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In the title compound, C27H30N2O4, the pyrrolidine ring adopts a twisted conformation. The indoline ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 81.7 (8)°. In the crystal, mol­ecules are linked into centrosymmetric dimers with graph-set motif R22(16) via pairs of C—H...O hydrogen bonds. The terminal ethyl group of the ester group is disordered over two sets of sites, with a site-occupancy ratio of 0.587 (11):0.413 (11).

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In the title compound, C26H31NO4, the five-membered rings of the central pyrrolizine system adopt N-envelope conformations. The ethyl acetate group adopts an extended conformation. The dihedral angle between the benzene rings is 36.6 (1)°. In the crystal, C—H...O hydrogen bonds form a zigzag chain running along the b-axis directions. The crystal structure is futher consolidated by C—H...π inter­actions.

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In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphtho­thio­phene unit is 0.056 Å. The dihedral angle between the naphtho­thio­phene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C—H...π and π–π stacking [minimum centroid–centroid separation = 3.7466 (10) Å] inter­actions are observed, which together lead to (010) sheets.
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