Acta Crystallographica Section C

Crystal Structure Communications

Volume 58, Part 11 (November 2002)

Acta Cryst. (2002). C58, o645-o648 [doi:10.1107/S0108270102016086]

Structural motifs in acetoacetanilides: the effect of a fluorine substituent

G. Chisholm, A. R. Kennedy, L. Beaton and E. Brook

Abstract: The structures of three fluoro-substituted acetoacetanilides, namely 2'-, 3'- and 4'-fluoroacetoacetanilide, all C₁₀H₁₀FNO₂, are presented and discussed. We observe a planar structure with intramolecular hydrogen bonding when the F atom is in the ortho position of the aromatic ring, and a twisted structure with intermolecular hydrogen bonding when the F atom is in the meta or para positions. It can be predicted which of these two structural motifs will be adopted by considering the position of any aromatic substituents. In this regard, fluorine appears to mimic the steric effect of a larger substituent, which we attribute to its high electronegativity.

Formula: Three isomers of C₁₀H₁₀FNO₂

Online 11 October 2002


	Structure factor file (CIF format) (100.8 kbytes) Contains datablock II

	Structure factor file (CIF format) (104.1 kbytes) Contains datablock III

	Structure factor file (CIF format) (214.2 kbytes) Contains datablock IV

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