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Crystal structure of the phosphorescent complex diethyldithiophosphonato-κ2S,S′-bis(2-phenylpyridinato-κ2C,N)iridium(III), C26H26N2O2PS2Ir

  • Lianqing Chen EMAIL logo and Zhongda Wu
Published/Copyright: March 11, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 4

Abstract

C26H26N2O2PS2Ir, orthorhombic, P212121 (no. 19), a = 9.4097(6) Å, b = 13.2837(9) Å, c = 20.6400(14) Å, V = 2579.9(3) Å3, Z = 4, Rgt(F) = 0.0202, wRref(F2) = 0.0471, T = 293(2) K.

CCDC no.: 1888672

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:Yellow block
Size:0.44 × 0.32 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:5.43 mm−1
Diffractometer, scan mode:Bruker D8 Venture, φ and ω
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:15950, 6267, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5514
N(param)refined:309
Programs:CrysAlisPRO [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.3077(4)0.1013(3)0.2149(2)0.0385(9)
C20.2968(5)0.0502(4)0.2737(2)0.0522(12)
H20.256444−0.0136800.2743830.063*
C30.3446(6)0.0922(5)0.3309(2)0.0623(14)
H30.3347030.0566850.3694150.075*
C40.4068(6)0.1862(5)0.3316(2)0.0643(15)
H40.4399670.2133300.3702720.077*
C50.4196(5)0.2393(4)0.2751(3)0.0576(13)
H50.4610620.3028810.2754430.069*
C60.3707(4)0.1984(4)0.2167(2)0.0415(10)
C70.3785(4)0.2494(4)0.1546(2)0.0443(10)
C80.4328(5)0.3462(4)0.1446(3)0.0599(13)
H80.4686660.3829200.1793300.072*
C90.4329(6)0.3869(5)0.0833(3)0.0729(17)
H90.4691370.4510210.0760730.087*
C100.3794(6)0.3321(4)0.0334(3)0.0728(16)
H100.3760100.359191−0.0081470.087*
C110.3307(6)0.2371(4)0.0446(2)0.0598(13)
H110.2970950.1995690.0097160.072*
C120.0503(4)0.1060(4)0.14078(19)0.0424(10)
C13−0.0028(5)0.2026(4)0.1306(2)0.0550(12)
H130.0584420.2530890.1165980.066*
C14−0.1446(6)0.2252(5)0.1407(3)0.0735(17)
H14−0.1778050.2901890.1334780.088*
C15−0.2360(7)0.1516(6)0.1614(3)0.0820(18)
H15−0.3313030.1670420.1680630.098*
C16−0.1887(6)0.0557(6)0.1725(3)0.0738(17)
H16−0.2511820.0062540.1868510.089*
C17−0.0452(5)0.0328(4)0.1619(2)0.0523(12)
C180.0131(6)−0.0675(4)0.1715(2)0.0527(12)
C19−0.0595(6)−0.1520(5)0.1929(3)0.0721(17)
H19−0.156148−0.1473270.2017570.086*
C200.0082(9)−0.2415(5)0.2013(3)0.0833(19)
H20−0.041322−0.2975050.2161740.100*
C210.1513(8)−0.2482(4)0.1873(3)0.0784(18)
H210.199592−0.3088750.1917290.094*
C220.2211(6)−0.1629(3)0.1666(2)0.0584(14)
H220.317990−0.1667850.1580240.070*
C230.3078(7)−0.2522(4)−0.0200(3)0.091(2)
H23A0.206801−0.238006−0.0177090.109*
H23B0.340487−0.235656−0.0632380.109*
C240.3315(7)−0.3562(5)−0.0077(3)0.090(2)
H24A0.296212−0.3729880.0345840.134*
H24B0.431575−0.370078−0.0096540.134*
H24C0.282900−0.395693−0.0397020.134*
C250.5204(8)0.0299(5)−0.0724(3)0.0795(19)
H25A0.5905860.063921−0.0458090.095*
H25B0.4366130.072182−0.0748360.095*
C260.5778(9)0.0133(5)−0.1376(3)0.088(2)
H26A0.5983000.077075−0.1574280.131*
H26B0.509230−0.022240−0.1632980.131*
H26C0.663520−0.025632−0.1347250.131*
Ir10.24925(2)0.05523(2)0.12619(2)0.03505(5)
N10.3291(4)0.1952(3)0.10392(17)0.0417(8)
N20.1549(4)−0.0745(3)0.15824(17)0.0424(8)
O10.3834(4)−0.1904(2)0.02748(16)0.0553(8)
O20.4841(4)−0.0654(2)−0.04351(16)0.0575(8)
P10.39312(13)−0.07235(9)0.02057(6)0.0440(3)
S10.48920(14)−0.01948(11)0.09878(7)0.0528(3)
S20.20587(12)−0.00357(9)0.01168(5)0.0483(3)

