Tri­phenyl(3,4,5-tri­iodo­phenyl)­methane

The crystal structure of the title compound, alternatively called 1,2,3-triiodo-5-(triphenylmethyl)benzene, C₂₅H₁₇I₃, is analysed in terms of I...I and I...π interactions and the herring-bone T motif between phenyl groups. There are two mol­ecules in the asymmetric unit, denoted A and B. Inversion-related A mol­ecules are connected via an I...π interaction (3.641 Å, to a C—C bond mid-point) to form an I...π dimer, and these dimers are connected through symmetry-independent B mol­ecules via I...I [3.5571 (15) Å] and I...π (3.561 Å, to a C—C bond mid-point) interactions.

S1. Comment

The Cl atom is a well known steering group in crystal engineering (Sarma & Desiraju, 1986). Halogenated derivatives of tetraphenylmethane, tetrakis(4-bromophenyl)methane (Reddy et al., 1996) and tetrakis(4-iodophenyl)methane (Anthony et al., 1998) form diamondoid networks mediated by the halogen tetramer synthon. In the crystal structure of (4-iodophenyl)triphenylmethane, molecules are connected via an I···π interaction (I···phenyl centroid 3.747 Å and 146.6°) to form a zigzag network (Thaimattam et al., 1998). The crystal structure of 3,4,5-triiodotoluene has an I₄ tetramer synthon (Liu et al., 1985), in which each I atom interacts with two neighbouring I atoms [I···I distance 3.746 (1) Å, and C—I···I angles 92.1 (3) and 178.1 (3)°]. Such interactions, with C—I···I—C angles close to 90 and 180°, are referred to as type II or L geometry. These dipole-induced halogen-halogen interactions (Bosch & Barnes, 2002; Jetti Thallapally et al., 2000) have been used in crystal engineering. Against this background, we report here the crystal structure of triphenyl(3,4,5-triiodophenyl)methane, (I). \sch

The crystal structure of the title compound involves two molecules of (I), denoted A and B, in the asymmetric unit (Fig. 1). The phenyl rings in molecules A and B adopt different conformations in the crystal when viewed down the C_sp3—C_I vector (C0—I2, C0A—I2A); see Table 1 for torsion angles.

Inversion-related molecules A are connected via an I2···π interaction (3.641 Å to the midpoint of the C24—C23 bond) to form an A—A dimer. The halogen···π interaction has emerged as a persistent synthon in tri- and tetrahaloaryl inclusion host structures (Jetti et al., 2001; Rahman et al., 2002, 2003).

The I···π A—A dimers in (I) are connected to symmetry-independent molecules B via an I2A···I3 interaction [I2A···I3 3.5571 (15) Å, C4A—I2A···I3 166.21 (20)° and C5—I3···I2A 90.95 (17)°] and an I3···π interaction (3.561 Å to the midpoint of the C10A—C11A bond) (Fig. 2), such that atom I3 acts as both an acceptor and a donor group.

We note that the I···π interaction is shorter to the C—C bond midpoint than to the phenyl ring centroid. Further, the approach geometry is such that the polar δ+ region along the C—X bond points towards the δ- π cloud of the phenyl ring (Jetti et al., 2001). This is identical to the polarization-induced type II halogen···halogen geometry discussed by Bosch & Barnes (2002) and Jetti Thallapally et al., 2000). Thus, I···π and I···I type II interactions exhibit a similar approach geometry because both these interactions are electrostatic in nature.

Inversion-related B molecules in (I) do not have any significant close contacts between them.

We are currently carrying out a statistical study of halogen···π interactions in the Cambridge Structural Database to analyse the approach of the halogen atom to the C—C bond midpoint or the phenyl ring centroid. One brief conclusion is that the heavier halogens (Br or I) prefer the bond-midpoint approach, in agreement with our observations in (I).

The triphenylmethyl groups in (I) engage in intermolecular edge-to-face and vertex-to-face herringbone T motifs (Jetti Xue et al., 2000) through C—H···π interactions in the range 2.78–2.85 Å.

