LTSS WHEN MIL C21 WAS DSNDED THROUGH THE ALT OF A CPR DA20 WITH LESS THAN THE REQUIRED 5 MI SEPARATION. OPERROR.

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IT WAS NECESSARY TO DSND ACFT #1 FROM FL350 TO FL310. I ISSUED A DSCNT CLRNC KNOWING THAT I WOULD NEED TO VECTOR AT LEAST 1 OF THE ACFT. I IMMEDIATELY TURNED ACFT #2 15 DEGS L TO GET HIM STARTED IN THE DIRECTION TO GO BEHIND ACFT #1. I BELIEVE THAT ACFT #2 PICKED UP SPD AT THIS POINT. I THEN TURNED ACFT #1 15 DEGS L. EVENTUALLY I TURNED ACFT #1 TO A 190 DEG HDG (APPROX 60-70 DEGS OFF THE ORIGINAL HDG). I TURNED ACFT #2 TO A 90 DEG HDG (APPROX 80 DEGS OFF THE ORIGINAL HDG). THE ACFT PASSED WITH 4 NM SEPARATION AT THE CLOSEST POINT. I BELIEVE THE INCIDENT OCCURRED PRIMARILY DUE TO AN ERROR IN JUDGEMENT. I BELIEVE THAT I SHOULD HAVE WAITED TO DSND ACFT #1 UNTIL HE HAD PASSED OVER ACFT #2; BUT I WAS ALSO COGNIZANT OF THE FACT THAT; IN ORDER TO DO THAT; I WOULD NEED TO COORDINATE WITH THE SUPER HIGH SECTOR TO INFORM THEM THAT I WOULD NOT BE DSNDING THE ACFT IMMEDIATELY. I ALSO NEEDED TO CORRECT THE FILED RTE ON ACFT #1 AND I FELT THAT IN ORDER TO FULFILL ALL OF THE REQUIREMENTS; I NEEDED TO START THE ACFT DOWN AND MAKE THE SIT WORK. UNFORTUNATELY; THE 5 NM SEPARATION WAS NOT MAINTAINED.