Exchanging stock for no remuneration

[Rossly]

In 2016 I invested in a Private Placement.  I subsequently converted some of the stock to a Roth IRA, paying all the appropriate taxes at $4.50 per share.  The stock has now nearly bellied  up at 33 cents per share and I'm looking for a way to recoup the money I paid in taxes.  There is still a small amount in the Roth account.  If I reassign all of the Roth stock to the issuer as an exchange for no remuneration, can I show a loss.  There will be no forms from the issuer so unclear if or how I would recoup the taxes already paid and report that on 2021 filings. Thanks so much.          

[DanielV01]

Unfortunately not.  The biggest advantage to a Roth account is that all growth in the account is tax-free, as long as you take a qualifying distribution.  But the opposite is also true:  if the Roth loses value, you cannot claim any loss.