Home Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
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Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6

  • Zong-Li Ren , Lan Wang , Ling-Zhi Liu , Xiang-Qian Li and Wen-Kui Dong EMAIL logo
Published/Copyright: September 1, 2018

Abstract

C20H24N2O6, triclinic, P1̄, a = 7.1389(5) Å, b = 9.4977(7) Å, c = 14.6456(10) Å, α = 105.118(3)°, β = 101.188(2)°, γ = 94.739(3)°, Z = 2, V = 931.08(11) Å3, Rgt(F) = 0.0564, wRref(F2) = 0.1646, T = 153(2) K.

CCDC no.: 1852831

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:

Crystal collection and handling.

Crystal:Needle, colorless
Size:0.26 × 0.23 × 0.19 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:0.103 mm−1
Diffractometer, scan mode:Bruker APEX-II, Φ and ω-scans
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:6634, 3266, 0.0627
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2482
N(param)refined:259
Programs:Bruker programs [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.8863(2)−0.1158(2)0.77513(11)0.0276(4)
O20.9624(2)0.23875(18)0.60326(11)0.0231(4)
H20.9305300.2501920.5476360.035
O30.7360(2)0.19814(19)0.33417(10)0.0236(4)
O40.5344(2)0.46846(19)0.34970(11)0.0275(4)
O50.7408(2)0.63313(19)0.16622(11)0.0255(4)
H50.7278860.5972990.2117280.038
O60.3785(2)0.7898(2)−0.08836(11)0.0330(5)
N10.7830(2)0.1708(2)0.42553(12)0.0198(5)
N20.5514(3)0.5304(2)0.27345(13)0.0241(5)
C11.0205(4)−0.0199(3)0.85784(17)0.0340(7)
H1A1.144195−0.0006370.8405870.051
H1B1.039244−0.0664920.9106480.051
H1C0.9701530.0732480.8789460.051
C20.8514(3)−0.0694(3)0.69363(16)0.0210(5)
C30.9261(3)0.0668(3)0.68938(15)0.0195(5)
H31.0062820.1352600.7454580.023
C40.8829(3)0.1033(3)0.60217(15)0.0180(5)
C50.7650(3)0.0039(3)0.51769(15)0.0177(5)
C60.6914(3)−0.1326(3)0.52569(16)0.0197(5)
H60.610902−0.2017600.4700580.024
C70.7318(3)−0.1700(3)0.61134(16)0.0222(5)
H70.679006−0.2632060.6146230.027
C80.7189(3)0.0390(3)0.42403(15)0.0171(5)
C90.6063(3)−0.0749(3)0.33521(15)0.0221(5)
H9A0.605523−0.0385920.2783780.033
H9B0.473511−0.0955570.3417950.033
H9C0.665763−0.1654440.3271160.033
C100.8222(3)0.3443(3)0.34477(17)0.0261(6)
H10A0.8175830.3574690.2795380.031
H10B0.9594790.3571260.3784190.031
C110.7255(3)0.4612(3)0.40045(16)0.0265(6)
H11A0.7182760.4421120.4630630.032
H11B0.8054820.5579740.4149430.032
C120.3873(3)0.5424(3)0.22381(16)0.0216(5)
C130.1995(3)0.4949(3)0.24579(18)0.0302(6)
H13A0.1907290.3908280.2443450.045
H13B0.0925710.5083880.1970810.045
H13C0.1924690.5545900.3103130.045
C140.3923(3)0.6079(3)0.14311(15)0.0210(5)
C150.5656(3)0.6495(3)0.11834(16)0.0208(5)
C160.5653(3)0.7108(3)0.04174(16)0.0233(5)
H160.6836460.7388110.0263960.028
C170.3938(3)0.7310(3)−0.01182(16)0.0250(6)
C180.2203(3)0.6902(3)0.01058(17)0.0288(6)
H180.1017780.703305−0.0266710.035
C190.2209(3)0.6309(3)0.08677(17)0.0255(6)
H190.1016280.6045960.1017960.031
C200.5523(4)0.8415(3)−0.11097(18)0.0334(7)
H20A0.6268860.921359−0.0556300.050
H20B0.5208900.878210−0.1679610.050
H20C0.6286610.760549−0.1248460.050

Source of materials

A solution of 1,2-bis(aminooxy)ethane (92.1 mg, 1.00 mmol) in ethanol solution (5 mL) was added gradually to a solution of 2-hydroxy-4-methoxy-1-acetophenone (332.34 mg, 2.00 mmol) in ethanol (15 mL), and the mixture was stirred for 24 h at 333 K. After cooling to room temperature, the mixture was filtered and the precipitate was washed successively with absolute ethanol and a mixture of n-hexane and absolute ethanol in the ratio 4:1, respectively. The crude product was purified by recrystallization with ethanol and the title compound was obtained (260.07 mg, 67%). A solution of the title compound in acetone and absolute ethanol was allowed to stand at room temperature for several days, resulting in clear light colorless crystals; M.p. 413–414 K. Elemental analysis – Anal. Calcd. for C20H24N2O6: C, 61.85%; H, 6.23%; N, 7.21%. Found: C, 62.05%; H, 6.21%; N, 7.19%.

Experimental details

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

Discussion

It is well known that Salen-like compounds have been widely investigated in modern coordination chemistry and organometallic chemistry [4], [5], [6]. They are able to form different types of metal complexes with interesting properties [7], [8], [9]. These compounds can be applied to luminescent [10] and magnetic [11] materials, catalytic activities [12] and supramolecular building units [13].

The title compound is only built up by the C20H24N2O6 molecules, in which all bond lengths are within the normal ranges (cf. the figure). The molecule adopts an E configuration with respect to each azomethine C=N bond. The imino group is coplanar with the aromatic ring. Within the molecule, the planar units aren’t parallel, and extend in opposite directions from the dimethylene bridge. In the crystal structure, there are intramolecular hydrogen bond interactions (O2—H2⋯N1, O5—H5⋯N2) and weak non-classical intermolecular hydrogen bond interactions [15], [16].

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Received: 2018-07-12
Accepted: 2018-08-15
Published Online: 2018-09-01
Published in Print: 2018-11-27

©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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