Synthesis and structure of <i>N</i> -(perfluorophenyl)isonicotinamide

The title compound [systematic name: <i>N</i>-(2,3,4,5,6-penta-fluoro-phen-yl)pyridine-4-carboxamide], C<sub>12</sub>H<sub>5</sub>F<sub>5</sub>N<sub>2</sub>O, crystallizes with two independent mol-ecules (<i>A</i> and <i>B</i>) in the asymmetric unit in space group <i>P</i>1. The mol-ecules adopt a conformation where the planes of the penta-fluoro-phenyl and pyridyl rings have twist angles of 5.3 (1) and 14.5 (1)°. In the crystal, the mol-ecules are connected by N-H⋯N hydrogen bonds between the amide H atom and the pyridyl nitro-gen atom of an adjacent mol-ecule to generate [110] chains of alternating <i>A</i> and <i>B</i> mol-ecules. The packing is consolidated by C-H⋯π inter-actions, π-π stacking and C-H⋯O inter-actions and a short F⋯F contact of 2.7270 (13) Å occurs. The structures of related isonicotinamides are surveyed.

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Publication Details

Journal
Acta Crystallographica Section E Crystallographic Communications
Published
2025-12-02
DOI
https://doi.org/10.1107/s2056989025010679
Primary Topic
Crystal structures of chemical compounds
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis and structure of N -(perfluorophenyl)isonicotinamide

Garry S. Hanan, Mihaela Cibian, Arindam Saha
Acta Crystallographica Section E Crystallographic Communications
Crystal structures of chemical compounds
article

Synthesis and structure of N -(perfluorophenyl)isonicotinamide

Garry S. Hanan, Mihaela Cibian, Arindam Saha
article en

Abstract

The title compound [systematic name: <i>N</i>-(2,3,4,5,6-penta-fluoro-phen-yl)pyridine-4-carboxamide], C<sub>12</sub>H<sub>5</sub>F<sub>5</sub>N<sub>2</sub>O, crystallizes with two independent mol-ecules (<i>A</i> and <i>B</i>) in the asymmetric unit in space group <i>P</i>1. The mol-ecules adopt a conformation where the planes of the penta-fluoro-phenyl and pyridyl rings have twist angles of 5.3 (1) and 14.5 (1)°. In the crystal, the mol-ecules are connected by N-H⋯N hydrogen bonds between the amide H atom and the pyridyl nitro-gen atom of an adjacent mol-ecule to generate [110] chains of alternating <i>A</i> and <i>B</i> mol-ecules. The packing is consolidated by C-H⋯π inter-actions, π-π stacking and C-H⋯O inter-actions and a short F⋯F contact of 2.7270 (13) Å occurs. The structures of related isonicotinamides are surveyed.

Acta Crystallographica Section E Crystallographic CommunicationsVol. 82(1)
Université du Québec à Montréal (CA), Université du Québec à Trois-Rivières (CA)
Centre in Green Chemistry and Catalysis, Centre québécois sur les matériaux fonctionnels, Natural Sciences and Engineering Research Council of Canada
Openalex Percentile: Top 67%
Crystal structures of chemical compounds
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Synthesis and structure of <i>N</i> -(perfluorophenyl)isonicotinamide — Garry S. Hanan, Mihaela Cibian, et al. · Acta Crystallographica Section E Crystallographic Communications (2025) | TGRS Research Map | TGRS