In
this report, the occurrence of three-, two-, and one-dimensional
(3D, 2D, and 1D) isostructurality in phenyl benzoate (D00) and their
fluorinated analogues was investigated in terms of their molecular
assembly in solid state structures. A one-dimensional C–H···OC
chain is observed as a robust motif (∼ −21 kJ/mol) in
the formation of the supramolecular architectures in these isostructural
compounds. The isomorphous crystal structures exhibit 3D isostructurality
or vice versa. The crystal packing shows that weak intermolecular
C–H···F, C–H···O, C–H···π
interactions, and π···π stacking are the
main contributors providing stability toward the crystal lattice.
The nature and energetics of all the geometrically or energetically
equivalent building blocks associated with similar or different intermolecular
interactions delineate the role of different molecular pairs in the
crystal structures. The fingerprint plots of the isostructural set
of crystal structures help to understand the similarities and the
differences in the various interatomic contacts. A comparison of these
crystal structures with fluorinated N-phenyl benzamides
shows the change in supramolecular assembly in terms of intermolecular
interactions as well as the lattice energy due to the participation
of a strong donor (N–H).