Two new coordination compounds of Mn(II) and Cu(II) viz. [Mn(bz)2(Hdmpz)2(H2O)] (1) and [Cu(crot)2(Hdmpz)2] (2) (where, bz = benzoate, crot = crotonate, Hdmpz = 3, 5-dimethyl pyrazole) have been synthesized and characterized using single crystal X-ray diffraction technique, FT-IR, electronic spectroscopy, TGA and elemental analyses. Compounds 1 and 2 crystallize as mono-nuclear coordination compounds of Hdmpz based penta-coordinated Mn(II) and hexa-coordinated Cu(II) respectively containing distorted trigonal bipyramidal and distorted octahedral geome-tries. Crystal structure analysis of compound 1 reveals the presence C‒H⋯π and π-stacking in-teractions along with O‒H⋯O, N‒H⋯O and C‒H⋯O H-bonding interactions which stabilizes the layered assembly of the compound. Similarly, the presence of hydrogen bonding along with π-stacking interactions stabilizes the crystal structure of compound 2. We have carried out theo-retical investigations to analyze π⋯π H-bonding and antiparallel CH···π non-covalent interac-tions observed in the compounds. DFT calculations were performed to evaluate strength of these interactions energetically. Moreover, QTAIM and non-covalent interaction (NCI) plot index computational tool were used to characterize them and evaluate the contribution of the H-bonds.