Diethyl [(2,5-di­iodo-4-methyl­phen­yl)meth­yl]phospho­nate

Schollmeyer, D.; Sadovski, O.; Detert, H.

doi:10.1107/S2414314621006544

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 6| June 2021| x210654

https://doi.org/10.1107/S2414314621006544

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Diethyl [(2,5-diiodo-4-methylphenyl)methyl]phosphonate

Dieter Schollmeyer,^a Oleg Sadovski ^a and Heiner Detert ^a ^*

^aUniversity of Mainz, Institut for Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: detert@uni-mainz.de

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 21 June 2021; accepted 22 June 2021; online 30 June 2021)

The title compound, C₁₂H₁₇I₂O₃P, was prepared in three steps from p-xylene. Heterodimers between nearly identical molecules are connected via three hydrogen bonds from benzylic and ester methylene groups to phosphonate. The dimers form chains along the a-axis direction, stabilized by C—H⋯O bridges.

Keywords: crystal structure; iodine; phosphonate; two-component twin.

CCDC reference: 2091488

Structure description

In a project focusing on phenylenevinylene emissive materials (Sugioni & Detert, 2004 ; Schmitt et al., 2008 , 2013 ) and their electrical and magnetic properties (Cambré et al., 2007 ; Nemkovich et al., 2010 ), the title compound was prepared as an intermediate for fluorophores with an E-type delayed emission and has been used for the synthesis of π-conjugated cruciforms (Zucchero et al., 2006 ). The asymmetric unit contains four molecules. Heterodimers are formed via C—H⋯O hydrogen bonds (Table 1) between nearly identical molecules A and B. The only significant difference between A and B (Fig. 1) is the conformation of one ethoxy group. The aromatic unit with its four substituents is nearly perfectly planar, with a maximum deviation from the mean plane of 0.013 (16) Å at C3A. The bond angles on the 1,2,4,5-tetrasubstituted ring nearly match the ideal 120°, only the arene-methylene bond is slightly bent [125.6 (12)° A, 123.4(13°) B]. The A,B dimers are connected via three slightly bent C—H⋯O hydrogen bridges: C7A—H7A⋯O9B [3.275 (15) Å, 154.3°], C14A—H14B⋯O9B [3.407 (18) Å, 172.2°], and C11B—H11D⋯O9A [3.575 (18) Å, 168.5°]. Three further C—H⋯O bridges connect neighbouring dimers to form chains along the a-axis direction (Fig. 2): C11A—H11A⋯O9B [3.377 (17) Å 157.9°, B shifted −1 along a], C7B—H7C⋯O9A [3.388 (15) Å, 151.6°, A shifted +1 along a] and C14B—H14D⋯O9A [3.324 (19) Å, 165.6°, A shifted +1 along a].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7A⋯O9B	0.99	2.36	3.275 (15)	154
C11A—H11B⋯O9Bⁱ	0.99	2.44	3.377 (17)	158
C14A—H14B⋯O9B	0.99	2.42	3.407 (18)	172
C7B—H7C⋯O9Aⁱⁱ	0.99	2.48	3.388 (15)	152
C11B—H11D⋯O9A	0.99	2.60	3.575 (18)	169
C14B—H14D⋯O9Aⁱⁱ	0.99	2.36	3.324 (19)	166
Symmetry codes: (i) ; (ii) x+1, y, z.

Figure 1
View of the two independent molecules in the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Part of the packing diagram. View along the b axis. Hydrogen bonds are drawn with dashed lines. The two independent molecules are drawn in different colours.

