Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012438/rz2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012438/rz2019Isup2.hkl |
CCDC reference: 608604
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
C40H33NO3P2 | Z = 2 |
Mr = 637.61 | F(000) = 668 |
Triclinic, P1 | Dx = 1.268 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.431 (2) Å | Cell parameters from 21372 reflections |
b = 11.354 (2) Å | θ = 3.0–25.4° |
c = 15.337 (3) Å | µ = 0.17 mm−1 |
α = 68.961 (6)° | T = 291 K |
β = 84.619 (10)° | Plate, pale yellow |
γ = 80.182 (9)° | 0.26 × 0.16 × 0.08 mm |
V = 1669.5 (5) Å3 |
Nonius KappaCCD diffractometer | 2007 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.4°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −12→12 |
235 frames via ω–rotation (Δω=2°) and two times 75 s per frame (five sets at different κ–angles) scans | k = −13→13 |
21372 measured reflections | l = −18→18 |
6052 independent reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.01 | w = [exp{4.20(sinθ/λ}2)]/[σ2(Fo2)] |
6052 reflections | (Δ/σ)max < 0.001 |
424 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Experimental. 1H NMR (500 MHz, C6D6): δ 2.27 (t, 2H,J = 7.5 Hz), 3.36 (s, 3H), 3.52 (t, 2H, J = 7.5 Hz), 6.22 (d, 2H, J = 8.0 Hz), 6.41 (d, 2H, J = 7.5 Hz), 6.54 (dd, 2H, J = 7.5, J = 8.0 Hz), 7.1 (bs, 12H), 7.5 (bs, 8H); 13C NMR (125 MHz, C6D6): δ 30.8 (CH2), 41.2 (CH2), 52.5 (CH3), 113.2 (CH), 125.5 (CH), 127.2 (CH), 129.8 (m, CH), 134.1 (C), 135.7 (m, CH), 139.0 (C), 139.0 (C), 172.6 (C); 31P NMR (81 MHz, C6D6): δ -17.5; IR (KBr plate; ν cm-1): 694 (s), 744 (s), 1222 (s), 1279 (s), 1377 (s), 1417 (vs), 1462 (s), 1552 (s), 1577 (m), 1724 (s), 2949 (w), 2999 (w), 3051 (w), 3064 (w) |
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 | Occ. (<1) | |
P1 | −0.21268 (9) | 0.76267 (8) | 0.23814 (6) | 0.0887 (3) | |
P2 | 0.01709 (8) | 0.39899 (8) | 0.34018 (6) | 0.0825 (3) | |
N1 | −0.1786 (2) | 0.5021 (2) | 0.02021 (16) | 0.0883 (8) | |
O1 | −0.12040 (19) | 0.55383 (18) | 0.17535 (13) | 0.0928 (7) | |
O2 | −0.4265 (3) | 0.3867 (3) | −0.1688 (2) | 0.1552 (11) | |
O3 | −0.4828 (8) | 0.5587 (10) | −0.1623 (7) | 0.179 (3) | 0.50 |
O3' | −0.3610 (10) | 0.5618 (12) | −0.2104 (5) | 0.184 (4) | 0.50 |
C1 | −0.2057 (3) | 0.4790 (3) | −0.0632 (2) | 0.0989 (10) | |
H1A | −0.1326 | 0.4227 | −0.0775 | 0.119* | |
H1B | −0.2135 | 0.5593 | −0.1154 | 0.119* | |
