Home Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
Article Open Access

Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn

  • See Mun Lee , Kong Mun Lo and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 10, 2019
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 234 Issue 6

Abstract

C8H18ClNS2Sn, triclinic, P1̄ (no. 2), a = 6.4399(2) Å, b = 9.6430(3) Å, c = 11.6944(1) Å, α = 91.966(2)°, β = 101.821(2)°, γ = 105.391(3)°, V = 682.30(3) Å3, Z = 2, Rgt(F) = 0.0227, wRref(F2) = 0.0609, T = 100 K.

CCDC no.: 1946282

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 prism
Size:0.08 × 0.06 × 0.03 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:19.3 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:16394, 2444, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2399
N(param)refined:122
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.88424(2)0.71732(2)0.84888(2)0.01924(9)
Cl10.84361(11)0.93203(7)0.74494(6)0.03091(17)
S10.58280(10)0.57512(6)0.68894(5)0.02078(15)
S20.79477(11)0.43192(7)0.87990(6)0.02390(15)
N10.4509(4)0.2927(2)0.70830(19)0.0216(5)
C11.2139(5)0.7382(3)0.8331(3)0.0295(6)
H1A1.30270.83850.85590.044*
H1B1.21420.71120.75160.044*
H1C1.27670.67440.88450.044*
C20.7909(5)0.7750(3)1.0032(3)0.0307(6)
H2A0.92260.80931.06700.046*
H2B0.68890.69051.02510.046*
H2C0.71790.85200.98890.046*
C30.5936(4)0.4163(3)0.7553(2)0.0200(5)
C40.4537(5)0.1557(3)0.7590(3)0.0272(6)
H4A0.53280.10460.71720.041*
H4B0.30170.09580.75140.041*
H4C0.52840.17550.84210.041*
C50.2719(5)0.2839(3)0.6031(2)0.0253(6)
H5A0.22940.18650.56050.030*
H5B0.32730.35530.54980.030*
C60.0692(5)0.3131(3)0.6362(3)0.0268(6)
H6A0.11260.41060.67870.032*
H6B0.01550.24210.69010.032*
C7−0.1193(5)0.3043(3)0.5298(3)0.0294(6)
H7A−0.23060.34490.55480.035*
H7B−0.06000.36450.47060.035*
C8−0.2318(5)0.1516(3)0.4733(3)0.0344(7)
H8A−0.12940.11630.43650.052*
H8B−0.36320.15120.41350.052*
H8C−0.27550.08860.53330.052*

Source of material

All chemicals and solvents were used as purchased without purification. The melting point was determined using a Mel-temp II digital melting point apparatus and was uncorrected. The solid-state IR spectrum was obtained on a Bruker Vertex 70v FTIR Spectrometer from 4000 to 400 cm−1. The 1H and 13C{1H} NMR spectra were recorded at room temperature in CDCl3 solution on a Bruker Ascend 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

The dithiocarbamate ligand was prepared in situ (acetone) from the reaction of CS2 (Merck 0.25 mmol) with n-butylmethylamine (Merck, 0.25 mmol) and NaOH (0.02 mL; 50% w/v); CS2 was added dropwise into the acetone solution (10 mL). The resulting mixture was kept at 273 K for 0.5 h. Dimethyltin dichloride (Merck, 0.25 mmol, 0.05 g) in acetone (10 mL) was added to the prepared sodium n-butyl(methyl)dithiocarbamate. The resulting mixture was stirred and refluxed for 2 h. The filtrate was evaporated slowly until a white precipitate was formed. The precipitate was recrystallized from acetone-methanol by slow evaporation to yield colourless crystals. Yield: 0.042 g (48.5%). M.pt: 369–370 K. IR (cm−1) 1466 (m) ν(CN), 1071 (s) ν(CS), 749 (m) ν(CS), 553 (m) ν(SnS). 1H NMR (CDCl3, ppm): 0.97 (6H, 2J(119Sn1H) = 74 Hz, CH3), 1.19 (3H, CH3) 1.28–1.73 (m, 4H, CH2CH2), 3.35 (3H, N—CH3), 3.70–3.74 (m, 2H, N—CH2). 13C{1H} NMR (CDCl3, ppm): 9.9 (6H, 2J(119Sn13C) = 548 Hz, CH3), 13.7 (Bu—CH3), 19.9, 28.8 (Bu—CH2), 42.8 (NCH2), 58.0 (NCH3), 197.8 (CS2).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.98–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Comment

