Startseite Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
Artikel Open Access

Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5

  • Su Wenhui , Tian Dayong , Yu Zhichao , Yang Liguo EMAIL logo und Niu Yongsheng
Veröffentlicht/Copyright: 17. September 2019

Abstract

C21H26N2O5, monoclinic, P21/c (no. 14), a = 19.779(9) Å, b = 5.332(2) Å, c = 18.945(8) Å, β = 94.572(6)°, V = 1991.4(15) Å3, Z = 4, Rgt(F) = 0.0425, wRref(F2) = 0.1179, T = 298(2) K.

CCDC no.: 1949156

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.

Source of material

The title molecule was synthesized by refluxing 1,3-diamino-2-propanol (0.09 mL, 1 mmol) and 3-ethoxy salicylaldehyde (0.332 g, 2 mmol). The yield is ca. 32%. IR(KBr): 3412(s), 1638(s), 1518(s), 1497(s), 1448(s), 1356(s), 1245(s), 1174(s), 1113(s), 1073(s), 1005(s), 924(s), 894(s), 835(m), 773(m), 716(m), 619(m), 493(m) cm−1. Elemental analysis: Found: C, 65.25; H, 6.70; N, 7.21%. Calcd for C21H26N2O5: C, 65.28; H, 6.73; N, 7.25%.

Table 1:

Data collection and handling.

Crystal:White block
Size:0.10 × 0.08 × 0.06 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:16810, 3526, 0.038
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2346
N(param)refined:257
Programs:Bruker [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.31435(7)0.2870(3)0.60410(7)0.0610(4)
N10.52833(8)0.8150(3)0.58091(10)0.0586(5)
H10.50590.72410.54970.070*
C10.23404(12)−0.0447(4)0.58256(11)0.0741(7)
H1A0.21010.03580.54270.111*
H1B0.2037−0.15390.60510.111*
H1C0.2710−0.14080.56670.111*
O20.42466(7)0.5094(3)0.55743(7)0.0631(4)
N20.76797(8)0.6324(3)0.63258(9)0.0621(5)
C20.26117(10)0.1503(4)0.63441(10)0.0621(6)
H2A0.22510.26410.64510.075*
H2B0.27870.07060.67810.075*
O30.63832(8)0.4672(2)0.57454(7)0.0660(4)
H30.63000.47330.53150.099*
C30.34677(10)0.4640(4)0.64696(10)0.0535(5)
O40.82058(7)0.4227(3)0.74802(7)0.0702(4)
H40.79750.52250.72360.105*
C40.32721(11)0.5374(4)0.71165(10)0.0618(5)
H4A0.28980.46130.72930.074*
O50.89746(7)0.0757(3)0.81068(7)0.0701(4)
C50.36232(12)0.7251(4)0.75209(12)0.0687(6)
H50.34810.77170.79580.082*
C60.41678(12)0.8368(4)0.72701(12)0.0674(6)
H60.43950.96230.75350.081*
C70.43987(10)0.7650(3)0.66044(11)0.0568(5)
C80.40500(10)0.5759(3)0.61793(10)0.0534(5)
C90.49964(11)0.8726(4)0.63798(12)0.0602(5)
H90.52040.99630.66670.072*
C100.59624(10)0.8948(3)0.56642(11)0.0577(5)
H10A0.60481.06260.58480.069*
H10B0.60010.89830.51570.069*
C110.64832(9)0.7127(3)0.60141(10)0.0514(5)
H110.64190.70820.65220.062*
C120.71992(10)0.8002(4)0.59315(12)0.0658(6)
H12A0.72850.80020.54340.079*
H12B0.72570.97010.61100.079*
C130.80356(10)0.4834(4)0.59795(11)0.0598(5)
H130.80020.49390.54880.072*
C140.84919(9)0.2976(4)0.63202(10)0.0533(5)
C150.88667(10)0.1361(4)0.59163(11)0.0624(6)
H150.88390.15260.54260.075*
C160.92722(11)−0.0451(4)0.62348(11)0.0677(6)
H160.9517−0.15110.59600.081*
C170.93230(10)−0.0724(4)0.69700(11)0.0634(6)
H170.9600−0.19680.71810.076*
C180.89646(9)0.0840(4)0.73848(10)0.0553(5)
C190.85480(9)0.2728(4)0.70592(10)0.0539(5)
C200.93531(11)−0.1217(4)0.84632(11)0.0700(6)
H20A0.9828−0.10950.83740.084*
H20B0.9183−0.28360.82960.084*
C210.92702(13)−0.0933(5)0.92422(11)0.0879(8)
H21A0.94560.06480.94040.132*
H21B0.9505−0.22700.94970.132*
H21C0.8797−0.09960.93210.132*

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5 Ueq(C). The O- and N-bound H atoms were located in a difference Fourier map but were refined with a distance restraint of N—H = 0.88 ± 0.01 Å, and with Uiso(H) set to 1.2 Ueq(N) [3].

