In the crystal structu of the title compound, C
11H
22O
8P
2·0.5H
2O, 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
CCDC reference: 613721
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
C11H22O8P2·0.5H2O | Z = 4 |
Mr = 353.24 | F(000) = 748.0 |
Triclinic, P1 | Dx = 1.449 Mg m−3 |
Hall symbol: -P 1 | Melting point: 460.15(2) K |
a = 7.5500 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.539 (2) Å | Cell parameters from 25 reflections |
c = 21.068 (4) Å | θ = 9–12° |
α = 86.28 (3)° | µ = 0.31 mm−1 |
β = 82.40 (3)° | T = 296 K |
γ = 77.11 (3)° | Block, colorless |
V = 1618.7 (6) Å3 | 0.40 × 0.20 × 0.20 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 3535 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.929, Tmax = 0.941 | l = −25→25 |
6846 measured reflections | 3 standard reflections every 120 min |
6337 independent reflections | intensity decay: 1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.191 | H 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 parameters | Δρmax = 0.44 e Å−3 |
3 restraints | Δρmin = −0.42 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
P1 | 0.44396 (19) | 0.31670 (13) | 0.38743 (7) | 0.0347 (4) | |
P2 | 0.9125 (2) | 0.18520 (13) | 0.59305 (7) | 0.0377 (4) | |
O1 | 0.6733 (5) | 0.1769 (4) | 0.30315 (19) | 0.0619 (13) | |
H1A | 0.7148 | 0.1729 | 0.2652 | 0.093* | |
O2 | 0.2553 (5) | 0.3912 (4) | 0.40060 (19) | 0.0480 (10) | |
O3 | 0.5861 (5) | 0.4049 (3) | 0.38880 (18) | 0.0434 (9) | |
O4 | 0.4912 (5) | 0.2043 (3) | 0.43991 (17) | 0.0382 (9) | |
O5 | 0.7199 (5) | 0.2698 (4) | 0.57947 (17) | 0.0431 (9) | |
O6 | 1.0033 (5) | 0.1282 (3) | 0.52696 (17) | 0.0423 (9) | |
O7 | 0.8964 (6) | 0.0796 (4) | 0.6408 (2) | 0.0623 (12) | |
O8 | 1.0373 (5) | 0.4006 (3) | 0.56866 (18) | 0.0461 (10) | |
H8A | 0.9495 | 0.4593 | 0.5798 | 0.069* | |
C1 | 0.3594 (10) | 0.1514 (7) | 0.3066 (3) | 0.075 (2) | |
H1B | 0.3812 | 0.1141 | 0.2651 | 0.113* | |
H1C | 0.2342 | 0.1978 | 0.3142 | 0.113* | |
H1D | 0.3831 | 0.0833 | 0.3389 | 0.113* | |
C2 | 0.4552 (9) | 0.3548 (7) | 0.2583 (3) | 0.0621 (19) | |
H2B | 0.4766 | 0.3187 | 0.2166 | 0.093* | |
H2C | 0.5382 | 0.4109 | 0.2607 | 0.093* | |
H2D | 0.3315 | 0.4040 | 0.2657 | 0.093* | |
C3 | 0.4861 (8) | 0.2453 (6) | 0.3090 (3) | 0.0438 (14) | |
