Startseite The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
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The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O

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

Abstract

C7H10N4O, monoclinic, I2 (no. 5), a = 15.7815(13) Å, b = 4.3242(3) Å, c = 12.4658(9) Å, β = 106.301(8)°, V = 816.50(10) Å3, Z = 4, Rgt(F) = 0.0473, wRref(F2) = 0.1067, T = 113.25(10) K.

CCDC no.: 1958021

The asymmetric unit of 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 block
Size:0.45 × 0.11 × 0.03 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:Xcalibur, ω
θmax, completeness:26.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:1634, 1239, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1079
N(param)refined:110
Programs:CrysAlisPRO [1], SHELX [2], [3], Olex2 [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.27707(13)0.3971(5)0.32414(15)0.0367(6)
H1A0.26390.24740.27770.055*
H1B0.25550.35330.37820.055*
N10.47702(15)0.7137(6)0.58374(17)0.0253(6)
C10.50000.5228(10)0.50000.0305(10)
H1Ca0.54960.39110.53590.037*
H1Da0.45040.39110.46410.037*
N20.49432(16)1.0213(6)0.73081(18)0.0303(6)
C30.40763(19)1.0303(7)0.6656(2)0.0289(7)
H30.36351.14870.68170.035*
C20.53327(19)0.8294(7)0.6778(2)0.0297(8)
H20.59290.77900.70230.036*
C40.39538(19)0.8437(7)0.5751(2)0.0271(7)
H40.34310.81040.51900.033*
C50.0000−0.2706(10)0.50000.0280(10)
H5Aa0.0054−0.40220.56460.034*
H5Ba−0.0054−0.40220.43540.034*
N40.18829(16)0.1797(6)0.48032(19)0.0322(7)
N30.07871(15)−0.0765(5)0.51795(17)0.0255(6)
C70.18348(19)0.2556(7)0.5862(2)0.0325(8)
H70.22070.39480.63390.039*
C60.12390(19)−0.0199(8)0.4424(2)0.0284(7)
H60.1110−0.11110.37210.034*
C80.1174(2)0.1001(7)0.6109(2)0.0304(7)
H80.10110.10990.67700.036*
  1. aOccupancy: 0.50.

Source of material

In representative experiments, 3.0 g (53.4 mmol) KOH were dissolved in 20 mL solvent, then 3.0 g (44.1 mmol) imidazole were added, 3.8 g (22.1 mmol) dibromomethane were added at 293 K, The target compound was obtained by reaction at 333 K for 5 h. The crystal of the title compound was obtained by slow evaporation at 293 K.

Experimental details

All H atoms were positioned geometrically and treated as riding, with O—H bond lengths constrained to 0.85 Å and Uiso(H) = 1.5Ueq(O), N—H bond 0.88 Å and Uiso(H) = 1.2Ueq(N).

Comment

A methylene-bridged two-dentate nitrogen-containing ligand is a semi-rigid ligand. Cis-trans conformers can rotate along methylene due to the existence of single bonds in nitrogen-containing heterocycles [5]. The synthesis of bisimidazole methane coordination polymers has attracted great interest. Many compounds with novel structures and special functions have been synthesized by self-assembly method [6], [7], [8], [9]. The crystal structure of bis(imidazole-1-yl)methane has been reported [10].

The title compound has been reported for the first time in this paper. (cf. the figure) The asymmetric unit of the title structure contains one bis(imidazole-1-yl)methane (two halfs of a title molecule, arranged at two-fold axes) and one water molecule in a general position. The imidazole ring is almost flat in both moieties.

Acknowledgements

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

References

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

©2019 Yong Wang 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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