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In the crystal structure of the title compound, 2C22H24P+·I82-, the I82- anion is located on a crystallographic inversion centre and consists of two tri-iodide anions linked by di-iodine at angles of 89.92 (4)° to form a planar `Z'-shaped dianion. The octa­iodides are linked via long-range inter­actions [3.877 (11) Å] into infinite polyiodide ribbons. This is the first example of a structure containing an [(o-tol­yl)3PMe]+ cation, and the CMe-P-C-CMe torsion angles of -54.0 (11), -51.3 (11) and -48.2 (11)° indicate that the configuration is exo3.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111019287/fa3253sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111019287/fa3253Isup2.hkl
Contains datablock I

CCDC reference: 838149

Comment top

The octaiodide anion is a member of the dianionic polyiodide series I2n+22-, whose first three members would be expected to consist of a di-iodine combined, respectively, with two iodide anions, an iodide and tri-iodide and two tri-iodide anions. The tetra-iodide is the most frequently encountered polyiodide in the I2n+22- series and in all cases the I42- anion is linear. No intermolecular I···I contacts less than 4 Å have been observed in these compounds (Kloo & Svensson, 2003). To date no structure containing an undisordered I62- has been reported. It is therefore somewhat surprising that several I82--containing structures are known. The first I82- ion was determined by Havinga et al. (1954) in Cs2I8. Generally an I82- ion consists of two I3- ions that interact with an I2 molecule to form `Z'-shaped [(I3-)2.(I2)]. This geometry, which includes out-stretched (`S'-shaped) or slightly deformed forms, is the predominating geometry for all structurally characterized octaiodide ions.

In the title structure, {2[(o-tolyl)3PMe]+ + I82-}, the I82- has a `Z' shape (Fig. 1). The bonding distances in the octaiodide indicate that it is made up of two tri-iodide anions and a di-iodine molecule (Table 1). Although the `Z' angle is 81° in the inorganic Cs2I8, the `Z' angle of 89.92 (4)° in the current structure is the most acute seen in structures containing organic cations. In the title molecule the I82- `Z' is completely flat with the two I3- units configured trans to one another. In other words, the torsion angle defined by the angle between the two I3- ions when projected down the I2 bond is 180°, as required by the centre of inversion that relates them. This is the configuration seen in all known I82- ions except for the tris(1,10-phenanthroline)iron(II) complex, C36H24FeN62+, I82- (-82.1°) (Horn et al., 2001) and the dihydrogen(2.2.2)cryptand, C18H38N2 O62+, I82- (-99.3°) (Grafe-Kavoosian et al., 1998). It is interesting that the central torsion angle is either 180° or close to 90°.

Each I82- anion in the present structure associates with two adjacent anions via long contacts of 3.977 (1) Å to form infinite polyiodide ribbons along [100] (Fig. 2). Interestingly this is the first example where the long-range interactions between I82- ions involve both the I3- and I2 moieties. In all other cases, where interionic interactions occur between I82- units, only the I3- ions are involved. When only one iodine in each I3- ion takes part in long-range interactions, a helical (Horn et al., 2001) or branched (Kuhn et al., 2000) chain is produced. When both terminal I3- iodine atoms are employed, puckered sheets result (Grafe-Kavoosian et al., 1998; Kuz'mina et al., 2000). Although the number of long-range I···I interactions are the same in the title structure as they are in the puckered sheets, involvement of the central I2 gives lower conformational freedom, leading to flat ribbons.

