Startseite The crystal structure of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate, C6H9ClN2O7
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The crystal structure of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate, C6H9ClN2O7

  • Siyu Hou ORCID logo EMAIL logo , Penggang Ren und Yan Zeng
Veröffentlicht/Copyright: 31. März 2021

Abstract

C6H9ClN2O7, triclinic, P1 (no. 2), a = 6.8667(4) Å, b = 7.5196(4) Å, c = 10.0908(5) Å, α = 74.237(2), β = 81.603(3), γ = 88.888(3), V = 495.95(5) Å3, Z = 2, Rgt(F) = 0.0377, wRref(F2) = 0.0902, T = 150(2) K.

CCDC no.: 2065267

The asymmetric unit of the title crystal 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:Colorless block
Size:0.20 × 0.15 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.41 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:12,649, 2054, 0.072
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1609
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).

AtomxyzUiso*/Ueq
C10.1938 (3)−0.2739 (3)0.6848 (2)0.0201 (5)
C20.2139 (3)−0.0704 (3)0.6168 (2)0.0171 (5)
C30.2667 (3)−0.0091 (3)0.4740 (2)0.0181 (5)
H30.286515−0.0963050.4207720.022*
C40.2912 (3)0.1804 (3)0.4068 (2)0.0195 (5)
C50.2590 (3)0.3016 (3)0.4909 (2)0.0206 (5)
H50.2726910.4311740.4500830.025*
C60.1855 (3)0.0557 (3)0.6956 (2)0.0200 (5)
H60.1506780.0157370.7938920.024*
Cl10.68697 (8)0.21373 (7)0.87046 (6)0.01990 (16)
N10.2089 (3)0.2353 (2)0.62844 (19)0.0213 (4)
H10.1900000.3153500.6782800.026*
N20.3484 (3)0.2445 (3)0.2676 (2)0.0301 (5)
H2A0.3658500.3640630.2289150.036*
H2B0.3681850.1666980.2160150.036*
O10.2351 (3)−0.3857 (2)0.61864 (17)0.0323 (4)
O20.1300 (3)−0.3156 (2)0.81855 (16)0.0258 (4)
H20.137636−0.4300110.8530990.039*
O30.5590 (3)0.1041 (2)0.82217 (19)0.0332 (4)
O40.7986 (3)0.3422 (3)0.7533 (2)0.0443 (5)
O50.5694 (3)0.3152 (3)0.9539 (2)0.0366 (5)
O60.8201 (2)0.0957 (2)0.95093 (17)0.0243 (4)
O1W0.1691 (2)0.3292 (2)0.90705 (17)0.0237 (4)
H1WA0.2760460.3006890.9442130.036*
H1WB0.0831470.2446870.9564930.036*

Source of material

5-Aminopyridine-3-carboxylic acid (0.138 g, 1 mmol) was added to a solution of 10 mL concentrated perchloric acid (70%) under room temperature and stirred for 15 min. The mixture was filtered and left to evaporate naturally. A few days later, colorless block crystals of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate were harvested, yield 78% (based on 5-aminopyridine-3-carboxylic acid [APCA]).

Experimental details

The structure was solved by direct methods with the SHELXS program. All H-atoms from C atoms and N atoms were positioned with idealized geometry and refined isotropically (Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.2Ueq(C)) using a riding model with C–H = 0.95 Åand N–H = 0.879 and 0.88 Å). The H2, H1WA and H1WB were positioned based on difference electron density peaks and refined with the distance restraints of O2–H2 = 0.84 Å, O1W–H1WA = 0.87 Åand O1W–H1WB = 0.87 Å, respectively (Uiso(H) = 1.5Ueq(O)).

Comment

5-Aminopyridine-3-carboxylic acid and its deprotonated derivatived anions are known as multi-functional ligands to build various metal (Co(II), Zn(II), Cu(II), Cd(II), Pb(II) and Y(III)) complexes [5], [6], [7], [8], [9], [10] and heterometallic complexes (Cu(II)–Ti(IV) and Cu(II)–In(III)) [11], [12], [13] with excellent applications. However, to date, the single-crystal stucture of 5-aminopyridine-3-carboxylic acid or any of its salts have not been reported.

The title compound crystalises in P1. The asymmetric unit of the title compound consitsts of one N-protonated 5-carboxypyridin-1-ium cation, one perchlorate anion, and one crystal water molecule. All the atoms of the 3-aminopyridine moiety are nearly co-planar, but the free carboxyl group is slightly twisted. All the bond lengths of C–C, C–N and C–O are normal, which are comparable to their analogues [14, 15]. There are two kinds of one-dimensional chains: one is constructed by the hydrogen bond N1–H1⃛O1 and the other is constructed by the hydrogen bonds O1W–H1WA⃛O5 and O1W–H1WB⃛O6. The hydrogen bonds N2–H2A⃛O4 and N2–H2A⃛O4 link the aforementioned chains to generate a three-dimensional supramolecular structure.


Corresponding author: Siyu Hou, School of Mechanical and Electrical Engineering, School of Materials Science and Chemical Engineering, Xi’an Technological University, Xi’an, Shaanxi710021, 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.

