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In the title compound, C
34H
38O
8P
2·2.5H
2O, intermolecular interactions consist of strong O—H(water)
O hydrogen bonds, as well as C—H
O interactions.
Supporting information
CCDC reference: 608348
Key indicators
- Single-crystal X-ray study
- T = 168 K
- Mean (C-C) = 0.018 Å
- H-atom completeness 98%
- R factor = 0.066
- wR factor = 0.186
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level A
RINTA01_ALERT_3_A The value of Rint is greater than 0.20
Rint given 0.244
| Author Response:
A full quadrant of data was collected from a weakly diffracting crystal;
an analysis of equivalent reflections shows that the weakest data is
not significantly different, but numerically biases this Rint total.
|
PLAT020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.24
| Author Response:
See response to RINTA01_I
|
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.73
| Author Response: ...
Weak data was obtained and examined and processed after collection,
using equivalent data comparisons, as described
in Exptl_special_details.
|
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.629 0.965
Tmin(prime) and Tmax expected: 0.926 0.965
RR(prime) = 0.679
Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
| Author Response: ...
The best crystals that could be obtained diffracted weakly, consistent
with their maximum size and occluded water.
|
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.68
| Author Response: ...
The correction is biased by the actual shape of the crystal and
possibly by buildup of ice on the crystal during data collection.
|
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 18
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.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C11 -C16 1.37 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.20
Alert level G
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:C34 H43 O10.5 P2
Atom count from the _atom_site data: C34 H42 O10.5 P2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 8
From the CIF: _chemical_formula_sum C34 H43 O10.5 P2
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 272.00 272.00 0.00
H 344.00 336.00 8.00
O 84.00 84.00 0.00
P 16.00 16.00 0.00
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 26.05
From the CIF: _reflns_number_total 4694
From the CIF: _diffrn_reflns_limit_ max hkl 13. 14. 35.
From the CIF: _diffrn_reflns_limit_ min hkl -16. -15. -34.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 16. 16. 48.
Calculated minimum hkl -16. -16. -48.
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 26.05
From the CIF: _reflns_number_total 4694
Count of symmetry unique reflns 3911
Completeness (_total/calc) 120.02%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 783
Fraction of Friedel pairs measured 0.200
Are heavy atom types Z>Si present yes
