Conformational polymorphism of the molecular complex of 3-fluorobenzoic acid with 4-acetylpyridine

Lynne H. Thomas, Gavin A. Craig, Matthias J. Gutmann, Andrew Parkin, Kenneth Shankland, Chick C. Wilson

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Two polymorphs of the molecular complex formed between 3-fluorobenzoic acid with 4-acetylpyridine are described and found to be based upon the same dimeric supramolecular construct. The conformational freedom around the hydrogen bond results in a 180° rotation about this intermolecular link, distinguishing the polymorphs and affecting the packing of the dimeric units. The two polymorphs are fully characterised by single crystal X-ray and neutron diffraction and quantum mechanical calculations. There is evidence of structured crystal growth defects in both polymorphic crystals via observation of diffuse scattering and a disorder model for the average structure of Form I, which can be interpreted as a mixing of the two dimer conformations. The similarity of energy of the distinct dimeric units, supporting their likely co-existence, has been verified by periodic quantum chemical calculations.
LanguageEnglish
Pages3349-3354
Number of pages6
JournalCrystEngComm
Volume13
Issue number10
Early online date7 Apr 2011
DOIs
Publication statusPublished - 21 May 2011

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polymorphism
Polymorphism
Crystallization
acids
Acids
neutron diffraction
crystal growth
dimers
disorders
Neutron diffraction
hydrogen bonds
Crystal growth
Dimers
Conformations
single crystals
defects
Hydrogen bonds
scattering
diffraction
Single crystals

Keywords

  • molecular complex
  • hydrogen bond
  • intermolecular link
  • polymorphs
  • crystal growth

Cite this

Thomas, Lynne H. ; Craig, Gavin A. ; Gutmann, Matthias J. ; Parkin, Andrew ; Shankland, Kenneth ; Wilson, Chick C. / Conformational polymorphism of the molecular complex of 3-fluorobenzoic acid with 4-acetylpyridine. In: CrystEngComm. 2011 ; Vol. 13, No. 10. pp. 3349-3354.
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Thomas, LH, Craig, GA, Gutmann, MJ, Parkin, A, Shankland, K & Wilson, CC 2011, 'Conformational polymorphism of the molecular complex of 3-fluorobenzoic acid with 4-acetylpyridine' CrystEngComm, vol. 13, no. 10, pp. 3349-3354. https://doi.org/10.1039/C1CE05139C

Conformational polymorphism of the molecular complex of 3-fluorobenzoic acid with 4-acetylpyridine. / Thomas, Lynne H.; Craig, Gavin A.; Gutmann, Matthias J.; Parkin, Andrew; Shankland, Kenneth; Wilson, Chick C.

In: CrystEngComm, Vol. 13, No. 10, 21.05.2011, p. 3349-3354.

Research output: Contribution to journalArticle

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AU - Thomas, Lynne H.

AU - Craig, Gavin A.

AU - Gutmann, Matthias J.

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AU - Shankland, Kenneth

AU - Wilson, Chick C.

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AB - Two polymorphs of the molecular complex formed between 3-fluorobenzoic acid with 4-acetylpyridine are described and found to be based upon the same dimeric supramolecular construct. The conformational freedom around the hydrogen bond results in a 180° rotation about this intermolecular link, distinguishing the polymorphs and affecting the packing of the dimeric units. The two polymorphs are fully characterised by single crystal X-ray and neutron diffraction and quantum mechanical calculations. There is evidence of structured crystal growth defects in both polymorphic crystals via observation of diffuse scattering and a disorder model for the average structure of Form I, which can be interpreted as a mixing of the two dimer conformations. The similarity of energy of the distinct dimeric units, supporting their likely co-existence, has been verified by periodic quantum chemical calculations.

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