A federal judge has dismissed civil charges against three Woodbury police officers who mistakenly shot a 19-year-old St. Paul man as he fled from his hostage-taker at a Woodbury motel in 2012.

On Thursday, a U.S. District Court judge determined the officers acted reasonably and granted their defense attorney’s request to dismiss a civil lawsuit filed by the family of Mark Eric Henderson. The suit alleged wrongful death, excessive force and indifference of Henderson’s civil rights.

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Police shot Henderson after he escaped from Demetrius S. Ballinger, then 25, who had been holding 11 young people at gunpoint at the Woodbury Red Roof Inn motel on Aug. 31, 2012.

U.S. District Judge Richard H. Kyle previously issued a notice deeming the case ready for a jury trial this March. But defense attorneys filed a motion Nov. 10, 2016, arguing that the case should be dismissed.

In his decision, Kyle wrote that a jury wouldn't be able to conclude if the use of police force was unreasonable. He also affirmed the officers were entitled to qualified immunity, which shields government officials from lawsuits when there is uncertainty if their actions were legal.

“The facts of this case are undeniably tragic, and the Court is sympathetic to the loss Tawana (Henderson) and all of Mark’s family have sustained,” Kyle wrote. “The narrow question before the Court is whether the officers acted reasonably. In the Court’s view, the evidence points to only one answer: Yes.”

Attorneys for the Henderson family said they plan to appeal the court’s ruling, and argued officers' retelling of events differs from what they said the night of the incident. They also argue Henderson complied with police orders when he went to the ground.

"Ms. Henderson is disappointed by the ruling that there should not be a trial regarding her unarmed 19-year-old son's death," attorney Ashwin Madia said. “We plan on appealing the decision.”

The suit named Woodbury officers Anthony Ofstead, Stacey Krech and Natalie Bauer, who were involved in the shooting and have been with the department since 2000, 2007 and 2008, respectively, according to their résumés.

Joseph Flynn, who represented the officers, said while the facts of the case were tragic, officers acted properly in making a split-second decision.

"I think the jury would have looked at it the exact same way the judge did," Flynn said.

According to court documents, Ballinger drove Henderson and a group of friends to the Red Roof Inn where they had planned to attend a party on the night of the incident. When his car overheated, he reportedly became frustrated and decided to rob everyone in the room at gunpoint “just for something to do.”

After officers arrived at the motel, Ballinger pointed a gun through the window at Bauer, who noted he was wearing a green shirt.

According to court documents, officers heard a shot come from the room -- which was later found to have been fired by Ballinger -- as Henderson ran out of the room.

Henderson, who was wearing a white shirt, ran toward the officers and slowed down when they ordered him to freeze and show his hands, according to court records.

Believing the shot came from Henderson, officers said they began firing after ordering him to stop.

When he went to the ground, officers testified that they weren’t able to see his right hand as he laid in a prone position and continued firing.

Attorneys for the Henderson family argue police gave contradicting commands while Henderson was on the ground by telling him to not move and show them his hands.

Officers fired a total of 17 shots, striking Henderson a dozen times, according to a Minnesota Bureau of Criminal Apprehension investigation. Witnesses told investigators they heard him say, “I can’t believe you shot me.”

Henderson died shortly after being transported to Regions Hospital in St. Paul.

An autopsy found a bullet fired from Ballinger’s gun lodged in Henderson’s right arm. A Ramsey County medical examiner ruled his death was from multiple gunshot wounds.

Ballinger pleaded guilty to attempted murder and four counts of first-degree criminal sexual conduct for sexually assaulting four minors. He is serving a 36-year prison sentence.

A Washington County grand jury cleared Bauer, Ofstead and Krech of any criminal charges in 2013.

Attorneys for the Henderson family have 30 days to file an appeal.