C2 | −0.3286 (3) | 0.4203 (3) | −0.0538 (2) | 0.1104 (12) | |
H2A | −0.3066 | 0.3282 | −0.0328 | 0.132* | |
H2B | −0.3871 | 0.4418 | −0.0069 | 0.132* | |
C3 | −0.3955 (7) | 0.4659 (4) | −0.1434 (4) | 0.1271 (16) | |
C4 | −0.4983 (4) | 0.4368 (5) | −0.2563 (3) | 0.207 (2) | |
H4A | −0.5213 | 0.3671 | −0.2700 | 0.310* | |
H4B | −0.4443 | 0.4838 | −0.3065 | 0.310* | |
H4C | −0.5759 | 0.4921 | −0.2491 | 0.310* | |
C11 | −0.2565 (3) | 0.7506 (3) | 0.12879 (19) | 0.0788 (9) | |
C12 | −0.2070 (3) | 0.6397 (3) | 0.1111 (2) | 0.0764 (8) | |
C13 | −0.2370 (3) | 0.6151 (3) | 0.0334 (2) | 0.0794 (9) | |
C14 | −0.3243 (3) | 0.7058 (3) | −0.0275 (2) | 0.0949 (10) | |
H14A | −0.3487 | 0.6916 | −0.0793 | 0.114* | |
C15 | −0.3757 (3) | 0.8174 (3) | −0.0121 (2) | 0.1071 (12) | |
H15A | −0.4334 | 0.8780 | −0.0541 | 0.129* | |
C16 | −0.3427 (3) | 0.8404 (3) | 0.0647 (2) | 0.0988 (11) | |
H16A | −0.3780 | 0.9163 | 0.0738 | 0.119* | |
C21 | −0.0109 (3) | 0.3461 (3) | 0.2448 (2) | 0.0747 (8) | |
C22 | −0.0809 (3) | 0.4329 (3) | 0.1706 (2) | 0.0749 (8) | |
C23 | −0.1083 (3) | 0.4068 (3) | 0.0927 (2) | 0.0783 (8) | |
C24 | −0.0598 (3) | 0.2863 (3) | 0.0902 (2) | 0.0917 (10) | |
H24A | −0.0770 | 0.2645 | 0.0399 | 0.110* | |
C25 | 0.0138 (3) | 0.1988 (3) | 0.1620 (3) | 0.1004 (11) | |
H25A | 0.0477 | 0.1192 | 0.1587 | 0.120* | |
C26 | 0.0380 (3) | 0.2268 (3) | 0.2385 (2) | 0.0907 (10) | |
H26A | 0.0873 | 0.1660 | 0.2863 | 0.109* | |
C31 | −0.3145 (4) | 0.9125 (3) | 0.2354 (2) | 0.0818 (9) | |
C32 | −0.4383 (4) | 0.9043 (3) | 0.2755 (2) | 0.1052 (11) | |
H32A | −0.4660 | 0.8248 | 0.3007 | 0.126* | |
C33 | −0.5229 (4) | 1.0112 (5) | 0.2795 (3) | 0.1156 (13) | |
H33A | −0.6066 | 1.0034 | 0.3055 | 0.139* | |
C34 | −0.4817 (4) | 1.1270 (4) | 0.2450 (3) | 0.1081 (14) | |
H34A | −0.5370 | 1.1989 | 0.2483 | 0.130* | |
C35 | −0.3588 (4) | 1.1386 (3) | 0.2053 (2) | 0.1015 (11) | |
H35A | −0.3310 | 1.2180 | 0.1819 | 0.122* | |
C36 | −0.2757 (3) | 1.0308 (3) | 0.2002 (2) | 0.0919 (10) | |
H36A | −0.1930 | 1.0393 | 0.1725 | 0.110* | |
C41 | −0.0491 (3) | 0.8074 (3) | 0.2077 (3) | 0.0856 (10) | |
C42 | 0.0046 (4) | 0.8527 (3) | 0.1179 (3) | 0.1004 (11) | |
H42A | −0.0445 | 0.8634 | 0.0673 | 0.121* | |
C43 | 0.1297 (5) | 0.8822 (3) | 0.1023 (3) | 0.1187 (13) | |
H43A | 0.1641 | 0.9117 | 0.0415 | 0.142* | |
C44 | 0.2038 (4) | 0.8686 (4) | 0.1755 (5) | 0.1404 (18) | |
H44A | 0.2878 | 0.8891 | 0.1649 | 0.168* | |
