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

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

doi:10.1107/S1600536810021744

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1636

doi:10.1107/S1600536810021744

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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

(Received 2 June 2010; accepted 7 June 2010; online 16 June 2010)

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⋯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.

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 Kα radiation
μ = 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 > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.05
2953 reflections
141 parameters
H-atom parameters constrained
Δρ_max = 1.76 e Å⁻³
Δρ_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—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 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021744/lh5063sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021744/lh5063Isup2.hkl

checkCIF report

Comment top

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 C5—C4—C2—C3ⁱ = 5.7 (6)° [symmetry i: y, 1 - x, 1 - z]).

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.

Each C—I bond points to the iodophenyl group of a neighboring molecule as shown in Fig. 3. The shortest contact distances are: I1···I1ⁱ = 3.944 (1) Å, I1···C6ⁱ = 3.608 (6)Å and I1···C7ⁱ = 3.692 (5)Å (symmetry i: 1/2 - y, 1/2 - x, -1/2 + z). The angles for these contacts are: C7—I1···I1ⁱ = 158.6 (1)°, C7—I1···C6ⁱ = 153.9 (2)° and C7—I1···C7ⁱ = 167.0 (2)°. This combination of weak interactions link the 1,3,5,7-tetrakis(4-iodophenyl)adamantane molecules along the c direction. The significance of these interactions for crystal packing has been discussed by Pedireddi et al. (1994) and Thaimattam et al. (1998).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); 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 (Sheldrick, 2008).

Figures top

	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.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. C—H···π contacts are shown as dotted lines.
	Fig. 3. Section of the crystal structure showing the linking of the 1,3,5,7-tetrakis(4-iodophenyl)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.

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

Crystal data top

C₃₄H₂₈I₄·4C₆H₆	D_x = 1.616 Mg m⁻³
M_r = 1256.60	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 103 reflections
Hall symbol: P -4 2n	θ = 3–23°
a = 18.883 (3) Å	µ = 2.45 mm⁻¹
c = 7.2442 (19) Å	T = 164 K
V = 2583.1 (9) Å³	Rod, colorless
Z = 2	0.60 × 0.20 × 0.12 mm
F(000) = 1224

Data collection top

Siemens SMART 1K CCD diffractometer	2953 independent reflections
Radiation source: normal-focus sealed tube	2365 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −24→24
T_min = 0.509, T_max = 0.751	k = −24→24
35313 measured reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.06P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2953 reflections	Δρ_max = 1.76 e Å⁻³
141 parameters	Δρ_min = −0.82 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1263 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (4)

Crystal data top

C₃₄H₂₈I₄·4C₆H₆	Z = 2
M_r = 1256.60	Mo Kα radiation
Tetragonal, P42₁c	µ = 2.45 mm⁻¹
a = 18.883 (3) Å	T = 164 K
c = 7.2442 (19) Å	0.60 × 0.20 × 0.12 mm
V = 2583.1 (9) Å³

