Home The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
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The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3

  • Yuan Jun EMAIL logo , Wu Bingheng , Wang Yong , Wang Jianlong , Cao Duanlin and Chen Lizhen
Published/Copyright: May 11, 2023

Abstract

C5H7N3O3, monoclinic, P21/n (no. 14), a = 8.7821(7) Å, b = 7.1320(5) Å, c = 11.6293(10) Å, β =  104.718 ( 3 ) , V = 704.49(10) Å3, Z = 4, R g t (F) = 0.0468, w R r e f (F 2) = 0.1125, T = 170.0 K.

CCDC no.: 2259820

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: Yellow block
Size: 0.17 × 0.08 × 0.06 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.12 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE, φ and ω
θ max, completeness: 26.4°, 99°%
N(hkl) measured, N(hkl) unique, R int: 4645, 1423, 0.048
Criterion for I obs, N(hkl) gt: I obs°>°2σ(I obs), 1070
N(param) refined: 101
Programs: Bruker [1], Olex2 [2], SHELX [3,4]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.65589 (17) 0.2045 (2) 0.55208 (12) 0.0325 (4)
O2 0.7821 (2) 0.5489 (2) 0.56037 (14) 0.0469 (5)
N2 0.50669 (18) 0.4454 (2) 0.28723 (14) 0.0231 (4)
N1 0.58742 (18) 0.2648 (2) 0.44610 (13) 0.0220 (4)
N3 0.6993 (2) 0.5806 (2) 0.46043 (15) 0.0284 (4)
O3 0.6963 (2) 0.7328 (2) 0.41011 (15) 0.0502 (5)
C3 0.5993 (2) 0.4385 (2) 0.40040 (16) 0.0213 (4)
C2 0.4869 (2) 0.1618 (3) 0.36015 (17) 0.0253 (5)
H2 0.456838 0.035091 0.366834 0.030*
C1 0.4378 (2) 0.2744 (3) 0.26314 (17) 0.0259 (5)
H1 0.366768 0.238960 0.190277 0.031*
C4 0.4718 (2) 0.6047 (3) 0.20259 (18) 0.0285 (5)
H4A 0.455924 0.719465 0.245950 0.034*
H4B 0.372733 0.578718 0.141706 0.034*
C5 0.6021 (3) 0.6388 (3) 0.1416 (2) 0.0408 (6)
H5A 0.570702 0.739144 0.082778 0.061*
H5B 0.621855 0.523700 0.101729 0.061*
H5C 0.698192 0.675780 0.200812 0.061*

1 Source of material

All reagents were purchased with analysis grade. In representative experiments, 7.05 g hydroxylamine hydrochloride (NH2OH·HCl), 5.3 g sodium carbonate (Na2CO3), 14.5 g glyoxal (C2H2O2), 9.7 g formaldehyde (CH2O), 7.5 g glycine (C2H5NO2) were added in the ice bath, and reacted at 273 K for 12 h. Then we added 6.3 g nitric acid (HNO3), and the target compound was obtained by reaction at 420 K for 12 h. The crystal of the title compound was obtained by slow evaporation at 293 K.

2 Experimental details

A suitable crystal was selected and on a ‘Bruker D8 VENTURE’ diffractometer. Using Olex2 [2], the structure was solved with the ShelXT [3] structure solution program and refined with the ShelXL [4] refinement package. All H atoms were positioned geometrically and treated as riding, and U iso(H) = 1.2U eq (C).

3 Comment

Nitroimidazoles are special compounds due to their heterocycle and they have been used in medicine and pharmacy [5], [6], [7], [8]. Nitroimidazole-N-oxides which contain both nitro group and oxide are predicted to have a wide range of applications.

The title compound has been reported for the first time in this paper (cf. the figure). The title structure contains a nitro group bound to a imidazole-oxide. The imidazole ring is flat, and the angle between ethyl and nitro-imidazole–oxide, is about 104°. All geometric parameters are in the expected range [9].


Corresponding author: Yuan Jun, Shanxi College of Technology, Shuozhou 036000, Shanxi, P.R. China, E-mail:

Funding source: 2022 Shanxi Province Higher Education Science and Technology Innovation Project 2022L619

Award Identifier / Grant number: 2022L619

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: 2022 Shanxi Province Higher Education Science and Technology Innovation Project 2022L619.

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

References

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Received: 2023-04-04
Accepted: 2023-04-29
Published Online: 2023-05-11
Published in Print: 2023-08-28

© 2023 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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