Limits...
Crystal structure of 4-nitro ­ phenyl 6- O -ethyl- β - d -galacto ­ pyran ­ oside monohydrate

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The synthesis and crystal structure of the title compound, C14H19NO8·H2O, prepared in three steps from 6-O-ethyl-1,2;3,4-di-O-iso­propyl­idene-α-d-galacto­pyran­ose using protecting-group strategies employed in carbohydrate chemistry, is reported. The asymmetric unit consists of a single galactoside mol­ecule, in which the pyran­oid ring has a 4C1 conformation and the 4-nitro­phenyl moiety is essentially planar. In the crystal, each carbohydrate is surrounded by other d-galactose residues and water mol­ecules, linked by O—H⋯O hydrogen bonds involving all hy­droxy groups, giving a two-dimensional substructure lying parallel to (100) and extended into three dimensions by C—H⋯O inter­actions.

No MeSH data available.


Related in: MedlinePlus

Crystal packing of the title compound, showing the stacked galactoside mol­ecules along the a axis. For clarity, H atoms are not shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC5382630&req=5

fig3: Crystal packing of the title compound, showing the stacked galactoside mol­ecules along the a axis. For clarity, H atoms are not shown.

Mentions: In the crystal, a carbohydrate moiety is connected to eight neighboring d-galactose residues by several direct and water-mediated classical hydrogen bonds (Table 1 ▸), establishing a network of inter­actions (Fig. 2 ▸). Regarding only the O—H⋯O inter­action type, there are O2—H2B⋯O6i, O3—H3B⋯O1Wii and O4—H4B⋯O3iii hydrogen bonds. In addition, there is a single-water bridge connecting O3 to O2 of a nearby galactoside mol­ecule (O1W—H1WA⋯O2iv and O1W—H1WB⋯O3v; for symmetry codes, see Table 1 ▸). A two-dimensional substructure in the form of a sheet lying parallel to (100) is formed. The overall three-dimensional supra­molecular aggregation is completed by inter­molecular C—H⋯O inter­actions: C3—H3A⋯O4vi connects carbohydrate rings stacked along the a axis and C13—H13A⋯O12vii connects ethyl and nitro groups along the c axis. The 4-nitro­phenyl substituent groups are arranged in parallel planes (Fig. 3 ▸), with an inter­planar distance of 3.4355 (14) Å, but the slip angle (48.3°) prevents overlapping and therefore no π–π inter­actions are present [ring-centroid separation = 5.163 (2) Å].


Crystal structure of 4-nitro ­ phenyl 6- O -ethyl- β - d -galacto ­ pyran ­ oside monohydrate
Crystal packing of the title compound, showing the stacked galactoside mol­ecules along the a axis. For clarity, H atoms are not shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382630&req=5

fig3: Crystal packing of the title compound, showing the stacked galactoside mol­ecules along the a axis. For clarity, H atoms are not shown.
Mentions: In the crystal, a carbohydrate moiety is connected to eight neighboring d-galactose residues by several direct and water-mediated classical hydrogen bonds (Table 1 ▸), establishing a network of inter­actions (Fig. 2 ▸). Regarding only the O—H⋯O inter­action type, there are O2—H2B⋯O6i, O3—H3B⋯O1Wii and O4—H4B⋯O3iii hydrogen bonds. In addition, there is a single-water bridge connecting O3 to O2 of a nearby galactoside mol­ecule (O1W—H1WA⋯O2iv and O1W—H1WB⋯O3v; for symmetry codes, see Table 1 ▸). A two-dimensional substructure in the form of a sheet lying parallel to (100) is formed. The overall three-dimensional supra­molecular aggregation is completed by inter­molecular C—H⋯O inter­actions: C3—H3A⋯O4vi connects carbohydrate rings stacked along the a axis and C13—H13A⋯O12vii connects ethyl and nitro groups along the c axis. The 4-nitro­phenyl substituent groups are arranged in parallel planes (Fig. 3 ▸), with an inter­planar distance of 3.4355 (14) Å, but the slip angle (48.3°) prevents overlapping and therefore no π–π inter­actions are present [ring-centroid separation = 5.163 (2) Å].

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The synthesis and crystal structure of the title compound, C14H19NO8·H2O, prepared in three steps from 6-O-ethyl-1,2;3,4-di-O-iso­propyl­idene-α-d-galacto­pyran­ose using protecting-group strategies employed in carbohydrate chemistry, is reported. The asymmetric unit consists of a single galactoside mol­ecule, in which the pyran­oid ring has a 4C1 conformation and the 4-nitro­phenyl moiety is essentially planar. In the crystal, each carbohydrate is surrounded by other d-galactose residues and water mol­ecules, linked by O—H⋯O hydrogen bonds involving all hy­droxy groups, giving a two-dimensional substructure lying parallel to (100) and extended into three dimensions by C—H⋯O inter­actions.

No MeSH data available.


Related in: MedlinePlus