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The crystal of the title compound, C21H23NO2, was chosen from a conglomerate formed by a racemic mixture. An intra­molecular hydrogen bond is formed between hy­droxy group and heterocyclic N atom of the aza­bicyclo­[3.2.1]octan-3-one system. The crystal structure is stabilized by C—H...O inter­actions between aliphatic C—H groups and the carbonyl O atom. For the title chiral crystal, the highly redundant and accurate diffraction data set collected with low energy copper radiation gave a Flack parameter of 0.12 (18) for anomalous scattering effects originating from O atoms.

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In the crystal structure of the racemic title compound, C22H25NO2, solved and refined against sychrotron diffraction data, the hy­droxy group and the carbonyl O atom participate in the formation of O—H...O hydrogen bonds between pairs of enanti­omers related by a crystallographic centre of symmetry.

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The asymmetric unit of the title compound, [Ru(C15H11N3)2](ClO4)2·0.5H2O, contains one ruthenium–terpiridine complex cation, two perchlorate anions and one half-mol­ecule of water. Face-to-face and face-to-edge π-stacking inter­actions between terpyridine units [centroid–centroid distances = 3.793 (2) and 3.801 (2)  Å] stabilize the crystal lattice The partially occupied water mol­ecule inter­acts with two perchlorate ions via O—H...O hydrogen bonds. In the crystal lattice, the complex cations, perchlorate ion-water pairs and the second perchlorate anions are arranged into columns along b direction.

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The asymmetric unit of the title compound, [Ru(C12H8N2)3](ClO4)2, contains one octahedrally coordinated RuII cation of the ruthenium-phenanthroline complex and three differently occupied perchlorate anions: two, denoted A and B, are located on the twofold axis while another, denoted C, is positioned in the proximity of the twofold screw axis. Perchlorate anions B and C are severely disordered. The occupancies of the two major conformers of anion B refined to 0.302 (6) and 0.198 (6). Perchlorate ion C was modeled in two alternate conformations which refined to occupancies of 0.552 (10) and 0.448 (10).
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