Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010172/bt6638sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010172/bt6638Isup2.hkl |
CCDC reference: 271816
Data collection: CrysAlis CCD (Kuma, 2000); cell refinement: CrysAlis RED (Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Version 1.062; Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C16H21O5PS | F(000) = 1504 |
Mr = 356.36 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.0994 (7) Å | Cell parameters from 7573 reflections |
b = 9.5999 (5) Å | θ = 2–25° |
c = 28.0432 (13) Å | µ = 0.28 mm−1 |
β = 102.249 (4)° | T = 291 K |
V = 3709.3 (3) Å3 | Prism, colourless |
Z = 8 | 0.59 × 0.46 × 0.17 mm |
Kuma KM4-CCD diffractometer | 6610 independent reflections |
Radiation source: fine-focus sealed tube | 5609 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 25.1°, θmin = 3.0° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | h = −16→16 |
Tmin = 0.837, Tmax = 0.948 | k = −11→11 |
51730 measured reflections | l = −33→33 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0597P)2 + 1.1587P] where P = (Fo2 + 2Fc2)/3 |
6610 reflections | (Δ/σ)max = 0.001 |
425 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Experimental. Because collected data were relatively weak, especially at the end of measurement, a part of reflections was marked as unobserved by data reduction software. This affect fraction of unique reflections observed (out to θ=25.1°) which is equal to 93.7%. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.04446 (5) | 0.22678 (8) | 0.16693 (3) | 0.0643 (2) | |
P1 | 0.08465 (5) | 0.27432 (7) | 0.10787 (2) | 0.04981 (19) | |
O1 | 0.27655 (12) | 0.78694 (17) | 0.16335 (6) | 0.0575 (5) | |
C1 | 0.32611 (19) | 0.8871 (3) | 0.19467 (11) | 0.0601 (7) | |
C2 | 0.38283 (17) | 0.8396 (3) | 0.24038 (10) | 0.0563 (7) | |
H2 | 0.4149 | 0.9056 | 0.2623 | 0.068* | |
C3 | 0.39202 (16) | 0.7047 (3) | 0.25321 (9) | 0.0499 (6) | |
C4 | 0.34141 (15) | 0.6014 (3) | 0.21948 (8) | 0.0457 (5) | |
C5 | 0.34487 (17) | 0.4572 (3) | 0.22777 (10) | 0.0564 (7) | |
H5 | 0.3818 | 0.4230 | 0.2569 | 0.068* | |
C6 | 0.29485 (18) | 0.3650 (3) | 0.19382 (10) | 0.0582 (7) | |
H6 | 0.2980 | 0.2696 | 0.1998 | 0.070* | |
C7 | 0.23990 (16) | 0.4167 (3) | 0.15069 (9) | 0.0495 (6) | |
C8 | 0.23343 (17) | 0.5575 (3) | 0.14085 (9) | 0.0485 (6) | |
H8 | 0.1957 | 0.5908 | 0.1118 | 0.058* | |
