Startseite The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
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The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate

  • Yunlu Li ORCID logo EMAIL logo , Rui Zhou , Bo Wang und Shengping Fan
Veröffentlicht/Copyright: 23. Oktober 2024

Abstract

C5H7Cl3N4O3, monoclinic, P21/c (no. 14), a = 5.745(3) Å, b = 29.120(13) Å, c = 6.813(3) Å, β = 107.649(6)°, V = 1086.1(9) Å3, Z = 4, R gt (F) = 0.0411, wR ref (F 2) = 0.1163, T = 296 K.

CCDC no.: 2389954

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: 0.20 × 0.20 × 0.20 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.84 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.6°, >99 %
N(hkl)measured, N(hkl)unique, R int: 6479, 2502, 0.023
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2,118
N(param)refined: 167
Programs: Olex2 1 , SHELX 2 , 3 , Bruker 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.7127 (5) 0.69011 (8) 0.2759 (4) 0.0431 (6)
H1 0.713916 0.720247 0.230982 0.052*
N1 0.8127 (4) 0.65474 (7) 0.2121 (3) 0.0401 (4)
H1A 0.889877 0.655881 0.122033 0.048*
Cl1 0.71267 (14) 0.55584 (2) 0.70060 (10) 0.0547 (2)
C2 0.7749 (4) 0.61569 (7) 0.3115 (3) 0.0320 (4)
O2 0.3570 (4) 0.60339 (6) 0.8231 (3) 0.0483 (4)
H2 0.254784 0.618127 0.858413 0.072*
N2 0.6108 (4) 0.67580 (6) 0.4138 (3) 0.0367 (4)
H2A 0.532247 0.692765 0.475578 0.044*
C5 0.8502 (4) 0.57083 (8) 0.2584 (3) 0.0387 (5)
Cl2a 1.12042 (19) 0.56408 (4) 0.2188 (2) 0.0477 (4)
N3a 0.6892 (15) 0.5369 (2) 0.2383 (18) 0.0354 (15)
O1a 0.7811 (4) 0.49535 (8) 0.1912 (4) 0.0505 (7)
H1Ba 0.683178 0.474733 0.189115 0.076*
Cl2Ab 0.7215 (16) 0.5264 (2) 0.2397 (19) 0.0389 (16)
N3Ab 1.086 (2) 0.5794 (4) 0.231 (2) 0.042 (2)
O1Ab 1.1701 (14) 0.5372 (3) 0.1728 (13) 0.0438 (18)
H1AAb 1.317674 0.538749 0.190988 0.066*
C3 0.5725 (4) 0.60623 (7) 0.6026 (3) 0.0317 (4)
Cl3 1.04629 (13) 0.68544 (2) −0.11491 (10) 0.0495 (2)
O3 1.3573 (4) 0.77021 (6) 0.1020 (3) 0.0570 (5)
H3A 1.278113 0.786170 0.177639 0.085*
H3B 1.244903 0.747670 0.059739 0.085*
N4 0.4138 (4) 0.62623 (6) 0.6663 (3) 0.0365 (4)
C4 0.6498 (4) 0.62945 (7) 0.4433 (3) 0.0302 (4)
  1. aOccupancy: 0.772(4), bOccupancy: 0.228(4).

1 Source of material

Add 0.01 mol 4,5-dicyanoimidazole and 0.04 mol hydroxylamine aqueous solution to the reactor. The temperature of the reactor was maintained at 298.15 K and the reaction is for 2 h. After the reaction is completed, the reaction solution is filtered. Remove the filtrate and retain the precipitate. Add 0.01 mol above solid and 20 mL NaNO2 to the reactor. The temperature of the reactor was maintained at 273 K. 10 mL 37 % hydrochloric acid is slowly added dropwise into the reaction for 2 h. After the reaction is completed, the reaction solution is filtered. Remove the filtrate and retain the white solid. The white solid is dissolved in methanol and is volatilized at room temperature to obtain clear colourless block crystals.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms. All the non-hydrogen atoms were refined anisotropically.

3 Comment

Imidazole compounds and their energetic salts are research hotspots in the field of energetic materials in various countries. 5 , 6 , 7 , 8 4,5-Dicyanoimidazole is an important imidazole compound that has been extensively studied. 9 , 10 The title compound was obtained by reacting 4,5-dicyanoimidazole, hydroxylamine aqueous solution and 37 % hydrochloric acid. The title compound is an organic compound with high research value in the preparation of imidazole energetic salts.

The bond lengths and angles in the title molecule are in the expected ranges. 11 The four atoms Cl2, C5, N3, O1 are in the same plane and the four atoms Cl1, C3, N4, O2 are also in the same plane. The dihedral angle formed by imidazole ring and place of Cl2, C5, N3, O1 is 41.514° and the dihedral angle formed by imidazole ring and place of Cl1, C3, N4, O2 is 21.1°.

The title compound was obtained by reacting 4,5-dicyanoimidazole, hydroxylamine aqueous solution and 37 % hydrochloric acid. During the reaction, hydroxylamine molecules are free in solution in the form –NH2 and –OH and hydrochloric acid is free in solution in the form –Cl. The –CN triple bond of 4,5-dicyanoimidazole becomes double bond, with the C atom connected to –Cl and the N atom connected to –OH, generating the (4Z,5E)-N′4,N′5-dihydroxy-1H-imidazole-4,5-bis(carbimidoyl) dichloride molecule. Due to the presence of a large amount of hydrochloric acid in the solution, the title salt was obtained.


Corresponding author: Yunlu Li, School of Environment and Safety Engineering, North University of China, Taiyuan 030051, Shanxi Province, 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: This work was supported by National Science Foundation of China under grant 22105023.

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

References

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Received: 2024-07-25
Accepted: 2024-10-10
Published Online: 2024-10-23
Published in Print: 2024-12-17

© 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. New Crystal Structures
  3. Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
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