Home The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
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The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4

  • Wei Tian ORCID logo , Shuting Huang , Xinji Huang , Shijie Lin , Shaofeng Chen and Jingni Wang ORCID logo EMAIL logo
Published/Copyright: February 18, 2025

Abstract

C24H16Cl2N4O4, monoclinic, P21/n (no. 14), a = 10.2264(4) Å, b = 16.1772(6) Å, c = 13.8429(6) Å, β = 102.463(5)°, V = 2236.13(16) Å3, Z = 4, R gt (F) = 0.0574, wRref(F2) = 0.1588, T = 220(2) K.

CCDC no.: 2415848

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: clear light yellow block
Size 0.14 × 0.12 × 0.11 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 2.96 mm−1
Diffractometer, scan mode: Rigaku SuperNova, φ and ω scans
θmax, completeness: 68.2°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 8,922, 4,093, 0.041
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2,842
N(param)refined: 307
Programs: Rigaku, 1 SHELX 2 , 3 , WinGX and ORTEP 4
Table 2:

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

x y z Uiso*/Ueq
Cl1 0.38084 (12) 0.87448 (6) 0.62069 (9) 0.0675 (3)
Cl2 0.73401 (11) 0.42855 (7) 0.97656 (7) 0.0680 (3)
O1 0.0556 (3) 0.25394 (15) 0.6202 (2) 0.0581 (7)
O2 −0.1401 (2) 0.43382 (14) 0.62561 (18) 0.0419 (5)
O3 0.2594 (3) 0.26742 (15) 0.4151 (2) 0.0583 (7)
O4 0.0631 (3) 0.27878 (18) 0.2408 (2) 0.0619 (8)
N1 0.0729 (3) 0.41528 (15) 0.6032 (2) 0.0368 (6)
H1 0.132757 0.379458 0.594477 0.044*
N2 0.0999 (3) 0.49795 (15) 0.60094 (19) 0.0360 (6)
N3 0.2367 (3) 0.40537 (17) 0.4415 (2) 0.0395 (6)
H3A 0.193187 0.450932 0.423258 0.047*
N4 0.3323 (3) 0.40051 (16) 0.52807 (19) 0.0362 (6)
C1 −0.0545 (3) 0.2986 (2) 0.6280 (3) 0.0406 (7)
C2 −0.1515 (4) 0.2480 (2) 0.6438 (3) 0.0545 (10)
H2 −0.236980 0.263718 0.651862 0.065*
C3 −0.1009 (5) 0.1670 (2) 0.6462 (4) 0.0674 (12)
H3 −0.145861 0.118044 0.655707 0.081*
C4 0.0235 (5) 0.1736 (2) 0.6321 (4) 0.0707 (13)
H4 0.081358 0.128726 0.630659 0.085*
C5 −0.0469 (3) 0.3886 (2) 0.6191 (2) 0.0364 (7)
C6 0.2207 (3) 0.51796 (19) 0.5955 (2) 0.0350 (7)
C7 0.2588 (3) 0.60564 (19) 0.6004 (2) 0.0358 (7)
C8 0.3797 (3) 0.6308 (2) 0.5798 (2) 0.0396 (7)
H8 0.437031 0.591321 0.561144 0.048*
C9 0.4172 (3) 0.7135 (2) 0.5863 (3) 0.0446 (8)
H9 0.499578 0.729743 0.572515 0.053*
C10 0.3334 (4) 0.7710 (2) 0.6128 (3) 0.0482 (9)
C11 0.2119 (4) 0.7482 (2) 0.6336 (3) 0.0549 (10)
H11 0.155160 0.788235 0.651770 0.066*
C12 0.1750 (4) 0.6658 (2) 0.6274 (3) 0.0476 (9)
H12 0.092698 0.649967 0.641529 0.057*
C13 0.3284 (3) 0.45395 (18) 0.5958 (2) 0.0337 (7)
C14 0.4317 (3) 0.44784 (18) 0.6889 (2) 0.0362 (7)
C15 0.3946 (3) 0.4628 (2) 0.7782 (2) 0.0403 (7)
H15 0.306246 0.478908 0.778217 0.048*
C16 0.4862 (3) 0.4544 (2) 0.8670 (3) 0.0458 (8)
H16 0.460111 0.463138 0.927291 0.055*
C17 0.6161 (4) 0.4330 (2) 0.8660 (3) 0.0459 (8)
C18 0.6549 (3) 0.4171 (2) 0.7786 (3) 0.0479 (9)
H18 0.743608 0.401601 0.779145 0.057*
C19 0.5623 (3) 0.4242 (2) 0.6901 (3) 0.0435 (8)
H19 0.588106 0.412937 0.630259 0.052*
C20 0.2133 (3) 0.3344 (2) 0.3851 (3) 0.0418 (8)
C21 0.1278 (3) 0.3470 (2) 0.2867 (3) 0.0450 (8)
C22 0.1033 (4) 0.4128 (3) 0.2277 (3) 0.0559 (10)
H22 0.134916 0.466908 0.242567 0.067*
C23 0.0207 (5) 0.3854 (4) 0.1386 (3) 0.0772 (14)
H23 −0.010631 0.417448 0.081717 0.093*
C24 −0.0050 (4) 0.3059 (4) 0.1496 (3) 0.0738 (14)
H24 −0.061279 0.273012 0.102126 0.089*

1 Source of material

All chemicals were purchased from commercial sources and used as received without further purification. The 4,4′-dichloro benzil (1 mmol, 0.279 g), furan-2-carbohydrazide (2 mmol, 0.252 g) and diphenyltin dichloride (0.1 mmol, 0.034 g) were dissolved in MeOH (30 mL). The mixture was refluxed for 2 h. Finally, the title crystal was precipitated by controlling slowly at room temperature.

2 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).

3 Comment

Salen-like ligands are important organic ligands that are widely used because of their good coordination ability. This type of ligand can provide multiple coordination sites in the molecule and can form stable complexes with many metal ions, such as Th(IV), 5 Cu(II), 6 Zn(II), 7 and Ln(III), 8 etc. In addition, salen-like ligands also have excellent electronic and spatial effects, which can effectively regulate the activity and selectivity of reactions. Recent studies have found that organotin(IV) complexes based on salen-like ligands can kill cancer cells through multiple mechanisms of action. 9 Therefore, the synthesis and crystal structure of the title compound are important significance for the study of the application.

The asymmetric unit of the title compound is one N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2-carbohydrazide) molecule. The ORTEP diagram is presented in Figure. Bond lengths and angles are all in the expected ranges. 10 The bond length of N2=C6 and N4=C13 are 1.294(4) Å and 1.282(4) Å, respectively. Which is similar to those reported in the literature. 11 , 12 The bond length of C6–C13 is 1.511(4) Å, shorter than normal C–C single bonds, which is similar to those reported in the literature. 13


Corresponding author: Jingni Wang, College of Pharmacy, Guangxi University of Chinese Medicine, Nanning, Guangxi 530200, China, E-mail:

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

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

  3. Research funding: This work were supported by Middle-aged and Young Teachers’ Basic Ability Promotion Project of Guangxi (No.2022KY0291), Innovation Team for Research and Development of Characteristic Pharmaceutics of Zhuang & Yao Medicine (No.GZCX20231203), Natural Science Foundation General Project of Guangxi University of Chinese Medicine (No.2022MS016).

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Received: 2025-01-09
Accepted: 2025-02-05
Published Online: 2025-02-18
Published in Print: 2025-06-26

© 2025 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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