Home Synthesis and crystal structure of 2,2′-ethylenedioxybis(benzimide)-2,2′-bis[O-(1-propyloxyamide)]oxime-4,4′,6,6′-tetrachlorodiphenol, C36H34Cl4N4O8
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Synthesis and crystal structure of 2,2′-ethylenedioxybis(benzimide)-2,2′-bis[O-(1-propyloxyamide)]oxime-4,4′,6,6′-tetrachlorodiphenol, C36H34Cl4N4O8

  • Zong-Li Ren , Zhi-Li Wei , Lan Wang , Jian-Chun Ma and Wen-Kui Dong EMAIL logo
Published/Copyright: June 13, 2018

Abstract

C36H34Cl4N4O8, monoclinic, C2/c (no. 15), a = 33.048(10) Å, b = 6.4688(7) Å, c = 24.301(7) Å, β = 133.30(5)°, Z = 4, V = 3781(3) Å3, Rgt(F) = 0.0477, wRref(F2) = 0.1016, T = 293(2) K.

CCDC no.: 1811864

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:Clear light green needle
Size:0.26 × 0.22 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.37 mm−1
Diffractometer, scan mode:SuperNova, dual, ω scans
θmax, completeness:26.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:8189, 3701, 0.012
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2195
N(param)refined:235
Programs:CrysAlisPRO [1], SHELX [2], Olex2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.15219(11)1.4807(4)0.59708(13)0.0671(7)
C20.16715(11)1.6609(4)0.58401(13)0.0706(8)
C30.12762(11)1.7811(4)0.52123(13)0.0700(8)
H30.1380401.9021540.5130840.084*
C40.07230(11)1.7207(4)0.47035(13)0.0686(7)
C50.05695(11)1.5413(4)0.48281(13)0.0661(7)
H50.0198191.5012230.4487300.079*
C60.09656(11)1.4208(4)0.54577(13)0.0654(7)
C70.07855(11)1.2414(4)0.55704(13)0.0686(7)
H70.0413981.2018440.5209720.082*
C80.12879(11)0.8751(4)0.68994(14)0.0734(8)
H8A0.1428450.9728040.7299360.088*
H8B0.1596980.8228440.6972260.088*
C90.09822(12)0.7004(4)0.68934(14)0.0721(8)
H9A0.0681620.7553680.6835250.086*
H9B0.0823490.6090060.6470630.086*
C100.13741(12)0.5838(4)0.76117(14)0.0795(9)
H10A0.1672180.5240090.7673120.095*
H10B0.1533180.6721910.8041550.095*
C110.11024(11)0.1593(4)0.81554(14)0.0667(7)
H110.0731140.1387630.7717190.080*
C120.13708(11)0.0218(4)0.87881(13)0.0628(7)
C130.19006(11)0.0630(4)0.94719(13)0.0701(8)
H130.2082700.1820560.9525570.084*
C140.21584(12)−0.0674(4)1.00646(15)0.0823(9)
H140.251862−0.0391851.0517510.099*
C150.18842(12)−0.2452(4)0.99986(15)0.0772(8)
H150.205713−0.3332071.0409480.093*
C160.13548(11)−0.2879(4)0.93168(14)0.0703(7)
H160.117310−0.4066120.9267040.084*
C170.10915(11)−0.1557(4)0.87061(13)0.0638(7)
C180.02580(10)−0.3597(3)0.78907(13)0.0684(7)
H18A0.046015−0.4867720.8010130.082*
H18B0.018632−0.3495080.8215790.082*
Cl10.02396(3)1.86723(10)0.39303(4)0.0821(3)
Cl20.23595(3)1.73453(10)0.64494(3)0.0831(3)
N10.11391(10)1.1325(3)0.61766(11)0.0703(6)
N20.13647(9)0.3057(3)0.81918(11)0.0692(6)
O10.19343(8)1.3770(3)0.66015(9)0.0780(6)
H1B0.1848421.2564100.6711460.094*
O20.08888(8)0.9685(3)0.61861(9)0.0751(5)
O30.10232(8)0.4216(2)0.75305(9)0.0739(5)
O40.05793(7)−0.1844(2)0.80077(9)0.0692(5)

Source of material

2,2′-(Ethylenedioxy)bisbenzaldehyde was prepared according to a literature procedure [4]; 1,3-bis(aminooxy)propane and 2-[O-(1-propyloxyamide)]oxime-4,6-dichlorophenol were synthesized according to a reported method [5], [6]. 2-[O-(1-propyloxyamide)]oxime-4,6-dichlorophenol (114.0 mg, 0.60 mmol) in ethanol (10 mL) was added slowly to a solution of 1,3-bis(aminooxy)propane (46.0 mg, 0.43 mmol) in ethanol (10 mL), and was stirred for 6 h at 60 °C. After cooling to room temperature, the product was distilled under reduced pressure. The solution of the product (116.0 mg, 0.43 mmol) in ethanol (10 mL) was added slowly to a solution of 2,2′-(ethylenedioxy)bis(benzaldehyde) (240.0 mg, 0.86 mmol) in ethanol (10 mL), and stirred for 6 h at the same temperature. Precipitates were collected on a suction filter to afford the title compound (286.0 mg, 80.3%). The solution of the title compound in acetone and ethanol was allowed to stand at room temperature for several days, resulting in light green crystals; m.p. 130–131 °C. Elemental analysis: Anal. Calcd. for C36H34Cl4N4O8: C, 53.00%; H, 4.71%; N, 7.27%. Found: C, 53.33%; H, 4.85%; N, 7.05%.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Discussion

Salamo-type compounds have drawn much attention in the recent years because these compounds can accommodate one, two or more metal centers and form homo- and heteronuclear metal complexes with interesting properties [7], [8], [9]. In addition, they can be used to obtain non-linear optical materials, models of biological systems, magnetic properties, and are building blocks for supramolecular structures [10], [11], [12], [13], [14]. The crystal structure of the title compound was determined by X-ray crystallography (cf. the figure). The crystal structure of the title compound is only built up by C2 symmetrical molecule, in which all bond lengths are in normal ranges. There is one intramolecular hydrogen bond (O1—H1B⋯N1) [15], [16].

References

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Received: 2018-02-05
Accepted: 2018-05-29
Published Online: 2018-06-13
Published in Print: 2018-08-28

©2018 Zong-Li Ren 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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  75. Crystal structure of (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H28O2
  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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