S2. Experimental

Triphenyl(3,4,5-triiodophenyl)methane, (I), was obtained as a by-product in the preparation of the aryl iodide (IV) (Jetti Xue et al., 2000) from the aryl amine (II) by diazotization and iodination (see scheme). While the exact mechanism for iodination at the meta-phenyl positions is not clear, we believe that the initially formed para-iodophenyl compound, (IV), undergoes electrophilic substitution with I₂ (formed by the oxidation of KI with NaNO₂) during the heating phase of the reaction, to afford the triiodo compound, (I). 4-(Triphenylmethyl)aniline, (II) (3.0 g, 9 mmol), was dissolved in concentrated HCl (9 ml) and H₂O (9 ml), and the mixture was cooled in ice. NaNO₂ (2.5 g, 36 mmol) was dissolved in H₂O (9 ml) and cooled to 273 K. This NaNO₂ solution was then added in small portions to the cooled anilinium-HCl solution and shaken well. A solution of KI (5.5 g, 33 mmol) in water (6 ml) was slowly added to the diazonium salt solution. The mixture was allowed to stand for a few hours at room temperature and then heated in a boiling water bath until gas evolution ceased (ca 15 h). The reaction mixture was cooled to room temperature and neutralized with 10% aqueous NaOH. The precipitated solid was filtered and the major compound was characterized as (4-iodophenyl)triphenylmethane, (IV) (m.p. 505 K). The minor component of the reaction product, (I), was separated by column chromatography (m.p. 483 K).

S3. Refinement

H atoms were included using a riding model, with a fixed C—H distance of 0.94 Å and with U_iso(H) = 1.2U_eq(C). Please check added text. It was not possible to obtain better quality crystals and thus better R values and a more appropriate weighting scheme. The residual electron density is less than 1 e Å⁻³ at distances of more than 1 Å from the I-atom positions.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. A view of the two symmetry-independent molecules, A and B, in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level and H atoms are shown as small spheres of arbitrary radii. Molecules A and B have different conformations in terms of their rotation about the C0—C1 (C0A—C1A) bond.

Fig. 2. A packing diagram for (I), showing the I···π interaction between inversion-related molecules (A—A) in the halogen···π dimer synthon. The A—A dimers are connected through an inversion-related pair of B molecules via I···π and I···I (type II) interactions (A—B). H atoms bonded to C have been omitted for clarity. Covalent bonds in A and B molecules are shaded differently. Intermolecular interactions are given in Å.

Triphenyl(3,4,5-triiodophenyl)methane

Crystal data

C25H17I3	Z = 4
Mr = 698.09	F(000) = 1304
Triclinic, P1	Dx = 2.076 Mg m^−3
Hall symbol: -P 1	Melting point: 483 K
a = 11.567 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.833 (4) Å	Cell parameters from 6227 reflections
c = 17.572 (6) Å	θ = 2.5–28.2°
α = 108.031 (6)°	µ = 4.21 mm^−1
β = 95.774 (6)°	T = 203 K
γ = 111.805 (6)°	Plate, colourless
V = 2233.0 (13) Å^3	0.56 × 0.32 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer	10771 independent reflections
Radiation source: fine-focus sealed tube	8116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.192 pixels mm^-1	θmax = 28.4°, θmin = 1.8°
ω scans	h = −15→15
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995)	k = −17→17
Tmin = 0.212, Tmax = 0.450	l = −23→22
27474 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1061P)^2 + 8.9076P] where P = (Fo^2 + 2Fc^2)/3
10771 reflections	(Δ/σ)max = 0.001
505 parameters	Δρmax = 3.74 e Å^−3
0 restraints	Δρmin = −2.97 e Å^−3

Special details

Experimental. Omega scan data collection with omega at 0.3 ° scan width, two runs with 740 frames, phi = 0, 270(°) and two runs with 436 frames, phi = 88, 180(°)

Bruker SADABS program multi-scan V2.03 (Blessing, 1995)

