Startseite The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridozincate(II) monohydrate, C10H18Cl4ZnN2O
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The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridozincate(II) monohydrate, C10H18Cl4ZnN2O

  • Guido J. Reiss EMAIL logo und Alena Sergeeva
Veröffentlicht/Copyright: 9. April 2020
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 235 Heft 4

Abstract

C10H18Cl4ZnN2O, orthorhombic, P212121 (no. 19), a = 7.0752(1) Å, b = 7.5085(1) Å, c = 29.3383(5) Å, V = 1558.57(4) Å3, Z = 4, Rgt(F) = 0.0330, wRref(F2) = 0.0672, T = 290(2) K.

CCDC no.: 1987280

The 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:Colourless plate
Size:0.13 × 0.54 × 0.80 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.25 mm−1
Diffractometer, scan mode:Xcalibur EOS, ω-scans
θmax, completeness:28°, >99%
N(hkl)measured, N(hkl)unique, Rint:22747, 3750, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3604
N(param)refined:179
Programs:CrysAlisPRO [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Zn10.33235(7)0.72221(6)0.62657(2)0.03149(11)
O1W0.6448(6)0.7405(5)0.50298(12)0.0562(9)
H1W0.597(8)0.811(6)0.5233(14)0.082(16)*
H2W0.689(8)0.798(6)0.4798(13)0.082(16)*
N10.8004(6)0.4450(5)0.54165(12)0.0376(8)
H10.762(7)0.540(7)0.5281(17)0.043(14)*
N1′0.7692(6)0.1462(5)0.68211(12)0.0369(9)
H1′0.786(7)0.043(6)0.6693(15)0.035(13)*
Cl10.3209(2)0.48652(14)0.57828(4)0.0428(3)
Cl20.03496(15)0.76693(15)0.65426(3)0.0394(2)
Cl30.53251(18)0.6885(2)0.68610(4)0.0531(3)
Cl40.4349(2)0.95560(17)0.58342(4)0.0575(4)
C20.8081(6)0.4413(5)0.58728(14)0.0324(8)
H20.7720460.5407260.6040660.039*
C30.8691(5)0.2911(5)0.60908(12)0.0267(8)
C40.9179(6)0.1450(6)0.58296(13)0.0325(9)
H40.9603270.0415860.5970850.039*
C50.9041(6)0.1515(6)0.53576(14)0.0364(10)
H50.9352390.0529610.5180690.044*
C60.8434(6)0.3062(6)0.51589(13)0.0385(10)
H60.8324940.3136900.4843610.046*
C2′0.8895(6)0.2897(6)0.66041(12)0.0309(8)
H2′0.8492950.4056640.6722830.037*
C3′1.0873(6)0.2499(7)0.67813(14)0.0422(11)
H3A1.1572240.3595080.6828180.051*
H3B1.1560570.1762400.6566140.051*
C4′1.0607(9)0.1516(7)0.72322(16)0.0526(13)
H4A1.1250260.0375800.7224850.063*
H4B1.1112980.2213050.7482420.063*
C5′0.8526(9)0.1256(8)0.72893(15)0.0535(13)
H5A0.8008820.2140210.7495590.064*
H5B0.8258630.0080280.7410210.064*
C6′0.5640(7)0.1874(8)0.68251(18)0.0524(13)
H6A0.5198600.2011130.6517660.079*
H6B0.5428790.2959530.6990450.079*
H6C0.4966650.0919200.6969660.079*

Source of materials

In a representative experiment 0.161 mL (0.162 g; 1 mmol) S-nicotine ((S)-3-[1-methylpyrrolidin-2-yl]pyridine; Acros Organics) were dissolved in a few drops of concentrated hydrochloric acid (Merck KGa). To the aforementioned solution 0.136 g (1 mmol; Riedel de Haen) of ZnCl2 were added. This mixture was heated to 85 °C, giving a colourless solution. Colourless plate crystals of the title compound were obtained by slow evaporation at room temperature within a few days.

Raman Spectrum (Bruker MultiRam; resolution: 4 cm−1) [cm−1]: 3092(m), 3066(w), 3031(m), 2964(s, br), 2892(w), 2852(w), 1644(m), 1460(m, br), 1382(w), 1240(m), 1189(m), 1052(s), 1029(s), 902(m), 787(m), 619(m), 562(w), 525(w), 400(br, w), 321(m), 280(s), 220(s), 145(vs) 126 (vs); 100 (vs).

Experimental details

Coordinates of hydrogen atoms attached to nitrogen were refined without any constraints or restraints. The hydrogen atoms of the water molecule were refined using one O—H distance restraint and one common Uiso parameter. The carbon-bound hydrogen atoms were placed using a riding model (AFIX 13/23/43/137) implemented in the SHELXL system using the standard parameters for the constrained Uiso(H) values [3]. The absolute structure determination succeeded as the derived Flack parameter is found to be near zero with a low standard uncertainty [0.007(4) from 1388 selected quotients] using Parsons’s method [5]. The classical calculation of the Flack parameter showed a slightly worse result 0.023(18) using all reflections [3], [5].