C4 | 0.6777 (7) | 0.1510 (5) | 0.4537 (3) | 0.0370 (13) | |
H4A | 0.7437 | 0.0965 | 0.4191 | 0.044* | |
H4B | 0.6753 | 0.0970 | 0.4928 | 0.044* | |
C5 | 0.7734 (8) | 0.3479 (5) | 0.4018 (3) | 0.0457 (15) | |
H5A | 0.8353 | 0.4171 | 0.4073 | 0.055* | |
H5B | 0.8391 | 0.2985 | 0.3654 | 0.055* | |
C6 | 0.7774 (7) | 0.2590 (5) | 0.4615 (2) | 0.0337 (12) | |
C7 | 0.9781 (7) | 0.2013 (5) | 0.4677 (3) | 0.0407 (13) | |
H7B | 1.0298 | 0.1447 | 0.4323 | 0.049* | |
H7C | 1.0438 | 0.2711 | 0.4649 | 0.049* | |
C8 | 0.6888 (7) | 0.3408 (5) | 0.5192 (2) | 0.0373 (13) | |
H8B | 0.7382 | 0.4186 | 0.5174 | 0.045* | |
H8C | 0.5581 | 0.3680 | 0.5172 | 0.045* | |
C9 | 1.0472 (8) | 0.2955 (5) | 0.6156 (3) | 0.0393 (13) | |
C10 | 0.9742 (9) | 0.3465 (6) | 0.6821 (3) | 0.0603 (18) | |
H10A | 1.0471 | 0.4036 | 0.6932 | 0.091* | |
H10B | 0.9799 | 0.2746 | 0.7128 | 0.091* | |
H10C | 0.8495 | 0.3933 | 0.6824 | 0.091* | |
C11 | 1.2472 (8) | 0.2251 (6) | 0.6116 (3) | 0.0594 (18) | |
H11A | 1.3185 | 0.2826 | 0.6237 | 0.089* | |
H11B | 1.2903 | 0.1988 | 0.5685 | 0.089* | |
H11C | 1.2591 | 0.1497 | 0.6401 | 0.089* | |
P3 | 0.43336 (19) | 0.28132 (12) | −0.09753 (7) | 0.0330 (3) | |
P4 | 0.87526 (18) | 0.22883 (12) | 0.11576 (6) | 0.0295 (3) | |
O9 | 0.6341 (6) | 0.0787 (4) | −0.1529 (2) | 0.0674 (14) | |
H9A | 0.6605 | 0.0269 | −0.1819 | 0.101* | |
O10 | 0.2514 (5) | 0.3659 (3) | −0.09177 (19) | 0.0485 (10) | |
O11 | 0.4651 (5) | 0.1931 (3) | −0.03468 (16) | 0.0365 (9) | |
O12 | 0.5865 (5) | 0.3626 (3) | −0.10506 (18) | 0.0433 (10) | |
O13 | 0.6930 (4) | 0.3141 (3) | 0.09362 (16) | 0.0346 (8) | |
O14 | 0.9597 (5) | 0.1358 (3) | 0.05814 (16) | 0.0366 (9) | |
O15 | 0.8384 (5) | 0.1542 (3) | 0.17518 (17) | 0.0430 (9) | |
O16 | 1.0282 (5) | 0.4241 (3) | 0.06865 (17) | 0.0391 (9) | |
H16A | 0.9440 | 0.4877 | 0.0754 | 0.059* | |
C12 | 0.3176 (10) | 0.1091 (7) | −0.1638 (4) | 0.078 (2) | |
H12A | 0.3395 | 0.0529 | −0.1994 | 0.118* | |
H12B | 0.2071 | 0.1739 | −0.1670 | 0.118* | |
H12C | 0.3053 | 0.0586 | −0.1245 | 0.118* | |
C13 | 0.5037 (9) | 0.2506 (6) | −0.2273 (3) | 0.0563 (17) | |
H13A | 0.5251 | 0.1930 | −0.2623 | 0.085* | |
H13B | 0.6074 | 0.2893 | −0.2274 | 0.085* | |
H13C | 0.3965 | 0.3177 | −0.2318 | 0.085* | |
C14 | 0.4756 (7) | 0.1746 (5) | −0.1647 (3) | 0.0395 (13) | |
C15 | 0.7690 (7) | 0.3064 (5) | −0.0872 (3) | 0.0421 (14) | |
