Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020320/hb2073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020320/hb2073Isup2.hkl |
CCDC reference: 614864
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).
C40H32N2O2P2 | Z = 2 |
Mr = 634.62 | F(000) = 664 |
Triclinic, P1 | Dx = 1.267 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3740 (7) Å | Cell parameters from 26936 reflections |
b = 12.5567 (8) Å | θ = 3.0–27.6° |
c = 13.1164 (12) Å | µ = 0.17 mm−1 |
α = 115.644 (4)° | T = 291 K |
β = 97.432 (5)° | Block, colourless |
γ = 92.527 (4)° | 0.50 × 0.30 × 0.16 mm |
V = 1664.1 (2) Å3 |
Nonius KappaCCD diffractometer | 3761 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.6°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −14→14 |
517 frames via ω–rotation (Δω=1°) and two times 10 s per frame (five sets at different κ–angles) scans | k = −16→16 |
26936 measured reflections | l = −17→16 |
7593 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0298P)2] where P = (Fo2 + 2Fc2)/3 |
7593 reflections | (Δ/σ)max = 0.002 |
424 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Experimental. 13C NMR (125 MHz, CDCl3): δ 43.4 (CH2), 116.3 (CH2), 123.8 (CH), 124.8 (CH), 127.4 (C), 128.4 (m, CH), 129.0 (C), 130.6 (CH), 134.0 (m, CH), 134.5 (CH), 136.3 (C), 153.1 (C), 154.4 (C); MS (FAB+ LR): m/z (%) = 635.5 (M+H)+, (30), 551 (10); exact mass (FAB+ HR): 634.1942 (M)+, (90) (calculated for C40H32N2O2P2 634.1939). 1H NMR (500 MHz, CDCl3): δ 3.92 (t, 2H, J = 5.5), 5.15 (d v. d, 2H, J = 25.2 and 17.2), 5.40 (t, 2H, J = 5.5), 5.88, (m, 1H), 6.51 (d, 2H, J = 7.7), 6.99 (t, 2H, J = 8.0), 7.17–7.32 (bs, 20H), 7.51 (d, 2H, J = 8.0); 13C NMR (125 MHz, CDCl3): δ [p.p.m.] = 43.4 (CH2), 116.3 (CH2), 123.8 (CH), 124.8 (CH), 127.4 (C), 128.4 (m, CH), 129.0 (C), 130.6 (CH), 134.0 (m, CH), 134.5 (CH), 136.3 (C), 153.1 (C), 154.4 (C); 31P NMR (81 MHz, CDCl3): δ [p.p.m.] = -17.3; IR (KBr plate): ν [cm-1] 737 (w), 908 (w), 1025 (m), 1093 (m), 1227 (m), 1259 (w), 1321 (m), 1414 (w), 1462 (m), 1504 (m), 1681 (m), 2925 (s), 2962 (s), 3055 (s), 3070 (s). MS (FAB+ LR): m/z (%) = 635.5 (M+H)+, (30), 551 (10); exact mass (FAB+ HR): 634.1942 (M)+, (90), (calcd. for C40H32O2N2P2 634.1939). |
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 | 0.74790 (4) | 0.31610 (4) | 0.04621 (4) | 0.05418 (15) | |
P2 | 0.85034 (5) | 0.15713 (4) | 0.26608 (4) | 0.05601 (16) | |
O1 | 0.58689 (12) | 0.69101 (13) | 0.49767 (12) | 0.0793 (4) | |
