have you gains that you want to use the losses against, as remember the person buying the shares will have their cost at lower price, so if sold would be liable to all price increase versus this purchase price.
If you don't intend to sell then this is not an issue, but you don't want to have a greater gain in the hands of the new owner, with no gains for the former owner to use the created loss against.
Not sure how revenue would look at this type of transaction, but depending on the value might not be interested,