Home Physical Sciences Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
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Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 4

Abstract

C14H20N2O4P2S4Zn, triclinic, P1̄ (no. 2), a = 8.0014(2) Å, b = 10.3376(2) Å, c = 14.2488(3) Å, α = 84.676(2)°, β = 76.042(2)°, γ = 79.752(2)°, V = 1124.01(4) Å3, Z = 2, Rgt(F) = 0.0265, wRref(F2) = 0.0655, T = 100(2) K.

CCDC no.: 1897161

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:Prism, colorless
Size:0.13 × 0.12 × 0.08 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:6.54 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω-scans
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:21867, 4014, 0.023
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3854
N(param)refined:248
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
Zn0.46343(3)0.27283(2)0.73472(2)0.01664(8)
P10.38164(7)0.59038(5)0.79734(4)0.01873(12)
P20.82244(7)0.05797(5)0.70454(4)0.01998(12)
S10.56722(6)0.43041(5)0.79876(3)0.01991(11)
S20.14367(7)0.57448(5)0.86223(5)0.03204(14)
S30.65819(7)0.14158(6)0.61888(4)0.02815(13)
S40.73109(7)0.07731(7)0.84130(4)0.03506(15)
O10.4511(2)0.70523(14)0.83702(11)0.0267(3)
O20.4066(2)0.63970(15)0.68607(10)0.0267(3)
O31.0025(2)0.11140(15)0.66932(11)0.0266(3)
O40.88684(19)−0.09007(14)0.67307(12)0.0272(3)
N10.3015(2)0.17093(16)0.83413(11)0.0173(3)
N20.2890(2)0.35794(15)0.64923(11)0.0162(3)
C10.4552(4)0.7019(3)0.93833(18)0.0393(6)
H1A0.4842720.7850010.9526540.059*
H1B0.5434630.6287650.9523080.059*
H1C0.3404890.6897120.9785530.059*
C20.2830(4)0.7433(3)0.65822(18)0.0397(6)
H2A0.2925960.7431870.5883440.059*
H2B0.3060030.8277590.6740270.059*
H2C0.1650780.7305070.6930500.059*
C31.0985(3)0.1029(2)0.56954(17)0.0334(5)
H3A1.2053020.1409990.5607940.050*
H3B1.0261770.1515650.5271900.050*
H3C1.1290090.0104060.5530210.050*
C40.7687(4)−0.1842(3)0.7003(2)0.0497(7)
H4A0.831707−0.2721140.6827630.075*
H4B0.673889−0.1602550.6661940.075*
H4C0.719966−0.1843850.7703010.075*
C50.2111(3)0.2216(2)0.91792(16)0.0275(5)
H50.2280560.3057210.9320740.033*
C60.0946(3)0.1569(2)0.98448(16)0.0278(5)
H60.0344250.1959881.0435730.033*
C70.0649(2)0.03512(19)0.96561(14)0.0167(4)
C80.1618(3)−0.0178(2)0.88001(17)0.0280(5)
H80.148929−0.1024230.8646010.034*
C90.2772(3)0.0519(2)0.81694(17)0.0275(5)
H90.3425250.0133250.7585060.033*
C100.3489(3)0.39310(19)0.55554(14)0.0187(4)
H100.4714600.3789640.5297880.022*
C110.2420(3)0.4485(2)0.49494(14)0.0186(4)
H110.2906620.4713500.4291100.022*
C120.0607(2)0.47097(18)0.53119(14)0.0151(4)
C13−0.0003(3)0.43506(19)0.62835(14)0.0187(4)
H13−0.1221040.4487580.6563020.022*
C140.1156(3)0.37956(19)0.68428(14)0.0188(4)
H140.0706560.3556660.7503860.023*

