Startseite The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
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The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4

  • Wang Yong ORCID logo , Yuan Jun , Cao Duanlin EMAIL logo , Wang Jianlong und Chen Lizhen
Veröffentlicht/Copyright: 18. Oktober 2019

Abstract

C7H6N6O4, monoclinic, P21/c (no. 14), a = 21.0402(7) Å, b = 7.9959(3) Å, c = 11.8012(4) Å, β = 102.379(1)°, V = 1939.22(12) Å3, Z = 8, Rgt(F) = 0.0481, wRref(F2) = 0.1296, T = 170 K.

CCDC no.: 1958055

The crystal 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:Block, colorless
Size:0.16 × 0.11 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.14 mm−1
Diffractometer, scan mode:Bruker APEX-II, ω-scans
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:17779, 3885, 0.035
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3131
N(param)refined:307
Programs:Bruker programs [1], SHELX [2], [3], OLEX2 [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.51996(9)0.0045(2)0.74135(15)0.0593(5)
O20.59384(8)0.0466(2)0.64212(16)0.0595(5)
O30.37100(7)0.8863(2)0.72055(15)0.0494(4)
O40.28112(8)0.8320(2)0.77591(14)0.0457(4)
O50.76985(11)−0.1984(2)0.27015(16)0.0682(6)
O60.86232(11)−0.0747(3)0.27101(17)0.0706(6)
O70.98989(8)−0.2980(2)1.01603(15)0.0494(4)
O80.89684(8)−0.1999(2)1.03517(14)0.0473(4)
N10.53978(9)0.0682(2)0.66043(17)0.0453(5)
N20.51421(9)0.2598(2)0.49720(17)0.0438(4)
N30.40881(8)0.2963(2)0.48938(14)0.0323(4)
N40.32062(8)0.4694(2)0.51962(15)0.0349(4)
N50.25439(10)0.5756(3)0.6235(2)0.0625(7)
N60.32105(8)0.8039(2)0.71549(15)0.0369(4)
N70.81427(11)−0.1034(3)0.31257(17)0.0515(5)
N80.76113(9)−0.0429(2)0.47366(16)0.0421(4)
N90.83789(8)0.1188(2)0.57747(15)0.0351(4)
N100.91305(7)0.0930(2)0.75936(14)0.0338(4)
N110.99290(8)−0.0799(2)0.83821(15)0.0356(4)
N120.94339(8)−0.2031(2)0.98760(15)0.0365(4)
C10.43008(10)0.1908(3)0.57943(18)0.0369(5)
H10.4053670.1412410.6291430.044*
C20.49453(10)0.1719(2)0.58274(17)0.0341(4)
C30.46082(10)0.3334(3)0.44252(19)0.0404(5)
H30.4586240.4046370.3773900.048*
C40.34333(10)0.3527(3)0.44190(18)0.0387(5)
H4A0.3138020.2548860.4280930.046*
H4B0.3419460.4079370.3663540.046*
C50.35072(9)0.6089(3)0.57166(17)0.0340(4)
H50.3913830.6544830.5645950.041*
C60.30935(9)0.6676(2)0.63575(18)0.0339(4)
C70.26291(12)0.4567(3)0.5516(3)0.0635(8)
H70.2319390.3711630.5250030.076*
C80.81183(11)−0.0217(3)0.42008(18)0.0380(5)
C90.85972(10)0.0763(3)0.48104(18)0.0386(5)
H90.8994130.1079650.4609680.046*
C100.77865(10)0.0445(3)0.56942(19)0.0394(5)
H100.7531310.0548110.6264190.047*
C110.87474(10)0.2089(3)0.67704(19)0.0394(5)
H11A0.8445170.2713690.7152540.047*
H11B0.9039650.2905560.6509920.047*
C120.89224(9)0.0136(3)0.84660(18)0.0346(4)
H120.8520260.0276500.8697650.042*
C130.94201(9)−0.0905(2)0.89307(17)0.0319(4)
C140.97355(10)0.0324(3)0.75756(18)0.0369(5)
H140.9986650.0678010.7039640.044*

Source of material

The title compound was prepared by nitrifying bis(imidazole-1-yl)methane. The title compound was recrystallized from ether solution at 293 K for 2 days to give colorless crystals.

Experimental details

All H atoms were positioned geometrically and treated as riding, with N—H bond 0.88 Å and Uiso(H) = 1.2Ueq(N). Difference electron density peaks and holes near N1 suggest a small (not introduced) disorder at that group.

Discussion

Nitroimidazole derivatives is one of the research focuses on energetic materials [5], [6]. A series of compounds have been synthesized, such as 1,4-dinitroimidazole, 2,4-dinitroimidazole, 2,4,5-trinitroimidazole and 1-methyl-2,4,5-trinitroimidazole, etc. [7], [8], [9], [10]. Nitroimidazole derivatives bridged by methylene are also expected to become a new energetic material, the title compound is one of them. Here we report the crystal structure of the title compound (cf. the figure).

The asymmetric unit of the title structure contains two crystallographically independent bis(4-Nitroimidazol-1yl-)methane molecules. The imidazole ring and nitro is almost flat.

Acknowledgements

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

References

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3. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

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Received: 2019-08-12
Accepted: 2019-10-08
Published Online: 2019-10-18
Published in Print: 2019-12-18

©2019 Wang Yong et al., published by De Gruyter, Berlin/Boston

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

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  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
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