3 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
8 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
7 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
1D-1,2,5,6-Tetra-
O-methyl-3,4-di-O-phosphinoyl-
chiro-inositol
2.5-hydrate
top
Crystal data top
C34H38O8P2·2.5H2O | Dx = 1.333 Mg m−3 |
Mr = 680.62 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41212 | Cell parameters from 6000 reflections |
Hall symbol: P4abw 2nw | θ = 2.8–25.4° |
a = 13.115 (5) Å | µ = 0.19 mm−1 |
c = 39.441 (15) Å | T = 168 K |
V = 6784 (4) Å3 | Plate, colourless |
Z = 8 | 0.40 × 0.37 × 0.19 mm |
F(000) = 2888 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 4694 independent reflections |
Radiation source: fine-focus sealed tube | 1666 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.245 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.1°, θmin = 2.2° |
φ and ω scans | h = −16→13 |
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996) | k = −15→14 |
Tmin = 0.629, Tmax = 0.965 | l = −34→35 |
22268 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.0828P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.186 | (Δ/σ)max < 0.001 |
S = 0.85 | Δρmax = 0.36 e Å−3 |
4694 reflections | Δρmin = −0.31 e Å−3 |
437 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.061 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 783 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (2) |
Special details top
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the
data collection and analyzing duplicate reflections. The standard 0.8 mm
diameter collimator was used. Examination of the full sphere of collected data showed that a section of data
taken late in the collection (with 28=<l<40) was badly measured probably from
crystal shifting (from consideration of equivalent reflections & VERY high
statistical errors). This data was the major contributor to the high
R(int) value of 0.44. Removal of this block of data gave an
R(int) of 0.25. It was also noted at the time that an excessive buildup
of ice occurred (a fault in the gas supply). Apart from one low angle reflection (0,1,2), 11 other outlier relections were
identified in the final Fo/Fc table statistics with Fo >> Fc
by factors of 1.5–2.0. In these cases, equivalent reflections for these data
generally agreed indicating either an ice scattering effect, or possibly a
partial crystal fragment. With these reflections excluded, anisotropic thermal
parameter refinement was stable, even though the change in R1 factor
is only from 0.0703 (1676 data) to 0.0665 (1666). The outlier data are:
(0,1,2); (0,2,0,); (0,2,1); (1,1,12);(0,9,19); (-1,3,4); (1,3,4); (0,1,3);
(-1,3,2); (1,3,2); (1,1,9) & (2,3,0). One of the water H atoms could not be refined. It is probable that some data is
still affected by overlap; however (apart from improving the R
factors), the chosen conservative ratio was considered a reasonable if rather