Source of material

The Zn[S2P(OMe)2]2 precursor was prepared in high yield from an in-situ reaction of Zn(NO3)2.4H2O (Alfa Aesar; 7.18 g, 0.05 mol), MeOH (Merck; 8.52 mL, 0.21 mol), P2S5 (Sigma-Aldrich; 11.71 g, 0.05 mol) and 50% w/w NaOH solution (Merck; 8.43 mL, 0.11 mol). The title compound was obtained by mixing the suspension of this precursor (0.50 g, 1.32 mmol) and 4,4′-bipyridine (Merck; 0.21 g, 1.34 mmol) in dimethylformamide (Merck; 5 mL), followed by stirring for 30 mins at 373 K. The solution was filtered and the filtrate was collected in a sample vial containing acetonitrile (Merck; 1 mL). Colorless blocks formed after one day. Yield: 0.38 g, (54%, based on Zn[S2P(OMe)2]2). M. pt (Biobase Automatic Melting Apparatus MP45): 418.85−420.95 K. IR (Bruker Vertex 70 V equipped with Platinum ATR from 400 to 80 cm−1, cm−1): 1172 (s) ν(C—O); 1008(s) ν(P—O); 664 (s) ν(P—S)asym; 526 (m) ν(P—S)sym.

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95−0.98 Å) and refined as riding with Uiso(H) = 1.2−1.5Ueq(C). Owing to relatively high motion, the anisotropic displacement parameters for the C5—C9 atoms were constrained to be nearly isotropic.

Discussion

Through the agency of sulphur bridging, homoleptic zinc dithiophosphates, Zn[S2P(OR)2]2, are associated in the solid-state [5]. This mode of association invariably breaks down when potentially bidentate bridging molecules, e.g. 4,4′-bipyridine, are complexed with these species [6], forming Zn—N bonds instead. Systematic evaluations of co-crystallisation outcomes when Zn[S2P(OR)2]2 and bidentate donors have been conducted [7], [8]. These studies showed that steric influences were important in determining the ultimate structure, for example when R = bulky cyclohexyl, only binuclear species could be isolated when the bridging ligand was 4,4′-bipyridine, regardless of the stoichiometry of the reagents [8]. Even more striking was the observation of monodentate coordination when the potentially bridging ligand was 1,2-bis(2-pyridyl)ethene [7]. In the present study the crystal and molecular structures of {Zn[S2P(OMe)2]2(4,4′-bipyridine)}n are described, where R is a relatively small methyl group.

The asymmetric unit of the title structure, extended to show the full 4,4′-bipyridine molecules (each is disposed about a centre of inversion) is shown in the upper view of the Figure (70% displacement ellipsoids; symmetry operations i: − x, − y, 2 − z and ii: − x, 1–y, 1–z). The zinc(II) centre is coordinated by two monodentate dithiophosphate ligands [Zn—S1, S3 = 2.3019(5) and 2.3273(6) Å] and two nitrogen atoms derived from two bridging 4,4′-bipyridine ligands [Zn—N1, N2 = 2.0295(17) and 2.0951(16) Å]. The non-coordinating Zn⋯S2, S4 separations [3.9422(6) and 3.2307(7) Å] are too long to be considered bonding interactions. The distortions from a regular tetrahedral geometry for the resultant N2S2 donor set are relatively small with the angles ranging from 97.79(5)°, for N2—Zn—S3, to 118.10(2)°, for S1—Zn—S3. The monodentate mode of coordination of the dithiophosphate ligands is reflected in the significant disparity in the associated P—S bond lengths. Thus, the P—S bonds formed with the non-coordinating S2 and S4 atoms are significantly shorter than the bonds involving the coordinating S1 and S3 atoms [P1—S1, S2 = 2.0185(7) and 1.9342(7) Å; P2—S3, S4 = 2.0341(7) and 1.9248(7) Å].

As seen in the lower view of the Figure, the resulting one-dimensional coordination polymer has a zig-zag topology and is aligned along [0 1 2̄]. Besides the binuclear species mentioned above, there are two literature precedents for comparison. Thus, for each of {Zn[S2P(OR)2]2(4,4′-bipyridine)}n, i.e. R = Et [9] and R = iPr [10], zig-zag chains are observed as for the title structure. To a first approximation the pitch of each polymer is about the same, being 16.8 Å in the structure reported here, 16.4−17.5 Å for the R = Et species (for which there are two independent zinc atoms) and 15.9−16.1 Å for the R = iPr species (three independent zinc atoms).

