1,1,1-Tris[(diphenyl­phosphor­yl)­methyl]propane monohydrate

The arrangement of phosphoryl groups and phenyl rings in the title compound, C₂H₅C[CH₂P(O)Ph₂]₃·H₂O or C₄₂H₄₁O₃P₃·H₂O, is far from threefold symmetry. The P=O bond lengths are 1.4899 (12), 1.4926 (12) and 1.4927 (12) Å. The O=P-C(methyl­ene) angles differ significantly from ideal tetra­hedral values, the maximum value being 117.08 (7)°. The C-C-C angles around the central C atom vary from 107.92 (12) to 111.91 (12)°. In the crystal structure, hydrogen bonds in which water mol­ecules act as proton donors link organic mol­ecules into chains along the [100] direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.068
• Data-to-parameter ratio = 23.2

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.99
           From the CIF: _reflns_number_total              10441
           Count of symmetry unique reflns         5247
           Completeness (_total/calc)            198.99%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      5194
           Fraction of Friedel pairs measured     0.990
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Organophosphorus ligands with three phosphoryl groups are considered as promising agents to ensure selectivity of separation of metal mixtures by extraction (Pisareva et al., 2005).

The arrangement of phosphoryl groups and phenyl rings in the title compound, (I, Fig. 1), is far from a threefold symmetry. Selected bond lengths and angles in (I) are given in Table 1. The P═O distances range from 1.4899 (12) to 1.4927 (12) Å. The O═P—C angles with C atoms of CH₂ groups differ significantly from ideal tetrahedral values, the maximum value being 117.08 (7)° (Table 1). The C—C—C angles around the central atom C1 vary from 107.92 (12) to 111.91 (12)°.

The same behaviour of the O═P—C angles can be found in Ln nitrate complexes with CH₃C[CH₂P(O)Ph₂] (Lees & Platt, 2005). The P═O distances in these complexes are slightly longer due to coordination of phosphoryl groups to Ln atoms [from 1.499 (3) to 1.510 (3) Å]. Apparent P═ O distances in partially oxygenated C₂H₅C(CH₂PPh₂)₃ (Chekhlov, 2000) are significantly shorter, due to a statistical character of the structure.

In (I), the hydrogen bonds in which water molecules act as proton donors (Table 2, Fig. 2) link organic molecules into chains along the [100] direction.

Related literature

The synthesis of the title compound was described by Pisareva et al. (2005). A structure of a solid solution of C₂H₅C(CH₂PPh₂)₃ and its partially oxygenated derivatives was described by Chekhlov (2000). Lees & Platt (2005) describe the structure of La and Pr nitrate complexes with CH₃C[CH₂P(O)Ph₂], in which tridentate organic ligands are linked by phosphoryl O atoms to two Ln atoms, to one atom in a bidentate-chelating way and to the other in a monodentate way.

S2. Experimental

The compound was prepared according to the procedure described by Pisareva et al. (2005) and recrystallized from dichloroethane.

S3. Refinement

The H atoms of the organic molecule were refined in idealized geometrical positions with displacement parameters being equal to 1.2 (CH₂ groups and phenyl rings) or 1.5 (CH₃ groups) times U_eq of the attached C atoms. The H atoms of the water molecule were located in a difference map and refined with individual isotropic displacement parameters and free coordinates.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size. The H atoms of the organic molecule are omitted for clarity.
	Fig. 2. The packing of (I), viewed down the [010] axis, showing the chains formed due to hydrogen bonding. H atoms not involved in hydrogen bonding are omitted.

1,1,1-Tris[(diphenylphosphoryl)methyl]propane monohydrate

Crystal data

C42H41O3P3·H2O	F(000) = 744
Mr = 704.67	Dx = 1.305 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 5344 reflections
a = 9.5303 (2) Å	θ = 2.1–30.0°
b = 10.4028 (2) Å	µ = 0.21 mm^−1
c = 18.0951 (4) Å	T = 100 K
β = 90.1433 (14)°	Fragment, colourless
V = 1793.98 (6) Å^3	0.18 × 0.16 × 0.10 mm
Z = 2

