Home Crystal structure of acetonitrile{bis(2-benzimidazolylmethyl)amine-κ3N,N′,N′′}-{maleato-κO}zinc(II) perchlorate - acetonitrile (1/1), C24H24ClN7O8Zn
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Crystal structure of acetonitrile{bis(2-benzimidazolylmethyl)amine-κ3N,N′,N′′}-{maleato-κO}zinc(II) perchlorate - acetonitrile (1/1), C24H24ClN7O8Zn

  • Jiang-Li Chen , Chen Wang , Guo-Hua Su and Feng-Mei Nie EMAIL logo
Published/Copyright: April 13, 2018

Abstract

C24H24ClN7O8Zn, triclinic, P1̅ (no. 2), a = 10.0834(7) Å, b = 10.8269(7) Å, c = 13.1958(8) Å, α = 77.658(5)°, β = 77.135(5)°, γ = 87.797(5)°, V = 1371.93(15) Å3, Z = 2, Rgt(F) = 0.0410, wRref(F2) = 0.1015, T = 105.6 K.

CCDC no.: 1830650

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:Colorless block
Size:0.45 × 0.40 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.05 mm−1
Diffractometer, scan mode:Xcalibur, Eos, Gemini, ω-scans
θmax, completeness:26°, >99%
N(hkl)measured, N(hkl)unique, Rint:10264, 5393, 0.033
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4741
N(param)refined:373
Programs:CrysAlisPRO [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
Zn10.14859(3)0.38017(3)0.67765(2)0.01779(10)
Cl10.25612(7)−0.05864(6)0.60573(5)0.02569(17)
O1−0.00177(19)0.28542(17)0.64985(14)0.0216(4)
O2−0.0394(2)0.15319(18)0.80777(14)0.0237(4)
O3−0.2717(2)−0.18546(19)0.83983(15)0.0294(5)
O4−0.1556(2)−0.04996(19)0.89043(15)0.0265(5)
H4−0.12010.02010.86560.040*
O50.2475(2)−0.1631(2)0.55559(17)0.0329(5)
O60.3624(3)−0.0832(2)0.6637(2)0.0474(7)
O70.2858(3)0.0554(2)0.5274(2)0.0572(8)
O80.1315(3)−0.0478(3)0.6778(2)0.0690(9)
N10.2620(2)0.2011(2)0.73867(17)0.0190(5)
H10.22540.13250.72500.023*
N20.3098(2)0.3851(2)0.55450(17)0.0179(5)
N30.4992(2)0.2966(2)0.48200(17)0.0211(5)
H30.56900.24820.47660.025*
N40.1759(2)0.4125(2)0.81640(17)0.0194(5)
N50.2301(2)0.3425(2)0.97308(17)0.0208(5)
H50.25670.29201.02440.025*
N60.0512(2)0.5527(2)0.62466(18)0.0230(5)
N70.5607(3)0.1614(3)0.9162(2)0.0380(7)
C10.4043(3)0.2192(3)0.6786(2)0.0213(6)
H1A0.44500.13800.67140.026*
H1B0.45650.25990.71590.026*
C20.4056(3)0.3000(2)0.5709(2)0.0186(5)
C30.3455(3)0.4415(2)0.4464(2)0.0183(5)
C40.4633(3)0.3854(3)0.4002(2)0.0209(6)
C50.5213(3)0.4168(3)0.2916(2)0.0261(6)
H5A0.59890.37700.26140.031*
C60.4568(3)0.5106(3)0.2312(2)0.0279(6)
H60.49240.53490.15850.033*
C70.3397(3)0.5697(3)0.2769(2)0.0254(6)
H70.30000.63290.23380.030*
C80.2811(3)0.5365(3)0.3848(2)0.0213(6)
H80.20280.57550.41480.026*
C90.2446(3)0.1875(3)0.8543(2)0.0218(6)
H9A0.32610.15230.87630.026*
H9B0.16900.13060.89150.026*
C100.2178(3)0.3145(3)0.8808(2)0.0191(6)
C110.1590(3)0.5116(3)0.8708(2)0.0206(6)
C120.1923(3)0.4672(3)0.9703(2)0.0214(6)
C130.1843(3)0.5423(3)1.0445(2)0.0277(7)
H130.20640.51171.11000.033*
C140.1415(3)0.6657(3)1.0156(2)0.0289(7)
H140.13390.71901.06320.035*
C150.1094(3)0.7119(3)0.9164(2)0.0275(6)
H150.08140.79520.89980.033*
C160.1183(3)0.6367(3)0.8424(2)0.0227(6)
H160.09780.66820.77640.027*
C17−0.0593(3)0.1894(2)0.7151(2)0.0193(6)
C18−0.1561(3)0.1196(3)0.6756(2)0.0209(6)
H18−0.17450.15950.61050.025*
C19−0.2200(3)0.0094(3)0.7197(2)0.0219(6)
H19−0.2762−0.01540.68040.026*
C20−0.2162(3)−0.0817(3)0.8221(2)0.0227(6)
C21−0.0136(3)0.6404(3)0.6115(2)0.0211(6)
C22−0.0969(3)0.7532(3)0.5986(2)0.0264(6)
H22A−0.12500.76490.53230.040*
H22B−0.04500.82550.59900.040*
H22C−0.17580.74340.65610.040*
C230.5702(3)0.1452(3)1.0026(3)0.0293(7)
C240.5827(3)0.1229(3)1.1130(2)0.0355(7)
H24A0.67690.11271.11600.053*
H24B0.53290.04771.15260.053*
H24C0.54670.19371.14310.053*

