1,3,5,7-Tetrakis(4-iodophenyl)adamantane benzene tetrasolvate

The title molecule, C34H28I4·4C6H6, has crystallographic symmetry and crystallizes with four symmetry-related benzene solvent molecules. The phenyl group is eclipsed with one of the adamantane C—C bonds. The tetraphenyladamantane units and the benzene solvent molecules are connected by weak intermolecular phenyl–benzene C—H⋯π and benzene–benzene C—H⋯π interactions. In the crystal, molecules are linked along the c-axis direction via the iodophenyl groups by a combination of weak intermolecular I⋯I [3.944 (1) Å] and I⋯π(phenyl) [3.608 (6) and 3.692 (5) Å] interactions.

The title molecule, C 34 H 28 I 4 Á4C 6 H 6 , has crystallographic 4 symmetry and crystallizes with four symmetry-related benzene solvent molecules. The phenyl group is eclipsed with one of the adamantane C-C bonds. The tetraphenyladamantane units and the benzene solvent molecules are connected by weak intermolecular phenyl-benzene C-HÁ Á Á and benzene-benzene C-HÁ Á Á interactions. In the crystal, molecules are linked along the c-axis direction via the iodophenyl groups by a combination of weak intermolecular IÁ Á ÁI [3.944 (1) Å ] and IÁ Á Á(phenyl) [3.608 (6) and 3.692 (5) Å ] interactions.

Comment
The title compound was prepared as a precursor for the synthesis of EPR-active tetrahedral model systems.
The asymmetric unit contains a quarter of a 1,3,5,7-tetrakis(4-iodophenyl)adamantane molecule and one benzene solvent molecule. The molecular structure is shown in Fig. 1. The substituted adamantane molecule has 4 symmetry. The conformation of the tetraphenyladamantane unit is very similar to the conformation in the crystal structure of 1,3,5,7-tetraphenyladamantane (Boldog et al., 2009), with the phenyl group eclipsed with one of the adamantane C-C bonds (torsion angle The crystal packing is shown in Fig. 2. The tetraphenyladamantane and the benzene solvent molecules are connected by intermolecular C-H···π interactions (Table 1, Cg1 and Cg2 represent the midpoint of the C13-C14 bond and the centroid of the C10-C15 ring respectively). There is a C-H···π contact between the phenyl ring and a benzene solvent molecule [angle between planes of rings: 72.9 (2)°]. The C phenyl -H bond does not point to the center of the benzene ring, but closer to the midpoint of the C13-C14 bond. The benzene solvent molecules are connected along the c direction by an additional C-H···π contact. The angle between the planes of the donor and acceptor benzene molecules is 83.3 (2)° and the donor C-H bond points closely to the center of the acceptor ring.
The significance of these interactions for crystal packing has been discussed by Pedireddi et al. (1994) andThaimattam et al. (1998).

Experimental
The title compound was prepared as described by Li et al. (2002). Single crystals were obtained by recrystallization of the compound from benzene. The crystals rapidly decomposed in the air at room temperature. Therefore a crystal was taken from the mother liquor and was rapidly cooled to 164 K.

Refinement
The H atoms were positioned geometrically and treated as riding: C non-planar -H=0.99 Å, C planar -H=0.95Å and U iso (H)=1.2U eq (C). The absolute structure was determined using 1263 Friedel pairs. supplementary materials sup-2 Figures   Fig. 1. The structure of the title compound shown with 50% probability displacement ellipsoids. The H atoms are drawn as small spheres of arbitrary radius. Unlabelled atoms are related to labelled atoms by 4 symmetry.   3. Section of the crystal structure showing the linking of the 1,3,5,7-tetrakis(4iodophenyl)adamantane molecules by intermolecular contacts between the iodophenyl groups. The symmetry codes are i: 1/2 -y, 1/2 -x, -1/2 + z and ii: 1/2 -y, 1/2 -x, 1/2 + z. 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 Rfactors(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ. (