Synthesis and crystal structures of [Ph3PCH2PPh3]I2 di­chloro­methane disolvate and [Ph3PCH2PPh3](BI4)2

Ganguly, R.; Jevtovic, V.

doi:10.1107/S2056989017010295

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Volume 73| Part 8| August 2017| Pages 1259-1263

https://doi.org/10.1107/S2056989017010295

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Synthesis and crystal structures of [Ph₃PCH₂PPh₃]I₂ dichloromethane disolvate and [Ph₃PCH₂PPh₃](BI₄)₂

Rakesh Ganguly ^a ^* and Violeta Jevtovic ^b

^aDivision of Chemistry & Biological Chemistry, SPMS-CBC-01-18D, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore, and ^bDepartment of Biological Sciences and Chemistry, College of Arts and Sciences, University of Nizwa, Sultanate of Oman
^*Correspondence e-mail: rganguly@ntu.edu.sg

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 30 May 2017; accepted 11 July 2017; online 28 July 2017)

Reaction of BI₃ with carbodiphosphorane, C(PPh₃)₂, gives a mixture of the dicationic compounds, methylenebis(triphenylphosphonium) diiodide dichloromethane disolvate, C₃₇H₃₂P₂²⁺·2I⁻·2CH₂Cl₂ or [Ph₃PCH₂PPh₃]I₂·2CH₂Cl₂ (I), methylenebis(triphenylphosphonium) bis(tetraiodoborate), C₃₇H₃₂P₂²⁺·2BI₄⁻ or [Ph₃PCH₂PPh₃](BI₄)₂ (II). Solvents are the source of the protons at the ylidic C atom. The P—C—P angle is 124.1 (2)° for (I) and 121.7 (3)° for (II), while the two P—C bond lengths are 1.804 (4) and 1.807 (5) Å in (I), and 1.817 (5) and 1.829 (5) Å in (II). In the crystal of (I), the protons of the central P—CH₂—P C atom exhibit weak C—H⋯I hydrogen bonds with the respective anions. The anions in turn are linked to the dichloromethane solvent molecules by C—H⋯I hydrogen bonds. In the crystal of (II), one of the BI₄⁻ anions is linked to a phenyl H atom via a weak C—H⋯I hydrogen bond.

Keywords: crystal structure; carbodiphosphorane; C—H⋯I hydrogen bonding.

CCDC references: 1533031; 1552112

1. Chemical context

Carbodiphosphoranes, C(PH₃)₂, have been known since the early 1960s (Ramirez et al., 1961 ), but recent theoretical and experimental investigations has revived interest in these compounds (Tay et al., 2016 ; Dordevic et al., 2016 ). Theoretical studies (Frenking & Tonner, 2009 ) show the presence of two lone pairs of electrons, σ and π, which can act both as σ- and π-donor substituents (Tay et al., 2013 ). Herein, we report on the crystal structures of two dicationic carbodiphophorane species, viz. [Ph₃PCH₂PPh₃]I₂·2CH₂Cl₂, (I), and [Ph₃PCH₂PPh₃](BI₄)₂, (II).

2. Structural commentary

Compound [Ph₃PCH₂PPh₃]I₂, (I), crystallizes as a dichloromethane disolvate (Fig. 1), whereas compound (II) is not solvated (Fig. 2). For both compounds, the C2/P1/C1/P2/C20 fragment lies in a plane, as shown in Figs. 1 and 2, respectively, with the P1—C1—P2 angle being 124.1 (2)° for (I) and 121.7 (3)° for (II); see Tables 1 and 2. Such a conformation avoids any significant steric repulsion between the phenyl groups on the adjacent P atoms. The smaller value in compound (II) is attributed to decreased steric repulsion and/or an absence of electrostatic repulsion (Walker & Poli, 1989 ). The P—C bond lengths in compound (I) are slightly shorter than those in compound (II); see Tables 1 and 2. In (II), the BI₄⁻ anions display regular tetrahedral geometry, with I—B—I angles ranging from 108.1 (3) to 110.9 (3)°.

Table 1
Selected geometric parameters (Å, °) for (I)

C1—P2	1.804 (4)	C1—P1	1.807 (5)

P1—C1—P2	124.1 (2)

Table 2
Selected geometric parameters (Å, °) for (II)

C1—P2	1.817 (5)	C1—P1	1.829 (5)

P1—C1—P2	121.7 (3)

Figure 1
The molecular structure of compound (I), showing the atom labelling and 40% probability displacement ellipsoids.

Figure 2
The molecular structure of compound (II), showing the atom labelling and 40% probability displacement ellipsoids.

3. Supramolecular features

In the crystal of (I), the iodide anion I1 forms weak hydrogen bonds with atoms H1A and H39A, while iodide anion I2 forms another pair of weak hydrogen bonds with atoms H1B and H38B, as shown in Table 3 and Fig. 3. In the crystal of (II), a single C—H⋯I hydrogen bond is observed linking an anion to the [Ph₃PCH₂PPh₃]²⁺ unit (Table 4 and Fig. 4).

Table 3
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯I1ⁱ	0.99	2.81	3.802 (4)	175
C39—H39A⋯I1ⁱ	0.99	3.05	3.986 (7)	159
C1—H1B⋯I2ⁱ	0.99	2.83	3.813 (4)	175
C38—H38B⋯I2ⁱⁱ	0.99	2.88	3.848 (6)	166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 4
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯I1ⁱ	0.95	3.02	3.730 (7)	132
Symmetry code: (i) x, y+1, z.

