Matrix isolation infrared spectra of a weak C-H center dot center dot center dot O hydrogen-bonded complex between the keto-enol form of 1,2-cyclohexanedione (HCHD) and chloroform have been measured. The spectra reveal that the intramolecular O-H center dot center dot center dot O H-bond of HCHD is weakened as a result of complex formation, manifesting in prominent blue shift (similar to 23 cm(-1)) of the nu(O-H) band and red shifts (similar to 7cm(-1)) of nu(C=O) bands of the acceptor (HCHD). The nu(C-H) band of donor CHCl3 undergoes a large red shift of similar to 33 cm(-1). Very similar spectral effects are also observed for formation of the complex in CCl4 solution at room temperature. Our analysis reveals that out of several possible iso-energetic conformational forms of the complex, the one involving antagonistic interplay between the two hydrogen bonds (intermolecular C-H center dot center dot center dot O and intramolecular O-H center dot center dot center dot O) is preferred. The combined experimental and calculated data presented here suggest that in condensed media, conformational preferences are guided by directional hyperconjugative charge transfer interactions at the C-H center dot center dot center dot O hydrogen bonding site of the complex.