Startseite Naturwissenschaften Crystal structure of the salt 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) diperchlorate, C14H28N4(ClO4)2
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Crystal structure of the salt 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) diperchlorate, C14H28N4(ClO4)2

  • Gao-Ju Wen EMAIL logo und Lian-Shuai Gu
Veröffentlicht/Copyright: 9. Oktober 2017

Abstract

C14H28N4O8Cl2, monoclinic, P21/n a = 8.7538(18) Å, b = 11.393(2) Å, c = 9.942(4) Å, β = 97.50(3)°, V = 983.1(5) Å3, Z = 2, Rgt(F) = 0.0706, wRref(F2) = 0.2036, T = 293(2) K.

CCDC no.:: 1527555

The 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:colorless block
Size:0.20 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.38 mm−1
Diffractometer, scan mode:Rigaku RAPIDII, ω-scans
2θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:6531, 2254, 0.083
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1757
N(param)refined:127
Programs:Rigaku programs [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
N10.6575(2)0.90612(16)0.6044(2)0.0251(5)
N20.7986(3)0.7339(2)0.7379(2)0.0383(6)
C10.5962(3)0.8879(2)0.7392(3)0.0343(6)
H1A0.48470.88270.72490.041*
H1B0.62530.95350.79940.041*
C20.6655(4)0.7735(3)0.8023(3)0.0429(7)
H2A0.69750.78560.89840.052*
H2B0.58720.71280.79280.052*
C30.8296(3)0.9301(2)0.6356(3)0.0347(6)
H3A0.84651.00680.67720.042*
H3B0.87630.92930.55230.042*
C40.9037(3)0.8343(3)0.7331(3)0.0420(7)
H4A0.99890.80780.70300.050*
H4B0.92830.86710.82340.050*
C50.6372(3)0.7927(2)0.5237(3)0.0323(6)
H5A0.66410.80500.43320.039*
H5B0.53060.76740.51580.039*
C60.7426(4)0.6983(2)0.5977(3)0.0424(7)
H6A0.68620.62510.59890.051*
H6B0.83000.68500.54870.051*
C70.5853(3)1.0103(2)0.5277(3)0.0301(6)
H7A0.64221.02760.45270.036*
H7B0.59301.07800.58730.036*
Cl10.77899(8)0.90725(7)0.17026(8)0.0442(3)
O10.8337(5)0.9569(4)0.2973(3)0.1199(16)
O20.6277(4)0.9380(4)0.1235(6)0.1373(18)
O30.8819(4)0.9364(3)0.0773(3)0.0834(10)
O40.7820(4)0.7810(3)0.1805(5)0.1056(13)

Source of material

1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium)dibromide was synthesised according to the method of Abbiss et al. [3]. 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2] octan-1-ium) dibromide (4.118 g, 10 mmol) and NaClO4⋅H2O (2.809 g, 20 mmol) were mixed and stirred in aqueous solution (30 mL). Crystals were obtained by slow evaporation at room temperature with a yield of 86%. C14H28Cl2N4O8 (451.3): Cacld. (%): C, 37.26; H, 6.25; N, 12.41; O, 28.36. Found: C, 36.41; H, 6.94; N, 13.11; O, 28.59. IR (KBr disc, v, cm−1): 459, 625, 914, 1052, 1454, 1466, 2245, 2870, 2951, 3310.

Experimental details

Hydrogen atoms were placed in calculated positions and refined as a riding mode, with C–H = 0.96 Å (methylene) with Uiso(H) = 1.2 Ueq(C).

Discussion

Organic-inorganic crystalline materials can be exploited for many purposes such as nonlinear optical materials, dielectric, piezoelectric, pyroelectric, ferroelectric, semiconductors and other physical properties [4], [5], [6], [7]. Salts, co-crystals, polymorphs, solvates and hydrates are of general interest. Furthermore, there is a research interest in organic salts because of their brilliant properties [8], [9], [10], [11]. The basic structural unit of the compound comprises two perchlorate anions and one 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) cation. The perchlorate anions adopt tetrahedral geometry with Cl—O bond length of 1.390(4)–1.442(3) Å and bond angles from 105.9(2)° to 113.3(3)°. The diazabicyclo[2.2.2]octane moiety (cf. the figure) in the cation has a little torsion with the torsion angle of N—C—C—N ranging from 15.0(3)° to 15.9(3)°, which loses its typical D3h symmetry. Two kinds of weak hydrogen bonds, C—H⋯-N and C—H⋯-O, form a three dimensional network. The cation chains are parallel to the (101) plane and extend along b axis. The perchlorate anions also have two orientations which fill in the inner cation layers connecting the chains via C—H⋯-O (dH⋯-A = 2.53–2.57 Å) becoming 3D hydrogen bond network.

