2-[(E)-(2-Morpholinoeth-yl)iminiometh-yl]-4-nitro-1-oxocyclo-hexa-dienide

Area of Science:

• Crystallography
• Molecular structure determination
• Organic chemistry

Background:

• Zwitterions are neutral molecules with distinct positive and negative charges.
• Understanding zwitterionic structures is crucial in various chemical and biological contexts.
• The title compound's specific structure was previously uncharacterized.

Purpose of the Study:

• To elucidate the molecular structure of the title compound, C(13)H(17)N(3)O(4).
• To investigate the zwitterionic nature and hydrogen bonding interactions within the crystal lattice.
• To characterize the conformation of the morpholine ring and intermolecular interactions.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of bond lengths and angles confirmed the proposed zwitterionic form.
• Identification and analysis of intra- and intermolecular hydrogen bonds and weak interactions.

Main Results:

• The molecule exists as an oxocyclohexa-dienide-iminium zwitterion, with proton transfer from the phenol to the imine nitrogen.
• A strong intramolecular N(+)-H⋯O hydrogen bond forms a stable S(6) ring.
• Intermolecular N-H⋯O hydrogen bonds link molecules into centrosymmetric dimers in the crystal structure.
• The morpholine ring adopts a chair conformation.

Conclusions:

• The study provides definitive structural evidence for the zwitterionic nature of the title compound.
• The observed hydrogen bonding network significantly influences the crystal packing and molecular stability.
• This detailed structural characterization contributes to the understanding of zwitterionic compounds in solid-state chemistry.