title: Vibrational spectra, crystal structure, DFT quantum chemical calculations and conformation of the hydrazo-bond in 6-methyl-3-nitro-2-(2-phenylhydrazinyl)pyridine.
abstract: The crystal and molecular structures of 6-methyl-3-nitro-2-(2-phenylhydrazinyl)pyridine (6-methyl-3-nitro-2-phenylhydrazopyridine) have been determined by X-ray diffraction and quantum chemical DFT analysis. The crystal is monoclinic, space group C2/c, with Z=8 formula units in the elementary unit cell of dimensions a=16.791(4), b=6.635(2), c=21.704(7)Å, β=100.54(3)°. The molecule consists of two nearly planar pyridine subunits. A conformation of the linking hydrazo-bridge CNHNHC is bend and the dihedral angle between the planes of the phenyl and pyridine rings is 88.2(5)°. The hydrogen bonding of the type NH···N and possibly also CH···O favors a dimer formation in the crystal structure. The dimers are further linked by a NH···O hydrogen bond, so forming a layer parallel to the ab plane. The molecular structure of the studied compound has been determined using the DFT B3LYP/6-311G(2d,2p) approach and compared to that derived from X-ray studies. The IR and Raman wavenumbers have been calculated for the optimized geometry of a possible monomer structural model but the possibility of the dimer formation through the NH···N hydrogen bond has also been considered. The structural and vibrational properties of the intra-molecular NH···O interaction are described.
authors: Department of Bioorganic Chemistry, Institute of Chemistry and Food Technology, Faculty of Engineering and Economics, Wrocław University of Economics, Wrocław, Poland.
authors: E
authors: E
authors: Kucharska
authors: J
authors: J
authors: Michalski
authors: W
authors: W
authors: Sąsiadek
authors: Z
authors: Z
authors: Talik
authors: I
authors: I
authors: Bryndal
authors: J
authors: J
authors: Hanuza
mesh_terms: D018360:Crystallography, X-Ray; D019281:Dimerization; D006834:Hydrazines / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D011725:Pyridines / Q000737:chemistry*; D011789:Quantum Theory; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman
chemical_list: C583254:6-methyl-3-nitro-2-(2-phenylhydrazinyl)pyridine; D006834:Hydrazines; D011725:Pyridines