Comment

A recently conducted Cambridge Structural Database [6] survey on nicotine-containing structures confirms that about fifty structures are deposited that contain a nicotine-fragment. As reported and summarized by one of us [7] structural data are available for (a) metal complexes, which contain neutral nicotine ligands; (b) a small number of co-crystals containing neutral nicotine as one of the components; (c) some examples for pyrrolidinyl-protonated nicotinium salts; (d) and mono-protonated nicotinium as a cationic ligand. As a result of the database survey specified above, only 7 examples of salt structures containing doubly protonated nicotinium cations have been reported so far [7], [8], [9], [10], [11], [12]. This contribution is part of our continuing interest in synthesis, characterization and understanding of hydrogen-bonding schemes of salts of natural products [7], [11], [12], [13], [14].

Description. The asymmetric unit of the title structure contains one 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium (nicotin-1,1′-dium) dication (nicH2), one tetrachloridozincate(II) dianion and one water molecule. As discussed in our preceding contributions [7], [11], [12], the protonation at the nitrogen atom of the pyrrolinyl moiety creates a second chiral center at N2 (cf. the Figure), which shows R configuration in accord with the literature. This R configuration at the nitrogen atom of the pyrrolinyl moiety seems to be the predominant protonation path. The title structure is isomorphous to the literature known structure of nicH2[CoCl4] ⋅ H2O [12]. The four carbon atoms of the pyrrolidinyl moiety are almost planar (RMS deviation = 0.02 Å) with the N1′ atom folded out of this plane by 0.56(1) Å. The best plane defined by the carbon atoms C2′, C3′, C4′, C5′ encloses an angle of 76.9(2) Å with the mean plane of the pyridinyl moiety (see the figure). This parameter represents the flexibility of the nicotin-1,1′-diium cation in the solid state. This variability around the C3—C2′ single bond is obviously more or less a consequence of the packing and hydrogen-bonding schemes, respectively. The bond lengths and angles within the nicH2 dication [7], [11], [12] as well as those in the [ZnCl4]2− ion [15], [16], [17] are in the expected ranges. The Zn–Cl bond lengths of the chlorido ligands of the complex [ZnCl4]2− anion range from 2.2628(12) Å to 2.2803(12) Å. Comparing the [ZnCl4]2− anion with related H3N-R-ZnCl3-complexes [18], which may form an intramolecular NH⋯Cl hydrogen bond, showed that the Zn—Cl bond lengths are slightly shorter than those in the title salt. The Raman spectrum (see the Source of Materials section) supports the finding of a slightly distorted [ZnCl4]2− anion. The assignment of the [ZnCl4]2− anions related Raman signals (80–300 cm−1) is not trivial. A detailed discussion on the assignment of the Raman signals for [ZnCl4]2− anions has been reported earlier [19]. Raman signals in the 400–3100 cm−1 range are as expected [11].

Supramolecular aspects. The nicH2 dication participates in a classical NH⋯O hydrogen bond to the water molecule (N⋯O = 2.724(5) Å; cf. the Figure), which is in accord with the isomorphous structure of NicH2[CoCl4] ⋅ H2O [12]. The NH group of the pyrrolinyl moiety is involved in a very weak NH⋯Cl hydrogen bond (N2⋯Cl2′ = 3.509(4) Å; ′ = x + 1, y − 1, z). This distance is significantly longer than that [3.309(4) Å] found in the low-temperature structure of the isomorphous structure of nicH2[CoCl4] ⋅ H2O [12], but in accord with the distance derived from the room-temperature structure [3.539(8) Å] of nicH2[CoCl4] ⋅ H2O [12]. Temperature has obviously a larger influence on intermolecular interactions than the interchange of Zn(II) by Co(II). The water molecule donates in total two hydrogen bonds to two [ZnCl4]2− dianions [O1⋯Cl4 = 3.222(4) Å; O1⋯Cl1′′ = 3.382(4) Å; ′′ = x + 1/2, −y + 3/2, −z + 1]. Neglecting the very weak NH⋯Cl hydrogen bond of the pyrrolidinyl moiety, a hydrogen-bonded chain structure running along the crystallographic a direction is obtained. Including the aforementioned very weak NH⋯Cl hydrogen bond a 2D network parallel to the ab plane is constructed by the connection of adjacent chains. This 2D description is also the most reliable description for the low-temperature structure of nicH2[CoCl4] ⋅ H2O [12].

