1D-3,4-Di-O-(di­phenyl­methylphos­pho­nio)-1,2,5,6-tetra-O-methyl-chiro-inositol diiodide

The title compound, 3,4,5,6-tetra­methoxy­cyclo­hexane-1,2-diyl­dioxy­bis­(methyl­di­phenyl­phospho­nium) diiodide, C₃₆­H₄₄­O₆­P₂²⁺·­2I^-, was prepared from a New Zealand natural product, D-chiro-inositol, in order to develop new catalytic metal complexes. The inositol ring retains its usual chair conformation with only minor perturbations caused by the bound di­phenyl­methyl­phosphines. Crystal-packing forces are provided by C-H...I cation-anion interactions.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996) and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999), ORTEP-3 (Farrugia, 1997) based on ORTEPII (Johnson, 1976).

(I)

Crystal data

C36H44O6P2^2+·2I^−	Dx = 1.534 Mg m^−3
Mr = 888.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8192 reflections
a = 10.306 (3) Å	θ = 2.6–27.5°
b = 12.953 (4) Å	µ = 1.76 mm^−1
c = 28.826 (9) Å	T = 163 K
V = 3848 (2) Å^3	Block, colourless
Z = 4	0.25 × 0.23 × 0.16 mm
F(000) = 1776

Data collection

CCD area detector diffractometer	8629 independent reflections
Radiation source: fine-focus sealed tube	7920 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.192 pixels mm^-1	θmax = 27.9°, θmin = 2.1°
phi and ω scans	h = −8→13
Absorption correction: multi-scan (Blessing, 1995)	k = −16→16
Tmin = 0.647, Tmax = 0.755	l = −36→37
51053 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.051	w = 1/[σ^2(Fo^2) + (0.0295P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
8629 reflections	Δρmax = 0.80 e Å^−3
415 parameters	Δρmin = −0.55 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.009 (10)

Special details

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	0.895228 (17)	0.464739 (14)	0.996533 (6)	0.02801 (5)
I2	0.266148 (18)	0.492371 (13)	0.756443 (6)	0.03257 (5)
P1	0.95141 (7)	0.65523 (5)	0.85405 (2)	0.02222 (14)
P2	1.18966 (7)	0.29144 (5)	0.90589 (2)	0.02139 (14)
O1	0.95197 (17)	0.53972 (14)	0.87088 (6)	0.0237 (4)
O2	1.09757 (18)	0.36453 (13)	0.87691 (6)	0.0230 (4)
O3	0.97514 (19)	0.17180 (14)	0.86722 (6)	0.0272 (4)
O4	0.7128 (2)	0.24993 (15)	0.88158 (7)	0.0329 (5)
O5	0.7783 (2)	0.35807 (16)	0.76729 (7)	0.0379 (5)
O6	0.72620 (17)	0.53935 (14)	0.81902 (6)	0.0277 (4)
C1	0.9130 (2)	0.44944 (19)	0.84421 (9)	0.0228 (5)
H1	0.9537	0.4510	0.8127	0.027*
C2	0.9585 (2)	0.3543 (2)	0.87104 (9)	0.0208 (5)