C45 | 0.1517 (6) | 0.8244 (4) | 0.2640 (4) | 0.147 (2) | |
H45A | 0.2011 | 0.8152 | 0.3142 | 0.177* | |
C46 | 0.0273 (5) | 0.7931 (3) | 0.2809 (3) | 0.1198 (13) | |
H46A | −0.0055 | 0.7620 | 0.3421 | 0.144* | |
C51 | 0.1147 (3) | 0.2565 (3) | 0.4182 (2) | 0.0771 (9) | |
C52 | 0.2475 (4) | 0.2475 (3) | 0.4081 (2) | 0.1078 (11) | |
H52A | 0.2845 | 0.3119 | 0.3613 | 0.129* | |
C53 | 0.3281 (4) | 0.1443 (4) | 0.4662 (3) | 0.1188 (13) | |
H53A | 0.4180 | 0.1392 | 0.4567 | 0.143* | |
C54 | 0.2772 (4) | 0.0514 (4) | 0.5363 (3) | 0.1106 (13) | |
H54A | 0.3317 | −0.0166 | 0.5757 | 0.133* | |
C55 | 0.1470 (4) | 0.0576 (4) | 0.5488 (2) | 0.1218 (13) | |
H55A | 0.1114 | −0.0065 | 0.5967 | 0.146* | |
C56 | 0.0660 (3) | 0.1597 (4) | 0.4901 (3) | 0.1075 (11) | |
H56A | −0.0237 | 0.1629 | 0.4996 | 0.129* | |
C61 | −0.1402 (3) | 0.3895 (3) | 0.4025 (2) | 0.0812 (9) | |
C62 | −0.1714 (4) | 0.4566 (3) | 0.4633 (3) | 0.1097 (12) | |
H62A | −0.1135 | 0.5075 | 0.4684 | 0.132* | |
C63 | −0.2851 (6) | 0.4500 (5) | 0.5158 (3) | 0.1447 (17) | |
H63A | −0.3040 | 0.4979 | 0.5547 | 0.174* | |
C64 | −0.3709 (5) | 0.3748 (5) | 0.5122 (3) | 0.1387 (17) | |
H64A | −0.4465 | 0.3680 | 0.5498 | 0.166* | |
C65 | −0.3436 (4) | 0.3094 (4) | 0.4521 (4) | 0.1334 (15) | |
H65A | −0.4023 | 0.2590 | 0.4475 | 0.160* | |
C66 | −0.2304 (4) | 0.3168 (3) | 0.3981 (3) | 0.1103 (12) | |
H66A | −0.2143 | 0.2714 | 0.3574 | 0.132* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.1258 (8) | 0.0651 (6) | 0.0755 (6) | 0.0018 (5) | −0.0209 (5) | −0.0278 (5) |
P2 | 0.0892 (6) | 0.0701 (6) | 0.0896 (6) | −0.0043 (5) | −0.0158 (5) | −0.0297 (5) |
N1 | 0.121 (2) | 0.0823 (19) | 0.0713 (17) | −0.0030 (17) | −0.0139 (16) | −0.0411 (16) |
O1 | 0.1241 (17) | 0.0707 (14) | 0.0902 (15) | 0.0135 (13) | −0.0392 (13) | −0.0399 (12) |
O2 | 0.208 (3) | 0.145 (3) | 0.133 (2) | −0.053 (2) | −0.036 (2) | −0.054 (2) |
O3 | 0.240 (8) | 0.112 (5) | 0.168 (7) | 0.047 (7) | −0.097 (7) | −0.040 (5) |
O3' | 0.252 (10) | 0.164 (7) | 0.121 (6) | −0.106 (7) | −0.081 (6) | 0.020 (6) |
C1 | 0.125 (3) | 0.095 (3) | 0.083 (2) | −0.018 (2) | 0.001 (2) | −0.040 (2) |
C2 | 0.127 (3) | 0.100 (3) | 0.109 (3) | −0.014 (2) | −0.027 (2) | −0.038 (2) |
C3 | 0.204 (5) | 0.077 (3) | 0.108 (4) | −0.018 (4) | −0.064 (4) | −0.029 (3) |
C4 | 0.250 (5) | 0.299 (6) | 0.101 (3) | −0.130 (5) | −0.040 (3) | −0.057 (4) |
C11 | 0.101 (2) | 0.061 (2) | 0.074 (2) | −0.0036 (18) | −0.0150 (18) | −0.0238 (17) |
