Hydrogen bonding and crystal packing play major roles in determining the conformations of ethyl methyl 2-(triphenylphosphoranylidene)malonate, Ph3P=C(CO2CH3)CO2CH2CH3 or C24H23O4P, (I), and dimethyl 2-(triphenylphosphoranylidene)malonate, Ph3P=C(CO2CH3)2 or C23H21O4P, (II). In (I), the acyl O atom of the ethyl ester group is anti to the P atom, while the O atom of the methyl ester group is syn. In (II), the dimethyl diester is a 1:1 mixture of anti-anti and syn-anti conformers.
Supporting information
CCDC references: 645589; 645590
For both compounds, data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 2001 ); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2001); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2003).
(I) methyl ethyl 2-(triphenylphosphoranylidene)malonate
top
Crystal data top
C24H23O4P | F(000) = 856 |
Mr = 406.39 | Dx = 1.285 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5668 reflections |
a = 14.3378 (17) Å | θ = 2.6–27.0° |
b = 9.1666 (11) Å | µ = 0.16 mm−1 |
c = 16.2696 (19) Å | T = 295 K |
β = 100.711 (2)° | Block, colourless |
V = 2101.0 (4) Å3 | 0.20 × 0.18 × 0.14 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2769 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 28.0°, θmin = 1.7° |
φ and ω scans | h = −18→17 |
17124 measured reflections | k = −11→11 |
4717 independent reflections | l = −20→21 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0625P)2] where P = (Fo2 + 2Fc2)/3 |
4717 reflections | (Δ/σ)max = 0.008 |
272 parameters | Δρmax = 0.32 e Å−3 |
34 restraints | Δρmin = −0.32 e Å−3 |
Special details top
Experimental. 1H NMR (CDCl3, δ, p.p.m.): 0.75 (t, 3H, J = 7 Hz), 3.39 (s, 3H), 3.79 (q,
2H, J = 7 Hz), 7.5–8.0 (m, 15H). IR (KBr): 1666.1 and 1616.0 (CO) cm-1. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.44976 (5) | 0.27189 (8) | 0.17940 (4) | 0.0426 (2) | |
O1 | 0.46992 (16) | 0.1093 (3) | 0.40156 (13) | 0.0762 (7) | |
O2 | 0.36472 (14) | 0.2502 (2) | 0.31977 (12) | 0.0567 (6) | |
O3 | 0.58270 (15) | 0.0162 (2) | 0.19209 (14) | 0.0730 (7) | |
O4 | 0.61944 (15) | 0.0130 (2) | 0.33139 (13) | 0.0707 (7) | |
C1 | 0.49027 (18) | 0.1568 (3) | 0.26359 (16) | 0.0429 (7) | |
C2 | 0.4371 (2) | 0.1776 (3) | 0.32872 (17) | 0.0476 (7) | |
C3 | 0.5696 (2) | 0.0586 (3) | 0.26900 (19) | 0.0492 (7) | |
C4 | 0.4129 (3) | 0.1323 (5) | 0.4673 (2) | 0.1041 (15) | |
H4A | 0.4408 | 0.0794 | 0.5167 | 0.156* | |
H4B | 0.3494 | 0.0980 | 0.4478 | 0.156* | |
H4C | 0.4115 | 0.2344 | 0.4801 | 0.156* | |
C5A | 0.6786 (2) | −0.0426 (5) | 0.1858 (3) | 0.0848 (17) | 0.804 (6) |
H5A1 | 0.7257 | −0.0079 | 0.2324 | 0.102* | 0.804 (6) |
H5A2 | 0.6966 | −0.0098 | 0.1343 | 0.102* | 0.804 (6) |
C6A | 0.6738 (5) | −0.2069 (5) | 0.1872 (4) | 0.140 (3) | 0.804 (6) |
H6A1 | 0.6703 | −0.2393 | 0.2427 | 0.209* | 0.804 (6) |
H6A2 | 0.7296 | −0.2468 | 0.1709 | 0.209* | 0.804 (6) |
H6A3 | 0.6185 | −0.2393 | 0.1489 | 0.209* | 0.804 (6) |
C5B | 0.6459 (14) | −0.1154 (15) | 0.2005 (15) | 0.0848 (17) | 0.196 (6) |
H5B1 | 0.6117 | −0.2025 | 0.1784 | 0.102* | 0.196 (6) |
H5B2 | 0.6766 | −0.1321 | 0.2581 | 0.102* | 0.196 (6) |
C6B | 0.7156 (18) | −0.066 (3) | 0.1471 (16) | 0.140 (3) | 0.196 (6) |
H6B1 | 0.6899 | −0.0860 | 0.0893 | 0.209* | 0.196 (6) |
H6B2 | 0.7743 | −0.1183 | 0.1633 | 0.209* | 0.196 (6) |
H6B3 | 0.7269 | 0.0364 | 0.1546 | 0.209* | 0.196 (6) |
C11 | 0.53019 (19) | 0.2768 (3) | 0.10623 (17) | 0.0456 (7) | |
C12 | 0.6149 (2) | 0.3521 (4) | 0.12467 (19) | 0.0637 (9) | |
H12 | 0.6283 | 0.4075 | 0.1733 | 0.076* | |
C13 | 0.6800 (2) | 0.3463 (4) | 0.0720 (2) | 0.0716 (10) | |
H13 | 0.7372 | 0.3962 | 0.0858 | 0.086* | |
C14 | 0.6606 (2) | 0.2678 (4) | 0.0001 (2) | 0.0680 (9) | |
H14 | 0.7048 | 0.2633 | −0.0351 | 0.082* | |
C15 | 0.5759 (2) | 0.1952 (4) | −0.0206 (2) | 0.0680 (9) | |
H15 | 0.5619 | 0.1433 | −0.0705 | 0.082* | |