Data collection

Bruker Kappa APEX II area-detector diffractometer	8909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 30.0°, θmin = 2.1°
ω and φ scans	h = −13→13
41040 measured reflections	k = −14→14
10441 independent reflections	l = −25→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.0298P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
10441 reflections	Δρmax = 0.29 e Å^−3
450 parameters	Δρmin = −0.26 e Å^−3
2 restraints	Absolute structure: Flack (1983), 5207 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.36674 (4)	0.40193 (4)	0.75195 (2)	0.01293 (9)
P2	0.62248 (4)	0.41286 (4)	0.92906 (2)	0.01280 (8)
P3	0.76944 (4)	0.11940 (4)	0.72480 (2)	0.01326 (8)
O1	0.33318 (11)	0.30643 (11)	0.81087 (6)	0.0176 (2)
O2	0.53020 (11)	0.52545 (11)	0.91384 (6)	0.0173 (2)
O3	0.90964 (12)	0.12698 (12)	0.76149 (6)	0.0211 (3)
O4	0.11458 (18)	0.14636 (18)	0.87526 (9)	0.0428 (4)
H4C	0.172 (3)	0.187 (2)	0.8590 (13)	0.040 (7)*
H4D	0.049 (3)	0.140 (2)	0.8426 (15)	0.059 (8)*
C1	0.66847 (15)	0.37270 (15)	0.77288 (8)	0.0128 (3)
C2	0.54549 (15)	0.46501 (15)	0.75384 (8)	0.0127 (3)
H2A	0.5649	0.5027	0.7047	0.015*
H2B	0.5478	0.5364	0.7900	0.015*
C3	0.64933 (16)	0.30879 (15)	0.84973 (8)	0.0127 (3)
H3A	0.7333	0.2555	0.8597	0.015*
H3B	0.5681	0.2497	0.8465	0.015*
C4	0.67527 (16)	0.26866 (15)	0.71198 (8)	0.0138 (3)
H4A	0.7151	0.3103	0.6675	0.017*
H4B	0.5772	0.2456	0.6996	0.017*
C5	0.80796 (16)	0.44960 (16)	0.77433 (9)	0.0152 (3)
H5A	0.8074	0.5055	0.8186	0.018*
H5B	0.8860	0.3877	0.7804	0.018*
C6	0.83946 (18)	0.53319 (17)	0.70727 (9)	0.0214 (4)
H6A	0.9297	0.5768	0.7144	0.032*
H6B	0.7651	0.5974	0.7013	0.032*
H6C	0.8439	0.4792	0.6630	0.032*
C11	0.33661 (16)	0.33075 (16)	0.66157 (8)	0.0137 (3)
C12	0.40089 (16)	0.37265 (16)	0.59636 (9)	0.0169 (3)
H12	0.4595	0.4465	0.5971	0.020*
C13	0.37941 (17)	0.30679 (17)	0.53082 (9)	0.0195 (3)
H13	0.4229	0.3359	0.4867	0.023*
C14	0.29503 (17)	0.19891 (17)	0.52929 (9)	0.0202 (4)
H14	0.2823	0.1528	0.4845	0.024*
C15	0.22902 (18)	0.15812 (17)	0.59328 (9)	0.0216 (4)
H15	0.1695	0.0849	0.5919	0.026*
