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Related Experiment Videos

2,4,6-Trimethylbenzamide.

Maria Gdaniec1, Teresa Olszewska, Tadeusz Połoński

  • 1Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland. magdan@amu.edu.pl

Acta Crystallographica. Section C, Crystal Structure Communications
|January 9, 2004
PubMed
Summary

The crystal structure of C(10)H(13)NO reveals a 1D network formed by amide molecules linked via hydrogen bonds. This structure is further stabilized by weak pi interactions, creating a unique molecular arrangement.

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Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Organic Solid-State Chemistry

Background:

  • Understanding intermolecular interactions is crucial for designing crystalline materials.
  • Amide groups are versatile functional groups capable of forming various hydrogen bonding networks.
  • Aromatic moieties can participate in non-covalent interactions, influencing crystal packing.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C(10)H(13)NO.
  • To investigate the types and roles of intermolecular interactions in stabilizing the crystal lattice.
  • To characterize the specific hydrogen bonding motifs and pi-interactions present.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding geometry (distances and angles) was conducted.
  • Identification and characterization of weak interactions, such as N-H...pi, were performed.

Main Results:

  • The crystal structure exhibits an infinite one-dimensional network of primary amide molecules.
  • N-H...O[double bond]C hydrogen bonds involving anti NH amide H atoms form a C(4) motif.
  • A weak N-H...pi interaction between the syn-oriented amide H atom and the aromatic ring stabilizes the network, with an H-ring centroid distance of 2.50 Å. The intramolecular dihedral angle between the amide and aryl groups is 84.69°.

Conclusions:

  • The title compound self-assembles into a robust 1D supramolecular chain through a combination of strong hydrogen bonds and weak pi-interactions.
  • The observed crystal packing highlights the importance of considering multiple non-covalent interactions for crystal structure prediction and design.
  • The near-perpendicular arrangement of the amide and aryl groups influences the overall network architecture.

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