C16 | 0.5114 (2) | 0.1992 (3) | 0.03270 (19) | 0.0587 (8) | |
H16 | 0.4544 | 0.1487 | 0.0186 | 0.070* | |
C21 | 0.33617 (19) | 0.2217 (3) | 0.11787 (16) | 0.0440 (7) | |
C22 | 0.2956 (2) | 0.3010 (3) | 0.04792 (18) | 0.0549 (8) | |
H22 | 0.3262 | 0.3837 | 0.0331 | 0.066* | |
C23 | 0.2100 (2) | 0.2587 (4) | −0.00013 (19) | 0.0653 (9) | |
H23 | 0.1824 | 0.3127 | −0.0467 | 0.078* | |
C24 | 0.1663 (2) | 0.1347 (4) | 0.0225 (2) | 0.0680 (10) | |
H24 | 0.1089 | 0.1050 | −0.0095 | 0.082* | |
C25 | 0.2059 (2) | 0.0551 (4) | 0.0907 (2) | 0.0640 (9) | |
H25 | 0.1755 | −0.0284 | 0.1048 | 0.077* | |
C26 | 0.2905 (2) | 0.0979 (3) | 0.13875 (18) | 0.0504 (7) | |
H26 | 0.3173 | 0.0434 | 0.1855 | 0.060* | |
C31 | 0.4442 (2) | 0.4553 (3) | 0.22059 (17) | 0.0463 (7) | |
C32 | 0.5195 (2) | 0.5011 (4) | 0.2813 (2) | 0.0678 (9) | |
H32 | 0.5701 | 0.4386 | 0.2999 | 0.081* | |
C33 | 0.5190 (3) | 0.6408 (4) | 0.3141 (2) | 0.0787 (11) | |
H33 | 0.5700 | 0.6724 | 0.3540 | 0.094* | |
C34 | 0.4442 (3) | 0.7321 (4) | 0.2883 (2) | 0.0744 (10) | |
H34 | 0.4444 | 0.8257 | 0.3103 | 0.089* | |
C35 | 0.3698 (3) | 0.6857 (4) | 0.2306 (2) | 0.0677 (9) | |
H35 | 0.3184 | 0.7475 | 0.2137 | 0.081* | |
C36 | 0.3691 (2) | 0.5473 (3) | 0.19629 (19) | 0.0569 (8) | |
H36 | 0.3174 | 0.5169 | 0.1566 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0431 (4) | 0.0373 (4) | 0.0454 (4) | 0.0001 (3) | 0.0032 (3) | 0.0028 (3) |
O1 | 0.0772 (16) | 0.0970 (18) | 0.0577 (14) | 0.0394 (13) | 0.0210 (12) | 0.0301 (13) |
O2 | 0.0536 (13) | 0.0574 (13) | 0.0585 (13) | 0.0184 (10) | 0.0084 (10) | 0.0076 (10) |
O3 | 0.0826 (17) | 0.0738 (16) | 0.0631 (14) | 0.0381 (13) | 0.0149 (12) | 0.0020 (12) |
O4 | 0.0623 (14) | 0.0813 (16) | 0.0606 (14) | 0.0291 (12) | −0.0088 (11) | 0.0014 (12) |
C1 | 0.0387 (15) | 0.0426 (16) | 0.0451 (16) | 0.0064 (12) | 0.0018 (13) | 0.0012 (13) |
C2 | 0.0497 (18) | 0.0436 (17) | 0.0459 (17) | 0.0038 (14) | −0.0004 (14) | 0.0049 (14) |
C3 | 0.0469 (17) | 0.0463 (18) | 0.0533 (19) | 0.0048 (14) | 0.0062 (15) | −0.0016 (15) |
C4 | 0.096 (3) | 0.149 (4) | 0.078 (2) | 0.062 (3) | 0.043 (2) | 0.056 (3) |
C5A | 0.094 (4) | 0.077 (3) | 0.092 (3) | 0.036 (3) | 0.041 (3) | 0.013 (3) |
C6A | 0.148 (5) | 0.135 (5) | 0.142 (5) | 0.034 (4) | 0.044 (4) | −0.013 (4) |
C5B | 0.094 (4) | 0.077 (3) | 0.092 (3) | 0.036 (3) | 0.041 (3) | 0.013 (3) |
C6B | 0.148 (5) | 0.135 (5) | 0.142 (5) | 0.034 (4) | 0.044 (4) | −0.013 (4) |
C11 | 0.0455 (17) | 0.0414 (16) | 0.0470 (16) | −0.0050 (13) | 0.0014 (13) | 0.0036 (13) |
C12 | 0.060 (2) | 0.076 (2) | 0.0546 (19) | −0.0194 (18) | 0.0096 (17) | −0.0096 (17) |
C13 | 0.059 (2) | 0.086 (3) | 0.070 (2) | −0.0316 (19) | 0.0121 (18) | 0.000 (2) |
C14 | 0.063 (2) | 0.082 (3) | 0.062 (2) | −0.0106 (19) | 0.0219 (18) | 0.0108 (19) |
C15 | 0.065 (2) | 0.085 (3) | 0.055 (2) | −0.0178 (19) | 0.0152 (17) | −0.0101 (18) |
C16 | 0.0492 (18) | 0.068 (2) | 0.0592 (19) | −0.0150 (16) | 0.0104 (15) | −0.0073 (16) |
C21 | 0.0434 (16) | 0.0419 (16) | 0.0463 (16) | 0.0005 (13) | 0.0069 (13) | 0.0013 (13) |
C22 | 0.0565 (19) | 0.0486 (19) | 0.0560 (18) | −0.0028 (15) | 0.0014 (15) | 0.0098 (15) |
C23 | 0.066 (2) | 0.070 (2) | 0.0534 (19) | 0.0021 (18) | −0.0072 (16) | 0.0003 (17) |
C24 | 0.0482 (19) | 0.085 (3) | 0.067 (2) | −0.0093 (19) | 0.0002 (17) | −0.018 (2) |
C25 | 0.061 (2) | 0.063 (2) | 0.067 (2) | −0.0183 (17) | 0.0116 (18) | −0.0079 (18) |
C26 | 0.0567 (19) | 0.0428 (17) | 0.0513 (17) | −0.0002 (14) | 0.0090 (15) | 0.0002 (14) |
C31 | 0.0485 (17) | 0.0389 (16) | 0.0511 (17) | −0.0024 (14) | 0.0087 (14) | 0.0017 (13) |
C32 | 0.061 (2) | 0.061 (2) | 0.079 (2) | 0.0010 (17) | 0.0063 (18) | −0.0193 (18) |
C33 | 0.077 (3) | 0.067 (2) | 0.091 (3) | −0.016 (2) | 0.013 (2) | −0.026 (2) |
C34 | 0.095 (3) | 0.0408 (19) | 0.096 (3) | −0.007 (2) | 0.038 (2) | −0.0099 (19) |
