Home Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
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Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn

  • Kong Mun Lo , See Mun Lee and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 9, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 6

Abstract

C13H19ClN2S2Sn, triclinic, P1̄ (no. 2), a = 6.5837(2) Å, b = 9.9458(2) Å, c = 12.8720(3) Å, α = 85.344(2)°, β = 79.508(2)°, γ = 83.832(2)°, V = 822.33(4) Å3, Z = 2, Rgt(F) = 0.0176, wRref(F2) = 0.0461, T = 100 K.

CCDC no.: 1946283

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:0.13 × 0.04 × 0.03 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:16.1 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:19541, 2930, 0.036
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2870
N(param)refined:174
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.48439(2)0.81316(2)0.39082(2)0.01348(6)
S10.30756(7)0.60263(5)0.42166(4)0.01538(11)
S20.58283(7)0.65990(5)0.21741(4)0.01759(11)
Cl10.34240(8)0.85991(5)0.57712(4)0.02212(12)
N10.3630(3)0.44530(17)0.25898(14)0.0163(4)
N20.1508(2)0.27759(17)0.15351(14)0.0148(3)
C10.3015(3)0.9652(2)0.31460(18)0.0197(4)
H1A0.39011.03310.27680.030*
H1B0.19411.00880.36760.030*
H1C0.23590.92400.26410.030*
C20.8031(3)0.7907(2)0.40266(18)0.0222(5)
H2A0.88520.82100.33510.033*
H2B0.84600.69520.41960.033*
H2C0.82560.84540.45880.033*
C30.4135(3)0.5569(2)0.29355(17)0.0149(4)
C40.2111(3)0.3575(2)0.32026(17)0.0194(4)
H4A0.14150.40070.38570.023*
H4B0.28320.26950.34080.023*
C50.0505(3)0.3345(2)0.25377(17)0.0181(4)
H5A−0.04690.27170.29370.022*
H5B−0.03020.42170.23910.022*
C60.2938(3)0.3696(2)0.09272(17)0.0167(4)
H6A0.21640.45720.07600.020*
H6B0.36060.33030.02520.020*
C70.4592(3)0.3926(2)0.15655(18)0.0196(4)
H7A0.54390.30610.16820.023*
H7B0.55230.45790.11640.023*
C80.0112(3)0.2269(2)0.09669(17)0.0153(4)
C9−0.1010(3)0.1189(2)0.14391(17)0.0174(4)
H9−0.08520.08270.21290.021*
C10−0.2348(3)0.0646(2)0.09047(19)0.0212(5)
H10−0.3096−0.00870.12310.025*
C11−0.2603(3)0.1165(2)−0.01024(18)0.0225(5)
H11−0.35280.0794−0.04640.027*
C12−0.1495(3)0.2228(2)−0.05748(18)0.0216(5)
H12−0.16600.2586−0.12650.026*
C13−0.0139(3)0.2779(2)−0.00447(17)0.0180(4)
H130.06170.3506−0.03770.022*

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 (methanol) from the reaction of CS2 (Merck 0.25 mmol) with 1-phenylpiperazine (Merck, 0.25 mmol) and NaOH (0.02 mL; 50% w/v); CS2 was added dropwise into the methanolic solution (10 mL). The resulting mixture solution was kept at 273 K for 0.5 h. Dimethyltin dichloride (Merck, 0.25 mmol, 0.05 g) in methanol (10 mL) was added to the prepared sodium 1-phenylpiperazinedithiocarbamate. The resulting mixture was stirred under reflux for 2 h. The filtrate was evaporated slowly until a white precipitate was formed. The precipitate was recrystallized from methanol by slow evaporation to yield colourless crystals.

Yield: 0.052 g (49.3%). M.pt: 479–480 K. IR (cm−1) 1598 (m) ν(CN), 1216 (m) ν(CS), 1012 (s) ν(CN), 558 (m) ν(SnS). 1H NMR (CDCl3, ppm): 1.39 (6H, Sn—CH3), 3.21–3.25 (m, 4H, N—CH2), 4.17–4.22 (m, 4H, N—CH2), 6.83–7.23 (m, 5H, Ph—H). 13C NMR (CDCl3, ppm): 15.6 (Sn—CH3), 48.9, 50.9 (piperazine-C), 118.1, 125.5, 130.8, 150.4 (Ph—C), 199.9 (CS2).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C).