H2	0.9151	0.3519	0.9021	0.025*
C3	0.9227 (3)	0.2577 (2)	0.84278 (9)	0.0243 (6)
H3	0.9638	0.2621	0.8114	0.029*
C4	0.7757 (3)	0.2526 (2)	0.83745 (9)	0.0277 (6)
H4	0.7515	0.1899	0.8192	0.033*
C5	0.7254 (3)	0.3495 (2)	0.81278 (9)	0.0306 (6)
H5	0.6286	0.3468	0.8109	0.037*
C6	0.7666 (3)	0.44507 (19)	0.84010 (9)	0.0245 (5)
H6	0.7285	0.4410	0.8720	0.029*
C10	0.9680 (3)	0.6669 (2)	0.79251 (9)	0.0312 (6)
H10A	1.0428	0.6263	0.7821	0.037*
H10B	0.9810	0.7396	0.7843	0.037*
H10C	0.8892	0.6412	0.7774	0.037*
C20	1.1142 (3)	0.2289 (2)	0.95374 (8)	0.0269 (6)
H20A	1.0684	0.2802	0.9726	0.032*
H20B	1.1804	0.1946	0.9727	0.032*
H20C	1.0521	0.1775	0.9423	0.032*
C31	0.9915 (3)	0.0811 (2)	0.83915 (12)	0.0406 (8)
H31A	1.0279	0.0253	0.8581	0.053*
H31B	1.0506	0.0964	0.8134	0.053*
H31C	0.9071	0.0596	0.8268	0.053*
C41	0.6870 (4)	0.1491 (3)	0.89990 (14)	0.0522 (10)
H41A	0.6453	0.1556	0.9303	0.068*
H41B	0.7688	0.1112	0.9032	0.068*
H41C	0.6294	0.1117	0.8787	0.068*
C51	0.6993 (4)	0.3109 (3)	0.73230 (11)	0.0532 (10)
H51A	0.7403	0.3199	0.7019	0.069*
H51B	0.6134	0.3434	0.7321	0.069*
H51C	0.6901	0.2370	0.7390	0.069*
C61	0.5942 (3)	0.5642 (2)	0.82917 (11)	0.0372 (7)
H61A	0.5708	0.6289	0.8137	0.048*
H61B	0.5835	0.5721	0.8628	0.048*
H61C	0.5377	0.5086	0.8180	0.048*
C111	1.0912 (3)	0.7082 (2)	0.88201 (9)	0.0246 (6)
C112	1.0845 (3)	0.7991 (2)	0.90796 (11)	0.0366 (7)
H112	1.0042	0.8345	0.9111	0.044*
C113	1.1942 (3)	0.8373 (3)	0.92887 (12)	0.0450 (8)
H113	1.1899	0.8995	0.9462	0.054*
C114	1.3097 (3)	0.7861 (3)	0.92477 (12)	0.0444 (8)
H114	1.3846	0.8116	0.9402	0.053*
C115	1.3180 (3)	0.6974 (3)	0.89831 (13)	0.0465 (9)
H115	1.3990	0.6631	0.8951	0.056*
C116	1.2088 (3)	0.6581 (2)	0.87634 (11)	0.0368 (7)
H116	1.2147	0.5978	0.8577	0.044*
C121	0.8156 (3)	0.7258 (2)	0.87562 (9)	0.0233 (6)
C122	0.7643 (3)	0.8066 (2)	0.84944 (10)	0.0300 (6)
H122	0.7908	0.8160	0.8182	0.036*
C123	0.6749 (3)	0.8726 (2)	0.86906 (11)	0.0360 (7)
H123	0.6404	0.9281	0.8514	0.043*
C124	0.6352 (3)	0.8577 (2)	0.91474 (11)	0.0357 (7)
H124	0.5746	0.9038	0.9284	0.043*
C125	0.6842 (3)	0.7754 (2)	0.94034 (11)	0.0360 (7)
H125	0.6551	0.7648	0.9712	0.043*
C126	0.7742 (3)	0.7093 (2)	0.92144 (9)	0.0301 (6)
H126	0.8078	0.6534	0.9391	0.036*
C211	1.2674 (3)	0.2035 (2)	0.86730 (9)	0.0245 (5)
C212	1.2999 (3)	0.2409 (2)	0.82289 (10)	0.0399 (8)
H212	1.2787	0.3095	0.8141	0.048*
C213	1.3633 (4)	0.1758 (3)	0.79233 (11)	0.0513 (10)
H213	1.3863	0.2001	0.7624	0.062*