The CMe—P—C—CMe torsion angle values of C22—P1—C1—C2, -54.0 (11)°, C22—P1—C8—C9, -51.3 (11)°, and C22—P1—C15—C16, -48.2 (11)° confirm that the configuration is exo3, which is as expected for a tri-o-tolylphosphine moiety with a small apical substituent cf. (o-tolyl)3PO, which is also exo3 and whose corresponding torsion angles fall in the range 33.8 to 52.4° with an average value of 45.9°. See Howell et al. (1992) for a previous example of the exo notation being used in tris(ortho-tolyl) derivatives of P, As and Si. The larger torsion angles in the title cation reflect the slightly larger size of CH3 relative to O and must be at the upper limit for the exo3 configuration. The increased size of the apical substituent in (o-tolyl)3PS flips the structure to an exo2 configuration even though, according to Pauling, CH3 has a larger Van der Waals' radius than S. This is because H atoms of the ortho-CH3 groups nestle between the H atoms of the apical CH3, effectively reducing the Van der Waals' radius of the methyl group.

Related literature top

For related literature, see: Kuz'mina Palkina Savinkina Kozlova Kuznetsov (2000); Grafe-Kavoosian et al. (1998); Havinga et al. (1954); Horn et al. (2001); Howell et al. (1992); Kloo & Svensson (2003); Kuhn et al. (2000).

Experimental top

Equimolar quantities of methyliodide and tri-o-tolylphosphine were reacted in dry dichloromethane at room temperature. The containers were stoppered but further precautions to protect the sample from the atmosphere were deemed unnecessary. Anhydrous dichloromethane (25 ml) was added to a dry Rotaflo tube. To this solution was added (o-CH3C6H4)3P (1.005 g, 3.30 mmol) which rapidly dissolved. Iodomethane (0.60 ml, 9.91 mol) was added slowly over a period of several minutes. After 5 min a white solid gradually formed and the reaction was left to stir for a further 24 h. The solid was then isolated using standard Schlenk techniques and dried in vacuo for 2 h to yield 1.394 g of a solid (94.6% yield). Analysis calculated for C22H24PI4: C 59.2, H 5.4, I 28.5%; found: C 59.1, H 5.3, I 28.1%. For recrystallization, the compound was dissolved in CH2Cl2. Iodine was added to the solution, [which was] dissolved in dichloromethane in a 2:1 molar ratio. The solution was allowed to stand for 4 d to allow dark-red crystals to form by slow evaporation: 2[(o-tolyl)3PCH3]+ + 2I- + 3I2 2[(o-tolyl)3PCH3]++ I8-2.

Refinement top

H atoms were constrained to chemically reasonable positions, with C—H bond lengths set at 0.95 Å for phenyl and at 0.98 Å for methyl groups. Uiso(H) values were set at 1.2 times the Ueq values of the attached C atoms in phenyl rings and at 1.5 times the Ueq value for methyl H atoms. The largest peaks remaining in the difference map have electron densities of 4.7 and 3.6 e Å-3. They are arranged linearly on either side of I4 at distances of 2.924 and 2.964 Å, forming an I3- shape. No credible twin model was found, and no indication of spot splitting could be seen in the X-ray images. It was therefore concluded that the best explanation for the residual electron density was a minor secondary phase that had intergrown with the primary structure.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. View of the methyltri-o-tolylphosphonium cation and the centrosymmetric octaiodide dianion, including the atom-labelling scheme. [Symmetry code: (i) -x + 1, -y, -z + 1.]
[Figure 2] Fig. 2. The octaiodide anions linked into a polyiodide ribbon viewed down the crystallographic b axis.
Bis(methyltri-o-tolylphosphonium) octaiodide top
Crystal data top
2C22H24P+·I82Z = 1
Mr = 1653.96F(000) = 766
Triclinic, P1Dx = 2.131 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6680 (2) ÅCell parameters from 5850 reflections
b = 12.3567 (3) Åθ = 1.0–27.5°
c = 12.8186 (4) ŵ = 4.90 mm1
α = 62.364 (1)°T = 100 K
β = 76.410 (1)°Prism, colourless
γ = 73.073 (1)°0.15 × 0.1 × 0.1 mm
V = 1288.83 (6) Å3
Data collection top
Nonius KappaCCD
diffractometer
4776 independent reflections
Radiation source: Enraf–Nonius FR5903762 reflections with I > 2σ(I)
Graphite monochromatorRint = 0
Detector resolution: 9 pixels mm-1θmax = 25.5°, θmin = 3.1°
CCD rotation images, thick slices scansh = 011
Absorption correction: multi-scan
(Blessing, 1995)
k = 1314
Tmin = 0.527, Tmax = 0.640l = 1415
4776 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0697P)2 + 33.6613P]
where P = (Fo2 + 2Fc2)/3
4776 reflections(Δ/σ)max = 0.01
247 parametersΔρmax = 4.65 e Å3
0 restraintsΔρmin = 2.84 e Å3
Crystal data top
2C22H24P+·I82γ = 73.073 (1)°
Mr = 1653.96V = 1288.83 (6) Å3
Triclinic, P1Z = 1
a = 9.6680 (2) ÅMo Kα radiation
b = 12.3567 (3) ŵ = 4.90 mm1
c = 12.8186 (4) ÅT = 100 K
α = 62.364 (1)°0.15 × 0.1 × 0.1 mm
β = 76.410 (1)°
Data collection top
Nonius KappaCCD
diffractometer
4776 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
3762 reflections with I > 2σ(I)
Tmin = 0.527, Tmax = 0.640Rint = 0
4776 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.183H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0697P)2 + 33.6613P]
where P = (Fo2 + 2Fc2)/3
4776 reflectionsΔρmax = 4.65 e Å3
247 parametersΔρmin = 2.84 e Å3
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Highest peak 4.65 at 0.8008 0.0396 0.3150 [1.58 A from I3] Deepest hole -2.84 at 0.8106 0.0962 0.2631 [0.88 A from I3]

