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rac-2,3-Dibromo-propionamide.

Robert Köppen1, Franziska Emmerling, Matthias Koch

  • 1BAM Federal Institute for Materials Research and Testing, Department of Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|February 21, 2013
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a racemic compound, C(3)H(5)Br(2)NO. Researchers observed N-H⋯O hydrogen bonds forming 2D networks and short bromine-bromine contacts within the crystal lattice.

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Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding the intermolecular interactions and crystal packing of chemical compounds is crucial for predicting their physical and chemical properties.
  • Racemic compounds present unique challenges and opportunities in crystal engineering due to the presence of both enantiomers.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(3)H(5)Br(2)NO.
  • To investigate the intermolecular interactions, including hydrogen bonding and other non-covalent forces, that govern the compound's solid-state arrangement.
  • To characterize the resulting network topology within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
  • Crystallization from methanol was performed to obtain suitable single crystals for analysis.
  • Structural analysis involved identifying hydrogen bond donors and acceptors and quantifying contact distances.

Main Results:

  • The racemic title compound, C(3)H(5)Br(2)NO, was successfully crystallized from methanol.
  • Adjacent molecules form chains along the c-axis via N-H⋯O hydrogen bonds.
  • These chains further assemble into an undulating two-dimensional network parallel to the bc plane through additional N-H⋯O hydrogen bonds.
  • Short bromine-bromine (Br⋯Br) contacts of 3.514(3) Å were identified.

Conclusions:

  • The crystal structure is dominated by a network of N-H⋯O hydrogen bonds, leading to a layered architecture.
  • The presence of Br⋯Br contacts suggests potential for halogen bonding interactions, influencing crystal packing.
  • The findings provide fundamental insights into the solid-state behavior of this specific racemic compound.