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In the title compound, C23H21N3O3, the indole ring is planar and the phenyl ring of the benzyl group makes a dihedral angle with the best plane of the indole ring of 73.77 (4)°. The double bond connecting the aza­bicyclic and indole moieties has Z geometry.

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In crystals of the title compound, C23H23N5O3S, the indole system is planar and the phenyl ring of the phenylsulfonyl group makes a dihedral angle with the best plane of the indole system of 77.18 (4)°. The olefinic bond connecting the aza­bicyclic and indole systems has Z geometry. The geometry adopted by the C=O bond with respect to the N-N bond is trans. The O atom of the carbonyl group of each mol­ecule is hydrogen bonded to the hydrazidic H atom of an adjacent mol­ecule to form an eight-membered-ring dimeric structure.

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The asymmetric unit of the racemic form of the title compound, C12H15NOS, contains four crystallographically independent mol­ecules. The olefinic bond connecting the 2-­thienyl and 1-aza­bicyclo­[2.2.2]octan-3-ol moieties has Z geometry. Strong hydrogen bonding occurs in a directed co-operative O—H...O—H...O—H...O—H R44(8) pattern that influences the conformation of the mol­ecules. Co-operative C—H...π inter­actions between thienyl rings are also present. The average dihedral angle between adjacent thienyl rings is 87.09 (4)°.

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The title compounds, C20H17NO3S, (I), and C19H15NO2S, (II), were prepared by the reaction of benzo[b]thio­phene-2-carbaldehyde with (3,4,5-trimethoxy­phenyl)­acetonitrile and (3,4-dimethoxy­phenyl)­acetonitrile, respectively, in the presence of methanolic potassium hydroxide. In (I), the C=C bond linking the benzo[b]thio­phene and the 3,4,5-trimethoxy­phenyl units has E geometry, with dihedral angles between the plane of the bridging unit and the planes of the two adjacent ring systems of 5.2 (3) and 13.1 (2)°, respectively. However, in (II), the C=C bond has Z geometry, with dihedral angles between the plane of the bridging unit and the planes of the adjacent benzo[b]thio­phene and 3,4-dimethoxy­phenyl units of 4.84 (17) and 76.09 (7)°, respectively. There are no significant inter­molecular hydrogen-bonding inter­actions in the packing of (I) and (II). The packing is essentially stabilized via van der Waals forces.
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