Source of material

Bis(2-benzimidazolylmethyl)amine (bbma) was prepared according to the literature method [4]. A acetonitrile (10 mL) solution of bbma (0.069 g, 0.25 mmol) was dropped into a acetonitrile (15 mL) solution of Zn(ClO4)2⋅6H2O (0.093 g, 0.25 mmol), giving a colorless transparent solution. Then a mixture of maleic acid (H2male; 0.029 g, 0.25 mmol), 5 mL of acetonitrile and 1 mL trimethylamine (0.25 mol/L) was added dropwise. After being stirred at room temperature for 2 h, the solution was filtered and the filtrate was evaporated at room temperature. Colorless crystals suitable for X-ray structure determination formed.

Experimental details

Methyl groups were idealized and refined using rigid groups allowed to rotate about the N—C bond. The Uiso values of the hydrogen atoms of methyl groups were set to 1.5 Ueq(C) and the Uiso values of all other hydrogen atoms were set to 1.2 Ueq(C).

Discussion

Multidentate ligands containing two or more benzimidazole donor units has been studied as models for the active sites of metalloproteins [5]. Bis(2-benzimidazolylmethyl)amine (bbma) is a linear tridentate ligand with two aromatic benzimidazole side arms [6], [7], [8].

The title complex consists of a [Zn(bbma)(Hmale)(CH3CN)]+, a perchlorate and a acetonitrile solvent molecule. In the complex, the Zn(II) is five-coordinated with N4O donor sets derived from a Hmale-O atom, a acetonitrile-N atom and three bbma-N atoms. The equatorial plane is defined by two nitrogen atoms (N2, N4) of benzimidazole groups of bbma and one carboxylate O1. The distance between Zn(II) and all atoms of equatorial plan are Zn1—N2 = 2.020(2) Å, Zn1—N4 = 2.014(2) Å, Zn1—O1 = 2.0034(19) Å, and bond angles are N2—Zn1—N4 = 119.84(9)°, N2—Zn1—O1 = 107.59(8)°, N4—Zn1—O1 = 129.18(9)°. The axial positions are occupied by the N1 of bbma and N6 of acetonitrile molecule with a bond angle N1—Zn1—N6 of 176.51°, and the Zn1—N1 distance [2.299(2) Å] is longer than the bond lengths of Zn1—N6 [2.133(2) Å]. Thus, its coordination geometry is a distorted trigonal bipyramidal (tbp) and this is reflected in the index of trigonality, τ = 0.789 (τ = 0 for a perfect square pyramidal and 1 for a perfect trigonal bipyramidal geometry according to the Addison/Reedijk geometric criterion). In addition, the two benzimidazole groups of bbma can be twisted, resulting in the observation of dihedral angle of 134.21°.

In the title complex intramolecular hydrogen bonds can be observed, which derived from the O2, O4 atoms of of monodentate hydrogen maleate (HO2CCH = CHCO2) and the N1 atom of bbma (N1–H1⋯O2, O4–H4⋯O2). In addition, a double molecular unit is formed through intermolecular hydrogen bonds with type of N5–H5⋯O3, and the double molecular units are further connected via π = π interactions from benzimidazole groups of neighbouring bbma ligands to form a 2-D network.

Acknowledgements

This study was supported by Scientific Research Base Development Program of the Beijing Municipal Commission of Education.

References

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Received: 2017-11-13
Accepted: 2018-03-18
Published Online: 2018-04-13
Published in Print: 2018-07-26

©2018 Jiang-Li Chen et al., published by De Gruyter, Berlin/Boston

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

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  71. Crystal structure of 2-isopropyl-8-methyl-phenanthrene-3,4-dione, C18H16O2
  72. Crystal structure of 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione, C19H22O2
  73. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4-bromophenol, C14H13BrN2O
  74. Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2
  75. Crystal structure of bis(hydroxylamido-κ2O,N)-oxido(1H-pyrazole-3-carboxylato-κ2O,N)vanadium(V), C4H7N4O5V
  76. The crystal structure of In1.2B3O5.6(OH)1.4
  77. The crystal structure of chlorido(2-(1H-pyrazol-3-yl)phenolato-κ2N,O)(2-(1H-pyrazol-3-yl)phenol-κN)copper(II), C18H15ClCuN4O2
  78. Crystal structure of 1-heptylpyridazin-1-ium iodide, C11H19N2I
  79. The crystal structure of N-butylpyridinium bis(μ2-dichlorido)-tetrachloridodicopper(II), C18H28N2Cu2Cl6
  80. Crystal structure of 6-hydroxy-5-((2-hydroxy-6-oxocyclohex-1-en-1-yl)(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, C20H22N2O6
  81. Crystal structure of bis(acetonitrile)-diaqua-dichloridoiron(II), C4H10Cl2N2O2Fe
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