Home Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
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Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2

  • Peter J. Heard , Nathan R. Halcovitch , Lee See Mun and Edward R.T. Tiekink EMAIL logo
Published/Copyright: March 16, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 3

Abstract

C24H36N2O6Re2, triclinic, P1̅ (no. 2), a = 10.3013(2) Å, b = 11.3471(2) Å, c = 14.5967(3) Å, α = 72.540(2)°, β = 73.074(2)°, γ = 85.369(2)°, V = 1557.05(6) Å3, Z = 2, Rgt(F) = 0.0214, wRref(F2) = 0.0466, T = 100(2) K.

CCDC no.: 1825597

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:Cube, colourless
Size:0.08 × 0.06 × 0.06 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:8.07 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:28.7°, > 88% (up to 25.2°, > 99%)
N(hkl)measured, N(hkl)unique, Rint:30121, 7111, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6456
N(param)refined:347
Programs:CrysAlisPRO [1], SHELX [2, 3], WinGX and ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Re10.40511(2)0.27796(2)0.19086(2)0.01285(4)
Re20.39780(2)0.24905(2)0.45674(2)0.01121(4)
S10.48696(9)0.49522(8)0.14289(6)0.01645(17)
S20.28273(8)0.37480(8)0.32572(6)0.01362(16)
S30.59125(9)0.39904(8)0.38438(6)0.01580(17)
S40.55783(8)0.19842(8)0.30727(6)0.01288(16)
O10.2678(3)0.0216(3)0.2747(2)0.0311(7)
O20.6050(3)0.1905(3)0.02274(19)0.0258(6)
O30.1977(3)0.3460(3)0.0705(2)0.0265(6)
O40.1866(3)0.0414(3)0.5203(2)0.0265(6)
O50.5463(3)0.0839(2)0.60121(19)0.0242(6)
O60.2157(3)0.3495(2)0.62371(18)0.0203(5)
N10.3637(3)0.6121(3)0.2807(2)0.0149(6)
N20.7855(3)0.3384(3)0.2362(2)0.0138(6)
C10.3792(3)0.5105(3)0.2529(2)0.0142(7)
C20.4341(4)0.7281(3)0.2146(3)0.0180(7)
H2A0.37550.79910.22530.022*
H2B0.45130.72960.14390.022*
C30.5676(4)0.7403(3)0.2353(3)0.0201(8)
H3A0.62900.67350.21840.024*
H3B0.55090.72990.30760.024*
C40.6373(4)0.8657(4)0.1751(3)0.0244(8)
H4A0.57520.93220.19190.029*
H4B0.71960.87110.19570.029*
C50.6775(4)0.8877(4)0.0623(3)0.0284(9)
H5A0.72930.81690.04570.043*
H5B0.73350.96270.02920.043*
H5C0.59570.89770.03950.043*
C60.2783(4)0.6156(3)0.3802(3)0.0177(7)
H6A0.32190.67020.40440.021*
H6B0.27270.53150.42740.021*
C70.1358(4)0.6614(4)0.3803(3)0.0213(8)
H7A0.09000.60480.35930.026*
H7B0.14080.74420.33140.026*
C80.0520(4)0.6689(4)0.4840(3)0.0251(8)
H8A−0.04440.68050.48460.030*
H8B0.05910.58910.53400.030*
C90.0947(4)0.7720(4)0.5159(3)0.0291(9)
H9A0.18580.75540.52470.044*
H9B0.03050.77640.57920.044*
H9C0.09530.85080.46420.044*
C100.6625(4)0.3201(3)0.2991(2)0.0157(7)
C110.8397(4)0.2618(3)0.1682(3)0.0171(7)
H11A0.90880.31020.10860.021*
H11B0.76530.24130.14520.021*
C120.9036(4)0.1423(4)0.2168(3)0.0230(8)
H12A0.83500.09290.27610.028*
H12B0.97880.16190.23940.028*
C130.9577(4)0.0672(4)0.1425(3)0.0296(9)
H13A0.88350.05380.11620.036*
H13B1.03010.11540.08540.036*
C141.0137(5)−0.0562(4)0.1881(4)0.0402(12)
H14A1.0891−0.04360.21250.060*
H14B1.0463−0.10030.13740.060*
H14C0.9422−0.10500.24400.060*
C150.8773(4)0.4344(3)0.2320(3)0.0190(8)
H15A0.96810.39860.23240.023*
H15B0.84190.46400.29190.023*
C160.8899(4)0.5430(3)0.1379(3)0.0203(8)
H16A0.93370.51440.07840.024*
H16B0.79790.57230.13410.024*
C170.9720(4)0.6503(4)0.1355(3)0.0239(8)
H17A0.96510.72190.07830.029*
H17B0.93190.67450.19760.029*
C181.1196(4)0.6209(4)0.1263(3)0.0282(9)
H18A1.12790.55540.18580.042*
H18B1.16770.69500.12040.042*
H18C1.15930.59310.06670.042*
C190.3210(4)0.1160(4)0.2455(3)0.0206(8)
C200.5285(4)0.2235(3)0.0854(3)0.0193(8)
C210.2773(4)0.3225(3)0.1153(3)0.0195(8)
C220.2655(4)0.1196(3)0.4947(3)0.0179(7)
C230.4894(4)0.1455(3)0.5475(2)0.0152(7)
C240.2852(3)0.3126(3)0.5615(2)0.0143(7)

