Two novel fluorine-containing cyclophanes 1 and 2 incorporating a 1,4-bismethylfluorophenylene subunits have been synthesized via the template-directed clipping methodology and their structure was characterized by 1H NMR, 13C NMR, MALDI-TOF-MS and elemental analysis. X-ray diffraction analysis of the solid state molecular structure showed that the complex units are linked by non-classical C-H…F hydrogen bonding.