Because you only get to claim the tax loss when the company...

Because you only get to claim the tax loss when the company winds up or if the shares are officially declared to be worthless. But the company is going to be taken over (for $165k). Your shareholding will be consolidated 291 old shares for 1 new share. But the company will still exist, and the shares are not (quite) worthless, so the conditions for a tax loss are not met.