CTLR CLBS F14 THROUGH ALT OF ACR RESULTING IN LTSS.

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ACR DC9 AND MIL F14. ACR LEVEL FL270 NBOUND. F14 WBOUND AT FL260. I HAD RECEIVED A POINTOUT ON ACR 80 MI PRIOR TO LOSS OF SEPARATION AT THAT TIME THE ACR WAS LEVEL FL330. HE WAS LATER DSNDED TO FL270. MIL WAS LEVEL FL260 REQUESTING FL280. I ISSUED ROUTING CHANGE TO THE MIL TO EXPEDITE HIS FLT. THE ROUTING CHANGED HIS HDG ABOUT 15 DEGS OF PREVIOUS HDG. MIL WAS THEN CLBED TO FL280. I DID NOT REALIZE THE ACR WAS AT THE POS AND ALT HE WAS. WHEN THE CONFLICT ALERT WENT OFF THE MIL WAS OUT OF FL264 AND CLBING. I ELECTED TO TURN TO A HDG OF 330 DEGS SINCE THIS WOULD EXPEDITE THE XING SITUATION AND EXPEDITE THE F14'S CLB. THE ENTAP INDICATED THE F14 WAS CLBING AT APPROX 2000 FPM PRIOR TO THE TURN AND CLRNC TO EXPEDITE CLB. AFTER THE CLRNC THE F14'S CLB RATE GOES TO 500 FPM. I DO NOT UNDERSTAND WHY. HOWEVER WE GUESSED FROM THE ENTAP THAT EVEN AT 2000 FPM WE WOULD HAVE HAD GREATER SEPARATION; BUT STILL BELOW MINIMUMS. HAD I BEEN WORKING THE ACR I WOULD HAVE BEEN MORE AWARE AND THE INCIDENT PROBABLY WOULD NOT HAVE HAPPENED.