Crystal structure of 2,2′-bis[(2-chlorobenzyl)oxy]-1,1′-binaphthalene

In the title binaphthyl compound, C34H24Cl2O2, the dihedral angle between the two naphthyl ring systems (r.m.s. deviations = 0.016 and 0.035 Å) is 76.33 (8)°. The chlorophenyl rings make dihedral angles of 58.15 (12) and 76.21 (13)° with the naphthyl ring to which they are linked. The dihedral angle between the planes of the two chlorophenyl rings is 27.66 (16)°. In the crystal, C—H⋯O hydrogen bonds link molecules into chains propagating along [1-10]. The chains are linked by C—H⋯π interactions, forming a three-dimensional framework.


S1. Comment
Naphthalene derivatives has been identified as new range of potent antimicrobials effective against a wide range of human pathogens. They occupy a central place among medicinally important compounds due to their diverse and interesting antibiotic properties with minimum toxicity (Rokade & Sayyed, 2009;Upadhayaya et al. 2010). Herein, we report on the synthesis and crystal structure of a new binaphthyl derivative.
The molecular structure of the title compound is shown in Fig. 1 Fig. 3).

S2. Synthesis and crystallization
The title compound was synthesized by reacting two equivalents of 2-chloro benzylbromide with one equivalent of S-BINOL in dry DMF in the presence of K 2 CO 3 at 333 K, which successfully provided the pure title product as a colourless solid. The product was dissolved in chloroform and heated for 2 min. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 18 h resulting in the formation of single crystals.

S3. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
The crystal packing of the title compound, viewed along the a axis. The intermolecular interactions are shown as dashed lines (see Table 1).

Figure 3
A partial view of the crystal packing of the title compound, showing the C-H···π interactions as dashed lines (see Table   1).  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.35 e Å −3 Δρ min = −0.47 e Å −3 Absolute structure: Flack (1983), 1709 (76%) Friedel pairs Absolute structure parameter: −0.01 (8) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. Hydrogen-bond geometry (Å, º) Cg5 is the centroid of the C19-C24 ring. Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1, y, −z+2; (iii) −x+1/2, y−1/2, −z+1.