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.67441 (4)	0.65232 (4)	0.87897 (3)	0.04441 (15)
I2	0.81378 (5)	0.95854 (5)	0.88622 (4)	0.04732 (15)
I3	1.15151 (4)	1.08391 (4)	0.88198 (3)	0.04028 (14)
C0	1.1517 (5)	0.6519 (5)	0.8588 (4)	0.0245 (11)
C1	1.0656 (6)	0.7194 (5)	0.8657 (4)	0.0244 (11)
C2	0.9369 (6)	0.6707 (5)	0.8691 (4)	0.0270 (12)
H2A	0.8977	0.5911	0.8674	0.032*
C3	0.8666 (6)	0.7386 (6)	0.8748 (4)	0.0292 (12)
C4	0.9190 (6)	0.8575 (6)	0.8771 (4)	0.0281 (12)
C5	1.0500 (6)	0.9061 (5)	0.8755 (4)	0.0268 (12)
C6	1.1191 (6)	0.8380 (6)	0.8685 (4)	0.0274 (12)
H6A	1.2050	0.8723	0.8656	0.033*
C7	1.1804 (6)	0.6215 (5)	0.7724 (4)	0.0303 (13)
C8	1.2591 (8)	0.5631 (7)	0.7548 (5)	0.0434 (17)
H8A	1.2994	0.5476	0.7965	0.052*
C9	1.2793 (10)	0.5270 (8)	0.6762 (5)	0.054 (2)
H9A	1.3316	0.4857	0.6652	0.065*
C10	1.2253 (11)	0.5499 (8)	0.6146 (6)	0.065 (3)
H10A	1.2425	0.5279	0.5622	0.078*
C11	1.1445 (9)	0.6062 (8)	0.6311 (5)	0.049 (2)
H11A	1.1047	0.6207	0.5886	0.059*
C12	1.1204 (7)	0.6424 (7)	0.7090 (4)	0.0405 (16)
H12A	1.0647	0.6801	0.7188	0.049*
C13	1.0852 (6)	0.5254 (5)	0.8656 (4)	0.0265 (12)
C14	1.1283 (7)	0.4952 (6)	0.9287 (5)	0.0354 (14)
H14A	1.1980	0.5549	0.9726	0.043*
C15	1.0706 (7)	0.3781 (7)	0.9285 (5)	0.0388 (16)
H15A	1.1020	0.3596	0.9716	0.047*
C16	0.9683 (8)	0.2907 (7)	0.8654 (5)	0.0434 (18)
H16A	0.9299	0.2116	0.8648	0.052*
C17	0.9210 (8)	0.3184 (6)	0.8023 (5)	0.0426 (17)
H17A	0.8491	0.2587	0.7599	0.051*
C18	0.9803 (7)	0.4352 (6)	0.8015 (5)	0.0366 (14)
H18A	0.9493	0.4530	0.7578	0.044*
C19	1.2725 (6)	0.7357 (5)	0.9294 (4)	0.0258 (11)
C20	1.3978 (6)	0.7806 (6)	0.9202 (4)	0.0332 (13)
H20A	1.4125	0.7575	0.8671	0.040*
C21	1.5015 (7)	0.8591 (7)	0.9875 (5)	0.0422 (16)
H21A	1.5850	0.8888	0.9796	0.051*
C22	1.4820 (7)	0.8937 (7)	1.0669 (5)	0.0408 (16)
H22A	1.5518	0.9455	1.1129	0.049*
C23	1.3586 (7)	0.8504 (6)	1.0765 (4)	0.0372 (15)
H23A	1.3445	0.8732	1.1297	0.045*
C24	1.2552 (6)	0.7744 (6)	1.0100 (4)	0.0319 (13)
H24A	1.1718	0.7483	1.0184	0.038*
I1A	0.75055 (7)	0.70015 (6)	0.58410 (4)	0.06328 (19)
I2A	0.98721 (6)	1.00433 (7)	0.67589 (4)	0.06284 (19)
I3A	0.98113 (5)	1.21282 (5)	0.57529 (3)	0.04652 (15)
C0A	0.5474 (6)	0.8244 (5)	0.3487 (4)	0.0262 (11)
C1A	0.6603 (6)	0.8738 (6)	0.4247 (4)	0.0307 (13)
C2A	0.6681 (7)	0.7929 (7)	0.4617 (4)	0.0355 (14)
H2AA	0.6077	0.7114	0.4382	0.043*
C3A	0.7619 (8)	0.8303 (7)	0.5317 (5)	0.0402 (16)
C4A	0.8541 (7)	0.9494 (7)	0.5683 (4)	0.0398 (16)
C5A	0.8489 (6)	1.0303 (6)	0.5304 (4)	0.0332 (14)
C6A	0.7511 (6)	0.9909 (6)	0.4605 (4)	0.0308 (13)
H6AA	0.7478	1.0469	0.4372	0.037*