Figure 3
A view along the a axis of the crystal packing of compound (I). Only the H atoms (grey balls) participating in hydrogen bonding (dashed lines) have been included (see Table 3

Figure 4
A view along the a axis of the crystal packing of compound (II). Only the H atom (grey ball) participating in hydrogen bonding (dashed lines) has been included (see Table 4

4. Database survey

A search of the Cambridge Structural Database (Version 5.38, last update May 2016; Groom et al., 2016 ) revealed eight reported structures of the dicationic species, which all show similar conformations. In these eight structures, the P—C—P angle varies from ca 120.89 to 123.35°, while the P—C bond lengths vary from ca 1.802 to 1.833 Å. The smallest P—C—P angle and the shortest P—C bond length, ca 120.89° and 1.802 Å, respectively, are observed in methylenebis(triphenylphosphonium) dichloride 1,2-dimethoxyethane monosolvate (CSD refcode CADZUE; Petz et al., 2011 ). While one of the largest P—C—P angles (ca 123.11°) and longest P—C bond lengths (ca 1.825 Å) were observed for methylenebis(triphenylphosphonium) bis(tetrachloroindium) dichloromethane monosolvate (CIYGIB; Petz et al., 2008 ). Interestingly, in compound (I), the P—C bond lengths are short [1.804 (4) and 1.807 (5) Å], while the P—C—P angle [124.1 (2)°] is one of the largest observed to date.

5. Synthesis and crystallization

(Ph₃)₂C (0.1 g, 0.19 mmol) and 1 equivalent of BI₃ were mixed in ca 10 ml of DCM and left to stir overnight under inert conditions. The volume of the resulting solution was reduced to ca 3 ml and layered with ca 5 ml of hexane. A crop of crystals formed in a few days [yield 0.02 g, 4% based on (PPh₃)₂C, for (I) and 0.015 g, 5% based on (PPh₃)₂C, for (II)].

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. The H atoms were included in calculated positions and treated as riding atoms, with C—H = 0.95–0.99 Å and U_iso(H) = 1.2U_eq(C). For both compounds, a small number of reflections were affected by the beam stop and were omitted from the final cycles of refinement.

Table 5
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₃₇H₃₂P₂²⁺·2I⁻·2CH₂Cl₂	C₃₇H₃₂P₂²⁺·2BI₄⁻
M_r	962.22	1575.38
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	153	153
a, b, c (Å)	9.7510 (13), 22.914 (3), 18.204 (2)	19.7878 (6), 14.3122 (3), 16.0646 (4)
β (°)	104.629 (2)	96.230 (1)
V (Å³)	3935.5 (9)	4522.7 (2)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	1.98	5.58
Crystal size (mm)	0.14 × 0.12 × 0.06	0.14 × 0.12 × 0.08

Data collection
Diffractometer	Bruker CCD area detector	Bruker CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )	Multi-scan (SADABS; Bruker, 2015)
T_min, T_max	0.74, 0.89	0.51, 0.66
No. of measured, independent and observed [I > 2σ(I)] reflections	18605, 7318, 5579	52611, 14486, 9439
R_int	0.050	0.064
(sin θ/λ)_max (Å⁻¹)	0.607	0.727

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.083, 1.05	0.045, 0.124, 0.92
No. of reflections	7318	14486
No. of parameters	424	442
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.71	2.32, −2.11
Computer programs: APEX3 and SAINT (Bruker, 2015), SHELXT (Sheldrick, 2015a ), Mercury (Macrae et al., 2008 ), SHELXL2014 (Sheldrick, 2015b ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1533031; 1552112

Crystal structure: contains datablocks Global, II, I. DOI: https://doi.org/10.1107/S2056989017010295/su5375sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017010295/su5375Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989017010295/su5375IIsup4.hkl

checkCIF report

Computing details top

For both structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Methylenebis(triphenylphosphonium) diiodide dichloromethane disolvate (I) top

Crystal data top

C₃₇H₃₂P₂²⁺·2I⁻·2CH₂Cl₂	F(000) = 1896
M_r = 962.22	D_x = 1.624 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7510 (13) Å	Cell parameters from 3861 reflections
b = 22.914 (3) Å	θ = 2.8–24.4°
c = 18.204 (2) Å	µ = 1.98 mm⁻¹
β = 104.629 (2)°	T = 153 K
V = 3935.5 (9) Å³	Plate, colourless
Z = 4	0.14 × 0.12 × 0.06 mm

Data collection top

CCD area detector diffractometer	7318 independent reflections
Radiation source: fine-focus sealed tube, Bruker KappaCCD	5579 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 8.3333 pixels mm^-1	θ_max = 25.5°, θ_min = 2.7°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −27→27
T_min = 0.74, T_max = 0.89	l = −22→19
18605 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0157P)² + 9.1897P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
7318 reflections	Δρ_max = 0.65 e Å⁻³
424 parameters	Δρ_min = −0.71 e Å⁻³