C16	0.24919 (17)	0.22344 (17)	0.65929 (9)	0.0179 (3)
H16	0.2034	0.1950	0.7029	0.021*
C21	0.25877 (16)	0.54402 (16)	0.75900 (9)	0.0169 (3)
C22	0.19743 (17)	0.57038 (19)	0.82698 (10)	0.0232 (4)
H22	0.2074	0.5112	0.8666	0.028*
C23	0.12141 (18)	0.6833 (2)	0.83705 (11)	0.0307 (5)
H23	0.0801	0.7014	0.8836	0.037*
C24	0.10612 (18)	0.76866 (19)	0.77967 (12)	0.0297 (4)
H24	0.0555	0.8463	0.7868	0.036*
C25	0.16454 (18)	0.74143 (19)	0.71131 (11)	0.0270 (4)
H25	0.1523	0.7999	0.6715	0.032*
C26	0.24067 (17)	0.62945 (17)	0.70078 (10)	0.0211 (4)
H26	0.2804	0.6112	0.6538	0.025*
C31	0.55012 (16)	0.30556 (16)	0.99754 (8)	0.0154 (3)
C32	0.42571 (17)	0.24121 (17)	0.98061 (9)	0.0192 (3)
H32	0.3829	0.2532	0.9336	0.023*
C33	0.36416 (18)	0.16000 (17)	1.03175 (9)	0.0218 (4)
H33	0.2799	0.1158	1.0197	0.026*
C34	0.42611 (18)	0.14341 (17)	1.10081 (9)	0.0206 (4)
H34	0.3849	0.0866	1.1356	0.025*
C35	0.54691 (17)	0.20900 (17)	1.11887 (9)	0.0190 (3)
H35	0.5871	0.1993	1.1667	0.023*
C36	0.61033 (17)	0.28930 (17)	1.06753 (9)	0.0179 (3)
H36	0.6946	0.3332	1.0799	0.022*
C41	0.79016 (16)	0.46439 (16)	0.96587 (8)	0.0159 (3)
C42	0.79740 (17)	0.58912 (17)	0.99403 (9)	0.0189 (3)
H42	0.7180	0.6441	0.9909	0.023*
C43	0.92054 (19)	0.63294 (18)	1.02658 (10)	0.0241 (4)
H43	0.9257	0.7178	1.0458	0.029*
C44	1.03596 (19)	0.55195 (19)	1.03080 (10)	0.0258 (4)
H44	1.1198	0.5814	1.0538	0.031*
C45	1.03050 (18)	0.42938 (19)	1.00206 (10)	0.0253 (4)
H45	1.1105	0.3750	1.0048	0.030*
C46	0.90713 (17)	0.38523 (17)	0.96887 (9)	0.0210 (4)
H46	0.9033	0.3012	0.9484	0.025*
C51	0.78361 (16)	0.05900 (15)	0.63142 (9)	0.0146 (3)
C52	0.90304 (17)	−0.01057 (17)	0.61250 (10)	0.0215 (4)
H52	0.9718	−0.0288	0.6491	0.026*
C53	0.92244 (19)	−0.05350 (19)	0.54055 (11)	0.0275 (4)
H53	1.0043	−0.1009	0.5281	0.033*
C54	0.82304 (19)	−0.02736 (18)	0.48714 (10)	0.0249 (4)
H54	0.8379	−0.0545	0.4376	0.030*
C55	0.70208 (19)	0.03810 (17)	0.50538 (10)	0.0225 (4)
H55	0.6325	0.0538	0.4688	0.027*
C56	0.68198 (17)	0.08104 (16)	0.57717 (9)	0.0188 (3)
H56	0.5984	0.1258	0.5895	0.023*