arbitrary compromise. The full dataset is available from the authors on
request. |
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 | 0.4353 (2) | 0.3997 (2) | 0.15576 (9) | 0.0595 (10) | |
P2 | 0.0957 (2) | 0.4327 (2) | 0.12525 (8) | 0.0588 (10) | |
O1 | 0.3315 (4) | 0.3670 (4) | 0.17279 (16) | 0.0534 (19) | |
O2 | 0.4008 (5) | 0.4088 (5) | 0.2389 (2) | 0.072 (2) | |
O3 | 0.2345 (5) | 0.5383 (6) | 0.25888 (18) | 0.074 (2) | |
O4 | 0.1025 (5) | 0.3019 (6) | 0.24559 (19) | 0.066 (2) | |
O5 | −0.0034 (5) | 0.4226 (5) | 0.20206 (17) | 0.066 (2) | |
O6 | 0.1539 (4) | 0.4722 (4) | 0.15765 (18) | 0.0536 (19) | |
O7 | 0.4622 (5) | 0.5090 (5) | 0.15799 (18) | 0.069 (2) | |
O8 | 0.0903 (5) | 0.3202 (5) | 0.12167 (16) | 0.066 (2) | |
O1W | 0.5591 (6) | 0.6912 (5) | 0.0500 (2) | 0.091 (3) | |
H1W1 | 0.543 (9) | 0.753 (4) | 0.044 (3) | 0.109* | |
O2W | 0.5387 (6) | 0.6642 (6) | 0.1194 (2) | 0.086 (3) | |
H2W1 | 0.500 (7) | 0.613 (4) | 0.125 (3) | 0.103* | |
H2W2 | 0.504 (7) | 0.710 (5) | 0.132 (2) | 0.103* | |
O3W | −0.0416 (7) | 0.0416 (7) | 0.2500 | 0.108 (5) | |
H3W | −0.084 (9) | 0.062 (9) | 0.267 (3) | 0.130* | |
C1 | 0.2743 (7) | 0.4274 (8) | 0.1974 (3) | 0.057 (3) | |
H1 | 0.2925 | 0.5013 | 0.1959 | 0.068* | |
C2 | 0.2969 (8) | 0.3843 (8) | 0.2323 (3) | 0.059 (3) | |
H2 | 0.2878 | 0.3086 | 0.2322 | 0.071* | |
C3 | 0.2294 (7) | 0.4305 (9) | 0.2580 (3) | 0.057 (3) | |
H3 | 0.2448 | 0.4017 | 0.2809 | 0.069* | |
C4 | 0.1186 (8) | 0.4095 (9) | 0.2485 (3) | 0.065 (3) | |
H4 | 0.0716 | 0.4393 | 0.2658 | 0.078* | |
C5 | 0.0940 (8) | 0.4498 (7) | 0.2142 (3) | 0.053 (3) | |
H5 | 0.0992 | 0.5259 | 0.2147 | 0.064* | |
C6 | 0.1664 (7) | 0.4092 (8) | 0.1871 (3) | 0.056 (3) | |
H6 | 0.1534 | 0.3357 | 0.1820 | 0.068* | |
C7 | 0.4449 (8) | 0.3473 (10) | 0.2632 (3) | 0.097 (4) | |
H7A | 0.4063 | 0.3530 | 0.2844 | 0.116* | |
H7B | 0.5154 | 0.3690 | 0.2671 | 0.116* | |
H7C | 0.4441 | 0.2764 | 0.2555 | 0.116* | |
C8 | 0.3005 (8) | 0.5782 (9) | 0.2843 (3) | 0.095 (4) | |
H8A | 0.2747 | 0.5591 | 0.3068 | 0.114* | |
H8B | 0.3029 | 0.6526 | 0.2825 | 0.114* | |
H8C | 0.3691 | 0.5502 | 0.2813 | 0.114* | |
C9 | 0.0942 (9) | 0.2570 (8) | 0.2771 (4) | 0.095 (4) | |
H9A | 0.1593 | 0.2628 | 0.2891 | 0.114* | |
H9B | 0.0765 | 0.1849 | 0.2744 | 0.114* | |
H9C | 0.0407 | 0.2915 | 0.2902 | 0.114* | |
C10 | −0.0829 (8) | 0.4886 (9) | 0.2134 (3) | 0.096 (4) | |
H10A | −0.1018 | 0.4707 | 0.2367 | 0.115* | |
H10B | −0.1424 | 0.4810 | 0.1986 | 0.115* | |
H10C | −0.0591 | 0.5594 | 0.2127 | 0.115* | |
C11 | 0.5288 (8) | 0.3200 (7) | 0.1744 (3) | 0.050 (3) | |
C12 | 0.6278 (10) | 0.3495 (8) | 0.1776 (3) | 0.069 (3) | |
H12 | 0.6464 | 0.4161 | 0.1704 | 0.083* | |
C13 | 0.7012 (10) | 0.2878 (13) | 0.1905 (3) | 0.090 (4) | |
H13 | 0.7696 | 0.3109 | 0.1924 | 0.108* | |
C14 | 0.6752 (12) | 0.1927 (11) | 0.2007 (3) | 0.078 (4) | |
H14 | 0.7259 | 0.1484 | 0.2096 | 0.094* | |
