Home The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
Article Open Access

The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N

  • Kina Muller , Eric C. Hosten ORCID logo and Richard Betz ORCID logo EMAIL logo
Published/Copyright: November 12, 2020
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 2

Abstract

C6H13Cl2N, orthorhombic, P212121 (no. 19), a = 6.0087(3) Å, b = 10.1176(6) Å, c = 14.3532(7) Å, V = 872.58(8) Å3, Z = 4, Rgt(F) = 0.0304, wRref(F2) = 0.0632, T = 200 K.

CCDC no.: 2041498

The molecular 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 platelet
Size:0.25 × 0.12 × 0.05 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.67 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:8227, 2165, 0.028
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1874
N(param)refined:88
Programs:Bruker [1], [2], SHELX [3], WinGX/ORTEP [4], Mercury [5], PLATON [6]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.75355 (13)−0.11634 (8)0.47932 (5)0.0507 (2)
N10.4071 (3)0.05003 (19)0.28772 (13)0.0261 (4)
H710.313 (4)0.123 (3)0.2987 (18)0.037 (7)*
C10.6381 (4)0.0916 (2)0.31382 (17)0.0298 (5)
H1A0.6839040.1676200.2748460.036*
H1B0.7428080.0179700.3019320.036*
C20.6483 (4)0.1300 (2)0.41544 (16)0.0329 (5)
H2A0.5594910.2113340.4250130.039*
H2B0.8044640.1502340.4321890.039*
C30.5619 (4)0.0230 (3)0.47933 (18)0.0347 (6)
H30.5509280.0591120.5440290.042*
C40.3342 (4)−0.0237 (3)0.44861 (17)0.0340 (6)
H4A0.2244600.0477120.4593870.041*
H4B0.289568−0.1006700.4868670.041*
C50.3302 (4)−0.0623 (2)0.34651 (17)0.0309 (5)
H5A0.428250−0.1396620.3364300.037*
H5B0.177013−0.0875510.3283360.037*
C60.3910 (5)0.0191 (3)0.18688 (16)0.0377 (6)
H6A0.501090−0.0486400.1708010.057*
H6B0.4199390.0992390.1505170.057*
H6C0.241342−0.0137860.1727440.057*
Cl20.12300 (10)0.29376 (6)0.30651 (5)0.03429 (15)

Source of material

The compound was obtained commercially (Fluka).

Experimental details

Carbon-bound H atoms were placed in calculated positions (C–H 0.99 Å for methylene groups and C–H 1.00 Å for methine groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atoms of the methyl group 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 [3]), with U(H) set to 1.5Ueq(C). The nitrogen-bound H atom was located on a difference Fourier map and refined freely. The compound was refined as an inversion twin with volume ratios of 6.64 and 93.36%.

Comment

Among the many effects that can be attributed to the spatial requirements of counterions have been the glass transition temperature in ionomers [7], surfactant modifying properties [8], the charge transfer in radical ions [9] and polymer-modified electrodes [10] as well as the structural and vibrational spectroscopic behaviour of DNA building blocks [11]. Furthermore, the benefit of choosing the adequate size of counterions to crystallize ionic compounds has been confirmed on many occasions [12]. In continuation of our interest in metrical features of large cations [13], [14], [15] the structure of the title compound has been determined. A comparable molecular connectivity pattern has been characterized structurally previously in form of the chloride [16] and perchlorate [17] salts of 4-chloro quinuclidinium.

The structure shows the presence of the chloride salt of a piperidinium derivative. The nitrogen atom is methylated while the intracyclic carbon atom in para position to the pnicogen atom features a chlorine substituent. N–C bond lengths span a range of 1.484(3)–1.498(3) Å with the shortest bond apparent to the exocyclic carbon atom. The C–Cl distance of 1.820(3) Å is in good agreement with the common values deposited with the Cambridge Structural Database [18]. While the methyl group on the tetrahedral nitrogen atom adopts an equatorial position on the central six-membered ring the chlorine atom is found to occupy an axial position. A conformational analysis of the heterocycle according to Cremer & Pople [19] shows the ring to adopt a 1C4 conformation on atoms N1 and C3 [20].

