Abstract
The X-ray crystal structures of three monosaccharide derivatives prepared by the reaction of sulfanilamide with
d-ribose,
d-arabinose, and
d-mannose have been determined. The derivatives are
N-(
p-sulfamoylphenyl)-α-
d-ribopyranosylamine (
1),
N-(
p-sulfamoylphenyl)-α-
d-arabinopyranosylamine (
2), and
N-(
p-sulfamoylphenyl)-β-
d-mannopyranosylamine monohydrate (
3). The monosaccharide ring of
1 and
2 has the
1
C
4 conformation, stabilized in
1 by an intramolecular hydrogen bond from O-2 to O-4. Compound
3 has the
4
C
1 conformation at the monosaccharide ring and the
gt conformation at the C-6O-6 side chain. Occupancy of the water molecule in the crystal of
3 actually examined was 22%. The degree of interaction between sulfamoyl groups and monosaccharide moieties varies from structure to structure. The packing arrangement of
2 involves hydrogen bonding between sulfamoyl groups and monosaccharide hydroxyl groups, but interactions of this type are fewer in
1, and in
3 the hydrogen bonds are either strictly between monosaccharide hydroxyl groups or strictly between sulfamoyl groups. Pairs of hydrogen bonds (two-point contacts) link neighboring molecules in all three structures, between screw-axially related molecules in
1 and
2 and between translationally related molecules in
3. The contact in
3 defined by the O-3H⋯O-5 and O-6H⋯O-4 hydrogen bonds is found in several other
N-aryl-β-
d-mannopyranosylamine crystal structures and is apparently an especially favorable mode of intermolecular interaction in these compounds.