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3-(4-Bromo-phen-yl)cyclo-pent-2-en-1-one
Endrit Shurdha1, Kelsey Dees1, Hannah A Miller1
1Department of Chemistry and Chemistry Research Center, 2355 Fairchild Drive, Suite 2N 225, United States Air Force Academy, Colorado Springs, CO 80840, USA.
Summary
This study details the crystal structure of a brominated cyclopentenone compound, revealing a nearly planar ring system with slight bowing between phenyl and cyclopentenone rings. Weak hydrogen bonds influence the crystal packing into parallel sheets.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding molecular geometry and crystal packing is crucial for predicting material properties.
- Cyclopentenone derivatives are important scaffolds in organic synthesis and medicinal chemistry.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound (C11H9BrO).
- To analyze the planarity, ring torsion, and molecular bowing.
- To describe the crystal packing arrangement and identify weak hydrogen bonding.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, torsion angles, and intermolecular contacts.
Main Results:
- The cyclopentenone ring is nearly planar (r.m.s. deviation of 0.0097 Å).
- Small inter-ring torsion angles and a dihedral angle of 5.3(1)° indicate conjugation and slight molecular bowing.
- Crystal packing features parallel sheets with side-to-side stacking, stabilized by weak O⋯H-C(sp2) hydrogen bonds.
Conclusions:
- The compound exhibits a well-defined, nearly planar structure with significant conjugation.
- Crystal packing is governed by specific intermolecular interactions, including weak hydrogen bonds, leading to layered structures.
- The findings provide fundamental insights into the solid-state behavior of this class of organic compounds.