In the crystal, classical hydrogen bonds of the N–H···Cl type are observed next to C–H···Cl contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating in them. While the acceptor for all aforementioned interactions is invariably found in the chloride counterion, the C–H···Cl contacts are only supported by one hydrogen atom of the methyl group as well as the hydrogen atom of the chlorine-substituted intracyclic methylene group. In terms of graph-set analysis [21], [22], the descriptor for these contacts is DDD on the unary level.

Corresponding author: Dr. Richard Betz, Department of Chemistry, Nelson Mandela University, Summerstrand Campus (South), University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa, E-mail:

Funding source: National Research Foundation

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Research Foundation.

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

References

1. Bruker. APEX2; Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Search in Google Scholar

2. Bruker. SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2008.Search in Google Scholar

3. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122. https://doi.org/10.1107/s0108767307043930.Search in Google Scholar

4. Farrugia, L. J. WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 2012, 45, 849–854. https://doi.org/10.1107/s0021889812029111.Search in Google Scholar

5. Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez–Monge, L., Taylor, R., van de Streek, J., Wood, P. A. Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 2008, 41, 466–470. https://doi.org/10.1107/s0021889807067908.Search in Google Scholar

6. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. 2009, D65, 148–155. https://doi.org/10.1107/s090744490804362x.Search in Google Scholar

7. Enokida, J. S., Hu, W., Fang, H., Morgan, B. F., Beyer, F. L., Winter, H. H., Coughlin, E. B. Modifying the structure and dynamics of ionomers through counterion sterics. Macromolecules 2020, 53, 1767–1776. https://doi.org/10.1021/acs.macromol.9b02116.Search in Google Scholar

8. Oh, S. G., Shah, D. O. Effect of counterions on the interfacial tension and emulsion droplet size in the oil/water/dodecyl sulfate system. J. Phys. Chem. 1993, 97, 284–286. https://doi.org/10.1021/j100104a003.Search in Google Scholar

9. Piotrowiak, P., Miller, J. R. Counterion effects in intramolecular charge transfer in radical anions. J. Phys. Chem. 1993, 97, 13052–13060, https://doi.org/10.1021/j100152a004.Search in Google Scholar

10. Mathias, M. F., Haas, O. Effect of counterion type on charge transport at redox polymer-modified electrodes. J. Phys. Chem. 1993, 97, 9217–9225, https://doi.org/10.1021/j100138a025.Search in Google Scholar

11. Minguirbara, A., Vamhindi, B. S. D. R., Koyambo-Konzapa, S. J., Nsangou, M. Effects of counterions and solvents on the geometrical and vibrational features of dinucleoside-monophosphate (dNMP): case of 3′,5′-dideoxycytidine-monophosphate (dDCMP). J. Mol. Model. 2020, 26, 99. https://doi.org/10.1007/s00894-020-04369-6.Search in Google Scholar

12. Roof, L. C., Kolis, J. W. New developments in the coordination chemistry of inorganic selenide and telluride ligands. Chem. Rev. 1993, 93, 1037–1080. https://doi.org/10.1021/cr00019a010.Search in Google Scholar

13. Hosten, E. C., Betz, R. Redetermination of the crystal structure of benzyltriethylammoniumchloride monohydrate at 200 K – localization of hydrogen atoms, C13H24ClNO. Z. Kristallogr. NCS 2015, 230, 21–22. https://doi.org/10.1515/ncrs-2014-9024.Search in Google Scholar

14. Abrahams, A., van Brecht, B., Betz, R. Bis(pyridin-2-ylmethyl)ammonium nitrate. Acta Crystallogr. 2013, E69, o661. https://doi.org/10.1107/s1600536813008593.Search in Google Scholar

15. Betz, R., Gerber, T., Hosten, E., Siddaraju, B. P., Yathirajan, H. S. Opipramol dihydrochloride. Acta Crystallogr. 2011, E67, o2994–o2995. https://doi.org/10.1107/s1600536811042280.Search in Google Scholar

