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In the crystal structu of the title compound, C11H22O8P2·0.5H2O, the asymmetric unit contains two spiro­[5.5]undecane mol­ecules and one water mol­ecule. The structure is stabilized by intra- and inter­molecular C—H...O and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020605/hk2053sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020605/hk2053Isup2.hkl
Contains datablock I

CCDC reference: 613721

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.008 Å
  • Some non-H atoms missing
  • R factor = 0.069
  • wR factor = 0.191
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level A ABSMU01_ALERT_1_A The ratio of given/expected absorption coefficient lies outside the range 0.90 <> 1.10 Calculated value of mu = 0.611 Value of mu given = 0.306 CHEMW01_ALERT_1_A The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.90 <> 1.10 Calculated formula weight = 706.4902 Formula weight given = 353.2400
Alert level C CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.53 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT417_ALERT_2_C Short Inter D-H..H-D HWB .. H9A .. 2.13 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 PLAT731_ALERT_1_C Bond Calc 0.79(6), Rep 0.791(19) ...... 3.16 su-Rat OW -HWA 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.83(6), Rep 0.826(19) ...... 3.16 su-Rat OW -HWB 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 95(7), Rep 94(3) ...... 2.33 su-Rat HWA -OW -HWB 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C22 H46 O17 P4 Atom count from _chemical_formula_moiety:C11 H23 O8.5 P2 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C22 H46 O17 P4 Atom count from the _atom_site data: C11 H23 O8.5 P2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C22 H46 O17 P4 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 88.00 44.00 44.00 H 184.00 92.00 92.00 O 68.00 34.00 34.00 P 16.00 8.00 8.00
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

3,9-Bis(2-hydroxy-2-propyl)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane 3,9-dioxide hemihydrate top
Crystal data top
C11H22O8P2·0.5H2OZ = 4
Mr = 353.24F(000) = 748.0
Triclinic, P1Dx = 1.449 Mg m3
Hall symbol: -P 1Melting point: 460.15(2) K
a = 7.5500 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.539 (2) ÅCell parameters from 25 reflections
c = 21.068 (4) Åθ = 9–12°
α = 86.28 (3)°µ = 0.31 mm1
β = 82.40 (3)°T = 296 K
γ = 77.11 (3)°Block, colorless
V = 1618.7 (6) Å30.40 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
3535 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ω/2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 1212
