No. Angels do not grieve, either for sins or for the pains inflicted on men, because, simply speaking, nothing occurs in the world against the will of the blessed.
Angeli non dolent neque de peccatis, neque de poenis hominum, quia, simpliciter loquendo, nihil fit in mundo contra voluntatem beatorum.
For as the Philosopher says (Ethic. iii, 1) that is called simply voluntary, which a man wills in a particular case, and at a particular time, having considered all the circumstances; although universally speaking, such a thing would not be voluntary: thus the sailor does not will the casting of his cargo into the sea, considered universally and absolutely, but on account of the threatened danger of his life, he wills it. Wherefore this is voluntary rather than involuntary, as stated in the same passage.
Ut enim philosophus dicit in III Ethic. illud dicitur simpliciter voluntarium, quod aliquis vult in particulari, secundum quod agitur, consideratis scilicet omnibus quae circumstant, quamvis in universali consideratum non esset voluntarium, sicut nauta non vult proiectionem mercium in mare, absolute et universaliter considerando, sed imminente periculo salutis hoc vult. Unde magis est hoc voluntarium quam involuntarium, ut ibidem dicitur.
Therefore universally and absolutely speaking the angels do not will sin and the pains inflicted on its account: but they do will the fulfilment of the ordering of Divine justice in this matter, in respect of which some are subjected to pains and are allowed to fall into sin.
Sic igitur Angeli peccata et poenas hominum, universaliter et absolute loquendo, non volunt, volunt tamen quod circa hoc ordo divinae iustitiae servetur, secundum quem quidam poenis subduntur, et peccare permittuntur.