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Crystal structure and absolute configuration of (4 S ,5 R ,6 S )-4,5,6-trihy ­ droxy-3-methyl ­ cyclo ­ hex-2-enone (gabosine H)

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ABSTRACT

The mol­ecule of the title keto carbasugar, C7H10O4, is formed by a cyclo­hexene skeleton with an envelope conformation, substituted by carbonyl, methyl and hydroxyl groups. The crystal structure is controlled mainly by a combination of strong O—H⋯O and weak C—H⋯O hydrogen bonds, forming nearly perpendicular chains running parallel to the [110] and [-110] directions. This perpendicularity is caused by a tetra­gonal pseudosymmetry influenced by the similarity between the a and b axes, the value of 90.9770 (10)° of the β angle and the action of a 21 screw axis, which transform each chain into its corresponding nearly orthogonal one.

No MeSH data available.


Partial crystal packing of the title compound showing the C—H⋯O and O—H⋯O hydrogen bonds (dotted lines) along [110] and [10], forming sheets parallel to the (001) plane.
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fig2: Partial crystal packing of the title compound showing the C—H⋯O and O—H⋯O hydrogen bonds (dotted lines) along [110] and [10], forming sheets parallel to the (001) plane.

Mentions: In the crystal structure, hydrogen bonds O4—H41⋯O1i [symmetry code: (i) x − 1, y − 1, z] link the mol­ecules into chains that run along the [110] direction (Table 1 ▸). These chains are further connected by weaker C6—H6⋯O4ii and C4—H4⋯O6iii [symmetry codes: (ii) x + 1, y, z; (iii) x, y − 1, z] hydrogen bonds along the [10] direction, forming (001) sheets (Fig. 2 ▸). Considering that the chains run along the diagonal of the ab plane and the fact that a≃b, it is possible to observe that the 21 screw axis parallel to b transforms each chain into a nearly orthogonal one along [10] (Fig. 3 ▸). The orthogonal chains are connected by single C6—H6⋯O6iv, O6—H61⋯O5v and bifurcated O5—H51⋯O4vi and O5—H51⋯O5vi hydrogen bonds [symmetry codes: (iv) −x + 1, y − , −z + 1; (v) −x + 1, y + ; (vi) −x, y + , −z + 1] to define a three-dimensional array along the [001] direction. These hydrogen bonds connect the orthogonal chains by pairs along [001]. Between these neighboring [001] sheets, weak dipolar or van der Waals forces stabilize the assembly along the c-axis direction.


Crystal structure and absolute configuration of (4 S ,5 R ,6 S )-4,5,6-trihy ­ droxy-3-methyl ­ cyclo ­ hex-2-enone (gabosine H)
Partial crystal packing of the title compound showing the C—H⋯O and O—H⋯O hydrogen bonds (dotted lines) along [110] and [10], forming sheets parallel to the (001) plane.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382632&req=5

fig2: Partial crystal packing of the title compound showing the C—H⋯O and O—H⋯O hydrogen bonds (dotted lines) along [110] and [10], forming sheets parallel to the (001) plane.
Mentions: In the crystal structure, hydrogen bonds O4—H41⋯O1i [symmetry code: (i) x − 1, y − 1, z] link the mol­ecules into chains that run along the [110] direction (Table 1 ▸). These chains are further connected by weaker C6—H6⋯O4ii and C4—H4⋯O6iii [symmetry codes: (ii) x + 1, y, z; (iii) x, y − 1, z] hydrogen bonds along the [10] direction, forming (001) sheets (Fig. 2 ▸). Considering that the chains run along the diagonal of the ab plane and the fact that a≃b, it is possible to observe that the 21 screw axis parallel to b transforms each chain into a nearly orthogonal one along [10] (Fig. 3 ▸). The orthogonal chains are connected by single C6—H6⋯O6iv, O6—H61⋯O5v and bifurcated O5—H51⋯O4vi and O5—H51⋯O5vi hydrogen bonds [symmetry codes: (iv) −x + 1, y − , −z + 1; (v) −x + 1, y + ; (vi) −x, y + , −z + 1] to define a three-dimensional array along the [001] direction. These hydrogen bonds connect the orthogonal chains by pairs along [001]. Between these neighboring [001] sheets, weak dipolar or van der Waals forces stabilize the assembly along the c-axis direction.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The mol­ecule of the title keto carbasugar, C7H10O4, is formed by a cyclo­hexene skeleton with an envelope conformation, substituted by carbonyl, methyl and hydroxyl groups. The crystal structure is controlled mainly by a combination of strong O—H⋯O and weak C—H⋯O hydrogen bonds, forming nearly perpendicular chains running parallel to the [110] and [-110] directions. This perpendicularity is caused by a tetra­gonal pseudosymmetry influenced by the similarity between the a and b axes, the value of 90.9770 (10)° of the β angle and the action of a 21 screw axis, which transform each chain into its corresponding nearly orthogonal one.

No MeSH data available.