5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one
Summary
This study details the crystal structure of a nitrobenzodiazole compound. The nitro group exhibits slight twisting, and molecules form dimers via hydrogen bonds, creating ribbon-like structures through further interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Benzodiazole derivatives are important scaffolds in medicinal chemistry.
- Understanding the solid-state structure of organic molecules is crucial for predicting their properties and reactivity.
- Nitro-substituted aromatic compounds exhibit diverse electronic and structural characteristics.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(10)H(7)N(3)O(3).
- To investigate the intermolecular interactions and packing motifs in the solid state.
- To analyze the conformational preferences of the nitro substituent relative to the benzodiazole core.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.
- Intermolecular interactions, including hydrogen bonding and C-H⋯O interactions, were identified and characterized.
Main Results:
- Two independent molecules of C(10)H(7)N(3)O(3) were observed in the asymmetric unit.
- The nitro substituent showed slight twisting from the benzodiazole fused-ring system (dihedral angles of 4.9° and 8.5°).
- Molecules formed supramolecular dimers through N-H⋯O hydrogen bonds, resulting in a planar dimer structure (dihedral angle of 2.0°).
- Adjacent dimers were linked by acetyl-ene-nitro C-H⋯O interactions, forming a ribbon motif along the (110) direction.
Conclusions:
- The crystal structure reveals specific conformational preferences and intermolecular interactions.
- Hydrogen bonding and C-H⋯O interactions play a significant role in the self-assembly of the title compound.
- The observed ribbon motif provides insights into the solid-state architecture of nitrobenzodiazole derivatives.
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