Outlook. In continuation of this structural study we are still trying to crystallize more nicotin-1,1′-dium tetrahalogenidometallate salts for a detailed comparison and understanding of temperature and element dependent structural changes in groups of isomorphous structures. It may be of interest to test more nicotin-1,1′-dium tetrahalogenidometallate salts in catalysis as for other nicotin-1,1′-dium salts catalytic properties are observed [20], [21].

Acknowledgements

We gratefully acknowledge support by the Ministry of Innovation, Science and Research of North-Rhine Westphalia and the German Research Foundation (DFG) for financial support (Xcalibur diffractometer; INST 208/533-1). We thank E. Hammes for the technical support (Raman spectrum).

References

1. CrysAlis PRO, Oxford Diffraction Ltd., Abingdon, Oxfordshire, England (2006).Suche in Google Scholar

2. Sheldrick, G. M.: SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Suche in Google Scholar PubMed PubMed Central

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

4. Brandenburg, K.: DIAMOND. Visual Crystal Structure Information System. Ver. 4.0. Crystal Impact, Bonn, Germany (2015).Suche in Google Scholar

5. Parsons, S.; Flack, H. D.; Wagner, T.: Use of intensity quotients and differences in absolute structure refinement. ActaCrystallogr. B69 (2013) 249–259.10.1107/S2052519213010014Suche in Google Scholar PubMed PubMed Central

6. Groom, C. R.; Allen, F. H.: The Cambridge Structural Database in retrospect and prospect. Angew. Chem. Int. Ed. 53 (2014) 662–671.10.1002/anie.201306438Suche in Google Scholar PubMed

7. Reiss, G. J.: The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2. Z. Kristallogr. NCS 235 (2020) 415–417.10.1515/ncrs-2019-0717Suche in Google Scholar

8. Choi, S.-N.; Lee, Y.-M.; Lee, H.-W.; Kang, S. K.; Kim, Y.-I.: Nicotinium tetrachlorocuprate(II). Acta Crystallogr. E58 (2002) m583–m585.10.1107/S1600536802017154Suche in Google Scholar

9. Kang, S.-W.; Kim, H.-S.; and Kim, Y.-I.: Preparation and characterization of nicotinium tetrahalocuprate(II) and tetrahalocobaltate(II) complexes: structure of nicotinium tetrachlorocobaltate(II). Bull. Korean Chem. Soc. 27 (2006) 1877–1880.10.5012/bkcs.2006.27.11.1877Suche in Google Scholar

10. Koo, C. H.; Kim, H.-S.: The crystal structure of nicotine dihydroiodide. J. Korean Chem. Soc. 9 (1965) 34–41.Suche in Google Scholar

11. Reiss, G. J.: I5− Polymers with a layered arrangement: synthesis, spectroscopy and structure of a new polyiodide salt in the nicotine/HI/I2 system. Z. Naturforsch. B70 (2015) 735–739.10.1515/znb-2015-0092Suche in Google Scholar

12. Reiss, G. J.; Sergeeva, A.: The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridocobaltate(II) monohydrate, C10H18Cl4CoN2O. Z. Kristallogr. NCS 232 (2017) 159–161.10.1515/ncrs-2016-0245Suche in Google Scholar

13. Merkelbach, J.; Majewski, M. A.; Reiss, G. J.: Crystal structure of caffeinium triiodide — caffeine (1/1), C16H21I3N8O4. Z. Kristallogr. NCS 233 (2018) 941–944.10.1515/ncrs-2018-0125Suche in Google Scholar

14. Reiss, G. J.: A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2. Z. Kristallogr. NCS 234 (2019) 737–739.10.1515/ncrs-2019-0082Suche in Google Scholar

15. Akhtar, M.; Zierkiewicz, W.; Michalczyk, M.; Rüffer, T.; Lang, H.; Isab Anvarhusein, A.; Mazhar, M.; Ahmad, S.: Crystal structure and theoretical investigation of bis(cis-1,2-diaminocyclohexane)zinc(II) tetrachloridozincate(II). Z. Naturforsch. B72 (2017) 627–630.10.1515/znb-2017-0006Suche in Google Scholar

16. Rayes, A.; Mezzadri, F.; Issaoui, N.; Ayed, B.; Calestani, G.: Synthesis, physico-chemical studies, non-linear optical properties and DFT calculations of a new non-centrosymmetric compound: (3-ammoniumpyridinium) tetrachloridozincate(II). J. Mol. Struct. 1184 (2019) 524–531.10.1016/j.molstruc.2018.12.042Suche in Google Scholar

17. Song, Q.; Song, L.: Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn. Z.Kristallogr. NCS 232 (2017) 461–462.10.1515/ncrs-2016-0317Suche in Google Scholar

18. Reiss, G. J.: Two structurally related, hydrogen-bonded polymorphs of the zwitterionic complex trichlorido-((dimethylphosphoryl)methanaminium-κO) zinc(II). Main Group Met. Chem. 38 (2015) 125–130 and references cited therein.10.1515/mgmc-2015-0024Suche in Google Scholar