Comment

Recently, the structure of the dithiocarbamate ligand featured in the title compound, Me2Sn[S2CN(CH2CH2)2NPh]Cl, became available in its salt with the 4-phenylpiperazin-1-ium cation [5]. Organotin dithiocarbamate compounds are well-known as potential pharmaceuticals and as having applications as synthetic precursors for the chemical vapour deposition of tin sulphide nanomaterials [6]. It was biological considerations [7] that led to the formation and crystallographic analysis of the title compound.

The molecular structure of Me2Sn[S2CN(CH2CH2)2NPh]Cl is shown in the figure (70% displacement ellipsoids) and comprises a penta-coordinate tin atom. The dithiocarbamate ligand is asymmetrically chelating the tin centre, forming Sn—S1, S2 bond lengths of 2.4734(5) and 2.7458(5) Å, respectively. The longer Sn—S2 bond is partly due to the approximately trans disposition of the S2 atom to the chloride, i.e. S2—Sn—Cl1 = 155.971(16)°. The difference in the Sn—S separations, i.e. Δ(Sn—S) = [(Sn—Slong) – (Sn—Sshort)] = 0.27 Å, results in a disparity in the associated C—S bond lengths. Thus, the C3—S1 bond length [1.746(2) Å] associated with the more tightly bound sulphur atom is longer than the equivalent bond [1.714(2) Å] involving the less tightly bound S2 atom. This contrasts the situation in the structure of the salt of the dithiocarbamate anion [5] whereby the C1—S1, S2 bond lengths of 1.7192(14) and 1.7249(14) Å, respectively, are experimentally equivalent. The Sn—Cl1 bond length is 2.4722(5) Å. A quantitative measure of a five-coordinate geometry is τ, which ranges from 0.0 to 1.0 for ideal square-pyramidal and trigonal-bipyramidal coordination geometries, respectively [8]. The value of τ computes to 0.40 in the title compound, indicating a highly distorted geometry. The distortion is ascribed in part to the acute chelate S1—Sn—S2 angle of 68.887(16)° as well as the wide angle subtended by the tin-bound methyl groups, with C1—Sn—C2 = 132.18(9)°. In summary, the structure of Me2Sn[S2CN(CH2CH2)2NPh]Cl conforms to the expected motif for compounds of this type [6], [9], [10].

There are several non-covalent interactions less than the sum of the respective van der Waals radii in the molecular packing. Thus, methylene-C—H⋯Cl interactions lead to the formation of centrosymmetric dimeric aggregates [C5—H5a⋯Cl1i: H5a⋯Cl1i = 2.70 Å, C5⋯Cl1i = 3.676(2) Å with angle at H5a = 170° for symmetry operation (i) −x, 1 − y, 1 − z]. These aggregates are connected into a supramolecular layer with a flat topology and parallel to (0 1 −1). The layer is sustained by C—H⋯π(phenyl) and π—π stacking interactions involving the same phenyl ring [C7—H7a⋯Cg(C8—C13)ii: H7a⋯Cg(C8—C13)ii = 2.76 Å, C7⋯Cg(C8—C13)ii = 3.500(2) Å with angle at H7a = 132° and Cg(C8—C13)⋯Cg(C8—C13)iii = 3.7795(12) Å for (ii) 1 + x, y, z and (iii) −x, −y, −z]. Weak phenyl-C—H⋯S(thione) interactions [C13—H13⋯S2iv: H13⋯S2iv = 2.98 Å, C13⋯S2iv = 2.9774(19) Å with angle at H13 = 128° for (iv) 1 − x, 1 − y, −z] feature in the inter-layer region.

In order to analyse the molecular further, the Hirshfeld surfaces were calculated along with the full and delineated two-dimensional fingerprint plots using Crystal Explorer [11] and established protocols [12]. The aforementioned phenyl-C—H⋯S(thione) interaction is the only one less than the sum of the van der Waals radii of sulphur and hydrogen in the crystal, with other H⋯S contacts occurring at longer distances. Overall, S⋯H/H⋯S contacts contribute 13.3% of all contacts on the calculated Hirshfeld. Other significant surface contacts are of the type Cl⋯H/H⋯Cl (13.2%) and C⋯H/H⋯C (11.1%). However, none of these compare in significance to H⋯H contacts, with these making the greatest percentage contribution of 56.4% of all contacts.

Funding source: Sunway University Sdn Bhd

Award Identifier / Grant number: STR-RCTR-RCCM-001–2019

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

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

©2019 Kong Mun Lo et al., published by De Gruyter, Berlin/Boston

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

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  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-2019-0501
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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
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