The H-loss products (C6H6N+) from the dissociative ionization of aniline (C6H7N) have been studied by infrared predissociation spectroscopy in a cryogenic ion trap instrument at the free electron laser for infrared experiments (FELIX) laboratory. Broadband and narrow line width vibrational spectra in the spectral fingerprint region of 550-1800 cm-1 have been recorded. The comparison to calculated spectra of the potential isomeric structures of the fragment ions reveals that the dominant fragments are five-membered cyano-cyclopentadiene ions. Computed C6H7N•+ potential energy surfaces suggest that the dissociation path leading to H loss starts with an isomerization process, following a similar trajectory as the one leading to HNC loss. The possible presence of cyano-cyclopentadiene ions and related five-membered ring species in Titan's atmosphere and the interstellar medium are discussed.