Tmin = 0.929, Tmax = 0.941l = 2525
6846 measured reflections3 standard reflections every 120 min
6337 independent reflections intensity decay: 1%
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) = 0.191H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.07P)2 + 2P]
where P = (Fo2 + 2Fc2)/3
6337 reflections(Δ/σ)max < 0.001
388 parametersΔρmax = 0.44 e Å3
3 restraintsΔρmin = 0.42 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
P10.44396 (19)0.31670 (13)0.38743 (7)0.0347 (4)
P20.9125 (2)0.18520 (13)0.59305 (7)0.0377 (4)
O10.6733 (5)0.1769 (4)0.30315 (19)0.0619 (13)
H1A0.71480.17290.26520.093*
O20.2553 (5)0.3912 (4)0.40060 (19)0.0480 (10)
O30.5861 (5)0.4049 (3)0.38880 (18)0.0434 (9)
O40.4912 (5)0.2043 (3)0.43991 (17)0.0382 (9)
O50.7199 (5)0.2698 (4)0.57947 (17)0.0431 (9)
O61.0033 (5)0.1282 (3)0.52696 (17)0.0423 (9)
O70.8964 (6)0.0796 (4)0.6408 (2)0.0623 (12)
O81.0373 (5)0.4006 (3)0.56866 (18)0.0461 (10)
H8A0.94950.45930.57980.069*
C10.3594 (10)0.1514 (7)0.3066 (3)0.075 (2)
H1B0.38120.11410.26510.113*
H1C0.23420.19780.31420.113*
H1D0.38310.08330.33890.113*
C20.4552 (9)0.3548 (7)0.2583 (3)0.0621 (19)
H2B0.47660.31870.21660.093*
H2C0.53820.41090.26070.093*
H2D0.33150.40400.26570.093*
C30.4861 (8)0.2453 (6)0.3090 (3)0.0438 (14)
C40.6777 (7)0.1510 (5)0.4537 (3)0.0370 (13)
H4A0.74370.09650.41910.044*
H4B0.67530.09700.49280.044*
C50.7734 (8)0.3479 (5)0.4018 (3)0.0457 (15)
H5A0.83530.41710.40730.055*
H5B0.83910.29850.36540.055*
C60.7774 (7)0.2590 (5)0.4615 (2)0.0337 (12)
C70.9781 (7)0.2013 (5)0.4677 (3)0.0407 (13)
H7B1.02980.14470.43230.049*
H7C1.04380.27110.46490.049*
C80.6888 (7)0.3408 (5)0.5192 (2)0.0373 (13)
H8B0.73820.41860.51740.045*
H8C0.55810.36800.51720.045*
C91.0472 (8)0.2955 (5)0.6156 (3)0.0393 (13)
C100.9742 (9)0.3465 (6)0.6821 (3)0.0603 (18)
H10A1.04710.40360.69320.091*
H10B0.97990.27460.71280.091*
H10C0.84950.39330.68240.091*
C111.2472 (8)0.2251 (6)0.6116 (3)0.0594 (18)
H11A1.31850.28260.62370.089*
H11B1.29030.19880.56850.089*
H11C1.25910.14970.64010.089*
P30.43336 (19)0.28132 (12)0.09753 (7)0.0330 (3)
P40.87526 (18)0.22883 (12)0.11576 (6)0.0295 (3)
O90.6341 (6)0.0787 (4)0.1529 (2)0.0674 (14)
H9A0.66050.02690.18190.101*
O100.2514 (5)0.3659 (3)0.09177 (19)0.0485 (10)
O110.4651 (5)0.1931 (3)0.03468 (16)0.0365 (9)
O120.5865 (5)0.3626 (3)0.10506 (18)0.0433 (10)
O130.6930 (4)0.3141 (3)0.09362 (16)0.0346 (8)
O140.9597 (5)0.1358 (3)0.05814 (16)0.0366 (9)
O150.8384 (5)0.1542 (3)0.17518 (17)0.0430 (9)
O161.0282 (5)0.4241 (3)0.06865 (17)0.0391 (9)
H16A0.94400.48770.07540.059*
C120.3176 (10)0.1091 (7)0.1638 (4)0.078 (2)
H12A0.33950.05290.19940.118*
H12B0.20710.17390.16700.118*
