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4-(2-Fluorophenyl)-7-methoxycoumarin ( 6 ) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1 H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 ( J  FH = 2.6 Hz) and 13 C NMR suggested that this C-F···H-C coupling is a through-space interaction. The 2D 19 F-{ 1 H} HOESY and 1 H-{ 19 F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C-F···H-C interaction.

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds