Define 2 separate tools with the same tool number (or put them under the same pocket)
I'd suggest they have 2 different adjust registers...
Whether you need to do something more depends on your machine...
With Mazak Integrex using Mazatrol tool data (Tnnn.mm; "mm"=00 thru 26; heavy tools 61 thru 86) you don't need to do anything more - the "flipping" is done on the control when you set up the tool.
I think most other machines will require SOMETHING
option 1) If only need 2 positions 180 deg part: See if (tool orientation) "flip tool around holder" can be used to trigger what you need (note tool that needs flipped needs to be defined in its "un flipped" position)
Option 2) Add a UDE "Lathe Tool Orient" or "Flash Tooling" (or whatever you want to call it). Either have a set of options (0/90/180/27) or just allow them to enter an angle value. Use this to trigger output of appropriate M/G/whatever code in the post.
Ken Akerboom Sr CAx Systems Engr, Moog, Inc.
Production: NX10.0.3.5 MP16/TC11.2 I'd rather be e-steamed than e-diseaseled