Atsab (H6088) carries a double meaning: to hurt, pain, or grieve — and in other forms, to fashion or shape. The connection between forming and wounding is subtle: to be deeply shaped by something often involves pain. The noun etsev (toil, pain) flows from this root.
God was 'grieved' (vayitatssev) to His heart over human wickedness before the Flood (Genesis 6:6). This is one of Scripture's most stunning anthropomorphisms: the infinite God experiencing anguish over His creation's rebellion. Isaiah 63:10 says Israel 'grieved His Holy Spirit.' Paul echoes this with 'Do not grieve the Holy Spirit' (Ephesians 4:30), making the pain of divine sorrow a New Covenant reality.