C7A	0.5774 (6)	0.7555 (5)	0.2706 (4)	0.0287 (12)
C8A	0.4943 (7)	0.7194 (6)	0.1931 (4)	0.0335 (13)
H8AA	0.4214	0.7354	0.1899	0.040*
C9A	0.5223 (8)	0.6596 (6)	0.1217 (5)	0.0395 (15)
H9AA	0.4655	0.6335	0.0706	0.047*
C10A	0.6269 (8)	0.6379 (6)	0.1232 (5)	0.0410 (17)
H10B	0.6429	0.5974	0.0738	0.049*
C11A	0.7131 (7)	0.6764 (6)	0.1997 (5)	0.0395 (16)
H11B	0.7884	0.6641	0.2016	0.047*
C12A	0.6852 (6)	0.7324 (6)	0.2714 (4)	0.0326 (13)
H12B	0.7408	0.7553	0.3223	0.039*
C13A	0.4292 (6)	0.7407 (6)	0.3683 (4)	0.0286 (12)
C14A	0.3556 (6)	0.6212 (6)	0.3182 (4)	0.0340 (14)
H14B	0.3734	0.5895	0.2672	0.041*
C15A	0.2550 (7)	0.5455 (7)	0.3414 (5)	0.0398 (15)
H15B	0.2074	0.4637	0.3068	0.048*
C16A	0.2259 (7)	0.5916 (7)	0.4154 (5)	0.0427 (17)
H16B	0.1569	0.5420	0.4307	0.051*
C17A	0.2988 (7)	0.7109 (7)	0.4664 (5)	0.0385 (15)
H17B	0.2802	0.7422	0.5172	0.046*
C18A	0.3994 (7)	0.7853 (6)	0.4439 (4)	0.0342 (14)
H18B	0.4482	0.8664	0.4796	0.041*
C19A	0.5257 (6)	0.9286 (6)	0.3320 (4)	0.0281 (12)
C20A	0.4177 (6)	0.9508 (6)	0.3421 (4)	0.0328 (13)
H20B	0.3552	0.9032	0.3625	0.039*
C21A	0.4006 (8)	1.0433 (7)	0.3222 (5)	0.0449 (17)
H21B	0.3261	1.0551	0.3282	0.054*
C22A	0.4904 (8)	1.1154 (7)	0.2948 (5)	0.0451 (17)
H22B	0.4799	1.1786	0.2832	0.054*
C23A	0.5993 (8)	1.0943 (7)	0.2838 (5)	0.0429 (16)
H23B	0.6613	1.1427	0.2636	0.052*
C24A	0.6161 (7)	1.0035 (6)	0.3023 (4)	0.0352 (14)
H24B	0.6902	0.9915	0.2950	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0332 (2)	0.0329 (2)	0.0582 (3)	0.01097 (19)	0.0164 (2)	0.0078 (2)
I2	0.0482 (3)	0.0437 (3)	0.0647 (4)	0.0277 (2)	0.0202 (2)	0.0272 (3)
I3	0.0386 (2)	0.0251 (2)	0.0555 (3)	0.01102 (18)	0.0050 (2)	0.0182 (2)
C0	0.027 (3)	0.020 (3)	0.025 (3)	0.009 (2)	0.007 (2)	0.007 (2)
C1	0.029 (3)	0.025 (3)	0.021 (3)	0.013 (2)	0.004 (2)	0.010 (2)
C2	0.031 (3)	0.021 (3)	0.029 (3)	0.010 (2)	0.008 (2)	0.011 (2)
C3	0.031 (3)	0.026 (3)	0.026 (3)	0.009 (2)	0.005 (2)	0.008 (2)
C4	0.030 (3)	0.028 (3)	0.025 (3)	0.014 (2)	0.001 (2)	0.009 (2)
C5	0.034 (3)	0.019 (3)	0.024 (3)	0.009 (2)	0.002 (2)	0.008 (2)
C6	0.026 (3)	0.027 (3)	0.029 (3)	0.010 (2)	0.004 (2)	0.013 (2)
C7	0.038 (3)	0.021 (3)	0.026 (3)	0.008 (2)	0.011 (2)	0.007 (2)
C8	0.064 (5)	0.035 (4)	0.035 (4)	0.025 (4)	0.023 (3)	0.009 (3)
C9	0.089 (7)	0.047 (5)	0.043 (5)	0.041 (5)	0.037 (5)	0.017 (4)
C10	0.095 (7)	0.048 (5)	0.040 (5)	0.019 (5)	0.034 (5)	0.011 (4)
C11	0.061 (5)	0.051 (5)	0.025 (3)	0.011 (4)	0.009 (3)	0.016 (3)
C12	0.039 (4)	0.035 (4)	0.033 (4)	0.004 (3)	0.008 (3)	0.009 (3)
C13	0.031 (3)	0.023 (3)	0.026 (3)	0.015 (2)	0.010 (2)	0.006 (2)
