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Updated: May 27, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-2-[1-(1-Benzothio-phen-2-yl)ethyl-idene]-N-phenyl-hydrazinecarboxamide
Abstract:
The title compound, C(17)H(15)N(3)OS, crystallizes with two unique mol-ecules, denoted 1 and 2, in the asymmetric unit. The two mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both mol-ecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothio-phene groups and N-bound phenyl rings are 36.36 (9)° for mol-ecule 1 and 29.71 (9)° for mol-ecule 2. The C=N-NH-C(O)NH ethyl-idene-hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 Å, respectively, for the two mol-ecules. The methyl substituents lie 0.338 (3) and 0.396 (3) Å, respectively, from these planes. The C=N-NH-C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)°, respectively, in mol-ecules 1 and 2. This conformation is enhanced by weak intra-molecular C-H⋯O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each mol-ecule. In the crystal, pairs of mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds into dimers. Alternating dimers are further inter-connected by weak C-H⋯O contacts into zigzag rows along b. The rows are stacked along a by C-H⋯π contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothio-phene units.
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