Compare diffrently structured time periods for errors

Change99 

Not sure I understood correctly what is required. If the goal is to convert range as in File1 to one which is in File2

(from most left here to most right one), variant could be using formulas:

in F2

=IFERROR(INDEX(B:B,
   AGGREGATE(15,6,1/
    ($B$2:INDEX($B:$B,COUNTA($B:$B))<>$C$1:INDEX($C:$C,COUNTA($B:$B)-1)) /
    ($B$2:INDEX($B:$B,COUNTA($B:$B)) <> 0)  *
    ROW($B$2:INDEX($B:$B,COUNTA($B:$B))),
    ROW()-ROW($F$1)
  )),
"")

copy and paste this cell to E2.

In G2

=IFERROR(INDEX(C:C,
   AGGREGATE(15,6,1/
    ($C$2:INDEX($C:$C,COUNTA($B:$B))<>$B$3:INDEX($B:$B,COUNTA($B:$B)+1)) /
    ($B$2:INDEX($B:$B,COUNTA($B:$B)) <> 0)   *
    ROW($B$2:INDEX($B:$B,COUNTA($B:$B))),
    ROW()-ROW($F$1)
  )),
"")

Select E2:G2 and drag down till empty cells appear.