References

Rigaku: RAPID-AUTO. Rigaku Corporation, Tokyo, Japan (1998).Suche in Google Scholar

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

Abbiss, T. P.; Mann, F. G.: 414. The interaction of triethylenediamine and dibromomethane, 1,2-dibromoethane, and 1,3-dibromopropane. J. Chem. Soc. (1964) 2248–2254.10.1039/jr9640002248Suche in Google Scholar

Adhikari, S.; Seth, S. K.; Kar, T.: Structural studies and physicochemical properties of L-valine hydrochloride monohydrate. CrystEngComm 15 (2013) 7372–7379.10.1039/c3ce41079jSuche in Google Scholar

Bednarchuk, T. J.; Kinzhybalo, V.; Bednarchuk, O.: Synthesis, structural characterization, IR- and Raman spectroscopy, magnetic properties of new organically templated metal sulfates with 4-aminopyridinium. J. Mol. Struct. 1120 (2016) 138–149.10.1016/j.molstruc.2016.05.024Suche in Google Scholar

Czapla, Z.; Dacko, S.: Ferroelectric phase transition in hydrogen-bonded 2-aminopyridine phosphate (NC4H4NH2)H3PO4. J. Phys.: Condens. Matter 15 (2003) 3793–3803.10.1088/0953-8984/15/22/313Suche in Google Scholar

Ghazaryan, V. V.; Fleck, M.; Petrosyan, A. M.: New chemical analogs of triglycine sulfate. J. Cryst. Growth 401 (2014) 857–862.10.1016/j.jcrysgro.2013.11.054Suche in Google Scholar

Keramatnia, F.; Shayanfar, A.; Jouyban, A.: Thermodynamic solubility profile of carbamazepine ccinnamic acid cocrystal at different pH. J. Pharm. Sci. 104 (2015) 2559–2565.10.1002/jps.24525Suche in Google Scholar PubMed

Huang, N.; Rodriguez-Hornedo, N.: Engineering cocrystal solubility, stability, and pHmax by micellar solubilization. J. Pharm. Sci. 100 (2011) 5219–5234.10.1002/jps.22725Suche in Google Scholar PubMed

Kobayashi, J.; Enomoto, Y.; Sato, Y.: A phenomenological theory of dielectric and mechanical properties of improper ferroelectric crystals. Phys. Status Solidi 50 (1972) 335–C343.10.1002/pssb.2220500139Suche in Google Scholar

Vlokh, O. G.; Kapustianik, V. B.; Polovinko, I. I.: Influence of domain structure on electro-and piezooptic properties of NH2(CH3)2Al(SO4)2 × 6H2O crystals. Ferroelectrics 111 (1990) 333–337.10.1080/00150199008224419Suche in Google Scholar

Received: 2017-3-23
Accepted: 2017-9-13
Published Online: 2017-10-9
Published in Print: 2017-11-27

