The valence excited electronic states and the circular dichroism (CD) spectra of the recently synthesized 12,15-dichloro[3.0]orthometacyclophane 1 are discussed by means of quantum chemical calculations which combine density functional theory with the single-excitation configuration interaction approach (DFT/SCI). The X-ray structure of this highly strained biphenylophane is presented. In order to investigate the influence of the cyclophane-type distortions on the CD spectrum of 1, the CD spectra of three model geometries (2a-2c) are also calculated. It appears that the CD spectrum of the biphenylophane 1 differs substantially from that of the corresponding unstrained biphenyl 2c. Furthermore, it is found that the pyramidalization of the bridging atoms of the cyclophane ring is an important factor for the red shift of the first band with respect to that of an unstrained benzene chromophore.