Startseite Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
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Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br

  • Zhiqiang Zhen EMAIL logo
Veröffentlicht/Copyright: 9. Dezember 2017

Abstract

C23H22N13Br, triclinic, P1̅ (no. 2), a = 9.255(6) Å, b = 9.819(6) Å, c = 14.497(9) Å, α = 105.186(7)°, β = 90.030(7)°, γ = 102.228(7)°, V = 1240.3(13) Å3, Z = 2, Rgt(F) = 0.0434, wRref(F2) = 0.1116, T = 296(2) K.

CCDC no.: 1587469

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Block, colorless
Size:0.39 × 0.290 × 0.25 mm
Wavelength:Mo radiation (0.71073 Å)
μ:1.70 mm−1
Diffractometer, scan mode:CCD area detector, φ and ω-scans
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:9517, 4573, 0.029
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3195
N(param)refined:336
Programs:Bruker programs [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
Br10.47395(4)0.68049(4)0.21109(3)0.06059(17)
N1−0.2932(3)0.0298(3)0.0604(2)0.0517(8)
N2−0.1704(3)−0.2133(3)0.0437(2)0.0496(7)
N30.1201(3)−0.1724(3)0.12495(19)0.0410(7)
N40.2548(3)−0.1032(3)0.16850(18)0.0392(6)
H40.3240−0.14540.17730.047*
N50.1412(3)0.0703(3)0.17074(19)0.0397(6)
N60.5105(3)0.0884(3)0.26530(18)0.0378(6)
N70.7481(3)−0.0255(3)0.30755(19)0.0414(7)
H70.6738−0.09100.27780.050*
N80.8762(3)−0.0523(3)0.3361(2)0.0419(7)
N90.8822(3)0.1882(3)0.37685(19)0.0414(7)
N101.1749(3)0.0078(3)0.4161(2)0.0526(8)
N111.3006(4)0.2918(4)0.5201(3)0.0671(10)
N120.8398(3)0.4689(3)0.1154(2)0.0529(8)
N131.0036(3)0.5720(3)0.2308(2)0.0482(7)
C1−0.3065(4)−0.2217(4)0.0081(3)0.0602(11)
H1−0.3631−0.3121−0.02380.072*
C2−0.3662(4)−0.1023(4)0.0167(3)0.0570(10)
H2−0.4617−0.1153−0.00930.068*
C3−0.1573(4)0.0394(4)0.0961(2)0.0452(8)
H3−0.10140.13030.12790.054*
C4−0.0954(3)−0.0801(4)0.0880(2)0.0378(8)
C50.0560(3)−0.0618(3)0.1283(2)0.0351(7)
C60.2656(3)0.0399(3)0.1960(2)0.0369(7)
C70.3976(3)0.1443(3)0.2452(2)0.0376(8)
C80.4026(4)0.2913(4)0.2697(3)0.0543(10)
H80.32300.32640.25360.065*
C90.5268(4)0.3836(4)0.3180(3)0.0623(11)
H90.53230.48280.33600.075*
C100.6446(4)0.3295(4)0.3401(3)0.0543(10)
H100.73020.39070.37300.065*
C110.6307(3)0.1805(3)0.3115(2)0.0393(8)
C120.7527(3)0.1163(3)0.3318(2)0.0375(7)
C130.9532(3)0.0802(3)0.3774(2)0.0388(8)
C141.1036(3)0.1141(4)0.4236(2)0.0388(8)
C151.1676(4)0.2540(4)0.4739(3)0.0560(10)
H151.11530.32570.47580.067*
C161.3703(4)0.1851(5)0.5121(3)0.0610(11)
H161.46360.20510.54280.073*
C171.3101(4)0.0470(5)0.4605(3)0.0597(10)
H171.3654−0.02310.45580.072*
C180.6987(5)0.4217(5)0.0584(4)0.0842(15)
H18A0.62950.47610.08980.126*
H18B0.66010.32060.05190.126*
H18C0.71400.4373−0.00390.126*
C190.8664(4)0.5619(4)0.1998(3)0.0549(10)
H190.79960.61280.23260.066*
C201.0667(4)0.4815(4)0.1616(3)0.0528(9)
H201.16290.46810.16430.063*
C210.9651(4)0.4168(4)0.0901(3)0.0528(9)
H210.97640.34920.03370.063*
C221.0777(5)0.6655(4)0.3220(3)0.0679(12)
H22A1.01060.72150.35660.081*
H22B1.16370.73240.30920.081*
C231.1253(5)0.5791(5)0.3822(3)0.0817(14)
H23A1.04140.50840.39130.123*
H23B1.16580.64220.44320.123*
H23C1.19920.53110.35080.123*

Source of material

A mixture of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine (0.05 mmol) and [EMI]Br ionic liquid (EMI = 1-elkyl-3-methylimidazolium) (1 g) in 10 mL mixed solvent (CH3CN/H2O, V/V, 7:3) was placed in a 25 mL Teflon-lined stainless steel vessel, and the vessel was sealed and heated to 160 °C for 72 h. After the mixture had been cooled to room temperature, colorless crystals of the title complex were obtained.

Experimental details

The hydrogen atoms were placed in calculated positions riding on attached atoms with isotropic thermal parameters 1.2 times as those of their carrier atoms. The Uiso values of the hydrogen atoms of methyl group was set to 1.5Ueq.

