Abstract

In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073 (3) Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564 (7) Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215 (7) Å. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1 (3)° with the benzene ring. An intra-molecular O-H⋯O hydrogen bond supports the mol-ecular conformation, enclosing an S(11) graph-set motif. In the crystal, inter-molecular C-H⋯O hydrogen bonding links the mol-ecules into a tape running along the b axis. Furthermore, other weak C-H⋯O hydrogen bonds and a C-H⋯π inter-action connect the tapes into a sheet structure parallel to (100).

Highlights

  • In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073 (3) A, and one of the N-methyl groups shows rotational disorder

  • The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564 (7) A

  • C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215 (7) A

Read more

Summary

Chemical context

Five-membered cyclic acetal is a pervasive building block in organic synthesis since it is prepared from an aliphatic or an aromatic 1,2-diol. These conversions are often carried out with protection of the contiguous diol (Wuts, 2014) to prevent unexpected side reactions or to reduce the polarity of the substrate, especially for carbohydrates. Masking of the hydroxy groups is a disadvantage in terms of crystallization, due to loss of hydrogen-bond donors, it is expected to stabilize the crystal packing in order to contribute conformational rigidity by forming the cyclic acetal (Vijayasaradhi et al, 2003). The relative configurations were confirmed by the X-ray analysis as C7R, C10S and C14R

Structural commentary
Supramolecular features
Database survey
Synthesis and crystallization
Refinement
Full Text
Published version (Free)

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call