1 Enoch 12:4
1 Before these things, Enoch was hidden, and no one among the children of men knew where he was hidden, where he lived, or what had happened to him. 2 His dealings were with the Watchers, and he spent his days among the holy ones. 3 And I, Enoch, was praising the Lord of majesty and the King of the ages, and lo! the Watchers called me - Enoch the scribe - and said to me: 4 'Enoch, you scribe of righteousness, go, tell the Watchers of heaven who have left the high heaven, the holy eternal place, and have defiled themselves with women, and have acted as the children of earth do, and have taken wives for themselves: You have caused great destruction on the earth: 5 And you shall have no peace or forgiveness of sin; and as much as you delight in your children, 6 You will witness the murder of your beloved ones, and you will mourn over the destruction of your children, and you will plead forever, but you will not find mercy or peace.'
Jude 1:6
4 For certain men have secretly slipped in among you—men who long ago were marked out for the condemnation I am about to describe—ungodly men who have turned the grace of our God into a license for evil and who deny our only Master and Lord, Jesus Christ. 5 Now I desire to remind you (even though you have been fully informed of these facts once for all) that Jesus, having saved the people out of the land of Egypt, later destroyed those who did not believe. 6 You also know that the angels who did not keep within their proper domain but abandoned their own place of residence, he has kept in eternal chains in utter darkness, locked up for the judgment of the great Day. 7 So also Sodom and Gomorrah and the neighboring towns, since they indulged in sexual immorality and pursued unnatural desire in a way similar to these angels, are now displayed as an example by suffering the punishment of eternal fire. 8 Yet these men, as a result of their dreams, defile the flesh, reject authority, and insult the glorious ones. 9 But even when Michael the archangel was arguing with the devil and debating with him concerning Moses’ body, he did not dare to bring a slanderous judgment, but said, “May the Lord rebuke you!” 10 But these men do not understand the things they slander, and they are being destroyed by the very things that, like irrational animals, they instinctively comprehend.
Notes and References
"... Jude's second summary involves a description of angels that is found in the Enochic Book of Watchers. In Jude, the angels are sharply described through participial clauses (Clause 7.1 and 7.2), which evince the logico-semantics of elaboration definition and demonstrate that they are those who did not keep their proper domain, but rather abandoned their proper abode. Universally, commentators reason that this refers to the Enochic legend in which it is explained that an errant group of angels (the 'Watchers') engaged in sexual relations with human women (1 Enoch 6-7) and taught humans how to make weapons, wage war, and perform magic (1 Enoch 8). Although at least one scholar notes that the wording of Jude 6 does not seem to communicate that the transgression of the angels was sexual in nature, 1 Enoch 12:4-5 suggests that reading the implication of sexual sin in Jude 6 is implied by the language of Jude 21 ..."
Hunt, Benjamin B. "Know Your Enemies": Rhetorical Semantics in the Epistle of Jude (p. 96) McMaster Divinity College, 2014