H12C0.30530.05860.12450.118*
C130.5037 (9)0.2506 (6)0.2273 (3)0.0563 (17)
H13A0.52510.19300.26230.085*
H13B0.60740.28930.22740.085*
H13C0.39650.31770.23180.085*
C140.4756 (7)0.1746 (5)0.1647 (3)0.0395 (13)
C150.7690 (7)0.3064 (5)0.0872 (3)0.0421 (14)
H15B0.83940.37350.09000.051*
H15C0.83180.23950.11680.051*
C160.6442 (7)0.1427 (5)0.0142 (3)0.0348 (12)
H16B0.70910.07090.04060.042*
H16C0.63000.10980.02980.042*
C170.7565 (7)0.2475 (5)0.0192 (2)0.0311 (11)
C180.6727 (8)0.3562 (5)0.0273 (2)0.0378 (13)
H18A0.73120.42910.01630.045*
H18B0.54360.38600.02290.045*
C190.9528 (7)0.1871 (5)0.0075 (2)0.0367 (12)
H19A1.00380.11740.03690.044*
H19B1.02630.25240.01560.044*
C201.0306 (7)0.3363 (5)0.1231 (2)0.0345 (12)
C211.2267 (7)0.2547 (5)0.1200 (3)0.0454 (14)
H21A1.30930.31040.12380.068*
H21B1.25940.21240.07980.068*
H21C1.23430.19020.15440.068*
C220.9717 (8)0.4078 (5)0.1852 (3)0.0485 (15)
H22A1.05350.46390.18930.073*
H22B0.97500.34570.22070.073*
H22C0.84950.45890.18490.073*
OW0.9319 (8)0.0586 (5)0.2326 (3)0.094
HWA1.013 (7)0.006 (6)0.220 (4)0.113*
HWB0.895 (10)0.006 (6)0.252 (3)0.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0367 (8)0.0305 (7)0.0368 (8)0.0046 (6)0.0069 (6)0.0053 (6)
P20.0440 (9)0.0308 (7)0.0407 (8)0.0093 (6)0.0129 (7)0.0010 (6)
O10.047 (3)0.081 (3)0.042 (2)0.022 (2)0.007 (2)0.014 (2)
O20.041 (2)0.045 (2)0.053 (3)0.0020 (18)0.0040 (19)0.0085 (19)
O30.047 (2)0.032 (2)0.056 (2)0.0129 (18)0.0187 (19)0.0087 (17)
O40.039 (2)0.034 (2)0.044 (2)0.0128 (17)0.0064 (17)0.0016 (16)
O50.039 (2)0.051 (2)0.039 (2)0.0062 (18)0.0075 (17)0.0059 (18)
O60.047 (2)0.033 (2)0.046 (2)0.0010 (17)0.0143 (18)0.0072 (17)
O70.084 (3)0.045 (2)0.065 (3)0.027 (2)0.023 (2)0.017 (2)
O80.050 (2)0.034 (2)0.058 (3)0.0138 (18)0.007 (2)0.0029 (18)
C10.097 (6)0.079 (5)0.060 (5)0.032 (5)0.012 (4)0.033 (4)
C20.054 (4)0.084 (5)0.042 (4)0.002 (4)0.012 (3)0.005 (3)
C30.041 (3)0.055 (4)0.033 (3)0.001 (3)0.005 (3)0.015 (3)
C40.044 (3)0.027 (3)0.040 (3)0.005 (2)0.010 (3)0.002 (2)
C50.049 (4)0.043 (3)0.054 (4)0.025 (3)0.017 (3)0.005 (3)
C60.036 (3)0.028 (3)0.039 (3)0.011 (2)0.005 (2)0.003 (2)
C70.039 (3)0.043 (3)0.040 (3)0.005 (3)0.006 (3)0.010 (3)
C80.045 (3)0.032 (3)0.037 (3)0.005 (2)0.014 (3)0.006 (2)
C90.047 (3)0.035 (3)0.039 (3)0.009 (3)0.015 (3)0.003 (2)
C100.085 (5)0.053 (4)0.045 (4)0.013 (4)0.016 (3)0.007 (3)
C110.047 (4)0.058 (4)0.077 (5)0.007 (3)0.027 (3)0.004 (3)
P30.0366 (8)0.0241 (7)0.0393 (8)0.0043 (6)0.0121 (6)0.0008 (6)
P40.0310 (8)0.0239 (7)0.0325 (7)0.0021 (5)0.0074 (6)0.0007 (5)
O90.076 (3)0.046 (3)0.061 (3)0.027 (2)0.010 (2)0.002 (2)
O100.042 (2)0.039 (2)0.058 (3)0.0082 (18)0.0114 (19)0.0038 (18)
O110.037 (2)0.0350 (19)0.039 (2)0.0103 (16)0.0090 (17)0.0046 (16)