19. Carter, R. L.: Raman spectra of the double-anion salts M3ZnCl4NO3 (M+ = K+, Rb+, NH4+). Spectrochim. Acta A56 (2000) 2351–2363.10.1016/S1386-1425(00)00284-5Suche in Google Scholar

20. Tamaddon, F.; Azadi, D.: Synthesis and identification of nicotinium sulfate (3-(1-methylpyrrolidin-2-yl)pyridine : H2SO4) from tobacco-extracted nicotine: a protic ionic liquid and biocompatible catalyst for selective acetylation of amines. J. Mol. Liq. 255 (2018) 406–412.10.1016/j.molliq.2017.12.107Suche in Google Scholar

21. Tamaddon, F.; Azadi, D.: Nicotinium methane sulfonate (NMS): A bio-renewable protic ionic liquid and bi-functional catalyst for synthesis of 2-amino-3-cyano pyridines. J. Mol. Liq. 249 (2018) 789–794.10.1016/j.molliq.2017.10.153Suche in Google Scholar

Received: 2020-01-28
Accepted: 2020-02-29
Published Online: 2020-04-09
Published in Print: 2020-06-25

©2020 Guido J. Reiss et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of bis [1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O]cobalt(II), C24H22N8O4S2Co
  3. The crystal structure of 1,3-bis(4-(methoxycarbonyl)benzyl)-2-methyl-1H-benzo[d]imidazol-3-ium bromide, C26H25BrN2O4
  4. Crystal structure of {tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′}-(nitrito-κ2O,O′)nickel(II) perchlorate – ethanol (1/1), C26H27ClN8NiO7
  5. Crystal structure of catena-poly[aqua[(μ2-4,5-dicarboxylato-2-(2-carboxylatophenyl)imidazol-1-ido-κ4N,O,O′:N′)](μ2-4,4′-bipyridine-κ2N:N′)dicopper(II)], C22H14Cu2N4O7
  6. Crystal structure of chlorido-tris(4-methylbenzyl-κC)-(triphenylarsine oxide-κO)tin(IV), C42H42AsClOSn
  7. The crystal structure of 4,4′-bipyridinium bis(3-carboxy-2-nitrobenzoate) tetrahydrate, C13H13N2O8
  8. Crystal structure of 1-(3-chlorophenyl)-4-(4-(((2,3-dihydro-1H-inden-5-yl)oxy)methyl)phenethyl)piperazine, C28H31ClN2O
  9. Crystal structure of catena-poly[diaqua-bis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′:N′′,N′′′)magnesium], C10H8N20O2Mg
  10. The crystal structure of (E)-2-((2-hydroxy-4-ethoxybenzylidene)amino)-2-methylpropane-1,3-diol monohydrate, C13H21NO5
  11. Crystal structure of catena-poly[diaqua-(μ2-bipyridine-κ2N:N′)-bis(3,5-dichloroisonicotinato-κO)cadmium(II)] dihydrate, C22H20CdCl4N4O8
  12. The crystal structure of 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid, C13H15ClO2
  13. Redetermination of the crystal structure of yttrium(III) trinitrate(V) pentahydrate, Y(NO3)3 ⋅ 5 H2O, H10N3O14Y
  14. Crystal structure of catena-poly[di-μ2-chlorido-1,10-phenanthroline-κ2N,N′-cadmium(II)], C12H8Cl2CdN2
  15. Crystal structure of 4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)benzoic acid, C13H9F3N2O3
  16. Crystal structure of 3-acetyl-4-hydroxybenzoic acid, C18H16O8
  17. Crystal structure of bis(N,2-bis(4-ethoxybenzylidene)hydrazine-1-carbohydrazonothioato-κ2N,S)nickel(II) — N,N-dimethylformamide (1/2), C44H56N10S2O6Ni
  18. The crystal structure of 5-chloro-4,6-dimethoxypyrimidin-2-amine, C6H8ClN3O2
  19. Crystal structure of poly[aqua-(μ4-benzene-1,2,4,5-tetracarboxylato-κ4O,O′,O′′,O′′′)bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N)dinickel(II)], NiC17H14N5O5
  20. Crystal structure of poly[aqua(5-dimethylamino)naphthalene-1-sulfonato-κ2N:O)(μ2-4,4′-bipyridyl -κ2N:N′)silver(I)], C44H44Ag2N6O8S2
  21. Crystal structure of 1-[3-(trifluoromethyl)cinnamoyl]-3-(pyridin-2-yl-κN)pyrazole-κ2N-bis(2-phenylpyridinato-k2C,N)iridium(III) hexafluorophosphate complex, [C40H28F3IrN5O]PF6
  22. Crystal structure of catena-poly[aqua(μ6-piperazine-1,4-bisethanesulfonato-κ6N:N′:O:O′:O′′:O′′′)(μ2-pyrazinyl-κ2N:N′)disilver(I)sesquihydrate], C12H30Ag2N4O11S2
  23. Crystal structure of (E)-1-(2-nitrophenyl)-N-(o-tolyl)methanimine, C14H12N2O2
  24. Crystal structure of 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile, C19H22N2