Source of material

Iridium trichloride hydrate and 2-phenylpyridine and solvents were of reagent grade quality obtained from commercial suppliers (Wuhan Guoyao Chemical Reagent Co., Ltd.) and used without further purification. The synthesis of the target product involves two steps. First, iridium trichloride hydrate (0.352 g, 1.0 mmol) was combined with 2.5 eq. of the ligand, 2-phenylpyridine (0.385 g, 2.5 mmol) and dissolved in a mixture of 2-ethoxyethanol (30 mL) and water (10 mL), and finally refluxed for 24 h. The solution was cooled to room temperature, and the yellow precipitate was collected by filtration and dried under the vacuum at ambient temperature. The crude product was directly used for the next step without further purification. In the second step, the product (0.075 mmol), potassium O,O′-diethyldithiophosphate (Et2dtp) (0.25 mmol) and anhydrous sodium carbonate (Na2CO3, 1.0 mmol) were dissolved in 2-ethoxyethanol (10 mL). The mixture was refluxed under argon for 12 h. After cooling to room temperature, a small quantity of water was added. The resulting yellow precipitate was collected by filtration, washed with water, ethanol and hexane, and dried in vacuum. The crude product was purified by column chromatography on silica gel with CH2Cl2/petroleum ether (1:3) as the eluent. The residue was dried under vacuum and recrystallized from dichloromethane/hexane (1:1, v/v). Yield: 0.256 g (71.6%). 1H NMR (CDCl3, 400 MHz, ppm) δ 1.26 (t, J = 7.2 Hz, 6H), 3.99 (q, J = 7.2 Hz, 4H), 6.22 (d, J = 6.8 Hz, 2H), 6.45 (t, J = 7.2 Hz, 2H), 6.76 (t, J = 8.4 Hz, 2H), 7.14–7.21 (m, 2H), 7.48 (d, J = 8.4 Hz, 2H), 7.68 (t, J = 6.8 Hz, 2H), 7.82 (d, J = 7.2 Hz, 2H), 9.67 (d, J = 8.4 Hz, 2H). Calcd. for C26H26N2O2PS2Ir: C, 66.31; H, 4.42; N, 6.89%, Found: C, 65.63; H, 4.17; N, 7.29%. MS (FAB): m/e, 686 (M+).

After allowing the dichloromethane/hexane (1:1, v/v) solution to stand in air for 6 d, light yellow block crystals were formed by slow evaporation of the solvent. The crystals were isolated, washed with light petroleum and dried in vacuum (yield 87.6%).

Experimental details

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq for aryl H atoms and 1.5 Ueq for the methyl H atoms. Methyl H atoms were allowed to rotate to best fit the experimental electron density.

Comment

Recently, heavy metal complexes in OLEDs have attracted much attention as efficient phosphors because they can harvest both singlet and triplet excited states, and thus the OLEDs internal efficiency can theoretically reach 100% [5]. Especially iridium(III) complexes with cyclometalated ligands show intense phosphorescence at room temperature and this behavior makes them very promising phosphor dyes in OLEDs [6], [7]. Furthermore, metal complexes containing dithiolate ligands have been extensively studied. However, only a limited number of iridium(III) dithiolate complexes have been described [8], [9]. The title compound, which emits green luminescence in both solid state and organic solution upon irradiation by UV-light at ambient temperature, may play a very important role as a potential electrophosphorescent material.