C9 | 0.28464 (16) | 0.6478 (2) | 0.17538 (9) | 0.0450 (5) | |
O2 | 0.31649 (17) | 1.0064 (2) | 0.18057 (9) | 0.0867 (7) | |
C10 | 0.4537 (2) | 0.6609 (4) | 0.30110 (10) | 0.0731 (8) | |
H10A | 0.5086 | 0.6092 | 0.2955 | 0.110* | |
H10B | 0.4162 | 0.6034 | 0.3182 | 0.110* | |
H10C | 0.4759 | 0.7419 | 0.3203 | 0.110* | |
O3 | 0.19455 (12) | 0.32366 (18) | 0.11427 (6) | 0.0567 (4) | |
O4 | 0.02874 (13) | 0.39701 (19) | 0.07725 (7) | 0.0605 (5) | |
C11 | −0.0757 (2) | 0.4218 (3) | 0.07270 (11) | 0.0651 (7) | |
H11 | −0.0900 | 0.4178 | 0.1054 | 0.078* | |
C12 | −0.0952 (3) | 0.5655 (4) | 0.05371 (16) | 0.1025 (12) | |
H12A | −0.0576 | 0.6303 | 0.0761 | 0.154* | |
H12B | −0.1630 | 0.5861 | 0.0502 | 0.154* | |
H12C | −0.0777 | 0.5731 | 0.0226 | 0.154* | |
C13 | −0.1336 (3) | 0.3115 (4) | 0.04221 (16) | 0.1099 (14) | |
H13A | −0.1200 | 0.3132 | 0.0101 | 0.165* | |
H13B | −0.2015 | 0.3284 | 0.0401 | 0.165* | |
H13C | −0.1165 | 0.2221 | 0.0568 | 0.165* | |
O5 | 0.08094 (13) | 0.15730 (18) | 0.06875 (6) | 0.0570 (4) | |
C14 | 0.1259 (2) | 0.0195 (3) | 0.08227 (10) | 0.0616 (7) | |
H14 | 0.1547 | 0.0180 | 0.1173 | 0.074* | |
C15 | 0.0466 (3) | −0.0873 (3) | 0.07089 (13) | 0.0882 (10) | |
H15A | −0.0027 | −0.0660 | 0.0887 | 0.132* | |
H15B | 0.0730 | −0.1779 | 0.0801 | 0.132* | |
H15C | 0.0188 | −0.0862 | 0.0365 | 0.132* | |
C16 | 0.2042 (3) | 0.0005 (4) | 0.05395 (15) | 0.0962 (11) | |
H16A | 0.1771 | 0.0122 | 0.0198 | 0.144* | |
H16B | 0.2311 | −0.0913 | 0.0596 | 0.144* | |
H16C | 0.2543 | 0.0684 | 0.0643 | 0.144* | |
S51 | 0.55323 (6) | 0.67599 (9) | 0.17290 (2) | 0.0666 (2) | |
P51 | 0.59592 (5) | 0.62719 (7) | 0.11472 (2) | 0.05259 (19) | |
O51 | 0.78158 (13) | 0.11218 (18) | 0.17091 (7) | 0.0597 (5) | |
C51 | 0.8304 (2) | 0.0100 (3) | 0.20191 (12) | 0.0652 (7) | |
C52 | 0.88873 (19) | 0.0572 (3) | 0.24728 (10) | 0.0622 (7) | |
H52 | 0.9214 | −0.0092 | 0.2688 | 0.075* | |
C53 | 0.89885 (17) | 0.1912 (3) | 0.26047 (9) | 0.0548 (6) | |
C54 | 0.84833 (16) | 0.2958 (3) | 0.22717 (9) | 0.0489 (6) | |
C55 | 0.85250 (18) | 0.4400 (3) | 0.23594 (10) | 0.0564 (6) | |
H55 | 0.8890 | 0.4732 | 0.2653 | 0.068* | |
C56 | 0.80378 (18) | 0.5335 (3) | 0.20212 (10) | 0.0582 (7) | |
H56 | 0.8077 | 0.6287 | 0.2084 | 0.070* | |
C57 | 0.74891 (17) | 0.4834 (3) | 0.15868 (9) | 0.0502 (6) | |
C58 | 0.74116 (17) | 0.3430 (3) | 0.14859 (9) | 0.0493 (6) | |
H58 | 0.7032 | 0.3107 | 0.1194 | 0.059* | |
