Molecular Dynamics-simulated OH···O bonded-cyclic dimer structure, called D_c, has been proposed for 2,5-Dihydroxyterephthalic acid a potential organic linker in Hydrogen-bonded Organic Frameworks (HOF). Among many dimer species bound by inter-molecular OH···O bonds, D_c was chosen because of its relatively highest lifetime of 18.3 ps as indicated by the radial distribution functions (RDF). Experimentally observed intense but broad down-shifted IR absorptions peak at ∼ 3023 cm⁻¹ and bands near 2556 cm⁻¹ combined with staggered occurrence of IR and Raman bands in other spectral regions suggested that the proposed cyclic dimer appeared to possess an extended quasi-centrosymmetric configuration. Upon optimization of D_c at B3LYP/6-311++G(d,p) level, it yielded geometry and vibrational spectra in agreement with experimental spectra. Further, we have characterized both intra- and inter-molecular OH···O bonds in D_c using stabilization energy E⁽²⁾ and other molecular orbital (MO) properties from NBO analysis. Bond critical points (BCPs) and ring critical points (RCPs) deduced from electron density (ρ(r)), its laplacian (${\nabla }^2\rho \left(r\right)$) and potential energy density (v(r)) using AIM calculations have provided complementary perspectives. Additionally, a combination of quantitative analysis and graphical visualization of the charge regions where non-covalent interactions occur in real space intra- and inter-molecular OH···O bonds, van der Waals and repulsive steric clash interactions have been obtained from NCI calculations.