Startseite The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
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The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br

  • Lehlohonolo Moherane ORCID logo EMAIL logo , Orbett T. Alexander ORCID logo , Hendrik G. Visser und Amanda-Lee E. Manicum ORCID logo
Veröffentlicht/Copyright: 30. Juni 2021

Abstract

C30H26N4O9Re2Br, triclinic, P1 (no. 2), a = 9.407(6) Å, b = 11.769(8) Å, c = 15.055(11) Å, α = 82.70(2)°, β = 76.68(3)°, γ = 77.364(2)°, V = 1577.5(19) Å3, Z = 2, R gt (F) = 0.0291, wR ref (F2) = 0.0868, T = 100 K.

CCDC no.: 2084390

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

fac-[NEt4]2[Re(CO)3(Br)3] (100 mg, 0.1298 mmol) was dissolved in water (20 mL) and added to 5,5′-dimethyl-2,2′-bipyridine (DMbpy) (47.92 mg, 0.2601 mmol) dissolved in ethanol (3 mL). The solution was stirred for 48 h and the solvent was filtered off. The yellow solid was washed with water, cold ethanol and petroleum ether and the product eluted in the filtrate. The product was evaporated, and recrystallized using DCM:hexane, 1:1. Crystals suitable for single crystal X-ray diffraction were obtained.

Yield: 68.8 mg, IR (ATR, cm−1): vCO = 2005.70, 1898.55, 1864.07.

Experimental details

The aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C–H = 0.95 and 0.98 Å and Uiso(H) = 1.5 Ueq(C) and 1.2 Ueq(C), respectively. The placement of the H atoms on the methyl groups was that of an idealised methyl group according to the electron-density map (HFIX 137). The highest peak is 1.8 e. Å−3 and deepest hole is 1.7 e. Å−3.

Comment

A variety of research groups are intensively focused on the organometallic synthon fac-[M(CO)3]+ (M = 188/186Re, 99mTc), predominantly on functionalized Re(I) compounds, which are used in the design of therapeutic and diagnostic radiopharmaceutical models [6]. These results propose the possibility of utilizing 99mTc- and Re-based complexes not only as radiotherapeutic agents but also as chemotherapeutic agents [7]. Recently, studies of alkoxo or amido complexes of low valent fragments of the group 8–10 transition metals have attracted interest [8]. Additionally, studies included a hydroxyl group, 2,2′-bipyridine and rhenium metal centers containing bridged complexes showing that these complexes possess incredible spectroscopic properties [9], [10], [11], [12], [13], [14], [15].

The title structure is comprised of two rhenium complexes bridged by one hydroxido ligand (O1, in the sixth axial position). The distorted octahedral geometry of the respective rhenium metal centers is completed by a 5,5′-dimethyl-2,2′-bipyridine bidentate ligand, and the three facially coordinated carbonyls. There is one bromide (Br1) ion balancing the charge of the complex and one half of a water (O5) molecule in the asymmetric unit cell. The placement of the H atom on the hydroxo bridge oxygen (O1) atom was achieved from an electron density map and its presence is corroborated by two long Re–O bonds [2.139(3) and 2.146(3) Å]. The two independent rhenium complexes bridged by a hydroxido ligand show the following Re-C bond lengths of Re1–C12, Re2–C11, Re1–C21, Re2–C22 and Re1–C32, Re2–C31 recording 1.909(40), 1.911(43), 1.909(48), 1.919(43), 1.900(49) and 1.905(51) Å, respectively. Amongst other hydrogen interactions, there is a classical OH···Br (O–H–X, 2.55(6) Å) hydrogen interaction between the hydrogen (H1) atom of the hydroxyl bridging group and the bromide (Br1) ion in the asymmetric unit cell.

Table 1:

Data collection and handling.

Crystal: Yellow plate
Size: 0.37 × 0.13 × 0.04 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 8.99 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint: 66,539, 7825, 0.075
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 7101
N(param)refined: 417
Programs: Bruker [1], SIR97 [2], WinGX [3], Shelx [4], Diamond [5]
Table 2:

