Startseite The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
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The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)

  • Hou Haibin ORCID logo , Jin Guoliang , Su Hongping , Chen Lizhen ORCID logo EMAIL logo und Wang Jianlong
Veröffentlicht/Copyright: 7. August 2024

Abstract

C15H24KN5O2, orthorhombic, Pbcn (no. 60), a = 14.0281(6) Å, b = 13.4110(6) Å, c = 12.2842(5) Å, V = 2311.04(17) Å3, Z = 4, R gt (F) = 0.0358, wR ref (F2) = 0.0994, T = 150 K.

CCDC no.: 2372862

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: 0.13 × 0.12 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.30 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 24.7°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 24,603, 1979, 0.073
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 1492
N(param)refined: 152
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4
Table 2:

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

Atom x y z Uiso*/Ueq
K1 0.000000 0.500000 0.000000 0.0503 (2)
O1 0.15021 (9) 0.37487 (10) 0.06865 (11) 0.0653 (4)
O2 0.18273 (9) 0.58163 (11) 0.02762 (12) 0.0660 (4)
O3 0.04107 (10) 0.68740 (10) −0.08280 (12) 0.0633 (4)
O4 0.08231 (11) 0.43527 (10) −0.18959 (14) 0.0749 (4)
O5 0.19952 (10) 0.33693 (12) −0.22359 (14) 0.0784 (5)
O6 −0.07422 (18) −0.02132 (13) −0.2686 (2) 0.1234 (9)
N1 0.11457 (11) 0.35398 (12) −0.21588 (13) 0.0547 (4)
N2 0.07970 (11) 0.17989 (11) −0.22902 (14) 0.0580 (4)
N3 0.000000 0.0214 (2) −0.250000 0.0852 (9)
C1 0.22796 (15) 0.43093 (18) 0.1121 (2) 0.0794 (6)
H1A 0.282731 0.386212 0.126231 0.095*
H1B 0.208897 0.462059 0.181869 0.095*
C2 0.25580 (16) 0.50913 (18) 0.0332 (2) 0.0811 (6)
H2A 0.316189 0.540769 0.056580 0.097*
H2B 0.265881 0.479063 −0.039472 0.097*
C3 0.20353 (15) 0.65931 (19) −0.0472 (2) 0.0773 (6)
H3A 0.210172 0.631409 −0.121458 0.093*
H3B 0.264485 0.691681 −0.027230 0.093*
C4 0.12573 (17) 0.73359 (17) −0.0454 (2) 0.0780 (6)
H4A 0.116468 0.758794 0.029627 0.094*
H4B 0.142078 0.790710 −0.092885 0.094*
C5 −0.03823 (17) 0.75398 (16) −0.0916 (2) 0.0772 (6)
H5A −0.020701 0.812109 −0.137057 0.093*
H5B −0.056584 0.778491 −0.018527 0.093*
C6 −0.11876 (17) 0.70011 (19) −0.1416 (2) 0.0799 (6)
H6A −0.170617 0.745416 −0.158310 0.096*
H6B −0.096927 0.669906 −0.208870 0.096*
C7 0.04860 (12) 0.27400 (13) −0.23768 (15) 0.0479 (4)
C8 0.000000 0.1300 (2) −0.250000 0.0604 (7)

1 Source of material

N,N-dimethylformamide was used as the base liquid, and potassium salt of 2,4,5-trinitroimidazole and 18-crown-6 were added to the reactor in a molar ratio of 1:1. The reaction was carried out at 323.15 K for 1 h, and the light yellow solid product was recrystallized in acetone solution to obtain the title product. X-ray single crystal diffraction was performed on the crystal.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Trinitroimidazole compounds are energetic compounds with high potential. 5 2,4,5-Trinitroimidazole is a compound in which the H of the 2,4 and 5 positions of the imidazole ring is substituted by nitro, and its sensitivity is lower than that of hexogen and octogen. Normally, Na+ or K+ is substituted to N of 2,4,5-trinitroimidazole to make it a salt to increase its energy and stability.

The asymmetric unit of the title compound is half a molecule. All bond lengths and angles are within the expected range. As shown in the figure, the title compound is a 1:1 complex of 18-crown-6 with K+ and trinitroimidazole. K+ and 18-crown-6 are connected by metal ion coordination bonds. 18-Crown-6 and nitroimidazole form bonds with oxygen atoms in the upper nitro group of imidazole positions 4 and 5 through K+. The dihedral angle between the plane of C15, C14, N2, N3 and O11 atoms in nitroimidazole and the plane of K1, O1 and O3 in crown ether is 24.27°.

General symmetric crown ethers have high ability to bond cations. 6 , 7 , 8 , 9 When the metal ion is matched to the crown ether size, it gives a strong ion-dipole interaction and shows a strong ionic bond and ability. In the 18-crown-6 coordination of K+, the size matching gives a strong ionic dipole interaction. 10


Corresponding author: Chen Lizhen, School of Chemistry and Chemical Engineering, North University of China, Taiyuan 030051, Shanxi Province, P.R. China, E-mail:

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

  2. Research funding: Shanxi Province Postgraduate Education Innovation Project [2023KY605].

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

References

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Received: 2024-03-03
Accepted: 2024-07-23
Published Online: 2024-08-07
Published in Print: 2024-10-28

© 2024 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. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O:O)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
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  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
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  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
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  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
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  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
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  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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