Synthesis, molecular and crystal structures of 4-amino-3,5-difluorobenzonitrile, ethyl 4-amino-3,5-difluorobenzoate, and diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate)
Egor M. Novikov , Jesus Guillen Campos , Javier Read de Alaniz , Marina S. Fonari , Tatiana V. Timofeeva
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引用次数: 0
Abstract
Two intermediates, 4-amino-3,5-difluorobenzonitrile, C7H4F2N2 (I), and ethyl 4-amino-3,5-difluorobenzoate, C9H9F2NO2 (II), along with a visible-light-responsive azobenzene derivative, diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate), C18H14F4N2O4 (III), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. In the crystals of I and II, the molecules are connected by N—H⋯N, N—H⋯F and N—H⋯O hydrogen bonds, C—H⋯F short contacts, and π-stacking interactions. In the crystal of III, only stacking interactions between the molecules are found.
The crystal structures of two intermediates, 4-amino-3,5-difluorobenzonitrile, C7H4F2N2 (I), and ethyl 4-amino-3,5-difluorobenzoate, C9H9F2NO2 (II), along with a visible-light-responsive azobenzene derivative, diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate), C18H14F4N2O4 (III), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The molecules 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 molecules are connected by N—H⋯N, N—H⋯F and N—H⋯O hydrogen bonds, C—H⋯F short contacts, and π-stacking interactions. In crystal of III, only stacking interactions between the molecules are found.
期刊介绍：
Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.
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