C59 | 0.79119 (16) | 0.2513 (2) | 0.18289 (9) | 0.0474 (6) | |
O52 | 0.81883 (18) | −0.1079 (2) | 0.18748 (10) | 0.0932 (7) | |
C60 | 0.9605 (2) | 0.2335 (4) | 0.30858 (11) | 0.0777 (9) | |
H60A | 0.9808 | 0.1520 | 0.3279 | 0.117* | |
H60B | 0.9237 | 0.2929 | 0.3254 | 0.117* | |
H60C | 1.0166 | 0.2829 | 0.3032 | 0.117* | |
O53 | 0.70588 (12) | 0.57734 (18) | 0.12243 (6) | 0.0583 (5) | |
O55 | 0.59423 (15) | 0.74330 (19) | 0.07539 (6) | 0.0643 (5) | |
C64 | 0.6321 (3) | 0.8832 (3) | 0.08841 (12) | 0.0903 (11) | |
H64 | 0.6602 | 0.8871 | 0.1235 | 0.108* | |
C66 | 0.7086 (5) | 0.9087 (5) | 0.0608 (2) | 0.185 (3) | |
H66A | 0.7634 | 0.8499 | 0.0732 | 0.277* | |
H66B | 0.7283 | 1.0045 | 0.0643 | 0.277* | |
H66C | 0.6839 | 0.8882 | 0.0269 | 0.277* | |
C65 | 0.5460 (5) | 0.9805 (5) | 0.07643 (19) | 0.188 (3) | |
H65A | 0.5181 | 0.9759 | 0.0421 | 0.282* | |
H65B | 0.5669 | 1.0741 | 0.0850 | 0.282* | |
H65C | 0.4983 | 0.9533 | 0.0945 | 0.282* | |
O54 | 0.54122 (13) | 0.5040 (2) | 0.08387 (7) | 0.0649 (5) | |
C61 | 0.4360 (2) | 0.4804 (4) | 0.07809 (12) | 0.0765 (9) | |
H61 | 0.4184 | 0.4923 | 0.1098 | 0.092* | |
C63 | 0.3811 (3) | 0.5823 (6) | 0.04320 (17) | 0.1286 (16) | |
H63A | 0.3931 | 0.6747 | 0.0562 | 0.193* | |
H63B | 0.3129 | 0.5623 | 0.0381 | 0.193* | |
H63C | 0.4015 | 0.5761 | 0.0127 | 0.193* | |
C62 | 0.4189 (3) | 0.3328 (5) | 0.06230 (16) | 0.1169 (14) | |
H62A | 0.4388 | 0.3193 | 0.0319 | 0.175* | |
H62B | 0.3512 | 0.3115 | 0.0581 | 0.175* | |
H62C | 0.4559 | 0.2725 | 0.0866 | 0.175* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0700 (5) | 0.0716 (5) | 0.0558 (4) | −0.0089 (4) | 0.0237 (3) | −0.0011 (3) |
P1 | 0.0539 (4) | 0.0453 (4) | 0.0529 (4) | −0.0065 (3) | 0.0173 (3) | −0.0041 (3) |
O1 | 0.0577 (10) | 0.0419 (10) | 0.0674 (11) | −0.0026 (8) | 0.0007 (9) | 0.0040 (8) |
C1 | 0.0535 (15) | 0.0465 (16) | 0.0794 (19) | −0.0031 (12) | 0.0123 (14) | −0.0070 (14) |
C2 | 0.0465 (14) | 0.0581 (17) | 0.0641 (16) | −0.0069 (12) | 0.0114 (12) | −0.0146 (13) |
C3 | 0.0364 (12) | 0.0648 (17) | 0.0506 (13) | 0.0012 (11) | 0.0136 (10) | −0.0033 (12) |
C4 | 0.0347 (11) | 0.0517 (15) | 0.0522 (13) | 0.0034 (10) | 0.0128 (10) | 0.0022 (11) |
C5 | 0.0445 (13) | 0.0579 (17) | 0.0661 (16) | 0.0049 (12) | 0.0099 (12) | 0.0144 (13) |
C6 | 0.0513 (14) | 0.0472 (15) | 0.0768 (18) | 0.0030 (12) | 0.0152 (13) | 0.0086 (13) |
C7 | 0.0417 (12) | 0.0466 (14) | 0.0636 (15) | −0.0031 (11) | 0.0189 (11) | −0.0043 (12) |