H15B | 0.8394 | 0.3735 | −0.0900 | 0.051* | |
H15C | 0.8318 | 0.2395 | −0.1168 | 0.051* | |
C16 | 0.6442 (7) | 0.1427 (5) | −0.0142 (3) | 0.0348 (12) | |
H16B | 0.7091 | 0.0709 | −0.0406 | 0.042* | |
H16C | 0.6300 | 0.1098 | 0.0298 | 0.042* | |
C17 | 0.7565 (7) | 0.2475 (5) | −0.0192 (2) | 0.0311 (11) | |
C18 | 0.6727 (8) | 0.3562 (5) | 0.0273 (2) | 0.0378 (13) | |
H18A | 0.7312 | 0.4291 | 0.0163 | 0.045* | |
H18B | 0.5436 | 0.3860 | 0.0229 | 0.045* | |
C19 | 0.9528 (7) | 0.1871 (5) | −0.0075 (2) | 0.0367 (12) | |
H19A | 1.0038 | 0.1174 | −0.0369 | 0.044* | |
H19B | 1.0263 | 0.2524 | −0.0156 | 0.044* | |
C20 | 1.0306 (7) | 0.3363 (5) | 0.1231 (2) | 0.0345 (12) | |
C21 | 1.2267 (7) | 0.2547 (5) | 0.1200 (3) | 0.0454 (14) | |
H21A | 1.3093 | 0.3104 | 0.1238 | 0.068* | |
H21B | 1.2594 | 0.2124 | 0.0798 | 0.068* | |
H21C | 1.2343 | 0.1902 | 0.1544 | 0.068* | |
C22 | 0.9717 (8) | 0.4078 (5) | 0.1852 (3) | 0.0485 (15) | |
H22A | 1.0535 | 0.4639 | 0.1893 | 0.073* | |
H22B | 0.9750 | 0.3457 | 0.2207 | 0.073* | |
H22C | 0.8495 | 0.4589 | 0.1849 | 0.073* | |
OW | 0.9319 (8) | 0.0586 (5) | −0.2326 (3) | 0.094 | |
HWA | 1.013 (7) | 0.006 (6) | −0.220 (4) | 0.113* | |
HWB | 0.895 (10) | 0.006 (6) | −0.252 (3) | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0367 (8) | 0.0305 (7) | 0.0368 (8) | −0.0046 (6) | −0.0069 (6) | −0.0053 (6) |
P2 | 0.0440 (9) | 0.0308 (7) | 0.0407 (8) | −0.0093 (6) | −0.0129 (7) | 0.0010 (6) |
O1 | 0.047 (3) | 0.081 (3) | 0.042 (2) | 0.022 (2) | −0.007 (2) | −0.014 (2) |
O2 | 0.041 (2) | 0.045 (2) | 0.053 (3) | 0.0020 (18) | −0.0040 (19) | −0.0085 (19) |
O3 | 0.047 (2) | 0.032 (2) | 0.056 (2) | −0.0129 (18) | −0.0187 (19) | 0.0087 (17) |
O4 | 0.039 (2) | 0.034 (2) | 0.044 (2) | −0.0128 (17) | −0.0064 (17) | 0.0016 (16) |
O5 | 0.039 (2) | 0.051 (2) | 0.039 (2) | −0.0062 (18) | −0.0075 (17) | −0.0059 (18) |
O6 | 0.047 (2) | 0.033 (2) | 0.046 (2) | 0.0010 (17) | −0.0143 (18) | −0.0072 (17) |
O7 | 0.084 (3) | 0.045 (2) | 0.065 (3) | −0.027 (2) | −0.023 (2) | 0.017 (2) |
O8 | 0.050 (2) | 0.034 (2) | 0.058 (3) | −0.0138 (18) | −0.007 (2) | −0.0029 (18) |
C1 | 0.097 (6) | 0.079 (5) | 0.060 (5) | −0.032 (5) | −0.012 (4) | −0.033 (4) |
C2 | 0.054 (4) | 0.084 (5) | 0.042 (4) | 0.002 (4) | −0.012 (3) | −0.005 (3) |
