Home The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
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The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4

  • Fuguang Liao , Shuhao Yuan , Weifeng Nie , Zirong Yi , Qian Zhang , Shiyu Yan and Ying Cui ORCID logo EMAIL logo
Published/Copyright: May 5, 2023

Abstract

C20H14N4, monoclinic, P21/c (no. 14), a = 13.4569(16) Å, b = 4.7592(5) Å, c = 11.9902(13) Å, β = 94.914(2)°, V = 765.08(15) Å3, Z = 2, R gt (F) = 0.0333, wR ref (F 2) = 0.0935, T = 296(2) K.

CCDC no.: 2235011

The molecular structure is shown in the figure. 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: 0.23 × 0.18 × 0.18 mm
Wavelength: Mo radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 26.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 4014, 1491, 0.017
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1214
N(param)refined: 110
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 U iso*/U eq
N1 0.71688 (7) 0.5785 (2) 0.53794 (7) 0.0351 (3)
N2 0.51847 (7) 0.0952 (2) 0.54198 (7) 0.0368 (3)
C1 0.64312 (8) 0.4502 (2) 0.58372 (9) 0.0321 (3)
C4 0.75029 (8) 0.8437 (2) 0.71160 (9) 0.0339 (3)
C9 0.77066 (8) 0.7750 (2) 0.60048 (9) 0.0336 (3)
C10 0.59112 (8) 0.2385 (2) 0.51166 (9) 0.0353 (3)
H10 0.612165 0.207885 0.440790 0.042*
C3 0.66924 (9) 0.7056 (3) 0.75539 (9) 0.0371 (3)
H3 0.652446 0.748054 0.827127 0.044*
C2 0.61578 (8) 0.5109 (3) 0.69284 (9) 0.0358 (3)
H2 0.562270 0.419177 0.721018 0.043*
C5 0.81048 (9) 1.0461 (3) 0.77144 (10) 0.0431 (3)
H5 0.798401 1.091122 0.844537 0.052*
C8 0.84903 (9) 0.9154 (3) 0.55226 (11) 0.0448 (3)
H8 0.862562 0.873956 0.479291 0.054*
C6 0.88603 (9) 1.1756 (3) 0.72277 (12) 0.0504 (4)
H6 0.925425 1.307545 0.763066 0.061*
C7 0.90491 (9) 1.1114 (3) 0.61222 (12) 0.0514 (4)
H7 0.956029 1.203573 0.579571 0.062*

1 Source of material

All chemicals were purchased from commercial sources and used as received without further purification. The quinoline-2-carbaldehyde (20 mmol, 3.141 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.

2 Experimental details

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

3 Comment

The Schiff bases of quinoline have important applications in metal ion detection, biological detection and fluorescence analysis [5], [6], [7]. 1,2–Bis(quinolin-2-ylmethylene)hydrazine belongs to a special class of Schiff bases with fluorescent properties which have important applications in the field of mercury ion detection [8]. So, the crystal structure of the title compound is of great significance to studying the application.

Single-crystal structure analysis revealed that the title compound crystallized in the monoclinic space group P21/c. The title molecule in the crystal structure owns inversion symmetry. Bond lengths and angles are all in the expected ranges. The title molecule exhibits an E configuration. The bond length of C10=N2 is 1.2706(14) Å, which is similar to those reported in the literature [912]. The bond length of C1–C10 is 1.4654(15) Å, which is shorter than normal C–C single bonds (1.54 Å), but is similar to those reported in the literature [8, 13].


Corresponding author: Ying Cui, School of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China, E-mail:

Funding source: Science Foundation of Hengyang Normal University of China

Award Identifier / Grant number: 2021QD03

Funding source: Hengyang Normal University Industrial Supported Project

Award Identifier / Grant number: HXKY202127

Funding source: Foundation of Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of Xiangjiang River

Award Identifier / Grant number: 2021HSKFJJ027

  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 Science Foundation of Hengyang Normal University of China (No. 2021QD03), Hengyang Normal University Industrial Supported Project (No. HXKY202127), and Foundation of Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of Xiangjiang River (No. 2021HSKFJJ027).

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

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Received: 2023-02-23
Accepted: 2023-03-14
Published Online: 2023-05-05
Published in Print: 2023-08-28

© 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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