Home Physical Sciences The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
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The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12

  • Miao Cheng and Shuang Cheng EMAIL logo
Published/Copyright: September 18, 2019

Abstract

C36H58Cl2CuN12, monoclinic, P21/c (no. 14), a = 8.1490(8) Å, b = 17.0301(15) Å, c = 16.8649(14) Å, β = 101.629(3)°, Z = 2, V = 2292.4(4) Å3, Rgt(F) = 0.0419, wRref(F2) = 0.1121, T = 298(2) K.

CCDC no.: 1946284

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Blue block
Size:0.22 × 0.20 × 0.18 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.63 mm−1
Diffractometer, scan mode:Bruker SMART APEX-II, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:11331, 4033, 0.033
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2846
N(param)refined:237
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Cu11.0000000.5000000.5000000.04109(17)
N11.1122(3)0.40773(12)0.45637(13)0.0382(5)
N21.2519(3)0.29984(13)0.44242(14)0.0471(6)
N31.1256(3)0.57126(12)0.43537(13)0.0379(5)
N41.1845(4)0.66314(15)0.35461(18)0.0675(8)
N50.7534(3)0.48437(14)0.37788(16)0.0541(6)
N60.5542(3)0.47905(14)0.26673(15)0.0524(6)
Cl10.32382(9)0.23645(4)0.19130(5)0.0532(2)
C11.1986(4)0.34863(16)0.49401(17)0.0458(7)
H11.2201010.3416300.5498380.055*
C21.1121(4)0.39567(16)0.37589(16)0.0430(7)
H21.0605610.4282270.3339240.052*
C31.1975(4)0.32984(17)0.36664(17)0.0479(7)
H31.2159090.3089260.3182340.057*
C41.3401(4)0.22448(17)0.4658(2)0.0628(9)
H41.3681610.2222480.5250180.075*
C51.4997(5)0.2206(2)0.4357(3)0.0882(13)
H5A1.4755830.2221690.3775900.132*
H5B1.5571500.1726600.4537320.132*
H5C1.5691320.2645300.4563480.132*
C61.2233(6)0.1580(2)0.4369(4)0.126(2)
H6A1.1962000.1579730.3788040.188*
H6B1.1226090.1641960.4575900.188*
H6C1.2761700.1092560.4557890.188*
C71.0658(4)0.62744(18)0.38461(19)0.0553(8)
H70.9529670.6407570.3711470.066*
C81.2944(4)0.57080(18)0.43694(18)0.0499(7)
H81.3713610.5364610.4670470.060*
C91.3312(4)0.62759(19)0.3883(2)0.0618(9)
H91.4370190.6402340.3793570.074*
C101.1586(8)0.7298(2)0.2958(3)0.128(2)
H101.0361380.7268780.2813020.154*
C111.1902(6)0.7117(3)0.2199(3)0.1009(15)
H11A1.2234580.7509480.1881200.121*
H11B1.1780970.6603550.2008230.121*
C121.1694(7)0.8027(2)0.3353(3)0.1176(19)
H12A1.2839250.8130550.3602810.176*
H12B1.1022370.8016690.3759680.176*
H12C1.1293150.8431940.2966420.176*
C130.6668(4)0.52378(18)0.3171(2)0.0546(8)
H130.6811250.5771990.3093190.065*
C140.6929(4)0.40928(18)0.36523(19)0.0548(8)
H140.7307870.3668830.3987010.066*
C150.5720(4)0.40487(17)0.29829(19)0.0538(8)
H150.5123990.3603340.2775720.065*
C160.4399(5)0.5047(2)0.1929(2)0.0698(10)
H160.4482180.5619580.1899380.084*
C170.4935(7)0.4708(3)0.1191(2)0.1114(17)
H17A0.6074400.4855510.1195010.167*
H17B0.4222400.4908930.0709850.167*
H17C0.4849380.4146370.1198780.167*
C180.2604(5)0.4849(3)0.1955(3)0.1006(15)
H18A0.2450790.4289920.1916100.151*
H18B0.1870120.5097910.1509070.151*
H18C0.2350790.5031760.2454690.151*

Source of material

In a 25 mL round-bottom flask, N-isopropylimidazole (1.102 g; 10 mmol), and copper(II) chloride dihydrate (0.341 g; 2 mmol), molybdenyl acetylacetonate (0.328 g; 1 mmol) and 15 mL water were added successively. The mixture was heated to 80 °C for 6 h, resulting in a blue solution. The mixture was filtrated and the filtrate stood by slow evaporation for seven days. Crystals of the title complex were obtained.

Yield: 52% (based on Cu element), and elemental analysis: calc. for C36H58Cl2CuN12: C 54.50, H 7.37, N 21.19; found: C 54.55, H 7.24, N 21.24 (PERKIN ELMER MODEL 2400 SERIES II).

Experimental details

All hydrogen atoms were refined with variable isotropic displacement parameters. Hydrogen atoms were assigned with common isotropic displacement factors Uiso(H) = 1.5 times Ueq (C, methyl) and Uiso(H) = 1.2 times Ueq (C, imidazole and methylene). All the H atoms were refined as riding on their parent atom.

Comment

Copper complexes are a class which have been widely used in gas storage and separation and catalysis [3], [4], [5]. The design of new copper complexes not only expands our understanding of structure and bonding but also extends the range of copper-inspired materials [6], [7]. So far, a variety of organic-inorganic hybrids containing copper complexes have been demonstrated [8]. In addition, as a class of versatile N-ligands, imidazole derivatives can be used not only as a solvent but also as a ligand in the synthesis of metal complexes [9], [10]. However, to the best of our knowledge, examples of imidazole-copper complexes of organic-inorganic hybrids are still rare.

The molecular structure of the title complex is shown in the figure. The title complex contains six N-isopropylimidazole ligands, one copper cation and two free chlorine anions. The copper cation adopts a distorted octahedron geometry and is located on an inversion center. The four short Cu—N distances in the equatorial plane; Cu—N(1) is 2.029(2) Å and the Cu—N(3) is 2.039(2) Å, are comparable to inner sphere Cu—N distances found in the hexakis (N-methylimidazole) copper(II) salicylate complexes [11]. The two long distances Cu—N(5) and Cu—N(5A) in the complex are 2.585(3) Å, which are similar with those reported for hexakis(1-(4-cyanophenyl)imidazole-N3)-copper(II) diperchlorate [12]. The bond angles around the copper(II) ion are N(1)—Cu(1)—N(3) (89.95(8)°), N(1)—Cu(1)—N(5) (94.22(8)°), N(3)—Cu(1)—N(5) (91.45(8)°), which are similar with those of bis(4,5-dicyano-1H-imidazol-1-yl)-tetrakis(1-methyl-1H-imidazole)copper(II) [13] and a more complex material [14].

Funding source: Research on Experimental Technology of Liaocheng University

Award Identifier / Grant number: 38622170214

Funding statement: We gratefully acknowledge support by the Research on Experimental Technology of Liaocheng University (38622170214).

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Received: 2019-06-25
Accepted: 2019-08-09
Published Online: 2019-09-18
Published in Print: 2019-12-18

©2019 Miao Cheng 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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  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
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