Title:	Crystal structure, Hirshfeld surface analysis, DFT and mol­ecular docking studies of 4′-(benz­yl­oxy)-[1,1′-biphen­yl]-3-carb­­oxy­lic acid
Authors:	Kumar, M. Harish Vinduvahini, M. Srinivasa, H. T. Devarajegowda, H. C. Palakshamurthy, B. S.
Keywords:	crystal structure Hirshfeld surface DFT studies mol­ecular docking benz­yloxy biphenyl carb­oxy­lic acid
Issue Date:	1-Mar-2025
Publisher:	International Union of Crystallography
Abstract:	In the title compound, C20H16O3, intra­molecular C— H⋯O hydrogen bonds are observed. The dihedral angles between the aromatic benzoic acid ring and the two adjacent aromatic rings are 26.09 (4) and 69.93 (8)°, while the dihedral angle between the aromatic rings connected by the C—O—C—C [torsion angle = −175.9 (2)°] link is 89.11 (3)°. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R22(8) ring motifs. These dimers are further linked by C—H⋯π inter­actions, forming mol­ecular sheets along (010). The mol­ecular structure was optimized by density functional theory (DFT) at the B3LYP/6–311+ G(d,p) level and the bond lengths, angles and torsion angles were compared with experimental values obtained by X-ray diffraction. The HOMO and LUMO were calculated, the energy gap between them being 4.3337 eV. Further, the inter­molecular inter­actions were qu­anti­fied using Hirshfeld surface analysis and fingerprint plots and energy frameworks were generated. The two-dimensional fingerprint plots indicate that the major contributions to the crystal packing are from H⋯H (39.7%), H⋯C (39.0%) and H⋯O (18.0%) inter­actions. The energy framework calculations reveal that the dispersion energy (Edis= 201.0 kJ mol−1) dominates the other energies. Mol­ecular docking studies were carried out for the title compound as a ligand and the SARS-Covid-2 (PDB ID:8BEC) protein, specifically the Omicron variant, was used as a receptor giving a binding affinity of −7.6 kcal mol−1.
Description:	Open Access
URI:	http://hdl.handle.net/2289/8375
Alternative Location:	https://doi.org/10.1107/S2056989025001021
Copyright:	2025 The Author(s)
Appears in Collections:	Research Papers (SCM)

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