1,3,5,7-Tetra-kis(4-iodo-phen-yl)adamantane benzene tetra-solvate.

The title mol-ecule, C(34)H(28)I(4)·4C(6)H(6), has crystallographic symmetry and crystallizes with four symmetry-related benzene solvent mol-ecules. The phenyl group is eclipsed with one of the adamantane C-C bonds. The tetra-phenyl-adamantane units and the benzene solvent mol-ecules are connected by weak inter-molecular phen-yl-benzene C-H⋯π and benzene-benzene C-H⋯π inter-actions. In the crystal, mol-ecules are linked along the c-axis direction via the iodo-phenyl groups by a combination of weak inter-molecular I⋯I [3.944 (1) Å] and I⋯π(phen-yl) [3.608 (6) and 3.692 (5) Å] inter-actions.

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 = 1256.60

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.05

2953 reflections

141 parameters

H-atom parameters constrained

Δρmax = 1.76 e Å−3

Δρmin = −0.82 e Å−3

Absolute structure: Flack (1983 ▶), 1263 Friedel pairs

Flack parameter: −0.01 (4)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C34H28I4·4C6H6	Dx = 1.616 Mg m−3
Mr = 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

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

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(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2953 reflections	Δρmax = 1.76 e Å−3
141 parameters	Δρmin = −0.82 e Å−3
0 restraints	Absolute structure: Flack (1983), 1263 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (4)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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···Cg2iv	0.95	2.85	3.733 (9)	156

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) ; (ii) .