C35 | 0.082 (3) | 0.047 (2) | 0.078 (2) | 0.0089 (18) | 0.024 (2) | 0.0100 (17) |
C36 | 0.066 (2) | 0.0463 (18) | 0.0569 (19) | 0.0010 (16) | 0.0078 (16) | 0.0096 (15) |
Geometric parameters (Å, º) top
P1—C1 | 1.741 (3) | C13—C14 | 1.358 (4) |
P1—C11 | 1.805 (3) | C13—H13 | 0.9300 |
P1—C21 | 1.805 (3) | C14—C15 | 1.371 (4) |
P1—C31 | 1.817 (3) | C14—H14 | 0.9300 |
O1—C2 | 1.345 (3) | C15—C16 | 1.381 (4) |
O1—C4 | 1.477 (4) | C15—H15 | 0.9300 |
O2—C2 | 1.219 (3) | C16—H16 | 0.9300 |
O3—C3 | 1.356 (3) | C21—C26 | 1.384 (4) |
O3—C5B | 1.4997 (11) | C21—C22 | 1.384 (4) |
O3—C5A | 1.4982 (10) | C22—C23 | 1.382 (4) |
O4—C3 | 1.203 (3) | C22—H22 | 0.9300 |
C1—C2 | 1.428 (4) | C23—C24 | 1.380 (4) |
C1—C3 | 1.440 (4) | C23—H23 | 0.9300 |
C4—H4A | 0.9600 | C24—C25 | 1.361 (4) |
C4—H4B | 0.9600 | C24—H24 | 0.9300 |
C4—H4C | 0.9600 | C25—C26 | 1.373 (4) |
C5A—C6A | 1.5084 (11) | C25—H25 | 0.9300 |
C5A—H5A1 | 0.9700 | C26—H26 | 0.9300 |
C5A—H5A2 | 0.9700 | C31—C36 | 1.367 (4) |
C6A—H6A1 | 0.9600 | C31—C32 | 1.386 (4) |
C6A—H6A2 | 0.9600 | C32—C33 | 1.388 (4) |
C6A—H6A3 | 0.9600 | C32—H32 | 0.9300 |
C5B—C6B | 1.5102 (11) | C33—C34 | 1.363 (5) |
C5B—H5B1 | 0.9700 | C33—H33 | 0.9300 |
C5B—H5B2 | 0.9700 | C34—C35 | 1.352 (5) |
C6B—H6B1 | 0.96 | C34—H34 | 0.9300 |
C6B—H6B2 | 0.96 | C35—C36 | 1.385 (4) |
C6B—H6B3 | 0.96 | C35—H35 | 0.9300 |
C11—C12 | 1.380 (4) | C36—H36 | 0.9300 |
C11—C16 | 1.375 (4) | P1—O2 | 2.789 (2) |
C12—C13 | 1.381 (4) | P1—O3 | 3.004 (2) |
C12—H12 | 0.9300 | O1—O4 | 2.755 (3) |
| | | |
C1—P1—C11 | 111.92 (13) | H6B1—C6B—H6B3 | 110 |
C1—P1—C21 | 114.62 (13) | H6B2—C6B—H6B3 | 110 |
C11—P1—C21 | 105.16 (12) | C12—C11—C16 | 118.0 (3) |
C1—P1—C31 | 107.56 (13) | C12—C11—P1 | 120.9 (2) |
C11—P1—C31 | 107.30 (13) | C16—C11—P1 | 121.0 (2) |
C21—P1—C31 | 110.06 (13) | C11—C12—C13 | 121.0 (3) |
C1—P1—O2 | 56.31 (10) | C11—C12—H12 | 119.5 |
C11—P1—O2 | 166.38 (10) | C13—C12—H12 | 119.5 |
C21—P1—O2 | 87.10 (10) | C14—C13—C12 | 120.1 (3) |
C31—P1—O2 | 73.01 (10) | C14—C13—H13 | 119.9 |
C1—P1—O3 | 50.08 (10) | C12—C13—H13 | 120.0 |
C11—P1—O3 | 65.79 (10) | C13—C14—C15 | 119.9 (3) |
C21—P1—O3 | 109.57 (10) | C13—C14—H14 | 120.0 |
C31—P1—O3 | 140.13 (11) | C15—C14—H14 | 120.0 |
O2—P1—O3 | 104.87 (6) | C16—C15—C14 | 119.9 (3) |
C2—O1—C4 | 114.9 (2) | C16—C15—H15 | 120.0 |
C2—O1—O4 | 87.45 (17) | C14—C15—H15 | 120.0 |
C4—O1—O4 | 157.52 (18) | C11—C16—C15 | 121.0 (3) |
C2—O2—P1 | 69.18 (16) | C11—C16—H16 | 119.5 |
C3—O3—C5B | 109.3 (9) | C15—C16—H16 | 119.5 |
C3—O3—C5A | 116.9 (3) | C26—C21—C22 | 119.1 (3) |
C3—O3—P1 | 69.21 (15) | C26—C21—P1 | 119.4 (2) |
C5B—O3—P1 | 177.3 (7) | C22—C21—P1 | 121.4 (2) |
C5A—O3—P1 | 148.7 (2) | C21—C22—C23 | 120.7 (3) |
C3—O4—O1 | 81.51 (18) | C21—C22—H22 | 119.6 |
C2—C1—C3 | 124.2 (3) | C23—C22—H22 | 119.6 |
C2—C1—P1 | 110.9 (2) | C22—C23—C24 | 118.7 (3) |
C3—C1—P1 | 124.8 (2) | C22—C23—H23 | 120.7 |
O2—C2—O1 | 120.6 (3) | C24—C23—H23 | 120.7 |
O2—C2—C1 | 123.0 (3) | C25—C24—C23 | 121.2 (3) |
O1—C2—C1 | 116.4 (3) | C25—C24—H24 | 119.4 |
O4—C3—O3 | 121.1 (3) | C23—C24—H24 | 119.4 |
O4—C3—C1 | 127.4 (3) | C24—C25—C26 | 120.1 (3) |
O3—C3—C1 | 111.5 (2) | C24—C25—H25 | 119.9 |
O1—C4—H4A | 109.5 | C26—C25—H25 | 119.9 |
O1—C4—H4B | 109.5 | C21—C26—C25 | 120.2 (3) |
H4A—C4—H4B | 109.5 | C21—C26—H26 | 119.9 |
O1—C4—H4C | 109.5 | C25—C26—H26 | 119.9 |
H4A—C4—H4C | 109.5 | C36—C31—C32 | 119.1 (3) |
H4B—C4—H4C | 109.5 | C36—C31—P1 | 123.4 (2) |
O3—C5A—C6A | 108.2 (4) | C32—C31—P1 | 117.5 (2) |
O3—C5A—H5A1 | 110.1 | C31—C32—C33 | 119.6 (3) |
C6A—C5A—H5A1 | 110.1 | C31—C32—H32 | 120.2 |
O3—C5A—H5A2 | 110.1 | C33—C32—H32 | 120.2 |
C6A—C5A—H5A2 | 110.0 | C34—C33—C32 | 120.5 (3) |
H5A1—C5A—H5A2 | 108.4 | C34—C33—H33 | 119.7 |
O3—C5B—C6B | 99.3 (14) | C32—C33—H33 | 119.7 |
O3—C5B—H5B1 | 111.8 | C35—C34—C33 | 119.6 (3) |
C6B—C5B—H5B1 | 111.7 | C35—C34—H34 | 120.2 |