C214	1.3937 (3)	0.0745 (3)	0.80511 (11)	0.0466 (8)
H214	1.4372	0.0303	0.7839	0.056*
C215	1.3605 (3)	0.0394 (2)	0.84817 (10)	0.0388 (7)
H215	1.3813	−0.0296	0.8566	0.047*
C216	1.2970 (3)	0.1025 (2)	0.88008 (9)	0.0305 (6)
H216	1.2743	0.0772	0.9099	0.037*
C221	1.3098 (3)	0.3760 (2)	0.93001 (9)	0.0251 (6)
C222	1.4404 (3)	0.3571 (2)	0.92423 (9)	0.0298 (6)
H222	1.4685	0.3032	0.9042	0.036*
C223	1.5301 (3)	0.4164 (2)	0.94754 (10)	0.0352 (7)
H223	1.6201	0.4029	0.9436	0.042*
C224	1.4914 (3)	0.4942 (3)	0.97617 (10)	0.0423 (8)
H224	1.5545	0.5345	0.9920	0.051*
C225	1.3614 (3)	0.5148 (3)	0.98232 (12)	0.0491 (9)
H225	1.3349	0.5693	1.0022	0.059*
C226	1.2692 (3)	0.4558 (2)	0.95945 (11)	0.0397 (7)
H226	1.1794	0.4693	0.9637	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02670 (8)	0.03420 (10)	0.02314 (8)	0.00227 (7)	0.00374 (7)	−0.00260 (7)
I2	0.03763 (10)	0.03190 (10)	0.02819 (9)	0.00301 (8)	−0.00024 (7)	0.00211 (7)
P1	0.0237 (4)	0.0222 (3)	0.0207 (3)	0.0025 (3)	0.0001 (3)	0.0000 (3)
P2	0.0208 (3)	0.0232 (3)	0.0202 (3)	0.0038 (3)	−0.0006 (3)	−0.0003 (3)
O1	0.0275 (9)	0.0198 (9)	0.0238 (9)	0.0014 (8)	−0.0040 (7)	−0.0014 (7)
O2	0.0201 (9)	0.0240 (10)	0.0248 (9)	0.0017 (8)	−0.0037 (8)	0.0006 (7)
O3	0.0293 (11)	0.0227 (10)	0.0296 (10)	0.0019 (8)	−0.0063 (8)	−0.0029 (8)
O4	0.0304 (11)	0.0305 (11)	0.0376 (12)	−0.0064 (9)	0.0027 (9)	0.0004 (9)
O5	0.0481 (13)	0.0398 (11)	0.0257 (10)	−0.0005 (10)	−0.0113 (9)	−0.0047 (8)
O6	0.0240 (9)	0.0274 (9)	0.0317 (9)	0.0064 (8)	−0.0046 (8)	0.0022 (8)
C1	0.0223 (13)	0.0225 (13)	0.0236 (12)	−0.0014 (10)	−0.0039 (10)	−0.0053 (10)
C2	0.0173 (12)	0.0230 (13)	0.0221 (13)	0.0013 (10)	−0.0031 (10)	−0.0016 (10)
C3	0.0271 (16)	0.0212 (13)	0.0246 (13)	0.0036 (11)	−0.0033 (11)	−0.0024 (11)
C4	0.0281 (14)	0.0259 (14)	0.0291 (14)	−0.0022 (12)	−0.0058 (12)	−0.0056 (11)
C5	0.0284 (15)	0.0309 (15)	0.0325 (15)	−0.0017 (12)	−0.0078 (12)	−0.0050 (12)
C6	0.0228 (13)	0.0250 (14)	0.0255 (13)	0.0041 (11)	−0.0024 (10)	−0.0012 (10)
C10	0.0344 (16)	0.0380 (17)	0.0212 (13)	0.0040 (13)	0.0036 (12)	0.0020 (12)
C20	0.0315 (15)	0.0313 (14)	0.0180 (12)	0.0020 (12)	0.0014 (11)	0.0028 (10)
C31	0.0457 (19)	0.0220 (15)	0.054 (2)	0.0057 (14)	−0.0156 (16)	−0.0078 (14)
C41	0.048 (2)	0.0391 (19)	0.069 (3)	−0.0022 (17)	0.0160 (19)	0.0140 (18)
C51	0.080 (3)	0.0404 (19)	0.0392 (19)	0.0116 (18)	−0.0310 (18)	−0.0115 (15)
C61	0.0233 (15)	0.0404 (18)	0.0480 (18)	0.0108 (13)	−0.0056 (13)	0.0014 (13)