O2 | 0.74847 (9) | 0.37688 (9) | 0.28939 (9) | 0.0478 (3) | |
N1 | 0.63292 (14) | 0.60546 (15) | 0.61469 (14) | 0.0721 (5) | |
H1A | 0.6834 | 0.5672 | 0.6362 | 0.086* | |
N2 | 0.74956 (12) | 0.58864 (12) | 0.47533 (11) | 0.0489 (4) | |
C1' | 0.5303 (5) | 0.7761 (11) | 0.8720 (6) | 0.235 (6) | 0.50 |
H1'1 | 0.5758 | 0.8413 | 0.9328 | 0.282* | 0.50 |
H1'2 | 0.4710 | 0.7328 | 0.8857 | 0.282* | 0.50 |
C1 | 0.6101 (11) | 0.8232 (7) | 0.8289 (8) | 0.246 (7) | 0.50 |
H1B | 0.6103 | 0.8587 | 0.9076 | 0.295* | 0.50 |
H1C | 0.6637 | 0.8540 | 0.7980 | 0.295* | 0.50 |
C2 | 0.5483 (3) | 0.7472 (4) | 0.7741 (3) | 0.1489 (15) | |
H2 | 0.5817 | 0.8107 | 0.7648 | 0.179* | |
C3 | 0.53038 (18) | 0.6404 (2) | 0.67228 (18) | 0.0814 (7) | |
H3A | 0.4670 | 0.6472 | 0.6190 | 0.098* | |
H3B | 0.5026 | 0.5770 | 0.6897 | 0.098* | |
C4 | 0.65052 (17) | 0.63184 (16) | 0.52826 (16) | 0.0570 (5) | |
C5 | 0.75369 (14) | 0.58856 (15) | 0.36685 (14) | 0.0477 (4) | |
C6 | 0.76249 (16) | 0.69084 (16) | 0.35164 (16) | 0.0586 (5) | |
H6A | 0.7652 | 0.7649 | 0.4137 | 0.070* | |
C7 | 0.76724 (17) | 0.68221 (16) | 0.24415 (17) | 0.0664 (6) | |
H7A | 0.7731 | 0.7509 | 0.2338 | 0.080* | |
C8 | 0.76345 (16) | 0.57207 (16) | 0.15095 (16) | 0.0623 (5) | |
H8A | 0.7658 | 0.5682 | 0.0788 | 0.075* | |
C9 | 0.75615 (14) | 0.46737 (15) | 0.16304 (14) | 0.0480 (4) | |
C10 | 0.75251 (14) | 0.47945 (14) | 0.27323 (14) | 0.0449 (4) | |
C11 | 0.80958 (14) | 0.39083 (15) | 0.39440 (14) | 0.0435 (4) | |
C12 | 0.86533 (14) | 0.29690 (14) | 0.39785 (14) | 0.0446 (4) | |
C13 | 0.93052 (15) | 0.31651 (15) | 0.50367 (15) | 0.0520 (5) | |
H13A | 0.9696 | 0.2555 | 0.5098 | 0.062* | |
C14 | 0.93794 (15) | 0.42470 (16) | 0.59925 (15) | 0.0539 (5) | |
H14A | 0.9823 | 0.4357 | 0.6685 | 0.065* | |
C15 | 0.88025 (15) | 0.51616 (15) | 0.59286 (14) | 0.0503 (5) | |
H15A | 0.8868 | 0.5892 | 0.6571 | 0.060* | |
C16 | 0.81230 (14) | 0.49899 (14) | 0.49011 (14) | 0.0457 (4) | |
C21 | 0.71072 (16) | 0.34200 (14) | −0.08080 (15) | 0.0507 (5) | |
C22 | 0.77950 (17) | 0.31156 (16) | −0.16603 (16) | 0.0597 (5) | |
H22A | 0.8540 | 0.2868 | −0.1552 | 0.072* | |
C23 | 0.7393 (2) | 0.31719 (17) | −0.26817 (17) | 0.0705 (6) | |
H23A | 0.7870 | 0.2956 | −0.3250 | 0.085* | |
C24 | 0.6315 (2) | 0.35379 (18) | −0.28574 (19) | 0.0764 (6) | |
H24A | 0.6049 | 0.3569 | −0.3544 | 0.092* | |
C25 | 0.5618 (2) | 0.3862 (2) | −0.2015 (2) | 0.0804 (6) | |
H25A | 0.4884 | 0.4129 | −0.2122 | 0.097* | |
C26 | 0.60096 (18) | 0.37933 (17) | −0.10046 (18) | 0.0688 (6) | |
