[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)

Abstract

In the title solvate, C47H37N3O3·C4H8O, the cyclo­hexane 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 cyclo­hexane ring, except for the C=O-bonded pyridine ring in position 1, which is axial. Intra­molecular O—H⋯N and C—H⋯O hydrogen bonds form one S(5) and three S(6) ring motifs. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds into a chain along the c axis. The crystal structure also features weak C—H⋯π inter­actions and aromatic π–π stacking [centroid–centroid distances = 3.5856 (10) and 3.7090 (9) Å].

Three closely-related cyclohexanols (C35H27X2N3O3;X= F, Cl or Br): similar molecular structures but different crystal structures

“…On this basis, the reference molecules all have the configuration (1R,2S,3S,4R,5R) and the space groups confirm that all three compounds crystallize as racemic mixtures. Compound (IV) has exactly the same stereochemistry, although this aspect of its structure was not mentioned in the original structure report (Fun et al, 2012). The isolated yields of the (1RS,2SR,3SR,4RS,5RS) forms for compounds (I)-(IV), in the range 64-74%, suggest a high degree of stereoselectivity in the formation of the substituted cyclohexane ring.…”

“…Glidewell et al, 2005;Nayak et al, 2014). [2,6-Bis(biphenyl-4-yl)-4-hydroxy-4-(pyridin-2-yl)-cyclohexane-1,3-diyl]bis[(pyridin-2-yl)methanone]-butan-2one (1/1), (IV), crystallizes in the space group P2 1 /c as a stoichiometric 1:1 solvate with butanone, although the reported synthetic procedure for (IV) specifies that the compound was crystallized from acetone (Fun et al, 2012). The cyclohexanol molecules in compounds (I)-(III) contain five stereogenic centres and, for each compound, the reference molecule was selected as one having the R configuration at atom C1 (Figs.…”

“…In compound (IV) (Fun et al, 2012), the supramolecular assembly consists of C(5) chains containing molecules related by c-glide planes which are linked by a single C-HÁ Á ÁO hydrogen bond, and the butanone solvent molecules are linked to these chains, also via C-HÁ Á ÁO hydrogen bonds.…”

“…Part of the crystal structure of compound(IV), showing thestacking interaction which links hydrogen-bonded chains along [001] into a sheet parallel to (100). The original atomic coordinates(Fun et al, 2012) have been used. For the sake of clarity, the H atoms, the solvent molecules and the unit-cell outline have been omitted.…”

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

“…In addition to the parent compound (Ar = Ar 1 = C 6 H 5 ) [39,40,41,42,43,44,45,46], a large number of derivatives with carbocyclic Ar and Ar 1 substituents have been obtained from reactions of substituted benzaldehydes and acetophenones [34,41,43,46,47,48,49,50,51,52,53]. Of most relevance to the chemistry reported in this manuscript, are compounds with heterocyclic substituents and, to date, examples with thiophen-2-yl [34,41,54,55,56], furan-2-yl [54,57], benzofuran-2-yl [33], benzofuran-3-yl [33], benzothiophen-2-yl [33], benzothiophen-3-yl [33], pyridin-2-yl [33,35,45,58,59,60,61,62,63,64,65,66] pyridin-3-yl [33,45,56] and pyridin-4-yl [16,20,33,45,56,67] groups have been reported. Cave and Raston have commented that reactions of 4-acetylpyridine with 4-alkoxybenzaldehydes in solution only yield the 3:2 products rather than the desired 4,2′:6′,4″-terpyridines [16,20].…”