Startseite Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
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Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O

  • Gui-Rong You und Guo-Wu Rao EMAIL logo
Veröffentlicht/Copyright: 18. September 2018

Abstract

C9H5F3N2O, orthorhombic, Pnma (no. 62), a = 7.276(2) Å, b = 6.7773(19) Å, c = 17.613(5) Å, V = 868.5(4) Å3, Z = 4, Rgt(F) = 0.0399, wRref(F2) = 0.1122, T = 293(2) K.

CCDC no.: 1863528

The crystal structure is shown in the figure (i = x, −y, z). Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Block, colourless
Size:0.65×0.32 × 0.25 mm
Wavelength:Mo radiation (0.71073 Å)
μ:0.15 mm1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25.01°, 100.0%
N(hkl) measured, N(hkl) unique, Rint:3447, 839, 0.0184
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 729
N(param)refined:89
Programs:Bruker programs [1], SHELX [2], [3], WinGX and ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
O(1)0.5672(4)0.25000.3061(1)103(1)
N(1)0.1282(2)0.25000.4931(1)0.062(1)
N(2)0.4273(2)0.25000.4624(1)0.046(1)
F(1)0.1184(2)0.0932(2)0.6568(1)0.100(1)
F(2)0.3077(3)0.25000.7259(1)110(1)
C(1)0.2995(3)0.25000.5202(1)0.047(1)
C(2)0.1488(4)0.25000.4175(2)0.069(1)
H(2)0.05050.25000.38380.083*
C(3)0.3284(3)0.25000.3951(1)0.058(1)
C(4)0.4055(5)0.25000.3204(2)0.080(1)
H(4)0.32430.25000.27960.096*
C(5)0.6134(3)0.25000.4759(1)0.052(1)
H(5)0.69630.25000.43570.063*
C(6)0.6736(3)0.25000.5473(1)0.058(1)
H(6)0.79930.25000.55690.069*
C(7)0.5492(3)0.25000.6082(1)0.057(1)
H(7)0.59340.25000.65770.068*
C(8)0.3642(3)0.25000.5957(1)0.051(1)
C(9)0.2287(4)0.25000.6586(1)0.069(1)

Source of materials

The title compound was prepared from 8-(trifluoromethyl)imidazo[1,2-a]pyridine, according to the procedure of McKenna et al. [5]. The intermediate of 8-(trifluoromethyl)imidazo[1,2-a]pyridine was prepared according to the procedure of Mu et al. [6].

Experimental details

H atoms were positioned geometrically and refined using a riding model. H atoms were given isotropic displacement parameters equal to 1.2 times the equivalent isotropic displacement parameters of their parent atoms, and C—H distances were set equal to 0.93 Å.

Comment

Imidazo[1,2-a]pyridine derivatives have a high potential for biological activity [7]. In continuation of our work on the structure and biological activity of heterocycles derivatives [8], [9], [10], [11], [12], [13], we obtained a colourless crystalline compound prepared from 8-(trifluoromethyl)imidazo[1,2-a]pyridine. The structural identity was resolved using single-crystal X-ray diffraction.

The title molecule consists of the imidazo[1,2-a]pyridine core moiety, and one trifluoromethyl and one carbaldehyde group, which confirms the synthesis of the title compound. The imidazo[1,2-a]pyridine ring (C1/C2/C3/C5/C6/C7/C8/N1/N2) and atoms C9/F2/C4/O1 are coplanar due to the crystallographically imposed mirror plane. At least one non-classical intermolecular C4′-H4′⋯O1 hydrogen bond exists between two imidazo[1,2-a]pyridine of neighbouring molecules with a C–H⋯O angle of 168.4° (′ = −1/2 + x, 1/2 − y, 1/2 − z).

Acknowledgements

This work was supported by the Medical and Health Technology Development Program of Shandong Province, China (2015WS0105).

References

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Received: 2018-06-06
Accepted: 2018-08-23
Published Online: 2018-09-18
Published in Print: 2018-11-27

©2018 Gui-Rong You et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
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