C61	0.65514 (16)	0.00712 (15)	0.77204 (8)	0.0137 (3)
C62	0.71799 (17)	−0.10455 (16)	0.79916 (9)	0.0181 (3)
H62	0.8166	−0.1155	0.7952	0.022*
C63	0.63681 (19)	−0.19994 (17)	0.83196 (9)	0.0213 (4)
H63	0.6800	−0.2764	0.8496	0.026*
C64	0.4936 (2)	−0.18373 (15)	0.83895 (10)	0.0213 (3)
H64	0.4383	−0.2491	0.8612	0.026*
C65	0.43039 (18)	−0.07184 (17)	0.81350 (9)	0.0212 (4)
H65	0.3322	−0.0598	0.8193	0.025*
C66	0.51071 (16)	0.02237 (16)	0.77960 (9)	0.0168 (3)
H66	0.4668	0.0980	0.7614	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01193 (19)	0.0149 (2)	0.01195 (19)	−0.00107 (16)	−0.00066 (14)	0.00143 (16)
P2	0.01457 (19)	0.0123 (2)	0.01157 (19)	0.00009 (16)	−0.00123 (14)	−0.00020 (16)
P3	0.01216 (18)	0.0129 (2)	0.01469 (19)	−0.00004 (15)	−0.00148 (14)	−0.00014 (16)
O1	0.0176 (6)	0.0211 (7)	0.0140 (5)	−0.0026 (5)	−0.0015 (4)	0.0043 (5)
O2	0.0202 (6)	0.0154 (6)	0.0164 (6)	0.0038 (5)	−0.0008 (4)	0.0006 (4)
O3	0.0153 (5)	0.0230 (7)	0.0251 (6)	−0.0006 (5)	−0.0064 (5)	−0.0005 (5)
O4	0.0309 (8)	0.0641 (12)	0.0334 (9)	−0.0231 (8)	−0.0093 (7)	0.0192 (8)
C1	0.0133 (7)	0.0118 (8)	0.0133 (7)	−0.0010 (6)	−0.0012 (5)	0.0013 (6)
C2	0.0129 (7)	0.0130 (8)	0.0121 (7)	−0.0026 (6)	−0.0013 (5)	0.0011 (6)
C3	0.0136 (7)	0.0121 (8)	0.0125 (7)	−0.0006 (6)	−0.0020 (5)	0.0000 (6)
C4	0.0139 (7)	0.0141 (8)	0.0135 (7)	−0.0015 (6)	−0.0002 (6)	0.0003 (6)
C5	0.0142 (7)	0.0143 (8)	0.0170 (8)	−0.0022 (6)	−0.0004 (6)	0.0005 (6)
C6	0.0200 (8)	0.0240 (9)	0.0203 (8)	−0.0091 (7)	0.0018 (6)	0.0010 (7)
C11	0.0121 (7)	0.0160 (8)	0.0130 (7)	0.0023 (6)	−0.0015 (5)	0.0007 (6)
C12	0.0147 (7)	0.0167 (9)	0.0194 (8)	−0.0008 (6)	−0.0026 (6)	0.0032 (7)
C13	0.0189 (8)	0.0239 (9)	0.0155 (8)	0.0004 (7)	0.0016 (6)	0.0006 (7)
C14	0.0213 (8)	0.0234 (9)	0.0159 (8)	0.0010 (7)	−0.0034 (6)	−0.0029 (7)
C15	0.0227 (9)	0.0188 (9)	0.0232 (9)	−0.0069 (7)	−0.0022 (7)	0.0002 (7)
C16	0.0172 (8)	0.0189 (9)	0.0176 (8)	−0.0031 (7)	−0.0008 (6)	0.0032 (6)
C21	0.0118 (7)	0.0166 (8)	0.0224 (8)	−0.0008 (6)	−0.0026 (6)	−0.0008 (7)
C22	0.0184 (8)	0.0286 (10)	0.0227 (9)	0.0035 (7)	0.0008 (7)	−0.0013 (7)