C12 | 0.091 (2) | 0.067 (2) | 0.071 (2) | −0.0042 (18) | −0.0142 (18) | −0.0248 (18) |
C13 | 0.096 (2) | 0.070 (2) | 0.074 (2) | −0.0055 (19) | −0.0109 (18) | −0.0286 (19) |
C14 | 0.126 (3) | 0.084 (2) | 0.078 (2) | −0.003 (2) | −0.025 (2) | −0.033 (2) |
C15 | 0.144 (3) | 0.087 (3) | 0.085 (3) | 0.008 (2) | −0.039 (2) | −0.026 (2) |
C16 | 0.130 (3) | 0.076 (2) | 0.090 (2) | 0.013 (2) | −0.032 (2) | −0.035 (2) |
C21 | 0.077 (2) | 0.064 (2) | 0.082 (2) | −0.0027 (17) | −0.0089 (17) | −0.0265 (18) |
C22 | 0.084 (2) | 0.062 (2) | 0.088 (2) | −0.0079 (17) | −0.0045 (18) | −0.0379 (19) |
C23 | 0.089 (2) | 0.071 (2) | 0.081 (2) | −0.0113 (18) | −0.0017 (18) | −0.034 (2) |
C24 | 0.106 (3) | 0.088 (3) | 0.095 (3) | −0.008 (2) | −0.006 (2) | −0.052 (2) |
C25 | 0.110 (3) | 0.083 (2) | 0.121 (3) | 0.007 (2) | −0.014 (2) | −0.058 (2) |
C26 | 0.099 (2) | 0.072 (2) | 0.105 (3) | −0.0014 (19) | −0.014 (2) | −0.037 (2) |
C31 | 0.107 (3) | 0.069 (2) | 0.071 (2) | −0.004 (2) | −0.012 (2) | −0.0276 (19) |
C32 | 0.121 (3) | 0.092 (3) | 0.116 (3) | −0.016 (3) | −0.009 (3) | −0.051 (2) |
C33 | 0.105 (3) | 0.131 (4) | 0.127 (3) | −0.002 (3) | −0.009 (2) | −0.069 (3) |
C34 | 0.133 (4) | 0.102 (3) | 0.087 (3) | 0.027 (3) | −0.030 (3) | −0.044 (3) |
C35 | 0.144 (3) | 0.068 (3) | 0.083 (3) | 0.005 (3) | −0.013 (2) | −0.022 (2) |
C36 | 0.117 (3) | 0.073 (2) | 0.080 (2) | 0.004 (2) | −0.0046 (19) | −0.028 (2) |
C41 | 0.107 (3) | 0.064 (2) | 0.088 (2) | 0.0126 (19) | −0.034 (2) | −0.033 (2) |
C42 | 0.111 (3) | 0.095 (3) | 0.106 (3) | 0.000 (2) | −0.017 (3) | −0.052 (3) |
C43 | 0.109 (3) | 0.102 (3) | 0.154 (4) | −0.001 (3) | −0.003 (3) | −0.062 (3) |
C44 | 0.111 (4) | 0.102 (4) | 0.208 (5) | 0.010 (3) | −0.050 (4) | −0.054 (4) |
C45 | 0.156 (5) | 0.121 (4) | 0.155 (5) | −0.018 (3) | −0.073 (4) | −0.019 (4) |
C46 | 0.147 (4) | 0.099 (3) | 0.109 (3) | −0.009 (3) | −0.047 (3) | −0.025 (2) |
C51 | 0.071 (2) | 0.077 (2) | 0.083 (2) | −0.0027 (18) | −0.0124 (18) | −0.031 (2) |
C52 | 0.089 (3) | 0.098 (3) | 0.129 (3) | −0.008 (2) | −0.012 (2) | −0.031 (2) |
C53 | 0.079 (3) | 0.123 (4) | 0.147 (4) | 0.008 (3) | −0.025 (3) | −0.044 (3) |
C54 | 0.108 (4) | 0.109 (3) | 0.117 (3) | 0.019 (3) | −0.042 (3) | −0.048 (3) |
C55 | 0.107 (3) | 0.107 (3) | 0.119 (3) | 0.007 (3) | −0.028 (3) | −0.006 (2) |
C56 | 0.087 (3) | 0.102 (3) | 0.114 (3) | 0.002 (2) | −0.022 (2) | −0.017 (2) |
