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The asymmetric unit of the title compound, C16H21O5PS, contains two symmetry-independent mol­ecules. The overall molecular geometry of both mol­ecules is very similar. The coumarin ring systems are only insignificantly distorted from planarity. In the structure, C—H...O and C—H...π weak intermolecular hydrogen bonds can be found. In addition, stacking interactions between the rings are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010172/bt6638sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010172/bt6638Isup2.hkl
Contains datablock I

CCDC reference: 271816

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.140
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Author Response: 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 affects fraction of unique reflections observed (out to \q=25.1\%) which is equal to 93.7%.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C64
Author Response: The isoprophyl substituent indicated by C64 atom shows signs of dynamic disorder, especially for atoms C65 and C66. This affects the anisotropic displacement parameters and in consequence equivalent isotropic displacement parameters. As a result, there is a difference between equivalent isotropic displacement parameter of C64 atom and C65 and C66 atoms.

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.97 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.78 Ratio
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
Author Response: The isoprophyl substituent indicated by C64 atom shows signs of dynamic disorder, especially for atoms C65 and C66. This affects the anisotropic displacement parameters and in consequence equivalent isotropic displacement parameters. As a result, there is a difference between equivalent isotropic displacement parameter of C64 atom and C65 and C66 atoms.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
Author Response: The isoprophyl substituent indicated by C64 atom shows signs of dynamic disorder, especially for atoms C65 and C66. This affects the anisotropic displacement parameters and in consequence equivalent isotropic displacement parameters. As a result, there is a difference between equivalent isotropic displacement parameter of C64 atom and C65 and C66 atoms.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C61
Author Response: The isoprophyl substituent indicated by C64 atom shows signs of dynamic disorder, especially for atoms C65 and C66. This affects the anisotropic displacement parameters and in consequence equivalent isotropic displacement parameters. As a result, there is a difference between equivalent isotropic displacement parameter of C64 atom and C65 and C66 atoms.

2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

O,O'-Diisopropyl (4-methyl-7-cumarinyloxy)phosphonothioate top
Crystal data top
C16H21O5PSF(000) = 1504
Mr = 356.36Dx = 1.276 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.0994 (7) ÅCell parameters from 7573 reflections