Special details top

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

Refinement. (I: reflections 0 0 2, 1 0 0, 0 2 1, 1 1 0, -1 1 1, 0 2 0, 1 1 1, -1 2 4, -1 2 1 and 0 1 1, were affected by the beam stop and omitted from the final cycles of refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5915 (5)	0.66498 (19)	0.7366 (2)	0.0139 (10)
H1A	0.5834	0.6725	0.7889	0.017*
H1B	0.6265	0.6245	0.7362	0.017*
C2	0.3140 (5)	0.6175 (2)	0.7224 (3)	0.0179 (11)
C3	0.1671 (5)	0.6199 (2)	0.6984 (3)	0.0233 (12)
H3	0.1225	0.6458	0.6588	0.028*
C4	0.0859 (6)	0.5846 (2)	0.7323 (3)	0.0278 (13)
H4	−0.0146	0.5861	0.716	0.033*
C5	0.1509 (6)	0.5470 (2)	0.7900 (3)	0.0262 (13)
H5	0.095	0.5231	0.8137	0.031*
C6	0.2969 (6)	0.5441 (2)	0.8133 (3)	0.0247 (12)
H6	0.3414	0.5181	0.8528	0.03*
C7	0.3787 (6)	0.5791 (2)	0.7789 (3)	0.0221 (12)
H7	0.4791	0.5767	0.7943	0.026*
C8	0.3361 (5)	0.73662 (19)	0.6724 (3)	0.0160 (11)
C9	0.3560 (5)	0.7676 (2)	0.7407 (3)	0.0196 (11)
H9	0.4129	0.7519	0.7866	0.024*
C10	0.2921 (5)	0.8211 (2)	0.7402 (3)	0.0243 (12)
H10	0.3057	0.8423	0.7863	0.029*
C11	0.2087 (6)	0.8445 (2)	0.6744 (3)	0.0273 (13)
H11	0.1668	0.8819	0.6749	0.033*
C12	0.1868 (6)	0.8138 (2)	0.6085 (3)	0.0297 (13)
H12	0.1274	0.8295	0.5632	0.036*
C13	0.2501 (6)	0.7597 (2)	0.6065 (3)	0.0249 (12)
H13	0.2344	0.7387	0.5602	0.03*
C14	0.4079 (5)	0.6383 (2)	0.5839 (3)	0.0178 (11)
C15	0.3739 (6)	0.5799 (2)	0.5665 (3)	0.0265 (13)
H15	0.3481	0.5552	0.6028	0.032*
C16	0.3778 (6)	0.5583 (2)	0.4965 (3)	0.0296 (13)
H16	0.354	0.5186	0.4845	0.036*
C17	0.4160 (6)	0.5938 (2)	0.4434 (3)	0.0292 (13)
H17	0.4191	0.5784	0.3954	0.035*
C18	0.4496 (6)	0.6514 (2)	0.4606 (3)	0.0262 (13)
H18	0.475	0.6757	0.4238	0.031*
C19	0.4469 (5)	0.6746 (2)	0.5305 (3)	0.0202 (11)
H19	0.471	0.7143	0.5421	0.024*
C20	0.8846 (5)	0.6956 (2)	0.7980 (3)	0.0176 (11)
C21	0.8860 (5)	0.6523 (2)	0.8515 (3)	0.0212 (11)
H21	0.8018	0.6315	0.8516	0.025*
C22	1.0114 (6)	0.6397 (2)	0.9046 (3)	0.0249 (12)
H22	1.0131	0.6097	0.9408	0.03*
C23	1.1341 (6)	0.6703 (2)	0.9056 (3)	0.0269 (13)
H23	1.2197	0.6613	0.9423	0.032*
C24	1.1314 (6)	0.7142 (2)	0.8528 (3)	0.0264 (12)
H24	1.215	0.7357	0.8538	0.032*
C25	1.0084 (6)	0.7266 (2)	0.7991 (3)	0.0256 (12)
H25	1.0074	0.7564	0.7626	0.031*
C26	0.6846 (5)	0.7867 (2)	0.7281 (3)	0.0172 (11)
C27	0.7029 (5)	0.8101 (2)	0.8007 (3)	0.0226 (12)
H27	0.7453	0.7875	0.8442	0.027*
C28	0.6589 (6)	0.8667 (2)	0.8089 (3)	0.0292 (13)
H28	0.6709	0.883	0.8581	0.035*
C29	0.5976 (6)	0.8995 (2)	0.7454 (3)	0.0318 (14)
H29	0.5678	0.9383	0.751	0.038*
C30	0.5794 (6)	0.8761 (2)	0.6738 (3)	0.0315 (14)
H30	0.5378	0.8992	0.6306	0.038*
C31	0.6212 (5)	0.8193 (2)	0.6641 (3)	0.0238 (12)
H31	0.6067	0.803	0.6147	0.029*
C32	0.7769 (5)	0.6952 (2)	0.6357 (3)	0.0195 (11)
C33	0.8345 (5)	0.7377 (2)	0.5967 (3)	0.0235 (12)
H33	0.8408	0.7771	0.6132	0.028*
C34	0.8822 (6)	0.7217 (2)	0.5340 (3)	0.0309 (14)
H34	0.9199	0.7505	0.5071	0.037*
C35	0.8754 (6)	0.6651 (2)	0.5106 (3)	0.0281 (13)
H35	0.9083	0.6548	0.4675	0.034*
C36	0.8204 (6)	0.6220 (2)	0.5494 (3)	0.0294 (13)
H36	0.8179	0.5824	0.5336	0.035*
C37	0.7700 (5)	0.6376 (2)	0.6108 (3)	0.0210 (11)
H37	0.73	0.6087	0.6364	0.025*
C38	0.9861 (7)	0.9392 (3)	0.8330 (3)	0.0417 (16)
H38A	0.899	0.9367	0.791	0.05*
H38B	1.0557	0.9634	0.8154	0.05*
C39	0.7581 (8)	0.5313 (3)	0.9713 (3)	0.0547 (19)
H39A	0.6844	0.562	0.9607	0.066*
H39B	0.7995	0.5288	0.927	0.066*
Cl1	1.05582 (17)	0.86895 (7)	0.85465 (9)	0.0467 (4)
Cl2	0.9455 (2)	0.97306 (7)	0.91165 (10)	0.0580 (5)
