5-Hydr-oxy-8-nitro-1,4-naphthoquinone
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the crystal structure of a nitro compound, C(10)H(5)NO(5). Key findings include intra-molecular hydrogen bonding and significant pi-pi interactions influencing crystal packing.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding molecular interactions and crystal packing is crucial in materials science and drug design.
- Nitroaromatic compounds exhibit diverse properties influenced by their electronic and structural features.
- Intra-molecular hydrogen bonding can significantly affect molecular conformation and reactivity.
Purpose of the Study:
- To elucidate the detailed crystal structure of the title compound, C(10)H(5)NO(5).
- To investigate the nature and significance of intra- and inter-molecular interactions within the crystal lattice.
- To analyze the factors contributing to the overall crystal packing and stability.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
- Intermolecular interactions, including hydrogen bonding and pi-pi stacking, were identified and quantified.
Main Results:
- The compound exhibits an intra-molecular O-H⋯O hydrogen bond forming a six-membered ring (S(6) motif).
- A significant dihedral angle (71.66°) was observed between the nitro group and the benzene ring.
- Short inter-molecular distances between ring centroids (3.7188–3.8299 Å) suggest prominent π-π interactions.
- Short inter-molecular O⋯O and O⋯N contacts were identified as notable features.
- Crystal packing is further stabilized by C-H⋯O (three instances) and C-H⋯π interactions.
Conclusions:
- The crystal structure of C(10)H(5)NO(5) is characterized by a combination of intra-molecular hydrogen bonding and significant inter-molecular interactions.
- π-π interactions and various hydrogen bonds play a critical role in stabilizing the crystal lattice.
- The observed structural features provide valuable data for understanding the solid-state behavior of nitroaromatic compounds.
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