C15 | 0.5769 (11) | 0.1603 (10) | 0.1983 (3) | 0.077 (4) | |
H15 | 0.5592 | 0.0939 | 0.2059 | 0.092* | |
C16 | 0.5026 (8) | 0.2233 (9) | 0.1849 (2) | 0.060 (3) | |
H16 | 0.4342 | 0.2002 | 0.1830 | 0.073* | |
C21 | 0.4182 (10) | 0.3551 (9) | 0.1137 (3) | 0.065 (4) | |
C22 | 0.4731 (10) | 0.3995 (11) | 0.0880 (5) | 0.092 (4) | |
H22 | 0.5213 | 0.4519 | 0.0924 | 0.111* | |
C23 | 0.4552 (12) | 0.3644 (12) | 0.0554 (5) | 0.093 (5) | |
H23 | 0.4931 | 0.3937 | 0.0374 | 0.111* | |
C24 | 0.3861 (13) | 0.2900 (13) | 0.0479 (4) | 0.087 (5) | |
H24 | 0.3772 | 0.2674 | 0.0252 | 0.104* | |
C25 | 0.3322 (11) | 0.2504 (11) | 0.0725 (5) | 0.089 (5) | |
H25 | 0.2833 | 0.1994 | 0.0673 | 0.107* | |
C26 | 0.3444 (9) | 0.2808 (9) | 0.1065 (4) | 0.064 (3) | |
H26 | 0.3040 | 0.2519 | 0.1240 | 0.077* | |
C31 | 0.1639 (8) | 0.4929 (7) | 0.0927 (4) | 0.054 (3) | |
C32 | 0.2448 (9) | 0.5589 (8) | 0.0984 (4) | 0.075 (4) | |
H32 | 0.2639 | 0.5755 | 0.1210 | 0.090* | |
C33 | 0.2979 (9) | 0.6008 (10) | 0.0714 (5) | 0.085 (5) | |
H33 | 0.3550 | 0.6436 | 0.0755 | 0.102* | |
C34 | 0.2683 (10) | 0.5806 (11) | 0.0392 (4) | 0.093 (5) | |
H34 | 0.3026 | 0.6118 | 0.0207 | 0.111* | |
C35 | 0.1900 (11) | 0.5164 (11) | 0.0334 (3) | 0.075 (4) | |
H35 | 0.1705 | 0.5035 | 0.0106 | 0.090* | |
C36 | 0.1369 (9) | 0.4685 (9) | 0.0591 (4) | 0.069 (4) | |
H36 | 0.0842 | 0.4210 | 0.0543 | 0.083* | |
C41 | −0.0279 (8) | 0.4867 (9) | 0.1261 (3) | 0.061 (3) | |
C42 | −0.0417 (8) | 0.5879 (9) | 0.1362 (3) | 0.071 (3) | |
H42 | 0.0150 | 0.6272 | 0.1436 | 0.086* | |
C43 | −0.1351 (10) | 0.6296 (10) | 0.1355 (3) | 0.088 (4) | |
H43 | −0.1432 | 0.7000 | 0.1405 | 0.105* | |
C44 | −0.2202 (9) | 0.5709 (14) | 0.1276 (3) | 0.092 (5) | |
H44 | −0.2866 | 0.5996 | 0.1288 | 0.111* | |
C45 | −0.2072 (10) | 0.4715 (12) | 0.1180 (3) | 0.084 (4) | |
H45 | −0.2640 | 0.4311 | 0.1114 | 0.101* | |
C46 | −0.1079 (9) | 0.4301 (9) | 0.1181 (2) | 0.070 (3) | |
H46 | −0.0983 | 0.3605 | 0.1122 | 0.084* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.055 (2) | 0.053 (2) | 0.070 (3) | 0.0045 (15) | 0.0070 (18) | 0.0010 (18) |
P2 | 0.0490 (18) | 0.059 (2) | 0.069 (3) | −0.0059 (15) | 0.0008 (18) | 0.0051 (19) |
O1 | 0.048 (4) | 0.053 (4) | 0.059 (5) | 0.000 (3) | 0.010 (4) | −0.003 (4) |
O2 | 0.051 (5) | 0.094 (6) | 0.072 (6) | 0.008 (5) | −0.008 (4) | −0.001 (5) |
O3 | 0.074 (5) | 0.071 (6) | 0.076 (6) | 0.004 (4) | −0.017 (5) | −0.014 (5) |
O4 | 0.086 (6) | 0.068 (6) | 0.045 (6) | 0.002 (4) | 0.000 (5) | 0.010 (4) |
O5 | 0.052 (5) | 0.075 (5) | 0.071 (6) | 0.001 (4) | 0.010 (4) | 0.001 (4) |
O6 | 0.055 (4) | 0.049 (4) | 0.057 (6) | −0.001 (3) | −0.012 (4) | −0.011 (4) |
O7 | 0.092 (6) | 0.037 (4) | 0.080 (6) | 0.001 (4) | 0.003 (4) | −0.004 (4) |
O8 | 0.078 (5) | 0.049 (5) | 0.071 (6) | 0.002 (4) | −0.001 (4) | 0.002 (4) |
O1W | 0.076 (6) | 0.085 (6) | 0.112 (7) | 0.007 (5) | −0.006 (5) | 0.011 (6) |
O2W | 0.078 (6) | 0.059 (5) | 0.121 (8) | 0.009 (4) | 0.025 (5) | 0.002 (5) |