Synthesis and crystallization

The title compound was prepared from p-xylene via iodination according to Wirth et al. (1964 ) and bromination (Wheland & Martin, 1975 ) followed by Michaelis–Arbusov reaction. Purification was via column chromatography on silica with an eluent gradient. Starting with toluene/ethyl acetate 1/1, the polarity was increased by reducing the toluene concentration first and addition of increasing amounts of methanol. A mixture of the diiodo compound and some bromo-iodo analogues was obtained. The title compound crystallized from the oily product mixture within 12 years.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal was a two component twin. The fractional contribution of the major domain refined to 0.5155 (14).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₇I₂O₃P
M_r	494.02
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	120
a, b, c (Å)	7.4909 (6), 10.9201 (9), 20.4720 (17)
α, β, γ (°)	89.070 (7), 80.799 (6), 71.451 (6)
V (Å³)	1566.1 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	4.12
Crystal size (mm)	0.11 × 0.10 × 0.04

Data collection
Diffractometer	Stoe IPDS 2T
Absorption correction	Integration (X-RED32; Stoe & Cie, 2019 )
T_min, T_max	0.651, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	22662, 22662, 15127
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.186, 1.09
No. of reflections	22662
No. of parameters	332
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.69, −1.26
Computer programs: X-AREA WinXpose, Recipe and Integrate (Stoe & Cie, 2019), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2091488

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314621006544/bt4116sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621006544/bt4116Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621006544/bt4116Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA WinXpose 2.0.22.0 (Stoe & Cie, 2019); cell refinement: X-AREA Recipe 1.36.0 (Stoe & Cie, 2019); data reduction: X-AREA Integrate 1.78.3 (Stoe & Cie, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020).

Diethyl [(2,5-diiodo-4-methylphenyl)methyl]phosphonate top

Crystal data top

C₁₂H₁₇I₂O₃P	Z = 4
M_r = 494.02	F(000) = 936
Triclinic, P1	D_x = 2.095 Mg m⁻³
a = 7.4909 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9201 (9) Å	Cell parameters from 14985 reflections
c = 20.4720 (17) Å	θ = 2.9–28.3°
α = 89.070 (7)°	µ = 4.12 mm⁻¹
β = 80.799 (6)°	T = 120 K
γ = 71.451 (6)°	Column, colourless
V = 1566.1 (2) Å³	0.11 × 0.10 × 0.04 mm

Data collection top

Stoe IPDS 2T diffractometer	22662 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	15127 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.0°, θ_min = 2.8°
rotation method scans	h = −9→9
Absorption correction: integration (X-Red32; Stoe & Cie, 2019)	k = −14→14
T_min = 0.651, T_max = 0.820	l = −26→26
22662 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.186	w = 1/[σ²(F_o²) + (0.0494P)² + 24.353P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
22662 reflections	Δρ_max = 1.69 e Å⁻³
332 parameters	Δρ_min = −1.26 e Å⁻³
0 restraints

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. Hydrogen atoms were placed at calculated positions and were refined in the riding-model approximation with C_aromatic–H = 0.95 Å, C_methylene–H = 0.99 Å, C_methyl–H = 0.98 Å, and with U_iso(H) = 1.2 U_eq(C_aromatic, C_methylene) or with U_iso(H) = 1.5 U_eq(C_methyl).

Refined as a 2-component twin. Twin law for transforming hkl(1) to hkl(2): 0.97100 0.03900 0.01800 0.98600 -0.98000 0.00900 0.98600 0.02000 -0.99100