Source of materials

Bromopentacarbonylrhenium was prepared from a 1:1 molar ratio of Re2(CO)10 (Alfa Aesar) and Br2 (Panreac) in dichloromethane at 0°. White solids were obtained from the slow evaporation of the solvent. The solids were recrystallized in acetone before use. The dithiocarbamate ligand was prepared in situ (acetone) from the reaction of CS2 (Panreac 0.25 mmol) with di-n-butylamine (Merck, 0.25 mmol) and NaOH (0.02 mL; 50% w/v); CS2 was added dropwise into the acetone solution (15 mL). The resulting mixture solution was kept at 273 K for 0.5 h. Bromopentacarbonylrhenium(I) (0.25 mmol) in acetone (10 mL) was added into the solution and the resulting mixture was stirred for 2.5 h. The filtrate was evaporated until a precipitate was obtained. The precipitate was washed with n-hexane and recrystallised from its dichloromethane solution. Colourless blocks were obtained from the slow evaporation of the solvent. Yield: 61%. M.p: 450 K. IR (KBr, cm−1): 2031 (s), 2012 (s), 1888 (vs). 1H NMR (CDCl3): 0.96–1.04 (m, 6H, CH3), 1.33–1.49 (m, 4H, CH2—CH3), 1.66–1.89 (m, 4H, −CH2−CH2N), 3.68–3.82 (m, 4H, NCH2−).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.98–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). Owing to poor agreement, the (6 3 3) reflection was omitted from the final cycles of refinement. The maximum and minimum residual electron density peaks of 1.57 and 1.06 e Å−3, respectively, were located 0.97 and 0.67 Å from the S3 and Re1 atoms.

Discussion

The biological efficacy of metal dithiocarbamates (−S2CNRR′) is well known and has been the subject of a review [5]. The heavy element, rhenium, continues to attract interest as both putative therapeutic agents as well as radiopharmaceuticals and dithiocarbamates feature in these investigations [6], [7], [8]. In continuation of studies into the biological efficacy of heavy metal dithiocarbamate compounds as anti-cancer, e.g. bismuth [9], and anti-microbial, e.g. gold [10], agents, attention has been directed towards rhenium and it was in this context that the title complex was studied.

The binuclear complex of {Re[S2CN(n-Bu)2](CO)3}2 is shown in the figure (50% displacement ellipsoids) and features two μ2-bridging dithiocarbamate ligands, each chelating one rhenium(I) atom and simultaneously bonding to the other via one sulphur atom. The Re—S bond lengths formed by the chelating ligands span the narrow range 2.4953(9) to 2.5125(8) Å and the bridging Re—S bond lengths are considerably longer at 2.5659(8) Å (Re1—S4) and 2.5511(8) Å (Re2—S2). This disparity in Re—S bond lengths implies the central Re2S2 core approximates a rectangle. Each rhenium atom is also coordinated by three terminally bound carbonyl groups which occupy facial positions in the approximately octahedral C3S3 donor set. Globally, the dithiocarbamate ligands are syn, lying to the same side of the central Re2S2 core.

