Crystal structure of 2,5-anhydro-1-O-(p-tolylsulfonyl)-D-mannitol.
2,5-Anhydro-1-O-(p-tolylsulfonyl)-D-mannitol, C13H18SO7, Mr = 318.4, monoclinic, C2, a = 26.370(6), b = 7.9741(11), c = 6.6801(6) A, beta = 91.401(11) degrees, V = 1404.3(6) A3, Z = 4, DX = 1.506 g/cm3, CuK alpha, lambda = 1.54184 A, mu = 23.03 cm-1, F(000) = 672, T = 296(1) K, R = 0.042 for 2832 observations with I > 3 sigma (I) (of 2864 unique data). On the esterified side of the molecule, three bond lengths and three bond angles show small changes compared to the unesterified side, which is similar to the symmetrical parent compound, 2,5-anhydro-D-mannitol. The conformation of the five-membered ring is E5 with P = 49.3 degrees and tau m = 38.1 degrees. The hydroxymethyl groups adopt g+ and g- dispositions similar to the parent molecule. The three hydroxyl groups are involved in a network of intermolecular hydrogen bounds both as donors and acceptors.
Voll
R J
RJ
Department of Biochemistry, Louisiana State University, Baton Rouge 70803.
Nguyen
T M
TM
Fronczek
F R
FR
Younathan
E S
ES
D006860:Hydrogen Bonding; D008353:Mannitol / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D014105:Tosyl Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction
D014105:Tosyl Compounds; D008353:Mannitol; C080711:2,5-anhydro-1-O-(4-tolylsulfonyl)mannitol