Abstract
Crystal structures of six benzaldehyde derivatives (1–6) have been determined and their supramolecular networks were established by an X-ray crystallographic study. The study has shown that the compounds are linked by various intermolecular interactions such as weak C–H⋯O hydrogen bonding, and C–H⋯π, π–π and halogen bonding interactions which consolidate and strengthen the formation of these molecular assemblies. The carbonyl group generates diverse synthons in 1–6via intermolecular C–H⋯O hydrogen bonds. An interplay of C–H⋯O hydrogen bonds, and C–H⋯π and π–π stacking interactions facilitates the formation of multi-dimensional supramolecular networks. Crystal packings in 4 and 5 are further generated by type I halogen⋯halogen bonding interactions. The differences in crystal packing are represented by variation of substitution positions in the compounds. Structure 3 is isomorphous with 4 but there are subtle differences in their crystal packing. The nature of intermolecular contacts in the structures has been studied through the Hirshfeld surfaces and two-dimensional fingerprint plots which serve as a comparison in constructing different supramolecular networks. The intermolecular interaction energies are quantified utilizing theorectical calculations for the title compounds and various analogous structures retrieved from the Cambridge Structural Database (CSD). Also intermolecular interactions for the molecular pairs are exctrated from respective crystal structures. Essentially, there are some invariant and variable intermolecular contacts realized between different groups in all six structures. The ab initio DFT total lattice energy (ETot) calculations showed a direct correlation with thermal strengths of the title compounds.
Highlights
Crystal engineering of supramolecular networks linked via intermolecular contacts continues to be a dynamic topic in the solid-state studies of self-assembly.[1]
We have demonstrated that weak intermolecular contacts are stronger for benzyloxybenzaldehydes than their analogous structures reported by Chattopadhyay.[4]
In our effort to explore the role played by these intermolecular contacts in the self-assembly of crystal structures we have studied six related benzaldehyde derivatives by single crystal X-ray diffraction
Summary
Crystal engineering of supramolecular networks linked via intermolecular contacts continues to be a dynamic topic in the solid-state studies of self-assembly.[1]. 50 kJ molÀ1.2 Intermolecular contacts or weak interactions (#15 kJ molÀ1) such as C–H/p, hydrogen/halogen bonds and p–p stacking are well-known to signi cantly in uence the molecular assembly in organic compounds.[3] Numerous synthons that incorporate intermolecular contacts such hydrogen/ halogen bonds, C–H/p, lone pair–p and p–p stacking interactions signi cantly affect robustness to produce molecular solids with promising properties.[4] Halogen bonding interactions established in many halogen-containing organic crystals are believed to enhance crystal stability.[5] Essentially, these intermolecular contacts are said to be independently weaker and geometrically less well-de ned, but their combined effect can be important as strong interactions.[6] It is useful to study the diversity of hydrogen-bonding systems in molecules that contain a rigid benzyloxy core with different positions of substituents, and to explore their structural features including interplay of intermolecular contacts in building the possible supramolecular networks.[7] It is of interest to explore the role of these intermolecular contacts in the molecular assembly of halogen-substituted (benzyloxy)benzaldehydes. An additional interest in the (benzyloxy)benzaldehyde moiety lies in its anticancer activity against HL-60 cells[8] and serves as important
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