C61 | 0.083 (2) | 0.071 (2) | 0.084 (2) | 0.0079 (19) | −0.0173 (19) | −0.0251 (19) |
C62 | 0.120 (3) | 0.112 (3) | 0.102 (3) | −0.004 (2) | −0.003 (2) | −0.050 (3) |
C63 | 0.158 (5) | 0.144 (5) | 0.125 (4) | 0.001 (4) | 0.035 (4) | −0.058 (3) |
C64 | 0.114 (4) | 0.122 (4) | 0.136 (4) | 0.019 (3) | 0.022 (3) | −0.014 (3) |
C65 | 0.093 (3) | 0.129 (4) | 0.176 (4) | −0.010 (3) | 0.008 (3) | −0.056 (3) |
C66 | 0.086 (3) | 0.122 (3) | 0.134 (3) | −0.006 (3) | −0.003 (3) | −0.063 (3) |
P1—C41 | 1.834 (4) | C31—C36 | 1.372 (4) |
P1—C31 | 1.835 (3) | C31—C32 | 1.381 (4) |
P1—C11 | 1.836 (3) | C32—C33 | 1.389 (4) |
P1—P2 | 4.2346 (13) | C32—H32A | 0.9300 |
P2—C61 | 1.819 (3) | C33—C34 | 1.358 (4) |
P2—C21 | 1.833 (3) | C33—H33A | 0.9300 |
P2—C51 | 1.834 (3) | C34—C35 | 1.372 (4) |
N1—C13 | 1.398 (3) | C34—H34A | 0.9300 |
N1—C23 | 1.401 (3) | C35—C36 | 1.396 (4) |
N1—C1 | 1.456 (3) | C35—H35A | 0.9300 |
O1—C12 | 1.383 (3) | C36—H36A | 0.9300 |
O1—C22 | 1.391 (3) | C41—C46 | 1.384 (4) |
O2—C3 | 1.200 (4) | C41—C42 | 1.385 (4) |
O2—C4 | 1.476 (4) | C42—C43 | 1.381 (4) |
O3—C3 | 1.236 (6) | C42—H42A | 0.9300 |
O3—O3' | 1.407 (9) | C43—C44 | 1.370 (5) |
O3'—C3 | 1.277 (7) | C43—H43A | 0.9300 |
C1—C2 | 1.516 (4) | C44—C45 | 1.362 (5) |
C1—H1A | 0.9700 | C44—H44A | 0.9300 |
C1—H1B | 0.9700 | C45—C46 | 1.381 (5) |
C2—C3 | 1.480 (4) | C45—H45A | 0.9300 |
C2—H2A | 0.9700 | C46—H46A | 0.9300 |
C2—H2B | 0.9700 | C51—C52 | 1.370 (4) |
C4—H4A | 0.9600 | C51—C56 | 1.376 (4) |
C4—H4B | 0.9600 | C52—C53 | 1.389 (4) |
C4—H4C | 0.9600 | C52—H52A | 0.9300 |
C11—C12 | 1.387 (3) | C53—C54 | 1.349 (4) |
C11—C16 | 1.395 (3) | C53—H53A | 0.9300 |
C12—C13 | 1.393 (3) | C54—C55 | 1.347 (4) |
C13—C14 | 1.383 (3) | C54—H54A | 0.9300 |
C14—C15 | 1.382 (3) | C55—C56 | 1.388 (4) |
C14—H14A | 0.9300 | C55—H55A | 0.9300 |
C15—C16 | 1.378 (3) | C56—H56A | 0.9300 |
C15—H15A | 0.9300 | C61—C66 | 1.374 (4) |
C16—H16A | 0.9300 | C61—C62 | 1.386 (4) |
C21—C22 | 1.380 (3) | C62—C63 | 1.368 (5) |
C21—C26 | 1.397 (3) | C62—H62A | 0.9300 |
C22—C23 | 1.394 (3) | C63—C64 | 1.355 (5) |
C23—C24 | 1.389 (3) | C63—H63A | 0.9300 |
C24—C25 | 1.379 (4) | C64—C65 | 1.360 (5) |
C24—H24A | 0.9300 | C64—H64A | 0.9300 |
C25—C26 | 1.375 (3) | C65—C66 | 1.374 (5) |
C25—H25A | 0.9300 | C65—H65A | 0.9300 |
C26—H26A | 0.9300 | C66—H66A | 0.9300 |
C41—P1—C31 | 103.40 (16) | C25—C26—C21 | 120.4 (3) |
C41—P1—C11 | 101.59 (15) | C25—C26—H26A | 119.8 |
