CRYSTALLOGRAPHIC ARCHITECTURE AND PHARMACOLOGICAL POTENTIAL OF N, N’-BIS[(2-METHYLPHENYL) SULFONYL] ADIPAMIDE: STRUCTURAL INSIGHTS, CONFORMATIONAL ANALYSIS, AND SULFONAMIDE DRUG-LIKENESS PROFILING

Abstract

The present study reports a comprehensive single-crystal X-ray diffraction (SCXRD) investigation of N,N’-Bis[(2-methylphenyl) sulfonyl] adipamide, a sulfonamide compound with the molecular formula C₂₀H₂₄N₂O₆S₂ and molecular weight 452.53 g/mol. The compound crystallizes in the monoclinic crystal system, space group P 21/n (No. 14), with unit cell parameters a = 11.928(2) Å, b = 5.523(1) Å, c = 16.447(4) Å, β = 96.05(2)°, and Z = 2. Structure solution and refinement were performed using SHELXS-97 and SHELXL-97, converging to R₁ = 0.0758 [I > 2σ(I)] and wR₂ = 0.1301. The asymmetric unit contains one-half of the molecule, which resides on a crystallographic inversion center. A detailed geometric analysis reveals the tetrahedral geometry around the sulfonyl sulfur (S1), amide planarity at the N1–C7 linkage, and a characteristic intramolecular N–H···O hydrogen bond [N1–H1N···O1: D···A = 2.917(4) Å, ∠DHA = 166°] that stabilizes the molecular conformation. Torsional analysis identifies a near-planar arrangement of the sulfonamide group. Anisotropic displacement parameters, bond length and angle comparisons with reference values, and crystallographic refinement statistics are discussed in detail. The physicochemical and drug-likeness profiles evaluated through Lipinski's Rule of Five suggest moderate pharmaceutical potential, particularly as an antibacterial or anti-inflammatory lead compound. Hirshfeld surface analysis and energy framework discussions further illuminate the packing motifs dominated by N–H···O and C–H···O interactions.