©2017 Gao-Ju Wen et al., 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. Crystal structure of potassium 1-methyl-1H-1,2,3,4-tetrazole-5-thiolate, C2H3N4SK
  3. Crystal structure of bis(3-(3-ethylureido)-N,N-dimethylpropan-1-aminium) bis (μ3-2-(hydroxymethyl)-2-(oxidomethyl)propane-1,3-bis(olato))-(μ6-oxo)-hexakis(μ2-oxo)-hexaoxo-hexavanadium(V) – dichloromethane (1/1), C27H60Cl2N6O23V6
  4. Crystal structure of bis(μ3-methanolato-κ3O:O:O)-bis(μ2-methanolato-κ2O:O)-dimethanol-bis{6,6′-(1,3-dihydroxyl-2-acetylpropane-1,3-diyl)bis(2-chloro-4-bromophenolato)}tetramanganese(III) C40H40Br4Cl4Mn4O16
  5. Synthesis and crystal structure of tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dibromo-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5)tetramanganese(III), C40H40Br8Mn4O16
  6. Synthesis and crystal structure tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dichloro-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5), tetramanganese(III), C40H40Cl8Mn4O16
  7. Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O)}copper(II), C34H34CuN4O6
  8. Crystal structure of (E)-1-(2-hydroxy-3-{[2-hydroxybenzylidene]amino}phenyl)ethan-1-one, C15H13NO3
  9. Crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′′:O′′}tricobalt(II), C44H49Cl2Co3N6O12
  10. Crystal structure of bis{μ2-2,4-dichloro-6-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ5O:O,N,N′,O′}dicobalt(II) acetone solvate, C43H48Br4Co2N6O9
  11. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3
  12. Crystal structure of bis{5-(N,N′-diethylamine)-5′-methoxy -2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato}-bis(μ2-acetato-κ2O:O′)trizinc(II), C46H56Zn3N6O14
  13. Crystal structure of tris(cyano-(hydrogen tris(3,5-dimethylpyrazolyl)borate))-iron(III) 4-methoxypyridinium monohydrate, C24H32BN10O2Fe
  14. Synthesis and crystal structure of bis{1-(((4-(1-(hydroxyimino)ethyl)phenyl)imino)methyl)naphthalen-2-olato-κ2O,N}copper(II), C38H30CuN4O4
  15. Crystal structure of (E)-1-(4-{[(E)-2-Hydroxy-1-naphthalenylmethylene] amino}phenyl)ethanone oxime, C19H16N2O2
  16. The pseudosymmetric crystal structure of 2-(2-naphthalenyl)-3-nitro-2H-1-benzopyran, C38H26N2O6
  17. Crystal structure of 2-benzoyl-3-(4-methoxyphenyl)cyclopropane-1,1-dicarbonitrile, C19H14N2O2
  18. N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C17H21N3O5
  19. The crystal structure of carbonyl-[4-(2,4-dichlorophenylamino)pent-3-en-2-onato-κ2N,O]-(triphenylphosphine-κP)rhodium(I), RhC30H25Cl2NO2P
  20. Crystal structure of (E)-5-(diethylamino)-2-(((1,1,2-trihydroxyethyl)iminio)methyl)phenolate, C15H24N2O4
  21. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)(μ2-isophthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C34H30N4O4Cd
  22. Crystal structure of 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]chinolizinium 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate - methanol - water (1/1/1), C36H33NO10
  23. A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3
  24. Crystal structure of the salt 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) diperchlorate, C14H28N4(ClO4)2
  25. Crystal structure of 2,5-bis((E)-2-(trifluoromethyl)benzylidene)cyclopentan-1-one, C21H14F6O
  26. Crystal structure of catena-poly[(μ2-benzene-1,4-dicarboxylato-κ2O:O′)-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)zinc(II)] 1.25 hydrate, C25H26.5N3O8.25FZn
  27. Crystal structure of 1-methyl-1,4-diazabicyclo[2.2.2]octan-1-ium poly[aqua-bis(μ2-perchlorato-κ3O,O′:O′′)sodium], C7H17Cl2N2NaO9
  28. Crystal structure of trimethyammonium 2,6-dicarboxyisonicotinate monohydrate, C11H16N2O7
  29. Crystal structure of dodecaguanidinium bis(tetrapropylammonium) heptacarbonate, C43H128N38O21
  30. Crystal structure of poly[tetraaqua-bis(μ6-benzene-1,2,4,5-tetracarboxylato)nickel(II)diyttrium(III)]dihydrate, C20H16NiO22Y2
  31. Halogen bonds and π–π interactions in the crystal structure of 1,3,5-trifluoro-2,4,6-triiodobenzene–N,N-dimethylformamide (1/1), C9H7F3I3NO
  32. Crystal structure of guanidinium tetraethylammonium carbonate dihydrate, C10H30N4O5