H26A | 0.5524 | 0.4003 | −0.0444 | 0.083* | |
C31 | 0.90558 (17) | 0.29391 (16) | 0.04548 (14) | 0.0541 (5) | |
C32 | 0.9338 (2) | 0.17823 (18) | 0.00049 (17) | 0.0751 (6) | |
H32A | 0.8734 | 0.1157 | −0.0255 | 0.090* | |
C33 | 1.0508 (3) | 0.1543 (2) | −0.0064 (2) | 0.0948 (8) | |
H33A | 1.0683 | 0.0759 | −0.0387 | 0.114* | |
C34 | 1.1410 (2) | 0.2458 (3) | 0.0345 (2) | 0.0972 (8) | |
H34A | 1.2198 | 0.2295 | 0.0315 | 0.117* | |
C35 | 1.1153 (2) | 0.3610 (2) | 0.07956 (18) | 0.0830 (7) | |
H35A | 1.1763 | 0.4231 | 0.1068 | 0.100* | |
C36 | 0.99838 (18) | 0.38446 (18) | 0.08446 (15) | 0.0649 (5) | |
H36A | 0.9814 | 0.4630 | 0.1146 | 0.078* | |
C41 | 0.71800 (16) | 0.07943 (15) | 0.27976 (17) | 0.0608 (5) | |
C42 | 0.6680 (2) | 0.1113 (2) | 0.3768 (2) | 0.0850 (7) | |
H42A | 0.7028 | 0.1779 | 0.4431 | 0.102* | |
C43 | 0.5670 (2) | 0.0473 (3) | 0.3793 (3) | 0.1111 (9) | |
H43A | 0.5347 | 0.0717 | 0.4464 | 0.133* | |
C44 | 0.5153 (2) | −0.0504 (3) | 0.2846 (4) | 0.1256 (11) | |
H44A | 0.4488 | −0.0949 | 0.2865 | 0.151* | |
C45 | 0.5615 (3) | −0.0826 (2) | 0.1867 (3) | 0.1462 (13) | |
H45A | 0.5258 | −0.1493 | 0.1209 | 0.175* | |
C46 | 0.6612 (2) | −0.0178 (2) | 0.1830 (2) | 0.1092 (9) | |
H46A | 0.6902 | −0.0403 | 0.1143 | 0.131* | |
C51 | 0.97135 (18) | 0.08402 (16) | 0.30581 (15) | 0.0575 (5) | |
C52 | 0.9585 (2) | −0.00383 (19) | 0.34004 (19) | 0.0806 (6) | |
H52A | 0.8830 | −0.0297 | 0.3460 | 0.097* | |
C53 | 1.0564 (3) | −0.0548 (2) | 0.3660 (2) | 0.1073 (9) | |
H53A | 1.0458 | −0.1146 | 0.3888 | 0.129* | |
C54 | 1.1681 (3) | −0.0182 (3) | 0.3584 (2) | 0.1053 (9) | |
H54A | 1.2335 | −0.0521 | 0.3769 | 0.126* | |
C55 | 1.1833 (2) | 0.0680 (2) | 0.3236 (2) | 0.1007 (9) | |
H55A | 1.2593 | 0.0936 | 0.3184 | 0.121* | |
C56 | 1.0856 (2) | 0.11748 (18) | 0.2960 (2) | 0.0833 (7) | |
H56A | 1.0967 | 0.1749 | 0.2702 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0639 (3) | 0.0514 (3) | 0.0443 (3) | 0.0044 (2) | 0.0113 (2) | 0.0180 (2) |
P2 | 0.0681 (4) | 0.0488 (3) | 0.0497 (3) | 0.0083 (3) | 0.0126 (2) | 0.0196 (2) |
O1 | 0.0754 (10) | 0.1015 (11) | 0.0671 (9) | 0.0438 (9) | 0.0202 (7) | 0.0376 (8) |
O2 | 0.0533 (7) | 0.0452 (7) | 0.0424 (7) | 0.0032 (6) | 0.0054 (6) | 0.0179 (5) |
N1 | 0.0665 (11) | 0.0947 (13) | 0.0671 (11) | 0.0293 (9) | 0.0294 (9) | 0.0401 (10) |
N2 | 0.0503 (9) | 0.0504 (9) | 0.0441 (9) | 0.0148 (7) | 0.0138 (7) | 0.0167 (7) |
C1' | 0.080 (4) | 0.440 (16) | 0.058 (4) | −0.064 (6) | 0.037 (3) | −0.005 (6) |