C31—P1—C11 | 100.90 (13) | C21—C26—H26A | 119.8 |
C41—P1—P2 | 79.67 (9) | C36—C31—C32 | 117.6 (3) |
C31—P1—P2 | 160.90 (10) | C36—C31—P1 | 125.3 (3) |
C11—P1—P2 | 96.84 (9) | C32—C31—P1 | 117.0 (3) |
C61—P2—C21 | 100.97 (14) | C31—C32—C33 | 122.1 (4) |
C61—P2—C51 | 100.55 (15) | C31—C32—H32A | 119.0 |
C21—P2—C51 | 101.69 (13) | C33—C32—H32A | 119.0 |
C61—P2—P1 | 71.97 (9) | C34—C33—C32 | 119.2 (4) |
C21—P2—P1 | 96.74 (9) | C34—C33—H33A | 120.4 |
C51—P2—P1 | 161.18 (9) | C32—C33—H33A | 120.4 |
C13—N1—C23 | 119.2 (2) | C33—C34—C35 | 120.4 (4) |
C13—N1—C1 | 119.3 (2) | C33—C34—H34A | 119.8 |
C23—N1—C1 | 121.0 (2) | C35—C34—H34A | 119.8 |
C12—O1—C22 | 119.0 (2) | C34—C35—C36 | 119.9 (4) |
C3—O2—C4 | 115.3 (3) | C34—C35—H35A | 120.1 |
C3—O3—O3' | 57.4 (5) | C36—C35—H35A | 120.1 |
C3—O3'—O3 | 54.6 (4) | C31—C36—C35 | 120.9 (3) |
N1—C1—C2 | 113.6 (3) | C31—C36—H36A | 119.5 |
N1—C1—H1A | 108.8 | C35—C36—H36A | 119.5 |
C2—C1—H1A | 108.8 | C46—C41—C42 | 117.5 (4) |
N1—C1—H1B | 108.8 | C46—C41—P1 | 117.0 (4) |
C2—C1—H1B | 108.8 | C42—C41—P1 | 125.5 (3) |
H1A—C1—H1B | 107.7 | C43—C42—C41 | 121.1 (3) |
C3—C2—C1 | 111.6 (4) | C43—C42—H42A | 119.4 |
C3—C2—H2A | 109.3 | C41—C42—H42A | 119.4 |
C1—C2—H2A | 109.3 | C44—C43—C42 | 120.7 (4) |
C3—C2—H2B | 109.3 | C44—C43—H43A | 119.7 |
C1—C2—H2B | 109.3 | C42—C43—H43A | 119.7 |
H2A—C2—H2B | 108.0 | C45—C44—C43 | 118.6 (5) |
O2—C3—O3 | 108.5 (7) | C45—C44—H44A | 120.7 |
O2—C3—O3' | 113.6 (6) | C43—C44—H44A | 120.7 |
O3—C3—O3' | 68.1 (5) | C44—C45—C46 | 121.4 (5) |
O2—C3—C2 | 117.2 (4) | C44—C45—H45A | 119.3 |
O3—C3—C2 | 120.8 (6) | C46—C45—H45A | 119.3 |
O3'—C3—C2 | 119.2 (6) | C45—C46—C41 | 120.6 (4) |
O2—C4—H4A | 109.5 | C45—C46—H46A | 119.7 |
O2—C4—H4B | 109.5 | C41—C46—H46A | 119.7 |
H4A—C4—H4B | 109.5 | C52—C51—C56 | 116.5 (3) |
O2—C4—H4C | 109.5 | C52—C51—P2 | 117.9 (3) |
H4A—C4—H4C | 109.5 | C56—C51—P2 | 125.5 (3) |
H4B—C4—H4C | 109.5 | C51—C52—C53 | 121.3 (4) |
C12—C11—C16 | 117.0 (2) | C51—C52—H52A | 119.3 |
C12—C11—P1 | 117.6 (2) | C53—C52—H52A | 119.3 |
C16—C11—P1 | 125.3 (2) | C54—C53—C52 | 120.6 (4) |
O1—C12—C11 | 115.4 (2) | C54—C53—H53A | 119.7 |
O1—C12—C13 | 120.8 (2) | C52—C53—H53A | 119.7 |
C11—C12—C13 | 123.7 (3) | C55—C54—C53 | 119.6 (4) |
C14—C13—C12 | 117.2 (3) | C55—C54—H54A | 120.2 |
C14—C13—N1 | 123.4 (3) | C53—C54—H54A | 120.2 |
C12—C13—N1 | 119.4 (3) | C54—C55—C56 | 120.0 (4) |
