[2,6-Bis(biphenyl-4-yl)-4-hy­droxy-4-(pyridin-2-yl)cyclo­hexane-1,3-di­yl]bis­[(pyridin-2-yl)methanone]–butan-2-one (1/1)

Acta Crystallographica Section E Structure Reports Online (Impact Factor: 0.35). 06/2012; 68(Pt 6):o1633-4. DOI: 10.1107/S1600536812019241
Source: PubMed


In the title solvate, C(47)H(37)N(3)O(3)·C(4)H(8)O, the cyclo-hexane ring adopts a chair conformation and the plane through its near coplanar atoms forms dihedral angles of 82.58 (7), 89.27 (7), 60.30 (8), 54.54 (7) and 72.03 (7)°, respectively, with the three pyridine rings and the two attached benzene rings. The rings of the biphenyl units are twisted from each other, making dihedral angles of 35.27 (7) and 45.41 (7)°. All the rings are in equatorial orientations in the cyclo-hexane ring, except for the C=O-bonded pyridine ring in position 1, which is axial. Intra-molecular O-H⋯N and C-H⋯O hydrogen bonds form one S(5) and three S(6) ring motifs. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into a chain along the c axis. The crystal structure also features weak C-H⋯π inter-actions and aromatic π-π stacking [centroid-centroid distances = 3.5856 (10) and 3.7090 (9) Å].

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    ABSTRACT: Three highly-substituted cyclohexanol derivatives have been prepared from 2-acetylpyridine and 4-halogenobenzaldehydes under mild conditions. (1RS,2SR,3SR,4RS,5RS)-3,5-Bis(4-fluorophenyl)-2,4-bis(pyridine-2-carbonyl)-1-(pyridin-2-yl)cyclohexanol, C35H27F2N3O3, (I), (1RS,2SR,3SR,4RS,5RS)-3,5-bis(4-chlorophenyl)-2,4-bis(pyridine-2-carbonyl)-1-(pyridin-2-yl)cyclohexanol acetone 0.951-solvate, C35H27Cl2N3O3·0.951C3H6O, (II), and (1RS,2SR,3SR,4RS,5RS)-3,5-bis(4-bromophenyl)-2,4-bis(pyridine-2-carbonyl)-1-(pyridin-2-yl)cyclohexanol, C35H27Br2N3O3, (III), all crystallize in different space groups, viz. Pbca, Fdd2 and P, respectively. In compound (II), the acetone molecule is disordered over two sets of atomic sites having occupancies of 0.690 (13) and 0.261 (13). Each of the cyclohexanol molecules contains an intramolecular O—H...N hydrogen bond and their overall molecular conformations are fairly similar. The molecules of (I) are linked by two independent C—H...O hydrogen bonds to form a C(5)C(10)[R22(15)] chain of rings, and those of (III) are linked by a combination of C—H...O and C—H...N hydrogen bonds, forming a chain of alternating R22(16) and R22(18) rings. The cyclohexanol molecules in (II) are linked by a single C—H...N hydrogen bond to form simple C(4) chains and these chains are linked by a π–π stacking interaction to form sheets, to which the disordered acetone molecules are weakly linked via a number of C—H...O contacts.
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