The structure resembles closely that reported for the diethyldithiocarbamate analogue [11], i.e. with a syn-disposition of dithiocarbamate ligands and fac-C3S3 coordination geometries. The main difference relates to the latter conforming to crystallographic 2-fold symmetry; the Re—S (chelating) bond lengths are 2.4813(15) and 2.5050(15) Å and the bridging distance is 2.5475(15) Å.

Acknowledgements

Sunway University is thanked for support of biological and crystal engineering studies of metal dithiocarbamates.

References

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Received: 2017-11-27
Accepted: 2018-2-24
Published Online: 2018-3-16
Published in Print: 2018-5-24

©2018 Peter J. Heard et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
https://doi.org/10.1515/ncrs-2017-0370
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14
  3. Crystal structure of 4-methoxy-6-phenyl-2H-pyran-2-one, C12H10O3
  4. Crystal structure of tris{(3-((E)-(((E)-2-oxidobenzylidene)hydrazono)methyl)-2-oxo-2H-chromen-4-olato-κ3O,N:N′)}dicobalt(III)tris(dimethylformamide), C60H50Co2N9O15
  5. Crystal structure of poly[bis(1-methyl-[4,4′-bipyridin]-1-ium-κN)-tetrakis(μ3-sulfato-κ3O:O′:O′′)trizinc(II)], C22H22Zn3N4O16S4
  6. Crystal structure of (5Z,10Z)-3,13-dichloro-17,18-dioxo-5,11-diphenyl-8,9,17,18-tetrahydro-7H-dibenzo[e,n][1,4,8,12]tetraazacyclopentadecine-16,19-diido-κ4N,N′,N′′,N′′′)copper(II), C31H22N4O2Cl2Cu
  7. Crystal structure of bis{5-methoxy-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2N,O}zinc(II), C34H24N2O8Zn
  8. Crystal structure of 2,2′-((((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenolato-κ2N;κ4O)nickel(II), C28H22N2O4Ni
  9. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato)cobalt(II), C36H26N2O4Co
  10. Crystal structure of camptothecin, C20H16N2O4
  11. Crystal structure of (2-(chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato–κ2O,O′)(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, Ni(C16H36N4)(C12H12O4Cl)ClO4⋅H2O
  12. Crystal structure of 3-(2-chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (C19H13ClN2O2)
  13. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis{[(E)-2,6-diisopropyl-N-(pyridin-3-ylmethylene)aniline]copper (II)}, C44H56Cu2N4O8
  14. Crystal structure of diethyl 2-(2-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19Cl1O6
  15. Crystal structure of (μ2-2,2′-bipyridine-3,3′-dicarboxylato)-bis(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)-di-nickel(II) perchlorate N,N′-dimethylformamide solvate, C50H92Cl2N12Ni2O14
  16. Crystal structure of catena-poly[triaqua(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)-(1,2-bis(4-pyridyl)ethane-κN)nickel(II)] 2-aminonicotinate nitrate – 1,2-bis(4-pyridyl)ethane – water (2/1/8), C36H44N8NiO12
  17. Hydrothermal synthesis and crystal structure of poly[bis(μ2-3-(3,5-dicarboxyphenoxy)phthalato-κ3O,O′:O′′)-(μ2-1,2-di(pyridin-4-yl)ethane-κ2N:N′)copper(II)], C22H14CuNO9
  18. Crystal structure of catena-poly[aqua-(methanol-κO)-bis(μ2-4-(pyridin-4-yl)benzoato-κ2N:O)-bis(triphenylphospine-κP)disilver(I)], C61H52Ag2N2O6P2
  19. The crystal structure of 6-(4-bromobenzyl)-1,3,5-trimethyl-7-phenyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione, C22H20BrN3O2
  20. Synthesis and crystal structure of catena-poly[bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κO;κ2O′,O′′)-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)zinc(II)], C44H32N4ZnCl4O4
  21. Crystal structure of diaqua-bis[N-phenyl-2-(quinolin-8-yloxy)acetamide-κ3-N,O,O′]-nitrato(κ2O,O′)-cerium(III) dinitrate - acetone (1/2), C40H44N7O17Ce