16. Kurahashi, M., Engel, P., Nowacki, W. The crystal structures of quinuclidinium chloride and 4-haloquinuclidinium chlorides. Z. Kristallogr. Cryst. Mater. 1980, 152, 147–156. https://doi.org/10.1524/zkri.1980.152.1-2.147.Search in Google Scholar

17. Kurahashi, M., Engel, P., Nowacki, W. The crystal structures of 4-haloquinuclidinium perchlorates. Z. Kristallogr. Cryst. Mater. 1980, 152, 135–146. https://doi.org/10.1524/zkri.1980.152.1-2.135.Search in Google Scholar

18. Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr. 2002, B58, 380–388. https://doi.org/10.1107/s0108768102003890.Search in Google Scholar

19. Cremer, D., Pople, J. A. General definition of ring puckering coordinates. J. Am. Chem. Soc. 1975, 97, 1354–1358. https://doi.org/10.1021/ja00839a011.Search in Google Scholar

20. Boeyens, J. C. A. The conformation of six-membered rings. J. Cryst. Mol. Struct. 1978, 8, 317–320. https://doi.org/10.1007/bf01200485.Search in Google Scholar

21. Bernstein, J., Davis, R. E., Shimoni, L., Chang, N.-L. Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555–1573. https://doi.org/10.1002/anie.199515551.Search in Google Scholar

22. Etter, M. C., MacDonald, J. C., Bernstein, J. Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr 1990, B46, 256–262.10.1107/S0108768189012929Search in Google Scholar PubMed

Received: 2020-10-03
Accepted: 2020-10-30
Published Online: 2020-11-12
Published in Print: 2021-03-26