Data collection top

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

Refinement top

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

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.25295 (2)	0.30544 (2)	−0.23303 (6)	0.05317 (17)
C1	0.5000	0.5000	0.2564 (9)	0.0199 (12)
H1A	0.5258	0.4664	0.1760	0.024*	0.50
H1B	0.4742	0.5336	0.1760	0.024*	0.50
C2	0.4466 (2)	0.4589 (2)	0.3747 (6)	0.0195 (9)
C3	0.4875 (3)	0.4074 (2)	0.5016 (6)	0.0209 (9)
H3A	0.4534	0.3815	0.5804	0.025*
H3B	0.5129	0.3723	0.4248	0.025*
C4	0.3977 (2)	0.4186 (2)	0.2437 (6)	0.0222 (8)
C5	0.3250 (2)	0.4344 (2)	0.2272 (7)	0.0274 (10)
H5A	0.3039	0.4677	0.3087	0.033*
C6	0.2844 (3)	0.4020 (3)	0.0937 (6)	0.0287 (11)
H6A	0.2354	0.4131	0.0842	0.034*
C7	0.3139 (3)	0.3534 (3)	−0.0265 (6)	0.0310 (11)
C8	0.3848 (3)	0.3345 (3)	−0.0094 (7)	0.0282 (11)
H8A	0.4052	0.3000	−0.0885	0.034*
C9	0.4250 (3)	0.3675 (3)	0.1261 (6)	0.0279 (10)
H9A	0.4734	0.3544	0.1388	0.034*
C10	0.4526 (5)	0.1182 (4)	0.7048 (12)	0.083 (2)
H10A	0.4384	0.0903	0.8073	0.099*
C11	0.5184 (5)	0.1096 (5)	0.6257 (15)	0.081 (3)
H11A	0.5501	0.0748	0.6719	0.097*
C12	0.5372 (4)	0.1500 (4)	0.4852 (13)	0.072 (2)
H12A	0.5831	0.1449	0.4335	0.086*
C13	0.4918 (4)	0.1992 (4)	0.4127 (10)	0.066 (2)
H13A	0.5055	0.2268	0.3089	0.080*
C14	0.4265 (4)	0.2084 (4)	0.4909 (11)	0.0612 (19)
H14A	0.3947	0.2432	0.4445	0.073*
C15	0.4085 (5)	0.1681 (4)	0.6319 (14)	0.078 (3)
H15A	0.3628	0.1740	0.6849	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0530 (2)	0.0577 (3)	0.0488 (2)	0.00188 (19)	−0.0243 (2)	−0.0168 (2)
C1	0.023 (3)	0.022 (3)	0.015 (3)	0.000 (2)	0.000	0.000
C2	0.021 (2)	0.023 (2)	0.015 (2)	−0.0026 (18)	−0.0018 (17)	−0.0024 (17)
C3	0.026 (2)	0.020 (2)	0.017 (2)	−0.001 (2)	−0.0010 (18)	−0.0001 (17)
C4	0.026 (2)	0.026 (2)	0.015 (2)	−0.0043 (16)	0.0018 (19)	0.0027 (19)
C5	0.029 (2)	0.024 (2)	0.029 (2)	−0.0014 (17)	0.006 (2)	0.005 (2)
C6	0.019 (2)	0.031 (3)	0.036 (3)	−0.006 (2)	−0.002 (2)	0.000 (2)
C7	0.031 (3)	0.035 (3)	0.027 (2)	−0.008 (2)	−0.009 (2)	0.001 (2)
C8	0.030 (3)	0.029 (3)	0.026 (2)	0.002 (2)	−0.002 (2)	−0.004 (2)
C9	0.024 (2)	0.028 (3)	0.032 (2)	0.001 (2)	−0.002 (2)	−0.002 (2)
C10	0.105 (7)	0.070 (5)	0.073 (6)	−0.003 (5)	0.014 (5)	0.010 (4)
C11	0.071 (5)	0.066 (5)	0.106 (7)	−0.001 (5)	−0.030 (5)	0.012 (5)
C12	0.045 (4)	0.062 (5)	0.109 (7)	−0.011 (4)	0.013 (4)	−0.020 (5)
C13	0.080 (5)	0.045 (4)	0.074 (5)	−0.020 (4)	0.013 (4)	−0.020 (4)
C14	0.065 (5)	0.029 (4)	0.089 (5)	−0.007 (3)	−0.004 (4)	−0.008 (3)
C15	0.074 (6)	0.053 (5)	0.108 (7)	0.000 (4)	0.018 (5)	−0.027 (5)

Geometric parameters (Å, º) top

I1—C7	2.093 (5)	C7—C8	1.391 (7)
C1—C2ⁱ	1.535 (5)	C8—C9	1.388 (6)
C1—C2	1.535 (5)	C8—H8A	0.9500
C1—H1A	0.9900	C9—H9A	0.9500
C1—H1B	0.9900	C10—C15	1.364 (11)
C2—C4	1.528 (6)	C10—C11	1.378 (12)
C2—C3ⁱⁱ	1.540 (6)	C10—H10A	0.9500
C2—C3	1.545 (6)	C11—C12	1.321 (12)
C3—C2ⁱⁱⁱ	1.540 (6)	C11—H11A	0.9500
C3—H3A	0.9900	C12—C13	1.369 (11)
C3—H3B	0.9900	C12—H12A	0.9500
C4—C9	1.387 (6)	C13—C14	1.368 (10)
C4—C5	1.409 (6)	C13—H13A	0.9500
C5—C6	1.378 (6)	C14—C15	1.319 (11)
C5—H5A	0.9500	C14—H14A	0.9500
C6—C7	1.382 (7)	C15—H15A	0.9500
C6—H6A	0.9500