C111	0.0239 (14)	0.0237 (14)	0.0263 (14)	−0.0030 (11)	0.0006 (12)	0.0006 (11)
C112	0.0267 (16)	0.0354 (17)	0.0477 (18)	−0.0040 (13)	0.0028 (14)	−0.0079 (14)
C113	0.0402 (19)	0.0441 (19)	0.051 (2)	−0.0126 (15)	0.0094 (15)	−0.0225 (16)
C114	0.0307 (17)	0.056 (2)	0.047 (2)	−0.0151 (15)	0.0033 (15)	−0.0107 (17)
C115	0.0239 (16)	0.057 (2)	0.059 (2)	0.0009 (15)	0.0021 (15)	−0.0150 (18)
C116	0.0307 (17)	0.0387 (17)	0.0411 (18)	0.0029 (14)	−0.0013 (14)	−0.0139 (14)
C121	0.0201 (13)	0.0230 (13)	0.0269 (14)	0.0017 (10)	0.0030 (11)	−0.0020 (11)
C122	0.0276 (15)	0.0293 (15)	0.0331 (15)	0.0045 (12)	0.0014 (12)	0.0048 (11)
C123	0.0311 (16)	0.0255 (16)	0.051 (2)	0.0039 (12)	0.0032 (14)	0.0032 (14)
C124	0.0277 (17)	0.0297 (16)	0.0498 (19)	−0.0007 (12)	0.0066 (13)	−0.0117 (14)
C125	0.0364 (17)	0.0371 (17)	0.0344 (16)	−0.0070 (14)	0.0065 (13)	−0.0045 (13)
C126	0.0303 (15)	0.0328 (15)	0.0272 (14)	0.0016 (13)	0.0002 (12)	0.0016 (11)
C211	0.0246 (13)	0.0267 (14)	0.0223 (13)	0.0040 (12)	0.0018 (11)	−0.0043 (10)
C212	0.058 (2)	0.0289 (16)	0.0330 (16)	0.0017 (15)	0.0093 (15)	0.0025 (13)
C213	0.075 (3)	0.049 (2)	0.0305 (17)	−0.0009 (18)	0.0240 (17)	−0.0037 (15)
C214	0.051 (2)	0.0430 (19)	0.0462 (19)	0.0079 (17)	0.0151 (17)	−0.0117 (15)
C215	0.0406 (18)	0.0325 (16)	0.0434 (17)	0.0129 (13)	−0.0028 (13)	−0.0055 (14)
C216	0.0333 (16)	0.0341 (16)	0.0239 (14)	0.0079 (13)	−0.0021 (12)	−0.0009 (11)
C221	0.0230 (14)	0.0291 (15)	0.0234 (14)	0.0015 (11)	−0.0057 (11)	0.0013 (11)
C222	0.0219 (14)	0.0403 (17)	0.0273 (14)	0.0024 (12)	0.0002 (11)	−0.0024 (12)
C223	0.0252 (15)	0.0508 (19)	0.0295 (15)	0.0005 (14)	−0.0028 (12)	0.0054 (14)
C224	0.0343 (16)	0.054 (2)	0.0384 (16)	−0.0119 (15)	−0.0123 (13)	−0.0057 (16)
C225	0.0423 (19)	0.048 (2)	0.057 (2)	−0.0026 (15)	−0.0061 (15)	−0.0256 (17)
C226	0.0273 (15)	0.0426 (17)	0.0493 (18)	0.0033 (14)	−0.0046 (13)	−0.0191 (15)

Geometric parameters (Å, º)

P1—O1	1.573 (2)	C61—H61B	0.9800
P1—C121	1.784 (3)	C61—H61C	0.9800
P1—C111	1.788 (3)	C111—C116	1.384 (4)
P1—C10	1.788 (3)	C111—C112	1.397 (4)
P2—O2	1.5796 (18)	C112—C113	1.373 (4)
P2—C20	1.779 (3)	C112—H112	0.9500
P2—C211	1.783 (3)	C113—C114	1.368 (5)
P2—C221	1.794 (3)	C113—H113	0.9500
O1—C1	1.456 (3)	C114—C115	1.381 (5)
O2—C2	1.449 (3)	C114—H114	0.9500
O3—C3	1.424 (3)	C115—C116	1.388 (4)
O3—C31	1.437 (3)	C115—H115	0.9500
O4—C4	1.428 (3)	C116—H116	0.9500
