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The asymmetric unit of the title compound, C
16H
21O
5PS, 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
CCDC reference: 271816
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (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
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
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 |
Data collection top
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 top
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 |
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 | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
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