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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2-Iodo-N-(2-nitro-phenyl-sulfan-yl)aniline
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the crystal structure of a novel organic compound, revealing a unique double helical supramolecular architecture formed by C-H⋯O interactions. The nitro group exhibits slight rotation, and specific intermolecular interactions are notably absent.
Area of Science:
- Crystallography and Supramolecular Chemistry
- Organic Solid-State Chemistry
Background:
- Understanding the relationship between molecular structure and supramolecular assembly is crucial in crystal engineering.
- The specific arrangement of functional groups dictates intermolecular interactions and the resulting solid-state architecture.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(12)H(9)IN(2)O(2)S.
- To investigate the intermolecular interactions responsible for the observed supramolecular architecture.
- To analyze the conformational preferences of the nitro group and the relative orientation of aromatic rings.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular structure.
- Analysis of intermolecular contacts, including hydrogen bonds (C-H⋯O), was performed.
- Dihedral angles were measured to quantify the relative orientation of molecular fragments.
Main Results:
- The crystal structure reveals a slight rotation (8.91°) of the nitro group out of the plane of its bonded aromatic ring.
- A significant dihedral angle (84.0°) exists between the two aromatic rings, defined by the CSN and HNC planes.
- Molecules self-assemble into a double helical supramolecular architecture driven by C-H⋯O interactions; no iodo-nitro, π-π, or C-H⋯π(arene) interactions were observed.
Conclusions:
- The study highlights the role of specific C-H⋯O interactions in directing the formation of a unique double helical supramolecular structure.
- The observed molecular conformation and lack of certain common intermolecular interactions contribute to the distinct crystal packing.
- This detailed structural analysis provides insights into the design principles for novel organic materials with tailored supramolecular architectures.
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