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1,4-Dibromo-naphthalene-2,3-diol.

Qinghe Gao1, Yanping Zhu

  • 1Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|November 18, 2011
PubMed
Summary

This study details the crystal structure of C(10)H(6)Br(2)O(2), revealing intramolecular hydrogen bonds forming an S(6) ring. Intermolecular interactions include hydrogen bonds forming chains and weak O-H⋯π interactions, alongside short bromine-bromine contacts.

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Area of Science:

  • Crystal engineering and supramolecular chemistry.
  • Organic solid-state chemistry.
  • Hydrogen bonding and intermolecular interactions.

Background:

  • Understanding intermolecular forces is crucial for designing crystalline materials with specific properties.
  • Hydrogen bonds and halogen bonds play significant roles in crystal packing and network formation.
  • The study of halogenated organic compounds provides insights into structure-property relationships.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(10)H(6)Br(2)O(2).
  • To investigate the types and significance of intermolecular interactions present in the crystal lattice.
  • To analyze the role of hydrogen bonding and short halogen contacts in stabilizing the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular and crystal structure.
  • Analysis of hydrogen bonding networks, including intramolecular and intermolecular O-H⋯O interactions.
  • Identification and quantification of other non-covalent interactions, such as O-H⋯π and Br⋯Br contacts.

Main Results:

  • The crystal structure of C(10)H(6)Br(2)O(2) was successfully determined with a low r.m.s. deviation for non-hydrogen atoms (0.020 Å).
  • An intramolecular O-H⋯O hydrogen bond was observed, forming a six-membered S(6) ring.
  • Intermolecular O-H⋯O hydrogen bonds link molecules into a C(2) chain along the [100] direction, while weak O-H⋯π interactions and short Br⋯Br contacts (3.5972(9) Å) are also present.

Conclusions:

  • The crystal structure is stabilized by a combination of strong intramolecular hydrogen bonds and weaker intermolecular interactions.
  • The observed hydrogen bonding patterns dictate the formation of specific supramolecular architectures (S(6) ring and C(2) chain).
  • The presence of short Br⋯Br contacts suggests potential halogen bonding contributions to crystal stability and packing.