Startseite Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14
Artikel Open Access

Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14

  • Peizhi Wang EMAIL logo , Peiyu Wang und Ming Bai
Veröffentlicht/Copyright: 23. März 2018

Abstract

C17H56B2N2O14, monoclinic, P21/c (no. 14), a = 14.3049(6) Å, b = 14.5382(7) Å, c = 15.0065(7) Å, β = 103.185(3)°, V = 3038.6(2) Å3, Z = 4, Rgt(F) = 0.0556, wRref(F2) = 0.1836, T = 296(2) K.

CCDC no.:: 1824796

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

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.51 × 0.42 × 0.38 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.0 cm−1
Diffractometer, scan mode:Bruker CCD, φ and ω
2θmax, completeness:55°, >99%
N(hkl)measured, N(hkl)unique, Rint:16461, 6922, 0.032
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4322
N(param)refined:367
Programs:SADABS [1], SHELX [2], Bruker programs [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.79334(16)0.20899(16)0.02193(16)0.0685(6)
H1A0.84030.16420.01220.082*
H1B0.74530.17630.04600.082*
N10.84290(10)0.27691(10)0.09287(11)0.0479(4)
O10.31306(9)0.00102(10)0.07003(8)0.0559(4)
O1W0.10356(16)0.4933(2)0.1582(2)0.1412(12)
H1WA0.148(2)0.518(3)0.198(3)0.212*
H1WB0.0492(16)0.514(3)0.163(4)0.212*
B10.09669(15)0.00990(15)0.12558(14)0.0449(5)
N20.32973(11)0.22341(10)0.87185(11)0.0503(4)
O20.46194(9)0.01154(11)0.15217(8)0.0574(4)
O2W0.73286(11)0.06453(16)0.23149(12)0.0856(6)
H2WA0.7013(19)0.067(3)0.1760(8)0.128*
H2WB0.6936(18)0.055(3)0.2656(17)0.128*
C20.7457(2)0.2496(3)−0.0685(2)0.1154(12)
H2A0.71610.2015−0.10920.173*
H2B0.69750.2928−0.06030.173*
H2C0.79270.2806−0.09420.173*
B20.54853(14)0.00945(15)0.38186(13)0.0425(4)
C30.91710(16)0.33208(17)0.05817(17)0.0695(6)
H3A0.88420.36890.00660.083*
H3B0.94810.37410.10610.083*
O30.34043(8)0.00924(10)0.22129(8)0.0507(3)
O3W0.80495(12)0.93980(14)0.47664(12)0.0779(5)
H3WA0.8311(19)0.966(2)0.4377(18)0.117*
H3WB0.7484(11)0.962(2)0.469(2)0.117*
C40.99350(18)0.2764(2)0.0289(2)0.0937(9)
H4A1.03700.31690.00810.141*
H4B1.02810.24100.07980.141*
H4C0.96410.2357−0.01990.141*
O40.12762(9)−0.00504(10)0.04862(9)0.0550(4)
H40.1888(7)−0.0065(17)0.0570(18)0.083*
O4W0.39566(11)0.92532(12)0.93726(10)0.0645(4)
H4WA0.3843(18)0.9501(18)0.9852(13)0.097*
H4WB0.4445(13)0.9498(18)0.9252(18)0.097*
C50.89022(16)0.22149(15)0.17669(16)0.0640(6)
H5A0.84130.18510.19560.077*
H5B0.93560.17910.15960.077*
O50.15703(9)0.01917(13)0.20915(9)0.0692(5)
H50.2182(8)0.015(2)0.214(2)0.104*
O5W0.07435(12)0.07431(14)0.35216(11)0.0785(5)
H5WA0.099(2)0.054(2)0.3097(14)0.118*
H5WB0.1088(19)0.063(2)0.4046(9)0.118*
C60.9422(2)0.2774(2)0.25723(19)0.1044(10)
H6A0.96980.23700.30690.157*
H6B0.99220.31240.24010.157*
H6C0.89780.31840.27610.157*
O60.00081(9)0.01707(13)0.12269(10)0.0670(4)
H6−0.0375(18)0.012(2)0.0706(11)0.100*
C70.77162(15)0.34436(15)0.11630(16)0.0617(5)
H7A0.80630.38750.16120.074*
H7B0.74320.37910.06160.074*
O70.58139(10)0.01172(13)0.30520(9)0.0702(5)
H70.5399(17)0.011(2)0.2546(12)0.105*
O80.61543(9)0.01024(11)0.46357(9)0.0573(4)
H80.5942(18)0.0028(17)0.5121(12)0.086*
C80.69235(18)0.30268(19)0.1532(2)0.0843(8)
H8A0.65100.35050.16600.126*
H8B0.65600.26120.10870.126*
H8C0.71930.26970.20850.126*
C90.41160(18)0.17226(18)0.8477(2)0.0797(7)
H9A0.38590.12920.79890.096*
H9B0.44400.13680.90060.096*
O90.45376(8)0.00604(10)0.38185(8)0.0482(3)
H90.4178(15)0.0035(16)0.3281(9)0.072*
C100.4848(2)0.2331(3)0.8175(3)0.1158(12)
H10A0.53470.19550.80330.174*
H10B0.45400.26730.76420.174*
H10C0.51220.27500.86590.174*
C110.36487(17)0.28704(15)0.95156(15)0.0650(6)
H11A0.30990.31860.96500.078*
H11B0.40580.33320.93340.078*
C120.4199(2)0.2414(2)1.03840(19)0.0994(9)
H12A0.43930.28701.08520.149*
H12B0.37960.19681.05830.149*
H12C0.47570.21141.02670.149*
C130.26188(17)0.15157(16)0.89619(18)0.0702(6)
H13A0.23800.11350.84280.084*
H13B0.29830.11220.94380.084*
C140.17776(18)0.1893(2)0.9281(2)0.0873(8)
H14A0.13930.13950.94180.131*
H14B0.20020.22570.98220.131*
H14C0.13980.22700.88090.131*
C150.27718(18)0.28342(17)0.79418(16)0.0693(6)
H15A0.22500.31430.81340.083*
H15B0.32100.33040.78220.083*
C160.2367(3)0.2323(3)0.7063(2)0.1162(12)
H16A0.20460.27490.66050.174*
H16B0.28800.20280.68560.174*
H16C0.19190.18670.71680.174*
C170.37179(12)0.00750(12)0.14750(11)0.0398(4)

