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Issue 4, 2006
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Isomorphic supramolecular structures via one-dimensional hydrogen bonding motifs in crystals of chiral difluorolactates, trichlorolactates and trifluorolactates

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Abstract

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⋯O[double bond, length as m-dash]C, and C–H⋯O[double bond, length as m-dash]C 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.

Graphical abstract: Isomorphic supramolecular structures via one-dimensional hydrogen bonding motifs in crystals of chiral difluorolactates, trichlorolactates and trifluorolactates

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Publication details

The article was received on 10 Jan 2006, accepted on 06 Mar 2006 and first published on 20 Mar 2006


Article type: Paper
DOI: 10.1039/B600325G
CrystEngComm, 2006,8, 320-326

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    Isomorphic supramolecular structures via one-dimensional hydrogen bonding motifs in crystals of chiral difluorolactates, trichlorolactates and trifluorolactates

    S. Takahashi, T. Jukurogi, T. Katagiri and K. Uneyama, CrystEngComm, 2006, 8, 320
    DOI: 10.1039/B600325G

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