How to say he tried to study all night, but in vain. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh徹夜徹夜(tetsuya) (n,vs,adj-no) all night/all-night vigil/sleepless nightで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.勉強勉強(benkyou) (n,vs) study/diligence/discount/reduction(num) 10^24/septillion/quadrillionようとつとめたno dictionary result, likely a conjigated verbが(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/and、(、) Japanese commaだめだめ(dame) (adj-na,n) no good/not serving its purpose/useless/broken/hopeless/wasted/in vain/purposeless/cannot/must not/not allowedだっただった(datta) was。(。) Japanese period "."    
kareha tetsuya de benkyou shiyoutotsutometaga 、 damedatta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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