Three of the flights had actually taken off within 10 to 15 minutes of their planned departure times.
( ( Three ( of ( the flights ) ) ) ( ( ( had actually ) ( ( taken off ) ( within ( ( ( ( 10 to ) 15 ) minutes ) ( of ( their ( planned ( departure times ) ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (NP (CD Three)) (PP (IN of) (NP (DT the) (NNS flights)))) (VP (VBD had) (ADVP (RB actually)) (VP (VBN taken) (PRT (RP off)) (PP (IN within) (NP (NP (QP (CD 10) (TO to) (CD 15)) (NNS minutes)) (PP (IN of) (NP (PRP$ their) (JJ planned) (NN departure) (NNS times))))))) (. .)))
None of the flights had taken off within 10 to 15 minutes of their planned departure times.
( ( None ( of ( the flights ) ) ) ( ( had ( ( taken off ) ( within ( ( ( ( 10 to ) 15 ) minutes ) ( of ( their ( planned ( departure times ) ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (NP (NN None)) (PP (IN of) (NP (DT the) (NNS flights)))) (VP (VBD had) (VP (VBN taken) (PRT (RP off)) (PP (IN within) (NP (NP (QP (CD 10) (TO to) (CD 15)) (NNS minutes)) (PP (IN of) (NP (PRP$ their) (JJ planned) (NN departure) (NNS times))))))) (. .)))