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French cement maker Lafarge has pleaded guilty in the US to supporting the Islamic State and other terror groups.
The firm agreed to pay a $777.8m (£687.2m) fine for paying bribes to keep a factory running in Syria after war broke out in 2011.
Prosecutors said it marked the first time a company had pleaded guilty to aiding terrorists in the US.
Lafarge said it "deeply regretted" the events and "accepted responsibility for the individual executives involved".
The cement manufacturer, which was bought by Switzerland's Holcim in 2015, said their behaviour had been in "flagrant violation" of Lafarge's code of conduct.
The firm' opened its plant in Jalabiya near the Turkish border in 2010 following a $680m investment.
But US prosecutors said that Lafarge's Syrian subsidiary had paid Islamic State and another terror group, al Nusra Front, the equivalent of $5.92m to protect staff at the plant as the country's civil war intensified.
Lafarge eventually evacuated the plant in September 2014, when Islamic State took control of the town and the factory.
Lafarge had previously admitted bribes were paid after an internal investigation. But US Deputy Attorney General Lisa Monaco said on Tuesday that the company's actions "reflect corporate crime that has reached a new low and a very dark place."
"Business with terrorists cannot be business as usual," she added.
In a statement, Lafarge's new owner Holcim said none of the conduct involved Holcim, "which has never operated in Syria".
It added that former Lafarge executives involved in the bribery had concealed it from Holcim, as well as external auditors.
Eric Olsen, who ran Lafarge and Holcim until 2017, stepped down from his role following an investigation into Lafarge's activities in Syria.
At the time, Mr Olsen said he had not been involved in any wrongdoing and was standing down to bring "serenity" to the company.
Lafarge also faces charges of complicity in crimes against humanity in France over its activities in Syria, but the company denies the claims