O3—C5B—H5B2 | 112.0 | C33—C34—H34 | 120.2 |
C6B—C5B—H5B2 | 112.2 | C34—C35—C36 | 120.9 (3) |
H5B1—C5B—H5B2 | 109.6 | C34—C35—H35 | 119.5 |
C5B—C6B—H6B1 | 109.0 | C36—C35—H35 | 119.5 |
C5B—C6B—H6B2 | 109.0 | C31—C36—C35 | 120.1 (3) |
H6B1—C6B—H6B2 | 109 | C31—C36—H36 | 119.9 |
C5B—C6B—H6B3 | 110 | C35—C36—H36 | 119.9 |
| | | |
P1—C1—C2—O2 | 10.2 (4) | P1—C1—C3—O4 | 154.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O4i | 0.93 | 2.48 | 3.376 (4) | 162 |
C25—H25···O2ii | 0.93 | 2.49 | 3.392 (4) | 162 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2. |
(II) dimethyl 2-(triphenylphosphoranylidene)malonate
top
Crystal data top
C23H21O4P | F(000) = 1648 |
Mr = 392.37 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6277 reflections |
a = 10.1031 (8) Å | θ = 2.3–26.5° |
b = 14.6961 (11) Å | µ = 0.17 mm−1 |
c = 26.756 (2) Å | T = 273 K |
β = 92.734 (1)° | Block, colourless |
V = 3968.1 (5) Å3 | 0.18 × 0.18 × 0.16 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6466 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 28.1°, θmin = 1.6° |
φ and ω scans | h = −13→13 |
33032 measured reflections | k = −19→19 |
8973 independent reflections | l = −34→33 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0708P)2 + 0.4925P] where P = (Fo2 + 2Fc2)/3 |
8973 reflections | (Δ/σ)max < 0.001 |
509 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. 1H NMR (CDCl3, δ, p.p.m.): 3.34 (s, 6H), 7.5–8.0 (m, 15H). IR (KBr):
1716.6, 1685.9 and 1628.4 (CO) cm-1. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.61745 (5) | 0.36378 (3) | 0.213009 (19) | 0.03310 (14) | |
O1 | 0.48785 (14) | 0.20077 (10) | 0.24484 (6) | 0.0493 (4) | |
O2 | 0.28520 (15) | 0.25678 (12) | 0.25339 (9) | 0.0748 (6) | |
O3 | 0.49442 (13) | 0.50540 (9) | 0.26611 (6) | 0.0440 (4) | |
O4 | 0.28666 (13) | 0.45071 (11) | 0.26383 (6) | 0.0546 (4) | |
C1 | 0.46488 (18) | 0.35641 (13) | 0.24016 (8) | 0.0358 (4) | |
C2 | 0.4000 (2) | 0.27085 (14) | 0.24599 (8) | 0.0417 (5) | |
C4 | 0.4335 (3) | 0.11157 (16) | 0.23834 (12) | 0.0723 (8) | |
H4A | 0.3830 | 0.0964 | 0.2667 | 0.108* | |
H4B | 0.5041 | 0.0684 | 0.2355 | 0.108* | |
H4C | 0.3769 | 0.1100 | 0.2085 | 0.108* | |
C3 | 0.40225 (19) | 0.43837 (14) | 0.25703 (7) | 0.0386 (5) | |
C5 | 0.4449 (2) | 0.59640 (15) | 0.27014 (10) | 0.0592 (7) | |
H5A | 0.3888 | 0.6104 | 0.2412 | 0.089* | |
H5B | 0.5179 | 0.6383 | 0.2723 | 0.089* | |
H5C | 0.3950 | 0.6015 | 0.2997 | 0.089* | |
C11 | 0.6213 (2) | 0.46969 (14) | 0.17900 (8) | 0.0396 (5) | |
C12 | 0.5114 (2) | 0.49521 (16) | 0.14906 (9) | 0.0527 (6) | |
H12 | 0.4384 | 0.4567 | 0.1457 | 0.063* | |
C13 | 0.5104 (3) | 0.57792 (18) | 0.12430 (10) | 0.0654 (7) | |
H13 | 0.4375 | 0.5942 | 0.1037 | 0.079* | |
C14 | 0.6163 (4) | 0.63587 (18) | 0.12996 (11) | 0.0749 (9) | |
H14 | 0.6152 | 0.6914 | 0.1133 | 0.090* | |
C15 | 0.7231 (3) | 0.61196 (19) | 0.16006 (12) | 0.0762 (9) | |
H15 | 0.7939 | 0.6520 | 0.1645 | 0.091* | |
C16 | 0.7273 (2) | 0.52880 (16) | 0.18413 (10) | 0.0557 (6) | |
H16 | 0.8018 | 0.5126 | 0.2039 | 0.067* | |
C21 | 0.75894 (19) | 0.36174 (13) | 0.25651 (8) | 0.0363 (4) | |
C22 | 0.7401 (2) | 0.37376 (14) | 0.30691 (8) | 0.0435 (5) | |
H22 | 0.6550 | 0.3808 | 0.3181 | 0.052* | |
C23 | 0.8478 (2) | 0.37534 (16) | 0.34048 (9) | 0.0552 (6) | |
H23 | 0.8354 | 0.3845 | 0.3743 | 0.066* | |
C24 | 0.9737 (2) | 0.36343 (17) | 0.32413 (10) | 0.0591 (7) | |
H24 | 1.0459 | 0.3640 | 0.3471 | 0.071* | |
C25 | 0.9937 (2) | 0.35075 (16) | 0.27457 (10) | 0.0555 (6) | |
H25 | 1.0790 | 0.3423 | 0.2638 | 0.067* | |
C26 | 0.8873 (2) | 0.35046 (15) | 0.24052 (9) | 0.0488 (6) | |
H26 | 0.9010 | 0.3427 | 0.2067 | 0.059* | |
C31 | 0.64474 (19) | 0.27403 (14) | 0.16818 (8) | 0.0377 (5) | |
C32 | 0.7124 (2) | 0.19526 (15) | 0.18286 (9) | 0.0481 (5) | |
H32 | 0.7452 | 0.1890 | 0.2157 | 0.058* | |
C33 | 0.7310 (3) | 0.12633 (17) | 0.14887 (10) | 0.0603 (7) | |