  25. The crystal structure of poly[bis(N,N-dimethylformamide-κ1O)-tetrakis(μ2-cyanido-κ2C:N)dinickel(II)], C10H14N6O2Ni2
  26. Crystal structure of rac-trans-N,N′-bis(3-bromo-5-chlorosalicylidene)-1,2-cyclohexanediamine, C20H18Br2Cl2N2O2
  27. Crystal structure of rac-trans-N,N′-bis(3,5-dibromosalicylidene)-1,2-cyclohexanediamine, C20H18Br4N2O2
  28. The crystal structure of (dichromato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)nickel(II), C12H16N4O7Cr2Ni
  29. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridozincate(II) monohydrate, C10H18Cl4ZnN2O
  30. Crystal structure of bis(μ2-azido-k2N,N)-bis(2-amino-1-(N-(3-bromosalicylaldiminato))ethane)-dicopper(II), C20H18Br4N2O2
  31. Crystal structure of (η6-1-methyl-4-isopropylbenzene)-[5-bromo-2-(2-pyridyl)phenyl-κ2C,N]-chloro-ruthenium(II), C21H21BrClNRu
  32. Crystal structure of N-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ6-sulfanylidene)cyanamide, C10H10F3N3OS
  33. Crystal structure of 6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromo-4-chlorophenolato-κ4N,N′,O,O′)nickel(II), C20H16Br2Cl2NiN2O2
  34. Redetermination of the crystal structure of catena-poly[aqua-(1,10-phenanthroline-κ2N,N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)manganese(II) monohydrate, C12H12N2O6MoMn
  35. The crystal structure tetrakis(μ2-o-chlorobenzoato-κ2O:O′)-bis(methanol-κ1O)dirhodium(II), C30H24Cl4O10Rh2
  36. Crystal structure of bis(2,3-diphenyltetrazolidine-5-thione-κ1S)-(nitrato-κ1O)-(nitrato-κ2O,O′)lead(II), C26H20N10O6S2Pb
  37. Crystal structure of bis(3-bromo-N-(1-(3-methylpyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)cadmium(II) hemihydrate, C28H25N8O2.5Br2Cd
  38. Crystal structure of catena-poly[tetrakis(μ2-trifluoroacetato-κ2O:O′)(μ2-2,5-dimethylpyrazine-κ2N,N′)dicopper(II)], C7H4CuF6NO4
  39. The crystal structure of catena-poly[bis[3-azoniapentane-1,5-diammonium][bis(μ4-oxo)-tetrakis(μ3-oxo)-heptakis(μ2-oxo)-tetradecaoxo-octa-molybdenum] dihydrate], (C8H36N6O29Mo8)n
  40. Crystal structure of tetraaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κO)-nickel(II)—diaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-nickel(II), C28H24Cl12N4Ni2O18
  41. The crystal structure of bis(2-hydroxypyrimidinium) pentachloridobismuthate(III), (C4N2H5O)2BiCl5
  42. The crystal structure of catena-poly[(μ2-4,4′-dipyridine-κ2N,N′)-bis(3,5,6-trichloropyridine-2-oxyacetato-κO)-bis(ethanol-κO)nickel(II)], C28H26Cl6N4NiO8
  43. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C26H20Cl3F2NO3S
  44. The crystal structure of 5-bromopicolinic acid monohydrate, C6H6BrNO3
  45. The crystal structure of 2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-8H-indeno[1,2-d]thiazole, C25H17BrFN3S
  46. The crystal structure of catena-poly[(μ2-2-((3-bromo-2-oxidobenzylidene)amino)acetato-κ4O,N,O′:O′′)-(dimethylformamide-κ1O)]zinc(II), C12H13N2O4BrZn
  47. Crystal structure of aqua-azido-κ1N-(6,6′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-bromophenolato)-κ4N,N′,O,O′iron(III), C17H16Br2FeN5O3
  48. The crystal structure of tris(1-ethylimidazole-κ1N)-(sulfato-κ2O,O′)vanadium(IV), C15H24N6O5SV
  49. Crystal structure of (E)-3-methoxy-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide, C15H15N3O2
  50. Crystal structure of dichloro-bis-(1-butyl-1H-benzo[d]imidazole)-nickel(II), C22H28Cl2N4Ni
  51. The crystal structure of 2-(2,3-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one, C17H14O5
  52. The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO
  53. The crystal structure of 1,8-bis(pyridin-4-ylethynyl)anthracene-1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1), C62H32F4I2N4
  54. The crystal structure of 3,6-di-tert-butyl-1,8-diiodo-9-methyl-9H-carbazole, C21H25I2N