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

	x	y	z	U_iso*/U_eq
I1A	0.75872 (15)	−0.26269 (8)	0.13371 (5)	0.0327 (2)
I2A	0.68923 (17)	0.33082 (9)	−0.00063 (5)	0.0394 (3)
C1A	0.6926 (18)	0.0275 (12)	0.1389 (6)	0.023 (3)
C2A	0.7307 (18)	−0.0795 (11)	0.0976 (6)	0.021 (2)
C3A	0.749 (2)	−0.0701 (13)	0.0282 (7)	0.028 (3)
H3A	0.768361	−0.144994	0.001490	0.033*
C4A	0.739 (2)	0.0447 (13)	−0.0017 (6)	0.027 (3)
C5A	0.701 (2)	0.1543 (12)	0.0394 (7)	0.028 (3)
C6A	0.6802 (19)	0.1462 (11)	0.1077 (6)	0.023 (3)
H6A	0.656970	0.221900	0.134250	0.028*
C7A	0.6757 (18)	0.0270 (12)	0.2123 (6)	0.022 (2)
H7A	0.748898	0.080342	0.226169	0.026*
H7B	0.734980	−0.062605	0.225433	0.026*
P8A	0.4346 (5)	0.0866 (3)	0.25589 (16)	0.0222 (6)
O9A	0.3240 (14)	0.2183 (8)	0.2406 (5)	0.030 (2)
O10A	0.3510 (13)	−0.0234 (8)	0.2415 (4)	0.0245 (19)
C11A	0.147 (2)	−0.0070 (14)	0.2546 (8)	0.035 (3)
H11A	0.115876	−0.058664	0.221468	0.042*
H11B	0.072998	0.084949	0.250701	0.042*
C12A	0.093 (2)	−0.0489 (17)	0.3216 (8)	0.043 (4)
H12A	−0.040769	−0.045706	0.328067	0.064*
H12B	0.110157	0.008676	0.354638	0.064*
H12C	0.174274	−0.137581	0.326763	0.064*
O13A	0.4539 (15)	0.0703 (9)	0.3315 (4)	0.028 (2)
C14A	0.495 (2)	0.1709 (14)	0.3673 (7)	0.031 (3)
H14A	0.374929	0.242258	0.382349	0.038*
H14B	0.582833	0.206435	0.337867	0.038*
C15A	0.583 (3)	0.1122 (17)	0.4254 (9)	0.053 (5)
H15A	0.486186	0.093330	0.458543	0.080*
H15B	0.633866	0.172867	0.444834	0.080*
H15C	0.686594	0.031969	0.411094	0.080*
C16A	0.764 (2)	0.0499 (15)	−0.0766 (7)	0.034 (3)
H16A	0.771780	−0.033817	−0.095456	0.051*
H16B	0.881793	0.069548	−0.093195	0.051*
H16C	0.654934	0.117414	−0.089395	0.051*
I1B	0.63866 (15)	0.75758 (9)	0.36179 (5)	0.0338 (2)
I2B	1.01458 (17)	0.17183 (9)	0.50120 (5)	0.0397 (3)
C1B	0.868 (2)	0.4691 (13)	0.3608 (7)	0.026 (3)
C2B	0.752 (2)	0.5771 (13)	0.4004 (7)	0.027 (3)
C3B	0.713 (2)	0.5666 (13)	0.4682 (6)	0.027 (3)
H3B	0.635236	0.641517	0.494047	0.032*
C4B	0.782 (2)	0.4539 (13)	0.5001 (7)	0.026 (3)
C5B	0.896 (2)	0.3482 (12)	0.4599 (6)	0.024 (3)
C6B	0.9378 (18)	0.3541 (13)	0.3916 (7)	0.025 (3)
H6B	1.014923	0.278705	0.365942	0.030*
C7B	0.9231 (19)	0.4726 (12)	0.2861 (6)	0.026 (3)
H7C	1.060215	0.423153	0.273632	0.031*
H7D	0.905885	0.563363	0.274129	0.031*
P8B	0.7894 (5)	0.4086 (3)	0.23870 (16)	0.0238 (7)
O9B	0.7928 (15)	0.2762 (8)	0.2537 (5)	0.030 (2)
O10B	0.5903 (14)	0.5151 (9)	0.2494 (5)	0.031 (2)
C11B	0.442 (2)	0.5089 (14)	0.2103 (9)	0.040 (4)
H11C	0.495951	0.496176	0.162590	0.048*
H11D	0.395726	0.435547	0.224232	0.048*
C12B	0.282 (2)	0.6327 (16)	0.2225 (10)	0.049 (4)
H12D	0.332262	0.705147	0.213715	0.073*
H12E	0.219332	0.639049	0.268695	0.073*
H12F	0.189932	0.635602	0.193100	0.073*
O13B	0.8694 (15)	0.4266 (9)	0.1634 (4)	0.030 (2)
C14B	1.036 (2)	0.3272 (14)	0.1298 (7)	0.035 (3)
H14C	0.997241	0.264028	0.106133	0.042*
H14D	1.116079	0.280608	0.162241	0.042*