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0514 (13)0.6483 (10)0.2440 (10)0.027 (2)
C20.1762 (12)0.7405 (11)0.2010 (10)0.028 (2)
C30.2969 (14)0.7014 (12)0.1980 (11)0.036 (3)
H30.38180.76230.1690.043*
C40.2957 (15)0.5768 (13)0.2360 (11)0.038 (3)
H40.37920.55210.23440.046*
C50.1704 (16)0.4878 (13)0.2770 (13)0.043 (3)
H50.16770.40220.30080.052*
C60.0494 (14)0.5222 (11)0.2836 (11)0.031 (3)
H60.03390.46030.31480.038*
C70.1839 (15)0.8778 (11)0.1541 (13)0.040 (3)
H7A0.13760.90920.07190.059*
H7B0.13310.89210.20280.059*
H7C0.2860.92170.15690.059*
C80.0676 (12)0.7516 (10)0.3600 (10)0.026 (2)
C90.1674 (12)0.8064 (10)0.3740 (10)0.028 (2)
C100.1244 (14)0.8526 (11)0.4603 (11)0.034 (3)
H100.18930.88960.47210.041*
C110.0093 (15)0.8463 (12)0.5290 (11)0.039 (3)
H110.03490.87960.58620.046*
C120.1059 (13)0.7920 (11)0.5153 (11)0.032 (3)
H120.19780.78780.56230.038*
C130.0660 (13)0.7431 (11)0.4308 (11)0.031 (3)
H130.13050.70370.42160.038*
C140.3155 (13)0.8166 (12)0.3027 (12)0.034 (3)
H14A0.35660.74250.2870.05*
H14B0.38010.82250.34760.05*
H14C0.30580.89150.22740.05*
C150.2541 (13)0.5491 (10)0.2975 (11)0.031 (3)
C160.3251 (14)0.4933 (11)0.2217 (11)0.033 (3)
C170.4397 (14)0.3890 (11)0.2652 (12)0.035 (3)
H170.49210.34860.21580.042*
C180.4783 (14)0.3438 (10)0.3781 (11)0.032 (3)
H180.55680.2740.40430.038*
C190.4037 (14)0.3992 (12)0.4519 (12)0.040 (3)
H190.42850.36690.52990.048*
C200.2936 (13)0.5011 (11)0.4123 (11)0.031 (2)
H200.24250.54030.4630.037*
C210.2909 (15)0.5379 (12)0.0958 (12)0.039 (3)
H21A0.18630.57260.0920.058*
H21B0.31920.46720.07440.058*
H21C0.34520.60250.04030.058*
C220.1675 (14)0.8032 (11)0.1074 (11)0.036 (3)
H22A0.18920.76820.04920.054*
H22B0.25510.82490.11170.054*
H22C0.08970.87840.08320.054*
I10.46014 (8)0.16783 (8)0.08788 (7)0.0357 (2)
I20.13654 (8)0.17991 (7)0.14356 (7)0.0318 (2)
I30.16302 (9)0.16748 (8)0.21429 (7)0.0362 (2)
I40.49111 (8)0.03495 (7)0.38206 (8)0.0345 (2)
P10.1093 (3)0.6890 (3)0.2512 (3)0.0257 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.032 (6)0.025 (6)0.024 (5)0.001 (5)0.009 (5)0.009 (5)
