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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 [sigma](C-C) = 0.008 Å
R = 0.040
wR = 0.105
Data-to-parameter ratio = 20.9
Details
Open access

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

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 I...I [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[Li, Q., Rukavishnikov, A. V., Petukhov, P. A., Zaikova, T. O. & Keana, J. F. W. (2002). Org. Lett. 4, 3631-3634.]). For the crystal structure of a related compound, see: Boldog et al. (2009[Boldog, I., Lysenko, A. B., Rusanov, E. B., Chernega, A. N. & Domasevitch, K. V. (2009). Acta Cryst. C65, o248-o252.]). For intermolecular interactions of I atoms, see: Pedireddi et al. (1994[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.]); Thaimattam et al. (1998[Thaimattam, R., Reddy, D. S., Xue, F., Mak, T. C. W., Nangia, A. & Desiraju, G. R. (1998). New J. Chem. pp. 143-148.])

[Scheme 1]

Experimental

Crystal data
  • C34H28I4·4C6H6

  • Mr = 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[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.509, Tmax = 0.751

  • 35313 measured reflections

  • 2953 independent reflections

  • 2365 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.105

  • S = 1.05

  • 2953 reflections

  • 141 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.76 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 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-H...A D-H H...A D...A D-H...A
C5-H5A...Cg1i 0.95 2.91 3.833 (9) 163
C10-H10A...Cg2ii 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[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Li, Q., Rukavishnikov, A. V., Petukhov, P. A., Zaikova, T. O. & Keana, J. F. W. (2002). Org. Lett. 4, 3631-3634.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [details]
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.  [ISI] [CrossRef]


Acta Cryst (2010). E66, o1636  [ doi:10.1107/S1600536810021744 ]

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