Home The crystal structure of dichlorido-(1,3-bis(2,6-dimethylphenyl)-1H-imidazol-2(3H)-ylidene)-(morpholine-κ1N)palladium(II), C23H29Cl2N3OPd(II)
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The crystal structure of dichlorido-(1,3-bis(2,6-dimethylphenyl)-1H-imidazol-2(3H)-ylidene)-(morpholine-κ1N)palladium(II), C23H29Cl2N3OPd(II)

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Published/Copyright: July 13, 2018

Abstract

C23H29Cl2N3OPd, monoclinic, P21/c (no. 14), a = 9.6053(2) Å, b = 17.4544(4) Å, c = 14.5156(3) Å, β = 104.6440(10)°, V = 2354.55(9) Å3, Z = 4, Rgt(F) = 0.0184, wRref(F2) = 0.0455, T = 173(2) K.

CCDC no.: 1851691

Table 1:

Data collection and handling.

Crystal:Prismatic, yellow
Size:0.18 × 0.14 × 0.10 mm
Wavelength:Mo Kα radiation (λ =0.71073 Å)
μ:1.035 mm−1
Diffractometer, scan mode:Bruker APEX-II, Φ and ω
Θmax, completeness:26.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:40421, 4597, 0.0285
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 4336
N(param)refined:280
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Pd10.44186(2)0.59504(2)0.29572(2)0.01842(6)
Cl10.32834(4)0.54006(2)0.40204(3)0.02876(10)
Cl20.56841(5)0.63652(3)0.19015(3)0.03942(12)
O10.89028(13)0.66326(8)0.51956(10)0.0367(3)
N10.16752(14)0.56973(8)0.14050(10)0.0224(3)
N20.20747(15)0.68840(8)0.17615(9)0.0217(3)
N30.63118(15)0.59150(8)0.40947(10)0.0217(3)
H30.612(2)0.5607(10)0.4470(13)0.029(5)
C10.26041(17)0.61708(9)0.19956(11)0.0202(3)
C20.08339(19)0.68556(10)0.10234(12)0.0276(4)
H20.02700.72790.07320.033
C30.05872(19)0.61143(10)0.08013(13)0.0293(4)
H3A−0.01870.59120.03210.035
C40.17304(17)0.48724(9)0.14617(11)0.0227(3)
C50.25769(18)0.44817(10)0.09693(12)0.0243(3)
C60.26825(19)0.36889(10)0.10829(13)0.0295(4)
H60.32630.34050.07640.035
C70.1951(2)0.33122(11)0.16551(14)0.0341(4)
H70.20580.27740.17440.041
C80.1064(2)0.37145(11)0.20989(13)0.0315(4)
H80.05420.34460.24720.038
C90.09252(18)0.45072(10)0.20068(12)0.0263(4)
C10−0.0065(2)0.49396(12)0.24746(14)0.0344(4)
H10A0.04830.53310.29000.052
H10B−0.04990.45830.28430.052
H10C−0.08250.51860.19850.052
C110.3302(2)0.48919(11)0.03107(14)0.0335(4)
H11A0.25820.5172−0.01700.050
H11B0.37880.4519−0.00050.050
H11C0.40110.52530.06760.050
C120.25905(18)0.75756(9)0.22851(11)0.0234(3)
C130.21991(19)0.76937(10)0.31388(12)0.0265(4)
C140.2689(2)0.83622(11)0.36419(14)0.0360(4)
H140.24660.84560.42330.043
C150.3494(2)0.88902(12)0.32915(15)0.0401(5)
H150.38240.93410.36460.048
C160.3822(2)0.87697(11)0.24367(15)0.0363(4)
H160.43630.91440.22010.044
C170.3374(2)0.81065(10)0.19069(13)0.0298(4)
C180.3732(3)0.79944(13)0.09689(15)0.0470(5)
H18A0.46130.76890.10620.071
H18B0.38780.84940.07010.071
H18C0.29380.77260.05300.071
C190.1239(2)0.71428(11)0.34830(14)0.0353(4)
H19A0.04170.70090.29550.053
H19B0.08920.73820.39940.053
H19C0.17820.66780.37250.053
C200.77465(18)0.57412(11)0.39448(13)0.0287(4)
H20A0.79150.60690.34270.034
H20B0.77700.52000.37440.034
C210.8937(2)0.58740(11)0.48402(15)0.0341(4)
H21A0.88340.55030.53350.041
H21B0.98790.57830.47000.041
C220.7553(2)0.67698(12)0.54095(14)0.0364(4)
H22A0.75430.72930.56700.044
H22B0.74210.64010.58990.044
C230.63340(18)0.66859(10)0.45247(12)0.0266(4)
H23A0.54080.67770.46890.032
H23B0.64370.70780.40530.032