b = 9.5999 (5) Åθ = 2–25°
c = 28.0432 (13) ŵ = 0.28 mm1
β = 102.249 (4)°T = 291 K
V = 3709.3 (3) Å3Prism, colourless
Z = 80.59 × 0.46 × 0.17 mm
Data collection top
Kuma KM4-CCD
diffractometer
6610 independent reflections
Radiation source: fine-focus sealed tube5609 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 25.1°, θmin = 3.0°
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
h = 1616
Tmin = 0.837, Tmax = 0.948k = 1111
51730 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.04446 (5)0.22678 (8)0.16693 (3)0.0643 (2)
P10.08465 (5)0.27432 (7)0.10787 (2)0.04981 (19)
O10.27655 (12)0.78694 (17)0.16335 (6)0.0575 (5)
C10.32611 (19)0.8871 (3)0.19467 (11)0.0601 (7)
C20.38283 (17)0.8396 (3)0.24038 (10)0.0563 (7)
H20.41490.90560.26230.068*
C30.39202 (16)0.7047 (3)0.25321 (9)0.0499 (6)
C40.34141 (15)0.6014 (3)0.21948 (8)0.0457 (5)
C50.34487 (17)0.4572 (3)0.22777 (10)0.0564 (7)
H50.38180.42300.25690.068*
C60.29485 (18)0.3650 (3)0.19382 (10)0.0582 (7)
H60.29800.26960.19980.070*
C70.23990 (16)0.4167 (3)0.15069 (9)0.0495 (6)
C80.23343 (17)0.5575 (3)0.14085 (9)0.0485 (6)
H80.19570.59080.11180.058*
C90.28464 (16)0.6478 (2)0.17538 (9)0.0450 (5)
O20.31649 (17)1.0064 (2)0.18057 (9)0.0867 (7)
C100.4537 (2)0.6609 (4)0.30110 (10)0.0731 (8)
H10A0.50860.60920.29550.110*
H10B0.41620.60340.31820.110*
H10C0.47590.74190.32030.110*
O30.19455 (12)0.32366 (18)0.11427 (6)0.0567 (4)
O40.02874 (13)0.39701 (19)0.07725 (7)0.0605 (5)
C110.0757 (2)0.4218 (3)0.07270 (11)0.0651 (7)
H110.09000.41780.10540.078*
C120.0952 (3)0.5655 (4)0.05371 (16)0.1025 (12)
H12A0.05760.63030.07610.154*
H12B0.16300.58610.05020.154*
H12C0.07770.57310.02260.154*
C130.1336 (3)0.3115 (4)0.04221 (16)0.1099 (14)
H13A0.12000.31320.01010.165*
H13B0.20150.32840.04010.165*
H13C0.11650.22210.05680.165*
O50.08094 (13)0.15730 (18)0.06875 (6)0.0570 (4)
C140.1259 (2)0.0195 (3)0.08227 (10)0.0616 (7)
H140.15470.01800.11730.074*
C150.0466 (3)0.0873 (3)0.07089 (13)0.0882 (10)
H15A0.00270.06600.08870.132*
H15B0.07300.17790.08010.132*
H15C0.01880.08620.03650.132*
C160.2042 (3)0.0005 (4)0.05395 (15)0.0962 (11)
H16A0.17710.01220.01980.144*
H16B0.23110.09130.05960.144*
H16C0.25430.06840.06430.144*
S510.55323 (6)0.67599 (9)0.17290 (2)0.0666 (2)
P510.59592 (5)0.62719 (7)0.11472 (2)0.05259 (19)
O510.78158 (13)0.11218 (18)0.17091 (7)0.0597 (5)
C510.8304 (2)0.0100 (3)0.20191 (12)0.0652 (7)
C520.88873 (19)0.0572 (3)0.24728 (10)0.0622 (7)
H520.92140.00920.26880.075*
C530.89885 (17)0.1912 (3)0.26047 (9)0.0548 (6)
C540.84833 (16)0.2958 (3)0.22717 (9)0.0489 (6)
C550.85250 (18)0.4400 (3)0.23594 (10)0.0564 (6)
H550.88900.47320.26530.068*
C560.80378 (18)0.5335 (3)0.20212 (10)0.0582 (7)
H560.80770.62870.20840.070*
C570.74891 (17)0.4834 (3)0.15868 (9)0.0502 (6)
C580.74116 (17)0.3430 (3)0.14859 (9)0.0493 (6)
H580.70320.31070.11940.059*
C590.79119 (16)0.2513 (2)0.18289 (9)0.0474 (6)
O520.81883 (18)0.1079 (2)0.18748 (10)0.0932 (7)
C600.9605 (2)0.2335 (4)0.30858 (11)0.0777 (9)
