Pseudepigrapha

1 Enoch 6:2

1 And it came to pass when the children of men had multiplied that in those days were born unto them beautiful and comely daughters. 2 And the angels, the children of the heaven, saw and lusted after them, and said to one another: 'Come, let us choose us wives from among the children of men and beget us children.' 3 And Semjâzâ, who was their leader, said unto them: 'I fear ye will not indeed agree to do this deed, and I alone shall have to pay the penalty of a great sin.' 4 And they all answered him and said: 'Let us all swear an oath, and all bind ourselves by mutual imprecations not to abandon this plan but to do this thing.'

Date: 200-50 B.C.E.
* Dates are based on scholarly estimates
Pseudepigrapha

Jubilees 4:22

21 And he was moreover with the angels of God these six jubilees of years, and they showed him everything which is on earth and in the heavens, the rule of the sun, and he wrote down everything. 22 And he testified to the Watchers, who had sinned with the daughters of men; for these had begun to unite themselves, so as to be defiled, with the daughters of men, and Enoch testified against (them) all. 23 And he was taken from amongst the children of men, and we conducted him into the Garden of Eden in majesty and honour, and behold there he writes down the condemnation and judgment of the world, and all the wickedness of the children of men. 24 And on account of it (God) brought the waters of the flood upon all the land of Eden; for there he was set as a sign and that he should testify against all the children of men, that he should recount all the deeds of the generations until the day of condemnation.

Date: 150-100 B.C.E.
* Dates are based on scholarly estimates