C20.026 (6)0.030 (6)0.033 (6)0.004 (5)0.003 (5)0.017 (5)
C30.032 (6)0.043 (7)0.034 (7)0.005 (5)0.000 (5)0.020 (6)
C40.041 (7)0.047 (8)0.030 (6)0.023 (6)0.003 (5)0.012 (6)
C50.049 (8)0.035 (7)0.048 (8)0.017 (6)0.009 (6)0.015 (6)
C60.036 (7)0.031 (6)0.033 (6)0.009 (5)0.000 (5)0.020 (5)
C70.043 (7)0.026 (6)0.050 (8)0.008 (5)0.019 (6)0.019 (6)
C80.030 (6)0.016 (5)0.032 (6)0.007 (4)0.002 (5)0.011 (4)
C90.028 (6)0.020 (5)0.032 (6)0.000 (4)0.007 (5)0.009 (5)
C100.041 (7)0.027 (6)0.033 (6)0.001 (5)0.015 (5)0.012 (5)
C110.044 (7)0.036 (7)0.033 (7)0.004 (6)0.006 (6)0.019 (6)
C120.031 (6)0.034 (6)0.028 (6)0.001 (5)0.006 (5)0.015 (5)
C130.034 (6)0.025 (6)0.034 (6)0.002 (5)0.012 (5)0.010 (5)
C140.032 (6)0.031 (6)0.042 (7)0.012 (5)0.000 (5)0.019 (5)
C150.036 (6)0.021 (5)0.040 (7)0.004 (5)0.009 (5)0.016 (5)
C160.036 (7)0.027 (6)0.038 (7)0.008 (5)0.012 (5)0.012 (5)
C170.037 (7)0.031 (6)0.040 (7)0.000 (5)0.004 (5)0.022 (6)
C180.038 (7)0.012 (5)0.043 (7)0.000 (4)0.012 (5)0.010 (5)
C190.034 (7)0.037 (7)0.043 (7)0.006 (5)0.020 (6)0.006 (6)
C200.033 (6)0.026 (6)0.035 (6)0.003 (5)0.004 (5)0.016 (5)
C210.041 (7)0.038 (7)0.040 (7)0.001 (6)0.008 (6)0.023 (6)
C220.041 (7)0.023 (6)0.038 (7)0.001 (5)0.006 (6)0.010 (5)
I10.0289 (4)0.0428 (5)0.0347 (4)0.0060 (3)0.0035 (3)0.0169 (4)
I20.0331 (4)0.0318 (4)0.0314 (4)0.0057 (3)0.0033 (3)0.0152 (3)
I30.0306 (4)0.0453 (5)0.0397 (5)0.0087 (3)0.0041 (3)0.0234 (4)
I40.0307 (4)0.0330 (4)0.0461 (5)0.0078 (3)0.0020 (3)0.0225 (4)
P10.0276 (15)0.0216 (13)0.0294 (15)0.0054 (11)0.0035 (12)0.0118 (12)
Geometric parameters (Å, º) top
C1—C61.394 (16)C13—H130.95
C1—C21.410 (16)C14—H14A0.98
C1—P11.800 (12)C14—H14B0.98
C2—C31.402 (17)C14—H14C0.98
C2—C71.499 (17)C15—C161.387 (18)
C3—C41.379 (19)C15—C201.409 (17)
C3—H30.95C15—P11.825 (12)
C4—C51.39 (2)C16—C171.411 (17)
C4—H40.95C16—C211.529 (17)
C5—C61.387 (18)C17—C181.387 (18)
C5—H50.95C17—H170.95
C6—H60.95C18—C191.371 (19)
C7—H7A0.98C18—H180.95
C7—H7B0.98C19—C201.363 (17)
C7—H7C0.98C19—H190.95