C15B	1.146 (3)	0.3913 (18)	0.0819 (10)	0.051 (5)
H15D	1.256681	0.325726	0.057019	0.076*
H15E	1.189278	0.450408	0.106048	0.076*
H15F	1.063975	0.440126	0.051230	0.076*
C16B	0.736 (2)	0.4469 (16)	0.5744 (7)	0.036 (3)
H16D	0.684167	0.375599	0.585012	0.053*
H16E	0.640661	0.528407	0.592605	0.053*
H16F	0.851940	0.432194	0.593624	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1A	0.0344 (5)	0.0278 (4)	0.0367 (5)	−0.0107 (4)	−0.0074 (4)	0.0072 (4)
I2A	0.0430 (6)	0.0349 (5)	0.0403 (5)	−0.0136 (4)	−0.0055 (4)	0.0130 (4)
C1A	0.016 (6)	0.029 (6)	0.025 (6)	−0.008 (5)	−0.005 (5)	0.013 (5)
C2A	0.016 (6)	0.021 (5)	0.028 (6)	−0.005 (5)	−0.005 (5)	0.010 (5)
C3A	0.027 (7)	0.025 (6)	0.031 (6)	−0.007 (5)	−0.007 (5)	−0.006 (5)
C4A	0.025 (7)	0.036 (7)	0.027 (6)	−0.016 (6)	−0.006 (5)	0.001 (6)
C5A	0.032 (8)	0.025 (6)	0.028 (6)	−0.011 (5)	−0.007 (5)	0.015 (5)
C6A	0.025 (6)	0.018 (5)	0.024 (6)	−0.004 (5)	−0.002 (5)	0.006 (5)
C7A	0.024 (6)	0.024 (6)	0.020 (5)	−0.008 (5)	−0.012 (5)	0.003 (5)
P8A	0.0215 (16)	0.0229 (14)	0.0223 (14)	−0.0073 (12)	−0.0043 (12)	0.0062 (12)
O9A	0.026 (5)	0.024 (4)	0.038 (5)	−0.007 (4)	−0.005 (4)	0.008 (4)
O10A	0.019 (4)	0.026 (4)	0.030 (4)	−0.010 (3)	−0.003 (4)	0.004 (4)
C11A	0.025 (7)	0.032 (7)	0.053 (9)	−0.015 (6)	−0.011 (6)	0.015 (6)
C12A	0.041 (9)	0.057 (9)	0.040 (8)	−0.031 (8)	−0.007 (7)	0.013 (7)
O13A	0.040 (6)	0.026 (4)	0.017 (4)	−0.010 (4)	−0.004 (4)	0.004 (4)
C14A	0.034 (8)	0.040 (7)	0.025 (6)	−0.018 (6)	−0.002 (5)	0.002 (6)
C15A	0.056 (11)	0.044 (9)	0.056 (10)	0.001 (8)	−0.031 (9)	−0.007 (8)
C16A	0.026 (7)	0.047 (8)	0.025 (6)	−0.007 (6)	−0.005 (5)	0.005 (6)
I1B	0.0360 (5)	0.0285 (4)	0.0367 (5)	−0.0093 (4)	−0.0080 (4)	0.0068 (4)
I2B	0.0475 (6)	0.0346 (5)	0.0398 (5)	−0.0125 (4)	−0.0172 (4)	0.0130 (4)
C1B	0.024 (7)	0.027 (6)	0.028 (6)	−0.011 (5)	−0.005 (5)	−0.002 (6)
C2B	0.025 (7)	0.025 (6)	0.033 (7)	−0.008 (5)	−0.005 (5)	−0.006 (6)
C3B	0.026 (7)	0.029 (6)	0.027 (6)	−0.008 (5)	−0.009 (5)	0.003 (5)
C4B	0.025 (7)	0.031 (6)	0.031 (6)	−0.019 (6)	−0.008 (5)	0.004 (6)
C5B	0.024 (7)	0.027 (6)	0.028 (6)	−0.017 (5)	−0.009 (5)	0.009 (5)
C6B	0.017 (6)	0.028 (6)	0.033 (6)	−0.008 (5)	−0.007 (5)	0.001 (5)
C7B	0.022 (6)	0.026 (6)	0.030 (6)	−0.008 (5)	−0.005 (5)	0.006 (5)
P8B	0.0235 (17)	0.0233 (14)	0.0260 (15)	−0.0078 (12)	−0.0074 (13)	0.0034 (13)
O9B	0.034 (5)	0.027 (5)	0.033 (5)	−0.014 (4)	−0.011 (4)	0.008 (4)
O10B	0.024 (5)	0.033 (5)	0.037 (5)	−0.009 (4)	−0.009 (4)	0.005 (4)
C11B	0.024 (7)	0.032 (7)	0.070 (10)	−0.009 (6)	−0.021 (7)	0.003 (7)
C12B	0.027 (8)	0.049 (9)	0.073 (11)	−0.014 (7)	−0.017 (8)	0.010 (9)
O13B	0.033 (6)	0.030 (5)	0.025 (4)	−0.007 (4)	−0.001 (4)	0.004 (4)
C14B	0.040 (9)	0.034 (7)	0.026 (6)	−0.006 (6)	−0.003 (6)	0.003 (6)
C15B	0.042 (10)	0.051 (9)	0.059 (10)	−0.023 (8)	0.010 (8)	−0.005 (9)
C16B	0.043 (9)	0.048 (8)	0.024 (6)	−0.025 (7)	−0.008 (6)	−0.001 (6)