O4—C41	1.433 (4)	C121—C122	1.394 (4)
O5—C5	1.425 (3)	C121—C126	1.405 (4)
O5—C51	1.433 (4)	C122—C123	1.378 (4)
O6—C6	1.426 (3)	C122—H122	0.9500
O6—C61	1.428 (3)	C123—C124	1.392 (4)
C1—C6	1.514 (4)	C123—H123	0.9500
C1—C2	1.528 (3)	C124—C125	1.391 (4)
C1—H1	1.0000	C124—H124	0.9500
C2—C3	1.538 (4)	C125—C126	1.375 (4)
C2—H2	1.0000	C125—H125	0.9500
C3—C4	1.525 (4)	C126—H126	0.9500
C3—H3	1.0000	C211—C216	1.392 (4)
C4—C5	1.532 (4)	C211—C212	1.409 (4)
C4—H4	1.0000	C212—C213	1.383 (4)
C5—C6	1.527 (4)	C212—H212	0.9500
C5—H5	1.0000	C213—C214	1.398 (5)
C6—H6	1.0000	C213—H213	0.9500
C10—H10A	0.9800	C214—C215	1.365 (4)
C10—H10B	0.9800	C214—H214	0.9500
C10—H10C	0.9800	C215—C216	1.394 (4)
C20—H20A	0.9800	C215—H215	0.9500
C20—H20B	0.9800	C216—H216	0.9500
C20—H20C	0.9800	C221—C222	1.378 (4)
C31—H31A	0.9800	C221—C226	1.401 (4)
C31—H31B	0.9800	C222—C223	1.377 (4)
C31—H31C	0.9800	C222—H222	0.9500
C41—H41A	0.9800	C223—C224	1.362 (4)
C41—H41B	0.9800	C223—H223	0.9500
C41—H41C	0.9800	C224—C225	1.378 (4)
C51—H51A	0.9800	C224—H224	0.9500
C51—H51B	0.9800	C225—C226	1.386 (4)
C51—H51C	0.9800	C225—H225	0.9500
C61—H61A	0.9800	C226—H226	0.9500
O1—P1—C121	112.52 (12)	O5—C51—H51C	109.5
O1—P1—C111	102.88 (11)	H51A—C51—H51C	109.5
C121—P1—C111	106.18 (13)	H51B—C51—H51C	109.5
O1—P1—C10	112.71 (12)	O6—C61—H61A	109.5
C121—P1—C10	112.16 (13)	O6—C61—H61B	109.5
C111—P1—C10	109.75 (14)	H61A—C61—H61B	109.5
O2—P2—C20	114.85 (12)	O6—C61—H61C	109.5
O2—P2—C211	108.86 (11)	H61A—C61—H61C	109.5
C20—P2—C211	112.92 (13)	H61B—C61—H61C	109.5
O2—P2—C221	104.70 (11)	C116—C111—C112	120.1 (3)
C20—P2—C221	106.23 (13)	C116—C111—P1	118.2 (2)
C211—P2—C221	108.78 (13)	C112—C111—P1	121.7 (2)
C1—O1—P1	126.88 (15)	C113—C112—C111	119.9 (3)
C2—O2—P2	126.96 (16)	C113—C112—H112	120.1
C3—O3—C31	113.9 (2)	C111—C112—H112	120.1
C4—O4—C41	115.8 (2)	C114—C113—C112	120.2 (3)
C5—O5—C51	113.4 (3)	C114—C113—H113	119.9
C6—O6—C61	112.6 (2)	C112—C113—H113	119.9
O1—C1—C6	110.3 (2)	C113—C114—C115	120.4 (3)
O1—C1—C2	107.19 (19)	C113—C114—H114	119.8
C6—C1—C2	108.4 (2)	C115—C114—H114	119.8
O1—C1—H1	110.3	C114—C115—C116	120.4 (3)
C6—C1—H1	110.3	C114—C115—H115	119.8
C2—C1—H1	110.3	C116—C115—H115	119.8
O2—C2—C1	106.8 (2)	C111—C116—C115	119.0 (3)
O2—C2—C3	111.9 (2)	C111—C116—H116	120.5
C1—C2—C3	108.3 (2)	C115—C116—H116	120.5
O2—C2—H2	109.9	C122—C121—C126	120.5 (3)
C1—C2—H2	109.9	C122—C121—P1	119.6 (2)
C3—C2—H2	109.9	C126—C121—P1	119.2 (2)
