Home Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C20H24N2O2
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Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C20H24N2O2

  • Ji-Xing Zhao ORCID logo EMAIL logo and Xiao-Jun Wang
Published/Copyright: August 2, 2022

Abstract

C20H24N2O2, monoclinic, P21/c (no. 14), a = 14.5088(4) Å, b = 17.4849(6) Å, c = 7.1398(2) Å, β = 97.933(1)°, Z = 4, V = 1793.93(9) Å3, R gt (F) = 0.0561, wRref (F 2) = 0.1596, T = 173 K.

CCDC no.: 2182460

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: Yellow block
Size: 0.17 × 0.16 × 0.12 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker D8 Venture, φ and ω
θ max, completeness: 26.7°, >99%
N(hkl)measured, N(hkl)unique, R int: 22,136, 3804, 0.060
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2931
N(param)refined: 223
Programs: Bruker [1], SHELX [2], Olex2 [3]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.74657 (10) 0.40657 (9) 0.41679 (18) 0.0454 (4)
H1 0.697049 0.403520 0.464968 0.068*
O2 0.22386 (11) 0.39697 (10) 1.1559 (2) 0.0568 (4)
N1 0.57176 (11) 0.38314 (9) 0.4357 (2) 0.0372 (4)
N2 0.29675 (12) 0.40468 (10) 1.0486 (2) 0.0455 (4)
C1 0.64164 (12) 0.35625 (10) 0.1582 (2) 0.0325 (4)
C2 0.73235 (13) 0.37831 (10) 0.2389 (2) 0.0341 (4)
C3 0.80811 (13) 0.37129 (10) 0.1365 (3) 0.0361 (4)
C4 0.78927 (14) 0.34173 (11) −0.0450 (3) 0.0397 (4)
H4 0.839429 0.336261 −0.116556 0.048*
C5 0.70087 (14) 0.31965 (11) −0.1278 (3) 0.0394 (4)
H5 0.691262 0.299846 −0.252918 0.047*
C6 0.62780 (13) 0.32693 (10) −0.0260 (2) 0.0351 (4)
H6 0.567140 0.311925 −0.081123 0.042*
C7 0.90697 (14) 0.39582 (12) 0.2225 (3) 0.0447 (5)
C8 0.97701 (16) 0.38147 (17) 0.0841 (4) 0.0671 (7)
H8A 0.980077 0.326557 0.058200 0.101*
H8B 1.038589 0.399738 0.139828 0.101*
H8C 0.957158 0.408951 −0.034239 0.101*
C9 0.93871 (17) 0.35127 (16) 0.4048 (4) 0.0708 (8)
H9A 0.895691 0.361136 0.496432 0.106*
H9B 1.001466 0.367753 0.457863 0.106*
H9C 0.939287 0.296427 0.376640 0.106*
C10 0.90749 (16) 0.48186 (13) 0.2625 (3) 0.0517 (5)
H10A 0.887671 0.509639 0.144589 0.078*
H10B 0.970507 0.497936 0.314869 0.078*
H10C 0.864627 0.493076 0.353633 0.078*
C11 0.56341 (13) 0.35987 (10) 0.2632 (3) 0.0350 (4)
H11 0.503809 0.344552 0.202850 0.042*
C12 0.49559 (13) 0.37883 (11) 0.5395 (2) 0.0360 (4)
C13 0.43126 (13) 0.31923 (11) 0.5175 (3) 0.0382 (4)
H13 0.435680 0.280902 0.424799 0.046*
C14 0.36091 (13) 0.31561 (11) 0.6300 (3) 0.0385 (4)
H14 0.317534 0.274644 0.613635 0.046*
C15 0.35271 (13) 0.37112 (11) 0.7668 (2) 0.0366 (4)
C16 0.41728 (14) 0.43105 (11) 0.7868 (3) 0.0388 (4)
H16 0.411939 0.470133 0.877078 0.047*
C17 0.48842 (14) 0.43432 (11) 0.6777 (3) 0.0387 (4)
H17 0.532832 0.474479 0.696513 0.046*
C18 0.27859 (14) 0.36598 (12) 0.8893 (3) 0.0411 (4)
C19 0.19332 (15) 0.31972 (14) 0.8270 (3) 0.0534 (6)
H19A 0.209726 0.265342 0.827611 0.080*
H19B 0.166720 0.335030 0.698833 0.080*
H19C 0.147561 0.328437 0.913669 0.080*
C20 0.23956 (17) 0.45378 (15) 1.3014 (3) 0.0563 (6)
H20A 0.233895 0.504812 1.244175 0.084*
H20B 0.302157 0.447435 1.371120 0.084*
H20C 0.193350 0.447962 1.388361 0.084*

Source of material

All chemicals were used without further purification. 1-(4–Aminophenyl)ethan-1-one O-methyl oxime was prepared by a reported method [4]. 3-tert–Butyl-2-hydroxy-benzaldehyde (178.26 mg, 1 mmol) dissolved in ethanol (5 mL) was added to 1-(4-aminophenyl)ethan-1-one O-methyl oxime (164.20 mg, 1 mmol) dissolved in ethanol (5 mL) at 338 K. The mixture was kept stirring for 5 h, then cooled to room temperature and filtered. The filtrate was allowed to stand for 10 days in a quiet environment. Several clear light yellow crystals were obtained.

Experimental details

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

Comment

The synthesis and crystal structure of Schiff bases and their derivatives have attracted much attention because they have shown great application value in various fields [5, 6]. For example, Schiff base compounds can form complexes with transition metals, which can be used in the research of fluorescent materials [7, 8], ion recognition [9] and so on. We will continue to investigated the synthesis and characterization of transition metal complexes of the title compounds [10, 11].

The single crystal structure of the title compound is shown in Figure 1 (cf. the figure). It is only built up by the C20H24N2O2 molecules. Comparison with reported similar structures, showed that all bond lengths and bond angles are within the normal ranges [4]. In the title compound, there is a strong intramolecular O1—H1⃛N1 hydrogen bond interaction (d(N1⃛H1)=1.836 Å, d(O1—H1)=0.840 Å and d(O1⃛N1)=2.591 Å).


Corresponding author: Ji-Xing Zhao, Analysis and Testing Center, Shihezi University, Xinjiang 832003, P. R. China, E-mail:

Funding source: Shihezi University

Award Identifier / Grant number: ZZZC2021117

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This project was supported by the Open Project Program of Shihezi University (ZZZC2021117).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2022-06-05
Accepted: 2022-06-28
Published Online: 2022-08-02
Published in Print: 2022-10-26

© 2022 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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