On July 14, 2015 about 1456 central standard time, a Cessna 182B airplane, N2764G, registered to Cook Aviation of St. Louis, Missouri, was substantially damaged when it impacted terrain after the pilot bailed out (via donned parachute) due to flight control problems. There were no occupants on board when the airplane impacted the terrain. The sky dive flight had been conducted under the provisions of Title 14 Code of Federal Regulations Part 91 prior to the bail out. Visual meteorological conditions prevailed throughout the area and no flight plan was filed. The flight departed from the Festus Memorial Airport (FES), Festus, Missouri, about 1415. The pilot picked up four skydivers at FES. After climbing to 3,800 ft, one of the skydivers deployed, and at 11,000 ft, the remaining three skydivers deployed. According to the pilot's statement, the procedure for deploying skydivers was to input 10° of flaps prior to the skydivers' deployment. After the last skydiver exited the airplane, the pilot closed the door and started to retract the flaps from 10° to 0°. The pilot heard a "metallic" type snap noise and the airplane went into a spin. The pilot recovered the airplane from the spin about 7,000 ft. He discovered that the right flap was partially deployed about 5° down and appeared to be crooked in its track. In addition, he reported that there seemed to be a vibration present from the right flap with restricted aileron control. The pilot stated that lateral control was difficult to maintain. On the airplane radio, the pilot contacted an airframe and powerplant (A&P) mechanic, who was based at FES, to discuss the flap malfunction. The pilot then attempted to execute a straight-in landing at FES, but initiated a go-around when he was not able to maintain lateral control as the airplane slowed on approach. After attempting to change the flap position, only the right left flap responded and the right flap stayed in the 5° position. After 30 minutes of trying to control a slow spin, it was determined between the pilot and the A&P mechanic that the pilot should bail out of the airplane. The pilot then maneuvered the airplane over unpopulated rural farmland to the east of FES. The pilot parachuted from the airplane after shutting down the engine. The pilot watched the airplane circle around him after his parachute deployed. The airplane impacted a bluff with no post impact fire. The pilot sustained no injuries from the event. Examination of the wreckage revealed that the top outboard section of the right showed evidence of pre-impact contact with the bottom inboard side of the right aileron. There was about 1/2 inch of rubbed exposed primer in the area of the contact. The right flap appeared to be misaligned in its track, and the outboard portion of the flap would not freely extend from the retracted position. The outboard side of the flap was retracted and the inboard side was extended in the track. There was a broken control cable inboard of the flap bell crank that was found dirty and rusty in the area of the break. The right flap showed pre-impact evidence of contact with the right aileron. Due to impact forces, the pre-impact condition of the flap rollers and tracks could not be determined. A review of maintenance records did not show any recent work performed on the flap control system. The airplane had an annual inspection completed on May 18, 2015, and had flown about 80 hours since that inspection.