The studies of crystal structures with hydrogen bonds have been actively pursued because of their moderate stabilization energy for constructing unique structures. In this study, we synthesized a molecular conductor based on 2,6-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene (trans-TTF-py2). Two pyridyl groups were introduced into the TTF skeleton toward the structural exploration in TTF-based molecular conductors involved by hydrogen bonds. In the obtained molecular conductor, (trans-TTF-py2)1.5(PF6)·EtOH, short contacts between the pyridyl group and the hydrogen atom of the TTF skeleton were observed, indicating that hydrogen bonding interactions were introduced in the crystal structure. Spectroscopic measurements and conductivity measurement revealed semiconducting behavior derived from π-stacked trans-TTF-py2 radical in the crystal structure. Finally, these results are discussed with the quantified hydrogen bonding stabilization energy, and the band calculation of the crystal obtained from density functional theory calculation.