The special counsel investigating Russian interference in the 2016 presidential election has told a judge that a former adviser to the Trump campaign repeatedly lied about his contacts with Russian operatives and “caused damage” to the government’s inquiry.

In a document filed Friday evening, the special counsel, Robert S. Mueller III, said that the former adviser, George Papadopoulos, misled investigators about the “timing, extent and nature” of the meetings. During one of them, Mr. Papadopoulos was told that Russia had damaging information about Hillary Clinton in the form of “thousands of emails.”

The memo said that Mr. Papadopoulos’s attempts to mislead the F.B.I. had a significant effect on the open investigation into whether President Trump or his advisers coordinated with Russia’s attempts to disrupt the 2016 presidential election.

“The defendant lied in order to conceal his contacts with Russians and Russian intermediaries during the campaign,” the memo said. It happened early in the investigation “when key investigative decisions, including who to interview and when, were being made.”