C23	0.0200 (9)	0.0376 (12)	0.0344 (11)	0.0041 (8)	0.0027 (8)	−0.0157 (9)
C24	0.0133 (8)	0.0234 (10)	0.0523 (13)	0.0019 (7)	0.0007 (8)	−0.0078 (9)
C25	0.0173 (8)	0.0216 (10)	0.0420 (11)	0.0020 (7)	0.0023 (8)	0.0046 (8)
C26	0.0151 (8)	0.0224 (9)	0.0258 (9)	0.0008 (7)	0.0022 (6)	0.0030 (7)
C31	0.0174 (8)	0.0151 (8)	0.0138 (8)	0.0022 (6)	0.0002 (6)	0.0005 (6)
C32	0.0180 (8)	0.0259 (10)	0.0137 (8)	0.0004 (7)	−0.0014 (6)	0.0025 (7)
C33	0.0184 (8)	0.0250 (10)	0.0221 (9)	−0.0032 (7)	0.0020 (7)	0.0042 (7)
C34	0.0232 (9)	0.0207 (9)	0.0180 (8)	0.0023 (7)	0.0054 (7)	0.0047 (7)
C35	0.0274 (9)	0.0179 (9)	0.0119 (7)	0.0045 (7)	−0.0013 (6)	0.0016 (6)
C36	0.0226 (8)	0.0165 (9)	0.0147 (8)	0.0014 (7)	−0.0024 (6)	−0.0022 (6)
C41	0.0180 (8)	0.0183 (9)	0.0115 (7)	−0.0042 (6)	−0.0018 (6)	0.0017 (6)
C42	0.0212 (8)	0.0194 (9)	0.0161 (8)	−0.0035 (7)	−0.0012 (6)	−0.0010 (7)
C43	0.0265 (9)	0.0232 (10)	0.0227 (9)	−0.0104 (7)	−0.0010 (7)	−0.0047 (7)
C44	0.0230 (9)	0.0327 (11)	0.0216 (9)	−0.0121 (8)	−0.0053 (7)	0.0020 (8)
C45	0.0188 (8)	0.0296 (11)	0.0275 (10)	0.0002 (7)	−0.0038 (7)	0.0047 (8)
C46	0.0228 (8)	0.0185 (9)	0.0217 (9)	−0.0016 (7)	−0.0044 (7)	0.0005 (7)
C51	0.0157 (7)	0.0120 (8)	0.0162 (8)	−0.0014 (6)	0.0025 (6)	0.0000 (6)
C52	0.0145 (8)	0.0217 (9)	0.0282 (10)	−0.0007 (7)	−0.0013 (7)	−0.0047 (7)
C53	0.0207 (9)	0.0272 (11)	0.0345 (10)	0.0012 (8)	0.0074 (7)	−0.0107 (8)
C54	0.0314 (10)	0.0235 (10)	0.0198 (9)	−0.0066 (8)	0.0079 (7)	−0.0066 (7)
C55	0.0307 (10)	0.0175 (9)	0.0193 (9)	−0.0016 (7)	−0.0027 (7)	0.0019 (7)
C56	0.0211 (8)	0.0177 (9)	0.0178 (8)	0.0036 (7)	0.0000 (6)	0.0005 (7)
C61	0.0194 (8)	0.0117 (8)	0.0098 (7)	−0.0026 (6)	−0.0019 (6)	−0.0024 (6)
C62	0.0208 (8)	0.0180 (9)	0.0156 (8)	0.0021 (7)	−0.0023 (6)	−0.0010 (6)
C63	0.0358 (10)	0.0137 (8)	0.0142 (8)	0.0023 (7)	−0.0027 (7)	0.0003 (6)
C64	0.0332 (9)	0.0159 (8)	0.0148 (7)	−0.0083 (8)	0.0016 (6)	0.0006 (8)
C65	0.0198 (8)	0.0222 (9)	0.0216 (9)	−0.0063 (7)	0.0013 (6)	−0.0011 (7)
C66	0.0178 (8)	0.0143 (8)	0.0183 (8)	0.0000 (6)	−0.0033 (6)	0.0000 (6)

