Methyl (E)-2-cyano-3-(6-nitro-1,3-benzodioxol-5-yl)acrylate

Area of Science:

• Crystallography
• Organic Chemistry
• Materials Science

Background:

• The 1,3-benzodioxole moiety is a common structural motif in organic compounds.
• Understanding the solid-state packing and intermolecular interactions is crucial for predicting material properties.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of the title compound, C(12)H(8)N(2)O(6).
• To analyze the planarity of the 1,3-benzodioxole ring and the orientation of the nitro group.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of hydrogen bonding and π-π stacking interactions was performed.

Main Results:

• The 1,3-benzodioxole ring system is essentially planar, with a maximum deviation of 0.036(2) Å.
• The nitro group is oriented at a dihedral angle of 15.4(1)° relative to the ring's mean plane.
• Molecules are organized into C(8) [101] chains through C-H⋯O hydrogen bonds.
• Weak aromatic π-π stacking was observed with a centroid-centroid distance of 3.887(1) Å.

Conclusions:

• The crystal structure of C(12)H(8)N(2)O(6) is characterized by a planar benzodioxole core and specific intermolecular interactions.
• Hydrogen bonding and π-π stacking play significant roles in the self-assembly of molecules in the solid state.
• The findings provide insights into the structure-property relationships of related organic compounds.