Home Physical Sciences The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
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The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2

  • Zhenxiu Xiao , Xin Deng , Wujiu Jiang ORCID logo EMAIL logo and Weiwei Fu EMAIL logo
Published/Copyright: January 31, 2023

Abstract

C22H28N2O2, monoclinic, P21/n (no. 14), a = 6.463(3) Å, b = 14.889(6) Å, c = 10.282(4) Å, β = 95.105(5)°, V = 985.5(7) Å3, Z = 2, Rgt(F) = 0.0425, wRref(F2) = 0.1206, T = 296 (2) K.

CCDC no.: 2234957

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: 0.25 × 0.21 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 28.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 13,105, 2508, 0.025
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1959
N(param)refined: 122
Programs: Bruker [1], SHELX [2, 3], WinGX/ORTEP [4]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.32721 (13) 0.33248 (6) 0.52928 (9) 0.0437 (2)
H1 0.233780 0.367693 0.542469 0.066*
N1 0.08212 (14) 0.47077 (6) 0.49154 (10) 0.0370 (2)
C3 0.60507 (16) 0.31430 (7) 0.39484 (11) 0.0314 (2)
C1 0.37136 (16) 0.44380 (7) 0.36702 (11) 0.0320 (3)
C2 0.43330 (16) 0.36373 (7) 0.43129 (10) 0.0304 (2)
C7 0.19394 (17) 0.49513 (8) 0.40109 (12) 0.0359 (3)
H7 0.159847 0.547821 0.355551 0.043*
C8 0.67135 (17) 0.22620 (8) 0.46335 (12) 0.0371 (3)
C4 0.70954 (18) 0.34987 (9) 0.29467 (12) 0.0395 (3)
H4 0.823625 0.318796 0.268569 0.047*
C6 0.48416 (19) 0.47604 (8) 0.26719 (12) 0.0408 (3)
H6 0.444742 0.529366 0.224868 0.049*
C5 0.6523 (2) 0.42951 (9) 0.23146 (13) 0.0450 (3)
H5 0.727798 0.451109 0.165200 0.054*
C10 0.7360 (2) 0.24395 (10) 0.60788 (13) 0.0506 (4)
H10A 0.857719 0.281206 0.615830 0.076*
H10B 0.765833 0.187932 0.651858 0.076*
H10C 0.625082 0.273838 0.646615 0.076*
C9 0.4936 (2) 0.15785 (10) 0.44909 (16) 0.0557 (4)
H9A 0.376065 0.181234 0.488965 0.084*
H9B 0.537955 0.102716 0.491216 0.084*
H9C 0.455321 0.146774 0.358144 0.084*
C11 0.8584 (2) 0.18416 (10) 0.40505 (15) 0.0553 (4)
H11A 0.823000 0.171400 0.314277 0.083*
H11B 0.896424 0.129441 0.450450 0.083*
H11C 0.973243 0.225282 0.413842 0.083*

Source of material

All chemicals were purchased from commercial sources and used as received. The 3-(tert-butyl)-2-hydroxybenzaldehyde (20 mmol, 3.564 g) and hydrazine hydrate (10 mmol, 0.5 g) were dissolved in MeOH (100 mL). The mixture was refluxed for 4 h. Finally, the title crystal was precipitated by controlling slowly cooling.

Experimental details

All H-atoms bonded to C atoms were placed geometrically and refined using a riding model with common isotropic displacement factors Uiso(H) = 1.2 or 1.5 Ueq (parent C-atom).

Comment

Schiff bases have found widespread use in many disciplines. In the field of coordination chemistry, Schiff bases are important organic ligands [5, 6]. Salicylaldehyde azine is a special class of Schiff bases with fluorescent properties which have important applications in the field of bioassays [7, 8], in general, the fluorescence intensity can be significantly enhanced by connecting large steric hindrance electron donor substituents to salicylaldehyde azine. So, the synthesis and crystal structure of new Schiff bases is of great significance.

The title molecule in the crystal structure is a symmetric molecule. The ORTEP diagram is presented in the Figure. Bond lengths and angles are all in the expected ranges. The title molecule exhibits an E configuration. The bond length of C7=N1 is 1.2800(15) Å, which is similar to those reported in the literature [9], [10], [11], [12]. The bond length of C1–C7 is 1.4468(15) Å which is similar to those reported in the literature [13], [14], [15].

Intramolecular hydrogen bonding exist in the crystal structure of the title compound. The oxygen atom O1 provides one intramolecular hydrogen bond to N1 (O1⋯N1 = 2.6056(14) Å).


Corresponding author: Wujiu Jiang and Weiwei Fu, School of Chemistry and Materials Science, Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Metal Organic New Materials of College of Hunan Province, Hengyang Normal University, Hengyang, Hunan 421008, China, E-mail: ,

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

  2. Research funding: This work was supported by the 2022 Innovation and Entrepreneurship Training Program for Hunan College students (No. NYD202211), the 22nd College students Extracurricular Academic Science and Technology Works Competition Project of Henyang Normal University (No. 14), Hunan Provincial Natural Science Foundation of China (No. 2022JJ30096), the Innovation Platform Open Fund Project of Hunan Provincial Education Department of China (No. 20K016) and Foundation of Key Laboratory of Functional Metal-Organic Compounds of Hunan Province (No. 2022HSKFJJ028).

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

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Received: 2023-01-07
Accepted: 2023-01-20
Published Online: 2023-01-31
Published in Print: 2023-04-25

© 2023 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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