C8 | 0.0446 (13) | 0.0486 (15) | 0.0521 (14) | 0.0023 (11) | 0.0099 (11) | 0.0014 (11) |
C9 | 0.0397 (12) | 0.0405 (13) | 0.0573 (14) | 0.0017 (10) | 0.0157 (11) | 0.0027 (11) |
O2 | 0.0936 (16) | 0.0468 (12) | 0.1083 (17) | −0.0081 (11) | −0.0042 (13) | 0.0034 (12) |
C10 | 0.0582 (16) | 0.095 (2) | 0.0617 (17) | 0.0030 (16) | 0.0025 (14) | −0.0029 (16) |
O3 | 0.0533 (10) | 0.0511 (10) | 0.0701 (11) | −0.0077 (8) | 0.0228 (8) | −0.0147 (9) |
O4 | 0.0604 (11) | 0.0556 (11) | 0.0694 (11) | −0.0009 (9) | 0.0227 (9) | 0.0047 (9) |
C11 | 0.0594 (16) | 0.0662 (18) | 0.0707 (18) | 0.0037 (14) | 0.0163 (14) | 0.0003 (15) |
C12 | 0.096 (3) | 0.080 (2) | 0.133 (3) | 0.025 (2) | 0.026 (2) | 0.015 (2) |
C13 | 0.079 (2) | 0.104 (3) | 0.131 (3) | −0.003 (2) | −0.010 (2) | −0.023 (3) |
O5 | 0.0733 (12) | 0.0484 (10) | 0.0491 (9) | −0.0050 (9) | 0.0124 (8) | −0.0038 (8) |
C14 | 0.0780 (18) | 0.0474 (15) | 0.0577 (15) | 0.0010 (14) | 0.0102 (14) | −0.0059 (12) |
C15 | 0.117 (3) | 0.0582 (19) | 0.085 (2) | −0.0221 (19) | 0.012 (2) | 0.0015 (17) |
C16 | 0.103 (3) | 0.083 (2) | 0.112 (3) | 0.008 (2) | 0.043 (2) | −0.016 (2) |
S51 | 0.0721 (5) | 0.0778 (5) | 0.0542 (4) | 0.0103 (4) | 0.0233 (3) | −0.0032 (3) |
P51 | 0.0569 (4) | 0.0520 (4) | 0.0513 (4) | 0.0081 (3) | 0.0169 (3) | −0.0003 (3) |
O51 | 0.0602 (11) | 0.0444 (10) | 0.0719 (12) | 0.0004 (8) | 0.0082 (9) | −0.0078 (9) |
C51 | 0.0600 (16) | 0.0483 (17) | 0.090 (2) | 0.0044 (13) | 0.0220 (15) | 0.0063 (15) |
C52 | 0.0506 (15) | 0.0658 (19) | 0.0718 (18) | 0.0059 (13) | 0.0170 (13) | 0.0163 (15) |
C53 | 0.0382 (12) | 0.0708 (19) | 0.0583 (15) | −0.0015 (12) | 0.0171 (11) | 0.0047 (14) |
C54 | 0.0345 (12) | 0.0575 (16) | 0.0572 (14) | −0.0032 (11) | 0.0154 (11) | −0.0058 (12) |
C55 | 0.0473 (14) | 0.0582 (17) | 0.0636 (16) | −0.0064 (12) | 0.0114 (12) | −0.0114 (13) |
C56 | 0.0523 (14) | 0.0434 (14) | 0.0805 (19) | −0.0061 (12) | 0.0176 (13) | −0.0100 (13) |
C57 | 0.0431 (13) | 0.0478 (15) | 0.0632 (15) | 0.0005 (11) | 0.0193 (12) | 0.0043 (12) |
C58 | 0.0450 (13) | 0.0509 (15) | 0.0525 (14) | −0.0008 (11) | 0.0112 (11) | −0.0056 (12) |
C59 | 0.0428 (13) | 0.0419 (14) | 0.0602 (15) | −0.0030 (10) | 0.0172 (11) | −0.0054 (11) |
O52 | 0.1023 (17) | 0.0453 (13) | 0.126 (2) | 0.0052 (12) | 0.0098 (14) | −0.0049 (12) |
C60 | 0.0615 (18) | 0.102 (2) | 0.0664 (18) | −0.0025 (17) | 0.0072 (15) | 0.0053 (17) |
