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Structure of a novel, macrocyclic Schiff base.

P K Bharadwaj1, J A Potenza, H J Schugar

  • 1Department of Chemistry, Rutgers, State University of New Jersey, New Brunswick 08903.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 15, 1988
PubMed
Summary

This study details the crystal structure of a novel bicyclic disulfide compound. The molecule features a unique ten-membered ring with two imino groups, revealing distinct torsion angles compared to similar structures.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Structural Chemistry

Background:

  • The synthesis and structural characterization of novel heterocyclic compounds are crucial for understanding chemical diversity.
  • Cyclic disulfides and diamines are important structural motifs in various chemical and biological systems.

Purpose of the Study:

  • To elucidate the three-dimensional molecular structure of (E,E)-1,2,3,4,4a alpha, 12a beta-Hexahydro-7,7,10,-10-tetramethyl-7H,10H-8,9-dithia-5,12-diazabenzo-cyclodec ene.
  • To analyze the structural parameters, including bond lengths, angles, and torsion angles, of the novel bicyclic compound.
  • To compare the observed structural features with those of related acyclic and cyclic compounds.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed on the synthesized compound.

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  • The crystal structure was solved and refined to a final R-factor of 0.031.
  • Lattice parameters and crystallographic data (monoclinic, P2(1)/n) were determined at 296 K.

    • Main Results:

    • The molecular formula was confirmed as C14H24N2S2 with a molecular weight of 284.49 g/mol.
    • The molecule adopts an approximate point symmetry of 2, featuring a chair conformation of the cyclohexane ring fused to a ten-membered ring.
    • Key structural parameters include a C-S-S-C torsion angle of 90.8(1) degrees and an N-C-C-N torsion angle of -63.1(2) degrees.

    Conclusions:

    • The determined crystal structure provides a detailed understanding of the molecular geometry of this novel bicyclic disulfide.
    • The C-S-S-C torsion angle is comparable to acyclic disulfides, while the N-C-C-N torsion angle is notably larger than in related protonated or chelated diamines.
    • This study contributes to the understanding of structural variations in heterocyclic compounds containing disulfide and imine functionalities.