Cl3	0.8912 (3)	0.55037 (10)	1.05242 (10)	0.0822 (7)
Cl4	0.6801 (2)	0.46429 (8)	0.98340 (10)	0.0677 (6)
I1	0.44524 (4)	0.31630 (2)	0.06172 (2)	0.02704 (10)
I2	0.28004 (4)	0.49269 (2)	0.25393 (2)	0.02568 (10)
P1	0.41286 (14)	0.66527 (5)	0.67665 (7)	0.0155 (3)
P2	0.73153 (14)	0.71173 (5)	0.72243 (7)	0.0155 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.018 (3)	0.015 (2)	0.012 (2)	0.000 (2)	0.011 (2)	−0.0007 (18)
C2	0.016 (3)	0.021 (3)	0.018 (3)	−0.003 (2)	0.007 (2)	0.000 (2)
C3	0.019 (3)	0.027 (3)	0.026 (3)	0.001 (2)	0.010 (3)	0.004 (2)
C4	0.020 (3)	0.033 (3)	0.032 (3)	−0.004 (2)	0.007 (3)	0.002 (2)
C5	0.028 (3)	0.025 (3)	0.031 (3)	−0.006 (2)	0.016 (3)	0.003 (2)
C6	0.033 (3)	0.027 (3)	0.016 (3)	0.004 (2)	0.007 (3)	0.004 (2)
C7	0.021 (3)	0.025 (3)	0.023 (3)	0.000 (2)	0.010 (3)	−0.003 (2)
C8	0.015 (3)	0.014 (2)	0.019 (3)	−0.003 (2)	0.004 (2)	0.0011 (19)
C9	0.011 (3)	0.027 (3)	0.020 (3)	0.000 (2)	0.003 (2)	0.002 (2)
C10	0.023 (3)	0.029 (3)	0.022 (3)	0.000 (2)	0.007 (3)	−0.009 (2)
C11	0.029 (3)	0.020 (3)	0.034 (3)	0.006 (2)	0.010 (3)	0.000 (2)
C12	0.031 (3)	0.027 (3)	0.028 (3)	0.007 (3)	0.001 (3)	0.007 (2)
C13	0.030 (3)	0.026 (3)	0.017 (3)	0.006 (2)	0.004 (3)	−0.006 (2)
C14	0.011 (3)	0.022 (3)	0.017 (3)	−0.001 (2)	−0.002 (2)	−0.001 (2)
C15	0.028 (3)	0.023 (3)	0.028 (3)	−0.005 (2)	0.006 (3)	−0.002 (2)
C16	0.035 (4)	0.021 (3)	0.031 (3)	−0.002 (2)	0.004 (3)	−0.008 (2)
C17	0.031 (3)	0.037 (3)	0.019 (3)	0.002 (3)	0.004 (3)	−0.010 (2)
C18	0.029 (3)	0.040 (3)	0.010 (2)	0.000 (3)	0.005 (2)	0.005 (2)
C19	0.020 (3)	0.022 (3)	0.019 (3)	−0.003 (2)	0.005 (2)	0.001 (2)
C20	0.016 (3)	0.018 (2)	0.019 (3)	0.002 (2)	0.003 (2)	−0.002 (2)
C21	0.017 (3)	0.027 (3)	0.019 (3)	−0.004 (2)	0.004 (2)	0.003 (2)
C22	0.023 (3)	0.030 (3)	0.021 (3)	0.000 (2)	0.005 (3)	0.008 (2)
C23	0.021 (3)	0.038 (3)	0.018 (3)	0.003 (3)	−0.003 (2)	0.001 (2)
C24	0.016 (3)	0.039 (3)	0.025 (3)	−0.004 (2)	0.006 (3)	0.004 (2)
C25	0.021 (3)	0.032 (3)	0.022 (3)	−0.006 (2)	0.002 (3)	0.002 (2)
C26	0.016 (3)	0.017 (2)	0.019 (3)	−0.001 (2)	0.006 (2)	−0.001 (2)
C27	0.013 (3)	0.027 (3)	0.029 (3)	−0.002 (2)	0.006 (2)	0.001 (2)
C28	0.025 (3)	0.030 (3)	0.032 (3)	−0.004 (3)	0.006 (3)	−0.007 (2)
C29	0.025 (3)	0.020 (3)	0.056 (4)	−0.003 (2)	0.020 (3)	−0.004 (3)
C30	0.029 (3)	0.026 (3)	0.039 (3)	0.005 (3)	0.009 (3)	0.011 (3)
C31	0.020 (3)	0.024 (3)	0.027 (3)	−0.003 (2)	0.006 (3)	0.001 (2)
C32	0.009 (3)	0.028 (3)	0.021 (3)	−0.001 (2)	0.003 (2)	0.002 (2)
C33	0.021 (3)	0.028 (3)	0.021 (3)	−0.002 (2)	0.004 (2)	0.002 (2)
C34	0.031 (3)	0.043 (3)	0.024 (3)	−0.002 (3)	0.017 (3)	0.011 (3)
C35	0.026 (3)	0.045 (3)	0.015 (3)	0.008 (3)	0.008 (3)	0.003 (2)
C36	0.027 (3)	0.038 (3)	0.024 (3)	0.002 (3)	0.008 (3)	−0.007 (2)
C37	0.023 (3)	0.024 (3)	0.018 (3)	0.003 (2)	0.008 (2)	0.000 (2)
C38	0.050 (4)	0.043 (4)	0.042 (4)	−0.011 (3)	0.027 (4)	−0.002 (3)
C39	0.077 (6)	0.049 (4)	0.036 (4)	0.004 (4)	0.008 (4)	0.007 (3)
Cl1	0.0424 (10)	0.0460 (9)	0.0603 (10)	−0.0025 (8)	0.0290 (9)	−0.0043 (8)
Cl2	0.0904 (15)	0.0384 (9)	0.0600 (11)	−0.0085 (9)	0.0462 (11)	−0.0062 (8)
Cl3	0.1066 (18)	0.0915 (15)	0.0420 (10)	−0.0446 (14)	0.0070 (12)	0.0157 (10)
Cl4	0.0869 (16)	0.0624 (12)	0.0483 (10)	−0.0130 (11)	0.0067 (11)	0.0028 (9)
I1	0.0287 (2)	0.0339 (2)	0.01825 (17)	0.00212 (16)	0.00550 (16)	−0.00344 (15)
I2	0.0279 (2)	0.01925 (17)	0.0337 (2)	0.00037 (15)	0.01483 (17)	0.00000 (14)
P1	0.0156 (7)	0.0181 (6)	0.0130 (6)	−0.0011 (5)	0.0041 (6)	−0.0004 (5)
P2	0.0150 (7)	0.0172 (6)	0.0143 (6)	0.0007 (5)	0.0037 (6)	−0.0001 (5)