In the crystal structure of the title molecule, the Ir(III) center resides in a distorted octahedral environment. The nitrogen donors of the two chelating 2-phenylpyridinato ligands are in trans posistion to each other. Consequently the two carbon atoms are in a cis configuration. The Ir—C bonds (2.008(4), 2.012(4) Å) are slightly shorter than the Ir—N bond distances (2.048(4), 2.058(4) Å). These values are very similar to those in similar complexes such as (ppy)2Ir(acac) (ppy: 2-phenylpyridine; acac: actylacetone) (Ir—C: 2.020(2) Å; Ir—N: 2.090(10) Å) [10]. The similarity of the Ir—S bond lengths (2.5304(13), 2.5226(11) Å) in the O,O′-diethyldithiophosphate (Et2dtp) ligand indicates that the charge is delocalized over both sulfur atoms as expected. The Et2dtp chelate angle S(2)—Ir(1)—S(1) is 79.25(4)°, and the phenyl and metalated pyridine rings in the same ppy ligand are coplanar (the dihedral angle between the two planes is 0.3(2)°) [11].

The packing exhibits intermolecular hydrogen bonding and π⋯π stacking interactions between aromatic rings in neighboring complexes, which assemble a two-dimensional structure. Two molecules form a dimer by the C22—H22⋯O1 hydrogen bondings and these dimers are connected by π⋯π stacking interactions along the a axis of the unit cell, with face-to-face distances of ca. 3.154 Å, constructing a zigzag chain. These zigzag chains are interacted by π⋯π stacking interactions along the c axis, with face-to-face distances of ca. 3.116 Å, building up a two-dimensional structure.

To further explore the luminescence property of the title compound, the absorption and photoluminescence spectra of in CH2Cl2 solution were investigated. In the absorption spectrum, intense absorptions are observed in the ultraviolet region of the spectrum, between 243 and 310 nm, which can be assigned to the spin allowed π–π* transition from cyclometalated ligands. The weaker absorption bands in the range of 315–445 nm can likely be assigned to metal-to-ligand charge transfer (MLCT) and 3π–π* transition [12], [13]. The photoluminescence spectrum shows two major peaks at 494 and 533 nm. The vibronic fine structures in the PL spectrum imply that the emissions predominantly result from ligand-based 3π–π* transition [14].

To further investgate the thermal stability of the title compound, thermogravimetric analysis (TGA) was performed. The TGA curve exhibited the first endothermic weight loss of ca. 26.13% in the temperature range of 303–385 °C, with an endothermic process centered at 352 °C, assigned to the liberation of ancillary ligands moiety, Et2dtp (calcd. 26.83%). The result was in good agreement with the mass spectra peak at 501, arising from the Ir(ppy)2+ fragment. In the temperature range of 390–440 °C the second endothermic weight loss of ca. 22.16% may be the result of the cleavage of one cyclometalated ligand. The excellent thermal stability of the title compound was presumably due to the great stabilizing capability of ditholate ligands to metal ions.

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 20702064

Award Identifier / Grant number: 21177161

Award Identifier / Grant number: 31402137

Funding statement: The authors thank the Natural Science Foundation of Hubei province for Distinguished Yong Scholars (No.2013CFA034); National Natural Science Foundation of China (grant No. 20702064, 21177161 and 31402137); the Program for Excellent Talents in Hubei Province (RCJH15001); the Opening Project of Key Laboratory of Green Catalysis of Sichuan Institutes of High Education (LYZ1107) and the Fundamental Research Funds for the Central University, South-Central University for Nationalities (CZP17077).

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Received: 2019-01-07
Accepted: 2019-02-08
Published Online: 2019-03-11
Published in Print: 2019-06-26

© 2019 Lianqing Chen 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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  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
https://doi.org/10.1515/ncrs-2019-0020
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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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