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Related Experiment Videos

N-(triphenylmethylsulfanyl)phthalimide.

Iván Brito1, Danitza Vargas, Andrea Reyes

  • 1Department of Chemistry, Facultad de Ciencias Basicas, University of Antofagasta, Casilla 170, Antofagasta, Chile. ivanbritob@yahoo.com

Acta Crystallographica. Section C, Crystal Structure Communications
|April 5, 2005
PubMed
Summary

This study reveals that the C27H19NO2S compound forms fused ring structures through hydrogen bonds. These structures assemble into sheets, influenced by the electronic configuration of nitrogen and sulfur atoms.

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Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding the self-assembly of organic molecules is crucial for designing novel materials.
  • Intermolecular interactions, such as hydrogen bonds and pi-stacking, dictate crystal packing and material properties.
  • The role of specific functional groups and electronic structures in directing supramolecular assembly requires detailed investigation.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of the title compound (C27H19NO2S).
  • To investigate the role of hydrogen bonding and pi-contacts in the formation of extended structures.
  • To analyze the influence of nitrogen and sulfur lone-pair orbital orientation on molecular conformation.

Main Methods:

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  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of intermolecular interactions, including C-H...O=C hydrogen bonds and C-H...pi contacts, was performed.
  • Computational methods were utilized to assess the electronic configuration and its impact on conformation.

    • Main Results:

    • The title compound crystallizes with chains of fused rings (R(2)(2)(19)) formed by intermolecular C-H...O=C hydrogen bonds along specific crystallographic directions.
    • These hydrogen-bonded chains are further interconnected by intermolecular C-H...pi contacts, leading to the formation of extended sheet structures.
    • The molecular conformation is significantly influenced by the nearly orthogonal orientation of lone-pair orbitals on the nitrogen (N) and sulfur (S) atoms.

    Conclusions:

    • The study successfully characterized the supramolecular assembly of C27H19NO2S, highlighting the hierarchical formation of chains and sheets.
    • Intermolecular C-H...O=C hydrogen bonds and C-H...pi interactions are key drivers for the observed crystal packing.
    • The electronic properties, specifically the lone-pair orbital arrangement of N and S atoms, play a critical role in dictating the molecule's preferred conformation and subsequent self-assembly.