A man in a gray sweatshirt is bending his leg over his head.
A man has his leg over his head.
A man in bending his leg over his head, therefore, the placement of the leg is over the head and the second sentence is entailed.
exists e1 s1 x1 x2 x3 x4.(over(e1,x4) & n_head(x4) & of(x4,x1) & n_male(x1) & n_male(x1) & Theme(e1,x3) & Actor(e1,x1) & v_bend(e1) & n_leg(x3) & of(x3,x1) & in(x1,x2) & n_sweatshirt(x2) & a_gray(s1) & Theme(s1,x2) & n_man(x1))
exists e1 x1 x2 x3.(Theme(e1,x2) & Actor(e1,x1) & v_have(e1) & over(x2,x3) & n_head(x3) & of(x3,x1) & n_male(x1) & n_male(x1) & n_leg(x2) & of(x2,x1) & n_man(x1))