  55. The crystal structure of 8-((4-chlorophenylamino)methylene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C15H14ClNO4
  56. The crystal structure of catena-poly[oktaaqua-bis(μ2-4,4′-ethene-1,2-diyldipyridine-κ2N:N′)-(μ2-3,3′-(1-oxidodiazene-1,2-diyl)diphthalato-κ2O:O′)dicobalt(II)] dihydrate, C28H36N4O19Co2
  57. Crystal structure of (E)-1-(2-cyano-3-oxo-1-phenylprop-1-en-1-yl)-3,7-diphenylindolizine-6-carbonitrile, C31H19N3O
  58. Crystal structure of 1,1′-bis(diphenylphosphino)ferrocene-(1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-(O-isobutyl sulfurodithioito-κ2S,S′)copper(I), C39H37CuFeOP2S2
  59. Crystal structure of poly[(5-bimethylamino-1-naphthalenesulfonato-κO)-(μ3-hexamethylenetetramino-κ3N:N′:N′′)silver(I)] dihydrate, C36H52Ag2N10O8S2
  60. Crystal structure of poly[μ2-diaqua-(μ2-2-amino-4,5-dicyano-κ2N:N′-imidazol-1-ide)sodium(I)], C5H6N5O2Na
  61. Crystal structure of (1,3-propanediamine-κ2N,N′)(N-(3-aminopropyl)-α-methyl aspartato-κ4N,N′,O,O′)cobalt(III) chloride, C11H24ClCoN4O4
  62. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one-dichloromethane (1/1), C26H20Cl2F3NO3S
  63. Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl
  64. The crystal structure of tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(o-pyridyl)imidazoline-1-oxyl 3-oxide-κ2N,O)yttrium(III), C24H32N9O13Y
  65. Hydrogen bonding versus packing effects in the crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetraiodidozincate(II), C10H16I4ZnN2
  66. Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS
  67. Crystal structure of 1-(4-chloro-phenyl)-7-ethoxyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C18H12ClF2NO4
  68. Crystal structure of 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H14F2N2O4
  69. Crystal structure of octahydro-7aR,8′R-dimethylspiro[isobenzofuran-4(1H), 4′ (3′H)-[1H-7,9a]methanocyclohepta[c]pyran]-1′,3, 9′ (3aH,4′aH)-trione, C20H26O5
  70. Crystal structure of bis(5-ethoxy-2-(((1-hydroxy-2-methyl-3-oxidopropan-2-yl)imino)methyl)phenolato-κ3N,O,O’)manganese(IV) – methanol (1/1), C27H38MnN2O9
  71. Crystal structure of 8a,8a′′-oxybis(8aH-8,9-dioxa-3a1λ4-aza-8aλ4-borabenzo[fg]tetracene), C34H22B2N2O5
  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
https://doi.org/10.1515/ncrs-2020-0054
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Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of bis [1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O]cobalt(II), C24H22N8O4S2Co
  3. The crystal structure of 1,3-bis(4-(methoxycarbonyl)benzyl)-2-methyl-1H-benzo[d]imidazol-3-ium bromide, C26H25BrN2O4
  4. Crystal structure of {tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′}-(nitrito-κ2O,O′)nickel(II) perchlorate – ethanol (1/1), C26H27ClN8NiO7
  5. Crystal structure of catena-poly[aqua[(μ2-4,5-dicarboxylato-2-(2-carboxylatophenyl)imidazol-1-ido-κ4N,O,O′:N′)](μ2-4,4′-bipyridine-κ2N:N′)dicopper(II)], C22H14Cu2N4O7
  6. Crystal structure of chlorido-tris(4-methylbenzyl-κC)-(triphenylarsine oxide-κO)tin(IV), C42H42AsClOSn
  7. The crystal structure of 4,4′-bipyridinium bis(3-carboxy-2-nitrobenzoate) tetrahydrate, C13H13N2O8
  8. Crystal structure of 1-(3-chlorophenyl)-4-(4-(((2,3-dihydro-1H-inden-5-yl)oxy)methyl)phenethyl)piperazine, C28H31ClN2O
  9. Crystal structure of catena-poly[diaqua-bis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′:N′′,N′′′)magnesium], C10H8N20O2Mg
  10. The crystal structure of (E)-2-((2-hydroxy-4-ethoxybenzylidene)amino)-2-methylpropane-1,3-diol monohydrate, C13H21NO5
  11. Crystal structure of catena-poly[diaqua-(μ2-bipyridine-κ2N:N′)-bis(3,5-dichloroisonicotinato-κO)cadmium(II)] dihydrate, C22H20CdCl4N4O8
  12. The crystal structure of 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid, C13H15ClO2
