Skip to content
BY 4.0 license Open Access Published online by De Gruyter (O) May 26, 2022

Crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane – dimethylformamide (1/1), C11H13N9O9

Yuan Jun ORCID logo, Wu Bingheng, Wang Yong ORCID logo, Wang Jianlong, Cao Duanlin and Chen Lizhen

Abstract

C11H13N9O9, triclinic, P 1 (no. 2), a = 8.6588(3) Å, b = 8.7538(3) Å, c = 11.7312(4) Å, α = 78.230(1)°, β = 82.060(1)°, γ = 76.031(1)° V = 841.05(5) Å3, Z = 2, R gt (F) = 0.0376, wR ref (F 2) = 0.1006, T = 150.0 K.

CCDC no.: 2172229

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 plate
Size: 0.12 × 0.08 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.14 mm−1
Diffractometer, scan mode: D8 VENTURE, φ and ω
θ max, completeness: 26.4°, 99%
N(hkl)measured, N(hkl)unique, R int: 9685, 3412, 0.039
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2825
N(param)refined: 264
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
C1 0.49627 (18) 0.25303 (18) 0.54117 (13) 0.0191 (3)
C2 0.46354 (18) 0.21210 (18) 0.44190 (13) 0.0202 (3)
H2 0.520290 0.124787 0.405441 0.024*
C3 0.29685 (18) 0.42433 (18) 0.48727 (13) 0.0190 (3)
C4 0.25624 (18) 0.32579 (19) 0.30135 (13) 0.0205 (3)
H4A 0.138637 0.350173 0.318980 0.025*
H4B 0.288719 0.218561 0.279143 0.025*
C5 0.30248 (17) 0.44935 (18) 0.19916 (13) 0.0194 (3)
H5A 0.238106 0.457319 0.133840 0.023*
H5B 0.277609 0.555197 0.223402 0.023*
C6 0.58807 (18) 0.46915 (19) 0.19184 (13) 0.0205 (3)
H6 0.573842 0.540979 0.245103 0.025*
C7 0.72678 (18) 0.40440 (19) 0.13199 (13) 0.0211 (3)
C8 0.55469 (18) 0.31065 (18) 0.08136 (12) 0.0184 (3)
C9 0.7311 (2) −0.0545 (2) 0.20001 (14) 0.0256 (4)
H9 0.719104 −0.102338 0.136931 0.031*
C10 1.0173 (2) −0.1226 (2) 0.14598 (16) 0.0362 (4)
H10A 0.982453 −0.165075 0.085140 0.054*
H10B 1.088254 −0.209037 0.193688 0.054*
H10C 1.074788 −0.038730 0.109362 0.054*
C11 0.9072 (2) 0.0131 (3) 0.31526 (18) 0.0414 (5)
H11A 0.807488 0.081588 0.342751 0.062*
H11B 0.987995 0.077065 0.287908 0.062*
H11C 0.945298 −0.072706 0.379581 0.062*
N1 0.16688 (15) 0.56357 (16) 0.48195 (11) 0.0222 (3)
N2 0.39335 (15) 0.38512 (16) 0.56962 (11) 0.0207 (3)
N3 0.62649 (15) 0.17211 (16) 0.61035 (11) 0.0216 (3)
N4 0.33227 (15) 0.32359 (15) 0.40700 (11) 0.0187 (3)
N5 0.47384 (14) 0.40785 (15) 0.15826 (10) 0.0180 (3)
N6 0.70750 (15) 0.30595 (16) 0.06250 (11) 0.0217 (3)
N7 0.47828 (16) 0.22097 (16) 0.02367 (11) 0.0238 (3)
N8 0.88256 (16) 0.43254 (18) 0.13924 (12) 0.0279 (3)
N9 0.87855 (16) −0.05601 (17) 0.21981 (12) 0.0265 (3)
O1 0.15276 (14) 0.64737 (14) 0.55605 (10) 0.0307 (3)
O2 0.07898 (13) 0.59010 (14) 0.40264 (10) 0.0270 (3)
O3 0.65040 (14) 0.23477 (15) 0.68883 (10) 0.0288 (3)
O4 0.70779 (13) 0.04601 (14) 0.58430 (10) 0.0269 (3)
O5 0.88761 (15) 0.53664 (17) 0.19335 (11) 0.0369 (3)
O6 0.99906 (15) 0.35025 (18) 0.09252 (13) 0.0465 (4)
O7 0.60791 (14) 0.00429 (15) 0.25718 (10) 0.0301 (3)
O8 0.55945 (16) 0.15560 (17) −0.05365 (11) 0.0372 (3)
O9 0.33831 (14) 0.21837 (16) 0.05561 (11) 0.0345 (3)

Source of material

All reagents were purchased with analysis grade. In representative experiments, 5 mL HNO3 and 15 mL H2SO4 were mixed. Then 14 g (50 mmol) 1,2-bis(2-nitro-1H-imidazol-1-yl)ethane were added at 293 K. The target compound was obtained by reaction at 348 K for 9 h. The raw product was dissolved in N,N-dimethylformamide (DMF) and the crystal of the title compound was obtained by slow evaporation at 293 K.

Experimental details

Using Olex2 [2], the structure was solved 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).

Comment

Bisimidazole moieties bridged by other groups have always been a hot topic [5], [6], [7], [8]. These compounds concatenate two imidazole groups and have the features of both flexibility and rigidity. The title compound has been reported for the first time in this paper (cf. Figure).

The asymmetric unit of the title structure contains one 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane and one dimethylformamide molecule. The nitroimidazole ring are almost flat, and the dihedral angle of the two nitroimidazole rings is 66.50°.


Corresponding author: Yuan Jun, Shanxi College of Technology, Shuozhou 036012, Shanxi Province, P. R. China, E-mail:

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

  2. Research funding: We thank the Center of Testing and Analysis, Shanghai Institute, for support.

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

References

1. BRUKER. Saint, Apex2 and Sadabs; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

2. 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

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. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

5. Min, P., Tao, W., Jin, C. M. Assembly of two coordination polymers [Cu(BIM)(suc)]n and [Cd(BIM)(ox)(H2O)]n constructed from bis(imidazol-1-yl)methane. J. Coord. Chem. 2011, 64, 600–609.10.1080/00958972.2011.552109Search in Google Scholar

6. Wang, Y., Yuan, J., Cao, D. L., Wang, J. L., Chen, L. Z. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4. Z. Kristallogr. N. Cryst. Struct. 2020, 235, 217–218.Search in Google Scholar

7. Jin, S., Chen, W., Qiu, H. Syntheses and structural characterization of a one-dimensional chain, two-dimensional noninterpenetrated grid, and three-dimensional polycatenane coordination polymers assembled from flexible bidentate imidazolyl ligands. Cryst. Growth Des. 2007, 7, 2071–2079; https://doi.org/10.1021/cg060666q.Search in Google Scholar

8. Wang, Y., Yuan, J., Cao, D. L., Wang, J. L., Chen, L. Z. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O. Z. Kristallogr. N. Cryst. Struct. 2020, 235, 215–216.10.1515/ncrs-2019-0581Search in Google Scholar

Received: 2022-03-31
Accepted: 2022-05-12
Published Online: 2022-05-26

© 2022 Yuan Jun et al., published by De Gruyter, Berlin/Boston

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