C3 | 0.041 (3) | 0.055 (4) | 0.033 (3) | −0.001 (3) | −0.005 (3) | −0.015 (3) |
C4 | 0.044 (3) | 0.027 (3) | 0.040 (3) | −0.005 (2) | −0.010 (3) | −0.002 (2) |
C5 | 0.049 (4) | 0.043 (3) | 0.054 (4) | −0.025 (3) | −0.017 (3) | 0.005 (3) |
C6 | 0.036 (3) | 0.028 (3) | 0.039 (3) | −0.011 (2) | −0.005 (2) | −0.003 (2) |
C7 | 0.039 (3) | 0.043 (3) | 0.040 (3) | −0.005 (3) | −0.006 (3) | −0.010 (3) |
C8 | 0.045 (3) | 0.032 (3) | 0.037 (3) | −0.005 (2) | −0.014 (3) | −0.006 (2) |
C9 | 0.047 (3) | 0.035 (3) | 0.039 (3) | −0.009 (3) | −0.015 (3) | −0.003 (2) |
C10 | 0.085 (5) | 0.053 (4) | 0.045 (4) | −0.013 (4) | −0.016 (3) | −0.007 (3) |
C11 | 0.047 (4) | 0.058 (4) | 0.077 (5) | −0.007 (3) | −0.027 (3) | −0.004 (3) |
P3 | 0.0366 (8) | 0.0241 (7) | 0.0393 (8) | −0.0043 (6) | −0.0121 (6) | −0.0008 (6) |
P4 | 0.0310 (8) | 0.0239 (7) | 0.0325 (7) | −0.0021 (5) | −0.0074 (6) | 0.0007 (5) |
O9 | 0.076 (3) | 0.046 (3) | 0.061 (3) | 0.027 (2) | −0.010 (2) | −0.002 (2) |
O10 | 0.042 (2) | 0.039 (2) | 0.058 (3) | 0.0082 (18) | −0.0114 (19) | −0.0038 (18) |
O11 | 0.037 (2) | 0.0350 (19) | 0.039 (2) | −0.0103 (16) | −0.0090 (17) | 0.0046 (16) |
O12 | 0.051 (2) | 0.034 (2) | 0.051 (2) | −0.0161 (18) | −0.0234 (19) | 0.0145 (17) |
O13 | 0.0287 (19) | 0.0332 (19) | 0.039 (2) | 0.0024 (15) | −0.0082 (16) | −0.0053 (16) |
O14 | 0.040 (2) | 0.0263 (18) | 0.041 (2) | 0.0021 (16) | −0.0100 (17) | −0.0042 (15) |
O15 | 0.050 (2) | 0.037 (2) | 0.041 (2) | −0.0092 (18) | −0.0061 (18) | 0.0083 (17) |
O16 | 0.044 (2) | 0.0288 (19) | 0.042 (2) | −0.0035 (17) | −0.0088 (17) | 0.0039 (16) |
C12 | 0.088 (6) | 0.072 (5) | 0.089 (6) | −0.039 (4) | −0.009 (4) | −0.036 (4) |
C13 | 0.062 (4) | 0.058 (4) | 0.046 (4) | −0.003 (3) | −0.013 (3) | −0.001 (3) |
C14 | 0.041 (3) | 0.032 (3) | 0.046 (3) | −0.003 (2) | −0.013 (3) | −0.002 (2) |
C15 | 0.040 (3) | 0.047 (3) | 0.045 (3) | −0.021 (3) | −0.010 (3) | 0.005 (3) |
C16 | 0.034 (3) | 0.029 (3) | 0.043 (3) | −0.004 (2) | −0.016 (2) | 0.004 (2) |
C17 | 0.034 (3) | 0.025 (2) | 0.036 (3) | −0.008 (2) | −0.012 (2) | 0.002 (2) |
C18 | 0.044 (3) | 0.024 (3) | 0.046 (3) | −0.001 (2) | −0.019 (3) | 0.000 (2) |
C19 | 0.035 (3) | 0.035 (3) | 0.039 (3) | −0.003 (2) | −0.006 (2) | −0.002 (2) |
C20 | 0.033 (3) | 0.034 (3) | 0.039 (3) | −0.007 (2) | −0.013 (2) | 0.001 (2) |
