Startseite The crystal structure of pyrazole nitrate
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The crystal structure of pyrazole nitrate

  • Feng Qingxin ORCID logo , Zhang Mian , Liu Jikai , Cheng Jun , Sheng Fanfan , Zhao Linxiu , Ren Fude und Cao Duanlin EMAIL logo
Veröffentlicht/Copyright: 8. Januar 2025

Abstract

C3H5N3O3, monoclinic, P21/c (no. 14), a = 3.702(2) Å, b = 11.109(7) Å, c = 13.105(8) Å, β = 94.21(2)°, V = 537.5(6) Å3, Z = 4, Rgt(F) = 0.0731, wRref(F2) = 0.2217, T = 170 K.

CCDC no.: 2406351

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: 0.20 × 0.09 × 0.04 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.14 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE, φ and ω
θmax, completeness: 26.8°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 2,939, 1,141, 0.084
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 668
N(param)refined: 90
Programs: Olex2, 1 SHELX 2 , 3
Table 2:

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

Atom x y z Uiso*/Ueq
O1 −0.0518 (8) 0.4859 (2) 0.3979 (2) 0.0433 (8)
O3 −0.1024 (9) 0.5772 (3) 0.2511 (2) 0.0498 (9)
O2 0.1601 (9) 0.4029 (3) 0.2658 (2) 0.0497 (9)
N1 0.5809 (9) 0.7276 (3) 0.5631 (3) 0.0380 (9)
N3 −0.0015 (9) 0.4900 (3) 0.3041 (2) 0.0396 (9)
N2 0.5961 (9) 0.6856 (3) 0.4672 (2) 0.0377 (9)
C3 0.3106 (10) 0.8569 (3) 0.4570 (3) 0.0362 (10)
H3 0.182356 0.925529 0.430454 0.043*
C1 0.4347 (11) 0.7635 (3) 0.4021 (3) 0.0368 (10)
H1A 0.409910 0.755525 0.329702 0.044*
C2 0.4056 (11) 0.8331 (3) 0.5571 (3) 0.0395 (10)
H2A 0.355926 0.882806 0.613335 0.047*
H1 0.697 (16) 0.683 (5) 0.619 (4) 0.075 (16)*
H2 0.712 (13) 0.620 (3) 0.454 (4) 0.069 (15)*

1 Source of material

Measure an appropriate amount of ethyl acetate (100–150 mL recommended) and add it to a 250 mL four-mouth bottle, stirring in an ice water bath. Weigh 10 g of pyrazole and add it to the reaction flask, stirring in an ice water bath. 6.8 mL of fuming nitric acid was added dropwise into the reaction solution (the temperature of the system should be controlled below 20 °C) using a constant pressure dropping funnel, and a large amount of white solids were generated in the reaction solution. The ice water bath was removed, the system temperature was raised to room temperature, and the reaction was kept warm for 0.5 h, and then the ice water bath was re-cooled to about 5 °C. The reaction solution is directly filtered to obtain a white powdery solid product. Melting point: (product pyrazole nitrate) 152–159 °C, (pyrazole) 66–70 °C.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms. All the non-hydrogen atoms were refined anisotropically.

3 Comment

Pyrazole occupies a very important position in the research and development of medicine, pesticides, energetic materials and other fields, and it has a variety of physiological effects, in addition, a series of nitropyrazole energetic compounds can also be obtained by introducing nitro groups into the pyrazole ring. 4 , 5 , 6 Therefore, in order to explore the reaction products of pyrazole and fuming nitric acid, the compound (pyrazole nitrate) was obtained by cooling and filtration after the reaction of pyrazole with fuming nitric acid in ethyl acetate solvent, and its crystal structure and data are shown in Fig.

As shown in Figure 1, the crystal structure of the title compound consists of one cation and one anion. Bond-lengths and angles are all in the expected ranges. 7 Hydrogen bonds connect the anions and cations to form a supramolecular structure.


Corresponding author: Cao Duanlin, School of Chemistry and Chemical Engineering, North University of China, Taiyuan 030051, Shanxi Province, P.R. China, E-mail:

Acknowledgements

We thank the Center of Testing and Analysis, Shanghai Institute, for support.

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

  2. Research funding: Center of Testing and Analysis, Shanghai Institute.

  3. Conflict of interest: 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. Cryst. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Suche in Google Scholar

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Received: 2024-09-30
Accepted: 2024-11-29
Published Online: 2025-01-08
Published in Print: 2025-04-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

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