if I have a tablespace was 5Mb initally, later someone create some "hugh" tables to make the tablespace growing
to 500Mb, then those tables being dropped. I assume those space will be free.
you can reduce the size of a datafile, providing there is NO data in the space you're removing (in the last 495 Mb in your example).
what you should do is :
drop table huge1;
drop table huge2;
...
once it's ok :
alter tablespace [tbs] coalesce;
and then :
alter database datafile 'your datafile' resize 5M;
if this command fails, then you certainly have data in the bad area, you should look for what it is by looking in dba_extents and dba_data_files ...
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