C8—C131.394 (17)C20—H200.95
C8—C91.413 (16)C21—H21A0.98
C8—P11.806 (11)C21—H21B0.98
C9—C101.397 (17)C21—H21C0.98
C9—C141.511 (17)C22—P11.808 (13)
C10—C111.383 (19)C22—H22A0.98
C10—H100.95C22—H22B0.98
C11—C121.380 (18)C22—H22C0.98
C11—H110.95I1—I23.0162 (11)
C12—C131.401 (17)I2—I32.8511 (11)
C12—H120.95I4—I4i2.7663 (17)
C6—C1—C2120.7 (11)C9—C14—H14B109.5
C6—C1—P1117.9 (9)H14A—C14—H14B109.5
C2—C1—P1121.4 (9)C9—C14—H14C109.5
C3—C2—C1118.0 (11)H14A—C14—H14C109.5
C3—C2—C7118.6 (11)H14B—C14—H14C109.5
C1—C2—C7123.3 (11)C16—C15—C20121.0 (11)
C4—C3—C2121.7 (12)C16—C15—P1121.3 (9)
C4—C3—H3119.1C20—C15—P1117.6 (9)
C2—C3—H3119.1C15—C16—C17116.3 (11)
C3—C4—C5119.0 (12)C15—C16—C21125.1 (11)
C3—C4—H4120.5C17—C16—C21118.6 (11)
C5—C4—H4120.5C18—C17—C16122.0 (11)
C6—C5—C4121.1 (12)C18—C17—H17119
C6—C5—H5119.4C16—C17—H17119
C4—C5—H5119.4C19—C18—C17120.4 (11)
C5—C6—C1119.3 (12)C19—C18—H18119.8
C5—C6—H6120.3C17—C18—H18119.8
C1—C6—H6120.3C20—C19—C18119.3 (12)
C2—C7—H7A109.5C20—C19—H19120.4
C2—C7—H7B109.5C18—C19—H19120.4
H7A—C7—H7B109.5C19—C20—C15121.1 (12)
C2—C7—H7C109.5C19—C20—H20119.5
H7A—C7—H7C109.5C15—C20—H20119.5
H7B—C7—H7C109.5C16—C21—H21A109.5
C13—C8—C9120.9 (10)C16—C21—H21B109.5
C13—C8—P1117.8 (8)H21A—C21—H21B109.5
C9—C8—P1121.3 (9)C16—C21—H21C109.5
C10—C9—C8116.8 (11)H21A—C21—H21C109.5
C10—C9—C14119.1 (11)H21B—C21—H21C109.5
C8—C9—C14124.1 (10)P1—C22—H22A109.5
C11—C10—C9122.4 (12)P1—C22—H22B109.5
C11—C10—H10118.8H22A—C22—H22B109.5
C9—C10—H10118.8P1—C22—H22C109.5
C12—C11—C10120.5 (12)H22A—C22—H22C109.5
C12—C11—H11119.7H22B—C22—H22C109.5
C10—C11—H11119.7I3—I2—I1174.42 (4)
C11—C12—C13118.9 (12)C1—P1—C22109.8 (6)
C11—C12—H12120.6C1—P1—C8108.7 (5)
C13—C12—H12120.6C22—P1—C8110.4 (5)
C8—C13—C12120.5 (11)C1—P1—C15109.4 (5)
C8—C13—H13119.7C22—P1—C15109.8 (6)
C12—C13—H13119.7C8—P1—C15108.7 (5)
C9—C14—H14A109.5
C6—C1—C2—C30.7 (17)C15—C16—C17—C180.8 (18)
P1—C1—C2—C3179.9 (9)C21—C16—C17—C18179.3 (12)
C6—C1—C2—C7178.3 (11)C16—C17—C18—C190.8 (19)
P1—C1—C2—C72.4 (17)C17—C18—C19—C201.6 (19)