In the crystal, pyridyl-C—H⋯S [C6—H6⋯S2iii = 2.82 Å, C6⋯S2iii = 3.654(2) Å with angle at H6 = 148° and C13—H13⋯S1iv = 2.83 Å, C13⋯S1iv = 3.723(2) Å with angle at H13 = 157° for symmetry operations iii: −x, 1 − y, 2 − z and iv: −1 + x, y, z] and methyl-C—H⋯π(pyridyl) [C3—H3a⋯Cg(N2,C10—C14)v = 2.85 Å, C3⋯Cg(N2,C10—C14)v = 3.436(2) Å with angle at H3a = 119° for symmetry operation v: 1 + x, y, z] interactions link the chains into a three-dimensional architecture.

Acknowledgements

Sunway University is thanked for support of crystal engineering studies of metal 1,1-dithiolates.

References

1. Agilent Technologies: CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA (2017).Search in Google Scholar

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

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

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

5. Tiekink, E. R. T.: Exploring the topological landscape exhibited by binary zinc-triad 1,1-dithiolates. Crystals 8 (2018) article no. 292 (34 pages).10.3390/cryst8070292Search in Google Scholar

6. Tiekink, E. R. T.: Perplexing coordination behaviour of potentially bridging bipyridyl-type ligands in the coordination chemistry of zinc and cadmium 1,1-dithiolate compounds. Crystals 8 (2018) article no. 18 (29 pages).10.3390/cryst8010018Search in Google Scholar

7. Lai, C. S.; Liu, T.; Tiekink, E. R. T.: Steric control over polymer formation and topology in adducts of zinc dithiophosphate formed with bridging bipyridine ligands. CrystEngComm 6 (2004) 221–226.10.1039/b407335eSearch in Google Scholar

8. Chen, D. Lai, C. S.; Tiekink, E. R. T.: Supramolecular aggregation in diimine adducts of zinc(II) dithiophosphates: controlling the formation of monomeric, dimeric, polymeric (zig-zag and helical), and 2-D motifs. CrystEngComm 8 (2006) 51–58.10.1039/B513393ASearch in Google Scholar

9. Zhu, D.-L.; Yu, Y.-P.; Guo, G.-C.; Zhuang, H.-L.; Huang, J.-S.; Liu, Q.; Xu, Z.; You, X.-Z.: catena-poly[bis(κO,O′-diethyldithiophosphato-S)zinc(II)-4,4′-bipyridyl-κN:N′]. Acta Crystallogr. C52 (1996) 1963–1966.10.1107/S010827019600368XSearch in Google Scholar

10. Glinskaya, L. A.; Shchukin, V. G.; Klevtsova, R. F.; Mazhara, A. N.; Larionov, S. V.: Synthesis and polymer structure of [Zn(4,4′-bipy)-{(i-PrO)2PS2}2]n and thermal properties of ZnL{(i-PrO)2PS2}2(L = phen, 2,2′-bipy, 4,4′-bipy). J. Struct. Chem. 41 (2000) 632–639.10.1007/BF02683926Search in Google Scholar

Received: 2019-01-28
Accepted: 2019-02-14
Published Online: 2019-03-26
Published in Print: 2019-06-26