O120.051 (2)0.034 (2)0.051 (2)0.0161 (18)0.0234 (19)0.0145 (17)
O130.0287 (19)0.0332 (19)0.039 (2)0.0024 (15)0.0082 (16)0.0053 (16)
O140.040 (2)0.0263 (18)0.041 (2)0.0021 (16)0.0100 (17)0.0042 (15)
O150.050 (2)0.037 (2)0.041 (2)0.0092 (18)0.0061 (18)0.0083 (17)
O160.044 (2)0.0288 (19)0.042 (2)0.0035 (17)0.0088 (17)0.0039 (16)
C120.088 (6)0.072 (5)0.089 (6)0.039 (4)0.009 (4)0.036 (4)
C130.062 (4)0.058 (4)0.046 (4)0.003 (3)0.013 (3)0.001 (3)
C140.041 (3)0.032 (3)0.046 (3)0.003 (2)0.013 (3)0.002 (2)
C150.040 (3)0.047 (3)0.045 (3)0.021 (3)0.010 (3)0.005 (3)
C160.034 (3)0.029 (3)0.043 (3)0.004 (2)0.016 (2)0.004 (2)
C170.034 (3)0.025 (2)0.036 (3)0.008 (2)0.012 (2)0.002 (2)
C180.044 (3)0.024 (3)0.046 (3)0.001 (2)0.019 (3)0.000 (2)
C190.035 (3)0.035 (3)0.039 (3)0.003 (2)0.006 (2)0.002 (2)
C200.033 (3)0.034 (3)0.039 (3)0.007 (2)0.013 (2)0.001 (2)
C210.032 (3)0.050 (3)0.055 (4)0.004 (3)0.015 (3)0.006 (3)
C220.059 (4)0.045 (3)0.046 (4)0.016 (3)0.015 (3)0.006 (3)
OW0.0750.0920.0890.0280.0090.024
Geometric parameters (Å, º) top
P1—O21.465 (4)P3—O121.573 (4)
P1—O31.573 (4)P3—O111.581 (4)
P1—O41.581 (4)P3—C141.816 (5)
P1—C31.821 (5)P4—O151.463 (4)
P2—O71.465 (4)P4—O131.576 (3)
P2—O61.563 (4)P4—O141.585 (3)
P2—O51.578 (4)P4—C201.829 (5)
P2—C91.827 (5)O9—C141.422 (6)
O1—C31.430 (6)O9—H9A0.8200
O1—H1A0.8200O11—C161.450 (6)
O3—C51.462 (6)O12—C151.461 (6)
O4—C41.455 (6)O13—C181.455 (6)
O5—C81.450 (6)O14—C191.455 (6)
O6—C71.436 (6)O16—C201.426 (6)
O8—C91.431 (6)O16—H16A0.8200
O8—H8A0.8200C12—C141.504 (8)
C1—C31.530 (8)C12—H12A0.9600
C1—H1B0.9600C12—H12B0.9600
C1—H1C0.9600C12—H12C0.9600
C1—H1D0.9600C13—C141.513 (8)
C2—C31.520 (8)C13—H13A0.9600
C2—H2B0.9600C13—H13B0.9600
C2—H2C0.9600C13—H13C0.9600
C2—H2D0.9600C15—C171.525 (7)
C4—C61.525 (7)C15—H15B0.9700
C4—H4A0.9700C15—H15C0.9700
C4—H4B0.9700C16—C171.525 (7)
C5—C61.518 (7)C16—H16B0.9700
C5—H5A0.9700C16—H16C0.9700
C5—H5B0.9700C17—C191.523 (7)
C6—C71.521 (7)C17—C181.527 (7)
C6—C81.528 (7)C18—H18A0.9700
C7—H7B0.9700C18—H18B0.9700
C7—H7C0.9700C19—H19A0.9700
C8—H8B0.9700C19—H19B0.9700
C8—H8C0.9700C20—C221.517 (7)
C9—C111.521 (8)C20—C211.533 (7)
C9—C101.523 (8)C21—H21A0.9600
C10—H10A0.9600C21—H21B0.9600
C10—H10B0.9600C21—H21C0.9600
C10—H10C0.9600C22—H22A0.9600
C11—H11A0.9600C22—H22B0.9600
C11—H11B0.9600C22—H22C0.9600
C11—H11C0.9600OW—HWA0.791 (19)
P3—O101.456 (4)OW—HWB0.826 (19)
O2—P1—O3111.5 (2)O10—P3—O11111.2 (2)
O2—P1—O4111.6 (2)O12—P3—O11104.99 (19)
O3—P1—O4105.7 (2)O10—P3—C14113.0 (2)
O2—P1—C3111.6 (2)O12—P3—C14108.2 (2)
O3—P1—C3107.4 (2)O11—P3—C14107.8 (2)
O4—P1—C3108.7 (2)O15—P4—O13111.3 (2)
O7—P2—O6110.3 (2)O15—P4—O14111.3 (2)
O7—P2—O5112.3 (3)O13—P4—O14104.43 (19)