O3W | 0.114 (7) | 0.114 (7) | 0.098 (13) | 0.032 (8) | 0.010 (7) | 0.010 (7) |
C1 | 0.057 (8) | 0.064 (8) | 0.049 (10) | 0.015 (6) | 0.000 (7) | −0.013 (7) |
C2 | 0.056 (8) | 0.072 (8) | 0.050 (10) | −0.001 (6) | 0.004 (7) | −0.001 (7) |
C3 | 0.044 (7) | 0.088 (10) | 0.040 (9) | 0.010 (7) | −0.008 (6) | 0.003 (7) |
C4 | 0.076 (9) | 0.060 (9) | 0.061 (11) | 0.004 (7) | −0.009 (7) | 0.002 (7) |
C5 | 0.047 (7) | 0.056 (7) | 0.058 (10) | 0.001 (6) | 0.002 (7) | −0.017 (7) |
C6 | 0.046 (7) | 0.048 (7) | 0.075 (10) | 0.014 (6) | 0.013 (7) | 0.017 (7) |
C7 | 0.065 (8) | 0.141 (12) | 0.084 (11) | 0.028 (8) | −0.026 (8) | −0.015 (10) |
C8 | 0.078 (8) | 0.123 (11) | 0.085 (10) | −0.027 (8) | −0.008 (8) | −0.056 (9) |
C9 | 0.098 (11) | 0.081 (9) | 0.106 (13) | 0.003 (8) | 0.001 (9) | 0.008 (9) |
C10 | 0.068 (8) | 0.119 (11) | 0.101 (11) | 0.036 (9) | 0.001 (8) | −0.034 (9) |
C11 | 0.051 (8) | 0.027 (7) | 0.074 (9) | 0.009 (5) | −0.004 (6) | −0.002 (6) |
C12 | 0.071 (9) | 0.057 (8) | 0.080 (10) | −0.008 (8) | 0.022 (8) | −0.016 (7) |
C13 | 0.058 (9) | 0.114 (13) | 0.097 (12) | 0.018 (10) | −0.015 (8) | −0.033 (10) |
C14 | 0.101 (13) | 0.082 (11) | 0.053 (10) | 0.036 (9) | −0.008 (8) | 0.007 (8) |
C15 | 0.067 (9) | 0.084 (9) | 0.079 (11) | 0.011 (9) | −0.004 (8) | −0.005 (8) |
C16 | 0.056 (8) | 0.071 (9) | 0.055 (9) | 0.018 (7) | 0.004 (7) | −0.009 (7) |
C21 | 0.073 (9) | 0.053 (8) | 0.070 (12) | 0.006 (7) | 0.007 (8) | −0.006 (8) |
C22 | 0.091 (10) | 0.102 (11) | 0.085 (14) | 0.009 (9) | 0.025 (11) | 0.015 (12) |
C23 | 0.100 (12) | 0.092 (12) | 0.086 (17) | 0.023 (9) | 0.004 (11) | 0.017 (10) |
C24 | 0.097 (13) | 0.119 (14) | 0.044 (13) | 0.047 (10) | 0.002 (11) | −0.008 (11) |
C25 | 0.084 (11) | 0.130 (13) | 0.054 (14) | 0.010 (9) | −0.013 (10) | −0.034 (11) |
C26 | 0.065 (9) | 0.066 (8) | 0.062 (13) | 0.018 (7) | −0.012 (7) | 0.005 (7) |
C31 | 0.048 (7) | 0.041 (7) | 0.073 (11) | 0.000 (5) | 0.017 (7) | 0.012 (7) |
C32 | 0.063 (8) | 0.052 (8) | 0.110 (13) | 0.003 (7) | −0.013 (9) | −0.006 (8) |
C33 | 0.056 (8) | 0.096 (10) | 0.103 (14) | −0.020 (7) | 0.004 (10) | 0.039 (11) |
C34 | 0.061 (10) | 0.111 (13) | 0.106 (16) | 0.016 (10) | 0.018 (10) | 0.032 (11) |
C35 | 0.081 (10) | 0.091 (10) | 0.052 (11) | 0.020 (8) | −0.002 (9) | 0.006 (9) |
C36 | 0.065 (8) | 0.081 (9) | 0.062 (12) | 0.017 (7) | −0.010 (9) | −0.011 (9) |
C41 | 0.045 (8) | 0.060 (8) | 0.077 (10) | 0.007 (6) | 0.005 (7) | −0.001 (7) |
C42 | 0.053 (8) | 0.083 (10) | 0.078 (10) | 0.012 (7) | 0.006 (6) | 0.018 (8) |
C43 | 0.072 (10) | 0.100 (11) | 0.090 (12) | 0.024 (9) | 0.016 (8) | 0.038 (8) |
C44 | 0.053 (9) | 0.160 (16) | 0.063 (11) | −0.007 (11) | 0.000 (7) | 0.064 (11) |
C45 | 0.078 (11) | 0.118 (12) | 0.057 (10) | 0.004 (9) | 0.012 (7) | 0.025 (9) |
C46 | 0.066 (9) | 0.099 (9) | 0.044 (9) | −0.015 (9) | −0.001 (7) | 0.000 (7) |
Geometric parameters (Å, º) top
