Home Physical Sciences Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5
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Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5

  • Dong Wang , Yu-Jie Xie , Ye-Meng Sheng , Bo-Bo Han , Wen-Duo Zhu and Jiu-Fu Lu ORCID logo EMAIL logo
Published/Copyright: October 23, 2025

Abstract

C12H8N2O5, triclinic, P1¯ (no. 2), a = 6.9215(2) Å, b = 8.0572(2) Å, c = 19.8378(6) Å, α = 98.657(1)°, β = 94.076(1)°, γ = 90.495(1)°, V = 1090.73(5) Å3, Z = 2, Rgt(F) = 0.0602, wRref(F2) = 0.1329, T = 293(2) K.

CCDC no.: 2464122

The molecular structure is shown in the figure. Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Plate, clear light colourless
Size: 0.8 × 0.8 × 0.3 mm
Wavelength: Mo radiation (0.71073 Å)
μ: 0.13 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω-scans
θmax, completeness: 28.3°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 30883, 5392, 0.063
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 4,107
N(param)refined: 350
Programs: Bruker programs, 1 OLEX2, 2 SHELX 3 , 4

1 Source of material

The ethyl 1-(4-(ethoxycarbonyl)phenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylate (0.4 mmol) and sodium hydroxide (0.5 mmol) were dissolved in 100 mL N,N-dimethylformamide, then added to a 250 mL flask and heated at 323 K for 2 h and cooled down to room temperature acidified by addition of 15 % HCl solution until pH = 2. The residue was thoroughly washed, carefully filtered, and subsequently dried, ultimately yielding the desired compound in the form of colorless block crystals.

2 Experimental details

Using Olex2, 2 the structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL 4 refinement package.

3 Comment

Pyridazine derivatives constitute a particularly significant class of biologically active heterocycles. These compounds have garnered considerable attention as ligands due to their remarkable structural and synthetic versatility, precise tunability, and selectivity towards transition metal atoms. 5 Their diverse therapeutic potential, encompassing anticancer, 6 , 7 antidiabetic, 8 , 9 and antibiotic activities, 10 has been extensively documented. Leveraging this understanding, we have achieved the successful synthesis of a novel pyridazine carboxyl derivative, achieved by incorporating a benzene ring adorned with carboxyl groups onto the pyridazine ring. Simultaneously, numerous studies have reported the syntheses of transition metal complexes utilizing this derivative, specifically 1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid, as a ligand and explored their properties. 11 , 12 , 13 , 14 , 15 , 16 However, despite these reports on complex formation and properties, the crystal structure of this pyridazine carboxylic acid ligand itself remains unreported to date.

Single-crystal X-ray diffraction analysis reveals that the asymmetric unit of the title compound contains two crystallographically independent molecules of 1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid. These two molecules exhibit similar spatial configurations, differing primarily in the dihedral angles between their respective benzene and pyridazine rings, measured as 34.74° and 23.90°. The nitrogen-nitrogen bond lengths (N1–N2: 1.3306(16) Å; N3–N4: 1.3342(17) Å), as well as pertinent carbon–nitrogen bond lengths, exhibit intermediate values between those typical for N–N single bonds (1.45 Å) and N=N double bonds (1.25 Å). This observation indicates significant delocalization of p-electrons within the molecular framework. Finally, adjacent molecules are interconnected via intermolecular hydrogen bonding and ππ stacking interactions, collectively forming a three-dimensional supramolecular architecture.


Corresponding author: Jiu-Fu Lu, Shaanxi Key Laboratory of Catalysis, College of Chemical & Environment Science, Shaanxi University of Technology, Hanzhong, 723001, P.R. China, E-mail:

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

  2. Research funding: The work was supported by science and technology innovation project of colleges and universities in Shanxi Province (No. 2023L435).

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

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Received: 2025-08-07
Accepted: 2025-10-02
Published Online: 2025-10-23
Published in Print: 2025-12-17

© 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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