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<p>The role of weak intermolecular interactions in directing the molecular assembly and solid-state architecture is crucial in the design of functional organic materials. In this study, two fluorinated (<i>E</i>)-<i>N</i>-benzylbut-2-enamide derivatives were synthesized, and their solid-state structures were investigated using single-crystal X-ray diffraction. Furthermore, these two compounds were also characterized using powder X-ray diffraction, NMR spectroscopy, and Differential Scanning Calorimetry (DSC). The crystal packing investigation demonstrates that both the crystal structures form one-dimensional N–H···O hydrogen-bonded chains, further stabilised by weak C–H···F and C–H···O intermolecular interactions, which collectively support the three-dimensional supramolecular architecture in molecular solids. The interaction energy calculations using PIXEL provide quantitative insights to identify and evaluate the nature and strength of non-covalent interactions, including C–H···F, C–H···O, C-H···π, and non-specific close contacts. Additionally, the contributions of different interatomic contacts are elucidated through Hirshfeld surface analysis and associated two-dimensional fingerprint plots, while the electrostatic potential (ESP) mapping provides insights into the charge distribution on molecular surfaces and reveals potential hydrogen bond acceptor regions. Overall, the analysis shows that the position of fluorine substituents significantly influences the interaction landscape and overall crystal architecture.</p>

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Quantitative analysis of weak interactions in the solid state structures of fluorinated (E)-N-benzylbut-2-enamides

  • 期刊论文

  • 发表日期：

    2025年12月29日

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  • Dhananjay Dey,
  • Arsheen Aijaz,
  • Avantika Hasija,
  • Deepak Chopra

摘要

The role of weak intermolecular interactions in directing the molecular assembly and solid-state architecture is crucial in the design of functional organic materials. In this study, two fluorinated (E)-N-benzylbut-2-enamide derivatives were synthesized, and their solid-state structures were investigated using single-crystal X-ray diffraction. Furthermore, these two compounds were also characterized using powder X-ray diffraction, NMR spectroscopy, and Differential Scanning Calorimetry (DSC). The crystal packing investigation demonstrates that both the crystal structures form one-dimensional N–H···O hydrogen-bonded chains, further stabilised by weak C–H···F and C–H···O intermolecular interactions, which collectively support the three-dimensional supramolecular architecture in molecular solids. The interaction energy calculations using PIXEL provide quantitative insights to identify and evaluate the nature and strength of non-covalent interactions, including C–H···F, C–H···O, C-H···π, and non-specific close contacts. Additionally, the contributions of different interatomic contacts are elucidated through Hirshfeld surface analysis and associated two-dimensional fingerprint plots, while the electrostatic potential (ESP) mapping provides insights into the charge distribution on molecular surfaces and reveals potential hydrogen bond acceptor regions. Overall, the analysis shows that the position of fluorine substituents significantly influences the interaction landscape and overall crystal architecture.