C21 | 0.032 (3) | 0.050 (3) | 0.055 (4) | −0.004 (3) | −0.015 (3) | 0.006 (3) |
C22 | 0.059 (4) | 0.045 (3) | 0.046 (4) | −0.016 (3) | −0.015 (3) | −0.006 (3) |
OW | 0.075 | 0.092 | 0.089 | 0.028 | −0.009 | 0.024 |
Geometric parameters (Å, º) top
P1—O2 | 1.465 (4) | P3—O12 | 1.573 (4) |
P1—O3 | 1.573 (4) | P3—O11 | 1.581 (4) |
P1—O4 | 1.581 (4) | P3—C14 | 1.816 (5) |
P1—C3 | 1.821 (5) | P4—O15 | 1.463 (4) |
P2—O7 | 1.465 (4) | P4—O13 | 1.576 (3) |
P2—O6 | 1.563 (4) | P4—O14 | 1.585 (3) |
P2—O5 | 1.578 (4) | P4—C20 | 1.829 (5) |
P2—C9 | 1.827 (5) | O9—C14 | 1.422 (6) |
O1—C3 | 1.430 (6) | O9—H9A | 0.8200 |
O1—H1A | 0.8200 | O11—C16 | 1.450 (6) |
O3—C5 | 1.462 (6) | O12—C15 | 1.461 (6) |
O4—C4 | 1.455 (6) | O13—C18 | 1.455 (6) |
O5—C8 | 1.450 (6) | O14—C19 | 1.455 (6) |
O6—C7 | 1.436 (6) | O16—C20 | 1.426 (6) |
O8—C9 | 1.431 (6) | O16—H16A | 0.8200 |
O8—H8A | 0.8200 | C12—C14 | 1.504 (8) |
C1—C3 | 1.530 (8) | C12—H12A | 0.9600 |
C1—H1B | 0.9600 | C12—H12B | 0.9600 |
C1—H1C | 0.9600 | C12—H12C | 0.9600 |
C1—H1D | 0.9600 | C13—C14 | 1.513 (8) |
C2—C3 | 1.520 (8) | C13—H13A | 0.9600 |
C2—H2B | 0.9600 | C13—H13B | 0.9600 |
C2—H2C | 0.9600 | C13—H13C | 0.9600 |
C2—H2D | 0.9600 | C15—C17 | 1.525 (7) |
C4—C6 | 1.525 (7) | C15—H15B | 0.9700 |
C4—H4A | 0.9700 | C15—H15C | 0.9700 |
C4—H4B | 0.9700 | C16—C17 | 1.525 (7) |
C5—C6 | 1.518 (7) | C16—H16B | 0.9700 |
C5—H5A | 0.9700 | C16—H16C | 0.9700 |
C5—H5B | 0.9700 | C17—C19 | 1.523 (7) |
C6—C7 | 1.521 (7) | C17—C18 | 1.527 (7) |
C6—C8 | 1.528 (7) | C18—H18A | 0.9700 |
C7—H7B | 0.9700 | C18—H18B | 0.9700 |
C7—H7C | 0.9700 | C19—H19A | 0.9700 |
C8—H8B | 0.9700 | C19—H19B | 0.9700 |
C8—H8C | 0.9700 | C20—C22 | 1.517 (7) |
C9—C11 | 1.521 (8) | C20—C21 | 1.533 (7) |
C9—C10 | 1.523 (8) | C21—H21A | 0.9600 |
C10—H10A | 0.9600 | C21—H21B | 0.9600 |
C10—H10B | 0.9600 | C21—H21C | 0.9600 |
C10—H10C | 0.9600 | C22—H22A | 0.9600 |
C11—H11A | 0.9600 | C22—H22B | 0.9600 |
C11—H11B | 0.9600 | C22—H22C | 0.9600 |
C11—H11C | 0.9600 | OW—HWA | 0.791 (19) |
P3—O10 | 1.456 (4) | OW—HWB | 0.826 (19) |
| | | |
O2—P1—O3 | 111.5 (2) | O10—P3—O11 | 111.2 (2) |
O2—P1—O4 | 111.6 (2) | O12—P3—O11 | 104.99 (19) |
O3—P1—O4 | 105.7 (2) | O10—P3—C14 | 113.0 (2) |
O2—P1—C3 | 111.6 (2) | O12—P3—C14 | 108.2 (2) |
O3—P1—C3 | 107.4 (2) | O11—P3—C14 | 107.8 (2) |
