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The title compound, C20H23FN2O4, is the product of a ring-expansion reaction from a seven-membered fluorinated hexahydroazepine to a nine-membered azonine. The nine-membered azonine ring of the molecule adopts a chair-boat conformation. The C=C and C--N bond lengths [1.366(3) and 1.407(3)Å, respectively] indicate the presence of conjugation within the enamine CH2--C=C--N--CH2 fragment. The substituent planes at the C=C double bond of this fragment are twisted by 16.0(3)° as a result of steric effects. The amine N(Et) N atom has a trigonal-pyramidal configuration (sum of the bond angles = 346.3°). The interplanar angle between the two carboxylate substituents is 60.39(8)°. In the crystal, molecules form zigzag chains along [010] by intermolecular N--H...O hydrogen-bonding interactions, which are further packed in stacks toward [100]. The title azoninoindole might be considered as a candidate for the design of new Alzheimer drugs. [ABSTRACT FROM AUTHOR]

The title compound, C20H24N2O4, is the product of a ring-expansion reaction from a seven-membered hexahydroazepine to a nine-membered azonine. The azonine ring of the molecule adopts a chair-boat conformation. In the crystal, molecules are linked by bifurcated N--H⋯(O,O) hydrogen bonds, generating [010] zigzag chains. The title compound shows inhibitory activity against acetylcholinesterase and butyrylcholinesterase, and might be considered as a candidate for the design of new types of anti-Alzheimer's drugs. [ABSTRACT FROM AUTHOR]

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamothioyl)amide (r.m.s. deviation = 0.038 Å ), and the second consists of the thiazole and two phenyl rings (r.m.s. deviation = 0.053 Å ). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thiazol-2-ylcarbamothioyl)amide (r.m.s. deviation = 0.084 Å ), and the two others comprise the bromophenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intramolecular N-H...O hydrogen bond, which closes an S(6) ring. In the crystal of (I), molecules form hydrogen-bonded layers parallel to (100) mediated by N-H...S and C-H...O hydrogen bonds. In the crystal of (II), molecules form a three-dimensional framework mediated by N-H...Br and C-H...O hydrogen bonds, as well as secondary S...Br [3.3507 (11) Å] and S...S [3.4343 (14) Å] interactions. [ABSTRACT FROM AUTHOR]