O3—C3—C4	113.2 (2)	C123—C122—C121	119.8 (3)
O3—C3—C2	106.4 (2)	C123—C122—H122	120.1
C4—C3—C2	109.1 (2)	C121—C122—H122	120.1
O3—C3—H3	109.4	C122—C123—C124	119.9 (3)
C4—C3—H3	109.4	C122—C123—H123	120.0
C2—C3—H3	109.4	C124—C123—H123	120.0
O4—C4—C3	111.2 (2)	C125—C124—C123	120.1 (3)
O4—C4—C5	106.3 (2)	C125—C124—H124	120.0
C3—C4—C5	110.3 (2)	C123—C124—H124	120.0
O4—C4—H4	109.6	C126—C125—C124	120.8 (3)
C3—C4—H4	109.6	C126—C125—H125	119.6
C5—C4—H4	109.6	C124—C125—H125	119.6
O5—C5—C6	107.8 (2)	C125—C126—C121	118.9 (3)
O5—C5—C4	111.2 (2)	C125—C126—H126	120.6
C6—C5—C4	109.3 (2)	C121—C126—H126	120.6
O5—C5—H5	109.5	C216—C211—C212	120.8 (3)
C6—C5—H5	109.5	C216—C211—P2	122.3 (2)
C4—C5—H5	109.5	C212—C211—P2	117.0 (2)
O6—C6—C1	107.0 (2)	C213—C212—C211	118.8 (3)
O6—C6—C5	113.1 (2)	C213—C212—H212	120.6
C1—C6—C5	110.4 (2)	C211—C212—H212	120.6
O6—C6—H6	108.8	C212—C213—C214	120.7 (3)
C1—C6—H6	108.8	C212—C213—H213	119.7
C5—C6—H6	108.8	C214—C213—H213	119.7
P1—C10—H10A	109.5	C215—C214—C213	119.7 (3)
P1—C10—H10B	109.5	C215—C214—H214	120.1
H10A—C10—H10B	109.5	C213—C214—H214	120.1
P1—C10—H10C	109.5	C214—C215—C216	121.5 (3)
H10A—C10—H10C	109.5	C214—C215—H215	119.3
H10B—C10—H10C	109.5	C216—C215—H215	119.3
P2—C20—H20A	109.5	C211—C216—C215	118.6 (3)
P2—C20—H20B	109.5	C211—C216—H216	120.7
H20A—C20—H20B	109.5	C215—C216—H216	120.7
P2—C20—H20C	109.5	C222—C221—C226	119.8 (3)
H20A—C20—H20C	109.5	C222—C221—P2	121.2 (2)
H20B—C20—H20C	109.5	C226—C221—P2	118.6 (2)
O3—C31—H31A	109.5	C223—C222—C221	119.8 (3)
O3—C31—H31B	109.5	C223—C222—H222	120.1
H31A—C31—H31B	109.5	C221—C222—H222	120.1
O3—C31—H31C	109.5	C224—C223—C222	120.8 (3)
H31A—C31—H31C	109.5	C224—C223—H223	119.6
H31B—C31—H31C	109.5	C222—C223—H223	119.6
O4—C41—H41A	109.5	C223—C224—C225	120.4 (3)
O4—C41—H41B	109.5	C223—C224—H224	119.8
H41A—C41—H41B	109.5	C225—C224—H224	119.8
O4—C41—H41C	109.5	C224—C225—C226	119.9 (3)
H41A—C41—H41C	109.5	C224—C225—H225	120.0
H41B—C41—H41C	109.5	C226—C225—H225	120.0
O5—C51—H51A	109.5	C225—C226—C221	119.3 (3)
O5—C51—H51B	109.5	C225—C226—H226	120.3
H51A—C51—H51B	109.5	C221—C226—H226	120.3
C121—P1—O1—C1	101.7 (2)	P1—C111—C112—C113	−180.0 (2)
C111—P1—O1—C1	−144.5 (2)	C111—C112—C113—C114	−0.7 (5)
C10—P1—O1—C1	−26.4 (2)	C112—C113—C114—C115	2.2 (5)
C20—P2—O2—C2	−28.6 (2)	C113—C114—C115—C116	−1.3 (6)
C211—P2—O2—C2	99.1 (2)	C112—C111—C116—C115	2.6 (5)
C221—P2—O2—C2	−144.7 (2)	P1—C111—C116—C115	−179.1 (3)
