Crystallography and computational electronic structure investigations on 14-(3, 4, 5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene

Abstract

The crystal structure and Hirshfeld surface analysis of 14-(3, 4, 5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene (DBX) was examined and reported in the present work. The DBX was identified as triclinic system with P-1 space group. The unit cell parameters found to be, a=13.9419(2)Å, b=14.1503(2)Å, c=20.2765(3)Å, α=85.892(1)°, β=87.098(1)°, γ=61.487(1)°, V=3505.36(9), Z=6 respectively. Three symmetrically independent DBX molecules were present in the asymmetric unit. The structural superimposition study shows that the molecule A and B in same conformation, whereas molecule C in opposite conformation. The pyran ring in xanthene core is almost perpendicular to that of 3,4,5-trimetoxyphenyl substituent. Similarly, the same pyran ring of the xanthene core in molecule A, B and C has arranged in boat conformation. The solid state structure has been stabilized by weak C–H⋯O and C–H⋯π interactions. Hirshfeld surface analysis with two-dimensional fingerprint plots shows that the relative contributions of H⋯H; C⋯H/H⋯C; O⋯H/H⋯O and C⋯C intermolecular contacts involving various atoms are comparable in these three structures. The computational electronic structure calculation on DBX starts with geometry optimization and it is extended to prediction of vibrational frequencies, Natural Bond Orbital analysis (NBO), Frontier Molecular Orbital calculation (FMO), Thermochemical inspection and Molecular Electrostatic Potential (MEP) studies. The entire quantum chemical calculation has been carried out by using Density Functional Theory based B3LYP/6-31G(d,p) model chemistry.