Startseite The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
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The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3

  • Dan-Xia Li EMAIL logo , Hai-Jun Wang , Zhen-Li Yan und Chao-Jun Du ORCID logo
Veröffentlicht/Copyright: 4. Januar 2022

Abstract

C6H9I5N2O3, triclinic, P1¯ (no. 2), a = 7.4851(5) Å, b = 9.6056(6) Å, c = 12.4084(7) Å, α = 109.119(3)°, β = 99.341(3)°, γ = 92.334(3)°, V = 827.53(9) Å3, Z = 2, R gt (F) = 0.0234, wR ref (F2) = 0.0449, T = 150.0 K.

CCDC no.: 2127394

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: Red block
Size: 0.20 × 0.15 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 9.39 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint: 17,263, 3386, 0.045
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2864
N(param)refined: 149
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
C1 0.9540 (6) 0.2526 (5) 0.6136 (4) 0.0204 (10)
C2 0.8744 (6) 0.2678 (5) 0.5012 (4) 0.0209 (10)
C3 0.8110 (6) 0.3904 (5) 0.4862 (4) 0.0257 (11)
H3 0.816407 0.478628 0.550662 0.031*
C4 0.7357 (6) 0.3856 (6) 0.3719 (4) 0.0279 (11)
H4 0.687965 0.470450 0.359699 0.033*
C5 0.7322 (6) 0.2592 (6) 0.2800 (4) 0.0269 (11)
H5 0.682366 0.256349 0.203720 0.032*
C6 0.8028 (6) 0.1314 (5) 0.2977 (4) 0.0208 (10)
I1 0.62729 (5) 0.31666 (4) 0.96864 (3) 0.02959 (9)
I2 0.48900 (4) 0.25468 (3) 0.69938 (2) 0.02325 (8)
I3 0.36535 (4) 0.18894 (4) 0.46452 (3) 0.03150 (9)
I4 0.80776 (5) −0.30113 (4) 0.81772 (3) 0.03111 (9)
I5 0.72338 (4) −0.00810 (3) 0.89310 (2) 0.02435 (8)
N1 0.8668 (5) 0.1409 (4) 0.4078 (3) 0.0189 (8)
H1 0.905890 0.061554 0.420587 0.023*
N2 0.8079 (5) 0.0076 (4) 0.2119 (3) 0.0277 (9)
H2A 0.853126 −0.068723 0.226765 0.033*
H2B 0.765963 0.001213 0.139807 0.033*
O1 0.9811 (5) 0.3782 (3) 0.7009 (3) 0.0275 (8)
H1A 1.020862 0.362390 0.762739 0.041*
O2 0.9927 (4) 0.1336 (3) 0.6218 (2) 0.0223 (7)
O1W 0.0920 (6) 0.3149 (4) 0.8878 (3) 0.0399 (9)
H1WA 0.199111 0.349720 0.930224 0.060*
H1WB 0.017030 0.342507 0.935769 0.060*

Source of material

An amount of 1.38 g of 6-aminopyridine-2-carboxylic acid (10 mmol) was dissolved in 10 mL 45% hydroiodic acid, then filtered. Many red crystals were harvested after about 10 days, yield 74% (based on 6-aminopyridine-2-carboxylic acid).

Experimentaldetails

The structure was solved by direct methods with the SHELXS program. All H-atoms from C and N atoms were positioned with idealized geometry (Uiso(H) = 1.2Ueq(C) and (N)) using a riding model with C–H = 0.95 Å and N–H = 0.88 Å. The H-atoms for O and O1W were refined with the distance of O1–H1A = 0.84, O1–H1WA = O1–H1WB = 0.87 Å with Uiso(H) = 1.5Ueq(O), respectively.

Comment

Many pyridinium-based polyiodides have been reported, for example, 2-amino-pyridin-1-ium triiodide [56] and bis((4-aminopyridin-1-ium) iodide triiodide. But only a few pyridinium-based pentaiodides have been published, such as aminopyridinium pentaiodide [7], isoquinolinium pentaiodide [8], nevirapinium pentaiodide [9], N-(6-methyl-2-pyridyl)mesitylenesulfonamide pentaiodide [10], and 3-[5-(pyridin-3-yl)-1,2,4-thiadiazol-3-yl]pyridinium pentaiodide [11].