O53 | 0.0557 (10) | 0.0541 (11) | 0.0707 (11) | 0.0051 (8) | 0.0255 (9) | 0.0106 (9) |
O55 | 0.0888 (13) | 0.0562 (11) | 0.0479 (10) | 0.0086 (10) | 0.0141 (9) | 0.0009 (8) |
C64 | 0.154 (3) | 0.0540 (19) | 0.0606 (18) | 0.004 (2) | 0.017 (2) | 0.0028 (15) |
C66 | 0.315 (8) | 0.126 (4) | 0.155 (4) | −0.117 (5) | 0.144 (5) | −0.036 (4) |
C65 | 0.314 (8) | 0.100 (4) | 0.120 (4) | 0.102 (5) | −0.024 (5) | 0.000 (3) |
O54 | 0.0598 (11) | 0.0683 (12) | 0.0701 (12) | −0.0009 (9) | 0.0214 (9) | −0.0151 (10) |
C61 | 0.0593 (17) | 0.100 (3) | 0.0712 (19) | −0.0097 (17) | 0.0171 (15) | −0.0141 (18) |
C63 | 0.081 (3) | 0.166 (4) | 0.128 (4) | 0.016 (3) | −0.003 (2) | 0.029 (3) |
C62 | 0.105 (3) | 0.117 (3) | 0.128 (3) | −0.041 (3) | 0.023 (3) | −0.035 (3) |
S1—P1 | 1.9159 (9) | S51—P51 | 1.9131 (9) |
P1—O5 | 1.5634 (18) | P51—O55 | 1.5647 (19) |
P1—O4 | 1.5682 (19) | P51—O54 | 1.5681 (19) |
P1—O3 | 1.5937 (17) | P51—O53 | 1.5928 (18) |
O1—C9 | 1.377 (3) | O51—C59 | 1.376 (3) |
O1—C1 | 1.387 (3) | O51—C51 | 1.392 (3) |
C1—O2 | 1.210 (3) | C51—O52 | 1.202 (3) |
C1—C2 | 1.434 (4) | C51—C52 | 1.434 (4) |
C2—C3 | 1.343 (4) | C52—C53 | 1.338 (4) |
C2—H2 | 0.9300 | C52—H52 | 0.9300 |
C3—C4 | 1.450 (3) | C53—C54 | 1.452 (4) |
C3—C10 | 1.497 (4) | C53—C60 | 1.498 (4) |
C4—C9 | 1.396 (3) | C54—C59 | 1.396 (3) |
C4—C5 | 1.402 (3) | C54—C55 | 1.405 (3) |
C5—C6 | 1.380 (4) | C55—C56 | 1.379 (4) |
C5—H5 | 0.9300 | C55—H55 | 0.9300 |
C6—C7 | 1.383 (4) | C56—C57 | 1.383 (4) |
C6—H6 | 0.9300 | C56—H56 | 0.9300 |
C7—C8 | 1.379 (3) | C57—C58 | 1.377 (3) |
C7—O3 | 1.404 (3) | C57—O53 | 1.398 (3) |
C8—C9 | 1.383 (3) | C58—C59 | 1.382 (3) |
C8—H8 | 0.9300 | C58—H58 | 0.9300 |
C10—H10A | 0.9600 | C60—H60A | 0.9600 |
C10—H10B | 0.9600 | C60—H60B | 0.9600 |
C10—H10C | 0.9600 | C60—H60C | 0.9600 |
O4—C11 | 1.470 (3) | O55—C64 | 1.462 (4) |
C11—C12 | 1.484 (4) | C64—C66 | 1.477 (6) |
C11—C13 | 1.490 (4) | C64—C65 | 1.512 (6) |
C11—H11 | 0.9800 | C64—H64 | 0.9800 |
C12—H12A | 0.9600 | C66—H66A | 0.9600 |
C12—H12B | 0.9600 | C66—H66B | 0.9600 |
C12—H12C | 0.9600 | C66—H66C | 0.9600 |
C13—H13A | 0.9600 | C65—H65A | 0.9600 |
C13—H13B | 0.9600 | C65—H65B | 0.9600 |
C13—H13C | 0.9600 | C65—H65C | 0.9600 |
O5—C14 | 1.481 (3) | O54—C61 | 1.475 (3) |
C14—C15 | 1.500 (4) | C61—C63 | 1.481 (5) |
C14—C16 | 1.501 (4) | C61—C62 | 1.489 (5) |
C14—H14 | 0.9800 | C61—H61 | 0.9800 |