Discussion

Metal-organic frameworks (MOFs) have attracted lots of interest because their diverse compositions and framework architectures allow for a high degree of control over their properties [4]. Ionothermal synthesis, a method that uses an ionic liquid as solvent and structure directing agents in the preparation of crystalline solids, offers many advantages over traditional hydrothermal and solvothermal synthesis methods [5], [6], [7], [8], [9], [10]. Syntheses using ILs as solvents have received increasing interest for the preparation of functional materials in the context of crystal engineering. In the past years, the synthetic success using the ionothermal method has opened up a new route for the creation of novel inorganic and metal–organic framework materials.

The asymmetric unit contains one neutral 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine, one [EMI]+ cation (EMI = 1-elkyl-3-methylimidazolium) and one Br anion (cf. the figure). The H2ptptp molecule, the [EMI]+ cation, and the Br anion are connected by N—H⋯Br, weak C—H⋯Br, and very weak C—H⋯N hydrogen bonds as well as weak π⋯π stacking interactions to generate a 3D supramolecular framework.

Acknowledgements

This work was supported financially by Henan University of Science and Technology.

References

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Received: 2017-8-18
Accepted: 2017-11-24
Published Online: 2017-12-9
Published in Print: 2018-1-26

©2018 Zhiqiang Zhen, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial 2018
  3. Crystal structure of dimethanol-bis{3-(((2-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N:O′}dizinc(II), C42H30Zn2N2O10
  4. Crystal structure of aqua-bis{[2,6-dimethyl-N-(pyridin-2-ylmethylene)aniline-κ2N,N′]}zinc(II) triflate monohydrate [ZnC29H31N4O]CF3SO3⋅H2O
  5. Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3
  6. Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2
  7. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4,4′-sulfonyldibenzoato-κ2O:O′)zinc(II)], C40H34N4O6SZn
  8. Crystal structure of catena-poly[diaqua(μ3-pyrazine-2,3-dicarboxylato-κ4O,N:O′:O′′)zinc(II)] 1.25 hydrate, C6H8.5N2O7.25Zn
  9. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri-m-tolyl phosphane-κP)rhenium(I), C29H28O5PRe
  10. Crystal structure of bis(μ2-methanolato-κ2O:O)-bis(methanol-κ1O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,O′,N}dichromium(III), C38H36Cr2N2O14
  11. Crystal structure of poly[aqua-(μ3-pyridine-3,5-dicarboxylato-κ5O,O′:O′′,O′′′,N)zinc(II)], C7H7NO6Zn
  12. Crystal structure of bis((1-(((4-(((benzyloxy)imino)methyl)phenyl)imino)methyl)naphthalen-2-yl)oxy-κ2O,N)copper(II), C52H42CuN4O4
  13. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}cobalt(II), C40H38CoN4O6
  14. Crystal structure of diaqua-bis(N,N-dimethylformamide-κ1O)-bis{3-((5-chloro-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ4N,O,O′:O′}dinickel(II), C38H34Ni2Cl2N4O12
  15. Crystal structure of tetrakis(methanol-κO)bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}bicobalt(II), C38H38Co2N2O14
  16. Crystal structure of (S)-tert-butyl-(1-hydroxypropan-2-yl)carbamate, C8H17NO3
  17. Crystal structure of 4-(4′-(pyridin-4-yl)-[1,1′-biphenyl]-4-yl)pyridin-1-ium catena-poly[{5-carboxy-4′-methyl-[1,1′-biphenyl]-3-carboxylato-κ2O,O′}-(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-κ4O,O′:O′′,O′′′)lead(II)], C52H40N2O9Pb
  18. Crystal structure of catena-poly[diaqua-(μ2-5-methylisophthalato-κ2O:O′)(μ2-1,4-bis((1H-1,2,4-triazol-1-yl)methyl)benzene-κ2N:N′)], NiC21H22O6N6
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  26. Crystal structure of pyrimidine-2,5-dicarboxylic acid 1.5 hydrate, C12H14N4O11
  27. Crystal structure of trans-diaqua-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II), C8H10N4O6Mn
  28. Crystal structure of catena-(μ3-5-bromoisophthatato-κO,O′: O′′,O′′′′)-(1,2-bis(imidazol-1-yl)ethane-κN:N′)cobalt(II), C16H13CoN4O4Br
  29. Investigation of the compound La5Zn2−xPb1 + x (x = 0.20–0.32)
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  38. Crystal structure of poly[aqua-(μ5-2,5-dicarboxybenzoato-κ5O:O:O′:O′′:O′′′)sodium(I)], C9H7NaO7
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  48. Crystal structure of 4-chloro-2-methyl-6-(4-(trifluoromethoxy)phenyl)pyrimidine, C12H8ClF3N2O
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  52. The crystal structure of (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid, C16H15N3O2S
  53. Crystal structure of 2-chloro-1,3-di-tert-pentyl-4,4-diphenyl-1,3,2λ3,4-diazaphosphasiletidine, C22H32ClN2PSi
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  55. Crystal structural of 2-amino-4-(4-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C19H20N2O3
  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
  57. The crystal structure of bis(2-benzoyl-5-hydroxylphenolato-κ2O,O′)copper(II), C26H18CuO6
  58. Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
  59. The crystal structure of (E)-N-benzyl-N′-benzylidene-4-methylbenzenesulfonohydrazide, C21H20N2O2S
  60. Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6
  61. The crystal structure of (E)-4-(3-ethoxy-2-hydroxybenzylideneamino)benzoic acid, C16H15NO4
  62. Crystal structure of (μ2-N,N′-bis((pyridin-4-yl)methyl)ethanediamide-κ2N:N′)-tetrakis(diethylcarbamodithioato-κ2S,S′)dizinc(II), C34H54N8O2S8Zn2
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