Startseite Naturwissenschaften The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
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The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2

  • Wang Li-Hua , Song Gui-Quan EMAIL logo und Tai Xi-Shi ORCID logo
Veröffentlicht/Copyright: 7. August 2024

Abstract

C6H6N2O2, monoclinic, P21/n (no. 14), a = 3.6915(7) Å, b = 19.265(5) Å, c = 8.1468(16) Å, β = 92.47(2)°, V = 578.8(2) Å3, Z = 4, R gt (F) = 0.0468, wRref(F2) = 0.1254, T = 150 K.

CCDC no.: 2374485

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 × 0.10 × 0.09 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.12 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 2,332, 1,029, 0.029
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 812
N(param)refined: 96
Programs: Bruker 1 , Olex2 2 , SHELX 3 , Diamond 4
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.6359 (4) 0.37360 (8) 0.18401 (17) 0.0235 (5)
O2 0.8879 (4) 0.46496 (8) 0.31544 (18) 0.0230 (5)
N1 0.7210 (5) 0.41604 (10) 0.6065 (2) 0.0176 (5)
H1 0.824622 0.455386 0.591715 0.021*
N2 0.7589 (6) 0.43811 (12) 0.8855 (2) 0.0242 (5)
H2A 0.719513 0.419137 0.973062 0.036*
H2B 0.873 (8) 0.4757 (17) 0.862 (3) 0.034 (8)*
C1 0.6574 (6) 0.39650 (12) 0.7625 (2) 0.0171 (5)
C2 0.4895 (6) 0.33131 (12) 0.7843 (3) 0.0189 (5)
H2 0.439678 0.316053 0.889281 0.023*
C3 0.4009 (6) 0.29098 (12) 0.6514 (3) 0.0200 (6)
H3 0.294237 0.247814 0.666003 0.024*
C4 0.4700 (6) 0.31432 (12) 0.4913 (3) 0.0189 (6)
H4 0.406433 0.287063 0.400340 0.023*
C5 0.6298 (6) 0.37676 (12) 0.4720 (3) 0.0162 (5)
C6 0.7255 (6) 0.40764 (12) 0.3083 (3) 0.0180 (5)

1 Source of materials

6-Amino-pyridinium-2-carboxylate was obtained as the following: 0.1381 g 6-aminopyridine-2-carboxylic acid (0.1 mmol), 0.1572 g 2-quinolinecarboxaldehyde (1.0 mmol), 0.2165 g lanthanum(III) nitrate hexahydrate (0.50 mmol), and 0.040 g NaOH (1.0 mmol) were together added to the solution of 15 mL ethanol-water (v:v = 2:1) with stirring. Then the mixture was stirred for 3 h at 75 °C and then cooled to room temperature. The colourless block crystals of the title compound were received in 6 days.

2 Experimental details

The hydrogen atoms were positioned geometrically (C–H = 0.93 Å, N–H = 0.82–0.86 Å). Their Uiso values were set to 1.2Ueq or 1.5Ueq of the parent atoms.

3 Comment

The study of rare earth metal complexes has always been one of the research fields of coordination chemistry for their excellent potential applications in catalysis, 5 , 6 fluorescent probe, 7 antitumor activity. 8 We have synthesized and structural characterized some rare earth metal complexes. 9 , 10 , 11 To further enrich the structure of the rare earth complex, we proposed to synthesize a new complex from 6-aminopyridine-2-carboxylic acid, 2-quinolinecarboxaldehyde and lanthanum(III) nitrate hexahydrate. However, unlike our expected results, 6-aminopyridine-2-carboxylic acid and 2-quinolinecarboxaldehyde did not react to form the Schiff base ligand, and the lanthanum(III) ion were not involved in coordination. Only a single crystal of 6-amino-pyridinium-2-carboxylate was obtained. The molecular structure of 6-amino-pyridinium-2-carboxylate is shown in Figure. Single-crystal structural analysis shows that the 6-amino-pyridinium-2-carboxylate crystallizes in the monoclinic system with the P21/n (no. 14) space group. The bond lengths of C–O and C–N are in the range of 1.239(3) Å–1.257(3) Å and 1.325(3) Å–1.362(3) Å, 12 respectively. In the crystal structure, it forms a 1D chained structure via strong intermolecular N–H⋯O hydrogen bonds. The 1D chains further form a two-dimensional layered structure via π stacking interactions of pyridinium rings.


Corresponding author: Song Gui-Quan, College of Biology and Oceanography, Weifang University, Weifang, Shandong 261061, 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. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  3. Research funding: National Natural Science Foundation of China (No. 21171132, https://doi.org/10.13039/501100001809), the Natural Science Foundation of Shandong (ZR2014BL003, https://doi.org/10.13039/501100007129), the Project of Shandong Province Higher Educational Science and Technology Program (J14LC01, https://doi.org/10.13039/501100015642) and Science Foundation of Weifang (2020ZJ1054).

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Received: 2024-07-02
Accepted: 2024-07-30
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
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  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
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  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
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
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  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
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  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
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  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
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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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