O4—P1—C3 | 108.7 (2) | O15—P4—O13 | 111.3 (2) |
O7—P2—O6 | 110.3 (2) | O15—P4—O14 | 111.3 (2) |
O7—P2—O5 | 112.3 (3) | O13—P4—O14 | 104.43 (19) |
O6—P2—O5 | 104.8 (2) | O15—P4—C20 | 112.6 (2) |
O7—P2—C9 | 113.2 (2) | O13—P4—C20 | 108.3 (2) |
O6—P2—C9 | 108.1 (2) | O14—P4—C20 | 108.5 (2) |
O5—P2—C9 | 107.7 (2) | C14—O9—H9A | 109.5 |
C3—O1—H1A | 109.5 | C16—O11—P3 | 123.3 (3) |
C5—O3—P1 | 120.7 (3) | C15—O12—P3 | 121.2 (3) |
C4—O4—P1 | 122.3 (3) | C18—O13—P4 | 123.4 (3) |
C8—O5—P2 | 123.0 (3) | C19—O14—P4 | 119.6 (3) |
C7—O6—P2 | 122.0 (3) | C20—O16—H16A | 109.5 |
C9—O8—H8A | 109.5 | C14—C12—H12A | 109.5 |
C3—C1—H1B | 109.5 | C14—C12—H12B | 109.5 |
C3—C1—H1C | 109.5 | H12A—C12—H12B | 109.5 |
H1B—C1—H1C | 109.5 | C14—C12—H12C | 109.5 |
C3—C1—H1D | 109.5 | H12A—C12—H12C | 109.5 |
H1B—C1—H1D | 109.5 | H12B—C12—H12C | 109.5 |
H1C—C1—H1D | 109.5 | C14—C13—H13A | 109.5 |
C3—C2—H2B | 109.5 | C14—C13—H13B | 109.5 |
C3—C2—H2C | 109.5 | H13A—C13—H13B | 109.5 |
H2B—C2—H2C | 109.5 | C14—C13—H13C | 109.5 |
C3—C2—H2D | 109.5 | H13A—C13—H13C | 109.5 |
H2B—C2—H2D | 109.5 | H13B—C13—H13C | 109.5 |
H2C—C2—H2D | 109.5 | O9—C14—C12 | 108.8 (5) |
O1—C3—C2 | 111.2 (5) | O9—C14—C13 | 112.4 (5) |
O1—C3—C1 | 110.7 (5) | C12—C14—C13 | 110.8 (5) |
C2—C3—C1 | 111.7 (5) | O9—C14—P3 | 104.7 (4) |
O1—C3—P1 | 105.0 (3) | C12—C14—P3 | 109.4 (4) |
C2—C3—P1 | 108.5 (4) | C13—C14—P3 | 110.5 (4) |
C1—C3—P1 | 109.5 (4) | O12—C15—C17 | 110.6 (4) |
O4—C4—C6 | 111.3 (4) | O12—C15—H15B | 109.5 |
O4—C4—H4A | 109.4 | C17—C15—H15B | 109.5 |
C6—C4—H4A | 109.4 | O12—C15—H15C | 109.5 |
O4—C4—H4B | 109.4 | C17—C15—H15C | 109.5 |
C6—C4—H4B | 109.4 | H15B—C15—H15C | 108.1 |
H4A—C4—H4B | 108.0 | O11—C16—C17 | 111.5 (4) |
O3—C5—C6 | 111.7 (4) | O11—C16—H16B | 109.3 |
O3—C5—H5A | 109.3 | C17—C16—H16B | 109.3 |
C6—C5—H5A | 109.3 | O11—C16—H16C | 109.3 |
O3—C5—H5B | 109.3 | C17—C16—H16C | 109.3 |
C6—C5—H5B | 109.3 | H16B—C16—H16C | 108.0 |
H5A—C5—H5B | 107.9 | C19—C17—C15 | 105.6 (4) |
C5—C6—C7 | 106.4 (4) | C19—C17—C16 | 110.2 (4) |
C5—C6—C4 | 109.6 (4) | C15—C17—C16 | 109.8 (4) |
C7—C6—C4 | 110.2 (4) | C19—C17—C18 | 110.4 (4) |
C5—C6—C8 | 108.5 (4) | C15—C17—C18 | 108.8 (4) |
C7—C6—C8 | 110.3 (4) | C16—C17—C18 | 111.9 (4) |
C4—C6—C8 | 111.6 (4) | O13—C18—C17 | 112.3 (4) |
O6—C7—C6 | 112.4 (4) | O13—C18—H18A | 109.1 |