Comment

There are several complexes containing the deprotonated title molecule as an anionic ligand, which have been reported, however, the structure about this ligand has not been reported [4], [5], [6].

The compound crystallizes in the monoclinic space group P21/c with four formula units in the unit cell. As shown in the figure, each molecule formally consists of two 3-ethoxysalicylidenyl and one 2-hydroxyl-1,3-propanediamine-diyl moieties. It is observed that the phenolic proton is transferred to the imine nitrogen in the structure of this molecule to yield a ylidic structure. The NH group and phenolate O atom form a strong intramolecular N—H⋯O hydrogen bond. The N—H⋯O hydrogen-bonded rings are almost planar and coupled with the cyclohexadiene rings [7], [8].

Acknowledgements

This work was supported by Henan science and technology project (Nos. 192102310232), Key discipline of environmental engineer of Anyang Institute of Technology.

References

1. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2005).Suche in Google Scholar

2. Sheldrick, G. M.: SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Suche in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

4. Biswas, D.; Chakrabarty, P. P.; Saha, S.; Jana, A. D.; Schollmeyer, D.; Granda, S.: Ligand mediated structural deversity and role of different weak interactions in molecular self-assembly of a series of copper(II)-sodium(I) schiff-base heterometallic complexes. Inorg. Chim. Acta 408 (2013) 172–180.10.1016/j.ica.2013.09.011Suche in Google Scholar

5. Tsuchimoto, M.; Ishii, T.; Imaoka, T.; Yamamoto, K.; Yoshioka, N.; Sunatsuki, Y.: Synthesis and structure of vanadium-cerium trinuclear complexes with Schiff-base ligands. Bull. Chem. Soc. Jpn. 79 (2006) 1393–1397.10.1246/bcsj.79.1393Suche in Google Scholar

6. Tsuchimoto, M.; Ishii, T.; Imaoka, T.; Yamamoto, K.: Synthesis and electrochemical properties of oxovanadium complexes with a pentadentate Schiff base ligand. Bull. Chem. Soc. Jpn. 77 (2004) 1849–1854.10.1246/bcsj.77.1849Suche in Google Scholar

7. Odabasoglu, M.; Albayrak, C.; Buyukgungor, O.; Lonnecke, P.: 2-{[Tris (hydroxymethyl)methyl]amino-methylene}cyclohexa-3,5-dien-1(2H)-one and its 6-hydroxy and 6-methoxy derivatives. Acta Crystallogr. C59 (2003) o616–o619.10.1107/S0108270103020997Suche in Google Scholar

8. Dey, M.; Rao, C. P.; Saarenketo, P. K.; Rissanen, K.; Kolehmainen, E.; Guionneau, P.: Mn(IV) and Co(III)-complexes of –OH-rich ligands possessing O2N, O3N and O4N cores: syntheses, characterization and crystal structures. Polyhedron 22 (2003) 3515–3521.10.1016/j.poly.2003.09.015Suche in Google Scholar

Received: 2019-07-03
Accepted: 2019-08-25
Published Online: 2019-09-17
Published in Print: 2019-12-18

©2019 Su Wenhui et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. 10.1515/ncrs-2020-frontmatter1
  2. The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
  3. The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
  4. Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
  5. Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
  6. The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
  7. Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
  8. Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  9. Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
  10. The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
  11. Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
  12. Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
  13. The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
  14. Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
  15. The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
  16. The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
  17. The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
  18. The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
  19. Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
  20. Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
  21. The crystal structure of catena-poly2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
  22. Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
  23. Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
  24. Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
  25. Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
  26. Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
  27. Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
  28. Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
  29. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
  30. The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
  31. Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
  32. Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
  33. Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
  34. Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
  35. The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
  36. Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
  37. Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
  38. Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
  39. Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
  40. Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
  41. Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
  42. Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
  43. Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
  44. Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
  45. Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
  46. Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
  47. Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
  48. Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
  49. Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
  50. Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
  51. Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
  52. Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
  53. Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
  54. Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
  55. Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
  56. Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
Heruntergeladen am 18.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2019-0468/html?lang=de
Button zum nach oben scrollen