C2ⁱ—C1—C2	112.1 (5)	C6—C7—C8	120.1 (4)
C2ⁱ—C1—H1A	109.2	C6—C7—I1	121.1 (4)
C2—C1—H1A	109.2	C8—C7—I1	118.8 (4)
C2ⁱ—C1—H1B	109.2	C9—C8—C7	118.4 (4)
C2—C1—H1B	109.2	C9—C8—H8A	120.8
H1A—C1—H1B	107.9	C7—C8—H8A	120.8
C4—C2—C1	107.6 (3)	C4—C9—C8	122.8 (4)
C4—C2—C3ⁱⁱ	113.5 (4)	C4—C9—H9A	118.6
C1—C2—C3ⁱⁱ	107.9 (3)	C8—C9—H9A	118.6
C4—C2—C3	111.0 (4)	C15—C10—C11	118.1 (8)
C1—C2—C3	108.7 (3)	C15—C10—H10A	120.9
C3ⁱⁱ—C2—C3	107.9 (3)	C11—C10—H10A	120.9
C2ⁱⁱⁱ—C3—C2	111.9 (4)	C12—C11—C10	119.6 (9)
C2ⁱⁱⁱ—C3—H3A	109.2	C12—C11—H11A	120.2
C2—C3—H3A	109.2	C10—C11—H11A	120.2
C2ⁱⁱⁱ—C3—H3B	109.2	C11—C12—C13	121.3 (8)
C2—C3—H3B	109.2	C11—C12—H12A	119.3
H3A—C3—H3B	107.9	C13—C12—H12A	119.3
C9—C4—C5	117.3 (4)	C14—C13—C12	119.5 (8)
C9—C4—C2	120.2 (4)	C14—C13—H13A	120.3
C5—C4—C2	122.4 (4)	C12—C13—H13A	120.3
C6—C5—C4	120.5 (4)	C15—C14—C13	118.7 (8)
C6—C5—H5A	119.7	C15—C14—H14A	120.7
C4—C5—H5A	119.7	C13—C14—H14A	120.7
C5—C6—C7	120.8 (5)	C14—C15—C10	122.8 (8)
C5—C6—H6A	119.6	C14—C15—H15A	118.6
C7—C6—H6A	119.6	C10—C15—H15A	118.6

C2ⁱ—C1—C2—C4	−178.4 (4)	C4—C5—C6—C7	0.0 (7)
C2ⁱ—C1—C2—C3ⁱⁱ	58.7 (3)	C5—C6—C7—C8	2.5 (7)
C2ⁱ—C1—C2—C3	−58.1 (3)	C5—C6—C7—I1	−178.8 (3)
C4—C2—C3—C2ⁱⁱⁱ	175.9 (4)	C6—C7—C8—C9	−2.3 (7)
C1—C2—C3—C2ⁱⁱⁱ	57.7 (5)	I1—C7—C8—C9	179.0 (3)
C3ⁱⁱ—C2—C3—C2ⁱⁱⁱ	−59.1 (3)	C5—C4—C9—C8	2.9 (7)
C1—C2—C4—C9	61.9 (5)	C2—C4—C9—C8	−172.9 (4)
C3ⁱⁱ—C2—C4—C9	−178.8 (4)	C7—C8—C9—C4	−0.5 (7)
C3—C2—C4—C9	−57.0 (5)	C15—C10—C11—C12	1.1 (14)
C1—C2—C4—C5	−113.7 (4)	C10—C11—C12—C13	−1.9 (13)
C3ⁱⁱ—C2—C4—C5	5.7 (6)	C11—C12—C13—C14	2.2 (12)
C3—C2—C4—C5	127.4 (4)	C12—C13—C14—C15	−1.7 (11)
C9—C4—C5—C6	−2.6 (6)	C13—C14—C15—C10	0.9 (12)
C2—C4—C5—C6	173.1 (4)	C11—C10—C15—C14	−0.6 (13)

Symmetry codes: (i) −x+1, −y+1, z; (ii) y, −x+1, −z+1; (iii) −y+1, x, −z+1.

Hydrogen-bond geometry (Å, º) top

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···Cg1ⁱⁱ	0.95	2.91	3.833 (9)	163
C10—H10A···Cg2^iv	0.95	2.85	3.733 (9)	156

Symmetry codes: (ii) y, −x+1, −z+1; (iv) −y+1/2, −x+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₈I₄·4C₆H₆
M_r	1256.60
Crystal system, space group	Tetragonal, P42₁c
Temperature (K)	164
a, c (Å)	18.883 (3), 7.2442 (19)
V (Å³)	2583.1 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.60 × 0.20 × 0.12

Data collection
Diffractometer	Siemens SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.509, 0.751
No. of measured, independent and observed [I > 2σ(I)] reflections	35313, 2953, 2365
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.05
No. of reflections	2953
No. of parameters	141
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.76, −0.82
Absolute structure	Flack (1983), 1263 Friedel pairs
Absolute structure parameter	−0.01 (4)

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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+1/2, −x+1/2, z+1/2.

References

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Volume 66| Part 7| July 2010| Page o1636

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