P1—O1—C1—C6	−74.6 (3)	C114—C115—C116—C111	−1.1 (5)
P1—O1—C1—C2	167.71 (17)	O1—P1—C121—C122	−149.6 (2)
P2—O2—C2—C1	174.48 (15)	C111—P1—C121—C122	98.6 (2)
P2—O2—C2—C3	−67.2 (3)	C10—P1—C121—C122	−21.3 (3)
O1—C1—C2—O2	−57.4 (2)	O1—P1—C121—C126	39.6 (3)
C6—C1—C2—O2	−176.35 (19)	C111—P1—C121—C126	−72.2 (3)
O1—C1—C2—C3	−178.0 (2)	C10—P1—C121—C126	168.0 (2)
C6—C1—C2—C3	63.0 (3)	C126—C121—C122—C123	1.9 (4)
C31—O3—C3—C4	80.8 (3)	P1—C121—C122—C123	−168.8 (2)
C31—O3—C3—C2	−159.5 (2)	C121—C122—C123—C124	−0.7 (5)
O2—C2—C3—O3	58.3 (3)	C122—C123—C124—C125	−1.0 (5)
C1—C2—C3—O3	175.8 (2)	C123—C124—C125—C126	1.5 (5)
O2—C2—C3—C4	−179.3 (2)	C124—C125—C126—C121	−0.4 (5)
C1—C2—C3—C4	−61.8 (3)	C122—C121—C126—C125	−1.3 (4)
C41—O4—C4—C3	−92.0 (3)	P1—C121—C126—C125	169.3 (2)
C41—O4—C4—C5	147.9 (3)	O2—P2—C211—C216	−145.8 (2)
O3—C3—C4—O4	59.8 (3)	C20—P2—C211—C216	−17.0 (3)
C2—C3—C4—O4	−58.4 (3)	C221—P2—C211—C216	100.7 (3)
O3—C3—C4—C5	177.5 (2)	O2—P2—C211—C212	35.0 (3)
C2—C3—C4—C5	59.3 (3)	C20—P2—C211—C212	163.8 (2)
C51—O5—C5—C6	−148.5 (2)	C221—P2—C211—C212	−78.5 (3)
C51—O5—C5—C4	91.7 (3)	C216—C211—C212—C213	−0.8 (5)
O4—C4—C5—O5	−177.8 (2)	P2—C211—C212—C213	178.4 (3)
C3—C4—C5—O5	61.5 (3)	C211—C212—C213—C214	0.5 (6)
O4—C4—C5—C6	63.4 (3)	C212—C213—C214—C215	0.0 (6)
C3—C4—C5—C6	−57.3 (3)	C213—C214—C215—C216	−0.2 (5)
C61—O6—C6—C1	−156.9 (2)	C212—C211—C216—C215	0.6 (4)
C61—O6—C6—C5	81.3 (3)	P2—C211—C216—C215	−178.6 (2)
O1—C1—C6—O6	57.4 (2)	C214—C215—C216—C211	−0.1 (5)
C2—C1—C6—O6	174.43 (19)	O2—P2—C221—C222	−127.0 (2)
O1—C1—C6—C5	−179.1 (2)	C20—P2—C221—C222	111.0 (2)
C2—C1—C6—C5	−62.1 (3)	C211—P2—C221—C222	−10.8 (3)
O5—C5—C6—O6	57.8 (3)	O2—P2—C221—C226	60.1 (3)
C4—C5—C6—O6	178.7 (2)	C20—P2—C221—C226	−61.8 (3)
O5—C5—C6—C1	−62.1 (3)	C211—P2—C221—C226	176.4 (2)
C4—C5—C6—C1	58.9 (3)	C226—C221—C222—C223	0.2 (4)
O1—P1—C111—C116	52.9 (3)	P2—C221—C222—C223	−172.6 (2)
C121—P1—C111—C116	171.3 (2)	C221—C222—C223—C224	−0.3 (4)
C10—P1—C111—C116	−67.3 (3)	C222—C223—C224—C225	0.1 (5)
O1—P1—C111—C112	−128.8 (2)	C223—C224—C225—C226	0.3 (5)
C121—P1—C111—C112	−10.4 (3)	C224—C225—C226—C221	−0.4 (5)
C10—P1—C111—C112	111.0 (2)	C222—C221—C226—C225	0.2 (5)
C116—C111—C112—C113	−1.7 (5)	P2—C221—C226—C225	173.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···I2^i	0.98	2.98	3.954 (3)	176
C212—H212···I2^i	0.95	2.90	3.795 (3)	158
C216—H216···I1^ii	0.95	3.02	3.799 (3)	140

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