Tricyclo[3.3.1.03,7]nonane-3,7-diyl bis(4-methylbenzenesulfonate)

The title compound, C23H26O6S2 was synthesized by esterification of tricyclo[3.3.1.03,7]nonane-3,7-diol with p-toluenesulfonyl chloride. The molecule has symmetry 2 and is situated on site 4e. The C—C bond length between the quartenary C atoms is 1.598 (2) Å, which is considerably longer than other C—C bonds in the molecule. There are C—H⋯O interactions present in the structure. As a consequence, the packing of the molecule (viewed along [100]) appears as chains where the molecules run parallel, but each chain has the opposite direction to the neighboring ones.

The title compound, C 23 H 26 O 6 S 2 was synthesized by esterification of tricyclo[3.3.1.0 3,7 ]nonane-3,7-diol with p-toluenesulfonyl chloride. The molecule has symmetry 2 and is situated on site 4e. The C-C bond length between the quartenary C atoms is 1.598 (2) Å , which is considerably longer than other C-C bonds in the molecule. There are C-HÁ Á ÁO interactions present in the structure. As a consequence, the packing of the molecule (viewed along [100]) appears as chains where the molecules run parallel, but each chain has the opposite direction to the neighboring ones.

Comment
The tosyl group is one of the best leaving groups (Hoffman, 1965). For this reason, the title compound was synthesized in attempt to form new good precursors for noradamantene ( Fig. 1, Borden (1989Borden ( , 1996; Vazquez & Camps, 2005).
These three compounds have the same noradamantane skeleton ( Fig. 1) but different ligands at the C1 and C1 ipositions. There are present weak C-H···O interactions in the structure (Table 1).

Refinement
All the H atoms were discernible in the difference electron density map. However, they were situated into the idealized positions and refined with the following constraints: C-H = 0.95 Å, U iso (H)=1.2U eq (C) for aryl, and C-H = 0.98 Å, supplementary materials sup-2 Acta Cryst. (2013). E69, o1464-o1465 U iso (H)=1.5U eq (C) for the methyl atoms. The methyls were allowed to rotate about the C-C methyl bonds using the function AFIX 137 of SHELXL-97 (Sheldrick, 2008). The atom H4B which is symmetry equivalent to H4A has been treated as a dummy atom with zero occupation.

Figure 1
Schemes of noradamantane and noradamantene.

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.