© 2019 Yee Seng Tan 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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  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
https://doi.org/10.1515/ncrs-2019-0085
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-5-fluorophenol, C14H13FN2O
  3. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4,6-dichlorophenol, C14H12Cl2N2O
  4. The crystal structure of (E)-1-(4-methoxyphenyl)-3-(2-nitrophenyl)triaz-1-ene C8H8N2O4
  5. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one—methanol (1:1), C32H30N5O2Br ⋅ CH4O
  6. Crystal structure of 2,4-pentanedione bis(2,4-dinitrophenylhydrazone), C17H16N8O8
  7. Crystal structure of sodium morpholine-4-carbodithioate, (C5H12NNaO3S2)
  8. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorido phosphate), C16H28F12N4P2
  9. Crystal structure of 5-(4-chlorophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C21H16ClFN2
  10. Crystal structure of catena-poly[diaqua-bis(3-carboxy-5-methoxybenzoato-κO)-(1,2-bis(imidazol-1-yl)ethane-κ2N:N′)cobalt(II)], C26H28CoN4O12, [Co(C9H6O5)2(H2O)2(C8H10N4)]
  11. The crystal structure of 3-cyclohexyl-1,5-dioxaspiro[5.5]undecane-2,4-dione, C15H22O4
  12. Crystal structure of (2,4-dimethoxybenzyl)triphenylphosphonium trifluoroacetate — trifluoroacetic acid (1/1), C31H27F6O6P
  13. Crystal structure of 4-tert-butyl-1-(2,6-dimethylphenyl)-1H-1,2,3-triazole, C14H19N3
  14. Crystal structure of 1,1′-methylenebis(4-tert-butylpyridinium) tetrachloridocobaltate(II) – dichloromethane (1:1), C20H30Cl6CoN2
  15. Crystal structure of (4,4′-(ethane-1,2-diylbis((nitrilo)(2-furylmethylylidene)))bis(3-methyl-1-phenyl-1H-pyrazol-5-olato-κ4N,N′,O,O′))-nickel(II)), C32H26N6NiO4
  16. Synthesis and crystal structure of bis{((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ2N,O}copper(II), C44H38CuN4O4
  17. Crystal structure of catena-poly[diaqua-bis(3,5-dichloropyridine-4-carboxylato-κ1O)-bis(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C22H16Cl4CoN4O6
  18. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3,5-dinitrophenyl)diazene 1-oxide, C12H4Cl2N6O9
  19. The crystal structure of 3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydroquinolin — dimethylsulfoxide (1/1), C21H19ClFN3O2S
  20. The crystal structure of dichlorido-bis(1-butyl-1H-imidazole-κN)zinc(II), C14H24Cl2ZnN4
  21. (Z)-N-tert-butyl-1-(2-(3,5-dichlorobenzamido)phenyl) methanimine oxide, C18H18Cl2N2O2
  22. Crystal structure of diaqua-bis(3-carboxy-5-bromoisophthalato-κO)-bis(1-(3-(1H-benzo[d]imidazol-1-yl)propyl)-1H-benzo[d]imidazol-3-ium-κN)nickel(II) bis(3-carboxy-5-bromoisophthalate), C66H54Br4N8NiO18
  23. Crystal structure of poly[aqua(μ2-5-methoxyisophthalato-κ2O,O′:O′′)-(1,2-bis(imidazol-1′-yl)ethane-κ2N:N′)cobalt(II), C34H36Co2N8O12
  24. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)] terephthalate tetrahydrate, MnC32H38N10O10
  25. Crystal structure of the fluorescent fipronil derivative 5,5′-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile), C25H6N8O2Cl4F12S2
  26. Crystal structure of the phosphorescent complex diethyldithiophosphonato-κ2S,S′-bis(2-phenylpyridinato-κ2C,N)iridium(III), C26H26N2O2PS2Ir
  27. The crystal structure of 4,10-diethoxy-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine, C18H18O5
  28. Crystal structure of dichlorido-bis(N-benzyl-2-(quinolin-8-yloxy)acetamide-κ2N,O)copper(II) — ethyl acetate (1/1), C38H36N4O6Cl2Cu
