Chris.
The interaction doesn't look like it was formed correctly. I would suggest using the flexible factorial model with 3 factors:
(1) Session (2 levels for the 2 measurements)
(2) Group (2 levels for the 2 values of the categorical variable)
(3) Subject (66 levels, one for each subject)
Then setup the models with:
Main effects for (1), (2), and (3) and the interaction of (1) and (2).
You can look at my prior posts on flexible factorial models and the contrasts to find instructions on how to generate any contrast. The search term: S1G1C1 should help find the previous posts.
Best,
Donald