O6—P2—O5104.8 (2)O15—P4—C20112.6 (2)
O7—P2—C9113.2 (2)O13—P4—C20108.3 (2)
O6—P2—C9108.1 (2)O14—P4—C20108.5 (2)
O5—P2—C9107.7 (2)C14—O9—H9A109.5
C3—O1—H1A109.5C16—O11—P3123.3 (3)
C5—O3—P1120.7 (3)C15—O12—P3121.2 (3)
C4—O4—P1122.3 (3)C18—O13—P4123.4 (3)
C8—O5—P2123.0 (3)C19—O14—P4119.6 (3)
C7—O6—P2122.0 (3)C20—O16—H16A109.5
C9—O8—H8A109.5C14—C12—H12A109.5
C3—C1—H1B109.5C14—C12—H12B109.5
C3—C1—H1C109.5H12A—C12—H12B109.5
H1B—C1—H1C109.5C14—C12—H12C109.5
C3—C1—H1D109.5H12A—C12—H12C109.5
H1B—C1—H1D109.5H12B—C12—H12C109.5
H1C—C1—H1D109.5C14—C13—H13A109.5
C3—C2—H2B109.5C14—C13—H13B109.5
C3—C2—H2C109.5H13A—C13—H13B109.5
H2B—C2—H2C109.5C14—C13—H13C109.5
C3—C2—H2D109.5H13A—C13—H13C109.5
H2B—C2—H2D109.5H13B—C13—H13C109.5
H2C—C2—H2D109.5O9—C14—C12108.8 (5)
O1—C3—C2111.2 (5)O9—C14—C13112.4 (5)
O1—C3—C1110.7 (5)C12—C14—C13110.8 (5)
C2—C3—C1111.7 (5)O9—C14—P3104.7 (4)
O1—C3—P1105.0 (3)C12—C14—P3109.4 (4)
C2—C3—P1108.5 (4)C13—C14—P3110.5 (4)
C1—C3—P1109.5 (4)O12—C15—C17110.6 (4)
O4—C4—C6111.3 (4)O12—C15—H15B109.5
O4—C4—H4A109.4C17—C15—H15B109.5
C6—C4—H4A109.4O12—C15—H15C109.5
O4—C4—H4B109.4C17—C15—H15C109.5
C6—C4—H4B109.4H15B—C15—H15C108.1
H4A—C4—H4B108.0O11—C16—C17111.5 (4)
O3—C5—C6111.7 (4)O11—C16—H16B109.3
O3—C5—H5A109.3C17—C16—H16B109.3
C6—C5—H5A109.3O11—C16—H16C109.3
O3—C5—H5B109.3C17—C16—H16C109.3
C6—C5—H5B109.3H16B—C16—H16C108.0
H5A—C5—H5B107.9C19—C17—C15105.6 (4)
C5—C6—C7106.4 (4)C19—C17—C16110.2 (4)
C5—C6—C4109.6 (4)C15—C17—C16109.8 (4)
C7—C6—C4110.2 (4)C19—C17—C18110.4 (4)
C5—C6—C8108.5 (4)C15—C17—C18108.8 (4)
C7—C6—C8110.3 (4)C16—C17—C18111.9 (4)
C4—C6—C8111.6 (4)O13—C18—C17112.3 (4)
O6—C7—C6112.4 (4)O13—C18—H18A109.1
O6—C7—H7B109.1C17—C18—H18A109.1
C6—C7—H7B109.1O13—C18—H18B109.1
O6—C7—H7C109.1C17—C18—H18B109.1
C6—C7—H7C109.1H18A—C18—H18B107.9
H7B—C7—H7C107.9O14—C19—C17110.6 (4)
O5—C8—C6112.2 (4)O14—C19—H19A109.5
O5—C8—H8B109.2C17—C19—H19A109.5
C6—C8—H8B109.2O14—C19—H19B109.5
O5—C8—H8C109.2C17—C19—H19B109.5
C6—C8—H8C109.2H19A—C19—H19B108.1
H8B—C8—H8C107.9O16—C20—C22111.8 (4)
O8—C9—C11106.6 (5)O16—C20—C21106.0 (4)
O8—C9—C10110.7 (4)C22—C20—C21112.1 (4)
C11—C9—C10111.8 (5)O16—C20—P4108.7 (3)
O8—C9—P2107.7 (3)C22—C20—P4109.3 (4)
C11—C9—P2109.2 (4)C21—C20—P4108.9 (4)
C10—C9—P2110.7 (4)C20—C21—H21A109.5
C9—C10—H10A109.5C20—C21—H21B109.5
C9—C10—H10B109.5H21A—C21—H21B109.5
H10A—C10—H10B109.5C20—C21—H21C109.5
C9—C10—H10C109.5H21A—C21—H21C109.5
H10A—C10—H10C109.5H21B—C21—H21C109.5
H10B—C10—H10C109.5C20—C22—H22A109.5
C9—C11—H11A109.5C20—C22—H22B109.5
C9—C11—H11B109.5H22A—C22—H22B109.5
H11A—C11—H11B109.5C20—C22—H22C109.5
C9—C11—H11C109.5H22A—C22—H22C109.5
H11A—C11—H11C109.5H22B—C22—H22C109.5
