Perillartine.

Area of Science:

• Organic Chemistry
• Crystallography
• Molecular Structure

Background:

• The chiral compound 4-(1-methyl-vinyl)cyclo-hexene-1-carbaldehyde oxime is of interest for its unique structural features.
• Understanding the solid-state arrangement of chiral molecules is crucial for predicting their properties and reactivity.

Purpose of the Study:

• To elucidate the crystal structure of 4-(1-methyl-vinyl)cyclo-hexene-1-carbaldehyde oxime.
• To analyze the molecular conformation and intermolecular interactions in the crystalline state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
• Identification of hydrogen bonding patterns revealed intermolecular interactions.

Main Results:

• The asymmetric unit contains two independent molecules of the title compound.
• One molecule exhibits disorder in its propenyl substituent, with a 50:50 ratio over two sites.
• Both molecules display an approximate envelope conformation for the six-membered ring, with the substituted carbon as the flap.
• The propenyl substituent plane is nearly perpendicular to the ring plane (dihedral angles of 84.6° and 87.4°).
• Two independent molecules form a dimer through O-H⋯N hydrogen bonds across a pseudo-inversion center.
• The unit cell is similar to the known racemate, differing in space group (P).

Conclusions:

• The crystal structure of 4-(1-methyl-vinyl)cyclo-hexene-1-carbaldehyde oxime has been determined.
• The study highlights conformational preferences and the role of hydrogen bonding in stabilizing the crystal lattice.
• The findings contribute to the understanding of stereochemistry and crystal engineering of oxime compounds.