Geometric parameters (Å, º) top

C1—P2	1.804 (4)	C20—C25	1.396 (7)
C1—P1	1.807 (5)	C20—P2	1.794 (5)
C2—C7	1.380 (7)	C21—C22	1.384 (7)
C2—C3	1.389 (7)	C22—C23	1.383 (7)
C2—P1	1.795 (5)	C23—C24	1.387 (7)
C3—C4	1.383 (7)	C24—C25	1.372 (7)
C4—C5	1.381 (7)	C26—C31	1.391 (7)
C5—C6	1.381 (7)	C26—C27	1.396 (6)
C6—C7	1.387 (7)	C26—P2	1.787 (5)
C8—C13	1.383 (7)	C27—C28	1.385 (7)
C8—C9	1.402 (6)	C28—C29	1.382 (7)
C8—P1	1.792 (5)	C29—C30	1.377 (7)
C9—C10	1.373 (7)	C30—C31	1.390 (7)
C10—C11	1.376 (7)	C32—C37	1.391 (7)
C11—C12	1.360 (7)	C32—C33	1.403 (7)
C12—C13	1.388 (7)	C32—P2	1.786 (5)
C14—C15	1.396 (6)	C33—C34	1.385 (7)
C14—C19	1.403 (6)	C34—C35	1.361 (7)
C14—P1	1.787 (5)	C35—C36	1.397 (7)
C15—C16	1.377 (7)	C36—C37	1.376 (7)
C16—C17	1.384 (7)	C38—Cl1	1.754 (6)
C17—C18	1.377 (7)	C38—Cl2	1.760 (6)
C18—C19	1.387 (6)	C39—Cl4	1.752 (7)
C20—C21	1.388 (6)	C39—Cl3	1.758 (7)

P1—C1—P2	124.1 (2)	C24—C25—C20	120.1 (5)
C7—C2—C3	120.0 (5)	C31—C26—C27	120.6 (4)
C7—C2—P1	122.4 (4)	C31—C26—P2	122.3 (4)
C3—C2—P1	117.5 (4)	C27—C26—P2	116.9 (4)
C4—C3—C2	119.9 (5)	C28—C27—C26	119.6 (5)
C5—C4—C3	120.0 (5)	C29—C28—C27	119.9 (5)
C6—C5—C4	120.2 (5)	C30—C29—C28	120.4 (5)
C5—C6—C7	119.9 (5)	C29—C30—C31	120.9 (5)
C2—C7—C6	119.9 (5)	C30—C31—C26	118.7 (5)
C13—C8—C9	119.5 (4)	C37—C32—C33	119.1 (4)
C13—C8—P1	122.8 (4)	C37—C32—P2	119.2 (4)
C9—C8—P1	117.5 (4)	C33—C32—P2	121.4 (4)
C10—C9—C8	119.1 (5)	C34—C33—C32	119.6 (5)
C9—C10—C11	121.3 (5)	C35—C34—C33	120.6 (5)
C12—C11—C10	119.6 (5)	C34—C35—C36	120.6 (5)
C11—C12—C13	120.8 (5)	C37—C36—C35	119.2 (5)
C8—C13—C12	119.7 (4)	C36—C37—C32	120.8 (5)
C15—C14—C19	120.2 (4)	Cl1—C38—Cl2	112.1 (3)
C15—C14—P1	119.6 (4)	Cl4—C39—Cl3	111.4 (3)
C19—C14—P1	120.1 (4)	C14—P1—C8	111.3 (2)
C16—C15—C14	119.6 (5)	C14—P1—C2	109.7 (2)
C15—C16—C17	120.7 (5)	C8—P1—C2	107.9 (2)
C18—C17—C16	119.7 (5)	C14—P1—C1	111.2 (2)
C17—C18—C19	121.1 (5)	C8—P1—C1	111.0 (2)
C18—C19—C14	118.7 (5)	C2—P1—C1	105.5 (2)
C21—C20—C25	119.9 (5)	C32—P2—C26	112.3 (2)
C21—C20—P2	123.0 (4)	C32—P2—C20	106.8 (2)
C25—C20—P2	117.1 (4)	C26—P2—C20	109.2 (2)
C22—C21—C20	119.3 (5)	C32—P2—C1	111.5 (2)
C23—C22—C21	120.8 (5)	C26—P2—C1	110.4 (2)
C22—C23—C24	119.5 (5)	C20—P2—C1	106.3 (2)
C25—C24—C23	120.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···I1ⁱ	0.99	2.81	3.802 (4)	175
C39—H39A···I1ⁱ	0.99	3.05	3.986 (7)	159
C1—H1B···I2ⁱ	0.99	2.83	3.813 (4)	175
C38—H38B···I2ⁱⁱ	0.99	2.88	3.848 (6)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z+1/2.

Methylenebis(triphenylphosphonium) bis(tetraiodoborate) (II) top

Crystal data top

C₃₇H₃₂P₂²⁺·2BI₄⁻	F(000) = 2872
M_r = 1575.38	D_x = 2.314 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.7878 (6) Å	Cell parameters from 7264 reflections
b = 14.3122 (3) Å	θ = 2.5–25.5°
c = 16.0646 (4) Å	µ = 5.58 mm⁻¹
β = 96.230 (1)°	T = 153 K
V = 4522.7 (2) Å³	Block, colourless
Z = 4	0.14 × 0.12 × 0.08 mm

Data collection top

CCD area detector diffractometer	14486 independent reflections
Radiation source: fine-focus sealed tube, Bruker KappaCCD	9439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
Detector resolution: 8.3333 pixels mm^-1	θ_max = 31.1°, θ_min = 1.8°
phi and ω scans	h = −28→27
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −20→20
T_min = 0.51, T_max = 0.66	l = −23→19
52611 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0618P)² + 4.3616P] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max = 0.001
14486 reflections	Δρ_max = 2.32 e Å⁻³
442 parameters	Δρ_min = −2.11 e Å⁻³

