Oracle CEO Larry Ellison failed to preserve e-mails as well as interview materials related to a book called "Softwar" that should have been supplied in connection with a shareholder lawsuit filed in March 2001 against the company, a federal judge ruled on Tuesday.

The plaintiffs allege that Ellison and others made false statements about the company's financial results during fiscal 2001, how the economy was affecting business and Oracle's 11i application suite, according to the decision filed in U.S. District Court-California Northern District.

Oracle produced only 15 e-mails sent or received by Ellison from Ellison's own files, but pulled more than 1,600 Ellison e-mails from the systems of other company workers, according to Judge Susan Illston.

"Having established with certainty that numerous emails were not produced from Ellison's email files ... it is impossible to know whether additional unproduced emails were also deleted or not turned over," she wrote. "This uncertainty about the existence of other emails is precisely the reason all of Ellison's e-mails should have been preserved and produced."

The plaintiffs had also wanted material stemming from interviews Ellison gave between March 2001 and August 2002 to writer Matthew Symonds for the book "Softwar: An Intimate Portrait of Larry Ellison and Oracle."

But the materials never made it to the plaintiffs, because Symonds had disposed of the laptop containing them in late 2006 or January 2007, according to the filing.

Symonds told Oracle's attorney that Ellison had waived his rights to the materials several years ago, but that still meant Ellison could -- and should -- have preserved them at least until sometime in 2003, well after the suit was filed, according to Illston.

Illston ruled that the jury in the case, Nursing Home Pension Fund et al vs. Oracle Corp. et al, will be told they can infer the missing materials "would demonstrate Ellison's knowledge of, among other things, problems with Suite 11i, the effects of the economy on Oracle's business, and problems with defendants' forecasting model."

An Oracle spokeswoman said Wednesday the company would have no comment.