1-(3-Chloro-phen-yl)-3-(4-nitro-phen-yl)urea
Summary
This study details the crystal structure of a novel urea derivative, highlighting its planar benzene rings and specific intermolecular hydrogen bonding that forms a chain structure. The findings offer insights into molecular assembly and crystal engineering.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
- Urea derivatives are versatile building blocks in supramolecular chemistry and materials science.
- The synthesis and characterization of novel organic molecules contribute to the expansion of chemical databases.
Purpose of the Study:
- To elucidate the crystal structure of a newly synthesized urea derivative.
- To investigate the intermolecular interactions governing the solid-state assembly of the compound.
- To analyze the conformational preferences and bonding characteristics of the molecule in the crystalline state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
- The synthesis involved the reaction of 1-chloro-3-isocyanato-benzene with 4-nitro-benzenamine.
- Structural analysis included the identification of hydrogen bonds and other non-covalent interactions.
Main Results:
- The title compound, C(13)H(10)ClN(3)O(3), exhibits a crystal structure with two nearly coplanar benzene rings (inter-ring dihedral angle of 8.70°).
- Molecules form cyclic intermolecular associations via two urea-nitro N-H⋯O hydrogen bonds, leading to a chain structure.
- Weak intermolecular C-H⋯Cl interactions and intramolecular C-H⋯O associations were also observed.
Conclusions:
- The crystal packing is dominated by robust urea-nitro hydrogen bonding, dictating the formation of extended chain architectures.
- The observed planarity of the aromatic systems and specific intermolecular interactions provide a basis for understanding structure-property relationships.
- This study contributes to the understanding of crystal engineering principles for designing functional organic materials.
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