1,3-Bis{[(4-methylphenyl)sulfonyl]oxy}propan-2-yl 4-methylbenzenesulfonate

In the title sulfonate derivative, C24H26O9S3, all atoms apart from those of one of the 4-methylbenzenesulfonate residues lie approximately in a disc; the dihedral angles between the approximately orthogonal benzene ring and those in the plane are 74.53 (9) and 67.79 (11)°. In the crystal, molecules are consolidated into the three-dimensional architecture by C—H⋯O interactions. One of the 4-methylbenzenesulfonate residues is disordered over two almost parallel positions; the major component refined to a site-occupancy factor of 0.918 (2).

In the title sulfonate derivative, C 24 H 26 O 9 S 3 , all atoms apart from those of one of the 4-methylbenzenesulfonate residues lie approximately in a disc; the dihedral angles between the approximately orthogonal benzene ring and those in the plane are 74.53 (9) and 67.79 (11) . In the crystal, molecules are consolidated into the three-dimensional architecture by C-HÁ Á ÁO interactions. One of the 4-methylbenzenesulfonate residues is disordered over two almost parallel positions; the major component refined to a site-occupancy factor of 0.918 (2).

Tiekink Comment
In continuation of the related structural studies (Al-Mohammed et al., 2011), the crystal structure determination of the title compound, (I), is now described. Compound (I) has been patented as a stabilizer for thermal recording materials (Matsumoto et al., 1996).
In (I), Fig. 1, each carbon of the propyl residue is connected to a 4-methylbenzenesulfonate residue. The S1-and S2containing residues are approximately co-planar with the central propyl chain with the dihedral angle between their benzene rings being 51.00 (11)°. By contrast, the S3-containing 4-methylbenzenesulfonate projects almost orthogonally with respect to the remaining molecule. The dihedral angles between the benzene ring of the S3-residue and those of the S1-and S2-residues are 74.53 (9) and 67.79 (11)°, respectively.
Molecules are consolidated into the three-dimensional architecture by weak C-H···O interactions, Table 1. Globally, the crystal structure comprises alternating layers of sulfonate-rich and sulfonate-poor regions that stack along the b axis,

Experimental
Glycerol (5.53 g, 0.06 mol), pyridine (4 ml, excess) and p-toluenesulfonyl chloride (9.53 g, 0.05 mol) was stirred in dichloromethane (50 ml) and monitored by thin layer chromatography. On completion of the reaction, dilute hydrochloric acid was added and the product was purified by column chromatography. Crystals were obtained upon recrystallization from its n-hexane/ether solution.

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95 to 0.98 Å, U iso (H) = 1.2 to 1.5U eq (C)] and were included in the refinement in the riding model approximation.
The tosyl group connected to the middle carbon of the glycerol fragment is disordered over two positions, with the major component having a site occupancy factor = 0.918 (2). The 1,2-as well as the 1,3-related distances of the minor component were restrained to those of the corresponding distances in the major component. The pair of C glycerol -O tolylsate distances were restrained to within 0.01 Å of each other. The anisotropic displacement parameters of the primed atoms were set to those of the unprimed ones.  The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major component of the disordered residue is shown.

Figure 2
A view in projection down the a axis of the unit-cell contents of (I). The weak C-H···O interactions are shown as orange dashed lines.