Redetermination and Density Functional Studies of N,N′-(Disulfanediyldibenzene-2,1-Diyl) Dipyridine-2-Carboxamide
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The title compound C24H18N4O2S2 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) Å3. 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.
Keywordsstructural analysis acyl azide density functional theory NBO analysis
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- 3.G. M. Sheldrick. Acta Crystallogr., 2015, C71, 3–8.Google Scholar
- 5.O. D. Rigaku. CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England, 2015.Google Scholar
- 6.R. C. Clark and J. S. Reid. Acta Crystallogr., 1995, A51, 887–897.Google Scholar
- 8.M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, et al. Gaussian 09, Revision B.01. Gaussian, Inc., Wallingford, 2010.Google Scholar
- 10.F. H. Allen. Acta Crystallogr., 2002, B58, 380–388.Google Scholar
- 11.A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, and R. Taylor. J. Chem. Soc. Dalton Trans., 1989, SI–S83.Google Scholar
- 12.J. D. Lee and M. W. R. Bryant. Acta Crystallogr., 1970, B26, 1729–1735.Google Scholar
- 14.A. Szabo and N. S. Ostlund. Modern quantum chemistry: introduction to advanced electronic structure theory. Dover, Mineola, 1996.Google Scholar