  22. Crystal structure of the 2D coordination polymer poly[aqua(μ2-2,2′-(1,2-phenylene)diacetato-κ3O,O′:O′)-(μ2-4,4′-bis((1H-1,2,4-triazol-1-yl)methyl)-1,1′-biphenyl-κ2N:N′)cobalt(II)], C28H26CoN6O5
  23. Crystal structure of (dimethylformamide-κO)(perchlorato-κ2O,O′){μ2-6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-methoxyphenolate)-κ8N,N′,O:O,O′:O′,O′′,O′′′}sodium(I)nickel(II), C25H23Br2ClN3NaNiO9
  24. The crystal structure of catena-poly[bis((4-aminophenyl)sulfonyl)(pyrimidin-2-yl)amido-κ2N,N′)-bis(μ2-4,4′-bipyridine-N,N′-κ2N:N′)zinc(II) – methanol (1/2), C32H34N10O6S2Zn
  25. Synthesis and crystal structure poly[aqua(μ3-2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetate-κ4O,O′:O′′:O′′′) sodium] monohydrate, C18H18NNaO11S
  26. Crystal structure of methyl 4′-amino-3′,5′-diisopropyl-[1,1′-biphenyl]-4-carboxylate, C20H25NO2
  27. Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru
  28. Crystal structure of 2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione, C14H15Cl2N3OS
  29. Crystal structure of methyl 4′-amino-3′,5′-dimethyl-[1,1′-biphenyl]-4-carboxylate, C16H17NO2
  30. The crystal structure of 1-(5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pentan-1-on, C19H19F3FeN2O
  31. The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C34H56O6
  32. Crystal structure of methyl 10-(pyridin-4-yl)-anthracene-9-carboxylate, C21H15NO2
  33. Crystal structure of catena-poly[diaqua-bis(di(N2,N6-dihydroxypyridine-2,6-dicarboxamide))potassium(I)]tetrahydrate, C14H25N6O14K
  34. Crystal structure of poly{[μ2-(E)-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′][μ3–cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′:O′′′]cadmium(II)}, C26H26CdN4O4
  35. Crystal structure of poly[aqua(μ3-[2,2′-bipyridine]-3,3′-dicarboxylato-κ4N,N′:O:O′)zinc(II)] – dimethylformamide (1/1), C15H15N3O6Zn
  36. The crystal structure of poly[tetraaqua-tris(μ2-2,6-di(1H-imidazol-1-yl)naphthalene-κ2N:N′)-bis(thiophene-2,5-dicarboxylato-κ1O)]dicobalt(II), C30H24CoN6O6S
  37. Crystal structure of (S)-1-(5-(anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O
  38. Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
  39. Synthesis and crystal structure of μ-[1,1′-di(mesitylphosphanido)ferrocene]bis[η5-cyclopentadienylnickel(II)] tetrahydrofurane solvate, C42H48FeNi2OP2
  40. Synthesis and crystal structure of (E)-1-(4-(((E)-5-chloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15ClN2O2
  41. Crystal structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)nickel(II), C24H22N8O4S2Ni
  42. Crystal Structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)copper(II), C24H22N8O4S2Cu
  43. Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O,O′:O′′:O′′′}sodium(I)] monohydrate, C21H22NNaO11S
  44. Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
  45. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ2S:S′) bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dizinc(II), C28H56N4S8Zn2
  46. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ3S,S′:S)bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dicadmium(II), C28H56Cd2N4S8
  47. Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
  48. Crystal structure of 7-(4-methylphenyl)imidazo[1,2-a][1,3,5]triazin-4-amine, C12H11N5
  49. Crystal structure of the co-crystal O-isopropyl phenylcarbamothioate – 4,4′-bipyridine (2/1), C15H17N2OS
  50. Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
  51. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-di(ethanol)-bis{μ2-5-(N,N′-diethylamine)-5′-methoxyl-2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato-κ6O:O,N,N,O′:O′}trinickel(II) – ethanol – acetonitrile (1/2/2), C58H86Ni3N8O18
  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
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