P1—O7 | 1.478 (6) | C10—H10C | 0.9800 |
P1—O1 | 1.577 (6) | C11—C12 | 1.360 (13) |
P1—C11 | 1.771 (9) | C11—C16 | 1.378 (12) |
P1—C21 | 1.773 (12) | C12—C13 | 1.357 (14) |
P2—O8 | 1.485 (6) | C12—H12 | 0.9500 |
P2—O6 | 1.576 (6) | C13—C14 | 1.353 (16) |
P2—C31 | 1.753 (10) | C13—H13 | 0.9500 |
P2—C41 | 1.769 (10) | C14—C15 | 1.361 (14) |
O1—C1 | 1.460 (10) | C14—H14 | 0.9500 |
O2—C7 | 1.381 (11) | C15—C16 | 1.383 (13) |
O2—C2 | 1.424 (11) | C15—H15 | 0.9500 |
O3—C3 | 1.415 (11) | C16—H16 | 0.9500 |
O3—C8 | 1.425 (11) | C21—C22 | 1.371 (14) |
O4—C9 | 1.380 (12) | C21—C26 | 1.402 (14) |
O4—C4 | 1.432 (11) | C22—C23 | 1.387 (15) |
O5—C5 | 1.410 (10) | C22—H22 | 0.9500 |
O5—C10 | 1.426 (10) | C23—C24 | 1.365 (17) |
O6—C6 | 1.436 (10) | C23—H23 | 0.9500 |
O1W—H1W1 | 0.86 (3) | C24—C25 | 1.310 (16) |
O2W—H2W1 | 0.87 (7) | C24—H24 | 0.9500 |
O2W—H2W2 | 0.90 (8) | C25—C26 | 1.407 (15) |
O3W—H3W | 0.92 (11) | C25—H25 | 0.9500 |
C1—C6 | 1.491 (12) | C26—H26 | 0.9500 |
C1—C2 | 1.518 (12) | C31—C32 | 1.388 (13) |
C1—H1 | 1.0000 | C31—C36 | 1.408 (13) |
C2—C3 | 1.474 (12) | C32—C33 | 1.386 (14) |
C2—H2 | 1.0000 | C32—H32 | 0.9500 |
C3—C4 | 1.526 (12) | C33—C34 | 1.354 (15) |
C3—H3 | 1.0000 | C33—H33 | 0.9500 |
C4—C5 | 1.490 (12) | C34—C35 | 1.347 (16) |
C4—H4 | 1.0000 | C34—H34 | 0.9500 |
C5—C6 | 1.524 (12) | C35—C36 | 1.380 (14) |
C5—H5 | 1.0000 | C35—H35 | 0.9500 |
C6—H6 | 1.0000 | C36—H36 | 0.9500 |
C7—H7A | 0.9800 | C41—C46 | 1.324 (12) |
C7—H7B | 0.9800 | C41—C42 | 1.398 (13) |
C7—H7C | 0.9800 | C42—C43 | 1.341 (13) |
C8—H8A | 0.9800 | C42—H42 | 0.9500 |
C8—H8B | 0.9800 | C43—C44 | 1.392 (15) |
C8—H8C | 0.9800 | C43—H43 | 0.9500 |
C9—H9A | 0.9800 | C44—C45 | 1.367 (15) |
C9—H9B | 0.9800 | C44—H44 | 0.9500 |
C9—H9C | 0.9800 | C45—C46 | 1.411 (14) |
C10—H10A | 0.9800 | C45—H45 | 0.9500 |
C10—H10B | 0.9800 | C46—H46 | 0.9500 |
| | | |
O7—P1—O1 | 116.4 (4) | O5—C10—H10C | 109.5 |
O7—P1—C11 | 112.4 (5) | H10A—C10—H10C | 109.5 |
O1—P1—C11 | 105.1 (5) | H10B—C10—H10C | 109.5 |
O7—P1—C21 | 113.9 (5) | C12—C11—C16 | 118.2 (10) |
O1—P1—C21 | 101.5 (6) | C12—C11—P1 | 122.2 (10) |
C11—P1—C21 | 106.3 (5) | C16—C11—P1 | 119.6 (9) |
O8—P2—O6 | 115.3 (4) | C13—C12—C11 | 122.8 (11) |
O8—P2—C31 | 113.7 (5) | C13—C12—H12 | 118.6 |
O6—P2—C31 | 101.5 (6) | C11—C12—H12 | 118.6 |
O8—P2—C41 | 110.8 (5) | C14—C13—C12 | 118.9 (13) |
O6—P2—C41 | 107.3 (5) | C14—C13—H13 | 120.6 |
C31—P2—C41 | 107.5 (5) | C12—C13—H13 | 120.6 |
C1—O1—P1 | 125.3 (6) | C13—C14—C15 | 120.3 (13) |
C7—O2—C2 | 113.3 (9) | C13—C14—H14 | 119.8 |
C3—O3—C8 | 114.4 (9) | C15—C14—H14 | 119.8 |
C9—O4—C4 | 111.1 (9) | C14—C15—C16 | 120.5 (12) |
C5—O5—C10 | 113.7 (7) | C14—C15—H15 | 119.7 |
C6—O6—P2 | 121.5 (6) | C16—C15—H15 | 119.7 |
H2W1—O2W—H2W2 | 95 (8) | C11—C16—C15 | 119.3 (10) |
O1—C1—C6 | 102.7 (8) | C11—C16—H16 | 120.4 |
O1—C1—C2 | 107.5 (8) | C15—C16—H16 | 120.4 |
C6—C1—C2 | 111.8 (9) | C22—C21—C26 | 120.5 (12) |