H33 | 0.7773 | 0.0742 | 0.1589 | 0.072* | |
C34 | 0.6818 (2) | 0.13439 (18) | 0.10054 (10) | 0.0608 (7) | |
H34 | 0.6929 | 0.0871 | 0.0780 | 0.073* | |
C35 | 0.6162 (2) | 0.21184 (18) | 0.08521 (9) | 0.0601 (7) | |
H35 | 0.5838 | 0.2175 | 0.0522 | 0.072* | |
C36 | 0.5984 (2) | 0.28166 (16) | 0.11895 (9) | 0.0507 (6) | |
H36 | 0.5546 | 0.3344 | 0.1083 | 0.061* | |
P2 | 0.14040 (5) | 0.23867 (3) | 0.019001 (19) | 0.03339 (14) | |
O5 | 0.26852 (13) | 0.39912 (9) | −0.01229 (6) | 0.0471 (4) | |
O6 | 0.47910 (14) | 0.35080 (10) | −0.00490 (7) | 0.0549 (4) | |
O7 | 0.48632 (13) | 0.17156 (10) | −0.03133 (6) | 0.0451 (4) | |
O8 | 0.29961 (14) | 0.09048 (9) | −0.02638 (6) | 0.0472 (4) | |
C6 | 0.29971 (18) | 0.24510 (13) | −0.00282 (7) | 0.0347 (4) | |
C7 | 0.36227 (19) | 0.33301 (14) | −0.00618 (8) | 0.0382 (5) | |
C8 | 0.35766 (19) | 0.16273 (14) | −0.02024 (7) | 0.0351 (4) | |
C9 | 0.3135 (3) | 0.49158 (15) | −0.00870 (12) | 0.0702 (8) | |
H9A | 0.3695 | 0.4989 | 0.0210 | 0.105* | |
H9B | 0.2385 | 0.5315 | −0.0073 | 0.105* | |
H9C | 0.3625 | 0.5063 | −0.0375 | 0.105* | |
C10 | 0.5552 (2) | 0.09001 (15) | −0.04373 (9) | 0.0513 (6) | |
H10A | 0.5767 | 0.0561 | −0.0138 | 0.077* | |
H10B | 0.6353 | 0.1055 | −0.0597 | 0.077* | |
H10C | 0.4999 | 0.0538 | −0.0661 | 0.077* | |
C41 | 0.1214 (2) | 0.13296 (13) | 0.05190 (7) | 0.0371 (4) | |
C42 | 0.2244 (2) | 0.10326 (15) | 0.08454 (8) | 0.0468 (5) | |
H42 | 0.3035 | 0.1357 | 0.0871 | 0.056* | |
C43 | 0.2090 (3) | 0.02589 (15) | 0.11297 (9) | 0.0531 (6) | |
H43 | 0.2772 | 0.0068 | 0.1351 | 0.064* | |
C44 | 0.0930 (3) | −0.02296 (16) | 0.10852 (9) | 0.0568 (6) | |
H44 | 0.0829 | −0.0749 | 0.1278 | 0.068* | |
C45 | −0.0076 (2) | 0.00419 (16) | 0.07597 (9) | 0.0543 (6) | |
H45 | −0.0851 | −0.0298 | 0.0728 | 0.065* | |
C46 | 0.0057 (2) | 0.08215 (14) | 0.04764 (8) | 0.0435 (5) | |
H46 | −0.0633 | 0.1006 | 0.0257 | 0.052* | |
C51 | 0.01025 (19) | 0.25060 (13) | −0.02921 (8) | 0.0365 (4) | |
C52 | 0.0442 (2) | 0.25322 (14) | −0.07856 (8) | 0.0418 (5) | |
H52 | 0.1323 | 0.2464 | −0.0864 | 0.050* | |
C53 | −0.0517 (2) | 0.26588 (16) | −0.11641 (9) | 0.0520 (6) | |
H53 | −0.0279 | 0.2672 | −0.1495 | 0.062* | |
C54 | −0.1818 (2) | 0.27657 (16) | −0.10534 (10) | 0.0568 (6) | |
H54 | −0.2459 | 0.2855 | −0.1310 | 0.068* | |
C55 | −0.2179 (2) | 0.27408 (16) | −0.05650 (10) | 0.0551 (6) | |
H55 | −0.3063 | 0.2810 | −0.0491 | 0.066* | |
C56 | −0.1227 (2) | 0.26128 (15) | −0.01841 (9) | 0.0471 (5) | |
H56 | −0.1473 | 0.2598 | 0.0146 | 0.057* | |
C61 | 0.1127 (2) | 0.32753 (14) | 0.06472 (8) | 0.0386 (5) | |
C62 | 0.0396 (2) | 0.40447 (16) | 0.05198 (9) | 0.0541 (6) | |
H62 | 0.0013 | 0.4105 | 0.0198 | 0.065* | |
C63 | 0.0232 (3) | 0.47256 (19) | 0.08692 (11) | 0.0701 (8) | |
H63 | −0.0270 | 0.5238 | 0.0784 | 0.084* | |
C64 | 0.0807 (3) | 0.4644 (2) | 0.13388 (11) | 0.0704 (8) | |
H64 | 0.0709 | 0.5108 | 0.1570 | 0.084* | |
C65 | 0.1523 (3) | 0.3890 (2) | 0.14717 (10) | 0.0657 (7) | |
H65 | 0.1904 | 0.3836 | 0.1794 | 0.079* | |
C66 | 0.1682 (2) | 0.32040 (17) | 0.11259 (8) | 0.0521 (6) | |
H66 | 0.2169 | 0.2689 | 0.1218 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0283 (3) | 0.0337 (3) | 0.0373 (3) | 0.0004 (2) | 0.0021 (2) | 0.0015 (2) |
O1 | 0.0384 (8) | 0.0368 (8) | 0.0732 (11) | −0.0006 (6) | 0.0053 (7) | 0.0083 (7) |
O2 | 0.0349 (9) | 0.0505 (10) | 0.1404 (18) | −0.0066 (7) | 0.0190 (10) | 0.0102 (11) |
O3 | 0.0344 (8) | 0.0384 (8) | 0.0595 (10) | −0.0022 (6) | 0.0044 (7) | −0.0087 (7) |
O4 | 0.0309 (8) | 0.0565 (10) | 0.0773 (12) | 0.0005 (7) | 0.0098 (7) | −0.0159 (8) |
C1 | 0.0276 (10) | 0.0372 (11) | 0.0425 (12) | −0.0019 (8) | 0.0022 (8) | −0.0006 (9) |
C2 | 0.0331 (11) | 0.0430 (12) | 0.0489 (13) | −0.0007 (9) | 0.0005 (9) | 0.0066 (10) |
C4 | 0.0665 (18) | 0.0385 (14) | 0.111 (2) | −0.0067 (12) | −0.0016 (16) | 0.0104 (14) |
