Synthesis, mol-ecular and crystal structures of 4-amino-3,5-di-fluoro-benzo-nitrile, ethyl 4-amino-3,5-di-fluoro-benzoate, and diethyl 4,4'-(diazene-1,2-di-yl)bis-(3,5-di-fluoro-benzoate).

Autor: Novikov EM; Department of Chemistry New Mexico Highlands University,Las Vegas New Mexico 87701 USA., Guillen Campos J; Department of Chemistry and Biochemistry University of California Santa Barbara Santa Barbara CA 93106 USA., Read de Alaniz J; Department of Chemistry and Biochemistry University of California Santa Barbara Santa Barbara CA 93106 USA., Fonari MS; Institute of Applied Physics, Academy Str., 5 MD2028, Chisinau, Moldova., Timofeeva TV; Department of Chemistry New Mexico Highlands University,Las Vegas New Mexico 87701 USA.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2024 Jul 19; Vol. 80 (Pt 8), pp. 867-872. Date of Electronic Publication: 2024 Jul 19 (Print Publication: 2024).
DOI: 10.1107/S2056989024006819
Abstrakt: The crystal structures of two inter-mediates, 4-amino-3,5-di-fluoro-benzo-nitrile, C 7 H 4 F 2 N 2 ( I ), and ethyl 4-amino-3,5-di-fluoro-benzoate, C 9 H 9 F 2 NO 2 ( II ), along with a visible-light-responsive azo-benzene derivative, diethyl 4,4'-(diazene-1,2-di-yl)bis-(3,5-di-fluoro-benzoate), C 18 H 14 F 4 N 2 O 4 ( III ), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The mol-ecules of I and II demonstrate the quinoid character of phenyl rings accompanied by the distortion of bond angles related to the presence of fluorine substituents in the 3 and 5 ( ortho ) positions. In the crystals of I and II , the mol-ecules are connected by N-H⋯N, N-H⋯F and N-H⋯O hydrogen bonds, C-H⋯F short contacts, and π-stacking inter-actions. In crystal of III , only stacking inter-actions between the mol-ecules are found.
(© Novikov et al. 2024.)
Databáze: MEDLINE
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