O1—C1—H1 | 111.5 | C22—C21—P1 | 119.0 (13) |
C6—C1—H1 | 111.5 | C26—C21—P1 | 120.4 (12) |
C2—C1—H1 | 111.5 | C21—C22—C23 | 117.1 (15) |
O2—C2—C3 | 111.0 (9) | C21—C22—H22 | 121.5 |
O2—C2—C1 | 105.5 (9) | C23—C22—H22 | 121.5 |
C3—C2—C1 | 110.6 (9) | C24—C23—C22 | 123.5 (16) |
O2—C2—H2 | 109.9 | C24—C23—H23 | 118.2 |
C3—C2—H2 | 109.9 | C22—C23—H23 | 118.2 |
C1—C2—H2 | 109.9 | C25—C24—C23 | 118.7 (16) |
O3—C3—C2 | 113.6 (9) | C25—C24—H24 | 120.7 |
O3—C3—C4 | 103.4 (8) | C23—C24—H24 | 120.7 |
C2—C3—C4 | 109.3 (9) | C24—C25—C26 | 122.3 (15) |
O3—C3—H3 | 110.1 | C24—C25—H25 | 118.9 |
C2—C3—H3 | 110.1 | C26—C25—H25 | 118.9 |
C4—C3—H3 | 110.1 | C21—C26—C25 | 117.9 (12) |
O4—C4—C5 | 104.2 (9) | C21—C26—H26 | 121.0 |
O4—C4—C3 | 109.8 (9) | C25—C26—H26 | 121.0 |
C5—C4—C3 | 111.3 (9) | C32—C31—C36 | 119.2 (11) |
O4—C4—H4 | 110.5 | C32—C31—P2 | 123.5 (13) |
C5—C4—H4 | 110.5 | C36—C31—P2 | 117.3 (11) |
C3—C4—H4 | 110.5 | C33—C32—C31 | 120.3 (12) |
O5—C5—C4 | 114.5 (9) | C33—C32—H32 | 119.8 |
O5—C5—C6 | 103.9 (8) | C31—C32—H32 | 119.8 |
C4—C5—C6 | 112.2 (9) | C34—C33—C32 | 120.0 (13) |
O5—C5—H5 | 108.7 | C34—C33—H33 | 120.0 |
C4—C5—H5 | 108.7 | C32—C33—H33 | 120.0 |
C6—C5—H5 | 108.7 | C35—C34—C33 | 119.9 (14) |
O6—C6—C1 | 103.7 (8) | C35—C34—H34 | 120.0 |
O6—C6—C5 | 107.1 (8) | C33—C34—H34 | 120.0 |
C1—C6—C5 | 110.2 (9) | C34—C35—C36 | 123.1 (14) |
O6—C6—H6 | 111.8 | C34—C35—H35 | 118.5 |
C1—C6—H6 | 111.8 | C36—C35—H35 | 118.5 |
C5—C6—H6 | 111.8 | C35—C36—C31 | 117.3 (12) |
O2—C7—H7A | 109.5 | C35—C36—H36 | 121.3 |
O2—C7—H7B | 109.5 | C31—C36—H36 | 121.3 |
H7A—C7—H7B | 109.5 | C46—C41—C42 | 119.9 (10) |
O2—C7—H7C | 109.5 | C46—C41—P2 | 119.8 (10) |
H7A—C7—H7C | 109.5 | C42—C41—P2 | 120.3 (9) |
H7B—C7—H7C | 109.5 | C43—C42—C41 | 119.9 (11) |
O3—C8—H8A | 109.5 | C43—C42—H42 | 120.0 |
O3—C8—H8B | 109.5 | C41—C42—H42 | 120.0 |
H8A—C8—H8B | 109.5 | C42—C43—C44 | 120.8 (13) |
O3—C8—H8C | 109.5 | C42—C43—H43 | 119.6 |
H8A—C8—H8C | 109.5 | C44—C43—H43 | 119.6 |
H8B—C8—H8C | 109.5 | C45—C44—C43 | 119.3 (14) |
O4—C9—H9A | 109.5 | C45—C44—H44 | 120.4 |
O4—C9—H9B | 109.5 | C43—C44—H44 | 120.4 |
H9A—C9—H9B | 109.5 | C44—C45—C46 | 118.8 (13) |
O4—C9—H9C | 109.5 | C44—C45—H45 | 120.6 |
H9A—C9—H9C | 109.5 | C46—C45—H45 | 120.6 |
H9B—C9—H9C | 109.5 | C41—C46—C45 | 121.0 (12) |
O5—C10—H10A | 109.5 | C41—C46—H46 | 119.5 |
O5—C10—H10B | 109.5 | C45—C46—H46 | 119.5 |
H10A—C10—H10B | 109.5 | | |
| | | |
O7—P1—O1—C1 | −16.7 (9) | P1—C11—C12—C13 | −177.3 (9) |
C11—P1—O1—C1 | 108.5 (8) | C11—C12—C13—C14 | 0.1 (18) |
C21—P1—O1—C1 | −140.9 (8) | C12—C13—C14—C15 | −0.7 (19) |
O8—P2—O6—C6 | −22.3 (8) | C13—C14—C15—C16 | 1.1 (18) |
C31—P2—O6—C6 | −145.7 (7) | C12—C11—C16—C15 | 0.2 (15) |
C41—P2—O6—C6 | 101.7 (7) | P1—C11—C16—C15 | 177.7 (8) |
P1—O1—C1—C6 | 141.2 (7) | C14—C15—C16—C11 | −0.8 (16) |
P1—O1—C1—C2 | −100.7 (9) | O7—P1—C21—C22 | 30.6 (11) |
