The dynamic behavior of an ion flow around an obstacle in a collisionless plasma is investigated. The obstacle consists here of an absorbing cylinder, and a 2 dimensional electrostatic particle-in-cell simulation is used to study the flow characteristics. The formation of irregular filamented density depletions, oblique to the flow, is observed. The dynamics of these structures depend on the physical parameters of the plasma. The structures form at the edges of the wake behind the obstacle, in a region with a strong velocity shear, and are found to be associated with phase-space vortices, observed specially in the velocity direction perpendicular to the flow. The results can be of interest in the interpretation of structures in space plasmas as observed by instrumented space crafts.