Source of material

The title compound can be easily obtained in moderate yield according to the literature method [4, 5] . Crystals suitable for X-ray diffraction were grown in a mixture of ethyl acetate and petroleum ether.

Experimental details

All hydrogen atoms attached to C atoms were introduced using the HFIX command in the SHELXL program [3]. The C—H distances in CH3 were restrained to 0.96 Å with Uiso values to be 1.5Ueq(C). Vinylic and aromatic C—H distances were restrained to 0.93 Å with Uiso values to be 1.2Ueq(C).

Discussion

N-Heterocyclic carbene-palladium(II) complexes, which usually are air- and thermal-stable, have shown excellent catalytic activity in the cross-coupling reactions [6], [7], [8]. Recently it was found that besides the carbene, the anicillary ligands played important roles in the complexes [9], [10], [11], [12], [13]. N-Heterocyclic carbene-Pd(II) complexes using morpholine as the anicillary ligand were used in the coupling of aryl sulfomates with arylboronic acids [4].

In the title compound, the Pd center is coordinated by four ligands: one carbene carbon atom, one N atom from morpholine, and two chlorine atoms, giving a slightly distorted square-planar geometry. It is noted here that the H atom on the N atom of morpholine kept untouched in this case. In such structure, the NHC and the N atom are trans to each other [C1—Pd1—N3 = 169.56(9)°, Cl1—Pd1—Cl2 = 173.55(3)°].

Acknowledgements

I acknowledge the financial support from Wenzhou University for the publication fee.

References

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Received: 2018-05-06
Accepted: 2018-06-26
Published Online: 2018-07-13
Published in Print: 2018-08-28

©2018 Li Guo-Xing, published by De Gruyter, Berlin/Boston

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

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  68. Crystal structure of ethyl 2-amino-4-(3-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO6
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  71. Crystal structure of (5-ethyl-2-(4-methoxyphenyl)-1,3-dioxan-5-yl)methanol, C14H20O4
  72. Crystal structure of (E)-N-(4-bromo-2-(1-(hydroxyimino)ethyl)phenyl)benzamide, C15H13BrN2O2
  73. Crystal structure of caffeinium triiodide – caffeine (1/1), C16H21I3N8O4
  74. Crystal structure of methyl 2-methyl-4-(3-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO4
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  76. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride, C8H18N8Cl2
  77. The crystal structure of dichlorido-(1,3-bis(2,6-dimethylphenyl)-1H-imidazol-2(3H)-ylidene)-(morpholine-κ1N)palladium(II), C23H29Cl2N3OPd(II)
  78. The crystal structure of 1-((5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-yl)methyl)-1,3-diphenylurea, C24H21ClN4O
  79. Crystal structure of 6-(2-bromoacetamido)tetrahydro-2H-pyran-2,3,4,5-Tetrayl tetraacetate, C16H22BrNO10
  80. Crystal structure of 5-methylpyrazine-2-carbohydrazide, C6H8N4O
  81. Crystal structure of catena-poly[(μ2-5-(tert-butyl)isophthalato-κ4O,O′:O′′,O′′′)(-4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)manganese(II)], C32H28N4O5Mn
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