H60A0.98080.15200.32790.117*
H60B0.92370.29290.32540.117*
H60C1.01660.28290.30320.117*
O530.70588 (12)0.57734 (18)0.12243 (6)0.0583 (5)
O550.59423 (15)0.74330 (19)0.07539 (6)0.0643 (5)
C640.6321 (3)0.8832 (3)0.08841 (12)0.0903 (11)
H640.66020.88710.12350.108*
C660.7086 (5)0.9087 (5)0.0608 (2)0.185 (3)
H66A0.76340.84990.07320.277*
H66B0.72831.00450.06430.277*
H66C0.68390.88820.02690.277*
C650.5460 (5)0.9805 (5)0.07643 (19)0.188 (3)
H65A0.51810.97590.04210.282*
H65B0.56691.07410.08500.282*
H65C0.49830.95330.09450.282*
O540.54122 (13)0.5040 (2)0.08387 (7)0.0649 (5)
C610.4360 (2)0.4804 (4)0.07809 (12)0.0765 (9)
H610.41840.49230.10980.092*
C630.3811 (3)0.5823 (6)0.04320 (17)0.1286 (16)
H63A0.39310.67470.05620.193*
H63B0.31290.56230.03810.193*
H63C0.40150.57610.01270.193*
C620.4189 (3)0.3328 (5)0.06230 (16)0.1169 (14)
H62A0.43880.31930.03190.175*
H62B0.35120.31150.05810.175*
H62C0.45590.27250.08660.175*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0700 (5)0.0716 (5)0.0558 (4)0.0089 (4)0.0237 (3)0.0011 (3)
P10.0539 (4)0.0453 (4)0.0529 (4)0.0065 (3)0.0173 (3)0.0041 (3)
O10.0577 (10)0.0419 (10)0.0674 (11)0.0026 (8)0.0007 (9)0.0040 (8)
C10.0535 (15)0.0465 (16)0.0794 (19)0.0031 (12)0.0123 (14)0.0070 (14)
C20.0465 (14)0.0581 (17)0.0641 (16)0.0069 (12)0.0114 (12)0.0146 (13)
C30.0364 (12)0.0648 (17)0.0506 (13)0.0012 (11)0.0136 (10)0.0033 (12)
C40.0347 (11)0.0517 (15)0.0522 (13)0.0034 (10)0.0128 (10)0.0022 (11)
C50.0445 (13)0.0579 (17)0.0661 (16)0.0049 (12)0.0099 (12)0.0144 (13)
C60.0513 (14)0.0472 (15)0.0768 (18)0.0030 (12)0.0152 (13)0.0086 (13)
C70.0417 (12)0.0466 (14)0.0636 (15)0.0031 (11)0.0189 (11)0.0043 (12)
C80.0446 (13)0.0486 (15)0.0521 (14)0.0023 (11)0.0099 (11)0.0014 (11)
C90.0397 (12)0.0405 (13)0.0573 (14)0.0017 (10)0.0157 (11)0.0027 (11)
O20.0936 (16)0.0468 (12)0.1083 (17)0.0081 (11)0.0042 (13)0.0034 (12)
C100.0582 (16)0.095 (2)0.0617 (17)0.0030 (16)0.0025 (14)0.0029 (16)
O30.0533 (10)0.0511 (10)0.0701 (11)0.0077 (8)0.0228 (8)0.0147 (9)
O40.0604 (11)0.0556 (11)0.0694 (11)0.0009 (9)0.0227 (9)0.0047 (9)
C110.0594 (16)0.0662 (18)0.0707 (18)0.0037 (14)0.0163 (14)0.0003 (15)
C120.096 (3)0.080 (2)0.133 (3)0.025 (2)0.026 (2)0.015 (2)
C130.079 (2)0.104 (3)0.131 (3)0.003 (2)0.010 (2)0.023 (3)
O50.0733 (12)0.0484 (10)0.0491 (9)0.0050 (9)0.0124 (8)0.0038 (8)
C140.0780 (18)0.0474 (15)0.0577 (15)0.0010 (14)0.0102 (14)0.0059 (12)
C150.117 (3)0.0582 (19)0.085 (2)0.0221 (19)0.012 (2)0.0015 (17)
C160.103 (3)0.083 (2)0.112 (3)0.008 (2)0.043 (2)0.016 (2)
S510.0721 (5)0.0778 (5)0.0542 (4)0.0103 (4)0.0233 (3)0.0032 (3)
P510.0569 (4)0.0520 (4)0.0513 (4)0.0081 (3)0.0169 (3)0.0003 (3)
O510.0602 (11)0.0444 (10)0.0719 (12)0.0004 (8)0.0082 (9)0.0078 (9)
C510.0600 (16)0.0483 (17)0.090 (2)0.0044 (13)0.0220 (15)0.0063 (15)
C520.0506 (15)0.0658 (19)0.0718 (18)0.0059 (13)0.0170 (13)0.0163 (15)
C530.0382 (12)0.0708 (19)0.0583 (15)0.0015 (12)0.0171 (11)0.0047 (14)
C540.0345 (12)0.0575 (16)0.0572 (14)0.0032 (11)0.0154 (11)0.0058 (12)
C550.0473 (14)0.0582 (17)0.0636 (16)0.0064 (12)0.0114 (12)0.0114 (13)
