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N-(2,6-Dimethyl-phen-yl)maleamic acid
Summary
This study details the crystal structure of C(12)H(13)NO(3), revealing two independent molecules. Molecular conformation is stabilized by intramolecular hydrogen bonds, with intermolecular interactions forming crystal networks.
Area of Science:
- Crystallography
- Molecular Chemistry
- Organic Chemistry
Background:
- Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
- Amide functional groups play a significant role in molecular interactions and crystal packing.
- Hydrogen bonding and dipolar interactions are key non-covalent forces dictating crystal architecture.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(12)H(13)NO(3).
- To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
- To investigate the role of hydrogen bonding and carbonyl-carbonyl interactions in stabilizing the crystal structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts was performed.
- Hydrogen bonding and dipolar interactions were identified and characterized.
Main Results:
- The asymmetric unit contains two independent molecules of C(12)H(13)NO(3).
- Each molecule exhibits an anti conformation of the N-H and C=O bonds in the amide segment.
- Intramolecular O-H⋯O hydrogen bonds stabilize individual molecular conformations.
- Intermolecular N-H⋯O hydrogen bonds link molecules into a crystal network.
- A significant carbonyl-carbonyl dipolar interaction with an O⋯C contact of 2.926(3) Å was observed.
Conclusions:
- The crystal structure of C(12)H(13)NO(3) is characterized by specific molecular conformations and extensive intermolecular interactions.
- Intramolecular hydrogen bonding plays a key role in stabilizing the molecular conformation.
- Intermolecular hydrogen bonding and carbonyl-carbonyl dipolar interactions dictate the overall crystal packing.
- The findings provide insights into the structure-property relationships of this organic compound.
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