Clusters of the cyanocyclopentadienyl (CNcpd) radical and several polar solvent molecules (e. g., CF2H2, CF3H, CF3Cl, CH3Cl, ROH, H2O) created in a supersonic jet expansion are studied by laser induced fluorescence and hole burning spectroscopies. Lennard-Jones-Coulomb atom-atom potential energy calculations are employed in combination with ab initio calculations to aid in the interpretation of the observed spectra and to understand the nature of the radical polar solvent solvation behavior. The calculations predict quite reasonable cluster binding energies and structures, but are less accurate in predicting van der Waals vibrational mode energies and cluster spectroscopic shifts. The limitations of the atom-atom potential energy surface model in dealing with the more subtle aspects of CNcpd-polar solvent intermolecular interactions are discussed. Some possible causes of inadequacies of the approach are presented.