C560.0523 (14)0.0434 (14)0.0805 (19)0.0061 (12)0.0176 (13)0.0100 (13)
C570.0431 (13)0.0478 (15)0.0632 (15)0.0005 (11)0.0193 (12)0.0043 (12)
C580.0450 (13)0.0509 (15)0.0525 (14)0.0008 (11)0.0112 (11)0.0056 (12)
C590.0428 (13)0.0419 (14)0.0602 (15)0.0030 (10)0.0172 (11)0.0054 (11)
O520.1023 (17)0.0453 (13)0.126 (2)0.0052 (12)0.0098 (14)0.0049 (12)
C600.0615 (18)0.102 (2)0.0664 (18)0.0025 (17)0.0072 (15)0.0053 (17)
O530.0557 (10)0.0541 (11)0.0707 (11)0.0051 (8)0.0255 (9)0.0106 (9)
O550.0888 (13)0.0562 (11)0.0479 (10)0.0086 (10)0.0141 (9)0.0009 (8)
C640.154 (3)0.0540 (19)0.0606 (18)0.004 (2)0.017 (2)0.0028 (15)
C660.315 (8)0.126 (4)0.155 (4)0.117 (5)0.144 (5)0.036 (4)
C650.314 (8)0.100 (4)0.120 (4)0.102 (5)0.024 (5)0.000 (3)
O540.0598 (11)0.0683 (12)0.0701 (12)0.0009 (9)0.0214 (9)0.0151 (10)
C610.0593 (17)0.100 (3)0.0712 (19)0.0097 (17)0.0171 (15)0.0141 (18)
C630.081 (3)0.166 (4)0.128 (4)0.016 (3)0.003 (2)0.029 (3)
C620.105 (3)0.117 (3)0.128 (3)0.041 (3)0.023 (3)0.035 (3)
Geometric parameters (Å, º) top
S1—P11.9159 (9)S51—P511.9131 (9)
P1—O51.5634 (18)P51—O551.5647 (19)
P1—O41.5682 (19)P51—O541.5681 (19)
P1—O31.5937 (17)P51—O531.5928 (18)
O1—C91.377 (3)O51—C591.376 (3)
O1—C11.387 (3)O51—C511.392 (3)
C1—O21.210 (3)C51—O521.202 (3)
C1—C21.434 (4)C51—C521.434 (4)
C2—C31.343 (4)C52—C531.338 (4)
C2—H20.9300C52—H520.9300
C3—C41.450 (3)C53—C541.452 (4)
C3—C101.497 (4)C53—C601.498 (4)
C4—C91.396 (3)C54—C591.396 (3)
C4—C51.402 (3)C54—C551.405 (3)
C5—C61.380 (4)C55—C561.379 (4)
C5—H50.9300C55—H550.9300
C6—C71.383 (4)C56—C571.383 (4)
C6—H60.9300C56—H560.9300
C7—C81.379 (3)C57—C581.377 (3)
C7—O31.404 (3)C57—O531.398 (3)
C8—C91.383 (3)C58—C591.382 (3)
C8—H80.9300C58—H580.9300
C10—H10A0.9600C60—H60A0.9600
C10—H10B0.9600C60—H60B0.9600
C10—H10C0.9600C60—H60C0.9600
O4—C111.470 (3)O55—C641.462 (4)
C11—C121.484 (4)C64—C661.477 (6)
C11—C131.490 (4)C64—C651.512 (6)
C11—H110.9800C64—H640.9800
C12—H12A0.9600C66—H66A0.9600
C12—H12B0.9600C66—H66B0.9600
C12—H12C0.9600C66—H66C0.9600
C13—H13A0.9600C65—H65A0.9600
C13—H13B0.9600C65—H65B0.9600
C13—H13C0.9600C65—H65C0.9600
O5—C141.481 (3)O54—C611.475 (3)
C14—C151.500 (4)C61—C631.481 (5)
C14—C161.501 (4)C61—C621.489 (5)
C14—H140.9800C61—H610.9800
C15—H15A0.9600C63—H63A0.9600
C15—H15B0.9600C63—H63B0.9600
C15—H15C0.9600C63—H63C0.9600
C16—H16A0.9600C62—H62A0.9600
C16—H16B0.9600C62—H62B0.9600
C16—H16C0.9600C62—H62C0.9600
O5—P1—O4102.55 (10)O55—P51—O54102.48 (10)
O5—P1—O3100.34 (10)O55—P51—O53100.29 (10)
O4—P1—O3101.67 (10)O54—P51—O53101.48 (10)
O5—P1—S1117.62 (8)O55—P51—S51117.78 (8)
O4—P1—S1116.48 (8)O54—P51—S51116.63 (8)
O3—P1—S1115.61 (8)O53—P51—S51115.54 (8)
C9—O1—C1120.9 (2)C59—O51—C51121.4 (2)
O2—C1—O1116.3 (3)O52—C51—O51116.1 (3)
O2—C1—C2126.6 (3)O52—C51—C52127.5 (3)
O1—C1—C2117.1 (2)O51—C51—C52116.5 (2)
C3—C2—C1123.4 (2)C53—C52—C51123.8 (3)
C3—C2—H2118.3C53—C52—H52118.1
C1—C2—H2118.3C51—C52—H52118.1
C2—C3—C4118.6 (2)C52—C53—C54118.6 (2)
C2—C3—C10121.1 (2)C52—C53—C60121.2 (3)
