Title of article :
Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hydroxymethyl-2-trichloromethyl-1,3-dioxolan-4-yl]-2-methylprop-2-enoate
Author/Authors :
Oishi, Takeshi School of Medicine, Keio University, Japan , Yasushima, Daichi Department of Applied Chemistry - Faculty of Science and Technology - Keio University, Japan , Yuasa, Kihiro Department of Applied Chemistry - Faculty of Science and Technology - Keio University, Japan , Chida , Noritaka Department of Applied Chemistry - Faculty of Science and Technology - Keio University, Japan
Abstract :
In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hydroxymethyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intramolecular hydrogen bonds (O—H⋯N and N—H⋯O) between the hydroxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methylprop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, molecules are connected into a dimer by an O—H⋯O hydrogen bond. The dimers are further linked by N—H⋯O, C—H⋯N and C—H⋯O interactions, extending a sheet structure parallel to (-101).
Keywords :
disorder , crystal structure , amino group , hydroxy group , hydrogen bonding , dioxolane , orthoamide ding
Journal title :
Acta Crystallographica Section E: Crystallographic Communications