func_breakable_surf is able to be initially shattered by the crowbar as with all other weapons, however, once shattered, the crowbar stops affecting (or registering collisions for) the remaining shards. Bullets, physics props, explosions, and the player all cause the expected interactions with the entity - the crowbar is the only thing I’ve found that does not clear away shards in BM that did in HL2 and the Episodes.
Given the rarity of func_breakable_surf outside of AM and select portions of QE in the official maps, this is probably not a high priority issue, but it’s quite immersion breaking to swing your crowbar and have it phase through the cracked glass instead of doing anything to it.
EDIT: On further testing, grenades, missiles, etc do NOT affect func_breakable_surf once shattered, only their explosions.