Home Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
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Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4

  • Yi Jiun Tan , Chien Ing Yeo , Nathan R. Halcovitch and Edward R.T. Tiekink EMAIL logo
Published/Copyright: March 30, 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

C46H82Cu2N2P2S4, triclinic, P1̄ (no. 2), a = 11.6189(2) Å, b = 12.2846(2) Å, c = 18.1744(2) Å, α = 97.3210(10)°, β = 106.3080(10)°, γ = 99.312(2)°, V = 2415.65(7) Å3, Z = 2, Rgt(F) = 0.025, wRref(F2) = 0.066, T = 100(2) K.

CCDC no.:: 1830644

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless prism
Size:0.23 × 0.13 × 0.06 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:35.7 cm−1
Diffractometer, scan mode:SuperNova Dual, ω scans
2θmax, completeness:153.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:40039, 10075, 0.025
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 9554
N(param)refined:505
Programs:Rigaku programs [1], SHELX [2, 3], ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cu10.37887(2)0.67751(2)0.19565(2)0.01476(5)
Cu20.25867(2)0.50466(2)0.27472(2)0.01404(5)
S10.16191(3)0.60450(2)0.17490(2)0.01315(6)
S20.30616(3)0.56556(3)0.06661(2)0.01568(7)
S30.47423(3)0.56008(2)0.27617(2)0.01313(6)
S40.29599(3)0.34516(2)0.20530(2)0.01375(6)
P10.48033(3)0.85298(2)0.22485(2)0.01118(6)
P20.17179(3)0.51897(3)0.36781(2)0.01129(6)
N10.09549(10)0.43162(9)0.05676(6)0.0144(2)
N20.50598(10)0.39946(9)0.17479(6)0.0148(2)
C10.17887(11)0.52350(11)0.09394(7)0.0132(2)
C2−0.00783(12)0.38684(12)0.08375(8)0.0182(3)
H2A−0.06680.43730.07910.022*
H2B0.02150.37730.13870.022*
C3−0.06624(15)0.27407(13)0.02981(10)0.0312(3)
H3A−0.09650.21820.05840.037*
H3B−0.13560.2813−0.01430.037*
C40.03500(16)0.23996(13)0.00122(10)0.0315(3)
H4A0.00100.1895−0.05020.038*
H4B0.08550.20130.03860.038*
C50.11010(13)0.34977(11)−0.00479(7)0.0183(3)
H5A0.19730.34550.00470.022*
H5B0.07810.3696−0.05680.022*
C60.43209(11)0.43076(10)0.21358(7)0.0129(2)
C70.47548(13)0.29293(11)0.11917(8)0.0192(3)
H7A0.39030.27930.08400.023*
H7B0.48550.22900.14680.023*
C80.56748(14)0.31027(14)0.07400(9)0.0261(3)
H8A0.53480.34400.02780.031*
H8B0.58870.23850.05680.031*
C90.67864(13)0.39053(14)0.13335(9)0.0254(3)
H9A0.72770.34990.17000.031*
H9B0.73170.43090.10710.031*
C100.62090(12)0.47072(12)0.17522(8)0.0201(3)
H10A0.67440.50200.22920.024*
H10B0.60460.53320.14710.024*
C110.59368(11)0.89390(10)0.32407(7)0.0136(2)
H110.66250.85520.32240.016*
C120.65160(12)1.01932(11)0.35035(7)0.0174(3)
H12A0.58661.06190.35180.021*
H12B0.69071.04500.31200.021*
C130.74775(13)1.04398(12)0.43117(8)0.0207(3)
H13A0.81751.00850.42850.025*
H13B0.77921.12600.44750.025*
C140.69306(14)0.99941(12)0.49135(8)0.0220(3)
H14A0.75771.01270.54230.026*
H14B0.62861.04010.49780.026*
C150.63808(14)0.87402(12)0.46555(8)0.0229(3)
H15A0.60070.84720.50440.027*
H15B0.70410.83300.46340.027*
C160.54075(13)0.84839(11)0.38558(7)0.0174(3)
H16A0.47070.88300.38890.021*
H16B0.51020.76620.36950.021*
C210.38760(11)0.96245(10)0.21276(7)0.0131(2)
H210.44291.03600.21730.016*
C220.29320(12)0.93166(11)0.13062(7)0.0165(2)
H22A0.33680.92700.09110.020*
H22B0.24090.85700.12480.020*
C230.21251(12)1.01827(12)0.11629(8)0.0186(3)
H23A0.26371.09120.11670.022*
H23B0.15040.99390.06420.022*
C240.14789(13)1.03312(12)0.17832(9)0.0214(3)
H24A0.08840.96310.17340.026*
