(R)-1,1′-Binaphthalene-2,2′-diyl dicinnamate

In the title compound, C38H26O4, two cinnamoyloxy groups are linked in a trans fashion to the two O atoms of optically active (R)-1,10-bi-2-naphthol. The dihedral angle between the mean planes of the two naphthyl groups is 71.8 (1)°. The crystal structure contains intermolecular C—H⋯O and C—H⋯π interactions.

In the title compound, C 38 H 26 O 4 , two cinnamoyloxy groups are linked in a trans fashion to the two O atoms of optically active (R)-1,10-bi-2-naphthol. The dihedral angle between the mean planes of the two naphthyl groups is 71.8 (1) . The crystal structure contains intermolecular C-HÁ Á ÁO and C-HÁ Á Á interactions.
The separation between atoms O1 and O3 is 4.230 (3) Å, which is longer than that reported in other 2,2'-O-substituted complexes (Goldberg, 1980). Considerable twisting between the two naphthyl groups in the compound produces a dihedral angle 71.8 (1)°, much less than the angle of 101.7° found in (R)-BINOL itself. The naphthyl groups are also highly twisted with respect to their covalently linked phenyl groups, with dihedral angles of 28.6 (1) and 74.2 (1)°, respectively. These twists may be ascribed to steric repulsion, resulting in the two cinnamoyloxy units lying on opposite sides of the binaphthyl backbone.
The crystal structure contains C-H···O and C-H···π interactions ( Fig. 2 and Table 1). Denoting the centroids of rings

Experimental
To a 50 ml round-bottom flask was added 2.0 g (7.0 mmol) of (R)-1,1'-bi-2-naphthol, 20 ml THF and 6.6 ml pyridine. Then, 5.0 ml trans-cinnamoyl chloride (25.9 mmol) was added in an ice bath. The mixture was stirred at ambient temperature for 24 h, and then poured onto ice. The resulting solid was filtered and washed with hot water. The crude product was soaked with absolute methanol twice to afford the target compound, which was recrystallized from THF/MeOH to afford colourless blocks.

Refinement
H atoms were positioned geometrically (C-H = 0.93 Å) and allowed to ride on their respective parent C atoms with U iso (H) = 1.2 U eq (C). In the absence of significant anomalous scattering effects, 2231 Friedel pairs have been merged. Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level for non-H atoms.  supplementary materials sup-9