C7—O2—C2—C3 | 81.4 (11) | O1—P1—C21—C22 | 156.5 (9) |
C7—O2—C2—C1 | −158.7 (9) | C11—P1—C21—C22 | −93.8 (10) |
O1—C1—C2—O2 | 69.0 (9) | O7—P1—C21—C26 | −145.0 (8) |
C6—C1—C2—O2 | −179.0 (8) | O1—P1—C21—C26 | −19.1 (9) |
O1—C1—C2—C3 | −170.9 (8) | C11—P1—C21—C26 | 90.6 (9) |
C6—C1—C2—C3 | −58.9 (11) | C26—C21—C22—C23 | −2.6 (17) |
C8—O3—C3—C2 | −97.2 (10) | P1—C21—C22—C23 | −178.2 (9) |
C8—O3—C3—C4 | 144.5 (9) | C21—C22—C23—C24 | 0.7 (19) |
O2—C2—C3—O3 | 60.8 (12) | C22—C23—C24—C25 | 1 (2) |
C1—C2—C3—O3 | −56.0 (11) | C23—C24—C25—C26 | −1 (2) |
O2—C2—C3—C4 | 175.6 (9) | C22—C21—C26—C25 | 2.8 (16) |
C1—C2—C3—C4 | 58.9 (12) | P1—C21—C26—C25 | 178.2 (8) |
C9—O4—C4—C5 | −163.1 (8) | C24—C25—C26—C21 | −0.9 (18) |
C9—O4—C4—C3 | 77.6 (11) | O8—P2—C31—C32 | −126.1 (8) |
O3—C3—C4—O4 | 178.3 (8) | O6—P2—C31—C32 | −1.7 (9) |
C2—C3—C4—O4 | 57.0 (12) | C41—P2—C31—C32 | 110.7 (9) |
O3—C3—C4—C5 | 63.5 (11) | O8—P2—C31—C36 | 51.0 (9) |
C2—C3—C4—C5 | −57.8 (12) | O6—P2—C31—C36 | 175.4 (7) |
C10—O5—C5—C4 | 84.6 (11) | C41—P2—C31—C36 | −72.1 (9) |
C10—O5—C5—C6 | −152.8 (9) | C36—C31—C32—C33 | 0.4 (15) |
O4—C4—C5—O5 | 54.6 (10) | P2—C31—C32—C33 | 177.5 (9) |
C3—C4—C5—O5 | 172.8 (9) | C31—C32—C33—C34 | 2.7 (18) |
O4—C4—C5—C6 | −63.4 (10) | C32—C33—C34—C35 | −3 (2) |
C3—C4—C5—C6 | 54.8 (12) | C33—C34—C35—C36 | −0.1 (19) |
P2—O6—C6—C1 | 137.3 (7) | C34—C35—C36—C31 | 3.1 (17) |
P2—O6—C6—C5 | −106.2 (8) | C32—C31—C36—C35 | −3.2 (14) |
O1—C1—C6—O6 | −76.7 (9) | P2—C31—C36—C35 | 179.5 (8) |
C2—C1—C6—O6 | 168.3 (8) | O8—P2—C41—C46 | −11.3 (11) |
O1—C1—C6—C5 | 169.0 (8) | O6—P2—C41—C46 | −137.9 (9) |
C2—C1—C6—C5 | 54.0 (12) | C31—P2—C41—C46 | 113.6 (10) |
O5—C5—C6—O6 | 71.0 (9) | O8—P2—C41—C42 | 166.8 (8) |
C4—C5—C6—O6 | −164.9 (8) | O6—P2—C41—C42 | 40.2 (10) |
O5—C5—C6—C1 | −176.9 (8) | C31—P2—C41—C42 | −68.3 (11) |
C4—C5—C6—C1 | −52.8 (12) | C46—C41—C42—C43 | −4.5 (17) |
O7—P1—C11—C12 | −24.5 (10) | P2—C41—C42—C43 | 177.4 (8) |
O1—P1—C11—C12 | −152.1 (8) | C41—C42—C43—C44 | 5.4 (17) |
C21—P1—C11—C12 | 100.8 (10) | C42—C43—C44—C45 | −4.7 (19) |
O7—P1—C11—C16 | 158.0 (8) | C43—C44—C45—C46 | 3.0 (19) |
O1—P1—C11—C16 | 30.4 (9) | C42—C41—C46—C45 | 2.9 (17) |
C21—P1—C11—C16 | −76.7 (10) | P2—C41—C46—C45 | −179.0 (8) |
C16—C11—C12—C13 | 0.2 (16) | C44—C45—C46—C41 | −2.2 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5i | 0.87 (6) | 2.29 (6) | 3.123 (8) | 160 (11) |
O1W—H1W1···O4i | 0.87 (6) | 2.55 (12) | 3.136 (9) | 126 (9) |
O2W—H2W1···O7 | 0.87 (7) | 1.95 (9) | 2.732 (10) | 149 (9) |
O2W—H2W2···O8i | 0.90 (8) | 1.91 (8) | 2.678 (10) | 142 (7) |
O3W—H3W···O1Wii | 0.91 (12) | 1.92 (12) | 2.791 (10) | 160 (12) |
C23—H23···O3Wiii | 0.95 | 2.52 | 3.385 (19) | 152 |
C44—H44···O2Wiv | 0.95 | 2.47 | 3.406 (15) | 168 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/4; (ii) −y+1/2, x−1/2, z+1/4; (iii) y+1/2, −x+1/2, z−1/4; (iv) x−1, y, z. |
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