  33. The crystal structure of oxonium chlorido-ethylenediaminetetraactetotin(IV) hydrate, C10H17ClN2O10Sn
  34. Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4
  35. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}copper(II), C40H38CuN4O6
  36. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri(p-tolyl)phosphine-κP)rhenium(I), C29H28O5PRe
  37. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(benzyldiphenylphosphine-κP)rhenium(I), C27H24O5PRe
  38. Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8
  39. Crystal structure of bis(N,N,N-ethyldimethylethanaminium) bis(heptaselenido-κ2Se1,Se7)palladate(II), C12H32N2PdSe14
  40. Crystal structure of bis(4-(1H-pyrazol-5-yl)pyridine-κ2N:N′)-bis(2-(2-((2,6-difluorophenyl)amino)phenyl)acetate-κO)cadmium(II), C44H34N8CdCl4O4
  41. Crystal structure of 4,4′-(1,4-phenylene)bis(pyridin-1-ium) catena-poly[diaqua-bis(μ2-3′,5′-dicarboxy-[1,1′-biphenyl]-2,5-dicarboxylato-κ2O:O′] dihydrate, C48H42O22N2Ca
  42. The crystal structure of (S)-2-benzylsuccinic acid, C11H12O4
  43. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)yttrium(III)], C26H17N2O9Y
  44. Crystal structure of ethyl 1-(3,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate, C14H17N3O2
  45. Crystal structure of tetrakis(methanol-κO)-bis{μ2-3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olate-κ4O,N;O′:O′}dizinc(II), C38H38Zn2N2O14
  46. Crystal structure of bromido(4,4′-dimethoxy-2,2′-bipyridine-κ2N,N′)(isopropyl(diphenyl)phosphane-κP)copper(I), C27H29BrCuN2O2P
  47. Crystal structure of bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene, C41H64B2O4
  48. Crystal structure of 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde - a julolidine derivative, C16H15NO3
  49. Crystal structure of 1,3-dimethyl-5,5-dibenzylbarbituric acid, C20H20N2O3
  50. Crystal structure of bis(N,N,N-trimethylethanaminium) poly[bis(μ2-heptaselenido-κ2Se1,Se7)palladate(II)], C10H28N2PdSe14
  51. Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl} ethanone O-ethyl-oxime, C17H17ClN2O2
  52. The crystal structure of methyl N-(4-bromophenyl)carbamate, C8H8BrNO2
  53. Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2
  54. Crystal structure of 1,1′-butanebis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C12H20F12N4P2
  55. (E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S
  56. Crystal structure of ethyl 5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate, C11H12N4O2
  57. Crystal structure of 5,5-difluoro-10-(4-fluorophenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine - a Z′ = 3 structure, C19H18B2F3N2
  58. The crystal structure of the Matrine derivative: 12-(1H-indol-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one hydrate, C23H29N3O
  59. 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-κ2O,O′)dilutetium(III), C50H38F18Lu2O16
  60. The crystal structure of (Z)-2-(3-(2-(4-chlorobenzoyl)hydrazono)-2-oxoindolin-1-yl) acetic acid, C17H12ClN3O4
  61. Synthesis and crystal structure of trans-tetraqua-bis(2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetato-κO)cobalt(II) hexahydrate, C36H48CoN2O28S2
  62. The crystal structure of N,N-dimethyl-2,6-di-p-tolylpyrimidin-4-amine, C20H21N3
  63. The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S
  64. Crystal structure of catena-poly[(μ2-1,3-bis(benzimidazol-1-yl)propane κ2N:N′)-(μ2-5-methoxyisophthalato-κ2O:O′)zinc(II)] hydrate, C26H24ZnN4O6
  65. The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3
  66. Crystal structure of 2,8-diphenyl-3,7,9-trioxa-1-azaspiro[4.5]dec-1-ene, C18H17N1O3
  67. Crystal structure of diethyl 2-(4-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19ClO6
  68. Crystal structure of 1-(carboxymethyl)-1H-benzo[d][1,2,3]triazole 3-oxide, C8H7N3O3
  69. Crystal structure of (acetylacetonato-κ2O,O′)-(2-amino-6-chlorobenzoato-κO)-oxido(1,10-phenanthroline-κ2N,N′)vanadium(IV) – trichloromethane (1/1)
  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
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