biostudies-literatureNovikov EMNSFNational Science Foundation867-872https://www.ebi.ac.uk/biostudies/studies/S-EPMC11299740biostudies-literatureUnknown80(Pt 8)The crystal structures of two inter-mediates, 4-amino-3,5-di-fluoro-benzo-nitrile, C₇H₄F₂N₂ (<b>I</b>), and ethyl 4-amino-3,5-di-fluoro-benzoate, C₉H₉F₂NO₂ (<b>II</b>), along with a visible-light-responsive azo-benzene derivative, diethyl 4,4'-(diazene-1,2-di-yl)bis-(3,5-di-fluoro-benzoate), C₁₈H₁₄F₄N₂O₄ (<b>III</b>), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The mol-ecules of <b>I</b> and <b>II</b> 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 (<i>ortho</i>) positions. In the crystalsActa crystallographica. Section E, Crystallographic communicationsSynthesis, 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).PMC11299740DMR-2122108DMR-1933487Fonari MSTimofeeva TVNovikov EMGuillen Campos JRead de Alaniz JfalseSynthesis, 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).The crystal structures of two inter-mediates, 4-amino-3,5-di-fluoro-benzo-nitrile, C₇H₄F₂N₂ (<b>I</b>), and ethyl 4-amino-3,5-di-fluoro-benzoate, C₉H₉F₂NO₂ (<b>II</b>), along with a visible-light-responsive azo-benzene derivative, diethyl 4,4'-(diazene-1,2-di-yl)bis-(3,5-di-fluoro-benzoate), C₁₈H₁₄F₄N₂O₄ (<b>III</b>), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The mol-ecules of <b>I</b> and <b>II</b> 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 (<i>ortho</i>) positions. In the crystals2024-01-01T00:00:00Z2024 Aug2025-04-26T05:31:20.658Z2025-04-06T11:34:15.606ZS-EPMC112997403910877510.1107/S2056989024006819