© 2020 Kina Muller et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 4-hydroxybenzene-1,3-diaminium dichloride, C6H10Cl2N2O
  4. The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
  5. The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride, C4H11Cl2N
  6. Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
  7. Redetermination of the crystal structure of para-toluidine, C7H9N 
  8. The crystal structure of bis(1,3-dihydroxy-2-methylpropan-2-aminium) carbonate, C9H24N2O7
  9. The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
  10. Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
  11. The crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H21F2NO4
  12. Crystal structure of 6,6'‐((1E,1'E)‐(propane‐1,3‐diylbis(azaneylylidene))bis(methaneylylidene))bis(3‐bromophenol), C34H32Br4N4O4
  13. The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
  14. Crystal structure of (E)-4-bromo-N′-(3-chloro-2-hydroxybenzylidene)benzohydrazide, C14H10BrClN2O2
  15. Crystal structure of N,N′-bis(4-bromosalicylidene) ethylene-1,2-diaminopropan, C34H32Br4N4O4
  16. Crystal structure of 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H14Br2N2O3
  17. The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol — N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
  18. The crystal structure of para-trifluoromethyl-aniline hemihydrate, C14H14F6N2O
  19. Redetermination of the crystal structure of 2-amino-2-methyl-propane-1,3-diole, C4H11NO2
  20. The crystal structure of methacholine chloride, C8H18ClNO2
  21. Crystal structure of 5,7,7-trimethyl-4,6,7,8-tetrahydrocyclopenta[g]isochromen-1(3H)-one, C15H18O2
  22. Crystal structure of poly[diammine-bis(μ4-4-hydroxypyridine-3-sulfonato-κ5N:O, O′:O′′:O′′)(μ2-pyrazinyl-κ2N:N′)tetrasilver(I)], C7H8Ag2N3O4S
  23. Crystal structure of ethyl (E)-5-(((3′,6′-bis(ethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)imino)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate — ethanol (1/1), C38H45N5O5
  24. Crystal structure of 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, C14H7Br2N2O2
  25. Redetermination of the crystal structure of 3,3,3-triphenylpropanoic acid, C21H18O2 – Deposition of hydrogen atomic coordinates
  26. Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms
  27. Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N′′)cobalt(III), C7H19CoN12
  28. Crystal structure of tetraaqua-bis(1H-indazole-6-carboxylate-κN)cadmium (II), C16H18CdN4O8
  29. Crystal structure of dichloride-bis(1-propylimidazole-κ1N)zinc(II), C12H20Cl2N4Zn
  30. Crystal structure of (E)-resveratrol 3-O-β-D-xylopyranoside, C19H22O8
  31. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-vinyl- 1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C18H20F12N4P2
  32. Crystal structure of diaqua[bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″]-phthalato-κ1O-nickel(II)-methanol (1/2), C26H31N5NiO8
  33. Crystal structure of 6,7-difluoro-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one, C10H5F5N2O
  34. Crystal structure of dichlorido-bis(1-hexyl-1H-benzotriazole-k1N)zinc(II), C24H34N6Cl2Zn
  35. The crystal structre of 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H12BBrN2
  36. Crystal structure of diethyl 3,9-bis(4-fluorophenyl)-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C40H36F2N2O4
  37. Crystal structure of (E)-7-methoxy-2-((5-methoxypyridin-3-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one, C18H17NO3
  38. Crystal structure of (E)-2-chloro-6-(((1,3-dihydroxy-2-(oxidomethyl)propan-2-yl)imino)methyl)phenolate-κ3N,O,O’)manganese(IV), C22H24Cl2MnN2O8
  39. The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid, C15H14O4
  40. The crystal structure of N-(2-chloroethyl)-N,N-diethylammonium chloride, C6H15Cl2N
  41. The crystal structure of tris(2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium) trihydrodecavanadate(V), C27H54N6O28V10
  42. Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate C23H39ClN2O4
  43. Crystal structure of tetrakis[(Z)-(2-(1-(furan-2-yl)-2-methylpropylidene)-1-phenylhydrazin-1-ido-κ2N,N′)] zirconium(IV), C56H60N8O4Zr
  44. The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
  45. The crystal structure of trimethylsulfonium tris(trifluoromethylsulfonyl)methanide, C7H9F9O6S4
  46. Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