C4—C3—C10120.3 (2)C54—C53—C60120.2 (3)
C9—C4—C5117.1 (2)C59—C54—C55116.9 (2)
C9—C4—C3118.0 (2)C59—C54—C53118.2 (2)
C5—C4—C3124.9 (2)C55—C54—C53124.9 (2)
C6—C5—C4121.6 (2)C56—C55—C54121.7 (2)
C6—C5—H5119.2C56—C55—H55119.2
C4—C5—H5119.2C54—C55—H55119.2
C5—C6—C7118.9 (2)C55—C56—C57118.9 (2)
C5—C6—H6120.6C55—C56—H56120.5
C7—C6—H6120.6C57—C56—H56120.5
C8—C7—C6121.9 (2)C58—C57—C56121.8 (2)
C8—C7—O3118.5 (2)C58—C57—O53118.6 (2)
C6—C7—O3119.5 (2)C56—C57—O53119.5 (2)
C7—C8—C9118.1 (2)C57—C58—C59118.3 (2)
C7—C8—H8120.9C57—C58—H58120.8
C9—C8—H8120.9C59—C58—H58120.8
O1—C9—C8115.6 (2)O51—C59—C58116.0 (2)
O1—C9—C4121.9 (2)O51—C59—C54121.5 (2)
C8—C9—C4122.4 (2)C58—C59—C54122.4 (2)
C3—C10—H10A109.5C53—C60—H60A109.5
C3—C10—H10B109.5C53—C60—H60B109.5
H10A—C10—H10B109.5H60A—C60—H60B109.5
C3—C10—H10C109.5C53—C60—H60C109.5
H10A—C10—H10C109.5H60A—C60—H60C109.5
H10B—C10—H10C109.5H60B—C60—H60C109.5
C7—O3—P1123.55 (14)C57—O53—P51123.53 (15)
C11—O4—P1123.14 (16)C64—O55—P51121.87 (17)
O4—C11—C12106.7 (2)O55—C64—C66106.8 (3)
O4—C11—C13110.6 (3)O55—C64—C65106.2 (4)
C12—C11—C13114.7 (3)C66—C64—C65115.0 (4)
O4—C11—H11108.2O55—C64—H64109.5
C12—C11—H11108.2C66—C64—H64109.5
C13—C11—H11108.2C65—C64—H64109.5
C11—C12—H12A109.5C64—C66—H66A109.5
C11—C12—H12B109.5C64—C66—H66B109.5
H12A—C12—H12B109.5H66A—C66—H66B109.5
C11—C12—H12C109.5C64—C66—H66C109.5
H12A—C12—H12C109.5H66A—C66—H66C109.5
H12B—C12—H12C109.5H66B—C66—H66C109.5
C11—C13—H13A109.5C64—C65—H65A109.5
C11—C13—H13B109.5C64—C65—H65B109.5
H13A—C13—H13B109.5H65A—C65—H65B109.5
C11—C13—H13C109.5C64—C65—H65C109.5
H13A—C13—H13C109.5H65A—C65—H65C109.5
H13B—C13—H13C109.5H65B—C65—H65C109.5
C14—O5—P1120.88 (15)C61—O54—P51122.81 (18)
O5—C14—C15107.3 (2)O54—C61—C63110.1 (3)
O5—C14—C16107.2 (2)O54—C61—C62105.9 (3)
C15—C14—C16113.7 (3)C63—C61—C62113.8 (3)
O5—C14—H14109.5O54—C61—H61109.0
C15—C14—H14109.5C63—C61—H61109.0
C16—C14—H14109.5C62—C61—H61109.0
C14—C15—H15A109.5C61—C63—H63A109.5
C14—C15—H15B109.5C61—C63—H63B109.5
H15A—C15—H15B109.5H63A—C63—H63B109.5
C14—C15—H15C109.5C61—C63—H63C109.5
H15A—C15—H15C109.5H63A—C63—H63C109.5
H15B—C15—H15C109.5H63B—C63—H63C109.5
C14—C16—H16A109.5C61—C62—H62A109.5
C14—C16—H16B109.5C61—C62—H62B109.5
H16A—C16—H16B109.5H62A—C62—H62B109.5
C14—C16—H16C109.5C61—C62—H62C109.5
H16A—C16—H16C109.5H62A—C62—H62C109.5
H16B—C16—H16C109.5H62B—C62—H62C109.5
C7—O3—P1—S143.7 (2)C57—O53—P51—S5144.8 (2)
C7—O3—P1—O483.5 (2)C57—O53—P51—O5482.4 (2)
O3—P1—O4—C11162.78 (19)O53—P51—O54—C5137.56 (8)
P1—O4—C11—C12164.1 (2)P51—O54—C51—C5215.52 (19)
P1—O4—C11—C1370.6 (3)P51—O54—C51—C539.96 (11)
C7—O3—P1—O5171.25 (18)C57—O53—P51—O55172.49 (18)
O3—P1—O5—C1475.69 (19)O53—P51—O55—C546.69 (10)
P1—O5—C14—C15119.2 (2)P51—O55—C54—C55106.9 (2)
P1—O5—C14—C16118.2 (2)P51—O55—C54—C56111.45 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.982.583.420 (4)144
C60—H60C···O52ii0.962.513.444 (4)165
C64—H64···O52iii0.982.553.399 (4)145
Symmetry codes: (i) x, y1, z; (ii) x+2, y+1/2, z+1/2; (iii) x, y+1, z.
 

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