C15—C14—C13 | 120.5 (3) | C54—C55—H55A | 120.0 |
C15—C14—H14A | 119.7 | C56—C55—H55A | 120.0 |
C13—C14—H14A | 119.7 | C51—C56—C55 | 121.9 (3) |
C16—C15—C14 | 121.1 (3) | C51—C56—H56A | 119.0 |
C16—C15—H15A | 119.5 | C55—C56—H56A | 119.0 |
C14—C15—H15A | 119.5 | C66—C61—C62 | 116.1 (3) |
C15—C16—C11 | 120.4 (3) | C66—C61—P2 | 125.7 (3) |
C15—C16—H16A | 119.8 | C62—C61—P2 | 118.1 (3) |
C11—C16—H16A | 119.8 | C63—C62—C61 | 121.7 (4) |
C22—C21—C26 | 116.9 (3) | C63—C62—H62A | 119.1 |
C22—C21—P2 | 117.6 (2) | C61—C62—H62A | 119.1 |
C26—C21—P2 | 125.5 (2) | C64—C63—C62 | 121.1 (5) |
C21—C22—O1 | 115.8 (2) | C64—C63—H63A | 119.5 |
C21—C22—C23 | 124.0 (3) | C62—C63—H63A | 119.5 |
O1—C22—C23 | 120.2 (3) | C63—C64—C65 | 118.4 (5) |
C24—C23—C22 | 117.1 (3) | C63—C64—H64A | 120.8 |
C24—C23—N1 | 123.1 (3) | C65—C64—H64A | 120.8 |
C22—C23—N1 | 119.7 (3) | C64—C65—C66 | 120.9 (4) |
C25—C24—C23 | 120.2 (3) | C64—C65—H65A | 119.6 |
C25—C24—H24A | 119.9 | C66—C65—H65A | 119.6 |
C23—C24—H24A | 119.9 | C65—C66—C61 | 121.8 (3) |
C26—C25—C24 | 121.3 (3) | C65—C66—H66A | 119.1 |
C26—C25—H25A | 119.3 | C61—C66—H66A | 119.1 |
C24—C25—H25A | 119.3 | ||
C41—P1—P2—C61 | 156.93 (16) | C1—N1—C23—C24 | 0.4 (5) |
C31—P1—P2—C61 | 55.8 (4) | C13—N1—C23—C22 | −9.7 (4) |
C11—P1—P2—C61 | −102.47 (15) | C1—N1—C23—C22 | 178.3 (3) |
C41—P1—P2—C21 | −103.69 (15) | C22—C23—C24—C25 | −1.0 (5) |
C31—P1—P2—C21 | 155.2 (4) | N1—C23—C24—C25 | 177.0 (3) |
C11—P1—P2—C21 | −3.09 (14) | C23—C24—C25—C26 | 1.7 (5) |
C41—P1—P2—C51 | 87.9 (4) | C24—C25—C26—C21 | −0.5 (5) |
C31—P1—P2—C51 | −13.3 (6) | C22—C21—C26—C25 | −1.3 (4) |
C11—P1—P2—C51 | −171.5 (4) | P2—C21—C26—C25 | −178.1 (2) |
C13—N1—C1—C2 | −85.0 (3) | C41—P1—C31—C36 | 11.3 (3) |
C23—N1—C1—C2 | 86.9 (3) | C11—P1—C31—C36 | −93.5 (3) |
N1—C1—C2—C3 | 145.9 (3) | P2—P1—C31—C36 | 108.5 (4) |
C4—O2—C3—O3 | 36.1 (11) | C41—P1—C31—C32 | −165.9 (2) |
C4—O2—C3—O3' | −37.4 (11) | C11—P1—C31—C32 | 89.3 (2) |
C4—O2—C3—C2 | 177.3 (4) | P2—P1—C31—C32 | −68.7 (5) |
O3'—O3—C3—O2 | −108.7 (8) | C36—C31—C32—C33 | 1.0 (4) |
O3'—O3—C3—C2 | 111.8 (8) | P1—C31—C32—C33 | 178.4 (2) |
O3—O3'—C3—O2 | 101.4 (9) | C31—C32—C33—C34 | −1.6 (5) |
O3—O3'—C3—C2 | −114.0 (7) | C32—C33—C34—C35 | 1.0 (5) |
C1—C2—C3—O2 | 130.4 (6) | C33—C34—C35—C36 | 0.1 (5) |
C1—C2—C3—O3 | −93.4 (11) | C32—C31—C36—C35 | 0.2 (4) |
C1—C2—C3—O3' | −12.9 (11) | P1—C31—C36—C35 | −177.0 (2) |
C41—P1—C11—C12 | 80.1 (3) | C34—C35—C36—C31 | −0.8 (4) |