H11B—C11—H11C109.5HWA—OW—HWB94 (3)
O10—P3—O12111.3 (2)
O2—P1—O3—C5156.1 (4)O10—P3—O11—C16152.9 (4)
O4—P1—O3—C534.6 (4)O12—P3—O11—C1632.5 (4)
C3—P1—O3—C581.4 (4)C14—P3—O11—C1682.7 (4)
O2—P1—O4—C4155.1 (3)O10—P3—O12—C15156.0 (4)
O3—P1—O4—C433.6 (4)O11—P3—O12—C1535.6 (4)
C3—P1—O4—C481.4 (4)C14—P3—O12—C1579.3 (4)
O7—P2—O5—C8153.4 (4)O15—P4—O13—C18154.7 (3)
O6—P2—O5—C833.6 (4)O14—P4—O13—C1834.5 (4)
C9—P2—O5—C881.3 (4)C20—P4—O13—C1881.0 (4)
O7—P2—O6—C7157.1 (4)O15—P4—O14—C19160.7 (3)
O5—P2—O6—C736.0 (4)O13—P4—O14—C1940.5 (4)
C9—P2—O6—C778.6 (4)C20—P4—O14—C1974.8 (4)
O2—P1—C3—O1179.9 (3)O10—P3—C14—O9165.1 (3)
O3—P1—C3—O157.4 (4)O12—P3—C14—O971.2 (4)
O4—P1—C3—O156.5 (4)O11—P3—C14—O941.8 (4)
O2—P1—C3—C261.0 (5)O10—P3—C14—C1248.6 (5)
O3—P1—C3—C261.5 (5)O12—P3—C14—C12172.3 (4)
O4—P1—C3—C2175.5 (4)O11—P3—C14—C1274.7 (5)
O2—P1—C3—C161.2 (5)O10—P3—C14—C1373.7 (5)
O3—P1—C3—C1176.3 (4)O12—P3—C14—C1350.0 (4)
O4—P1—C3—C162.4 (5)O11—P3—C14—C13163.1 (4)
P1—O4—C4—C647.3 (5)P3—O12—C15—C1752.1 (5)
P1—O3—C5—C650.2 (6)P3—O11—C16—C1745.3 (5)
O3—C5—C6—C7177.3 (4)O12—C15—C17—C19177.4 (4)
O3—C5—C6—C458.1 (6)O12—C15—C17—C1658.6 (5)
O3—C5—C6—C864.1 (5)O12—C15—C17—C1864.1 (5)
O4—C4—C6—C556.2 (6)O11—C16—C17—C19171.1 (4)
O4—C4—C6—C7173.1 (4)O11—C16—C17—C1555.2 (6)
O4—C4—C6—C864.1 (5)O11—C16—C17—C1865.7 (5)
P2—O6—C7—C650.3 (5)P4—O13—C18—C1743.4 (5)
C5—C6—C7—O6172.3 (4)C19—C17—C18—O1351.7 (6)
C4—C6—C7—O668.9 (5)C15—C17—C18—O13167.1 (4)
C8—C6—C7—O654.8 (5)C16—C17—C18—O1371.4 (5)
P2—O5—C8—C645.0 (6)P4—O14—C19—C1756.1 (5)
C5—C6—C8—O5168.2 (4)C15—C17—C19—O14175.7 (4)
C7—C6—C8—O551.9 (6)C16—C17—C19—O1465.8 (5)
C4—C6—C8—O570.9 (5)C18—C17—C19—O1458.3 (5)
O7—P2—C9—O8174.3 (3)O15—P4—C20—O16167.8 (3)
O6—P2—C9—O863.2 (4)O13—P4—C20—O1644.3 (4)
O5—P2—C9—O849.6 (4)O14—P4—C20—O1668.5 (4)
O7—P2—C9—C1170.3 (5)O15—P4—C20—C2245.6 (4)
O6—P2—C9—C1152.2 (4)O13—P4—C20—C2277.9 (4)
O5—P2—C9—C11164.9 (4)O14—P4—C20—C22169.3 (3)
O7—P2—C9—C1053.1 (5)O15—P4—C20—C2177.1 (4)
O6—P2—C9—C10175.6 (4)O13—P4—C20—C21159.4 (3)
O5—P2—C9—C1071.6 (4)O14—P4—C20—C2146.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW—HWA···O15i0.79 (6)2.06 (7)2.823 (7)163 (6)
O1—H1A···O150.822.002.818 (5)175
OW—HWB···O7ii0.82 (6)2.34 (6)2.706 (8)108 (5)
O8—H8A···O2iii0.821.972.785 (5)175
O9—H9A···OW0.822.272.599 (8)105
O16—H16A···O10iv0.821.902.716 (5)179
C5—H5A···O8v0.972.443.405 (7)173
C5—H5B···O10.972.513.106 (7)120
C7—H7C···O2vi0.972.473.332 (7)148
C8—H8B···O80.972.593.155 (7)117
C16—H16B···O90.972.503.056 (7)117
Symmetry codes: (i) x+2, y, z; (ii) x, y, z1; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z; (v) x+2, y+1, z+1; (vi) x+1, y, z.
 

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