4-Butyl-amino-3-nitro-benzoic acid

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.
• The compound C(11)H(14)N(2)O(4) presents an interesting case for crystallographic analysis due to its functional groups.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(11)H(14)N(2)O(4).
• To analyze the molecular geometry, conformation, and intermolecular interactions within the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of bond lengths, bond angles, and intermolecular contacts was performed.

Main Results:

• The asymmetric unit contains four independent molecules (A, B, C, D) with similar geometries and extended butyl-amino side chains.
• Evidence of pi-pi interactions between stacked benzene rings (centroid-centroid distance ~3.6 Å) was observed.
• Intra-molecular N-H⋯O hydrogen bonds and inter-molecular O-H⋯O, C-H⋯O, and C-H⋯π interactions contribute to crystal packing.
• The crystal was identified as a non-merohedral twin with a minor component refining to 0.290(1).

Conclusions:

• The crystal structure of C(11)H(14)N(2)O(4) is characterized by specific molecular conformations and extensive intermolecular interactions.
• The identified pi-pi stacking and hydrogen bonding networks play a significant role in stabilizing the crystal lattice.