Source of materials

The title compound was prepared by accident. Firstly, an aromatic acid (A. R.), boric acid (A. R.) and tetramethylammonium (25% aqueous solution, C. R.) were dissolved in small amount of H2O/EtOH (v/v, 2:1) with the molar ratio of 1:2:2 to evaporate under room temperature to prepare the cocrystal of the related acid. About after 14 days, colorless block crystals appeared in the clean solution. Determined by single crystal X-ray diffraction, the crystal was proved to be the title compound. At the same time, it can be concluded that carbonate should be derived from the vigorous stirring during the experiment.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The H atoms bonded to C were localized in the ideal positions and all H atoms bonded to O atoms were refined with the O—H distance restrained to 0.86 Å. The Uiso values of the hydrogen atoms bonded to O were set to 1.5Ueq(O).

Comment

Boric acid is a triangular planar molecule with hydrogen bond donors and acceptors due to its three hydroxyl groups. Meanwhile, carbonate is also a perfect triangular planar ion that can act as hydrogen bond donor. Searching in the related literature, it can be found that boric acid can interact with tetraalkylammonium, such as tetraethylammonium, to form the stable crystal structure [4], and tetraethylammonium bicarbonate is also known [5]. Interestingly, in the actual experiment, the crystal structure composed of tetraethylammonium carbonate and boric acid has been prepared, which has two neutral boric acid molecules, one carbonate anion, five water molecules and two tetraethylammonium cations. Herein we reported the new structure to further explore the packing rules of triangular planar molecules and tetraalkylammonium.

In the asymmetric unit of the title compound, there are two boric acid molecules, one carbonate dianion, five water molecules and two counterions of tetraethylammonium cations. It can be clearly found that the neutral acid molecules can connect with the carbonate ion to form the acid-anion unit by several O—H⋯O hydrogen bonds, then the unit can further link five crystallographically independent water molecules to produce 2D layers in tha ac plane. Each carbonate anion accepts six hydrogen bonds. One crystallographic boric acid molecule (B1) is involved in five, the other one (B2) in six hydrogen bonds. Each of the five water molecules is involved in three hydrogen bonds. The interlayer distance between the hydrogen bonded layers is about b/2 = 7.27 Å. To form the final stable structure, two independent tetraethylammonium ions are contained between the layers to yield the neutral structure. Bond lengths and angles of the ions and molecules are in the expected ranges [6, 7] .

Acknowledgements

This work was financially supported by the first batch of traditional Chinese Medicine School inheritance studio program of State Administration of Traditional Chinese Medicine: Henan Shaw acupuncture Schools inheritance studio (The traditional Chinese medicine-2012-228). The author thanks the referees and the members of the editorial office for their very helpful critical comments on the first draft.

References

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Received: 2017-8-9
Accepted: 2018-2-20
Published Online: 2018-3-23
Published in Print: 2018-5-24

©2018 Peizhi Wang 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
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