7-Methoxy-1-{[(Z)-3-nitrophenylimino](phenyl)methyl}-2-naphthol
Atsushi Nagasawa1, Akiko Okamoto, Noriyuki Yonezawa
1Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan.
This study details the crystal structure of a novel organic compound, C(24)H(18)N(2)O(4). The molecule exhibits a unique spatial arrangement of its aromatic rings and forms dimers through intermolecular hydrogen bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
- Aromatic ring orientation and intermolecular interactions dictate crystal packing and solid-state behavior.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(24)H(18)N(2)O(4).
- To analyze the spatial arrangement of aromatic rings and the nature of hydrogen bonding within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of dihedral angles and bond configurations provided insights into molecular geometry.
- Identification and analysis of intermolecular interactions, including hydrogen bonds and C-H⋯O interactions.
Main Results:
- The title compound, C(24)H(18)N(2)O(4), was structurally characterized.
- Phenyl and benzene rings are oriented nearly perpendicular to the naphthalene system (dihedral angles of ~71° and ~85°).
- A Z configuration around the C=N bond was observed, and molecules form centrosymmetric dimers via O-H⋯O hydrogen bonds between hydroxyl and nitro groups.
Conclusions:
- The crystal structure reveals a non-planar molecular conformation with significant twists between aromatic systems.
- Intermolecular hydrogen bonding plays a key role in organizing molecules into dimers within the crystal.
- The study provides fundamental structural insights into this class of organic compounds.
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