  13. Redetermination of the crystal structure of yttrium(III) trinitrate(V) pentahydrate, Y(NO3)3 ⋅ 5 H2O, H10N3O14Y
  14. Crystal structure of catena-poly[di-μ2-chlorido-1,10-phenanthroline-κ2N,N′-cadmium(II)], C12H8Cl2CdN2
  15. Crystal structure of 4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)benzoic acid, C13H9F3N2O3
  16. Crystal structure of 3-acetyl-4-hydroxybenzoic acid, C18H16O8
  17. Crystal structure of bis(N,2-bis(4-ethoxybenzylidene)hydrazine-1-carbohydrazonothioato-κ2N,S)nickel(II) — N,N-dimethylformamide (1/2), C44H56N10S2O6Ni
  18. The crystal structure of 5-chloro-4,6-dimethoxypyrimidin-2-amine, C6H8ClN3O2
  19. Crystal structure of poly[aqua-(μ4-benzene-1,2,4,5-tetracarboxylato-κ4O,O′,O′′,O′′′)bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N)dinickel(II)], NiC17H14N5O5
  20. Crystal structure of poly[aqua(5-dimethylamino)naphthalene-1-sulfonato-κ2N:O)(μ2-4,4′-bipyridyl -κ2N:N′)silver(I)], C44H44Ag2N6O8S2
  21. Crystal structure of 1-[3-(trifluoromethyl)cinnamoyl]-3-(pyridin-2-yl-κN)pyrazole-κ2N-bis(2-phenylpyridinato-k2C,N)iridium(III) hexafluorophosphate complex, [C40H28F3IrN5O]PF6
  22. Crystal structure of catena-poly[aqua(μ6-piperazine-1,4-bisethanesulfonato-κ6N:N′:O:O′:O′′:O′′′)(μ2-pyrazinyl-κ2N:N′)disilver(I)sesquihydrate], C12H30Ag2N4O11S2
  23. Crystal structure of (E)-1-(2-nitrophenyl)-N-(o-tolyl)methanimine, C14H12N2O2
  24. Crystal structure of 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile, C19H22N2
  25. The crystal structure of poly[bis(N,N-dimethylformamide-κ1O)-tetrakis(μ2-cyanido-κ2C:N)dinickel(II)], C10H14N6O2Ni2
  26. Crystal structure of rac-trans-N,N′-bis(3-bromo-5-chlorosalicylidene)-1,2-cyclohexanediamine, C20H18Br2Cl2N2O2
  27. Crystal structure of rac-trans-N,N′-bis(3,5-dibromosalicylidene)-1,2-cyclohexanediamine, C20H18Br4N2O2
  28. The crystal structure of (dichromato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)nickel(II), C12H16N4O7Cr2Ni
  29. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridozincate(II) monohydrate, C10H18Cl4ZnN2O
  30. Crystal structure of bis(μ2-azido-k2N,N)-bis(2-amino-1-(N-(3-bromosalicylaldiminato))ethane)-dicopper(II), C20H18Br4N2O2
  31. Crystal structure of (η6-1-methyl-4-isopropylbenzene)-[5-bromo-2-(2-pyridyl)phenyl-κ2C,N]-chloro-ruthenium(II), C21H21BrClNRu
  32. Crystal structure of N-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ6-sulfanylidene)cyanamide, C10H10F3N3OS
  33. Crystal structure of 6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromo-4-chlorophenolato-κ4N,N′,O,O′)nickel(II), C20H16Br2Cl2NiN2O2
  34. Redetermination of the crystal structure of catena-poly[aqua-(1,10-phenanthroline-κ2N,N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)manganese(II) monohydrate, C12H12N2O6MoMn
  35. The crystal structure tetrakis(μ2-o-chlorobenzoato-κ2O:O′)-bis(methanol-κ1O)dirhodium(II), C30H24Cl4O10Rh2
  36. Crystal structure of bis(2,3-diphenyltetrazolidine-5-thione-κ1S)-(nitrato-κ1O)-(nitrato-κ2O,O′)lead(II), C26H20N10O6S2Pb
  37. Crystal structure of bis(3-bromo-N-(1-(3-methylpyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)cadmium(II) hemihydrate, C28H25N8O2.5Br2Cd
  38. Crystal structure of catena-poly[tetrakis(μ2-trifluoroacetato-κ2O:O′)(μ2-2,5-dimethylpyrazine-κ2N,N′)dicopper(II)], C7H4CuF6NO4
  39. The crystal structure of catena-poly[bis[3-azoniapentane-1,5-diammonium][bis(μ4-oxo)-tetrakis(μ3-oxo)-heptakis(μ2-oxo)-tetradecaoxo-octa-molybdenum] dihydrate], (C8H36N6O29Mo8)n
  40. Crystal structure of tetraaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κO)-nickel(II)—diaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-nickel(II), C28H24Cl12N4Ni2O18
  41. The crystal structure of bis(2-hydroxypyrimidinium) pentachloridobismuthate(III), (C4N2H5O)2BiCl5