  29. Synthesis and crystal structure of bis{4-methyl-2-((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)phenolato-κ3N,O,O}copper(II), C92H84Cu2N8O8
  30. The crystal structure of 1,3,5-trinitro-4,6-diazidobenzene, C6HN9O6
  31. Crystal structure 1-cinnamyl-2-((Z)-styryl)-1H-benzo[d]imidazole — methanol (1/1), C24H20N2 ⋅ CH4O
  32. The crystal structure of poly[m2-aqua-tetraaqua-bis(m9-4-formylbenzene-1,3-disulfonato)tetrasodium(I) hydrate, C14H18O19S4Na4
  33. Crystal structure of 2-((2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium trifluoroacetate, [C17H17F6N2O][C2F3O2]
  34. The crystal structure of bis(ferrocenecarboxylato-κ2O,O′)bis[4-(dimethylamino)pyridine-κN]copper(II) — acetonitrile(1/2), C40H44CuO4Fe2N6
  35. Crystal structure of poly[di-μ2-aqua)-diaqua-bis(μ6-4,4′,4′′-(benzene-1,3,5-triyltris(oxy))tribenzoato-κ6O1:O2:O3:O3:O5:O6)tricadmium(II)] dihydrate, C54H42Cd3O24
  36. The crystal structure of dichlorido(1,3-bis(2,6-diisopropyl-phenyl)-1H-3λ4-imidazol-2-yl)(3-phenyl-pyridine-κN)palladium(IV), C38H45N3Cl2Pd
  37. The crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-phenyl-1,3,5-triazine, C12H8ClN3O
  38. The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S
  39. Crystal structure of bis{μ2-bis{(((((1-methoxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ3N,O:O}copper(II)}, C68H68Cu2N8O8
  40. Crystal structure of catena-poly[tetraaqua-bis(μ2-2-(4-carboxylatophenoxy)benzoato-κ2O:O′)-pentakis(pyridine-κ1N)dinickel(II)], C53H47N5Ni2O13
  41. Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
  42. Redetermination of the crystal structure of bis(μ2-di-ethyldithiocarbamato-κ3S,S′:S;κ3S:S: S′)-hexacarbonyl-di-rhenium(I), C16H20N2O6Re2S4
  43. The crystal structure of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide, C19H16O2N2
  44. Crystal structure of 6-hydroxy-4,8,11b-trimethyltetradecayhdro-8,11-epoxy-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid – methanol (1/1), C20H30O4
  45. The crystal structure of aqua-bis(3-acetyl-2-oxo-2H-chromen-4-olato-κ2O,O′)zinc(II) monohydrate, C22H18O10Zn
  46. Crystal structure of poly[bis(μ2-4-bromoisophthalate-κ2O:O′)-tris(μ2-1-(3-((1H-1,2,4-triazol-1-yl)methyl)benzyl)-1H-1,2,4-triazole-κ2N:N′)dicobalt(II)] monohydrate, C26H23CoN9O5Br
  47. A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2
  48. Crystal structure of catena-poly[diaqua-bis(μ2-4-((4-(pyridin-2-ylmethoxy)phenyl)diazenyl)benzoato-κ3O,O′:N)cadmium(III)], Cd(C19H14O3N3)2(H2O)
  49. Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
  50. Crystal structure of 3-amino-2-hydroxy-6-methoxybenzamide hydrate, C16H22N4O7
  51. Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]
  52. Crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-(thiophen-2-yl)-1,3,5-triazine, C10H6ClN3OS
  53. The crystal structure of 3-butyl-1-methyl-1H-imidazol-3-ium catena-poly[tris(μ2-bromido-κ2Br:Br)lead(II)], C8H15Br3N2Pb
  54. Crystal structure of 3-(5-amino-1H-1,2,4-triazol-3-yl)-1-(piperidin-1-yl)propan-1-one, C10H17N5O
  55. Crystal structure of aqua-2,2′,2′′-(((nitrilo-κN-tris(ethane-2,1-diyl))tris(azanylylidene-κ3N′,N′′,N′′′))tris(methanylylidene))tris(4-chlorophenolato-κ3O,O′,O′′)neodymium(III), C27H26Cl3N4NdO4
  56. Crystal structure of dichlorido-(μ2-2,2′-(diazene-1,2-diyl)bis(benzen-1-ido)-κ2C:C′)dimercury(II), C12H8Cl2Hg2N2
  57. Crystal structure of (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C27H18FN3O3S
  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
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