Structure elucidation of 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C₂₃H₁₈Cl₂N₄OS from synchrotron X-ray powder diffraction

Abstract

The 3-[1-(6-methoxy-2-naphtyl)ethyl]-6-(2,4-dichlorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine, C23H18Cl2N4OS compound was synthesized, as a member of the family of novel potential anticancer agents. The structure of the title compound was characterized by IR, 1H-NMR, mass spectroscopy, and elemental analysis, previously. In this study, the crystal structure of this compound has been determined from synchrotron X-ray powder diffraction data. The crystal structure was solved by simulated annealing and the final structure was achieved by Rietveld refinement method using soft restrains on all interatomic bond lengths and angles. This compound crystallizes in space group P21, Z = 2, with the unit-cell parameters a = 15.55645(11) Å, b = 8.61693(6) Å, c = 8.56702(6) Å, β = 104.3270(4)°, and V = 1112.68(1) Å3. In the crystal structure, strong C−H⋯π and weak intermolecular hydrogen-bonding interactions link the molecules into a three-dimensional network. The molecules are in a head-to-head arrangement in the unit cell.

Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Four Extra Heteroatoms 2:2

“…Atom  (ppm) J (Hz) C(7') 13.4 The 19 F NMR data of newly synthesized 3-fluoro [1,2,4]triazolo [5,1-c][1,2,4]triazin-4(1H)-one derivatives 33 have been reported. A significant downfield shift has been noticed for 33 (from -114 to -115 ppm) compared to triazolopyrimidinones 34 (from -169 to -171 ppm) which has been rationalized by the electron-withdrawing effect of the triazine nitrogen atom N2 (Figure 3).…”

“…For the latter, the dihedral angle between the bicyclic system and the 2,4dichlorophenyl substituent is 50.74°. [18][19] <Figure 5 near here>…”