C14	0.045 (4)	0.036 (4)	0.040 (4)	0.025 (3)	0.019 (3)	0.020 (3)
C15	0.052 (4)	0.039 (4)	0.044 (4)	0.027 (3)	0.025 (3)	0.025 (3)
C16	0.056 (4)	0.031 (4)	0.059 (5)	0.025 (3)	0.034 (4)	0.023 (3)
C17	0.047 (4)	0.025 (3)	0.051 (4)	0.013 (3)	0.015 (3)	0.011 (3)
C18	0.042 (4)	0.024 (3)	0.044 (4)	0.015 (3)	0.010 (3)	0.012 (3)
C19	0.031 (3)	0.023 (3)	0.024 (3)	0.014 (2)	0.006 (2)	0.008 (2)
C20	0.034 (3)	0.039 (4)	0.029 (3)	0.015 (3)	0.012 (3)	0.015 (3)
C21	0.029 (3)	0.049 (4)	0.049 (4)	0.013 (3)	0.010 (3)	0.022 (4)
C22	0.038 (3)	0.038 (4)	0.038 (4)	0.014 (3)	−0.007 (3)	0.010 (3)
C23	0.046 (4)	0.037 (4)	0.029 (3)	0.023 (3)	0.003 (3)	0.009 (3)
C24	0.034 (3)	0.033 (3)	0.030 (3)	0.019 (3)	0.008 (3)	0.008 (3)
I1A	0.0868 (5)	0.0682 (4)	0.0534 (4)	0.0454 (4)	0.0150 (3)	0.0319 (3)
I2A	0.0518 (3)	0.0753 (4)	0.0500 (3)	0.0245 (3)	0.0005 (3)	0.0157 (3)
I3A	0.0349 (2)	0.0432 (3)	0.0455 (3)	0.0141 (2)	−0.00098 (19)	0.0026 (2)
C0A	0.026 (3)	0.026 (3)	0.024 (3)	0.011 (2)	0.004 (2)	0.007 (2)
C1A	0.034 (3)	0.035 (3)	0.024 (3)	0.017 (3)	0.008 (2)	0.009 (3)
C2A	0.038 (3)	0.037 (4)	0.034 (3)	0.020 (3)	0.007 (3)	0.012 (3)
C3A	0.051 (4)	0.049 (4)	0.033 (4)	0.031 (4)	0.012 (3)	0.019 (3)
C4A	0.034 (3)	0.060 (5)	0.031 (3)	0.029 (3)	0.007 (3)	0.012 (3)
C5A	0.026 (3)	0.040 (4)	0.025 (3)	0.014 (3)	0.002 (2)	0.003 (3)
C6A	0.031 (3)	0.033 (3)	0.025 (3)	0.015 (3)	0.005 (2)	0.005 (3)
C7A	0.034 (3)	0.023 (3)	0.027 (3)	0.012 (2)	0.007 (2)	0.008 (2)
C8A	0.038 (3)	0.033 (3)	0.029 (3)	0.017 (3)	0.008 (3)	0.009 (3)
C9A	0.051 (4)	0.030 (3)	0.030 (3)	0.012 (3)	0.009 (3)	0.008 (3)
C10A	0.063 (5)	0.030 (3)	0.036 (4)	0.023 (3)	0.027 (3)	0.011 (3)
C11A	0.048 (4)	0.030 (3)	0.049 (4)	0.022 (3)	0.026 (3)	0.014 (3)
C12A	0.038 (3)	0.035 (3)	0.034 (3)	0.022 (3)	0.013 (3)	0.015 (3)
C13A	0.028 (3)	0.030 (3)	0.027 (3)	0.012 (2)	0.006 (2)	0.010 (2)
C14A	0.034 (3)	0.033 (3)	0.028 (3)	0.011 (3)	0.006 (3)	0.008 (3)
C15A	0.037 (3)	0.034 (4)	0.042 (4)	0.008 (3)	−0.001 (3)	0.018 (3)
C16A	0.038 (4)	0.050 (4)	0.041 (4)	0.013 (3)	0.013 (3)	0.025 (4)
C17A	0.039 (3)	0.048 (4)	0.034 (4)	0.020 (3)	0.012 (3)	0.018 (3)
C18A	0.036 (3)	0.033 (3)	0.030 (3)	0.013 (3)	0.009 (3)	0.009 (3)
C19A	0.031 (3)	0.027 (3)	0.020 (3)	0.010 (2)	0.002 (2)	0.004 (2)
C20A	0.034 (3)	0.034 (3)	0.030 (3)	0.018 (3)	0.006 (2)	0.009 (3)
C21A	0.054 (4)	0.040 (4)	0.039 (4)	0.028 (4)	0.003 (3)	0.005 (3)
C22A	0.061 (5)	0.033 (4)	0.039 (4)	0.023 (4)	0.006 (3)	0.008 (3)
C23A	0.049 (4)	0.031 (4)	0.038 (4)	0.009 (3)	0.005 (3)	0.011 (3)
C24A	0.034 (3)	0.033 (3)	0.030 (3)	0.011 (3)	0.007 (3)	0.006 (3)

