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In this communication, we report first on the experimental assessment of fishnet-like metamaterial fabricated by stacking sub-wavelength hole metal arrays. The achievement of a negative refractive index is demonstrated by frequency and angle resolved Time Domain Spectroscopy transmission/reflection experiments for slab and wedge samples operating around 0.5 THz. Then, the studies are extended to chiral metamaterial (twisted motifs) and symmetry breaking devices (half moon apertures).