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Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 230 Issue 4

Abstract

C5H9IN2, orthorhombic, P212121 (no. 19), a = 6.8704(2) Å, b = 8.6118(3) Å, c = 13.5373(5) Å, V = 801.0 Å3, Z = 4, Rgt(F) = 0.0121, wRref(F2) = 0.0304, T = 200 K.

CCDC no.:: 1267/4323

Source of material

The title compound was obtained upon reacting 1,2-dimethylimidazole with hydroiodic acid in ethanol. Crystals suitable for the diffraction study were obtained upon free evaporation of the solvent.

Table 1

Data collection and handling.

Crystal:Yellow blocks,
size 0.312×0.316×0.532 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:39.11 cm–1
Diffractometer, scan mode:Bruker APEX-II CCD, φ and ω
2θmax:56.62°
N(hkl)measured, N(hkl)unique:13957, 1992
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1975
N(param)refined:79
Programs:SHELX, WinGX, MERCURY,
PLATON [6–9]

Experimental details

Carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C–C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite [6]), with Uiso(H) set to 1.5Ueq(C). The nitrogen-bound H atom was located on a difference Fourier map and refined freely.

Table 2

Atomic coordinates and displacement parameters (in Å2).

AtomSitexyzUiso
H(1A)4a0.18270.24990.35560.064
H(1B)4a0.41560.25060.35420.064
H(1C)4a0.29840.11640.29800.064
H(3A)4a0.70980.28110.10870.068
H(3B)4a0.60070.13110.15120.068
H(3C)4a0.68680.25830.22540.068
H(4)4a0.11820.54640.06980.055
H(5)4a0.02440.42800.22970.048
H(2)4a0.454(4)0.452(3)0.035(2)0.059(7)
Table 3

Atomic coordinates and displacement parameters (in Å2).

AtomSitexyzU11U22U33U12U13U23
I(1)4a0.77860(2)0.44727(1)0.419734(7)0.03629(6)0.04103(6)0.02785(6)0.00200(4)−0.00477(4)−0.00289(4)
N(1)4a0.2959(2)0.3214(2)0.2258(1)0.0314(6)0.0354(6)0.0283(6)−0.0060(6)−0.0002(6)0.0008(5)
N(2)4a0.3769(2)0.4219(2)0.0869(1)0.0438(8)0.0461(8)0.0316(7)−0.0095(6)0.0030(7)0.0058(7)
C(1)4a0.2983(3)0.2267(2)0.3159(1)0.047(1)0.052(1)0.0301(8)−0.0096(9)−0.0022(8)0.0090(7)
C(2)4a0.4375(2)0.3269(2)0.1583(1)0.0309(7)0.0371(8)0.0303(8)−0.0089(7)−0.0003(6)−0.0020(6)
C(3)4a0.6244(3)0.2422(3)0.1611(2)0.0332(9)0.057(1)0.045(1)−0.0014(8)−0.0018(8)−0.0072(9)
C(4)4a0.1939(3)0.4770(2)0.1085(2)0.046(1)0.045(1)0.046(1)0.0013(8)−0.0034(9)0.0104(8)
C(5)4a0.1436(3)0.4127(2)0.1955(1)0.0355(8)0.0436(9)0.0411(9)0.0004(7)0.0011(8)0.0014(7)

Discussion

The crystallization of ionic compounds is strongly influenced by the relative spatial size ratio of anion to cation, and the presence of different anions may influence on the conformation and as well as metric parameters of the cation in the case of bigger, organic cations. At the beginning of a comprehensive study of the influence of various anions on bond lengths and angles among a series of nitrogen-derived cations, the title compound featuring a simple anion was synthesized. The crystal and molecular structures of several other salts of 1,2-dimethylimidazole are apparent in the literature, such as the chloride [1], the picrate [2], the nitrate [2] or the fumarate [3] to name but a few. The title compound is the iodide salt of the 1,2-dimethylimidazolium cation. Protonation occurred on the non-methylated nitrogen atom. The molecules is essentially planar (r.m.s of all fitted non-hydrogen atoms = 0.0097 Å) with the methylated nitrogen atom deviating most from the least-squares plane by 0.0186(13) Å. Intracyclic angles cover a range of 106.19(17)–110.08(16)° with the largest angle found on the protonated nitrogen atom. In the crystal, classical hydrogen bonds of the N–H⋯I type are observed that connect the cation and anion to isolated units. In terms of graph-set analysis [4, 5], the descriptor for these contacts is D on the unary level. The shortest intercentroid distance between two aromatic systems was measured at 5.7895(11) Å.

Corresponding author: Richard Betz, Nelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa, e-mail:

Acknowledgments:

The authors thank Ms. Sandi Eybers for helpful discussions.

References

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5. Etter, M. C.; MacDonald, J. C.; Bernstein, J.: Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr. B46 (1990) 256–262.Search in Google Scholar

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Received: 2015-1-15
Accepted: 2015-6-2
Published Online: 2015-9-26
Published in Print: 2015-12-1

©2015 Eric C. Hosten et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
https://doi.org/10.1515/ncrs-2014-9026
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
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