H24B0.10201.09410.16990.026*
C250.24021(13)1.06150(12)0.25999(8)0.0193(3)
H25A0.19581.06540.29910.023*
H25B0.29331.13610.26690.023*
C260.31997(12)0.97402(11)0.27392(7)0.0164(2)
H26A0.26780.90060.27150.020*
H26B0.38050.99640.32660.020*
C310.57032(12)0.87303(11)0.15526(7)0.0148(2)
H310.51600.82830.10380.018*
C320.68220(13)0.81816(13)0.17662(8)0.0205(3)
H32A0.74160.86100.22630.025*
H32B0.65580.74080.18430.025*
C330.74462(15)0.81468(16)0.11279(9)0.0302(3)
H33A0.81880.78280.12950.036*
H33B0.68810.76530.06460.036*
C340.78059(15)0.93146(17)0.09595(9)0.0323(4)
H34A0.84470.97820.14230.039*
H34B0.81520.92600.05200.039*
C350.67074(14)0.98739(14)0.07558(9)0.0256(3)
H35A0.61070.94530.02590.031*
H35B0.69811.06470.06820.031*
C360.60842(13)0.99142(12)0.13981(8)0.0198(3)
H36A0.66571.03960.18830.024*
H36B0.53511.02460.12370.024*
C410.06916(11)0.38728(10)0.37059(7)0.0137(2)
H410.02340.40510.40820.016*
C420.14093(12)0.29734(11)0.39701(8)0.0186(3)
H42A0.19150.28300.36260.022*
H42B0.19670.32510.45080.022*
C430.05451(13)0.18733(12)0.39463(8)0.0214(3)
H43A0.10350.13030.40970.026*
H43B0.01000.20010.43300.026*
C44−0.03765(12)0.14318(11)0.31400(8)0.0188(3)
H44A−0.09490.07500.31550.023*
H44B0.00600.12250.27650.023*
C45−0.10956(13)0.23157(12)0.28721(9)0.0220(3)
H45A−0.16060.24570.32140.026*
H45B−0.16500.20330.23340.026*
C46−0.02392(13)0.34139(11)0.28948(8)0.0197(3)
H46A−0.07340.39800.27410.024*
H46B0.02070.32860.25110.024*
C510.27541(11)0.55784(11)0.46964(7)0.0132(2)
H510.30430.48770.48110.016*
C520.39300(12)0.64410(12)0.48048(8)0.0194(3)
H52A0.37280.71820.47380.023*
H52B0.43160.62090.44060.023*
C530.48258(13)0.65283(12)0.56233(8)0.0224(3)
H53A0.50810.58030.56710.027*
H53B0.55670.71090.56990.027*
C540.42394(14)0.68289(12)0.62543(8)0.0233(3)
H54A0.40480.75830.62360.028*
H54B0.48250.68520.67730.028*
C550.30678(13)0.59743(13)0.61404(8)0.0205(3)
H55A0.26850.62030.65420.025*
H55B0.32680.52320.62040.025*
C560.21629(12)0.58859(12)0.53288(7)0.0172(3)
H56A0.19090.66120.52810.021*
H56B0.14220.53060.52570.021*
C610.06681(11)0.61861(10)0.34756(7)0.0132(2)
H610.02180.59660.29050.016*
C620.14004(12)0.73865(10)0.35756(7)0.0146(2)
H62A0.18440.76770.41350.018*
H62B0.20140.73760.32930.018*
C630.05458(13)0.81620(11)0.32611(8)0.0179(3)
H63A0.10300.89340.33480.021*
H63B0.01540.79060.26930.021*
C64−0.04413(13)0.81669(12)0.36639(8)0.0192(3)
H64A−0.09990.86510.34380.023*
H64B−0.00530.84820.42260.023*
C65−0.11766(13)0.69799(12)0.35664(8)0.0207(3)
H65A−0.16300.66950.30080.025*
H65B−0.17830.69980.38540.025*
C66−0.03388(12)0.61844(11)0.38711(8)0.0172(2)
H66A−0.08340.54140.37700.021*
H66B0.00430.64200.44420.021*

Source of materials

The title complex was prepared from the in situ reaction of CuCl, Cy3P and NH4[S2CN(CH2)4] in a 1:2:1 ratio. Cy3P (Sigma–Aldrich; 0.6 mmol, 0.171 g) dissolved in hexane (10 mL) was added to a hexane solution (10 mL) of CuCl (Sigma–Aldrich; 0.3 mmol, 0.030 g). The temperature of reaction was maintained at below 4 °C in an ice-bath. Then, NH4[S2CN(CH2)4] (Sigma–Aldrich, 0.3 mmol, 0.055 g) in hexane (10 mL) was added to the reaction mixture followed by stirring for 4 h. The resulting mixture was filtered and quickly evaporated to yield a brownish solid. This was recrystallised from its chloroform solution via slow evaporation at room temperature to yield colourless crystals. Yield: 0.089 g (61.5%). M.p.: 416 K.

