Crystal structure of (4-chlorophenyl)[2-(10-hydroxyphenanthren-9-yl)phenanthro[9,10-b]furan-3-yl]methanone

Molecules of the title compound are arranged in the solid state in a three-dimensional supramolecular architecture via intermolecular O—H⋯O and C—H⋯O hydrogen bonding and through C—H⋯π interactions.


Chemical context
Furan and its derivatives have in recent years again attracted the attention of researchers from various areas of chemistry (Uchuskin et al., 2014;Liu et al., 2013). The dihydrofuran core framework was identified in many natural products and in drugs with remarkable biological activities (Michael, 2000;Lipshutz, 1986), inspiring the development of new synthetic methods for the construction of functionalized furans (Singh & Batra, 2008;Snider, 1996;Ranu et al., 2008;Redon et al., 2008;Adamo et al., 2009). As for most organic syntheses, furans are often synthesized in stepwise sequences. However, it is much more efficient if one can form several bonds in one sequence without isolating the intermediates, changing the reaction conditions, or adding reagents (Tietze & Beifuss, 1993). This type of reaction, commonly termed a domino reaction (Muthusaravanan et al., 2013;Kadzimirsz et al., 2008;Criado et al., 2013) would allow a substantial reduction of waste compared to stepwise reactions. The amount of solvents, reagents, adsorbents, and energy would also be dramatically decreased.
The title compound of this report has been obtained using such a domino reaction. Using a tandem Michael-aldol reaction of phenanthrenequinone (1) with 4-chloroacetophenone (2) we were able to obtain the highly substituted furan (3) and the 3(2H)-furanone (4) (Jacob et al., 2005) in one simple multicomponent reaction.

Structural commentary
In the title compound, (3), the two phenanthrene moieties make a dihedral angle of 57.79 (5) , while one of the phenanthrene moieties is fused together with the furan ring in an almost coplanar arrangement [5.14 (8) ] (Fig. 1). The central furan ring makes dihedral angles of 70.27 (11) and 57.58 (8) with the phenyl ring and the other phenanthrene moieties, respectively. These two attached rings are twisted so that the C O oxygen atom points away from the phenanthrene ring. This conformation is stabilized by intramolecular hydrogen bonds between the H atoms attached to atoms C11 and C26 towards O1 and O2, respectively (see Table 1 for numerical values).

Supramolecular features
There are several intermolecular hydrogen-bonding interactions present in the molecular crystal. Carbonyl atom O1 acts as an acceptor for three hydrogen bonds; the intramolecular C-HÁ Á ÁO hydrogen bond with the H atom attached to C11, see above, and two intermolecular hydrogen bonds involving atoms O3 and C35 of a neighbouring mol- Hydrogen-bonding interactions found in the title compound (see Table 1 for details). Table 1 Hydrogen-bond geometry (Å , ).

Figure 3
C-HÁ Á Á interactions found in the title compound.

Figure 1
View of the title compound (3) with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
ecule. The latter two intermolecular hydrogen-bonding interactions lead to formation of an inversion dimer. Another nonclassical hydrogen-bonding interaction with the Cl atom of a neighbouring molecule as the acceptor connects these dimers, forming zigzag chains propagating in the b-axis direction (Fig. 2). Three C-HÁ Á Á interactions ( Fig. 3) are found in the crystal. The first two C-HÁ Á Á interactions are between the H atoms attached to C13 and C17 and the outer two aromatic rings of one of the phenanthrene moieties of an adjacent molecule with CÁ Á Á distances of 3.709 (3) and 3.745 (2) Å . The third C-HÁ Á Á interaction occurs between atom C32 and the central aromatic ring of the other phenanthrene moiety (see Table 1 for numerical values and symmetry operators of O-HÁ Á ÁO, C-HÁ Á ÁO and C-HÁ Á Á interactions). Fig. 4 shows the packing diagram of the title compound along a axis.

Figure 4
Packing diagram of the title compound along the a axis.

Figure 5
Reaction scheme showing the synthesis of the title compound (