Geometric parameters (Å, º)

I1—C3	2.104 (6)	I1A—C3A	2.114 (7)
I2—C4	2.066 (6)	I2A—C4A	2.055 (7)
I3—C5	2.103 (6)	I3A—C5A	2.097 (7)
C0—C19	1.536 (9)	C0A—C7A	1.537 (8)
C0—C1	1.535 (8)	C0A—C13A	1.541 (8)
C0—C7	1.548 (8)	C0A—C1A	1.550 (9)
C0—C13	1.567 (8)	C0A—C19A	1.554 (9)
C1—C6	1.396 (8)	C1A—C6A	1.366 (9)
C1—C2	1.400 (8)	C1A—C2A	1.409 (10)
C2—C3	1.385 (9)	C2A—C3A	1.378 (10)
C2—H2A	0.9400	C2A—H2AA	0.9400
C3—C4	1.402 (9)	C3A—C4A	1.389 (12)
C4—C5	1.416 (9)	C4A—C5A	1.411 (11)
C5—C6	1.375 (9)	C5A—C6A	1.399 (9)
C6—H6A	0.9400	C6A—H6AA	0.9400
C7—C8	1.380 (10)	C7A—C12A	1.384 (9)
C7—C12	1.399 (11)	C7A—C8A	1.416 (9)
C8—C9	1.388 (10)	C8A—C9A	1.392 (10)
C8—H8A	0.9400	C8A—H8AA	0.9400
C9—C10	1.357 (15)	C9A—C10A	1.338 (11)
C9—H9A	0.9400	C9A—H9AA	0.9400
C10—C11	1.381 (15)	C10A—C11A	1.414 (12)
C10—H10A	0.9400	C10A—H10B	0.9400
C11—C12	1.396 (10)	C11A—C12A	1.378 (9)
C11—H11A	0.9400	C11A—H11B	0.9400
C12—H12A	0.9400	C12A—H12B	0.9400
C13—C14	1.387 (10)	C13A—C14A	1.376 (9)
C13—C18	1.398 (10)	C13A—C18A	1.407 (9)
C14—C15	1.398 (9)	C14A—C15A	1.402 (10)
C14—H14A	0.9400	C14A—H14B	0.9400
C15—C16	1.367 (12)	C15A—C16A	1.384 (11)
C15—H15A	0.9400	C15A—H15B	0.9400
C16—C17	1.386 (12)	C16A—C17A	1.378 (11)
C16—H16A	0.9400	C16A—H16B	0.9400
C17—C18	1.403 (9)	C17A—C18A	1.387 (10)
C17—H17A	0.9400	C17A—H17B	0.9400
C18—H18A	0.9400	C18A—H18B	0.9400
C19—C20	1.394 (9)	C19A—C20A	1.397 (9)
C19—C24	1.409 (9)	C19A—C24A	1.401 (9)
C20—C21	1.391 (11)	C20A—C21A	1.410 (10)
C20—H20A	0.9400	C20A—H20B	0.9400
C21—C22	1.396 (11)	C21A—C22A	1.352 (12)
C21—H21A	0.9400	C21A—H21B	0.9400
C22—C23	1.376 (11)	C22A—C23A	1.402 (12)
C22—H22A	0.9400	C22A—H22B	0.9400
C23—C24	1.376 (10)	C23A—C24A	1.376 (11)
C23—H23A	0.9400	C23A—H23B	0.9400
C24—H24A	0.9400	C24A—H24B	0.9400
I2A···I3	3.5571 (15)	C23^ii···I2	3.649 (8)
C10A^i···I3	3.574 (8)