Geometric parameters (Å, º)

P1—O1	1.4927 (12)	C24—H24	0.9500
P1—C21	1.8057 (17)	C25—C26	1.386 (2)
P1—C11	1.8175 (16)	C25—H25	0.9500
P1—C2	1.8257 (15)	C26—H26	0.9500
P2—O2	1.4899 (12)	C31—C32	1.395 (2)
P2—C31	1.8060 (16)	C31—C36	1.399 (2)
P2—C41	1.8109 (16)	C32—C33	1.385 (2)
P2—C3	1.8165 (16)	C32—H32	0.9500
P3—O3	1.4926 (12)	C33—C34	1.392 (2)
P3—C4	1.8081 (16)	C33—H33	0.9500
P3—C51	1.8081 (16)	C34—C35	1.377 (2)
P3—C61	1.8128 (16)	C34—H34	0.9500
O4—H4C	0.75 (3)	C35—C36	1.389 (2)
O4—H4D	0.86 (3)	C35—H35	0.9500
C1—C2	1.553 (2)	C36—H36	0.9500
C1—C3	1.553 (2)	C41—C46	1.387 (2)
C1—C4	1.546 (2)	C41—C42	1.396 (2)
C1—C5	1.552 (2)	C42—C43	1.389 (2)
C2—H2A	0.9900	C42—H42	0.9500
C2—H2B	0.9900	C43—C44	1.388 (3)
C3—H3A	0.9900	C43—H43	0.9500
C3—H3B	0.9900	C44—C45	1.378 (3)
C4—H4A	0.9900	C44—H44	0.9500
C4—H4B	0.9900	C45—C46	1.397 (2)
C5—C6	1.523 (2)	C45—H45	0.9500
C5—H5A	0.9900	C46—H46	0.9500
C5—H5B	0.9900	C51—C52	1.392 (2)
C6—H6A	0.9800	C51—C56	1.396 (2)
C6—H6B	0.9800	C52—C53	1.389 (2)
C6—H6C	0.9800	C52—H52	0.9500
C11—C16	1.393 (2)	C53—C54	1.379 (3)
C11—C12	1.400 (2)	C53—H53	0.9500
C12—C13	1.384 (2)	C54—C55	1.380 (3)
C12—H12	0.9500	C54—H54	0.9500
C13—C14	1.381 (2)	C55—C56	1.387 (2)
C13—H13	0.9500	C55—H55	0.9500
C14—C15	1.386 (2)	C56—H56	0.9500
C14—H14	0.9500	C61—C66	1.393 (2)
C15—C16	1.387 (2)	C61—C62	1.396 (2)
C15—H15	0.9500	C62—C63	1.392 (2)
C16—H16	0.9500	C62—H62	0.9500
C21—C26	1.389 (2)	C63—C64	1.382 (3)
C21—C22	1.391 (2)	C63—H63	0.9500
C22—C23	1.393 (3)	C64—C65	1.389 (2)
C22—H22	0.9500	C64—H64	0.9500
C23—C24	1.373 (3)	C65—C66	1.387 (2)
C23—H23	0.9500	C65—H65	0.9500
C24—C25	1.387 (3)	C66—H66	0.9500
O1—P1—C2	115.31 (7)	C23—C24—C25	120.02 (18)
O1—P1—C11	109.75 (7)	C23—C24—H24	120.0
O1—P1—C21	111.79 (7)	C25—C24—H24	120.0
C2—P1—C11	107.97 (7)	C26—C25—C24	120.38 (18)
C2—P1—C21	103.67 (7)	C26—C25—H25	119.8
C11—P1—C21	107.96 (7)	C24—C25—H25	119.8
O2—P2—C3	114.00 (7)	C25—C26—C21	119.85 (16)
O2—P2—C31	112.73 (7)	C25—C26—H26	120.1
O2—P2—C41	110.81 (7)	C21—C26—H26	120.1
C3—P2—C31	103.21 (7)	C32—C31—C36	119.16 (15)
C3—P2—C41	109.94 (7)	C32—C31—P2	118.14 (12)
C31—P2—C41	105.59 (7)	C36—C31—P2	122.64 (13)
O3—P3—C4	117.08 (7)	C33—C32—C31	120.48 (15)
O3—P3—C51	111.42 (7)	C33—C32—H32	119.8
O3—P3—C61	111.26 (7)	C31—C32—H32	119.8
C4—P3—C51	102.51 (7)	C32—C33—C34	119.76 (16)
C4—P3—C61	108.37 (7)	C32—C33—H33	120.1
C51—P3—C61	105.26 (7)	C34—C33—H33	120.1
H4C—O4—H4D	107 (3)	C35—C34—C33	120.29 (15)
C2—C1—C3	111.91 (12)	C35—C34—H34	119.9
C2—C1—C4	107.92 (12)	C33—C34—H34	119.9
C2—C1—C5	109.33 (12)	C34—C35—C36	120.28 (15)
C3—C1—C4	110.11 (12)	C34—C35—H35	119.9