Special details top

Refinement. II: reflections 0 0 2, 2 0 0, 1 1 1, 2 1 0, -1 0 2, -2 1 1, -1 1 1 and 0 1 2, were affected by the beam stop and omitted from the final cycles of refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.4572 (3)	0.0659 (4)	0.2238 (4)	0.0196 (12)
B2	0.9220 (3)	0.4312 (4)	0.1661 (4)	0.0209 (12)
C1	0.6997 (3)	0.5283 (3)	0.5764 (3)	0.0163 (10)
H1A	0.689	0.5285	0.5148	0.02*
H1B	0.6557	0.5311	0.6003	0.02*
C2	0.6780 (3)	0.3291 (3)	0.5616 (4)	0.0194 (11)
C3	0.6740 (3)	0.2450 (4)	0.6055 (4)	0.0336 (15)
H3	0.6999	0.236	0.6582	0.04*
C4	0.6314 (4)	0.1752 (4)	0.5707 (6)	0.046 (2)
H4	0.6286	0.1177	0.5996	0.056*
C5	0.5937 (3)	0.1876 (5)	0.4963 (5)	0.0428 (19)
H5	0.5651	0.1385	0.4736	0.051*
C6	0.5958 (3)	0.2702 (5)	0.4526 (5)	0.0398 (16)
H6	0.5683	0.2788	0.401	0.048*
C7	0.6390 (3)	0.3410 (4)	0.4857 (4)	0.0321 (14)
H7	0.6417	0.3979	0.4558	0.039*
C8	0.8151 (3)	0.4054 (3)	0.5583 (4)	0.0186 (10)
C9	0.8776 (3)	0.4303 (4)	0.6004 (4)	0.0238 (12)
H9	0.8806	0.448	0.6576	0.029*
C10	0.9357 (3)	0.4292 (4)	0.5589 (4)	0.0298 (14)
H10	0.9785	0.4454	0.5879	0.036*
C11	0.9310 (3)	0.4046 (4)	0.4758 (5)	0.0333 (15)
H11	0.9707	0.4045	0.4474	0.04*
C12	0.8694 (3)	0.3799 (4)	0.4332 (4)	0.0287 (13)
H12	0.8668	0.3633	0.3757	0.034*
C13	0.8110 (3)	0.3791 (4)	0.4739 (4)	0.0241 (12)
H13	0.7687	0.361	0.4448	0.029*
C14	0.7477 (3)	0.4003 (3)	0.7157 (3)	0.0183 (10)
C15	0.6960 (3)	0.4326 (4)	0.7618 (4)	0.0249 (12)
H15	0.6581	0.4654	0.7347	0.03*
C16	0.7009 (3)	0.4160 (4)	0.8470 (4)	0.0309 (13)
H16	0.666	0.4374	0.8785	0.037*
C17	0.7562 (4)	0.3684 (4)	0.8869 (4)	0.0336 (14)
H17	0.7594	0.3582	0.9456	0.04*
C18	0.8066 (3)	0.3357 (4)	0.8414 (4)	0.0331 (14)
H18	0.8443	0.3029	0.869	0.04*
C19	0.8024 (3)	0.3507 (4)	0.7556 (4)	0.0237 (11)
H19	0.8367	0.3271	0.7243	0.028*
C20	0.6845 (3)	0.7276 (3)	0.5731 (3)	0.0177 (10)
C21	0.6246 (3)	0.7120 (4)	0.5224 (3)	0.0209 (11)
H21	0.6117	0.6502	0.5061	0.025*
C22	0.5832 (3)	0.7867 (4)	0.4954 (4)	0.0282 (13)
H22	0.542	0.7764	0.4604	0.034*
C23	0.6024 (4)	0.8767 (4)	0.5201 (4)	0.0342 (15)
H23	0.5738	0.9279	0.5026	0.041*
C24	0.6626 (3)	0.8924 (4)	0.5695 (4)	0.0311 (14)
H24	0.6757	0.9544	0.585	0.037*
C25	0.7040 (3)	0.8184 (4)	0.5966 (4)	0.0258 (12)
H25	0.7454	0.8292	0.6311	0.031*
C26	0.8159 (2)	0.6531 (3)	0.5470 (3)	0.0156 (10)
C27	0.8679 (3)	0.7133 (4)	0.5778 (4)	0.0222 (11)
H27	0.8692	0.7374	0.6331	0.027*
C28	0.9174 (3)	0.7379 (4)	0.5279 (4)	0.0294 (13)
H28	0.9526	0.7796	0.5485	0.035*
C29	0.9159 (3)	0.7025 (4)	0.4487 (4)	0.0264 (13)
H29	0.9504	0.7199	0.415	0.032*
C30	0.8655 (3)	0.6422 (4)	0.4165 (4)	0.0268 (13)
H30	0.8655	0.6175	0.3617	0.032*
C31	0.8144 (3)	0.6179 (4)	0.4658 (4)	0.0215 (11)
H31	0.7786	0.5776	0.4442	0.026*
C32	0.7668 (3)	0.6419 (3)	0.7154 (3)	0.0177 (10)
C33	0.8287 (3)	0.6088 (3)	0.7527 (3)	0.0182 (10)
H33	0.863	0.5903	0.719	0.022*
C34	0.8404 (3)	0.6030 (4)	0.8390 (4)	0.0273 (12)
H34	0.8825	0.5797	0.8647	0.033*
C35	0.7913 (4)	0.6309 (4)	0.8873 (4)	0.0335 (14)
H35	0.7993	0.6254	0.9465	0.04*
C36	0.7303 (3)	0.6667 (4)	0.8515 (4)	0.0311 (14)
H36	0.6974	0.6881	0.886	0.037*
C37	0.7170 (3)	0.6715 (4)	0.7645 (4)	0.0254 (12)
H37	0.6747	0.6946	0.7392	0.03*
I1	0.50473 (2)	−0.01702 (3)	0.33197 (3)	0.02907 (10)
I2	0.34522 (2)	0.03252 (3)	0.19998 (3)	0.03574 (11)
I3	0.50580 (2)	0.02646 (4)	0.11044 (3)	0.03911 (12)
I4	0.47021 (2)	0.21823 (3)	0.24780 (3)	0.03478 (11)
I5	0.81419 (2)	0.44916 (3)	0.19353 (3)	0.04437 (13)
I6	0.97031 (2)	0.31216 (3)	0.24298 (3)	0.02826 (10)
I7	0.92629 (3)	0.40188 (4)	0.03197 (3)	0.04945 (14)
