Ecclesiasticus/Sirach

c. 180 BC.
This is a bit confusing. First, "Sira" and "Sirach" are both used to name the book. Second, it was not written by Sira but by Sira's grandson (Jesus or Joshua, son of Eleazer, son of Sira (called ben Sira; in Hebrew, "ben" means "son of")).
Third, Jews referred to it as Sirach or Wisdom of Ben Sira. Starting in the 200s, Christians began referring to it as "Ecclesiasticus," which means "church book" in Greek.

Deuterocanonical (means "secondary or less sacred scripture") for Catholic, Eastern Orthodox, Oriental Orthodox, and some Anglican and Lutheran churches.
Apocrypha for most Protestant churches.

Chapters 1-43 read like Proverbs 9-31, mainly individual wisdom sayings ranging from one verse to multiple verses.
Chapters 44 through almost the end of 50 praise many Jewish leaders from the past.
50:25-51: A conclusion explaining the importance of living according to these wisdom writings
51: A prayer and an exaltation of having lived a life of wisdom.

The earliest copy comes from a collection discovered at Masada, predating its Christian use.
2. In 50:25, the book refers to the Samaritans as "not even a people," indicating that the Jewish loathing of the Samaritans existed in the second century BC.
It was translated into Greek roughly 50 years later by the grandson of Jesus/Joshua, son of Eleazer, son of Sira (unknown but called the grandson of ben Sira), who also wrote the Prologue to Sirach (aka Ecclesiasticus) as a preface to Sirach/Ecclesiasticus.