C3 | 0.0307 (10) | 0.0455 (12) | 0.0395 (11) | −0.0014 (9) | 0.0014 (9) | −0.0025 (9) |
C5 | 0.0559 (15) | 0.0416 (14) | 0.0804 (19) | −0.0001 (11) | 0.0068 (13) | −0.0079 (12) |
C11 | 0.0400 (11) | 0.0388 (12) | 0.0405 (12) | 0.0020 (9) | 0.0070 (9) | 0.0026 (9) |
C12 | 0.0583 (15) | 0.0467 (14) | 0.0529 (15) | 0.0063 (11) | 0.0020 (11) | 0.0063 (11) |
C13 | 0.086 (2) | 0.0529 (16) | 0.0576 (16) | 0.0204 (14) | 0.0003 (14) | 0.0127 (12) |
C14 | 0.116 (3) | 0.0428 (15) | 0.0674 (19) | 0.0037 (16) | 0.0219 (18) | 0.0169 (13) |
C15 | 0.096 (2) | 0.0527 (17) | 0.081 (2) | −0.0266 (15) | 0.0141 (18) | 0.0153 (15) |
C16 | 0.0531 (14) | 0.0501 (14) | 0.0643 (16) | −0.0120 (11) | 0.0079 (12) | 0.0099 (12) |
C21 | 0.0305 (10) | 0.0361 (11) | 0.0420 (12) | −0.0005 (8) | −0.0004 (8) | 0.0016 (9) |
C22 | 0.0374 (11) | 0.0467 (13) | 0.0463 (13) | 0.0004 (9) | 0.0012 (9) | 0.0014 (10) |
C23 | 0.0559 (15) | 0.0621 (16) | 0.0463 (14) | 0.0013 (12) | −0.0099 (11) | −0.0028 (11) |
C24 | 0.0472 (14) | 0.0633 (17) | 0.0649 (17) | −0.0018 (11) | −0.0179 (12) | −0.0018 (13) |
C25 | 0.0296 (11) | 0.0609 (16) | 0.0758 (18) | 0.0007 (10) | −0.0012 (11) | −0.0012 (13) |
C26 | 0.0348 (11) | 0.0588 (15) | 0.0529 (14) | 0.0009 (10) | 0.0051 (10) | −0.0022 (11) |
C31 | 0.0335 (10) | 0.0388 (11) | 0.0408 (12) | 0.0006 (8) | 0.0024 (9) | −0.0029 (9) |
C32 | 0.0498 (13) | 0.0459 (13) | 0.0482 (13) | 0.0087 (10) | −0.0012 (10) | −0.0024 (10) |
C33 | 0.0632 (16) | 0.0458 (14) | 0.0714 (18) | 0.0138 (12) | −0.0013 (13) | −0.0098 (12) |
C34 | 0.0584 (16) | 0.0615 (16) | 0.0624 (17) | 0.0047 (12) | 0.0028 (13) | −0.0244 (13) |
C35 | 0.0608 (15) | 0.0728 (18) | 0.0458 (14) | 0.0064 (13) | −0.0073 (11) | −0.0154 (13) |
C36 | 0.0516 (13) | 0.0516 (14) | 0.0485 (14) | 0.0070 (11) | −0.0021 (11) | −0.0035 (11) |
P2 | 0.0311 (3) | 0.0332 (3) | 0.0360 (3) | −0.0008 (2) | 0.0028 (2) | 0.0007 (2) |
O5 | 0.0356 (8) | 0.0338 (8) | 0.0721 (11) | 0.0006 (6) | 0.0047 (7) | 0.0061 (7) |
O6 | 0.0321 (8) | 0.0422 (9) | 0.0902 (13) | −0.0053 (6) | 0.0001 (8) | 0.0035 (8) |
O7 | 0.0337 (8) | 0.0427 (8) | 0.0597 (10) | 0.0001 (6) | 0.0106 (7) | −0.0071 (7) |
O8 | 0.0445 (9) | 0.0374 (8) | 0.0604 (10) | −0.0076 (7) | 0.0089 (7) | −0.0073 (7) |
C6 | 0.0300 (10) | 0.0340 (11) | 0.0402 (11) | −0.0020 (8) | 0.0028 (8) | 0.0015 (8) |
C7 | 0.0336 (11) | 0.0377 (11) | 0.0432 (12) | −0.0017 (9) | 0.0003 (9) | 0.0031 (9) |
C8 | 0.0332 (10) | 0.0397 (11) | 0.0324 (11) | −0.0007 (9) | 0.0019 (8) | 0.0033 (8) |
C9 | 0.0587 (16) | 0.0330 (13) | 0.120 (3) | −0.0014 (11) | 0.0099 (16) | 0.0009 (14) |
C10 | 0.0442 (13) | 0.0505 (14) | 0.0598 (15) | 0.0107 (10) | 0.0085 (11) | −0.0033 (11) |
C41 | 0.0388 (11) | 0.0366 (11) | 0.0364 (11) | 0.0004 (9) | 0.0072 (9) | 0.0011 (8) |
C42 | 0.0459 (13) | 0.0464 (13) | 0.0482 (13) | 0.0010 (10) | 0.0028 (10) | 0.0050 (10) |
C43 | 0.0684 (16) | 0.0454 (14) | 0.0455 (13) | 0.0115 (12) | 0.0030 (11) | 0.0055 (11) |
C44 | 0.0817 (18) | 0.0354 (13) | 0.0548 (15) | −0.0013 (12) | 0.0188 (13) | 0.0046 (11) |
C45 | 0.0605 (15) | 0.0421 (13) | 0.0615 (16) | −0.0126 (11) | 0.0165 (13) | −0.0022 (11) |
C46 | 0.0442 (12) | 0.0392 (12) | 0.0475 (13) | −0.0038 (9) | 0.0078 (10) | −0.0005 (9) |
C51 | 0.0341 (10) | 0.0327 (11) | 0.0425 (12) | 0.0007 (8) | 0.0009 (9) | 0.0016 (9) |
C52 | 0.0400 (11) | 0.0409 (12) | 0.0444 (13) | −0.0011 (9) | 0.0015 (9) | 0.0001 (9) |
C53 | 0.0604 (15) | 0.0509 (14) | 0.0438 (13) | −0.0018 (11) | −0.0068 (11) | 0.0021 (10) |
C54 | 0.0505 (14) | 0.0507 (14) | 0.0669 (18) | −0.0014 (11) | −0.0198 (12) | 0.0054 (12) |
C55 | 0.0349 (12) | 0.0493 (14) | 0.0806 (19) | 0.0008 (10) | −0.0030 (12) | 0.0063 (12) |
C56 | 0.0378 (12) | 0.0489 (13) | 0.0550 (14) | 0.0025 (10) | 0.0054 (10) | 0.0043 (10) |
C61 | 0.0371 (11) | 0.0395 (11) | 0.0397 (12) | −0.0027 (9) | 0.0060 (9) | −0.0033 (9) |
