This undated photo provided by the Alabama Department of Corrections shows Ronald Bert Smith Jr.. Smith Jr., an Alabama inmate coughed repeatedly and his upper body heaved for at least 13 minutes during an execution, Thursday, Dec. 8, 2016, using a drug that has previously been used in problematic lethal injections in at least three other states. (Alabama Department of Corrections via AP, File)

Alabama has put Ronald Bert Smith Jr. to death after the U.S. Supreme Court temporality halted lethal injection twice in a two-hour period the day of execution, Thursday, Dec. 8, 2016.

Smith was convicted of the 1994 killing of a convenience store clerk, Casey Wilson. The prosecution said Smith pistol-whipped the clerk when he wouldn’t open the cash register, and then shot him in the head. A jury recommended life in prison by a 7-5 vote, but an Alabama judge overrode that recommendation and sentenced Smith to death. Thanks to the U.S. Supreme Court’s January 2016 ruling in Hurst v. Florida, this practice is no longer allowed is any state—other than Alabama.

On Thursday afternoon at approximately 5 p.m., according to the Associated Press, Smith’s attorney’s made the argument to both the governor of Alabama and the U.S. Supreme Court that the judge’s override of the jury as fundamentally unfair.

Gov. Robert Bentley refused to interfere, but the U.S. Supreme Court issued a temporary stay around 6 p.m. Supreme Court Justice Clarence Thomas indicated the stay was to provide extra time for the justices to consider Smith’s halted execution request.

Even before this case, the state of Alabama was under orders from the U.S. Supreme Court to reconsider the question of if their death penalty law violates Hurst, which says it is a violation of the Sixth Amendment to not have a jury determination of all facts necessary to impose the death penalty. There is also a national consensus against judicial disregard of jury recommendation in capital sentencing verdicts. The nation’s highest court recently overturned four decisions of the Alabama court of criminal appeals, and sent the cases back to the state to reconsider the issue.

On Thursday, the Smith case would not become a fifth.

At about 7:30 p.m., the U.S. Supreme Court said the execution of Smith could proceed. Four liberal judges said they would have voted to grant the stay.

Smith’s lawyers immediately asked the court to reconsider, criticizing the rule that allows four votes to grant review of a case but requires five to stay an execution as arbitrary, according to the Death Penalty Information Center.

Justice Thomas granted another temporary stay so the full Court could consider the newest motion; but still denied the request after about an hour.

At the same time, the U.S. Supreme Court also rejected a last-minute challenge to Alabama’s lethal injection procedure, as Smith is also part of a group of death row inmates challenging the state’s use of midazolam, a sedative that has been involved in several botched executions over the last few years.

The most recent and notable was the January 2014 execution of Dennis McGuire in Ohio. McGuire repeatedly gasped and snorted during a 26-minute execution using a never-before-tried two-drug combo that utilized midazolam as the sedative.

Alabama uses midazolam as a sedative as well, but they do so in a three-drug protocol. However, during Smith’s execution, he heaved, coughed, clinched his fist, raised his head, and opened one eye. The Associated Press reports Smith heaved and coughed for 13 minutes during the 30-minute-long execution. Additionally, when the prison guard performed the first of two consciousness checks before administering the lethal drugs, Smith moved his arm.

The 45-year-old Smith was pronounced dead at 11:05 CST Thursday.