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Updated: May 20, 2026
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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
(Adamantan-1-yl)(phenyl-sulfan-yl)methanone
Summary
This study details the crystal structure of a novel ester, C(17)H(20)OS, revealing two distinct molecular conformations. These adamantyl-containing molecules exhibit unique sulfur atom arrangements influencing their crystal packing and intermolecular interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- The asymmetric unit of the title ester, C(17)H(20)OS, contains two independent molecules (A and B).
- Understanding molecular conformations and crystal packing is crucial for predicting material properties.
Purpose of the Study:
- To elucidate the crystal structure of the title ester, C(17)H(20)OS.
- To analyze the conformational differences between the two independent molecules in the asymmetric unit.
- To investigate the intermolecular interactions governing crystal formation.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of dihedral angles and torsion angles was performed to characterize molecular conformations.
- Identification of C-H⋯π interactions was conducted to understand supramolecular assembly.
Main Results:
- Two independent molecules (A and B) were identified in the asymmetric unit of C(17)H(20)OS.
- Significant differences were observed in the torsion angles around the thio-carboxyl group, specifically the S atom's relationship with the adamantyl methylene carbon.
- Molecule A exhibits an 'anti' relationship, while molecule B shows a 'syn' relationship.
- Supramolecular layers were formed in the crystal lattice through C-H⋯π interactions in the ac plane.
Conclusions:
- The crystal structure of C(17)H(20)OS reveals conformational isomerism within the asymmetric unit.
- The distinct spatial arrangements of the sulfur atom in molecules A and B are key structural features.
- Intermolecular C-H⋯π interactions play a vital role in the formation of layered supramolecular structures.
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