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With the Obama administration about to decide whether to green-light a controversial pipeline to take crude oil from Canada’s oil sands to the United States Gulf Coast, e-mails released Monday paint a picture of a sometimes warm and collaborative relationship between lobbyists for the company building the billion-dollar pipeline and officials in the State Department, the agency that has final say over the pipeline.

Environmental groups said the e-mails were disturbing and evidence of “complicity” between TransCanada, the pipeline company, and American officials tasked with evaluating the pipeline’s environmental impact.

The e-mails, the second batch to be released in response to a Freedom of Information Act request filed by the environmental group Friends of the Earth, show a senior State Department official at the United States Embassy in Ottawa procuring invitations to Fourth of July parties for TransCanada officials, sharing information with the company about Secretary of State Hillary Rodham Clinton’s meetings and cheering on TransCanada in its quest to gain approval of the giant pipeline, which could carry 700,000 barrels a day.

“You see officials who see it as their business not to be an oversight agency but as a facilitator of TransCanada’s plans,” said Damon Moglen, the director of climate and energy project for Friends of the Earth. While the e-mails refer to multiple meetings between TransCanada officials and assistant secretaries of state, he said, such access was denied to environmental groups seeking input. Environmental groups argue that the pipeline, known as the Keystone XL project, would result in unacceptably high emissions and disrupt pristine ecosystems.

Before he was TransCanada’s chief Washington, D.C., lobbyist, Paul Elliott was a top official in Mrs. Clinton’s failed 2008 presidential campaign.

Many of the new e-mails are between Mr. Elliott and Marja Verloop, the counselor for energy and environment at the embassy in Ottawa. On Sept. 10, 2010, in response to an e-mail from Mr. Elliot announcing that Senator Max Baucus was supporting the pipeline, Ms. Verloop wrote: “Go Paul!” In an e-mail to David Jacobson, United States ambassador to Canada, she described TransCanada as “comfortable and on board” with some developments in the review process.

Wendy Nassmacher, a State Department spokeswoman, disputed that the e-mails showed a pro-pipeline bias. “We are committed to a fair, transparent and thorough process,” she said in an e-mail Sunday. “Throughout the process we have been in communication with industry as well as environmental groups, both in the United States and in Canada.” She noted that the State Department had conducted hearings in communities along the route of the proposed pipeline last week.

The New York Times, “TransCanada Pipeline Foes Allege Bias In U.S. Emails.”