1-(Benzotriazol-1-yl)-2-bromoethanone

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Benzotriazole derivatives are important in various chemical applications.
• Understanding the solid-state structure of organic compounds is crucial for predicting their properties.
• Bromo-acetyl groups introduce specific reactivity and structural characteristics.

Purpose of the Study:

• To elucidate the crystal structure of the title compound C(8)H(6)BrN(3)O.
• To analyze the molecular geometry, including planarity and dihedral angles.
• To investigate intermolecular interactions, such as hydrogen bonding, in the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of bond lengths, bond angles, and dihedral angles.
• Identification and analysis of intermolecular hydrogen bonding interactions (C-H⋯O).

Main Results:

• The benzotriazole ring was found to be essentially planar (r.m.s. deviation = 0.0034 Å).
• The bromo-acetyl unit exhibited a dihedral angle of 15.24(16)° relative to the benzotriazole ring.
• Inversion dimers formed via C-H⋯O hydrogen bonds, creating R(2)(2)(12) rings, which further assembled into chains along the b-axis.

Conclusions:

• The crystal structure of C(8)H(6)BrN(3)O is characterized by a planar benzotriazole core and a twisted bromo-acetyl moiety.
• Intermolecular C-H⋯O hydrogen bonding plays a significant role in organizing the molecules within the crystal lattice.
• The observed hydrogen bonding network leads to the formation of extended chains, influencing the overall crystal packing.