Geometric parameters (Å, º) top

I1A—C2A	2.080 (12)	I1B—C2B	2.082 (15)
I2A—C5A	2.064 (13)	I2B—C5B	2.077 (14)
C1A—C2A	1.380 (17)	C1B—C6B	1.38 (2)
C1A—C6A	1.418 (18)	C1B—C2B	1.398 (17)
C1A—C7A	1.487 (16)	C1B—C7B	1.521 (18)
C2A—C3A	1.410 (18)	C2B—C3B	1.382 (19)
C3A—C4A	1.37 (2)	C3B—C4B	1.37 (2)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.400 (18)	C4B—C5B	1.385 (18)
C4A—C16A	1.517 (18)	C4B—C16B	1.510 (19)
C5A—C6A	1.386 (18)	C5B—C6B	1.388 (19)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—P8A	1.799 (13)	C7B—P8B	1.792 (14)
C7A—H7A	0.9900	C7B—H7C	0.9900
C7A—H7B	0.9900	C7B—H7D	0.9900
P8A—O9A	1.471 (9)	P8B—O9B	1.466 (9)
P8A—O10A	1.572 (9)	P8B—O10B	1.558 (10)
P8A—O13A	1.579 (9)	P8B—O13B	1.595 (10)
O10A—C11A	1.462 (17)	O10B—C11B	1.487 (18)
C11A—C12A	1.47 (2)	C11B—C12B	1.49 (2)
C11A—H11A	0.9900	C11B—H11C	0.9900
C11A—H11B	0.9900	C11B—H11D	0.9900
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12B	0.9800	C12B—H12E	0.9800
C12A—H12C	0.9800	C12B—H12F	0.9800
O13A—C14A	1.465 (16)	O13B—C14B	1.450 (17)
C14A—C15A	1.49 (2)	C14B—C15B	1.49 (2)
C14A—H14A	0.9900	C14B—H14C	0.9900
C14A—H14B	0.9900	C14B—H14D	0.9900
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16B	0.9800	C16B—H16E	0.9800
C16A—H16C	0.9800	C16B—H16F	0.9800

