The synthetic protocol and solid state characterization of two new coumarin-pyrazolylthiazole hybrids (1-2) are detailed in this manuscript. Synthesized compounds were characterized applying nuclear magnetic resonance, Fourier-transform infrared spectroscopy and single-crystal X-ray diffraction techniques. A detailed structural analysis of 3- 2) is reported along with a detailed description of the noncovalent interactions and their evaluation using Hirshfeld surface analysis, emphasizing the structure-directing role of CÀ H⋅⋅⋅O, Br⋅⋅⋅π and π-π interactions. Finally, DFT energetics, molecular electrostatic potential (MEP), quantum theory of "atoms-in-molecules" (QTAIM) and noncovalent interaction plot (NCIplot) index computations have been used to further investigate the relative importance of two different π-stacking complexes observed in the solid state of both compounds, which are recurrent binding motifs in their crystal packing.