C31—P1—C11—C12 | −173.6 (3) | C31—P1—C41—C46 | 91.8 (2) |
P2—P1—C11—C12 | −0.7 (2) | C11—P1—C41—C46 | −163.9 (2) |
C41—P1—C11—C16 | −104.4 (3) | P2—P1—C41—C46 | −68.9 (2) |
C31—P1—C11—C16 | 1.9 (3) | C31—P1—C41—C42 | −88.9 (3) |
P2—P1—C11—C16 | 174.8 (3) | C11—P1—C41—C42 | 15.4 (3) |
C22—O1—C12—C11 | 170.8 (3) | P2—P1—C41—C42 | 110.3 (3) |
C22—O1—C12—C13 | −11.1 (4) | C46—C41—C42—C43 | 0.1 (5) |
C16—C11—C12—O1 | 179.0 (3) | P1—C41—C42—C43 | −179.1 (2) |
P1—C11—C12—O1 | −5.1 (4) | C41—C42—C43—C44 | −0.7 (5) |
C16—C11—C12—C13 | 1.0 (5) | C42—C43—C44—C45 | 0.5 (6) |
P1—C11—C12—C13 | 176.9 (2) | C43—C44—C45—C46 | 0.3 (7) |
O1—C12—C13—C14 | −179.9 (3) | C44—C45—C46—C41 | −0.9 (7) |
C11—C12—C13—C14 | −2.0 (5) | C42—C41—C46—C45 | 0.6 (5) |
O1—C12—C13—N1 | −0.1 (4) | P1—C41—C46—C45 | 180.0 (3) |
C11—C12—C13—N1 | 177.9 (3) | C61—P2—C51—C52 | −163.4 (2) |
C23—N1—C13—C14 | −169.7 (3) | C21—P2—C51—C52 | 93.0 (2) |
C1—N1—C13—C14 | 2.5 (5) | P1—P2—C51—C52 | −98.8 (4) |
C23—N1—C13—C12 | 10.5 (4) | C61—P2—C51—C56 | 13.0 (3) |
C1—N1—C13—C12 | −177.4 (3) | C21—P2—C51—C56 | −90.7 (3) |
C12—C13—C14—C15 | 1.9 (5) | P1—P2—C51—C56 | 77.6 (5) |
N1—C13—C14—C15 | −178.0 (3) | C56—C51—C52—C53 | 1.5 (5) |
C13—C14—C15—C16 | −0.8 (5) | P2—C51—C52—C53 | 178.2 (2) |
C14—C15—C16—C11 | −0.2 (5) | C51—C52—C53—C54 | −1.9 (5) |
C12—C11—C16—C15 | 0.2 (5) | C52—C53—C54—C55 | 1.3 (6) |
P1—C11—C16—C15 | −175.4 (3) | C53—C54—C55—C56 | −0.5 (6) |
C61—P2—C21—C22 | 78.0 (3) | C52—C51—C56—C55 | −0.6 (5) |
C51—P2—C21—C22 | −178.7 (2) | P2—C51—C56—C55 | −177.1 (3) |
P1—P2—C21—C22 | 5.1 (2) | C54—C55—C56—C51 | 0.1 (5) |
C61—P2—C21—C26 | −105.2 (3) | C21—P2—C61—C66 | 21.5 (3) |
C51—P2—C21—C26 | −1.9 (3) | C51—P2—C61—C66 | −82.7 (3) |
P1—P2—C21—C26 | −178.1 (3) | P1—P2—C61—C66 | 115.1 (3) |
C26—C21—C22—O1 | −175.5 (2) | C21—P2—C61—C62 | −161.4 (2) |
P2—C21—C22—O1 | 1.5 (4) | C51—P2—C61—C62 | 94.4 (2) |
C26—C21—C22—C23 | 2.1 (4) | P1—P2—C61—C62 | −67.8 (2) |
P2—C21—C22—C23 | 179.2 (2) | C66—C61—C62—C63 | 0.3 (5) |
C12—O1—C22—C21 | −170.4 (3) | P2—C61—C62—C63 | −177.1 (3) |
C12—O1—C22—C23 | 11.9 (4) | C61—C62—C63—C64 | 1.6 (7) |
C21—C22—C23—C24 | −1.0 (4) | C62—C63—C64—C65 | −2.5 (7) |
O1—C22—C23—C24 | 176.5 (3) | C63—C64—C65—C66 | 1.6 (7) |
C21—C22—C23—N1 | −179.0 (3) | C64—C65—C66—C61 | 0.3 (6) |
O1—C22—C23—N1 | −1.5 (4) | C62—C61—C66—C65 | −1.2 (5) |
C13—N1—C23—C24 | 172.4 (3) | P2—C61—C66—C65 | 176.0 (3) |