Startseite Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
Artikel Open Access

Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4

  • Fang Xiangqing EMAIL logo , Wang Ren , Du Kai , Gu Jia und Yang Liguo ORCID logo
Veröffentlicht/Copyright: 14. Oktober 2019

Abstract

C21H25N9O4, monoclinic, P2/n (no. 13), a = 10.277(3) Å, b = 10.081(3) Å, c = 11.264(4) Å, β = 104.582(4)°, V = 1129.4(6) Å3, Z = 2, Rgt(F) = 0.0452, wRref(F2) = 0.1278, T = 296(2) K [1], [2], [3].

CCDC no.: 1957155

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:0.08 × 0.06 × 0.04 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.1 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:9828, 1991, 0.016
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1805
N(param)refined:158
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.60883(12)0.66117(10)0.43181(9)0.0493(3)
O20.47501(15)0.5878(2)0.19204(12)0.0886(6)
H2A0.51070.59020.26580.133*
N10.75000.61340(16)0.75000.0327(4)
N20.68861(13)0.47479(12)0.53866(11)0.0408(3)
H11A0.72870.44190.60880.049*
N30.64888(13)0.39280(12)0.43823(10)0.0387(3)
N50.61892(15)0.04813(13)0.37856(12)0.0480(4)
N60.54283(16)0.14168(15)0.13770(12)0.0562(4)
C10.75000.8885(2)0.75000.0442(5)
H10.75000.98080.75000.053*
C20.70931(15)0.82006(15)0.64109(13)0.0407(4)
H20.68140.86470.56680.049*
C30.71110(13)0.68233(14)0.64552(12)0.0338(3)
C40.66495(14)0.60590(14)0.52754(12)0.0348(3)
H4A0.80100.21470.61310.095*
H4B0.67950.11570.58130.095*
H4C0.66400.25330.64120.095*
C50.65901(15)0.26815(14)0.46068(13)0.0378(4)
C60.61670(14)0.17798(14)0.35373(13)0.0376(4)
C70.57707(17)0.22334(16)0.23303(14)0.0460(4)
H70.57450.31430.21870.055*
C80.5463(2)0.01231(18)0.16439(16)0.0588(5)
H80.5234−0.04870.10060.071*
C90.5824(2)−0.03319(17)0.28271(16)0.0565(5)
H90.5814−0.12410.29660.068*
C100.5693(3)0.6184(3)0.1273(2)0.0820(7)
H10A0.62750.68730.16930.123*
H10B0.52420.64820.04650.123*
H10C0.62150.54090.12130.123*
C110.7050(2)0.20754(18)0.58520(15)0.0635(5)

Source of material

2,6-Pyridinedicarboxylic acid dihydrazide (1.95 g, 0.010 mol) was added to a dry methanolic solution (50 mL) of the methyl ester of iminopyrazine-2-carboxylic acid (2.6 g, 0.025 mol), prepared in situ from 2-cyanopyrazine and sodium metal (stirred at room temperature for 12 h) and the mixture refluxed for 24 h with the formation of a yellow powder. The solid was filtered off washed with water, methanol and ether and dried under vacuum. Yield (6.5 g, 80%).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5 Ueq(C) and with Uiso(H) set to 1.2 Ueq(N) [1], [2], [3].

Discussion

The extended “polytopic” ligands 2pzoap (N′2,N′6-bis(1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide) contain multiple, contiguous coordination pockets, and in principle there are many different ways in which they could bind metal ions. The complexes containing the ligand 2pzoap have been reported. But the structure of the ligand/educt 2pzoap has not been reported [4], [5], [6], [7]. As shown in the figure, the compound 1 crystallizes in the monoclinic space group P2/n with the title molecule located on a twofold axis and a methanol molecule in general position. The bond lengths of N3 = C5, N2—C4 and C3—N1 are 1.281, 1.344 and 1.338 Å, respectively, which are similar with the reference [8].

Acknowledgements

The authors gratefully acknowledge the financial support by National Undergraduate Training Program for Innovation and Entrepreneurship (201911736006) Science Foundation of Shaanxi Province of China (2016JQ2001) and Young Talent fund of University Association for Science and Technology in Shanxi, China.

References

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Received: 2019-08-15
Accepted: 2019-10-02
Published Online: 2019-10-14
Published in Print: 2019-12-18

©2019 Fang Xiangqing 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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  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
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  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  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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