C2A—C1A—C6A	116.4 (11)	C6B—C1B—C2B	117.9 (12)
C2A—C1A—C7A	125.6 (12)	C6B—C1B—C7B	118.8 (11)
C6A—C1A—C7A	117.8 (11)	C2B—C1B—C7B	123.4 (13)
C1A—C2A—C3A	121.6 (12)	C3B—C2B—C1B	119.8 (14)
C1A—C2A—I1A	122.2 (9)	C3B—C2B—I1B	117.6 (9)
C3A—C2A—I1A	116.1 (9)	C1B—C2B—I1B	122.6 (10)
C4A—C3A—C2A	121.6 (11)	C4B—C3B—C2B	123.5 (12)
C4A—C3A—H3A	119.2	C4B—C3B—H3B	118.2
C2A—C3A—H3A	119.2	C2B—C3B—H3B	118.2
C3A—C4A—C5A	117.6 (12)	C3B—C4B—C5B	115.7 (12)
C3A—C4A—C16A	119.8 (12)	C3B—C4B—C16B	121.7 (12)
C5A—C4A—C16A	122.6 (13)	C5B—C4B—C16B	122.6 (13)
C6A—C5A—C4A	121.2 (12)	C4B—C5B—C6B	122.8 (13)
C6A—C5A—I2A	118.2 (9)	C4B—C5B—I2B	120.1 (9)
C4A—C5A—I2A	120.6 (10)	C6B—C5B—I2B	117.1 (9)
C5A—C6A—C1A	121.6 (11)	C1B—C6B—C5B	120.4 (12)
C5A—C6A—H6A	119.2	C1B—C6B—H6B	119.8
C1A—C6A—H6A	119.2	C5B—C6B—H6B	119.8
C1A—C7A—P8A	114.5 (9)	C1B—C7B—P8B	114.7 (10)
C1A—C7A—H7A	108.6	C1B—C7B—H7C	108.6
P8A—C7A—H7A	108.6	P8B—C7B—H7C	108.6
C1A—C7A—H7B	108.6	C1B—C7B—H7D	108.6
P8A—C7A—H7B	108.6	P8B—C7B—H7D	108.6
H7A—C7A—H7B	107.6	H7C—C7B—H7D	107.6
O9A—P8A—O10A	116.1 (6)	O9B—P8B—O10B	116.8 (6)
O9A—P8A—O13A	113.4 (5)	O9B—P8B—O13B	114.2 (5)
O10A—P8A—O13A	102.7 (5)	O10B—P8B—O13B	101.9 (6)
O9A—P8A—C7A	115.6 (6)	O9B—P8B—C7B	114.9 (6)
O10A—P8A—C7A	102.7 (5)	O10B—P8B—C7B	102.5 (6)
O13A—P8A—C7A	104.8 (6)	O13B—P8B—C7B	104.8 (6)
C11A—O10A—P8A	123.0 (8)	C11B—O10B—P8B	120.1 (8)
O10A—C11A—C12A	110.5 (13)	C12B—C11B—O10B	107.8 (12)
O10A—C11A—H11A	109.6	C12B—C11B—H11C	110.1
C12A—C11A—H11A	109.6	O10B—C11B—H11C	110.1
O10A—C11A—H11B	109.6	C12B—C11B—H11D	110.1
C12A—C11A—H11B	109.6	O10B—C11B—H11D	110.1
H11A—C11A—H11B	108.1	H11C—C11B—H11D	108.5
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C14A—O13A—P8A	119.4 (9)	C14B—O13B—P8B	118.9 (9)
O13A—C14A—C15A	108.4 (13)	O13B—C14B—C15B	107.8 (12)
O13A—C14A—H14A	110.0	O13B—C14B—H14C	110.2
C15A—C14A—H14A	110.0	C15B—C14B—H14C	110.2
O13A—C14A—H14B	110.0	O13B—C14B—H14D	110.2
C15A—C14A—H14B	110.0	C15B—C14B—H14D	110.2
H14A—C14A—H14B	108.4	H14C—C14B—H14D	108.5
C14A—C15A—H15A	109.5	C14B—C15B—H15D	109.5
C14A—C15A—H15B	109.5	C14B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C14A—C15A—H15C	109.5	C14B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C4A—C16A—H16A	109.5	C4B—C16B—H16D	109.5
C4A—C16A—H16B	109.5	C4B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C4A—C16A—H16C	109.5	C4B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5