The title compound, with the formula of C6H9I5N2O3, crystalizes in triclinic, P-1 (no. 2). The asymmetric unit is made of one 6-amino-5-carboxypyridin-1-ium cation, one pentaiodide anion and one water molecule. In the 6-amino-5-carboxypyridin-1-ium cation, the N atom from of the pyridine ring is protonated and both the amino and carboxyl groups are neutral. The distances of I4–I5 and I2–I3 are 2.794 and 2.760 Å, respectively, rather shorter than the distances of I1–I5 (3.101 Å) and I1–I2 (3.181 Å). The structure features an organic moiety consisting of two water molecules and two cations to form the dimers, which are generated by the hydrogen bonds N1–H1⋯O2, N2–H2A⋯O2, and O1–H1A⋯O1W. The anions and the cations are connected by van der Waals interactions to form layers in the bc plane.


Corresponding author: Dan-Xia Li, Zhang Zhongjing College of Chinese Medicine, Nanyang Institute of Technology, Nanyang, Henan, 473000, P. R. China, E-mail:

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

  2. Research funding: None declared.

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

References

1. Bruker. SAINT v8.37A; Bruker AXS Inc: Madison, Wisconsin, USA, 2015.Suche in Google Scholar

2. Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K., Puschmann, H. The anatomy of a comprehensive constrained, restrained refinement program for the modern computing environment-Olex2 dissected. Acta Crystallogr. 2015, A71, 59–75; https://doi.org/10.1107/s2053273314022207.Suche in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Sheldrick, G. Using phases to determine the space group. Acta Crystallogr. 2018, A74, a353; https://doi.org/10.1107/s0108767318096472.Suche in Google Scholar

5. Reiss, G. J., Leske, P. B. 2-Amino-pyridin-1-ium triiodide. Acta Crystallogr. 2013, E69, o1060–o1061; https://doi.org/10.1107/s1600536813015389.Suche in Google Scholar

6. Reiss, G. J., Leske, P. B. The twinned crystal structure of bis(4-aminopyridin-1-ium) iodide triiodide, C20H28I8N8. Z. Kristallogr. N. Cryst. Struct. 2014, 229, 452–454; https://doi.org/10.1515/ncrs-2014-0193.Suche in Google Scholar

7. Buikin, P. A., Ilyukhin, A. B., Baranchikov, A. E., Yorov, K. E., Kotov, V. Y. The relationship between the crystal structure and optical properties for isomeric aminopyridinium iodobismuthates. Mendeleev Commun. 2018, 28, 490–492; https://doi.org/10.1016/j.mencom.2018.09.012.Suche in Google Scholar

8. Wu, Y., Shao, M., Feng, Z., Gu, X., Hong, Y., Cui, Q., Ren, L., Wang, S. Synthesis of iodine-substituted quinolines, quinolinium salts, and isoquinolinium salts via a three-component tandem reaction of aryl azides, propargylic alcohols, and iodine. Asian J. Org. Chem. 2017, 66, 76–82; https://doi.org/10.1002/ajoc.201600503.Suche in Google Scholar

9. Kryukova, M. A., Sapegin, A. V., Novikov, A. S., Krasavin, M., Ivanov, D. M. Non-covalent interactions observed in nevirapinium pentaiodide hydrate which include the rare I4–I−⋯O=C halogen bonding. Z. Kristallogr. Cryst. Mater. 2019, 234, 101–108; https://doi.org/10.1515/zkri-2018-2081.Suche in Google Scholar

10. Pan, F., Englert, U. N-(6-methyl-2-pyridyl)mesitylenesulfonamide: an efficient template for polyiodides. Cryst. Growth Des. 2014, 14, 1057–1066; https://doi.org/10.1021/cg4015477.Suche in Google Scholar

11. Aragoni, M. C., Arca, M., Caltagirone, C., Castellano, C., Demartin, F., Garau, A., Isaia, F., Lippolis, V., Montis, R., Pintus, A. Cationic and anionic 1D chains based on NH+⋯N charge-assisted hydrogen bonds in bipyridyl derivatives and polyiodides. CrystEngComm 2012, 14, 5809–5823; https://doi.org/10.1039/c2ce25212k.Suche in Google Scholar

Received: 2021-10-27
Accepted: 2021-12-09
Published Online: 2022-01-04
Published in Print: 2022-02-23

© 2021 Dan-Xia Li 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 (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4] anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a 2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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