Home Crystal structure of N′,N‴-((1E,1′E)-((decane-1,10-diylbis(oxy))bis(2,1-phenylene)) bis(methaneylylidene))di(isonicotinohydrazide), C36H40N6O4
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Crystal structure of N′,N‴-((1E,1′E)-((decane-1,10-diylbis(oxy))bis(2,1-phenylene)) bis(methaneylylidene))di(isonicotinohydrazide), C36H40N6O4

  • Ying Xiong ORCID logo EMAIL logo and Chuan Gao
Published/Copyright: May 11, 2021

Abstract

C36H40N6O4, monoclinic, P21/c (no. 14), a = 11.094(6) Å, b = 17.694(11) Å, c = 8.698(5) Å, β = 103.56(2)°, V = 1659.9(16) Å3, Z = 2, Rgt(F) = 0.0470, wRref(F2) = 0.1375, T = 273 K.

CCDC no.: 2060577

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:Colourless block
Size:0.25 × 0.22 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.08 mm−1
Diffractometer, scan mode:D8/APEX2, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:30844, 2926, 0.081
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1983
N(param)refined:208
Programs:Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.0084 (2)0.16008 (15)0.1557 (4)0.0806 (8)
H1−0.0712390.1630790.0911780.097*
C20.1064 (2)0.18228 (13)0.0925 (3)0.0678 (6)
H2A0.0927710.197627−0.0123840.081*
C30.22485 (19)0.18116 (11)0.1887 (2)0.0516 (5)
C40.2390 (2)0.15567 (12)0.3411 (3)0.0600 (6)
H40.3170660.1539340.4097520.072*
C50.1352 (3)0.13264 (14)0.3908 (3)0.0776 (7)
H50.1465140.1143680.4933950.093*
C60.33254 (19)0.20559 (11)0.1242 (2)0.0512 (5)
C70.58877 (19)0.31823 (12)0.2782 (2)0.0532 (5)
H70.5649440.3304390.3708330.064*
C80.70311 (18)0.35032 (12)0.2499 (2)0.0537 (5)
C90.7602 (2)0.32037 (14)0.1379 (3)0.0697 (7)
H90.7269540.2777610.0807860.084*
C100.8667 (2)0.35349 (17)0.1101 (3)0.0820 (8)
H100.9043850.3332500.0344480.098*
C110.9159 (2)0.41611 (17)0.1946 (3)0.0785 (7)
H110.9869510.4382670.1753260.094*
C120.8623 (2)0.44654 (14)0.3070 (3)0.0696 (6)
H120.8967640.4889460.3638110.084*
C130.75605 (18)0.41364 (13)0.3356 (2)0.0562 (5)
C140.7509 (2)0.49630 (13)0.5546 (3)0.0657 (6)
H14A0.7609500.5433010.5015210.079*
H14B0.8318190.4793800.6132800.079*
C150.6654 (2)0.50723 (13)0.6638 (3)0.0664 (6)
H15A0.5848050.5232970.6024620.080*
H15B0.6978940.5470810.7386370.080*
C160.6498 (3)0.43612 (13)0.7540 (3)0.0762 (7)
H16A0.7261710.4267690.8325360.091*
H16B0.6366210.3938410.6809620.091*
C170.5431 (2)0.43894 (14)0.8367 (3)0.0741 (7)
H17A0.4661420.4446680.7571770.089*
H17B0.5394450.3909760.8894360.089*
C180.5515 (2)0.50107 (13)0.9557 (3)0.0657 (6)
H18A0.5488210.5493110.9020340.079*
H18B0.6308320.4975921.0315720.079*
N10.0205 (2)0.13490 (13)0.3016 (3)0.0849 (7)
N20.41619 (15)0.24825 (9)0.22356 (19)0.0526 (4)
H20.4047750.2597110.3151750.063*
N30.52103 (15)0.27385 (10)0.1786 (2)0.0544 (4)
O10.33980 (14)0.18754 (8)−0.00953 (17)0.0646 (4)
O20.69441 (14)0.44041 (9)0.44244 (18)0.0718 (5)

Source of material

A solution of 2,2′-(decane-1,10-diylbis(oxy))dibenzaldehyde (0.76 g, 2.0 mmol) in ethanol (50 mL) was added to a stirred ethanol solution (50 mL) of isonicotinohydrazide (0.55 g, 4.0 mmol). The reaction mixture was refluxed for 8 h, then the mixture was cooled to room temperature. The white precipitated residue was removed by filtration and then washed with ethanol three times. The white solids (0.1 mmol) were dissolved in a solution mixture (20.0 mL, CH3OH/DMF, 9:1, v/v) within three days. Crystals were obtained by slow evaporation at room temperature.

Experimental details

Using Olex2 [1], the structure was solved using Charge Flipping and refined with the ShelXL [3] refinement. All hydrogen atoms were positioned geometrically, with the d(C–H) = 0.97–0.99 Å, Uiso(H) = 1.2 times Ueq(parent atom).

Comment

A bis-pyridylhydrazone Schiff base ligand was synthesized. The nitrogen atoms on the pyridine ring have strong nucleophilic ability [5]. Acylhydrazone Schiff base compounds can be easily assembled with different transition metal ions in different coordination modes to form novel complexes [6].

In the crystal structure of the title compound, the asymmetric unit of the title compound consists of one target molecule. The title molecule shows a slightly twisted “Z” shape (see the Figure). The bond lengths and bond angles are in the normal ranges [6]. The amide forms an intermolecular hydrogen bond with the amide N on another molecule. The intermolecular N–H···O hydrogen bonds in the target compound extend the framework into a 2D structure.


Corresponding author: Ying Xiong, School of Chemistry and Materials, Guizhou Normal University, Guiyang, 550025, People’s Republic of China, E-mail:

Funding source: Science and Technology Foundation of Guizhou Province

Award Identifier / Grant number: [2019]2792

  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 and Technology Foundation of Guizhou Province (grant number [2019]2792).

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

References

1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

2. Bruker. APEX2, SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Search in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Brandenburg, K. DIAMOND. Visual Crystal Structure Information System. Ver. 4.0; Crystal Impact: Bonn, Germany, 2015.Search in Google Scholar

5. Zhang, N., Yuan, J., Liu, M. J. Synthesis and magnetism of binuclear fe complexes based on bis-pyridylhydrazone Schiff base ligands. Chin. J. Inorg. Chem. 2019, 11, 2066–2072.Search in Google Scholar

6. Hai, S. K., Lou, S. F., Qiu, X. Y. Syntheses, crystal structures and antimicrobial activity of copper and zinc complexes with aroylhydrazones. Chin. J. Inorg. Chem. 2016, 32, 906–912.Search in Google Scholar

Received: 2021-04-06
Accepted: 2021-04-26
Published Online: 2021-05-11
Published in Print: 2021-07-27

© 2021 Ying Xiong and Chuan Gao, published by De Gruyter, Berlin/Boston

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

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