I8	0.97951 (3)	0.56167 (3)	0.20371 (3)	0.04060 (12)
P1	0.73738 (7)	0.41452 (9)	0.60508 (9)	0.0155 (3)
P2	0.74413 (6)	0.63678 (8)	0.60451 (8)	0.0139 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.014 (3)	0.027 (3)	0.017 (3)	−0.003 (2)	−0.002 (2)	−0.004 (2)
B2	0.020 (3)	0.022 (3)	0.020 (3)	0.001 (2)	−0.001 (2)	−0.004 (2)
C1	0.013 (2)	0.015 (2)	0.020 (3)	0.0006 (18)	0.001 (2)	0.0000 (18)
C2	0.012 (2)	0.020 (2)	0.026 (3)	−0.0061 (18)	0.001 (2)	−0.004 (2)
C3	0.036 (4)	0.019 (3)	0.045 (4)	−0.006 (2)	0.002 (3)	−0.002 (3)
C4	0.047 (4)	0.017 (3)	0.076 (6)	−0.009 (3)	0.008 (4)	−0.006 (3)
C5	0.026 (3)	0.035 (3)	0.068 (5)	−0.011 (3)	0.009 (3)	−0.026 (3)
C6	0.028 (3)	0.050 (4)	0.039 (4)	−0.007 (3)	−0.007 (3)	−0.016 (3)
C7	0.036 (4)	0.029 (3)	0.030 (3)	−0.009 (3)	0.000 (3)	−0.002 (2)
C8	0.019 (3)	0.014 (2)	0.025 (3)	−0.0005 (19)	0.008 (2)	−0.0023 (19)
C9	0.018 (3)	0.026 (3)	0.028 (3)	0.000 (2)	0.000 (2)	0.000 (2)
C10	0.019 (3)	0.026 (3)	0.045 (4)	0.002 (2)	0.004 (3)	0.000 (3)
C11	0.026 (3)	0.029 (3)	0.047 (4)	0.003 (2)	0.013 (3)	−0.003 (3)
C12	0.033 (3)	0.027 (3)	0.028 (3)	0.000 (2)	0.012 (3)	−0.005 (2)
C13	0.022 (3)	0.026 (3)	0.024 (3)	−0.003 (2)	0.002 (2)	−0.005 (2)
C14	0.022 (3)	0.016 (2)	0.016 (3)	−0.0050 (19)	−0.001 (2)	0.0026 (18)
C15	0.021 (3)	0.031 (3)	0.023 (3)	−0.001 (2)	0.001 (2)	0.003 (2)
C16	0.029 (3)	0.042 (3)	0.023 (3)	−0.003 (3)	0.005 (3)	0.001 (3)
C17	0.041 (4)	0.040 (3)	0.020 (3)	−0.001 (3)	0.003 (3)	0.009 (3)
C18	0.036 (4)	0.034 (3)	0.027 (3)	0.003 (3)	−0.010 (3)	0.015 (3)
C19	0.027 (3)	0.024 (3)	0.019 (3)	0.002 (2)	−0.001 (2)	0.000 (2)
C20	0.019 (3)	0.017 (2)	0.018 (3)	0.0048 (18)	0.004 (2)	−0.0011 (19)
C21	0.019 (3)	0.026 (3)	0.017 (3)	0.004 (2)	−0.001 (2)	−0.001 (2)
C22	0.026 (3)	0.042 (3)	0.015 (3)	0.012 (3)	−0.001 (2)	0.003 (2)
C23	0.048 (4)	0.035 (3)	0.020 (3)	0.023 (3)	0.007 (3)	0.002 (2)
C24	0.044 (4)	0.021 (3)	0.027 (3)	0.011 (3)	−0.002 (3)	0.001 (2)
C25	0.027 (3)	0.020 (2)	0.029 (3)	0.004 (2)	−0.002 (2)	−0.002 (2)
C26	0.012 (2)	0.014 (2)	0.021 (3)	−0.0003 (17)	0.0027 (19)	0.0021 (18)
C27	0.017 (3)	0.030 (3)	0.019 (3)	−0.006 (2)	−0.001 (2)	0.001 (2)
C28	0.020 (3)	0.032 (3)	0.036 (4)	−0.006 (2)	0.004 (3)	0.004 (3)
C29	0.020 (3)	0.029 (3)	0.032 (3)	0.002 (2)	0.012 (2)	0.010 (2)
C30	0.030 (3)	0.026 (3)	0.025 (3)	0.008 (2)	0.008 (3)	0.005 (2)
C31	0.023 (3)	0.022 (2)	0.021 (3)	0.002 (2)	0.006 (2)	0.000 (2)
C32	0.017 (2)	0.017 (2)	0.019 (3)	−0.0017 (18)	−0.001 (2)	−0.0002 (19)
C33	0.017 (3)	0.019 (2)	0.018 (3)	−0.0006 (19)	−0.001 (2)	−0.0029 (19)
C34	0.022 (3)	0.031 (3)	0.026 (3)	−0.002 (2)	−0.009 (2)	0.001 (2)
C35	0.045 (4)	0.042 (3)	0.014 (3)	−0.008 (3)	0.005 (3)	−0.004 (2)
C36	0.036 (4)	0.036 (3)	0.023 (3)	0.001 (3)	0.010 (3)	−0.004 (2)
C37	0.022 (3)	0.028 (3)	0.026 (3)	0.004 (2)	0.006 (2)	−0.005 (2)
I1	0.0364 (2)	0.02556 (18)	0.0242 (2)	0.00250 (15)	−0.00166 (16)	0.00448 (15)
I2	0.01692 (19)	0.0617 (3)	0.0287 (2)	−0.00711 (17)	0.00315 (16)	−0.01338 (19)
I3	0.0213 (2)	0.0782 (3)	0.0185 (2)	0.0046 (2)	0.00497 (16)	−0.0110 (2)
I4	0.0394 (2)	0.02487 (18)	0.0370 (2)	−0.00048 (16)	−0.00956 (19)	0.00293 (16)
I5	0.0205 (2)	0.0557 (3)	0.0576 (3)	0.01384 (19)	0.0074 (2)	0.0110 (2)
I6	0.02340 (19)	0.02538 (17)	0.0370 (2)	0.00730 (14)	0.00765 (16)	0.00962 (15)
I7	0.0586 (3)	0.0673 (3)	0.0207 (2)	0.0183 (3)	−0.0038 (2)	−0.0119 (2)
I8	0.0512 (3)	0.02285 (19)	0.0443 (3)	−0.00971 (18)	−0.0105 (2)	−0.00049 (17)
P1	0.0129 (6)	0.0158 (6)	0.0175 (7)	−0.0006 (5)	−0.0006 (5)	0.0012 (5)
P2	0.0108 (6)	0.0163 (6)	0.0143 (6)	0.0015 (4)	0.0001 (5)	−0.0008 (5)

