Startseite The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
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The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd

  • Jian Yang EMAIL logo
Veröffentlicht/Copyright: 15. August 2018

Abstract

C25H33Cl2N3OPd, triclinic, P1̄ (no. 2), a = 10.2439(9) Å, b = 11.4323(9) Å, c = 11.9773(11) Å, α = 93.043(3)°, β = 94.892(3)°, γ = 114.364(2)°, V = 1267.07(19) Å3, Z = 2, Rgt(F) = 0.0212, wRref(F2) = 0.0528, T = 173(2) K.

CCDC no.: 1856821

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 prismatic
Size:0.18 × 0.13 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.97 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:26.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:22323, 4949, 0.038
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4676
N(param)refined:300
Programs:SHELX [1], Bruker [2]
Table 2:

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

AtomxyzUiso*/Ueq
Pd10.57010(2)0.35190(2)0.21433(2)0.01767(7)
H30.391(2)0.3674(19)0.0794(16)0.025(6)*
Cl10.66752(5)0.44321(5)0.05680(4)0.03315(12)
Cl20.46244(5)0.25397(5)0.36544(4)0.02939(11)
O10.06454(14)0.17760(14)0.06020(13)0.0351(3)
N10.80176(15)0.27759(14)0.30940(12)0.0191(3)
N20.88048(15)0.48325(14)0.31415(13)0.0193(3)
N30.36886(16)0.31930(16)0.12718(14)0.0233(3)
C10.76030(18)0.37259(17)0.28440(14)0.0186(4)
C20.94546(19)0.32908(18)0.35467(16)0.0228(4)
H20.99880.28210.37880.027*
C30.99450(19)0.45704(18)0.35784(16)0.0227(4)
H3A1.08940.51860.38480.027*
C40.89782(19)0.61480(17)0.30710(15)0.0199(4)
C50.99278(19)0.68826(18)0.23455(16)0.0232(4)
C61.0232(2)0.81870(19)0.23823(17)0.0279(4)
H61.08790.87080.19000.034*
C70.9616(2)0.87509(18)0.31049(18)0.0293(4)
C80.8652(2)0.79791(19)0.37862(17)0.0276(4)
H80.82050.83560.42630.033*
C90.8313(2)0.66617(18)0.37961(16)0.0232(4)
C100.7273(2)0.5875(2)0.45655(17)0.0287(4)
H10A0.63180.54000.41390.043*
H10B0.72110.64490.51760.043*
H10C0.76120.52640.48830.043*
C111.0604(2)0.6301(2)0.15393(17)0.0298(4)
H11A1.13450.61100.19610.045*
H11B1.10470.69130.09930.045*
H11C0.98600.55020.11410.045*
C121.0001(3)1.0179(2)0.3156(2)0.0434(6)
H12A1.10321.06630.34140.065*
H12B0.94351.03970.36810.065*
H12C0.97881.04040.24050.065*
C130.71221(18)0.14014(17)0.30020(15)0.0192(4)
C140.66583(19)0.06977(18)0.19467(16)0.0221(4)
C150.5868(2)−0.06326(19)0.19288(17)0.0274(4)
H150.5506−0.11330.12210.033*
C160.5592(2)−0.12519(18)0.28998(18)0.0279(4)
C170.6082(2)−0.05154(19)0.39288(17)0.0271(4)
H170.5896−0.09310.46010.033*
C180.68414(19)0.08195(18)0.40033(16)0.0222(4)
C190.7339(2)0.1593(2)0.51387(16)0.0297(4)
H19A0.83900.19160.52950.045*
H19B0.68810.10420.57200.045*
H19C0.70700.23220.51380.045*
C200.7036(2)0.1306(2)0.08676(16)0.0292(4)
H20A0.68590.20860.08740.044*
H20B0.64370.06940.02280.044*
H20C0.80560.15340.07980.044*
C210.4801(3)−0.2705(2)0.2832(2)0.0431(6)
H21A0.4001−0.30050.22230.065*
H21B0.4422−0.29590.35480.065*
H21C0.5468−0.30940.26800.065*
C220.2601(2)0.34574(18)0.18372(17)0.0254(4)
H22A0.29970.43870.21020.030*
H22B0.23810.29630.25030.030*
C230.1221(2)0.3090(2)0.10485(18)0.0302(4)
H23A0.04980.32380.14620.036*
H23B0.14230.36470.04220.036*
C240.1667(2)0.1541(3)0.0001(2)0.0462(6)
H24A0.18920.2088−0.06330.055*
H24B0.12490.0627−0.03150.055*
C250.3040(2)0.1838(2)0.07701(19)0.0354(5)
H25A0.28220.12550.13780.043*
H25B0.37400.16780.03360.043*

Source of material

By Shao and co-worker’s pioneering work, the title compound was obtained in 80% isolated yields after flash column chromatography [3]. Crystals suitable for X-ray diffraction were obtained by slow evaporation of the mixed solvents of dichloromethane and ethyl acetate.

Experimental details

All hydrogen atoms attached to C atoms were introduced using the HFIX command in the SHELXL program [1]. The C—H distances in CH2 were restrained to 0.99 Å with Uiso values to be 1.2Ueq(C). The C—H distances in CH3 were restrained to 0.98 Å with Uiso values to be 1.5Ueq(C). All other vinylic and aromatic C—H distances were restrained to 0.95 Å with Uiso values to be 1.2Ueq(C) [1].

Comment

In 2012, Shao and co-workers found that the iso-propyl analogue of the title compound is the active catalytic species for the Suzuki-Miyaura coupling of aryl sulfonates [4]. In the next year, the same group reported the facile synthesis of the title compound and its analogue and showed them to be efficient catalysts in the Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids. However, only crystal structure of the iso-propyl analogue of the title compound was reported therein. Therefore, we think it necessary to report the crystal structure of the title compound in this case to understand more information about such compounds.

The structure of the title complex is very similar to its iso-propyl analogue. The Pd—Ccarbene and Pd—N bond lengths of the title compound are 1.9688(17) and 2.1062(15) Å, respectively. Generally all geometric parameters are in perfect accordance with the literature [5].

Acknowledgements

I acknowledge Hunan Agricultural University for its financial support for this project.

References

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

Bruker. SADABS, Version 2.03, SAINT, Version 6.02. Bruker AXS Inc. Madison, WI, USA (2002).Suche in Google Scholar

Wang, Z.-Y.; Ma, Q.-N.; Li, R.-H.; Shao, L.-X.: Palladium-catalyzed Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids. Org. Biomol. Chem. 11 (2013) 7899–7906.10.1039/c3ob41382aSuche in Google Scholar PubMed

Wang, Z.-Y.; Chen, G.-Q.; Shao, L.-X.: N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids. J. Org. Chem. 77 (2012) 6608–6614.10.1021/jo301270tSuche in Google Scholar PubMed

Liu, F.; Li, G.-X.: The crystal structure of dichlorido (1,3-dimesityl1H-3λ4-imidazol-2-yl)(isoquinoline-κN)palladium(IV) – ethylacetate (1/1), C34H39Cl2N3O2Pd. Z. Kristallogr. NCS 231 (2016) 1143–1144.10.1515/ncrs-2016-0093Suche in Google Scholar

Received: 2018-04-17
Accepted: 2018-07-19
Published Online: 2018-08-15
Published in Print: 2018-11-27

©2018 Jian Yang, published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-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, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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