An effort to take Emmis Communications Corp. private could be in jeopardy if a deal with preferred shareholders is not struck soon.

Another shareholders vote is set for 6:30 p.m. Friday at Emmis headquarters on the Circle, following two failed attempts in the past two weeks.

Company officials have said Emmis CEO Jeff Smulyan is continuing to negotiate with preferred shareholders—who've said they would block the deal—even as he considers other avenues to complete his purchase of the company, including one that would not require their consent.

But Mark Foster, chief investment officer at Kirr Marbach & Co. in Columbus, Ind., is not encouraged by the prospects of getting the deal done, unless Smulyan is willing to sweeten his offer. The firm does not own Emmis shares.

“[Smulyan has] already extended the deadline twice,” Foster said. “It usually doesn’t go much beyond that. It sort of feels like it’s time to put that thing to bed.”

Emmis shares were trading at $2.03 each Friday morning, well below Smulyan’s offer of $2.40 per share to common shareholders, indicating there is doubt he can pull off his plan.

“If people felt like this was a done deal, [the stock] would be trading [within] a few percentage points of the offer price,” Foster said.

Last month, eight firms that hold Emmis preferred stock banded together to prevent the sale. Collectively they hold 38 percent of Emmis preferred shares.

That’s enough to prevent Smulyan from winning two-thirds approval from preferred shareholders needed to convert their shares into bonds at 60 cents on the dollar, in exchange for the attractive interest rate of 12 percent.

Smulyan’s proposal also requires approval from the holders of a majority of Emmis shares, a threshold Smulyan likely would be able to meet.

“It seems like the preferred holders are digging in their heels and they want something else,” Foster said. “I can’t believe they would change their minds and go along with the deal unless they were given some financial incentive.”

Smulyan, through his JS Acquisition Inc. and New York private equity firm Alden Global Capital, submitted the offer in April. The bid values the company at about $90 million.

Founded by Smulyan in 1981, Emmis owns 23 radio stations in the United States and publishes regional magazines in seven cities, including Indianapolis Monthly. It also operates radio stations in Slovakia and Bulgaria.

The company’s audience base has been trimmed by competition from satellite radio and iPods at the same time advertisers have funneled more dollars to the increasing number of websites and cable television channels.

Over the past four years, Emmis’ revenue has swooned by 33 percent to $243 million. Its continuing operations have wracked up losses of more than $430 million.

That performance has caused Emmis’ share price to plunge since the last time Smulyan tried to take the company private in May 2006. At that time, Smulyan’s buyout group offered $15.25 per common share, but could not come to terms with the company’s board of directors.