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Received: 2021-02-14
Accepted: 2021-02-26
Published Online: 2021-03-31
Published in Print: 2021-07-27

© 2021 Siyu Hou 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 poly[(μ2-aqua-tetraaqua-(μ3-glutarato-κ4O,O′:O′:O′′)-(μ5-glutarato-κ6O:O,O′:O′:O′′:O′′′)distrontium(II)], C10H22O13Sr2
  4. The crystal structure of acetato-κ1O-{(2-(2-(2-aminophenoxy)ethoxy)phenyl)(4-oxo-4-phenylbut-2-en-2-yl)amido-κ2N,N′,O}copper(II), C26H26CuN2O5
  5. Crystal structure of dimethanolato-k2O:O-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)dicopper(II), C34H32Cu2N12O2S2
  6. Crystal structure of poly[diaqua-bis(μ2-3-(pyrimidin-5-yl)benzoato-κ2N:O)cobalt(II)] dihydrate, [Co(C11H11O2N2)2(H2O)2]
  7. Crystal structure of bis(3,3-dimethyl-1-phenylbut-1-en-2-yl)(trimethylsilyl)amido-k1N)zinc(II), Zn(C15H24NSi)2
  8. Crystal structure of catena-poly[(μ2-methanolato-κ2O:O)-(μ2-1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)-(thiocyanato-κ1N)copper(II)] 0.25 hydrate, C17H16CuN6OS ⋅ 0.5H2O
  9. The crystal structure of 2-amino-5-nitroanilinium iodide monohydrate, C6H8IN3O2
  10. The crystal structure of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate, C6H9ClN2O7
  11. Crystal structure of 7-hydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene from Arundina graminifolia, C16H16O3
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  13. The crystal structure of 2-amino-5-carboxypyridin-1-ium iodide monohydrate, C6H9IN2O3
  14. The crystal structure of 2-(3,5-difluorophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H11BF2N2
  15. Crystal structure of bis{(2-pyridinyl)-1-phenyl-1-isopropylmethanolato-κ2N,O}nickel, C30H32N2NiO2
  16. Crystal structure of poly[(m3-3-carboxyadamantane-1-carboxylato-κ3O:O′:O″)-(phenanthroline-κ2N,N′)sodium(II)], C24H23N2NaO4
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  18. Crystal structure of 4-tert-butyl-2-N-(2-pyridylmethyl)aminophenol, C16H20N2O
  19. The crystal structure of (3Z,3′Z)-4,4′-((1,4-phenylenebis(methylene))bis(azanediyl))bis(pent-3-en-2-one), C18H24N2O2
  20. Crystal structure of (morpholine-1-carbodithioato-κ2-S,S′)bis(triphenylphosphine-κ-P)gold(I), C41H38AuNOP2S2
  21. Crystal structure of 1,4-bis(4-bromobenzyl)-4-(4-chlorophenyl)-1,4-dihydropyridine-3-carbonitrile, C26H19Br2ClN2
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  26. Crystal structure of benzo[d][1,3]dioxol-5-yl-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18O5
  27. The crystal structure of ethyl 5-methyl-7-(4-(phenylthio)phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C20H19N5O2S
  28. Crystal structure of N′,N‴-((propane-2,2-diylbis(1H-pyrrole-5,2-diyl))bis(methaneylylidene))-di(isonicotinohydrazide)– water – dimethylformamide (1/4/2), C25H24N8O2·4H2O·2C3H7NO
  29. Synthesis and crystal structure of 4-(2,4-dinitrophenoxy)benzaldehyde, C13H8N2O6
  30. The crystal structure of 1-dodecylpyridin-1-ium bromide monohydrate, C17H32BrNO
  31. Crystal structure of (E)-amino(2-(4-(dimethylamino)benzylidene)hydrazineyl)methaniminium nitrate, C10H16N6O3
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  33. The crystal structure of hexakis(1-propylimidazole-κ1N)copper(II) dichloride, C36H60Cl2CuN12
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  52. Synthesis and crystal structure of (1E,2E)-3-(anthracen-9-yl)-1-(4-methoxyphenyl)prop-2-en-1-one oxime, C24H19NO2
  53. Synthesis and crystal structure of (2E,2′E)-3,3′-(1,3-phenylene)bis(1-(3-bromophenyl)prop-2-en-1-one), C24H16Br2O2
  54. The crystal structure of catena-poly[bis(µ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene- κ2N:N′)-bis(nitrato-κO)copper(II)], C28H28N10O6Cu
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  56. Crystal structure of (E)-3-(dimethylamino)-1-(thiophen-3-yl)prop-2-en-1-one, C9H11NOS
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  58. Crystal structure of cyclopropane-1,2,3-triyltris(phenylmethanone), C24H18O3
  59. Crystal structure of bis(amino(thioureido)methaniminium) terephthalate, C12H18N8O4S2
  60. A three-dimensional Eu(III) framework in the crystal structure of dimethylaminium poly[dimethylformamide-κ1N)bis(μ4-terephthalato-κ4O:O′:O′′:O′′′)europium(III)] monohydrate, C21H25EuN2O10
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