C3—C1—C5	107.95 (12)	C36—C35—H35	119.9
C4—C1—C5	109.60 (12)	C35—C36—C31	119.99 (15)
C1—C2—P1	119.05 (11)	C35—C36—H36	120.0
C1—C2—H2A	107.6	C31—C36—H36	120.0
P1—C2—H2A	107.6	C46—C41—C42	119.91 (15)
C1—C2—H2B	107.6	C46—C41—P2	123.17 (13)
P1—C2—H2B	107.6	C42—C41—P2	116.89 (13)
H2A—C2—H2B	107.0	C43—C42—C41	120.06 (16)
C1—C3—P2	118.01 (11)	C43—C42—H42	120.0
C1—C3—H3A	107.8	C41—C42—H42	120.0
P2—C3—H3A	107.8	C44—C43—C42	119.54 (17)
C1—C3—H3B	107.8	C44—C43—H43	120.2
P2—C3—H3B	107.8	C42—C43—H43	120.2
H3A—C3—H3B	107.1	C45—C44—C43	120.79 (17)
C1—C4—P3	122.10 (11)	C45—C44—H44	119.6
C1—C4—H4A	106.8	C43—C44—H44	119.6
P3—C4—H4A	106.8	C44—C45—C46	119.84 (17)
C1—C4—H4B	106.8	C44—C45—H45	120.1
P3—C4—H4B	106.8	C46—C45—H45	120.1
H4A—C4—H4B	106.7	C41—C46—C45	119.82 (17)
C6—C5—C1	116.83 (13)	C41—C46—H46	120.1
C6—C5—H5A	108.1	C45—C46—H46	120.1
C1—C5—H5A	108.1	C52—C51—C56	118.58 (15)
C6—C5—H5B	108.1	C52—C51—P3	118.26 (12)
C1—C5—H5B	108.1	C56—C51—P3	123.14 (12)
H5A—C5—H5B	107.3	C53—C52—C51	120.56 (16)
C5—C6—H6A	109.5	C53—C52—H52	119.7
C5—C6—H6B	109.5	C51—C52—H52	119.7
H6A—C6—H6B	109.5	C54—C53—C52	120.05 (16)
C5—C6—H6C	109.5	C54—C53—H53	120.0
H6A—C6—H6C	109.5	C52—C53—H53	120.0
H6B—C6—H6C	109.5	C53—C54—C55	120.18 (17)
C16—C11—C12	119.16 (15)	C53—C54—H54	119.9
C16—C11—P1	116.50 (12)	C55—C54—H54	119.9
C12—C11—P1	124.26 (12)	C54—C55—C56	120.02 (17)
C13—C12—C11	120.24 (15)	C54—C55—H55	120.0
C13—C12—H12	119.9	C56—C55—H55	120.0
C11—C12—H12	119.9	C55—C56—C51	120.55 (16)
C14—C13—C12	120.28 (15)	C55—C56—H56	119.7
C14—C13—H13	119.9	C51—C56—H56	119.7
C12—C13—H13	119.9	C66—C61—C62	118.93 (15)
C13—C14—C15	119.85 (16)	C66—C61—P3	124.63 (12)
C13—C14—H14	120.1	C62—C61—P3	116.37 (12)
C15—C14—H14	120.1	C63—C62—C61	120.32 (15)
C14—C15—C16	120.48 (16)	C63—C62—H62	119.8
C14—C15—H15	119.8	C61—C62—H62	119.8
C16—C15—H15	119.8	C64—C63—C62	120.15 (16)
C15—C16—C11	119.97 (15)	C64—C63—H63	119.9
C15—C16—H16	120.0	C62—C63—H63	119.9
C11—C16—H16	120.0	C63—C64—C65	119.98 (16)
C26—C21—C22	119.55 (16)	C63—C64—H64	120.0
C26—C21—P1	122.68 (13)	C65—C64—H64	120.0
C22—C21—P1	117.70 (13)	C66—C65—C64	119.96 (16)
C21—C22—C23	120.14 (18)	C66—C65—H65	120.0
C21—C22—H22	119.9	C64—C65—H65	120.0
C23—C22—H22	119.9	C65—C66—C61	120.63 (15)
C24—C23—C22	120.03 (17)	C65—C66—H66	119.7
C24—C23—H23	120.0	C61—C66—H66	119.7
C22—C23—H23	120.0
C4—C1—C2—P1	63.32 (15)	C41—P2—C31—C36	8.84 (16)
C5—C1—C2—P1	−177.53 (10)	C3—P2—C31—C36	124.26 (14)
C3—C1—C2—P1	−57.98 (15)	C36—C31—C32—C33	−1.4 (2)
O1—P1—C2—C1	38.96 (14)	P2—C31—C32—C33	−178.59 (13)
C21—P1—C2—C1	161.48 (11)	C31—C32—C33—C34	0.6 (3)