C1—C2—C3—C40.2 (18)C18—C19—C20—C150.8 (19)
C7—C2—C3—C4177.9 (12)C16—C15—C20—C190.7 (18)
C2—C3—C4—C50.9 (19)P1—C15—C20—C19177.9 (10)
C3—C4—C5—C62 (2)C6—C1—P1—C22126.6 (9)
C4—C5—C6—C13 (2)C2—C1—P1—C2254.0 (11)
C2—C1—C6—C51.9 (18)C6—C1—P1—C8112.6 (10)
P1—C1—C6—C5178.7 (10)C2—C1—P1—C866.8 (11)
C13—C8—C9—C100.9 (16)C6—C1—P1—C156.0 (11)
P1—C8—C9—C10179.7 (8)C2—C1—P1—C15174.6 (10)
C13—C8—C9—C14178.6 (11)C13—C8—P1—C18.8 (10)
P1—C8—C9—C140.7 (16)C9—C8—P1—C1171.8 (9)
C8—C9—C10—C110.3 (17)C13—C8—P1—C22129.3 (9)
C14—C9—C10—C11179.9 (11)C9—C8—P1—C2251.3 (11)
C9—C10—C11—C120.7 (19)C13—C8—P1—C15110.2 (9)
C10—C11—C12—C130.2 (18)C9—C8—P1—C1569.2 (10)
C9—C8—C13—C121.8 (17)C16—C15—P1—C172.4 (11)
P1—C8—C13—C12178.8 (9)C20—C15—P1—C1108.9 (10)
C11—C12—C13—C81.4 (17)C16—C15—P1—C2248.2 (11)
C20—C15—C16—C171.5 (17)C20—C15—P1—C22130.5 (10)
P1—C15—C16—C17177.1 (9)C16—C15—P1—C8169.1 (10)
C20—C15—C16—C21180.0 (12)C20—C15—P1—C89.6 (11)
P1—C15—C16—C211.3 (17)
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula2C22H24P+·I82
Mr1653.96
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.6680 (2), 12.3567 (3), 12.8186 (4)
α, β, γ (°)62.364 (1), 76.410 (1), 73.073 (1)
V3)1288.83 (6)
Z1
Radiation typeMo Kα
µ (mm1)4.90
Crystal size (mm)0.15 × 0.1 × 0.1
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.527, 0.640
No. of measured, independent and
observed [I > 2σ(I)] reflections
4776, 4776, 3762
Rint0
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.183, 1.15
No. of reflections4776
No. of parameters247
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0697P)2 + 33.6613P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)4.65, 2.84

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top
C1—P11.800 (12)I1—I23.0162 (11)
C8—P11.806 (11)I2—I32.8511 (11)
C15—P11.825 (12)I4—I4i2.7663 (17)
C22—P11.808 (13)
I3—I2—I1174.42 (4)C1—P1—C15109.4 (5)
C1—P1—C22109.8 (6)C22—P1—C15109.8 (6)
C1—P1—C8108.7 (5)C8—P1—C15108.7 (5)
C22—P1—C8110.4 (5)
Symmetry code: (i) x+1, y, z+1.
 

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