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3,5-Dinitro-benzoyl chloride.

Hong-Yong Wang1, Min-Hao Xie, Shi-Neng Luo

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Summary
This summary is machine-generated.

This study details the molecular structure of C(7)H(3)ClN(2)O(5), revealing a disordered carbonyl chloride group and an approximately planar molecule. Crystal packing is influenced by specific hydrogen bonds.

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Area of Science:

  • Crystallography and Molecular Structure
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Understanding the precise arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Disorder in crystal structures can significantly impact molecular conformation and intermolecular interactions.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(7)H(3)ClN(2)O(5).
  • To investigate the nature and extent of disorder in the carbonyl chloride group.
  • To analyze the molecular planarity and substituent orientation.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
  • Disorder modeling was performed to account for the multiple orientations of the carbonyl chloride group.
  • Geometric parameters, including dihedral angles, were precisely calculated.

Main Results:

  • The carbonyl chloride group exhibits significant positional disorder, occupying two distinct orientations with nearly equal probabilities (0.505 and 0.495).
  • The molecule is largely planar, with small dihedral angles between the benzene ring and the carbonyl chloride group (9.6° and 7.1°).
  • A notable twist was observed for the nitro group at the 5-position (dihedral angle of 6.7°).
  • Crystal packing is characterized by stabilizing C-H⋯O hydrogen bonds.

Conclusions:

  • The crystal structure of C(7)H(3)ClN(2)O(5) is characterized by significant carbonyl chloride disorder and a near-planar molecular geometry.
  • The observed disorder and substituent orientation provide insights into the solid-state behavior of this compound.
  • Intermolecular hydrogen bonding plays a key role in stabilizing the crystal lattice.