O6—C7—H7B | 109.1 | C17—C18—H18A | 109.1 |
C6—C7—H7B | 109.1 | O13—C18—H18B | 109.1 |
O6—C7—H7C | 109.1 | C17—C18—H18B | 109.1 |
C6—C7—H7C | 109.1 | H18A—C18—H18B | 107.9 |
H7B—C7—H7C | 107.9 | O14—C19—C17 | 110.6 (4) |
O5—C8—C6 | 112.2 (4) | O14—C19—H19A | 109.5 |
O5—C8—H8B | 109.2 | C17—C19—H19A | 109.5 |
C6—C8—H8B | 109.2 | O14—C19—H19B | 109.5 |
O5—C8—H8C | 109.2 | C17—C19—H19B | 109.5 |
C6—C8—H8C | 109.2 | H19A—C19—H19B | 108.1 |
H8B—C8—H8C | 107.9 | O16—C20—C22 | 111.8 (4) |
O8—C9—C11 | 106.6 (5) | O16—C20—C21 | 106.0 (4) |
O8—C9—C10 | 110.7 (4) | C22—C20—C21 | 112.1 (4) |
C11—C9—C10 | 111.8 (5) | O16—C20—P4 | 108.7 (3) |
O8—C9—P2 | 107.7 (3) | C22—C20—P4 | 109.3 (4) |
C11—C9—P2 | 109.2 (4) | C21—C20—P4 | 108.9 (4) |
C10—C9—P2 | 110.7 (4) | C20—C21—H21A | 109.5 |
C9—C10—H10A | 109.5 | C20—C21—H21B | 109.5 |
C9—C10—H10B | 109.5 | H21A—C21—H21B | 109.5 |
H10A—C10—H10B | 109.5 | C20—C21—H21C | 109.5 |
C9—C10—H10C | 109.5 | H21A—C21—H21C | 109.5 |
H10A—C10—H10C | 109.5 | H21B—C21—H21C | 109.5 |
H10B—C10—H10C | 109.5 | C20—C22—H22A | 109.5 |
C9—C11—H11A | 109.5 | C20—C22—H22B | 109.5 |
C9—C11—H11B | 109.5 | H22A—C22—H22B | 109.5 |
H11A—C11—H11B | 109.5 | C20—C22—H22C | 109.5 |
C9—C11—H11C | 109.5 | H22A—C22—H22C | 109.5 |
H11A—C11—H11C | 109.5 | H22B—C22—H22C | 109.5 |
H11B—C11—H11C | 109.5 | HWA—OW—HWB | 94 (3) |
O10—P3—O12 | 111.3 (2) | | |
| | | |
O2—P1—O3—C5 | 156.1 (4) | O10—P3—O11—C16 | −152.9 (4) |
O4—P1—O3—C5 | 34.6 (4) | O12—P3—O11—C16 | −32.5 (4) |
C3—P1—O3—C5 | −81.4 (4) | C14—P3—O11—C16 | 82.7 (4) |
O2—P1—O4—C4 | −155.1 (3) | O10—P3—O12—C15 | 156.0 (4) |
O3—P1—O4—C4 | −33.6 (4) | O11—P3—O12—C15 | 35.6 (4) |
C3—P1—O4—C4 | 81.4 (4) | C14—P3—O12—C15 | −79.3 (4) |
O7—P2—O5—C8 | −153.4 (4) | O15—P4—O13—C18 | −154.7 (3) |
O6—P2—O5—C8 | −33.6 (4) | O14—P4—O13—C18 | −34.5 (4) |
C9—P2—O5—C8 | 81.3 (4) | C20—P4—O13—C18 | 81.0 (4) |
O7—P2—O6—C7 | 157.1 (4) | O15—P4—O14—C19 | 160.7 (3) |
O5—P2—O6—C7 | 36.0 (4) | O13—P4—O14—C19 | 40.5 (4) |
C9—P2—O6—C7 | −78.6 (4) | C20—P4—O14—C19 | −74.8 (4) |
O2—P1—C3—O1 | 179.9 (3) | O10—P3—C14—O9 | −165.1 (3) |
O3—P1—C3—O1 | 57.4 (4) | O12—P3—C14—O9 | 71.2 (4) |
O4—P1—C3—O1 | −56.5 (4) | O11—P3—C14—O9 | −41.8 (4) |
O2—P1—C3—C2 | 61.0 (5) | O10—P3—C14—C12 | −48.6 (5) |
O3—P1—C3—C2 | −61.5 (5) | O12—P3—C14—C12 | −172.3 (4) |
