Home The crystal structure of 1,2-bis(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)ethane, C16H12N6O2
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The crystal structure of 1,2-bis(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)ethane, C16H12N6O2

  • Fei Liu EMAIL logo , Huang Fang , Fang Zhang and Qifan Chen
Published/Copyright: November 15, 2017

Abstract

C16H12N6O2, monoclinic, P21/c (no. 14), a = 4.791(5) Å, b = 28.156(5) Å, c = 5.747(5) Å, β = 109.941(5)°, V = 728.8(10) Å3, Z = 2, Rgt(F) = 0.0407, wRref(F2) = 0.0998, T = 293(2) K.

CCDC no.: 1583797

The crystal structure is shown in the figure. 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:0.21 × 0.17 × 0.15 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:Bruker FRAMBO, φ and ω-scans
2θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:2228, 1282, 0.019
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 955
N(param)refined:109
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
N10.3221(3)0.07196(5)0.7006(3)0.0411(4)
N20.5881(3)0.08333(5)1.1033(3)0.0513(5)
N3−0.2663(4)0.18266(5)0.7273(3)0.0535(5)
O10.7156(3)0.04690(4)1.0016(2)0.0506(4)
C10.6328(4)0.00856(6)0.6068(3)0.0442(5)
H1A0.729441−0.0183840.7072260.053*
H1B0.7743240.0233950.5426160.053*
C20.5429(4)0.04303(6)0.7622(3)0.0397(4)
C30.3589(4)0.09646(6)0.9171(3)0.0386(4)
C40.1596(4)0.13453(6)0.9348(3)0.0393(4)
C50.1986(4)0.15872(7)1.1536(4)0.0537(6)
H50.3527280.1507241.2976900.064*
C60.0056(5)0.19465(7)1.1536(4)0.0575(6)
H60.0289220.2117111.2975400.069*
C7−0.2214(5)0.20515(7)0.9400(4)0.0531(5)
H7−0.3515530.2293920.9438780.064*
C8−0.0752(4)0.14794(6)0.7284(3)0.0443(5)
H8−0.1022270.1318560.5809200.053*

Source of material

N-hydroxy-nicotinamidine is easily available by a literature known synthesis [3]. A mixture of N-hydroxy-nicotinamidine (0.04 mol) and succinic anhydride (0.08 mol) was heated to 428 K and kept at this temperature for 4 h. The reaction mixture was cooled to room temperature, and washed with water. A solution (15 mL) of methanol was added. The mixture was shocked at ultrasonic and washed with a solution of sodium hydroxide (1 M, 10 mL). The pH value of the solution was adjusted to three. The suspension was filtered. The filter residue was washed with water, recrystallized from ethanol, dissolved with methanol, filtered, and was allowed to diffuse slowly into the solution of the filtrate. Colourless crystals were obtained in about 4 weeks.

Experimental details

H atoms were placed in calculated positions and treated as constrained on their parent atoms, with C—H = 0.93 or 0.97 Å and Uiso(H) = 1.2 or 1.5Ueq(C).

Discussion

Many molecules containing a 1,2,4-oxadiazole moiety exhibit interesting pharmacological properties and biological activities [4], [5], [6], [7], [8], [9]. Furthermore, the 1,2-bis-1,2,4-oxadiazol-5-yl)ethane core tecton is well known to construct coordination polymers [10]. As an ongoing part of our investigations, we report the preparation and structure of the title compound. The title compound is approximately planar and inversion symmetry is present (cf. the figure). The dihedral angle of C1–C1–C2–N1 is found to be 28.7(3)°. Each 3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl moiety is almost planar. In the crystal structure, molecules are liked through intermolecular forces.

Acknowledgements

This work is financially supported by the Natural Science Foundation of Liaoning Province (No. 2013020090) and Program of Liaoning Provincial Key Laboratory of Functional Textile Materials Liaoning Province Key Laboratory of Functional Textile Materials.

References

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Received: 2017-8-13
Accepted: 2017-11-3
Published Online: 2017-11-15
Published in Print: 2018-1-26

©2018 Fei Liu et al., published by De Gruyter, Berlin/Boston

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

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