Historical Examples. 1  He had a double chin and a smile which was apologetic but ingratiating. 2  Diana moved nearer to him, with her prettiest and most ingratiating air. 3  He tried to twist his seamed 288 features into an ingratiating grin, but the effort was a failure, producing only a grimace.
not righteous; not upright or virtuous; wicked; sinful; evil: an unrighteous king. 2. not in accordance with right or justice; unfair or unjust: an unrighteous law. Origin of unrighteous.
But English did not pick up this nuance of the word until late 16c. Courteous is thus more commonly said of superiors, civil of inferiors, since it implies or suggests the possibility of incivility or rudeness [OED]. Civil case (as opposed to criminal) is recorded from 1610s. Civil liberty is by 1640s.