C62 | 0.0626 (15) | 0.0486 (14) | 0.0510 (14) | 0.0124 (11) | 0.0008 (11) | −0.0077 (11) |
C63 | 0.082 (2) | 0.0580 (17) | 0.0704 (19) | 0.0196 (14) | 0.0062 (15) | −0.0152 (14) |
C64 | 0.0803 (19) | 0.0687 (19) | 0.0630 (18) | 0.0000 (15) | 0.0136 (15) | −0.0270 (15) |
C65 | 0.0695 (18) | 0.082 (2) | 0.0457 (15) | −0.0074 (15) | 0.0018 (13) | −0.0160 (13) |
C66 | 0.0526 (14) | 0.0580 (15) | 0.0454 (14) | 0.0031 (11) | −0.0011 (11) | −0.0056 (11) |
Geometric parameters (Å, º) top
P1—C1 | 1.738 (2) | P2—C6 | 1.7408 (19) |
P1—C21 | 1.800 (2) | P2—C41 | 1.800 (2) |
P1—C11 | 1.804 (2) | P2—C51 | 1.806 (2) |
P1—C31 | 1.813 (2) | P2—C61 | 1.820 (2) |
O1—C2 | 1.361 (2) | O5—C7 | 1.361 (2) |
O1—C4 | 1.429 (3) | O5—C9 | 1.434 (3) |
O2—C2 | 1.204 (2) | O6—C7 | 1.208 (2) |
O3—C3 | 1.369 (2) | O7—C8 | 1.353 (2) |
O3—C5 | 1.434 (3) | O7—C10 | 1.433 (2) |
O4—C3 | 1.204 (2) | O8—C8 | 1.220 (2) |
C1—C2 | 1.430 (3) | C6—C8 | 1.432 (3) |
C1—C3 | 1.443 (3) | C6—C7 | 1.443 (3) |
C4—H4A | 0.9600 | C9—H9A | 0.9600 |
C4—H4B | 0.9600 | C9—H9B | 0.9600 |
C4—H4C | 0.9600 | C9—H9C | 0.9600 |
C5—H5A | 0.9600 | C10—H10A | 0.9600 |
C5—H5B | 0.9600 | C10—H10B | 0.9600 |
C5—H5C | 0.9600 | C10—H10C | 0.9600 |
C11—C16 | 1.380 (3) | C41—C46 | 1.387 (3) |
C11—C12 | 1.390 (3) | C41—C42 | 1.396 (3) |
C12—C13 | 1.384 (3) | C42—C43 | 1.381 (3) |
C12—H12 | 0.9300 | C42—H42 | 0.9300 |
C13—C14 | 1.370 (4) | C43—C44 | 1.375 (3) |
C13—H13 | 0.9300 | C43—H43 | 0.9300 |
C14—C15 | 1.361 (4) | C44—C45 | 1.366 (3) |
C14—H14 | 0.9300 | C44—H44 | 0.9300 |
C15—C16 | 1.381 (3) | C45—C46 | 1.384 (3) |
C15—H15 | 0.9300 | C45—H45 | 0.9300 |
C16—H16 | 0.9300 | C46—H46 | 0.9300 |
C21—C22 | 1.382 (3) | C51—C52 | 1.380 (3) |
C21—C26 | 1.394 (3) | C51—C56 | 1.397 (3) |
C22—C23 | 1.378 (3) | C52—C53 | 1.380 (3) |
C22—H22 | 0.9300 | C52—H52 | 0.9300 |
C23—C24 | 1.376 (3) | C53—C54 | 1.370 (3) |
C23—H23 | 0.9300 | C53—H53 | 0.9300 |
C24—C25 | 1.363 (4) | C54—C55 | 1.374 (4) |
C24—H24 | 0.9300 | C54—H54 | 0.9300 |
C25—C26 | 1.376 (3) | C55—C56 | 1.380 (3) |
C25—H25 | 0.9300 | C55—H55 | 0.9300 |
C26—H26 | 0.9300 | C56—H56 | 0.9300 |
C31—C36 | 1.382 (3) | C61—C66 | 1.378 (3) |
C31—C32 | 1.391 (3) | C61—C62 | 1.384 (3) |
C32—C33 | 1.380 (3) | C62—C63 | 1.385 (3) |
C32—H32 | 0.9300 | C62—H62 | 0.9300 |
C33—C34 | 1.368 (4) | C63—C64 | 1.364 (4) |
C33—H33 | 0.9300 | C63—H63 | 0.9300 |
C34—C35 | 1.370 (3) | C64—C65 | 1.361 (4) |
C34—H34 | 0.9300 | C64—H64 | 0.9300 |
C35—C36 | 1.384 (3) | C65—C66 | 1.383 (3) |
C35—H35 | 0.9300 | C65—H65 | 0.9300 |
C36—H36 | 0.9300 | C66—H66 | 0.9300 |
P1—O3 | 2.8396 (15) | P2—O5 | 2.8355 (14) |
P1—O1 | 2.8784 (15) | P2—O8 | 2.9985 (15) |
O2—O4 | 2.864 (2) | O6—O7 | 2.729 (2) |
| | | |
C1—P1—C21 | 114.92 (10) | C6—P2—C41 | 109.43 (9) |
C1—P1—C11 | 107.80 (9) | C6—P2—C51 | 114.11 (9) |
C21—P1—C11 | 107.75 (9) | C41—P2—C51 | 110.00 (9) |
C1—P1—C31 | 113.39 (9) | C6—P2—C61 | 111.15 (9) |
C21—P1—C31 | 105.93 (9) | C41—P2—C61 | 105.49 (9) |
C11—P1—C31 | 106.64 (10) | C51—P2—C61 | 106.28 (9) |
C1—P1—O3 | 54.45 (7) | C6—P2—O5 | 54.08 (7) |
C21—P1—O3 | 92.40 (7) | C41—P2—O5 | 157.33 (8) |
C11—P1—O3 | 68.94 (7) | C51—P2—O5 | 92.03 (7) |
C31—P1—O3 | 161.51 (7) | C61—P2—O5 | 71.87 (7) |
C1—P1—O1 | 53.10 (7) | C6—P2—O8 | 51.76 (7) |
C21—P1—O1 | 98.81 (7) | C41—P2—O8 | 69.08 (7) |
C11—P1—O1 | 152.66 (7) | C51—P2—O8 | 99.65 (7) |
C31—P1—O1 | 71.08 (7) | C61—P2—O8 | 153.63 (7) |
O3—P1—O1 | 104.23 (5) | O5—P2—O8 | 102.90 (4) |
C2—O1—C4 | 116.74 (17) | C7—O5—C9 | 116.86 (16) |
C2—O1—P1 | 71.53 (11) | C7—O5—P2 | 72.29 (10) |
C4—O1—P1 | 154.86 (16) | C9—O5—P2 | 156.28 (16) |
C2—O2—O4 | 81.05 (13) | C7—O6—O7 | 79.74 (12) |
C3—O3—C5 | 116.61 (16) | C8—O7—C10 | 116.94 (16) |
C3—O3—P1 | 72.19 (10) | C8—O7—O6 | 89.88 (11) |
C5—O3—P1 | 152.12 (14) | C10—O7—O6 | 152.44 (13) |
C3—O4—O2 | 80.55 (13) | C8—O8—P2 | 64.99 (11) |