C15—H15A | 0.9600 | C63—H63A | 0.9600 |
C15—H15B | 0.9600 | C63—H63B | 0.9600 |
C15—H15C | 0.9600 | C63—H63C | 0.9600 |
C16—H16A | 0.9600 | C62—H62A | 0.9600 |
C16—H16B | 0.9600 | C62—H62B | 0.9600 |
C16—H16C | 0.9600 | C62—H62C | 0.9600 |
O5—P1—O4 | 102.55 (10) | O55—P51—O54 | 102.48 (10) |
O5—P1—O3 | 100.34 (10) | O55—P51—O53 | 100.29 (10) |
O4—P1—O3 | 101.67 (10) | O54—P51—O53 | 101.48 (10) |
O5—P1—S1 | 117.62 (8) | O55—P51—S51 | 117.78 (8) |
O4—P1—S1 | 116.48 (8) | O54—P51—S51 | 116.63 (8) |
O3—P1—S1 | 115.61 (8) | O53—P51—S51 | 115.54 (8) |
C9—O1—C1 | 120.9 (2) | C59—O51—C51 | 121.4 (2) |
O2—C1—O1 | 116.3 (3) | O52—C51—O51 | 116.1 (3) |
O2—C1—C2 | 126.6 (3) | O52—C51—C52 | 127.5 (3) |
O1—C1—C2 | 117.1 (2) | O51—C51—C52 | 116.5 (2) |
C3—C2—C1 | 123.4 (2) | C53—C52—C51 | 123.8 (3) |
C3—C2—H2 | 118.3 | C53—C52—H52 | 118.1 |
C1—C2—H2 | 118.3 | C51—C52—H52 | 118.1 |
C2—C3—C4 | 118.6 (2) | C52—C53—C54 | 118.6 (2) |
C2—C3—C10 | 121.1 (2) | C52—C53—C60 | 121.2 (3) |
C4—C3—C10 | 120.3 (2) | C54—C53—C60 | 120.2 (3) |
C9—C4—C5 | 117.1 (2) | C59—C54—C55 | 116.9 (2) |
C9—C4—C3 | 118.0 (2) | C59—C54—C53 | 118.2 (2) |
C5—C4—C3 | 124.9 (2) | C55—C54—C53 | 124.9 (2) |
C6—C5—C4 | 121.6 (2) | C56—C55—C54 | 121.7 (2) |
C6—C5—H5 | 119.2 | C56—C55—H55 | 119.2 |
C4—C5—H5 | 119.2 | C54—C55—H55 | 119.2 |
C5—C6—C7 | 118.9 (2) | C55—C56—C57 | 118.9 (2) |
C5—C6—H6 | 120.6 | C55—C56—H56 | 120.5 |
C7—C6—H6 | 120.6 | C57—C56—H56 | 120.5 |
C8—C7—C6 | 121.9 (2) | C58—C57—C56 | 121.8 (2) |
C8—C7—O3 | 118.5 (2) | C58—C57—O53 | 118.6 (2) |
C6—C7—O3 | 119.5 (2) | C56—C57—O53 | 119.5 (2) |
C7—C8—C9 | 118.1 (2) | C57—C58—C59 | 118.3 (2) |
C7—C8—H8 | 120.9 | C57—C58—H58 | 120.8 |
C9—C8—H8 | 120.9 | C59—C58—H58 | 120.8 |
O1—C9—C8 | 115.6 (2) | O51—C59—C58 | 116.0 (2) |
O1—C9—C4 | 121.9 (2) | O51—C59—C54 | 121.5 (2) |
C8—C9—C4 | 122.4 (2) | C58—C59—C54 | 122.4 (2) |
C3—C10—H10A | 109.5 | C53—C60—H60A | 109.5 |
C3—C10—H10B | 109.5 | C53—C60—H60B | 109.5 |
H10A—C10—H10B | 109.5 | H60A—C60—H60B | 109.5 |
C3—C10—H10C | 109.5 | C53—C60—H60C | 109.5 |
H10A—C10—H10C | 109.5 | H60A—C60—H60C | 109.5 |
H10B—C10—H10C | 109.5 | H60B—C60—H60C | 109.5 |
C7—O3—P1 | 123.55 (14) | C57—O53—P51 | 123.53 (15) |
C11—O4—P1 | 123.14 (16) | C64—O55—P51 | 121.87 (17) |
O4—C11—C12 | 106.7 (2) | O55—C64—C66 | 106.8 (3) |
O4—C11—C13 | 110.6 (3) | O55—C64—C65 | 106.2 (4) |
C12—C11—C13 | 114.7 (3) | C66—C64—C65 | 115.0 (4) |
