Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 9 (September 2008)

organic compounds

gd3225 scheme

Acta Cryst. (2008). C64, o493-o497 [ doi:10.1107/S0108270108022634 ]

A structural systematic study of three isomers of difluoro-N-(4-pyridyl)benzamide

J. McMahon, F. P. Anderson, J. F. Gallagher and A. J. Lough

Abstract: The isomers 2,3-, (I), 2,4-, (II), and 2,5-difluoro-N-(4-pyridyl)benzamide, (III), all with formula C₁₂H₈F₂N₂O, all exhibit intramolecular C-HO=C and N-HF contacts [both with S(6) motifs]. In (I), intermolecular N-HO=C interactions form one-dimensional chains along [010] [NO = 3.0181 (16) Å], with weaker C-HN interactions linking the chains into sheets parallel to the [001] plane, further linked into pairs via C-HF contacts about inversion centres; a three-dimensional herring-bone network forms via C-H [pi] (py) (py is pyridyl) interactions. In (II), weak aromatic C-HN(py) interactions form one-dimensional zigzag chains along [001]; no other interactions with HN/O/F < 2.50 Å are present, apart from long N/C-HO=C and C-HF contacts. In (III), N-HN(py) interactions form one-dimensional zigzag chains [as C(6) chains] along [010] augmented by a myriad of weak C-H [pi] (arene) and O=CO=C interactions and C-HO/N/F contacts. Compound (III) is isomorphous with the parent N-(4-pyridyl)benzamide [Noveron, Lah, Del Sesto, Arif, Miller & Stang (2002). J. Am. Chem. Soc. 124, 6613-6625] and the three 2/3/4-fluoro-N-(4-pyridyl)benzamides [Donnelly, Gallagher & Lough (2008). Acta Cryst. C64, o335-o340]. The study expands our series of fluoro(pyridyl)benzamides and augments our understanding of the competition between strong hydrogen-bond formation and weaker influences on crystal packing.

Formula: Three isomers of C₁₂H₈F₂N₂O


	Structure factor file (CIF format) (112.7 kbytes) [ doi:10.1107/S0108270108022634/gd3225Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (110.5 kbytes) [ doi:10.1107/S0108270108022634/gd3225IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (112.9 kbytes) [ doi:10.1107/S0108270108022634/gd3225IIIsup4.hkl ] Contains datablock III

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