O4—P1—C3—C2 | −175.5 (4) | O11—P3—C14—C12 | 74.7 (5) |
O2—P1—C3—C1 | −61.2 (5) | O10—P3—C14—C13 | 73.7 (5) |
O3—P1—C3—C1 | 176.3 (4) | O12—P3—C14—C13 | −50.0 (4) |
O4—P1—C3—C1 | 62.4 (5) | O11—P3—C14—C13 | −163.1 (4) |
P1—O4—C4—C6 | 47.3 (5) | P3—O12—C15—C17 | −52.1 (5) |
P1—O3—C5—C6 | −50.2 (6) | P3—O11—C16—C17 | 45.3 (5) |
O3—C5—C6—C7 | 177.3 (4) | O12—C15—C17—C19 | 177.4 (4) |
O3—C5—C6—C4 | 58.1 (6) | O12—C15—C17—C16 | 58.6 (5) |
O3—C5—C6—C8 | −64.1 (5) | O12—C15—C17—C18 | −64.1 (5) |
O4—C4—C6—C5 | −56.2 (6) | O11—C16—C17—C19 | −171.1 (4) |
O4—C4—C6—C7 | −173.1 (4) | O11—C16—C17—C15 | −55.2 (6) |
O4—C4—C6—C8 | 64.1 (5) | O11—C16—C17—C18 | 65.7 (5) |
P2—O6—C7—C6 | −50.3 (5) | P4—O13—C18—C17 | 43.4 (5) |
C5—C6—C7—O6 | 172.3 (4) | C19—C17—C18—O13 | −51.7 (6) |
C4—C6—C7—O6 | −68.9 (5) | C15—C17—C18—O13 | −167.1 (4) |
C8—C6—C7—O6 | 54.8 (5) | C16—C17—C18—O13 | 71.4 (5) |
P2—O5—C8—C6 | 45.0 (6) | P4—O14—C19—C17 | −56.1 (5) |
C5—C6—C8—O5 | −168.2 (4) | C15—C17—C19—O14 | 175.7 (4) |
C7—C6—C8—O5 | −51.9 (6) | C16—C17—C19—O14 | −65.8 (5) |
C4—C6—C8—O5 | 70.9 (5) | C18—C17—C19—O14 | 58.3 (5) |
O7—P2—C9—O8 | −174.3 (3) | O15—P4—C20—O16 | −167.8 (3) |
O6—P2—C9—O8 | 63.2 (4) | O13—P4—C20—O16 | −44.3 (4) |
O5—P2—C9—O8 | −49.6 (4) | O14—P4—C20—O16 | 68.5 (4) |
O7—P2—C9—C11 | 70.3 (5) | O15—P4—C20—C22 | −45.6 (4) |
O6—P2—C9—C11 | −52.2 (4) | O13—P4—C20—C22 | 77.9 (4) |
O5—P2—C9—C11 | −164.9 (4) | O14—P4—C20—C22 | −169.3 (3) |
O7—P2—C9—C10 | −53.1 (5) | O15—P4—C20—C21 | 77.1 (4) |
O6—P2—C9—C10 | −175.6 (4) | O13—P4—C20—C21 | −159.4 (3) |
O5—P2—C9—C10 | 71.6 (4) | O14—P4—C20—C21 | −46.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
OW—HWA···O15i | 0.79 (6) | 2.06 (7) | 2.823 (7) | 163 (6) |
O1—H1A···O15 | 0.82 | 2.00 | 2.818 (5) | 175 |
OW—HWB···O7ii | 0.82 (6) | 2.34 (6) | 2.706 (8) | 108 (5) |
O8—H8A···O2iii | 0.82 | 1.97 | 2.785 (5) | 175 |
O9—H9A···OW | 0.82 | 2.27 | 2.599 (8) | 105 |
O16—H16A···O10iv | 0.82 | 1.90 | 2.716 (5) | 179 |
C5—H5A···O8v | 0.97 | 2.44 | 3.405 (7) | 173 |
C5—H5B···O1 | 0.97 | 2.51 | 3.106 (7) | 120 |
C7—H7C···O2vi | 0.97 | 2.47 | 3.332 (7) | 148 |
C8—H8B···O8 | 0.97 | 2.59 | 3.155 (7) | 117 |
C16—H16B···O9 | 0.97 | 2.50 | 3.056 (7) | 117 |
Symmetry codes: (i) −x+2, −y, −z; (ii) x, y, z−1; (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. |