C11—P1—C2—C1	−84.16 (12)	C32—C33—C34—C35	1.1 (3)
C4—C1—C3—P2	−174.49 (10)	C33—C34—C35—C36	−2.0 (3)
C5—C1—C3—P2	65.90 (15)	C34—C35—C36—C31	1.1 (2)
C2—C1—C3—P2	−54.46 (16)	C32—C31—C36—C35	0.6 (2)
O2—P2—C3—C1	39.48 (14)	P2—C31—C36—C35	177.59 (12)
C31—P2—C3—C1	162.10 (11)	O2—P2—C41—C46	−164.41 (13)
C41—P2—C3—C1	−85.64 (13)	C31—P2—C41—C46	73.23 (15)
C5—C1—C4—P3	78.24 (15)	C3—P2—C41—C46	−37.48 (16)
C3—C1—C4—P3	−40.37 (17)	O2—P2—C41—C42	17.44 (15)
C2—C1—C4—P3	−162.79 (11)	C31—P2—C41—C42	−104.92 (13)
O3—P3—C4—C1	−42.42 (14)	C3—P2—C41—C42	144.37 (12)
C51—P3—C4—C1	−164.67 (12)	C46—C41—C42—C43	−1.5 (2)
C61—P3—C4—C1	84.37 (13)	P2—C41—C42—C43	176.71 (13)
C4—C1—C5—C6	67.01 (17)	C41—C42—C43—C44	0.1 (3)
C3—C1—C5—C6	−173.05 (13)	C42—C43—C44—C45	1.0 (3)
C2—C1—C5—C6	−51.09 (17)	C43—C44—C45—C46	−0.6 (3)
O1—P1—C11—C16	19.90 (15)	C42—C41—C46—C45	1.9 (2)
C21—P1—C11—C16	−102.17 (13)	P2—C41—C46—C45	−176.20 (13)
C2—P1—C11—C16	146.34 (12)	C44—C45—C46—C41	−0.8 (3)
O1—P1—C11—C12	−156.57 (13)	O3—P3—C51—C52	20.61 (15)
C21—P1—C11—C12	81.36 (15)	C4—P3—C51—C52	146.62 (13)
C2—P1—C11—C12	−30.13 (16)	C61—P3—C51—C52	−100.10 (14)
C16—C11—C12—C13	−1.0 (2)	O3—P3—C51—C56	−158.05 (13)
P1—C11—C12—C13	175.35 (12)	C4—P3—C51—C56	−32.04 (15)
C11—C12—C13—C14	−0.3 (2)	C61—P3—C51—C56	81.23 (15)
C12—C13—C14—C15	1.5 (3)	C56—C51—C52—C53	2.0 (3)
C13—C14—C15—C16	−1.3 (3)	P3—C51—C52—C53	−176.72 (14)
C14—C15—C16—C11	−0.1 (3)	C51—C52—C53—C54	0.0 (3)
C12—C11—C16—C15	1.3 (2)	C52—C53—C54—C55	−2.0 (3)
P1—C11—C16—C15	−175.39 (13)	C53—C54—C55—C56	1.8 (3)
O1—P1—C21—C26	−161.46 (13)	C54—C55—C56—C51	0.2 (3)
C11—P1—C21—C26	−40.65 (16)	C52—C51—C56—C55	−2.1 (2)
C2—P1—C21—C26	73.72 (15)	P3—C51—C56—C55	176.55 (13)
O1—P1—C21—C22	21.58 (15)	O3—P3—C61—C66	144.99 (13)
C11—P1—C21—C22	142.39 (13)	C4—P3—C61—C66	14.91 (15)
C2—P1—C21—C22	−103.24 (14)	C51—P3—C61—C66	−94.19 (14)
C26—C21—C22—C23	−1.6 (3)	O3—P3—C61—C62	−38.16 (14)
P1—C21—C22—C23	175.42 (13)	C4—P3—C61—C62	−168.25 (12)
C21—C22—C23—C24	0.4 (3)	C51—P3—C61—C62	82.65 (13)
C22—C23—C24—C25	1.0 (3)	C66—C61—C62—C63	1.2 (2)
C23—C24—C25—C26	−1.2 (3)	P3—C61—C62—C63	−175.86 (12)
C24—C25—C26—C21	−0.1 (3)	C61—C62—C63—C64	−1.0 (2)
C22—C21—C26—C25	1.5 (2)	C62—C63—C64—C65	−0.3 (2)
P1—C21—C26—C25	−175.43 (13)	C63—C64—C65—C66	1.4 (3)
O2—P2—C31—C32	64.77 (15)	C64—C65—C66—C61	−1.3 (2)
C41—P2—C31—C32	−174.11 (13)	C62—C61—C66—C65	0.0 (2)
C3—P2—C31—C32	−58.69 (14)	P3—C61—C66—C65	176.74 (13)
O2—P2—C31—C36	−112.27 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4C···O1	0.75 (3)	2.16 (3)	2.912 (2)	179 (3)
O4—H4D···O3^i	0.86 (3)	1.98 (3)	2.8413 (19)	176 (3)

Symmetry code: (i) x−1, y, z.