C2—C1—C3 | 119.32 (17) | C8—C6—C7 | 123.32 (17) |
C2—C1—P1 | 121.38 (15) | C8—C6—P2 | 117.53 (14) |
C3—C1—P1 | 119.30 (14) | C7—C6—P2 | 118.96 (15) |
O2—C2—O1 | 120.55 (19) | O6—C7—O5 | 121.48 (18) |
O2—C2—C1 | 128.3 (2) | O6—C7—C6 | 128.49 (19) |
O1—C2—C1 | 111.10 (17) | O5—C7—C6 | 110.01 (16) |
O1—C4—H4A | 109.5 | O8—C8—O7 | 120.96 (18) |
O1—C4—H4B | 109.5 | O8—C8—C6 | 125.30 (18) |
H4A—C4—H4B | 109.5 | O7—C8—C6 | 113.71 (17) |
O1—C4—H4C | 109.5 | O5—C9—H9A | 109.5 |
H4A—C4—H4C | 109.5 | O5—C9—H9B | 109.5 |
H4B—C4—H4C | 109.5 | H9A—C9—H9B | 109.5 |
O4—C3—O3 | 121.40 (19) | O5—C9—H9C | 109.5 |
O4—C3—C1 | 128.02 (19) | H9A—C9—H9C | 109.5 |
O3—C3—C1 | 110.57 (16) | H9B—C9—H9C | 109.5 |
O3—C5—H5A | 109.5 | O7—C10—H10A | 109.5 |
O3—C5—H5B | 109.5 | O7—C10—H10B | 109.5 |
H5A—C5—H5B | 109.5 | H10A—C10—H10B | 109.5 |
O3—C5—H5C | 109.5 | O7—C10—H10C | 109.5 |
H5A—C5—H5C | 109.5 | H10A—C10—H10C | 109.5 |
H5B—C5—H5C | 109.5 | H10B—C10—H10C | 109.5 |
C16—C11—C12 | 118.8 (2) | C46—C41—C42 | 118.89 (19) |
C16—C11—P1 | 121.89 (17) | C46—C41—P2 | 122.23 (16) |
C12—C11—P1 | 119.17 (17) | C42—C41—P2 | 118.81 (16) |
C13—C12—C11 | 120.0 (2) | C43—C42—C41 | 120.1 (2) |
C13—C12—H12 | 120.0 | C43—C42—H42 | 119.9 |
C11—C12—H12 | 120.0 | C41—C42—H42 | 119.9 |
C14—C13—C12 | 120.4 (3) | C44—C43—C42 | 120.0 (2) |
C14—C13—H13 | 119.8 | C44—C43—H43 | 120.0 |
C12—C13—H13 | 119.8 | C42—C43—H43 | 120.0 |
C15—C14—C13 | 119.8 (2) | C45—C44—C43 | 120.5 (2) |
C15—C14—H14 | 120.1 | C45—C44—H44 | 119.7 |
C13—C14—H14 | 120.1 | C43—C44—H44 | 119.7 |
C14—C15—C16 | 120.7 (3) | C44—C45—C46 | 120.2 (2) |
C14—C15—H15 | 119.7 | C44—C45—H45 | 119.9 |
C16—C15—H15 | 119.7 | C46—C45—H45 | 119.9 |
C11—C16—C15 | 120.3 (2) | C45—C46—C41 | 120.3 (2) |
C11—C16—H16 | 119.9 | C45—C46—H46 | 119.9 |
C15—C16—H16 | 119.9 | C41—C46—H46 | 119.9 |
C22—C21—C26 | 119.20 (19) | C52—C51—C56 | 118.67 (19) |
C22—C21—P1 | 119.12 (15) | C52—C51—P2 | 118.71 (15) |
C26—C21—P1 | 121.66 (16) | C56—C51—P2 | 122.55 (16) |
C23—C22—C21 | 119.8 (2) | C53—C52—C51 | 120.5 (2) |
C23—C22—H22 | 120.1 | C53—C52—H52 | 119.7 |
C21—C22—H22 | 120.1 | C51—C52—H52 | 119.7 |
C24—C23—C22 | 120.3 (2) | C54—C53—C52 | 120.3 (2) |
C24—C23—H23 | 119.9 | C54—C53—H53 | 119.9 |
C22—C23—H23 | 119.9 | C52—C53—H53 | 119.9 |
C25—C24—C23 | 120.5 (2) | C53—C54—C55 | 120.2 (2) |
C25—C24—H24 | 119.7 | C53—C54—H54 | 119.9 |
C23—C24—H24 | 119.7 | C55—C54—H54 | 119.9 |
C24—C25—C26 | 119.8 (2) | C54—C55—C56 | 119.9 (2) |
C24—C25—H25 | 120.1 | C54—C55—H55 | 120.0 |
C26—C25—H25 | 120.1 | C56—C55—H55 | 120.0 |
C25—C26—C21 | 120.3 (2) | C55—C56—C51 | 120.4 (2) |
C25—C26—H26 | 119.8 | C55—C56—H56 | 119.8 |
C21—C26—H26 | 119.8 | C51—C56—H56 | 119.8 |
C36—C31—C32 | 118.5 (2) | C66—C61—C62 | 118.7 (2) |
C36—C31—P1 | 121.09 (16) | C66—C61—P2 | 120.10 (17) |
C32—C31—P1 | 120.46 (16) | C62—C61—P2 | 121.19 (17) |
C33—C32—C31 | 120.4 (2) | C61—C62—C63 | 120.2 (2) |
C33—C32—H32 | 119.8 | C61—C62—H62 | 119.9 |
C31—C32—H32 | 119.8 | C63—C62—H62 | 119.9 |
C34—C33—C32 | 120.3 (2) | C64—C63—C62 | 119.9 (3) |
C34—C33—H33 | 119.9 | C64—C63—H63 | 120.0 |
C32—C33—H33 | 119.9 | C62—C63—H63 | 120.0 |
C33—C34—C35 | 120.2 (2) | C65—C64—C63 | 120.7 (2) |
C33—C34—H34 | 119.9 | C65—C64—H64 | 119.7 |
C35—C34—H34 | 119.9 | C63—C64—H64 | 119.7 |
C34—C35—C36 | 119.8 (2) | C64—C65—C66 | 119.7 (2) |
C34—C35—H35 | 120.1 | C64—C65—H65 | 120.1 |
C36—C35—H35 | 120.1 | C66—C65—H65 | 120.1 |
C31—C36—C35 | 120.9 (2) | C61—C66—C65 | 120.8 (2) |
C31—C36—H36 | 119.6 | C61—C66—H66 | 119.6 |
C35—C36—H36 | 119.6 | C65—C66—H66 | 119.6 |
| | | |
P1—C1—C2—O2 | −162.0 (2) | P2—C6—C7—O6 | 154.6 (2) |
P1—C1—C3—O4 | 158.20 (19) | P2—C6—C8—O8 | 8.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···O2i | 0.93 | 2.46 | 3.326 (3) | 155 |
C35—H35···O7 | 0.93 | 2.49 | 3.377 (3) | 159 |
Symmetry code: (i) x+1, y, z. |