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The anti-inflammatory and cytoprotective tricyclic title compound, C21H18N2O2, also known as TBE-31, crystallizes with two nearly superimposable mol­ecules in the asymmetric unit. In both mol­ecules, the three ring systems conform to an envelope–chair–planar arrangement. The central ring, in a cyclohexane chair conformation, contains an axial ethynyl group that bends slightly off from a nearby axial methyl group because of the 1,3-diaxial repulsion between the two groups. In the crystal, weak C—H...N and C—H...O inter­actions form chains along [001].

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In the title compound, C17H13NO2, two mol­ecules crystallize in the asymmetric unit. The dihedral angle between the mean planes of the quinoline and benzene rings are 78.3 (4) and 88.2 (3)°. The carboxyl­ate group is twisted slightly from the quinoline ring by 7.1 (2) and 13.3 (4)°, respectively. In the crystal, weak C—H...O inter­actions are observed. Further stabilization is provided by weak π–π stacking inter­actions, with centroid–centroid distances of 3.564 (9)/3.689 (2) and 3.830 (1)/3.896 (5)Å, respectively.
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