Redetermination and Density Functional Studies of N,N′-(Disulfanediyldibenzene-2,1-Diyl) Dipyridine-2-Carboxamide

• Published in: Journal of structural chemistry Vol. 59; no. 8; pp. 1797 - 1803
• Main Authors: Yildirim, S. Ö., Büyükmumcu, Z., Dogan, S. D., Butcher, R. J.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-12-2018; Springer Nature B.V
• Subjects: Atomic; Atomic/Molecular Structure and Spectra; Chemistry; Chemistry and Materials Science; Crystal structure; Hydrogen bonds; Inorganic Chemistry; Molecular; Molecular structure; Optical and Plasma Physics; Physical Chemistry; Solid State Physics; structural analysis; acyl azide; density functional theory; NBO analysis
• ISSN: 0022-4766; 1573-8779
• DOI: 10.1134/S0022476618080061

The title compound C
24
H
18
N
4
O
2
S
2
is synthesized via the azide method and its structure is redetermined at 100(2) K. The title structure, N,N′-(disulfanediyldibenzene-2,1-diyl)dipyridine-2-carboxamide is redetermined from the data published by Lumb, Hundal, and Hundal (
Inorg. Chem.
,
2014
, 53, 7770-7779). The redetermination is of significantly higher precision than a previous low-temperature structure and the improvement of the present redetermination consists in a released geometry of the 1,2-diphenyldisulfane group. The molecular structure crystallizes in the triclinic space group,
P
-1, with
a
= 7.3492(3) Å,
b
= 11.6753(5) Å,
c
= 13.1814(6) Å, α = 95.077(4)°, β = 105.316(4)°, γ = 100.759(4)°, and
V
= 1060.28(8) Å
3
. The S–S bond length of 2.0758(4) Å and S–C distances of 1.7818(13) Å and 1.7767(13) Å for this redetermination are much closer to those observed in comparable structures. Intraand intermolecular N–H…S, N–H…N, C–H…O, C–H…S hydrogen bonds are present in the crystal structure. The molecular geometry of the title compound is optimized by the DFT method and the calculated geometrical parameters are compared with experimental ones. The NBO analysis of possible intramolecular hydrogen bonds is made on the optimized structure for comparison.