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.99–1.00 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C). Owing to poor agreement, three reflections, i.e. (−3 5 20), (−2 6 19) and (−8 14 2), were omitted from the final cycles of refinement.

Comment

Motivations to investigate molecules of the general formula [R3PCu(S2CNRR′)]2, R, R′ = alkyl or aryl, are founded in materials science, e.g. as precursors for copper sulphide nanomaterials [5], and metal-based drugs, e.g. as anti-microbials [6]. It was the latter impetus that led to the synthesis of the title compound, namely {Cy3PCu[S2CN(CH2)4]}2.

The binuclear molecular structure is shown in the Figure (70% displacement ellipsoids); there is no crystallographically-imposed symmetry in the molecule. Each of the pyrrolidinyldithiocarbamato ligands is μ2-bridging, chelating one copper(I) centre while simultaneously binding to a second via one of the sulphur atoms only, i.e. S1 and S3. Non-systematic variations are noted in the Cu—S bond lengths. Thus, for the Cu1 centre, the Cu1—S1, S2 and S3 bond lengths of 2.4391(3), 2.4072(3) and 2.3653(3) Å, respectively, correspond to the bridging atom of the chelating ligand, the non-bridging atom and the incoming sulphur-bridge from the second dithiocarbamate ligand. The corresponding atoms for the Cu2 atom are S3, S4 and S1, respectively, and the bond lengths are 2.4787(3), 2.3603(3) and 2.4346(3) Å, respectively. These values indicate that the S1 atom forms a more symmetric bridge than the S3 atom, as seen in the value of Δ(Cu—S1bridge) = 0.004 Å, cf. Δ(Cu—S3bridge) = 0.113 Å. By contrast, the different modes of association of the sulphur atoms result in systematic differences in the associated S—C bond lengths with the S1 and S3 atoms, each forming two Cu—S interactions, being longer at 1.7456(13) and 1.7413(13) Å cf. the S—C bonds formed by the S2 and S4 atoms of 1.7123(13) and 1.7078(13) Å.

The central Cu2S2 core is based on a skewed rectangle with the range of Cu—S bond lengths being 2.3653(3) to 2.4787(3) Å, and the r.m.s. of the best plane through the Cu2S2 atoms is 0.0931 Å with deviations above and below the plane of 0.0957(1) Å for the Cu1 atom and 0.0935(1) Å for S3. The CuS2C chelate rings lie to the same side of the central Cu2S2 core and form dihedral angles of 75.66(12)° [Cu1-chelate] and 74.21(13)° [Cu2-chelate] with the core; the dihedral angle between the chelate rings is 30.14(3)°. The PS3 coordination geometry for each copper(I) atom is completed by the phosphorus atom of a Cy3P ligand; both of these lie to the same side of the Cu2S2 core. The coordination geometries exhibit significant distortions from the ideal geometry none the least owing to the acute chelate angles of 75.400(11)° [Cu1-chelate] and 75.494(11)° [Cu2-chelate]. The widest angle in each coordination geometry is the one involving the bridging-S atom and the phosphane ligand, i.e. S1—Cu1—P1 of 129.119(14)° and S3—Cu2—P1 of 132.003(13)°.

There are three direct literature precedents for the structure of the title compound, namely [R3PCu(S2CNEt2)]2 for R = Me and Et [5], and Cy [7]. These adopt the same structural motif in that each is centrosymmetric and each features a similar μ2-bridging mode for the dithiocarbamate ligand. Crucially, the symmetry implies the CuS2C chelate rings lie to opposite sides of the Cu2S2 core with the result the Cu2S4C2 atoms describe a chair (or step-ladder topology) as opposed to the boat form seen in the structure of {Cy3PCu[S2CN(CH2)4]}2. A search of the Cambridge Structural Database [8] shows there are seven examples silver analogues of general formula [R3PAg(S2CNRR′)]2, R, R′ = alkyl or aryl. Each of these adopts the chair form so it seems the structure reported herein stands alone in this class of compound.

Acknowledgements

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

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Received: 2017-12-12
Accepted: 2018-3-18
Published Online: 2018-3-30
Published in Print: 2018-5-24

©2018 Yi Jiun Tan 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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  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
https://doi.org/10.1515/ncrs-2017-0406
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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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