Study of H-bonded assemblies of the solvates of anthracene derivatives: guest effect on the crystal symmetry and spectroscopic properties

Two solvates of title compound 1-acetyl-3-naphthyl-5-(9-anthryl)-2-pyrazoline solvate(ANNP) (1a) with chloroform (1b) and acetic acid (1c) and a single crystal of another title compound 1-acetyl-3-(4-chloro)phenyl-5-(9-anthryl)-2-pyrazoline (ACAP) (2a) and its adduct with phenol (2b) were afforded via solution growth technique. The structure of these solids were confirmed and verified by multiple techniques such as single crystal X-ray diffraction (SCXRD) analysis, PXRD, DSC/TGA and Infrared spectroscopy. Structural analysis indicates that guest inclusion results not only in stronger hydrogen bonds, but also in a larger number of favourable C–H?π interactions between ANNP/ACAP molecules. The solvates show symmetry reduction guest effect comparing with the guest free molecules of ANNP and ACAP. Moreover, characteristic changes have been observed in the Infrared bands of the solvates owing to the formation of hydrogen bonds between host–guest.