Home The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
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The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4

  • Zhao Zeng-Bing , Cheng Lan-Xing , Yang Shu-Cheng , Chai Yong-Li EMAIL logo and Tai Xi-Shi ORCID logo EMAIL logo
Published/Copyright: August 14, 2024

Abstract

C12H14N4O4, triclinic, P 1 (no. 2), a = 6.79127(19) Å, b = 10.0328(3) Å, c = 10.0542(2) Å, α = 90.027(2)°, β = 97.124(2)°, γ = 101.983(3)°, V = 664.71(3) Å3, Z = 2, Rgt(F) = 0.0539, wRref(F2) = 0.1580, T = 292 K.

CCDC no.: 2375758

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: 0.14 × 0.12 × 0.10 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.90 mm−1
Diffractometer, scan mode: XtaLAB Synergy R, ω
θmax, completeness: 73.2°, 99 %
N(hkl)measured, N(hkl)unique, Rint: 6,918, 2,553, 0.036
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2075
N(param)refined: 197
Programs: Bruker, 1 Olex2, 2 SHELX, 3 Diamond 4
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.3846 (2) 1.08152 (11) 0.22115 (11) 0.0593 (4)
O2 0.1810 (2) 0.47535 (11) 0.22257 (11) 0.0606 (4)
N1 0.2602 (2) 0.93718 (13) 0.04358 (11) 0.0438 (3)
H1 0.261 (3) 1.012 (3) −0.009 (2) 0.071 (6)*
N2 0.25766 (19) 0.60161 (12) 0.41552 (11) 0.0398 (3)
H2 0.289019 0.683036 0.454680 0.048*
N3 0.24204 (19) 0.48575 (12) 0.48979 (12) 0.0406 (3)
N4 0.2440 (2) 0.16240 (13) 0.87182 (13) 0.0479 (4)
C1 0.3224 (2) 0.96118 (15) 0.17688 (14) 0.0414 (4)
C2 0.3104 (2) 0.84265 (14) 0.25766 (13) 0.0404 (4)
H2A 0.351244 0.853117 0.351580 0.048*
C3 0.2414 (2) 0.71539 (14) 0.20160 (13) 0.0368 (3)
C4 0.1930 (3) 0.81138 (17) −0.01329 (14) 0.0478 (4)
H4 0.152380 0.801706 −0.107266 0.057*
C5 0.1828 (2) 0.69877 (15) 0.06207 (14) 0.0435 (4)
H5 0.136984 0.610345 0.021663 0.052*
C6 0.2234 (2) 0.58664 (14) 0.28049 (14) 0.0390 (3)
C7 0.2815 (2) 0.50292 (15) 0.61604 (14) 0.0421 (4)
H7 0.319939 0.592497 0.654484 0.050*
C8 0.2678 (2) 0.38445 (15) 0.70292 (14) 0.0385 (3)
C9 0.2075 (2) 0.25197 (16) 0.65100 (14) 0.0431 (4)
H9 0.173563 0.234795 0.557155 0.052*
C10 0.1979 (3) 0.14599 (16) 0.73859 (15) 0.0478 (4)
H10 0.155995 0.055660 0.702265 0.057*
C11 0.3145 (3) 0.40263 (16) 0.84091 (15) 0.0455 (4)
H11 0.355558 0.491749 0.880265 0.055*
C12 0.3005 (3) 0.28940 (18) 0.92052 (15) 0.0484 (4)
H12 0.333080 0.303309 1.014830 0.058*
O3 0.7087 (3) 1.16425 (14) 0.41834 (12) 0.0663 (4)
H3A 0.610 (3) 1.137 (3) 0.359 (2) 0.099*
H3B 0.818 (3) 1.173 (3) 0.382 (3) 0.099*
O4 1.0819 (2) 1.20317 (12) 0.31213 (12) 0.0594 (4)
H4A 1.182 (3) 1.168 (3) 0.292 (3) 0.089*
H4B 1.127 (4) 1.2888 (18) 0.309 (3) 0.089*

1 Source of materials

An amount of 0.107 g 4-pyridinecarboxaldehyde (1.0 mmol), 0.153 g 2-hydroxyisonicotinohydrazide (1.0 mmol), 0.040 g NaOH (1.0 mmol), and 0.1015 g magnesium chloride hexahydrate (0.50 mmol) were added together to the 18 ml ethanol-water solution (v:v = 2:1) and stirred to dissolve. Heating the above solution to 75 °C for reaction for 4 h. The colorless needle-like crystals were obtained from filtrate after 25 days.

2 Experimental details

The hydrogen atoms were positioned geometrically (C–H = 0.95 Å, N–H = 0.88–0.92 Å, O–H = 0.84–0.88 Å). Their Uiso values were set to 1.2Ueq or 1.5Ueq of the parent atoms.

3 Comment

The study of the structure and properties of acylhydrazone compounds and their complexes has always been one of the priorities of coordination chemistry. 5 , 6 Because they show excellent properties such as vibrio harveyi inhibition activity, 7 turn-on fluorescent chemosensor, 8 neuritogenic activities in Neuro-2a cells, 9 and magnetic properties. 10 Some acylhydrazone compounds and their complexes have been synthesized and structurally characterized in our study group. 11 , 12 , 13 , 14 The molecular structure of the title compound is shown in figure. Our original intention was to synthesize an acylhydrazone magnesium complex, and unfortunately, magnesium ions are not involved in coordination. In the title compound, the bond lengths of C7=N3 and C6=O2 are 1.2684(19) and 1.2218(18) Å, respectively, which are shorter to C6–N2 (1.3516(18) Å) and C1–O1 (1.2551(19) Å), showing that C7=N3 and C6=O2 are expected for double bonds. The dihedral angle between two pyridine rings is 3.72°, showing that the 2-hydroxy-isonicotinic acid pyridin-4-ylmethylene-hydrazide molecule is almost coplanar. The title compound molecules form 1D chained structure by intermolecular N(1)–H(1)⋯N(4) hydrogen bonds, and the 1D chains further form a three-dimensional network structure by hydrogen bonds.


Corresponding authors: Chai Yong-Li, Henan Academy of Sciences, Zhengzhou, 450046, P.R. China; and Henan Chemical Industry Research Institute Co., Zhengzhou, 450052, P.R. China E-mail: , and Tai Xi-Shi, College of Chemistry and Chemical Engineering, Weifang University, Weifang, Shandong 261061, P. R. China, E-mail:

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

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

  3. Research funding: Henan Academy of Sciences (220608035, 231508001, 242208025) and the National Natural Science Foundation of China (No. 21171132, https://doi.org/10.13039/501100001809).

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Received: 2024-07-01
Accepted: 2024-08-05
Published Online: 2024-08-14
Published in Print: 2024-10-28

© 2024 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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