Crystal Structure, Hirshfeld Surfaces and Energy Framework Studies of a Biologically Active Compound (3E)-3- (2,4- dimethoxybenzyldene) -2,3-dihydro- 4H-chromen-4-one
J. Hemalatha
PG and Research Department of Physics, Queen Mary’s College (A), Chennai-4. Affiliated to the University of Madras, Chennai-600004, Tamil Nadu, India.
D. Reuben Jonathan
Department of Chemistry, Madras Christian college (A), Chennai-59. Affiliated to the University of Madras, Chennai-600004, Tamil Nadu, India.
D. Angeline Shirmila
PG and Research Department of Physics, Queen Mary’s College (A), Chennai-4. Affiliated to the University of Madras, Chennai-600004, Tamil Nadu, India.
M. Krishna Priya
PG and Research Department of Physics, Queen Mary’s College (A), Chennai-4. Affiliated to the University of Madras, Chennai-600004, Tamil Nadu, India.
K. Laavanya
Department of Physics, DG Vaishnav college (A), Chennai-106, Affiliated to the University of Madras, Chennai-600004, Tamil Nadu, India.
G. Usha *
PG and Research Department of Physics, Queen Mary’s College (A), Chennai-4. Affiliated to the University of Madras, Chennai-600004, Tamil Nadu, India.
*Author to whom correspondence should be addressed.
Abstract
A new chalcone derivative (3E)-3-(2,4-dimethoxybenzyldene)-2,3-dihydro-4H-chromen-4-one (DBDB) has been synthesized by following the Claisen-Schmidt condensation reaction method at ambient temperature using the slow evaporation technique. The 3D crystal structure was solved using the single-crystal X-ray diffraction method (XRD). XRD intensity data reveal that the title compound crystallizes in an orthorhombic crystal system with non-centrosymmetric space group P21 21 21. The crystallographic parameters such as bond lengths, bond angles, torsion angles were estimated and are found to be in the normal range and comparable with the literature values. The unit cell packing of the molecules shows that the adjacent molecules are linked via C-H…O hydrogen bonds. Hirshfeld surfaces namely dnorm, electrostatic potential, shape index, and curvedness were analyzed to visualize and to evaluate the weak intermolecular interactions, positive and negative potential regions, C-H…π, and π…π stacking interactions, respectively. The 2D fingerprint plots for the whole and delineated interactions were generated and analyzed to estimate their contributions to the total Hirshfeld surfaces. The pairwise intermolecular interactions were calculated as the sum of four scaled energy components namely electrostatic (Eele), polarization (Epol), dispersion (Edis), and exchange-repulsion (Erep) and graphically represented as energy frameworks. The energy frameworks analysis reveals that the total stabilizing energy is highly influenced by dispersion (Edis) energy than the other components. In-vitro and in-silico investigations have also been performed for the title molecule which discloses the efficacious for use as a drug in inhibiting breast cancer cells without affecting the normal cells.
Keywords: Claisen-Schmidt condensation reaction, Hirshfeld surfaces, 2D fingerprint plots, Biological activity, In-vitro investigation, Cytotoxicity, Molecular docking, Anti-cancer activity evaluation