The crystal structure determination was reported recently for the methyl ester of the dithiocarbamate ligand featured in the title compound, namely MeSC(=S)N(Me)n-Bu [5]. Herein, the isolation and crystallographic analysis of chlorido-dimethyl-tin(IV) ester of this dithiocarbamate ligand, Me2Sn[S2CN(Me)n-Bu]Cl, (I), is described in continuation of studies of related compounds [6]. Organotin compounds related to Me2Sn[S2CN(Me)n-Bu]Cl have been investigated for their biological potential pharmaceutical applications [7] as well as for their suitability as synthetic precursors for the generation of tin sulphide nanomaterials via chemical vapour deposition and related techniques [7], [8].

The molecular structure of (I) is shown in the figure (70% displacement ellipsoids). The tin atom exists within a C2ClS2 donor set defined by an asymmetrically coordinating dithiocarbamate ligand, the chloride atom and two methyl-carbon atoms. The Sn—S1 [2.4638(6) Å] and Sn—S2 [2.7111(7) Å] bond lengths differ by approximately 0.25 Å, and consistent with this asymmetry is the systematic variation in the C3—S1, S2 bonds. Thus, the less tightly bound S2 atom forms a shorter C3—S2 bond [1.713(3) Å] than the more tightly bound S1 atom [1.751(3) Å], consistent with some double bond character in the former. The C3—S1, S2 bond lengths in (I) are intermediate between the formerly singly [1.7662(17) Å] and doubly [1.6590(18) Å] bonded distances in the MeSC(=S)N(Me)n-Bu ester [5]. The above variations in C—S bond lengths can also be compared with the experimental equivalence of the C—bonds, i.e. 1.7192(14) and C1—S2 = 1.7249(14) Å, in the recently determined salt of −S2CN(CH2CH2)2NPh [9]. A consistent feature in the organotin compound, (I), and in the cited ester [5] and salt [8] is the short C3—N bond, i.e. 1.317(4), 1.351(2) and 1.3419(18) Å, respectively, all indicative of significant double bond character in this bond and a major contribution of the 2−S2C= N+RR′ canonical form to the overall electronic structure of the respective dithiocarbamate chromophore. The C3S2 donor set defines a highly distorted geometry. This is quantified in the value of τ of 0.51 which is almost exactly intermediate between the values for ideal trigonal-bipyramidal [1.0] and square-pyramidal [0.0] [10].

The molecular packing is largely devoid of directional interactions between molecules. A weak secondary Sn⋯S contact of 3.9510(7) Å is noted to occur between the Sn and S2i atoms (symmetry operation (i) 2 − x, 1 − y, 2 − z) which is marginally less than the sum of the van der Waals radii for these atoms of 3.97 Å [11]. Secondary bonding interactions are important in dithiocarbamate compounds, including organotin dithiocarbamate compounds [12], [13], [14]. In the present case, the Sn⋯S interactions lead to a supramolecular dimer. The dimers are linked into a linear supramolecular chain along the b-axis direction by methyl-C—H⋯Cl interactions [C4—H4a⋯Clii: H4a⋯Clii = 2.90 Å, C4—H4a⋯Clii = 3.742(4) Å with angle at H4a = 144° for (ii) x, −1 + y, z].