C4A—I2A—I3	166.2 (2)	C19—C24—H24A	119.5
C5—I3—I2A	90.95 (17)	C7A—C0A—C13A	111.6 (5)
C19—C0—C1	105.4 (5)	C7A—C0A—C1A	110.3 (5)
C19—C0—C7	113.4 (5)	C13A—C0A—C1A	105.7 (5)
C1—C0—C7	110.7 (5)	C7A—C0A—C19A	106.0 (5)
C19—C0—C13	110.9 (5)	C13A—C0A—C19A	111.8 (5)
C1—C0—C13	112.7 (5)	C1A—C0A—C19A	111.6 (5)
C7—C0—C13	104.0 (5)	C6A—C1A—C2A	117.1 (6)
C6—C1—C2	117.4 (5)	C6A—C1A—C0A	125.1 (6)
C6—C1—C0	117.8 (5)	C2A—C1A—C0A	117.7 (6)
C2—C1—C0	124.8 (5)	C3A—C2A—C1A	121.6 (7)
C3—C2—C1	120.6 (5)	C3A—C2A—H2AA	119.2
C3—C2—H2A	119.7	C1A—C2A—H2AA	119.2
C1—C2—H2A	119.7	C2A—C3A—C4A	121.4 (7)
C2—C3—C4	122.6 (6)	C2A—C3A—I1A	116.5 (6)
C2—C3—I1	116.0 (4)	C4A—C3A—I1A	122.0 (5)
C4—C3—I1	121.4 (5)	C3A—C4A—C5A	117.3 (6)
C3—C4—C5	116.0 (6)	C3A—C4A—I2A	120.4 (6)
C3—C4—I2	122.3 (5)	C5A—C4A—I2A	122.2 (6)
C5—C4—I2	121.7 (4)	C6A—C5A—C4A	120.3 (6)
C6—C5—C4	121.4 (5)	C6A—C5A—I3A	116.7 (5)
C6—C5—I3	115.5 (4)	C4A—C5A—I3A	123.0 (5)
C4—C5—I3	123.1 (4)	C1A—C6A—C5A	122.2 (6)
C5—C6—C1	122.0 (6)	C1A—C6A—H6AA	118.8
C5—C6—H6A	119.0	C5A—C6A—H6AA	118.9
C1—C6—H6A	119.0	C12A—C7A—C8A	118.0 (6)
C8—C7—C12	118.6 (6)	C12A—C7A—C0A	123.5 (6)
C8—C7—C0	119.3 (6)	C8A—C7A—C0A	118.4 (6)
C12—C7—C0	121.9 (6)	C9A—C8A—C7A	118.9 (7)
C7—C8—C9	120.7 (8)	C9A—C8A—H8AA	120.5
C7—C8—H8A	119.7	C7A—C8A—H8AA	120.5
C9—C8—H8A	119.6	C10A—C9A—C8A	122.5 (7)
C10—C9—C8	121.6 (9)	C10A—C9A—H9AA	118.8
C10—C9—H9A	119.1	C8A—C9A—H9AA	118.7
C8—C9—H9A	119.2	C9A—C10A—C11A	119.5 (6)
C9—C10—C11	118.1 (8)	C9A—C10A—H10B	120.3
C9—C10—H10A	120.9	C11A—C10A—H10B	120.3
C11—C10—H10A	120.9	C12A—C11A—C10A	119.0 (7)
C10—C11—C12	121.8 (8)	C12A—C11A—H11B	120.6
C10—C11—H11A	119.1	C10A—C11A—H11B	120.5
C12—C11—H11A	119.1	C11A—C12A—C7A	122.0 (7)
C11—C12—C7	119.1 (8)	C11A—C12A—H12B	119.0
C11—C12—H12A	120.5	C7A—C12A—H12B	119.0
C7—C12—H12A	120.5	C14A—C13A—C18A	117.6 (6)
C14—C13—C18	118.1 (6)	C14A—C13A—C0A	123.5 (6)
