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I Peter 3:19 - By which also he went and preached unto the spirits in prison.
II Peter 2:4 - For if God spared not the angels that sinned, but cast them down to hell, and delivered them into chains of darkness, to be reserved unto judgment.
Revelation 9:11 - And they had a king over them, which is the angel of the bottomless pit, whose name in the Hebrew tongue is Abaddon, but in the Greek tongue hath his name Apollyon.; 13 - And the sixth angel sounded, and I heard a voice from the four horns of the golden altar which is before God.

The following examples of ancient writings are to be understood metaphorically.
Genesis 6:1, Deuteronomy 32:8, I Samuel 16:14; 18:10; 19:9, I Kings 22:19, Psalm 82:1, Isaiah 26:14, Enoch 6:1; 7:1; 10:11; 12:4; 15:8, Jubilees 5:1-2, 6, Matthew 25:41, Ephesians 6:12, Hebrews 2:5, Jude 6, I Peter 3:19, II Peter 2:4, Revelation 9:11, 13.

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Jubilees 5:1-2 - And it came to pass when the children of men began to multiply on the face of the earth and daughters were born unto them, that the angels of God saw them on a certain year of this jubilee, that they were beautiful to look upon; and they took themselves wives of all whom they chose, and they bare unto them sons and they were giants. And lawlessness increased on the earth and all flesh corrupted its way, alike men and cattle and beasts and birds and everything that walks on the earth -all of them corrupted their ways and their orders, and they began to devour each other, and lawlessness increased on the earth and every imagination of the thoughts of all men (was) thus evil continually.; 6 - And against the angels whom He had sent upon the earth, He was exceedingly wroth, and He gave commandment to root them out of all their dominion, and He bade us to bind them in the depths of the earth, and behold they are bound in the midst of them, and are (kept) separate.

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Enoch 6:1 https://www.sacred-texts.c... 7:1-And all the others together with them took unto themselves wives, and each chose for himself one, and they began to go in unto them and to defile themselves with them, and they taught them charms and enchantments, and the cutting of roots, and made them acquainted with plants. 10:11-And the Lord said unto Michael:'Go, bind Semjâzâ and his associates who have united themselves with women so as to have defiled themselves with them in all their uncleanness. 12:4-'Enoch, thou scribe of righteousness, go, †declare† to the Watchers of the heaven who have left the high heaven, the holy eternal place, and have defiled themselves with women, and have done as the children of earth do, and have taken unto themselves wives:"Ye have wrought great destruction on the earth. 15:8-And now,the giants, who are produced from the spirits and flesh, shall be called evil spirits upon the earth, and on the earth shall be their dwelling.

2/5
Psalm 82:1 - God standeth in the congregation of the mighty; he judgeth among the gods.
Isaiah 26:14 - They are dead, they shall not live; they are deceased, they shall not rise: therefore hast thou visited and destroyed them, and made all their memory to perish.
Matthew 25:41 - Then shall he say also unto them on the left hand, Depart from me, ye cursed, into everlasting fire, prepared for the devil and his angels.
Ephesians 6:12 - For we wrestle not against flesh and blood, but against principalities, against powers, against the rulers of the darkness of this world, against spiritual wickedness in high places.
Hebrews 2:5 - For unto the angels hath he not put in subjection the world to come, whereof we speak.
Jude 6 - And the angels which kept not their first estate, but left their own habitation, he hath reserved in everlasting chains under darkness unto the judgment of the great day.