An N-Substituted 1H-indole derivative having an empirical formula C₁₆H₁₃NO₃S was synthesized by the condensation of 2-Methyl-1H-Indole-3-carbaldehyde and benzene sulfonyl chloride in presence of a phase transfer catalyst of type quaternary ammonium salt in basic conditions. Then the compound was characterized by using FT-IR, UV–Visible and NMR spectroscopic methods. Thus the obtained experimental results were effectively compared with DFT studies in arriving the structural characteristics of the title compound. From vibrational analysis, it was observed that carbonyl frequency is somewhat lower than a typical aldehydic stretching frequency and it could be possible only when the formyl group is coplanar with the ring and subsequent resonance conjugation reduces its force constant. Similarly, the optical absorption behavior of a typical indole ring suffered from a bathochromic shift due to the presence of ring substituents. Finally, the molecular drug docking studies of the title compound were performed using AutoDock 4.2 tools to ascertain its binding mode, efficiency and the nature of chemical interactions with the target proteins and it has been predicted theoretically that the binding efficiency of the ligand on the target receptor surface was found to be better in the case of Gram positive bacteria S. Aureus than the Gram negative N. Meningitidis.