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

Bats, J.W.; Pospiech, S.; Prisner, T.F.

doi:10.1107/S1600536810021744

Volume 66
Part 7
Page o1636
July 2010

Received 2 June 2010
Accepted 7 June 2010
Online 16 June 2010

Key indicators
Single-crystal X-ray study
T = 164 K
Mean (C-C) = 0.008 Å
R = 0.040
wR = 0.105
Data-to-parameter ratio = 20.9
Details

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

Jan W. Bats,^a ^* Steffen Pospiech ^b and Thomas F. Prisner ^b

^aInstitut für Organische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany, and ^bInstitut für Physikalische und Theoretische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
Correspondence e-mail: bats@chemie.uni-frankfurt.de

The title molecule, C₃₄H₂₈I₄·4C₆H₆, has crystallographic $[\overline{4}]$ 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-H [pi] and benzene-benzene C-H [pi] interactions. In the crystal, molecules are linked along the c-axis direction via the iodophenyl groups by a combination of weak intermolecular II [3.944 (1) Å] and I [pi] (phenyl) [3.608 (6) and 3.692 (5) Å] interactions.

Related literature

For the preparation of the title compound, see: Li et al. (2002). For the crystal structure of a related compound, see: Boldog et al. (2009). For intermolecular interactions of I atoms, see: Pedireddi et al. (1994); Thaimattam et al. (1998)

Experimental

Crystal data

C₃₄H₂₈I₄·4C₆H₆
M_r = 1256.60
Tetragonal, $[P \overline 42_1 c ]$
a = 18.883 (3) Å
c = 7.2442 (19) Å
V = 2583.1 (9) Å³
Z = 2
Mo K radiation
= 2.45 mm^-1
T = 164 K
0.60 × 0.20 × 0.12 mm

Data collection

Siemens SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.509, T_max = 0.751
35313 measured reflections
2953 independent reflections
2365 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.105
S = 1.05
2953 reflections
141 parameters
H-atom parameters constrained
_max = 1.76 e Å^-3
_min = -0.82 e Å^-3
Absolute structure: Flack (1983), 1263 Friedel pairs
Flack parameter: -0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 represent the midpoint of the C13-C14 bond and the centroid of the C10-C15 ring, respectively.

D-HA	D-H	HA	DA	D-HA
C5-H5ACg1ⁱ	0.95	2.91	3.833 (9)	163
C10-H10ACg2ⁱⁱ	0.95	2.85	3.733 (9)	156
Symmetry codes: (i) y, -x+1, -z+1; (ii) $[-y+{\script{1\over 2}}, -x+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5063 ).

References

Boldog, I., Lysenko, A. B., Rusanov, E. B., Chernega, A. N. & Domasevitch, K. V. (2009). Acta Cryst. C65, o248-o252.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Li, Q., Rukavishnikov, A. V., Petukhov, P. A., Zaikova, T. O. & Keana, J. F. W. (2002). Org. Lett. 4, 3631-3634.
Pedireddi, V. R., Reddy, D. S., Goud, B. S., Craig, D. C., Rae, A. D. & Desiraju, G. R. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 2353-2360.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Thaimattam, R., Reddy, D. S., Xue, F., Mak, T. C. W., Nangia, A. & Desiraju, G. R. (1998). New J. Chem. pp. 143-148.

organic compounds