C14—C13—C0	124.2 (6)	C18A—C13A—C0A	118.7 (6)
C18—C13—C0	117.7 (6)	C13A—C14A—C15A	121.6 (6)
C13—C14—C15	121.6 (7)	C13A—C14A—H14B	119.2
C13—C14—H14A	119.2	C15A—C14A—H14B	119.2
C15—C14—H14A	119.2	C16A—C15A—C14A	119.8 (7)
C16—C15—C14	119.8 (7)	C16A—C15A—H15B	120.1
C16—C15—H15A	120.1	C14A—C15A—H15B	120.1
C14—C15—H15A	120.1	C17A—C16A—C15A	119.3 (7)
C15—C16—C17	120.1 (7)	C17A—C16A—H16B	120.3
C15—C16—H16A	120.0	C15A—C16A—H16B	120.3
C17—C16—H16A	120.0	C16A—C17A—C18A	120.8 (7)
C16—C17—C18	120.3 (7)	C16A—C17A—H17B	119.6
C16—C17—H17A	119.9	C18A—C17A—H17B	119.6
C18—C17—H17A	119.9	C17A—C18A—C13A	120.8 (6)
C13—C18—C17	120.2 (7)	C17A—C18A—H18B	119.6
C13—C18—H18A	119.9	C13A—C18A—H18B	119.6
C17—C18—H18A	119.9	C20A—C19A—C24A	116.8 (6)
C20—C19—C24	117.1 (6)	C20A—C19A—C0A	123.9 (6)
C20—C19—C0	125.4 (5)	C24A—C19A—C0A	119.3 (6)
C24—C19—C0	117.5 (5)	C19A—C20A—C21A	121.2 (7)
C21—C20—C19	121.5 (6)	C19A—C20A—H20B	119.4
C21—C20—H20A	119.2	C21A—C20A—H20B	119.4
C19—C20—H20A	119.2	C22A—C21A—C20A	120.8 (7)
C20—C21—C22	120.2 (6)	C22A—C21A—H21B	119.6
C20—C21—H21A	119.9	C20A—C21A—H21B	119.6
C22—C21—H21A	119.9	C21A—C22A—C23A	119.0 (7)
C23—C22—C21	118.6 (7)	C21A—C22A—H22B	120.5
C23—C22—H22A	120.7	C23A—C22A—H22B	120.5
C21—C22—H22A	120.7	C24A—C23A—C22A	120.6 (7)
C22—C23—C24	121.6 (7)	C24A—C23A—H23B	119.6
C22—C23—H23A	119.2	C22A—C23A—H23B	119.7
C24—C23—H23A	119.2	C23A—C24A—C19A	121.6 (7)
C23—C24—C19	121.0 (6)	C23A—C24A—H24B	119.2
C23—C24—H24A	119.5	C19A—C24A—H24B	119.1
C2—C1—C0—C7	109.6 (7)	C2A—C1A—C0A—C7A	−80.5 (8)
C2—C1—C0—C19	−127.5 (7)	C2A—C1A—C0A—C19A	162.0 (6)
C2—C1—C0—C13	−6.3 (9)	C2A—C1A—C0A—C13A	40.3 (8)
C6—C1—C0—C19	52.8 (7)	C6A—C1A—C0A—C19A	−15.9 (10)
C6—C1—C0—C13	174.0 (6)	C6A—C1A—C0A—C13A	−137.6 (7)
C6—C1—C0—C7	−70.1 (7)	C6A—C1A—C0A—C7A	101.6 (8)

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