Finally, the calculated Hirshfeld surfaces as well as the two-dimensional fingerprint plots (full and delineated into individual contacts) were evaluated for the most significant percentage contributors to the surface. This was accomplished using literature protocols [15] and Crystal Explorer 17 [16]. Given the lack of directional interactions in the crystal, it is not surprising that the most significant contributions to the surface are from H⋯H contacts, at 64.3%. The next three contacts, i.e. Cl⋯H/H⋯Cl [15.7%], S⋯H/H⋯S [15.2%] and C⋯H/H⋯C [2.6%], account for the bulk of the remaining contacts on the calculated Hirshfeld surface.

Acknowledgements

Sunway University Sdn Bhd is thanked for financial support of this work through Grant No. STR-RCTR-RCCM-001–2019.

References

1. Rigaku Oxford Diffraction: CrysAlisPRO. Rigaku Corporation, Oxford, UK (2018).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar

4. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Search in Google Scholar

5. Lo, K. M.; Lee, S. M.; Tiekink, E. R. T.: Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2. Z. Kristallogr. NCS 234 (2019). doi: 10.1515/ncrs-2019-0511.Search in Google Scholar

6. Lo, K. M.; Lee, S. M.; Tiekink, E. R. T.: Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-S,S)tin(IV), C13H19ClN2S2Sn. Z. Kristallogr. NCS 234 (2019) NCRS-2019-0501.10.1515/ncrs-2019-0501Search in Google Scholar

7. Tiekink, E. R. T.: Tin dithiocarbamates: applications and structures. Appl. Organomet. Chem. 22 (2008) 533–550.10.1002/aoc.1441Search in Google Scholar

8. Kana, A. T.; Hibbert, T. G.; Mahon, M. F.; Molloy, K. C.; Parkin, I. P.; Price, L. S.: Organotin unsymmetric dithiocarbamates: synthesis, formation and characterisation of tin(II) sulfide films by atmospheric pressure chemical vapour deposition. Polyhedron 20 (2001) 2989–2995.10.1016/S0277-5387(01)00908-1Search in Google Scholar

9. Lo, K. M.; Lee, S. M.; Tiekink, E. R. T.: Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]. Z. Kristallogr. NCS 234 (2019). doi: 10.1515/ncrs-2019-0512.Search in Google Scholar

10. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C.: Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]- copper(II) perchlorate. J. Chem. Soc. Dalton Trans. (1984) 1349–1356.10.1039/DT9840001349Search in Google Scholar

11. Spek, A. L.: Structure validation in chemical crystallography. Acta Crystallogr. D65 (2009) 148–155.10.1107/S090744490804362XSearch in Google Scholar PubMed PubMed Central

12. Tiekink, E. R. T.: Supramolecular assembly based on “emerging” intermolecular interactions of particular interest to coordination chemists. Coord. Chem. Rev. 345 (2017) 209–228.10.1016/j.ccr.2017.01.009Search in Google Scholar

13. Tiekink, E. R. T.: Exploring the topological landscape exhibited by binary zinc-triad 1,1-dithiolates. Crystals 8 (2018) 292.10.3390/cryst8070292Search in Google Scholar

14. Zaldi, N. B.; Hussen, R. S. D.; Lee, S. M.; Halcovitch, N. R.; Jotani, M. M.; Tiekink, E. R. T.: Secondary bonding in dimethylbis(morpholine-4-carbodithioato-κ2S,S′)tin(IV): crystal structure and Hirshfeld surface analysis. Acta Crystallogr. E73 (2017) 842–848.10.1107/S2056989017006855Search in Google Scholar PubMed PubMed Central

15. Tan, S. L.; Jotani, M. M.; Tiekink, E. R. T.: Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing. Acta Crystallogr. E75 (2019) 308–318.10.1107/S2056989019001129Search in Google Scholar PubMed PubMed Central

16. Turner, M. J.; Mckinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A.: Crystal Explorer v17. The University of Western Australia, Australia (2017).Search in Google Scholar

Received: 2019-07-17
Accepted: 2019-08-15
Published Online: 2019-09-10
Published in Print: 2019-11-26

©2019 See Mun Lee et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0502
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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 22.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2019-0502/html
Scroll to top button