Optically pure difluorolactates and trichlorolactates were prepared and their crystal structures were determined and compared with those of trifluorolactates. One-dimensional hydrogen bonding networks of these compounds involve infinite OH⋯OH, OH⋯OC, and C–H⋯OC hydrogen bonds. The crystal structure of a single-headed difluorolactate showed a weak intermolecular C–H⋯F hydrogen bond between difluoromethyl (CF2H) groups, leading to a one-dimensional C–H⋯F chain as a hydrogen bonding motif of the CF2H group. In the case of trichlorolactates, the steric effect of the trichloromethyl group on the hydrogen bonding system was revealed. Two-dimensional hydrogen bonding networks by double-headed trifluorolactates, difluorolactate and trichlorolactate provided isomorphic layered crystal structures.
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Takahashi et al. (2006) studied this question.
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