  42. The crystal structure of catena-poly[(μ2-4,4′-dipyridine-κ2N,N′)-bis(3,5,6-trichloropyridine-2-oxyacetato-κO)-bis(ethanol-κO)nickel(II)], C28H26Cl6N4NiO8
  43. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C26H20Cl3F2NO3S
  44. The crystal structure of 5-bromopicolinic acid monohydrate, C6H6BrNO3
  45. The crystal structure of 2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-8H-indeno[1,2-d]thiazole, C25H17BrFN3S
  46. The crystal structure of catena-poly[(μ2-2-((3-bromo-2-oxidobenzylidene)amino)acetato-κ4O,N,O′:O′′)-(dimethylformamide-κ1O)]zinc(II), C12H13N2O4BrZn
  47. Crystal structure of aqua-azido-κ1N-(6,6′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-bromophenolato)-κ4N,N′,O,O′iron(III), C17H16Br2FeN5O3
  48. The crystal structure of tris(1-ethylimidazole-κ1N)-(sulfato-κ2O,O′)vanadium(IV), C15H24N6O5SV
  49. Crystal structure of (E)-3-methoxy-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide, C15H15N3O2
  50. Crystal structure of dichloro-bis-(1-butyl-1H-benzo[d]imidazole)-nickel(II), C22H28Cl2N4Ni
  51. The crystal structure of 2-(2,3-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one, C17H14O5
  52. The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO
  53. The crystal structure of 1,8-bis(pyridin-4-ylethynyl)anthracene-1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1), C62H32F4I2N4
  54. The crystal structure of 3,6-di-tert-butyl-1,8-diiodo-9-methyl-9H-carbazole, C21H25I2N
  55. The crystal structure of 8-((4-chlorophenylamino)methylene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C15H14ClNO4
  56. The crystal structure of catena-poly[oktaaqua-bis(μ2-4,4′-ethene-1,2-diyldipyridine-κ2N:N′)-(μ2-3,3′-(1-oxidodiazene-1,2-diyl)diphthalato-κ2O:O′)dicobalt(II)] dihydrate, C28H36N4O19Co2
  57. Crystal structure of (E)-1-(2-cyano-3-oxo-1-phenylprop-1-en-1-yl)-3,7-diphenylindolizine-6-carbonitrile, C31H19N3O
  58. Crystal structure of 1,1′-bis(diphenylphosphino)ferrocene-(1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-(O-isobutyl sulfurodithioito-κ2S,S′)copper(I), C39H37CuFeOP2S2
  59. Crystal structure of poly[(5-bimethylamino-1-naphthalenesulfonato-κO)-(μ3-hexamethylenetetramino-κ3N:N′:N′′)silver(I)] dihydrate, C36H52Ag2N10O8S2
  60. Crystal structure of poly[μ2-diaqua-(μ2-2-amino-4,5-dicyano-κ2N:N′-imidazol-1-ide)sodium(I)], C5H6N5O2Na
  61. Crystal structure of (1,3-propanediamine-κ2N,N′)(N-(3-aminopropyl)-α-methyl aspartato-κ4N,N′,O,O′)cobalt(III) chloride, C11H24ClCoN4O4
  62. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one-dichloromethane (1/1), C26H20Cl2F3NO3S
  63. Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl
  64. The crystal structure of tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(o-pyridyl)imidazoline-1-oxyl 3-oxide-κ2N,O)yttrium(III), C24H32N9O13Y
  65. Hydrogen bonding versus packing effects in the crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetraiodidozincate(II), C10H16I4ZnN2
  66. Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS
  67. Crystal structure of 1-(4-chloro-phenyl)-7-ethoxyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C18H12ClF2NO4
  68. Crystal structure of 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H14F2N2O4
  69. Crystal structure of octahydro-7aR,8′R-dimethylspiro[isobenzofuran-4(1H), 4′ (3′H)-[1H-7,9a]methanocyclohepta[c]pyran]-1′,3, 9′ (3aH,4′aH)-trione, C20H26O5
  70. Crystal structure of bis(5-ethoxy-2-(((1-hydroxy-2-methyl-3-oxidopropan-2-yl)imino)methyl)phenolato-κ3N,O,O’)manganese(IV) – methanol (1/1), C27H38MnN2O9
  71. Crystal structure of 8a,8a′′-oxybis(8aH-8,9-dioxa-3a1λ4-aza-8aλ4-borabenzo[fg]tetracene), C34H22B2N2O5
  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
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