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

Atom x y z Uiso*/Ueq
Re1 0.47912 (2) 0.76356 (2) 0.65205 (2) 0.01447 (6)
Re2 0.78173 (2) 0.78395 (2) 0.78668 (2) 0.01459 (6)
O1 0.2263 (4) 0.7703 (3) 0.8212 (2) 0.0303 (7)
O2 0.4463 (4) 1.0289 (3) 0.6515 (2) 0.0300 (7)
O3 0.2410 (4) 0.8437 (3) 0.5372 (2) 0.0290 (7)
O4 0.7785 (4) 0.9886 (3) 0.6391 (2) 0.0355 (8)
O5 1.0724 (3) 0.6629 (3) 0.6680 (2) 0.0306 (7)
O6 0.9493 (4) 0.9241 (3) 0.8701 (2) 0.0288 (7)
O7 0.6434 (3) 0.6990 (2) 0.73385 (18) 0.0170 (5)
H7 0.662 (6) 0.625 (5) 0.744 (4) 0.036 (15)*
N1 0.5052 (4) 0.5799 (3) 0.6341 (2) 0.0186 (6)
N2 0.6716 (4) 0.7262 (3) 0.5400 (2) 0.0173 (6)
N3 0.7681 (4) 0.6445 (3) 0.8959 (2) 0.0170 (6)
N4 0.5725 (4) 0.8418 (3) 0.8819 (2) 0.0150 (6)
C1 0.4138 (5) 0.5110 (4) 0.6834 (3) 0.0198 (7)
H1 0.331116 0.544999 0.727713 0.024*
C01 0.4641 (4) 0.9275 (4) 0.6549 (3) 0.0208 (8)
C02 0.3205 (5) 0.7703 (3) 0.7576 (3) 0.0205(8)
C2 0.4339 (5) 0.3931 (4) 0.6731 (3) 0.0269 (9)
C03 0.3329 (5) 0.8111(3) 0.5792(3) 0.0201(7)
C3 0.3305 (6) 0.3204 (4) 0.7355 (3) 0.0361 (11)
H3A 0.329946 0.251642 0.705180 0.054*
H3B 0.229437 0.367336 0.749008 0.054*
H3C 0.365355 0.295167 0.792773 0.054*
C04 0.7781 (5) 0.9101 (4) 0.6933 (3) 0.0220 (8)
C4 0.5537 (6) 0.3460 (4) 0.6081 (3) 0.0289 (10)
H4 0.570375 0.265460 0.598535 0.035*
C05 0.9633 (5) 0.7092 (3) 0.7113 (3) 0.0190 (7)
C5 0.6495 (5) 0.4142 (4) 0.5567 (3) 0.0247 (8)
H5 0.732036 0.381483 0.511741 0.030*
C06 0.8893 (4) 0.8678 (4) 0.8393 (3) 0.0204 (8)
C6 0.6236 (4) 0.5321 (3) 0.5718 (2) 0.0181 (7)
C7 0.7195 (4) 0.6126 (3) 0.5213 (3) 0.0186 (7)
C8 0.8483 (5) 0.5789 (4) 0.4570 (3) 0.0267 (9)
H8 0.880988 0.499117 0.444656 0.032*
C9 0.9301 (5) 0.6610 (4) 0.4106 (3) 0.0297 (10)
H9 1.019059 0.637777 0.366753 0.036*
C10 0.8806 (5) 0.7781 (4) 0.4289 (3) 0.0274 (9)
C11 0.9639 (6) 0.8710 (5) 0.3812 (4) 0.0438 (14)
H11A 0.930569 0.901075 0.324137 0.066*
H11B 1.070837 0.837913 0.367379 0.066*
H11C 0.944671 0.934801 0.421003 0.066*
C12 0.7496 (5) 0.8066 (4) 0.4942 (3) 0.0229 (8)
H12 0.713937 0.886049 0.506986 0.028*
C13 0.8713 (4) 0.5463 (3) 0.8985 (3) 0.0187 (7)
H13 0.959595 0.538994 0.852059 0.022*
C14 0.8560 (5) 0.4544 (3) 0.9656 (3) 0.0193 (7)
C15 0.9699 (5) 0.3434 (4) 0.9583 (3) 0.0253 (9)
H15A 0.954763 0.298232 0.912087 0.038*
H15B 0.959838 0.297465 1.017689 0.038*
H15C 1.069893 0.361719 0.940420 0.038*
C16 0.7285 (5) 0.4683 (4) 1.0339 (3) 0.0228 (8)
H16 0.715074 0.408295 1.081824 0.027*
C17 0.6204 (5) 0.5688 (3) 1.0332 (3) 0.0203 (7)
H17 0.533050 0.578544 1.080271 0.024*
C18 0.6418 (4) 0.6554 (3) 0.9622 (3) 0.0169 (7)
C19 0.5329 (4) 0.7638 (3) 0.9531 (3) 0.0164 (7)
C20 0.3960 (5) 0.7873 (4) 1.0133 (3) 0.0234 (8)
H20 0.370097 0.732986 1.063578 0.028*
C21 0.2976 (5) 0.8908 (4) 0.9992 (3) 0.0235 (8)
H21 0.202621 0.906772 1.039174 0.028*
C22 0.3374 (5) 0.9714 (4) 0.9268 (3) 0.0227 (8)
C23 0.2345 (5) 1.0840 (4) 0.9088 (3) 0.0315 (10)
H23A 0.133003 1.079571 0.942045 0.047*
H23B 0.236537 1.098086 0.842989 0.047*
H23C 0.266645 1.148048 0.929531 0.047*
C24 0.4779 (4) 0.9428 (3) 0.8710 (3) 0.0199 (7)
H24 0.508390 0.998041 0.822531 0.024*
Br1 0.73677 (5) 0.40622 (3) 0.77872 (3) 0.02126 (9)
O8a 0.6439 (14) 1.1597 (9) 0.7718 (7) 0.071 (3)
H8Aa 0.663878 1.128466 0.719848 0.106*
H8Ba 0.669734 1.227376 0.757639 0.106*
  1. aOccupancy: 0.5.


Corresponding author: Lehlohonolo Moherane, Department of Chemistry, Tshwane University of Technology, 0001 Pretoria, South Africa, E-mail:

Funding source: National Research Foundation 10.13039/501100001321

Award Identifier / Grant number: 113629

Funding source: Tshwane University of Technology 10.13039/501100007782

Funding source: University of the Free State

Acknowledgements

The authors would like to acknowledge Tshwane University of Technology (TUT) and the University of the Free State (UFS) for Institutional support.

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

  2. Research funding: AEM received financial assistance from the National Research Foundation (NRF) Thuthuka grant specific number 113629. OTA was supported by the South African National Research Foundation (NRF) and the Research Fund of the University of the Free State.

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

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Received: 2021-05-26
Accepted: 2021-06-14
Published Online: 2021-06-30
Published in Print: 2021-09-27

© 2021 Lehlohonolo Moherane et al., 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 [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
Heruntergeladen am 26.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0210/html
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