Geometric parameters (Å, º) top

B1—I3	2.224 (6)	C14—P1	1.779 (5)
B1—I4	2.224 (6)	C15—C16	1.382 (8)
B1—I1	2.226 (6)	C16—C17	1.386 (9)
B1—I2	2.258 (6)	C17—C18	1.380 (9)
B2—I7	2.206 (6)	C18—C19	1.389 (8)
B2—I8	2.236 (6)	C20—C21	1.382 (8)
B2—I5	2.241 (6)	C20—C25	1.396 (7)
B2—I6	2.255 (6)	C20—P2	1.791 (5)
C1—P2	1.817 (5)	C21—C22	1.388 (7)
C1—P1	1.829 (5)	C22—C23	1.388 (9)
C2—C7	1.382 (8)	C23—C24	1.376 (10)
C2—C3	1.402 (8)	C24—C25	1.381 (8)
C2—P1	1.784 (5)	C26—C27	1.390 (7)
C3—C4	1.385 (9)	C26—C31	1.395 (7)
C4—C5	1.350 (11)	C26—P2	1.792 (5)
C5—C6	1.377 (10)	C27—C28	1.378 (8)
C6—C7	1.394 (8)	C28—C29	1.368 (9)
C8—C9	1.390 (8)	C29—C30	1.376 (8)
C8—C13	1.400 (8)	C30—C31	1.394 (8)
C8—P1	1.788 (5)	C32—C33	1.389 (7)
C9—C10	1.389 (8)	C32—C37	1.392 (7)
C10—C11	1.374 (9)	C32—P2	1.791 (5)
C11—C12	1.379 (9)	C33—C34	1.384 (8)
C12—C13	1.387 (8)	C34—C35	1.367 (9)
C14—C19	1.391 (8)	C35—C36	1.377 (9)
C14—C15	1.405 (8)	C36—C37	1.396 (9)

I3—B1—I4	109.8 (3)	C21—C20—C25	120.3 (5)
I3—B1—I1	108.7 (3)	C21—C20—P2	123.1 (4)
I4—B1—I1	110.9 (3)	C25—C20—P2	116.5 (4)
I3—B1—I2	108.1 (3)	C20—C21—C22	120.0 (5)
I4—B1—I2	109.3 (3)	C23—C22—C21	119.4 (6)
I1—B1—I2	110.1 (3)	C24—C23—C22	120.7 (5)
I7—B2—I8	110.5 (3)	C23—C24—C25	120.2 (6)
I7—B2—I5	110.6 (3)	C24—C25—C20	119.4 (6)
I8—B2—I5	108.6 (2)	C27—C26—C31	119.8 (5)
I7—B2—I6	109.4 (2)	C27—C26—P2	119.6 (4)
I8—B2—I6	108.1 (3)	C31—C26—P2	119.8 (4)
I5—B2—I6	109.6 (3)	C28—C27—C26	119.7 (5)
P1—C1—P2	121.7 (3)	C29—C28—C27	120.2 (6)
C7—C2—C3	119.5 (5)	C28—C29—C30	121.6 (5)
C7—C2—P1	122.8 (4)	C29—C30—C31	118.9 (6)
C3—C2—P1	117.6 (5)	C30—C31—C26	119.8 (5)
C4—C3—C2	118.8 (7)	C33—C32—C37	120.3 (5)
C5—C4—C3	121.1 (7)	C33—C32—P2	121.9 (4)
C4—C5—C6	121.3 (6)	C37—C32—P2	117.4 (4)
C5—C6—C7	118.8 (7)	C34—C33—C32	119.7 (5)
C2—C7—C6	120.5 (6)	C35—C34—C33	120.0 (6)
C9—C8—C13	119.6 (5)	C34—C35—C36	121.0 (6)
C9—C8—P1	122.5 (4)	C35—C36—C37	119.9 (6)
C13—C8—P1	117.7 (4)	C32—C37—C36	119.0 (6)
C10—C9—C8	120.2 (6)	C14—P1—C2	108.2 (3)
C11—C10—C9	119.8 (6)	C14—P1—C8	113.6 (3)
C10—C11—C12	120.7 (6)	C2—P1—C8	110.2 (2)
C11—C12—C13	120.3 (6)	C14—P1—C1	110.7 (2)
C12—C13—C8	119.4 (5)	C2—P1—C1	106.2 (2)
C19—C14—C15	120.0 (5)	C8—P1—C1	107.8 (2)
C19—C14—P1	121.2 (4)	C32—P2—C20	109.7 (2)
C15—C14—P1	118.5 (4)	C32—P2—C26	112.4 (2)
C16—C15—C14	119.3 (6)	C20—P2—C26	107.2 (2)
C15—C16—C17	120.5 (6)	C32—P2—C1	110.1 (2)
C18—C17—C16	120.2 (6)	C20—P2—C1	105.3 (2)
C17—C18—C19	120.3 (6)	C26—P2—C1	111.9 (2)
C18—C19—C14	119.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···I1ⁱ	0.95	3.02	3.730 (7)	132

Symmetry code: (i) x, y+1, z.

Acknowledgements

RG thanks the CBC, Nanyang Technological University, for the instrument facilities.

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