Isomorphic relationship between three solvates of a ferrocenyl-based chromenopyrimidine

Solvates of 4-((3-ferrocenylphenyl)amino)-5-(2-fluorophenyl)-8,8-dimethyl-5,7,8,9-tetrahydro-6H-chromeno[2,3-d]pyrimidin-6-one (I), a promising antiproliferative agent towards human breast cancer (MCF-7) cells, were formed from their respective acetone, DMSO-d6, and DMF solutions. Isomorphic relationship exists between the solvates of I since all compounds crystallize in a P21/n space group with four molecular entities in their respective unit cells, with slight differences in their respective unit cell parameters. IR spectroscopy was used to distinguish the three solvates by monitoring the N—H vibration frequency since they all have intermolecular N—H...Osolvent hydrogen bonding patterns in the solid state. The solvent molecule's Hirshfeld surface helps distinguish the solvates based on the contribution of reciprocal H…O contacts. Molecular pairwise interaction energy calculations were done to determine the associated energies between solvent-I molecular pairs that are linked by the intermolecular N—H…Osolvent hydrogen bond. Correlations between the geometric parameters of the N—H...Osolvent hydrogen bond, N—H vibration frequency, the contribution of reciprocal H…O contacts toward the solvent's Hirshfeld surface and pairwise interaction energies of the three solvates, are discussed in this work.