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The crystal structures of three 1,5-anhydropentitols of formulae C 5 H 10 O 4  and their per- O -acetyl derivatives of formulae C 11 H 16 O 7  are reported. 1,5-anhydro- D -arabinitol (ADA), 1,5-anhydroribitol (AR), 1,5-anhydroxylitol (AX), 2,3,4-tri- O -acetyl-1,5-anhydro- D -arabinitol (AcADA), 2,3,4-tri- O -acetyl-1,5-anhydroribitol (AcAR) and 2,3,4-tri- O -acetyl-1,5-anhydroxylitol (AcAX) have the following space group and unit cell parameters: ADA, orthorhombic,  P 2 1 2 1 2 1 ,  a  = 6.521(1) Å,  b  = 6.826(1) Å,  c  = 13.557(3) Å; AR, monoclinic,  P 2 1 / n ,  a  = 6.515(1) Å,  b  = 12.003(1) Å,  c  = 8.272(1) Å,  β  = 105.65(1)°; AX, monoclinic,  P 2 1 / n ,  a  = 6.652(2) Å,  b  = 9.224(2) Å,  c  = 10.548(2) Å,  β  = 101.80(1)°; AcADA, orthorhombic,  P 2 1 2 1 2 1 ,  a  = 8.182(2) Å, = 10.768(2) Å,  c  = 15.111(3) Å; AcAR, monoclinic,  P 2 1 / c ,  a  = 15.178(1) Å,  b  = 10.339(1) Å,  c  = 8.038(1) Å,  β  = 92.50(1)°; and AcAX, monoclinic,  P 2 1 / c ,  a  = 12.092(1) Å,  b  = 9.066(1) Å,  c  = 12.492(2) Å,  β  = 102.39(1)°. The structures were solved using direct methods and refined by full-matrix least-squares techniques to  R  indices of 0.033, 0.042, 0.045, 0.066, 0.055 and 0.048, respectively. The pyranoid ring adopts  4 C 1  chair confirmation in the molecules of AR, AX and AcAX, and the  1 C 4  one in the molecules of ADA, AcADA and AcAR. Theoretical methods were used to examine lattice energetics and molecular packing in the crystals formed.

Crystal structure and molecular packing analysis of 1,5-anhydropentitols and per- O -acetyl derivatives