C6A—C1A—C2A—C3A	−2.4 (19)	C6B—C1B—C2B—C3B	1 (2)
C7A—C1A—C2A—C3A	−178.4 (13)	C7B—C1B—C2B—C3B	−178.3 (13)
C6A—C1A—C2A—I1A	179.0 (10)	C6B—C1B—C2B—I1B	179.4 (10)
C7A—C1A—C2A—I1A	3.0 (18)	C7B—C1B—C2B—I1B	0.2 (19)
C1A—C2A—C3A—C4A	3 (2)	C1B—C2B—C3B—C4B	−1 (2)
I1A—C2A—C3A—C4A	−177.9 (11)	I1B—C2B—C3B—C4B	−179.1 (11)
C2A—C3A—C4A—C5A	−3 (2)	C2B—C3B—C4B—C5B	0 (2)
C2A—C3A—C4A—C16A	178.6 (13)	C2B—C3B—C4B—C16B	179.9 (14)
C3A—C4A—C5A—C6A	2 (2)	C3B—C4B—C5B—C6B	−1 (2)
C16A—C4A—C5A—C6A	−179.6 (14)	C16B—C4B—C5B—C6B	179.8 (13)
C3A—C4A—C5A—I2A	178.7 (11)	C3B—C4B—C5B—I2B	178.6 (10)
C16A—C4A—C5A—I2A	−3.0 (19)	C16B—C4B—C5B—I2B	−0.9 (18)
C4A—C5A—C6A—C1A	−1 (2)	C2B—C1B—C6B—C5B	−1 (2)
I2A—C5A—C6A—C1A	−178.0 (10)	C7B—C1B—C6B—C5B	178.0 (12)
C2A—C1A—C6A—C5A	1 (2)	C4B—C5B—C6B—C1B	1 (2)
C7A—C1A—C6A—C5A	177.7 (13)	I2B—C5B—C6B—C1B	−178.2 (10)
C2A—C1A—C7A—P8A	−104.0 (13)	C6B—C1B—C7B—P8B	79.6 (14)
C6A—C1A—C7A—P8A	80.1 (14)	C2B—C1B—C7B—P8B	−101.3 (14)
C1A—C7A—P8A—O9A	−56.9 (11)	C1B—C7B—P8B—O9B	−55.2 (11)
C1A—C7A—P8A—O10A	70.5 (10)	C1B—C7B—P8B—O10B	72.5 (11)
C1A—C7A—P8A—O13A	177.4 (9)	C1B—C7B—P8B—O13B	178.6 (9)
O9A—P8A—O10A—C11A	−39.4 (12)	O9B—P8B—O10B—C11B	−62.1 (12)
O13A—P8A—O10A—C11A	84.9 (11)	O13B—P8B—O10B—C11B	63.0 (12)
C7A—P8A—O10A—C11A	−166.5 (10)	C7B—P8B—O10B—C11B	171.3 (11)
P8A—O10A—C11A—C12A	−91.8 (13)	P8B—O10B—C11B—C12B	−170.5 (12)
O9A—P8A—O13A—C14A	−42.8 (12)	O9B—P8B—O13B—C14B	−40.2 (13)
O10A—P8A—O13A—C14A	−168.8 (10)	O10B—P8B—O13B—C14B	−167.0 (11)
C7A—P8A—O13A—C14A	84.3 (11)	C7B—P8B—O13B—C14B	86.4 (11)
P8A—O13A—C14A—C15A	−157.0 (12)	P8B—O13B—C14B—C15B	−147.0 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A···O9B	0.99	2.36	3.275 (15)	154
C11A—H11B···O9Bⁱ	0.99	2.44	3.377 (17)	158
C14A—H14B···O9B	0.99	2.42	3.407 (18)	172
C7B—H7C···O9Aⁱⁱ	0.99	2.48	3.388 (15)	152
C11B—H11D···O9A	0.99	2.60	3.575 (18)	169
C14B—H14D···O9Aⁱⁱ	0.99	2.36	3.324 (19)	166

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

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