2-Meth-oxy-carbonyl-6-nitro-benzoic acid

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure Analysis

Background:

• Understanding the precise spatial arrangement of substituents on aromatic rings is crucial for predicting chemical properties.
• Crystal packing forces significantly influence molecular conformation and intermolecular interactions.
• Detailed structural analysis provides fundamental data for materials science and drug design.

Purpose of the Study:

• To elucidate the three-dimensional molecular structure of the title compound, C(9)H(7)NO(6).
• To quantify the dihedral angles between the benzene ring and its nitro, carboxy, and methoxycarbonyl substituents.
• To characterize the intermolecular interactions and crystal packing in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Dihedral angles were precisely measured from the crystallographic data.
• Hydrogen bonding and other non-covalent interactions were identified and analyzed.

Main Results:

• The dihedral angles of the nitro, carboxy, and methoxycarbonyl groups relative to the benzene ring were determined to be 29.99(8)°, 67.09(8)°, and 32.48(10)°, respectively.
• One classical O-H⋯O hydrogen bond and two nonclassical C-H⋯O contacts were observed.
• These interactions mediate the formation of a robust three-dimensional supramolecular network in the crystal.

Conclusions:

• The study provides precise geometric parameters for the title compound, revealing significant deviations from planarity due to substituent interactions.
• The identified intermolecular interactions dictate the crystal packing, leading to a stable 3D architecture.
• This detailed structural information serves as a foundation for further investigations into the compound's physical and chemical properties.