We report the design, synthesis, and crystal structure of a conjugated aryleneethynyl molecule, 2‐(2‐{4,5‐dimethoxy‐2‐2‐(2,3,4‐trifluorophenyl)ethynylphenyl}ethynyl)‐6‐2‐(pyridin‐2‐yl)ethynylpyridine, C30H17F3N2O2, that adopts a planar rhombus conformation in the solid state. The molecule crystallizes in the space group P, with Z = 2, and features two intramolecular sp2‐C—H…N hydrogen bonds that co‐operatively hold the arylethynyl molecule in a rhombus conformation. The H atoms are activated towards hydrogen bonding since they are situated on a trifluorophenyl ring and the H…N distances are 2.470 (16) and 2.646 (16) Å, with C—H…N angles of 161.7 (2) and 164.7 (2)°, respectively. Molecular electrostatic potential calculations support the formation of C—H…N hydrogen bonds to the trifluorophenyl moiety. Hirshfeld surface analysis identifies a self‐complementary C—H…O dimeric interaction between adjacent 1,2‐dimethoxybenzene segments that is shown to be common in structures containing that moiety. Co‐operative nonconventional sp2‐C—H…N hydrogen bonds control the conformation of a dipyridyl molecule to a rhombus shape.