In all versions of OGP measurement software, the Align X and Align Y checkboxes under Construct -> Datum Axis Align will align a selected feature to an axis, but only to the
positive side of the axis. In other words, if you have a datum origin established on the
right hand side of your part, and you measure a feature to the
left (negative X-axis side) of your part, and you click
Construct ->
Datum ->
Axis, and click the checkbox for "Align X Axis", it will align the POSITIVE side of the X axis to that feature, and flip everything 180 deg around so that it is upside down from when you started.

If you want to align the X axis to a feature to the left of your origin, then
DO NOT check "Align X Axis". Instead, type in 180 under "Align Angle". Since the negative X axis is 180 deg from 0, this will do the job.
Same thing applies for Y. If you wish to align a feature to the negative side of the Y axis, then you would type in "-90" or "270" under "Align Angle".
To understand this, it is helpful to better understand how the Align Angle option works for Datum Alignments. Angles start at the positive X axis (0 deg) and positive angles go counter-clockwise.
| +X | = 0 degress |
| +Y | = 90 degress |
| -X | = 180 degress |
| -Y | = 270 (-90) degress |