 3-isocyanatopyridine (1.20 g, 10 mmol) and hexane-1,6-diamine (0.46 g, 4.0 mmol) and put it into a 50 mL round-bottom flask. Add 30 mL of ethanol solution, heat it and reflux for 12 h, cool to room temperature, separate out white solid, filter, wash with a small amount of ethanol for three times, dry in the vacuum, and obtain 1.07 g of white solid. The yield is 70 %. Weigh 1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea) (0.18, 0.5 mmol) and dissolve it in 5 mL N,N–dimethylformamide. Weigh zinc(II) sulfate heptahydrate (0.29 g, 1 mmol) and dissolve it in 20 mL ethanol solution. Drop the ethanol solution into N,N–dimethylformamide, let it stand, evaporate naturally for 10 days, and separate out the crystal of X-ray diffraction with the suitable size.

2 Experimental details

Crystal data, data collection and structure refinement details are summarized in Table 1. Using Olex2 [1], the structure was solved using Charge Flipping and refined with the ShelXL [3] refinement. All hydrogen atoms were positioned geometrically, with the d(C–H) = 0.97–0.99 Å, Uiso(H) = 1.2 times Ueq(C) and Uiso(H) = 1.5 times Ueq(O).

3 Comment

As a hydrogen bond donor, carbamido can provide the Y-type hydrogen bonding point (O–S–O) of diproton and Y-type anion such as (AcO) or tetrahedral anion (such as SO42−), forming double hydrogen bonds [5]. At the same time, it is easy to form a hydrogen bond between carbamido and carbamido, and between carbamido and solvent molecules and assemble into the supramolecular compound with a novel structure [6]. Metal complexes containing carbamido are also an important category of anion receptors. It is possible to assemble simple monourea receptors into polyurea receptors with a special spatial configuration and pre-organize associated points to enhance the recognition of anions. For anion receptors based on metal coordination, the central metal coordinates with ligand and plays the role of pre-organized functional hydrogen [7]. The metal ions in the ds area have the electron configuration of d10 and different coordination numbers. They can use different coordination modes in the process of coordination with organic ligands and build complexes with diversified structures [8]. The nitrogen atoms on the pyridine ring have strong nucleophilic ability and may coordinate with transition metal ions and form complexes easily [9]. Therefore, we synthesized compounds containing carbamido and pyridine ring as functional groups. The title ligand is coordinated with Zn (II) ions to obtain Zn (II) complexes. The bond length and bond angle of the complexes are within the normal range. Each ligand coordinates with two Zn (II) ions as a bidentate ligand. Each Zn (II) ion coordinates with a nitrogen atom on the pyridine ring of the ligand, three oxygen atoms of water molecules, an oxygen atom of sulfate radical, and oxygen atom of N,N–dimethylformamide, forming a dinuclear complex. Different from the complex structure reported in the literature [10], two pyridine rings in the complex are completely parallel and the whole chain has a serrated structure. The coordinated water molecules in the complex and sulfate ions form intramolecular hydrogen bonds of O5–H5A⋯O1, O6–H6B⋯O2, and O6–H6B⋯O4, and intermolecular hydrogen bonds of O6–H6A⋯O3, O7–H7C⋯O9, and O5–H5B⋯O2. Nitrogen atoms and sulfate ions of carbamido form intermolecular hydrogen bonds of N3–H3A⋯O1 and N4–H4⋯O3.


Corresponding author: Wen-Ze Zhao, Shandong Vocational College of industry, Zibo, Shandong, 256414, People’s Republic of China, E-mail:

  1. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  2. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  3. Research funding:

References

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Received: 2023-07-19
Accepted: 2023-10-25
Published Online: 2023-11-02
Published in Print: 2023-12-15

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylatoκ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N,N )-(dihydrogen L-malate-κ2O,O )copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
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