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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
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Crystal structure of mandipropamid.

Hyunjin Park1, Jineun Kim1, Gihaeng Kang1

  • 1Department of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea.

Acta Crystallographica. Section E, Crystallographic Communications
|November 24, 2015
PubMed
Summary

This study details the crystal structure of a novel amide fungicide, (RS)-2-(4-chloro-phenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yl-oxy)phenyl]ethyl}-2-(prop-2-yn-yloxy)acetamide. It reveals specific molecular arrangements and intermolecular interactions critical for its chemical properties.

Keywords:
C—H⋯π inter­actionsamide fungicideconformationcrystal structurehydrogen bonding

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Area of Science:

  • Crystallography
  • Materials Science
  • Organic Chemistry

Background:

  • Amide fungicides are crucial in agriculture for crop protection.
  • Understanding the solid-state structure of active pharmaceutical ingredients is vital for formulation and efficacy.
  • The specific compound (RS)-2-(4-chloro-phenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yl-oxy)phenyl]ethyl}-2-(prop-2-yn-yloxy)acetamide represents a new class of potential fungicides.

Purpose of the Study:

  • To elucidate the crystal structure of the title amide fungicide.
  • To analyze the intermolecular interactions governing the compound's solid-state arrangement.
  • To provide a foundation for structure-activity relationship studies in fungicide development.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles.
  • Identification and characterization of intermolecular interactions, including hydrogen bonds and van der Waals forces.

Main Results:

  • The crystal structure of C23H22ClNO4 was successfully determined.
  • A significant dihedral angle of 65.36(6)° was observed between the chloro-benzene and benzene rings.
  • Supramolecular chains formed by N-H⋯O hydrogen bonds along the c axis, further organized into layers by C-H⋯O and C-H⋯π interactions.

Conclusions:

  • The study provides a detailed 3D structural insight into a novel amide fungicide.
  • The identified intermolecular interactions offer a basis for understanding crystal packing and potential polymorphism.
  • This structural information is valuable for the rational design and optimization of new agrochemical agents.