  47. The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S
  48. The crystal structure of N-(adamantan-1-yl)-piperidine-1-carbothioamide, C16H26N2S
  49. The crystal structure of 1-phenyl-N-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)-5-(thiophen-2-yl)-1H-pyrazole-3-carboxamide-dimethylformamide (1/1) C22H10Br4N4O3S
  50. The crystal structure of benzeneseleninic acid anhydride, C12H10O3Se2
  51. The crystal structure of diphenyalmine hydrochloride antimony trichloride co-crystallizate, C12H12Cl4NSb – Localization of hydrogen atoms
  52. The crystal structure of para-nitrobenzylbromide, C7H6BrNO2 – A second polymorph and correction of 3D coordinates
  53. Crystal structure of catena-poly[(5H-pyrrolo[3,2-b:4,5-b′]dipyridine-κ2N,N′)-(μ4-hexaoxidodivanadato)dizinc(II)],C10H9N3O6V2Zn
  54. Crystal structure of N,N′-(2-hydroxypropane-1,3-diyl)bis(pyridine-2-aldimine)-κ5N,N′,N′′,N′′′,O]-tris(nitrato-κ2O,O′) cerium(III), C15H16CeN7O10
  55. Synthesis and crystal structure of oktakis(dimethylsulphoxide-κ1O)gadolinium(III) [tetrabromido-μ2-bromido-μ2-sulfido-di-μ3-sulfido-μ4-sulfido-tetracopper(I)-tungsten(VI)], C16H48O8S12Br5Cu4GdW
  56. Crystal structure of {tris((1H-benzo[d]imidazol-2- yl)methyl)amine-κ4N,N′,N′′,N′′′}-(succinato-κ2O,O′)nickel(II) – methanol (1/4), C32H41N7NiO8
  57. Crystal structure of catena-poly[trans-tetraaqua(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-k2N:N′)cobalt(II)] dinitrate – 1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol) – water (1/3/2), C72H68CoN18O12
  58. Crystal structure of bis(μ2-2-oxido-2-phenylacetate-κ3O:O,O′)-bis(1-isopropoxy-2-oxo-2-phenylethan-1-olato-κ2O,O′)-bis(propan-2-olato-κ1O)dititanium(IV), C44H52O14Ti2
  59. The crystal structure of 5-carboxy-2-(hydroxymethyl)-1H-imidazol-3-ium-4-carboxylate, C6H8N2O6
  60. The crystal structure of 2,6-dibromo-4-fluoroaniline, C6H4Br2FN
  61. The crystal structure of 4-chloro-N-(2-phenoxyphenyl)benzamide, C19H14ClNO2
  62. The crystal structure of 2-methyl-β-naphthothiazole, C12H9NS
https://doi.org/10.1515/ncrs-2020-0522
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 4-hydroxybenzene-1,3-diaminium dichloride, C6H10Cl2N2O
  4. The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
  5. The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride, C4H11Cl2N
  6. Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
  7. Redetermination of the crystal structure of para-toluidine, C7H9N 
  8. The crystal structure of bis(1,3-dihydroxy-2-methylpropan-2-aminium) carbonate, C9H24N2O7
  9. The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
  10. Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
  11. The crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H21F2NO4
  12. Crystal structure of 6,6'‐((1E,1'E)‐(propane‐1,3‐diylbis(azaneylylidene))bis(methaneylylidene))bis(3‐bromophenol), C34H32Br4N4O4
  13. The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
  14. Crystal structure of (E)-4-bromo-N′-(3-chloro-2-hydroxybenzylidene)benzohydrazide, C14H10BrClN2O2
  15. Crystal structure of N,N′-bis(4-bromosalicylidene) ethylene-1,2-diaminopropan, C34H32Br4N4O4
  16. Crystal structure of 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H14Br2N2O3
  17. The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol — N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
  18. The crystal structure of para-trifluoromethyl-aniline hemihydrate, C14H14F6N2O
  19. Redetermination of the crystal structure of 2-amino-2-methyl-propane-1,3-diole, C4H11NO2
  20. The crystal structure of methacholine chloride, C8H18ClNO2
  21. Crystal structure of 5,7,7-trimethyl-4,6,7,8-tetrahydrocyclopenta[g]isochromen-1(3H)-one, C15H18O2
  22. Crystal structure of poly[diammine-bis(μ4-4-hydroxypyridine-3-sulfonato-κ5N:O, O′:O′′:O′′)(μ2-pyrazinyl-κ2N:N′)tetrasilver(I)], C7H8Ag2N3O4S
  23. Crystal structure of ethyl (E)-5-(((3′,6′-bis(ethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)imino)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate — ethanol (1/1), C38H45N5O5
  24. Crystal structure of 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, C14H7Br2N2O2
  25. Redetermination of the crystal structure of 3,3,3-triphenylpropanoic acid, C21H18O2 – Deposition of hydrogen atomic coordinates
  26. Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms
  27. Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N′′)cobalt(III), C7H19CoN12
  28. Crystal structure of tetraaqua-bis(1H-indazole-6-carboxylate-κN)cadmium (II), C16H18CdN4O8
  29. Crystal structure of dichloride-bis(1-propylimidazole-κ1N)zinc(II), C12H20Cl2N4Zn
  30. Crystal structure of (E)-resveratrol 3-O-β-D-xylopyranoside, C19H22O8
  31. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-vinyl- 1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C18H20F12N4P2
  32. Crystal structure of diaqua[bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″]-phthalato-κ1O-nickel(II)-methanol (1/2), C26H31N5NiO8
  33. Crystal structure of 6,7-difluoro-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one, C10H5F5N2O
  34. Crystal structure of dichlorido-bis(1-hexyl-1H-benzotriazole-k1N)zinc(II), C24H34N6Cl2Zn
  35. The crystal structre of 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H12BBrN2
  36. Crystal structure of diethyl 3,9-bis(4-fluorophenyl)-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C40H36F2N2O4
  37. Crystal structure of (E)-7-methoxy-2-((5-methoxypyridin-3-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one, C18H17NO3
  38. Crystal structure of (E)-2-chloro-6-(((1,3-dihydroxy-2-(oxidomethyl)propan-2-yl)imino)methyl)phenolate-κ3N,O,O’)manganese(IV), C22H24Cl2MnN2O8
  39. The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid, C15H14O4
  40. The crystal structure of N-(2-chloroethyl)-N,N-diethylammonium chloride, C6H15Cl2N
  41. The crystal structure of tris(2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium) trihydrodecavanadate(V), C27H54N6O28V10
  42. Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate C23H39ClN2O4
  43. Crystal structure of tetrakis[(Z)-(2-(1-(furan-2-yl)-2-methylpropylidene)-1-phenylhydrazin-1-ido-κ2N,N′)] zirconium(IV), C56H60N8O4Zr
  44. The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
  45. The crystal structure of trimethylsulfonium tris(trifluoromethylsulfonyl)methanide, C7H9F9O6S4
  46. Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
  47. The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S
  48. The crystal structure of N-(adamantan-1-yl)-piperidine-1-carbothioamide, C16H26N2S
  49. The crystal structure of 1-phenyl-N-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)-5-(thiophen-2-yl)-1H-pyrazole-3-carboxamide-dimethylformamide (1/1) C22H10Br4N4O3S
  50. The crystal structure of benzeneseleninic acid anhydride, C12H10O3Se2
  51. The crystal structure of diphenyalmine hydrochloride antimony trichloride co-crystallizate, C12H12Cl4NSb – Localization of hydrogen atoms
  52. The crystal structure of para-nitrobenzylbromide, C7H6BrNO2 – A second polymorph and correction of 3D coordinates
  53. Crystal structure of catena-poly[(5H-pyrrolo[3,2-b:4,5-b′]dipyridine-κ2N,N′)-(μ4-hexaoxidodivanadato)dizinc(II)],C10H9N3O6V2Zn
  54. Crystal structure of N,N′-(2-hydroxypropane-1,3-diyl)bis(pyridine-2-aldimine)-κ5N,N′,N′′,N′′′,O]-tris(nitrato-κ2O,O′) cerium(III), C15H16CeN7O10
  55. Synthesis and crystal structure of oktakis(dimethylsulphoxide-κ1O)gadolinium(III) [tetrabromido-μ2-bromido-μ2-sulfido-di-μ3-sulfido-μ4-sulfido-tetracopper(I)-tungsten(VI)], C16H48O8S12Br5Cu4GdW
  56. Crystal structure of {tris((1H-benzo[d]imidazol-2- yl)methyl)amine-κ4N,N′,N′′,N′′′}-(succinato-κ2O,O′)nickel(II) – methanol (1/4), C32H41N7NiO8
  57. Crystal structure of catena-poly[trans-tetraaqua(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-k2N:N′)cobalt(II)] dinitrate – 1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol) – water (1/3/2), C72H68CoN18O12
  58. Crystal structure of bis(μ2-2-oxido-2-phenylacetate-κ3O:O,O′)-bis(1-isopropoxy-2-oxo-2-phenylethan-1-olato-κ2O,O′)-bis(propan-2-olato-κ1O)dititanium(IV), C44H52O14Ti2
  59. The crystal structure of 5-carboxy-2-(hydroxymethyl)-1H-imidazol-3-ium-4-carboxylate, C6H8N2O6
  60. The crystal structure of 2,6-dibromo-4-fluoroaniline, C6H4Br2FN
  61. The crystal structure of 4-chloro-N-(2-phenoxyphenyl)benzamide, C19H14ClNO2
  62. The crystal structure of 2-methyl-β-naphthothiazole, C12H9NS
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 17.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2020-0522/html?lang=en&srsltid=AfmBOooonFPz__lYF4EohmZgoLIDLskXR4C6aBZU3DknWEmYbr31MzRW
Scroll to top button