O4—C11—H11 | 108.2 | O55—C64—H64 | 109.5 |
C12—C11—H11 | 108.2 | C66—C64—H64 | 109.5 |
C13—C11—H11 | 108.2 | C65—C64—H64 | 109.5 |
C11—C12—H12A | 109.5 | C64—C66—H66A | 109.5 |
C11—C12—H12B | 109.5 | C64—C66—H66B | 109.5 |
H12A—C12—H12B | 109.5 | H66A—C66—H66B | 109.5 |
C11—C12—H12C | 109.5 | C64—C66—H66C | 109.5 |
H12A—C12—H12C | 109.5 | H66A—C66—H66C | 109.5 |
H12B—C12—H12C | 109.5 | H66B—C66—H66C | 109.5 |
C11—C13—H13A | 109.5 | C64—C65—H65A | 109.5 |
C11—C13—H13B | 109.5 | C64—C65—H65B | 109.5 |
H13A—C13—H13B | 109.5 | H65A—C65—H65B | 109.5 |
C11—C13—H13C | 109.5 | C64—C65—H65C | 109.5 |
H13A—C13—H13C | 109.5 | H65A—C65—H65C | 109.5 |
H13B—C13—H13C | 109.5 | H65B—C65—H65C | 109.5 |
C14—O5—P1 | 120.88 (15) | C61—O54—P51 | 122.81 (18) |
O5—C14—C15 | 107.3 (2) | O54—C61—C63 | 110.1 (3) |
O5—C14—C16 | 107.2 (2) | O54—C61—C62 | 105.9 (3) |
C15—C14—C16 | 113.7 (3) | C63—C61—C62 | 113.8 (3) |
O5—C14—H14 | 109.5 | O54—C61—H61 | 109.0 |
C15—C14—H14 | 109.5 | C63—C61—H61 | 109.0 |
C16—C14—H14 | 109.5 | C62—C61—H61 | 109.0 |
C14—C15—H15A | 109.5 | C61—C63—H63A | 109.5 |
C14—C15—H15B | 109.5 | C61—C63—H63B | 109.5 |
H15A—C15—H15B | 109.5 | H63A—C63—H63B | 109.5 |
C14—C15—H15C | 109.5 | C61—C63—H63C | 109.5 |
H15A—C15—H15C | 109.5 | H63A—C63—H63C | 109.5 |
H15B—C15—H15C | 109.5 | H63B—C63—H63C | 109.5 |
C14—C16—H16A | 109.5 | C61—C62—H62A | 109.5 |
C14—C16—H16B | 109.5 | C61—C62—H62B | 109.5 |
H16A—C16—H16B | 109.5 | H62A—C62—H62B | 109.5 |
C14—C16—H16C | 109.5 | C61—C62—H62C | 109.5 |
H16A—C16—H16C | 109.5 | H62A—C62—H62C | 109.5 |
H16B—C16—H16C | 109.5 | H62B—C62—H62C | 109.5 |
C7—O3—P1—S1 | −43.7 (2) | C57—O53—P51—S51 | 44.8 (2) |
C7—O3—P1—O4 | 83.5 (2) | C57—O53—P51—O54 | −82.4 (2) |
O3—P1—O4—C11 | −162.78 (19) | O53—P51—O54—C51 | 37.56 (8) |
P1—O4—C11—C12 | 164.1 (2) | P51—O54—C51—C52 | 15.52 (19) |
P1—O4—C11—C13 | −70.6 (3) | P51—O54—C51—C53 | 9.96 (11) |
C7—O3—P1—O5 | −171.25 (18) | C57—O53—P51—O55 | 172.49 (18) |
O3—P1—O5—C14 | 75.69 (19) | O53—P51—O55—C54 | −6.69 (10) |
P1—O5—C14—C15 | 119.2 (2) | P51—O55—C54—C55 | −106.9 (2) |
P1—O5—C14—C16 | −118.2 (2) | P51—O55—C54—C56 | −111.45 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O2i | 0.98 | 2.58 | 3.420 (4) | 144 |
C60—H60C···O52ii | 0.96 | 2.51 | 3.444 (4) | 165 |
C64—H64···O52iii | 0.98 | 2.55 | 3.399 (4) | 145 |
Symmetry codes: (i) x, y−1, z; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y+1, z. |