Abstract
C14H12N4O2, monoclinic, C2/c (no. 15), a = 18.4206(15) Å, b = 8.8283(7) Å, c = 17.0215(14) Å, β = 110.253(4)°, V = 2596.9(4) Å3, Z = 8, Rgt(F) = 0.0715, wRref(F2) = 0.2072, T = 298 K.
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.
Crystal: | Colourless block |
Size: | 0.40 × 0.37 × 0.34 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.10 mm−1 |
Diffractometer, scan mode: | Oxford Diffraction Gemini, |
θmax, completeness: | 25.0°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 6429, 2288, 0.109 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 1434 |
N(param)refined: | 182 |
Programs: | CrysAlisPRO [1], Olex2 [2], SHELX [3], [4] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
O1 | 0.22660(11) | 0.9116(2) | 0.15949(12) | 0.0519(6) |
O2 | 0.20749(15) | 0.8810(3) | 0.39000(14) | 0.0763(8) |
N1 | 0.25723(14) | 0.8341(3) | 0.29203(14) | 0.0487(7) |
N2 | 0.31617(14) | 0.7918(3) | 0.26431(15) | 0.0482(7) |
N3 | 0.45265(19) | 0.7264(3) | 0.1147(2) | 0.0765(10) |
N4 | 0.12509(15) | 0.6702(3) | 0.19753(16) | 0.0540(7) |
C1 | 0.29565(17) | 0.8397(3) | 0.18899(18) | 0.0445(7) |
C2 | 0.19407(17) | 0.9071(3) | 0.22574(17) | 0.0475(8) |
H2 | 0.1856 | 1.0100 | 0.2424 | 0.057* |
C3 | 0.4090(2) | 0.7495(4) | 0.1612(2) | 0.0621(10) |
H3 | 0.4270 | 0.7144 | 0.2161 | 0.074* |
C4 | 0.33916(17) | 0.8219(3) | 0.13338(19) | 0.0471(8) |
C5 | 0.31275(19) | 0.8768(3) | 0.05280(19) | 0.0526(8) |
H5 | 0.2662 | 0.9292 | 0.0323 | 0.063* |
C6 | 0.3565(2) | 0.8526(4) | 0.0035(2) | 0.0628(9) |
H6 | 0.3400 | 0.8877 | −0.0514 | 0.075* |
C7 | 0.4246(2) | 0.7763(4) | 0.0362(3) | 0.0703(10) |
H7 | 0.4531 | 0.7579 | 0.0015 | 0.084* |
C8 | 0.11994(17) | 0.8204(3) | 0.19726(17) | 0.0442(7) |
C9 | 0.05139(18) | 0.8969(4) | 0.16945(18) | 0.0523(8) |
H9 | 0.0508 | 1.0022 | 0.1692 | 0.063* |
C10 | −0.01679(19) | 0.8165(4) | 0.1417(2) | 0.0603(9) |
H10 | −0.0644 | 0.8656 | 0.1230 | 0.072* |
C11 | −0.0120(2) | 0.6624(4) | 0.1426(2) | 0.0611(9) |
H11 | −0.0568 | 0.6041 | 0.1242 | 0.073* |
C12 | 0.05874(19) | 0.5941(4) | 0.17068(19) | 0.0586(9) |
H12 | 0.0607 | 0.4888 | 0.1711 | 0.070* |
C13 | 0.2605(2) | 0.8281(4) | 0.37170(19) | 0.0553(8) |
C14 | 0.3302(2) | 0.7557(4) | 0.4332(2) | 0.0677(10) |
H14A | 0.3234 | 0.7474 | 0.4865 | 0.102* |
H14B | 0.3750 | 0.8165 | 0.4391 | 0.102* |
H14C | 0.3371 | 0.6565 | 0.4137 | 0.102* |
Source of material
To a stirred solution of 2-pyridinecarboxaldehyde (1 mmol) in acetic anhydride (5 mL), was added nicotinohydrazide (1 mmol). The reaction mixture was refluxed and suitable colorless block crystals of this compound were purified by preparative thin-layer chromatography (PTLC) and recrystallised from dichloromethane.
Experimental details
The structure was solved with the Olex2 program [2] as an interface together with the SHELXT and SHELXL programs [3], [4]. Hydrogen atoms were treated using a riding model.
Comment
Oxazoline is a group of heterocyclic compounds with nitrogen and oxygen atoms, which showed bioactivities such as antibacterial [5] and anti-HIV [6] activities. To further study the structure-activity relationship of oxazoline, here we introduced a pyridine ring at the oxazoline and prepared an oxazoline-based derivative to find compounds with potential activity.
In the title structure, there is one crystallographically independent molecule in the asymmetric unit (shown in the figure). The compound contains one 1,3,4-oxadiazol group and two pyridine rings and all bond lengths are in normal ranges and they are similar to the known compound [6], [7]. The short C—N bond length of 1.277(3) Å (N2-C1) suggests a localized double bond, and the C—N bond length of 1.461(4) Å (N1-C2) suggests a localized single bond.
Acknowledgements
The present research was supported by the Science and Technology Fund of Guizhou [QKH-PTRC(2017)5735-22], the Youth Talent Development Project of Guizhou Provincial Department of Education [2017]169 and Guizhou Provincial Natural Science Foundation [QKH-J(2020)1Y070].
References
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©2020 Xiang Yu et al., published by De Gruyter, Berlin/Boston
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