C1 | 0.425 (19) | 0.121 (6) | 0.130 (8) | 0.031 (9) | −0.121 (11) | 0.045 (5) |
C2 | 0.114 (3) | 0.180 (4) | 0.092 (3) | −0.004 (2) | 0.032 (2) | 0.002 (2) |
C3 | 0.0644 (14) | 0.1052 (18) | 0.0712 (15) | 0.0221 (13) | 0.0295 (12) | 0.0296 (14) |
C4 | 0.0530 (13) | 0.0571 (12) | 0.0478 (12) | 0.0104 (10) | 0.0065 (10) | 0.0114 (10) |
C5 | 0.0486 (11) | 0.0458 (11) | 0.0466 (11) | 0.0109 (8) | 0.0090 (8) | 0.0176 (9) |
C6 | 0.0668 (13) | 0.0478 (11) | 0.0539 (13) | 0.0117 (9) | 0.0099 (10) | 0.0154 (9) |
C7 | 0.0868 (16) | 0.0490 (12) | 0.0671 (14) | 0.0079 (10) | 0.0134 (11) | 0.0287 (11) |
C8 | 0.0784 (14) | 0.0593 (13) | 0.0526 (12) | 0.0100 (11) | 0.0175 (10) | 0.0261 (10) |
C9 | 0.0488 (11) | 0.0488 (11) | 0.0476 (11) | 0.0062 (9) | 0.0121 (8) | 0.0212 (9) |
C10 | 0.0414 (10) | 0.0455 (11) | 0.0483 (11) | 0.0066 (8) | 0.0096 (8) | 0.0203 (9) |
C11 | 0.0382 (10) | 0.0502 (11) | 0.0418 (10) | 0.0004 (8) | 0.0080 (8) | 0.0201 (9) |
C12 | 0.0431 (10) | 0.0466 (10) | 0.0481 (11) | 0.0051 (8) | 0.0119 (8) | 0.0236 (8) |
C13 | 0.0530 (12) | 0.0530 (11) | 0.0559 (12) | 0.0066 (9) | 0.0135 (9) | 0.0284 (10) |
C14 | 0.0520 (12) | 0.0638 (12) | 0.0452 (11) | 0.0038 (10) | 0.0050 (9) | 0.0246 (10) |
C15 | 0.0485 (11) | 0.0526 (11) | 0.0435 (11) | 0.0020 (9) | 0.0098 (9) | 0.0151 (9) |
C16 | 0.0437 (10) | 0.0471 (10) | 0.0455 (11) | 0.0063 (9) | 0.0126 (8) | 0.0182 (9) |
C21 | 0.0513 (12) | 0.0485 (11) | 0.0461 (11) | 0.0031 (9) | 0.0071 (9) | 0.0156 (8) |
C22 | 0.0626 (13) | 0.0664 (13) | 0.0496 (12) | 0.0110 (10) | 0.0097 (10) | 0.0247 (10) |
C23 | 0.0848 (17) | 0.0758 (14) | 0.0534 (13) | 0.0118 (12) | 0.0168 (11) | 0.0292 (11) |
C24 | 0.0922 (18) | 0.0781 (15) | 0.0600 (14) | −0.0006 (13) | −0.0031 (13) | 0.0366 (12) |
C25 | 0.0644 (15) | 0.0955 (17) | 0.0871 (18) | 0.0107 (12) | −0.0016 (13) | 0.0493 (14) |
C26 | 0.0610 (14) | 0.0815 (15) | 0.0696 (15) | 0.0122 (11) | 0.0156 (11) | 0.0370 (12) |
C31 | 0.0690 (13) | 0.0537 (12) | 0.0394 (10) | 0.0163 (11) | 0.0127 (9) | 0.0185 (9) |
C32 | 0.0874 (17) | 0.0649 (14) | 0.0743 (15) | 0.0220 (12) | 0.0219 (12) | 0.0285 (12) |
C33 | 0.114 (2) | 0.0842 (18) | 0.0973 (19) | 0.0523 (18) | 0.0418 (17) | 0.0396 (15) |
C34 | 0.0759 (18) | 0.123 (2) | 0.0905 (19) | 0.0393 (18) | 0.0227 (14) | 0.0401 (18) |
C35 | 0.0708 (17) | 0.0947 (18) | 0.0675 (14) | 0.0100 (14) | 0.0147 (12) | 0.0203 (13) |
C36 | 0.0665 (14) | 0.0650 (13) | 0.0526 (12) | 0.0140 (12) | 0.0116 (10) | 0.0151 (10) |
C41 | 0.0564 (12) | 0.0472 (11) | 0.0675 (13) | 0.0034 (10) | 0.0054 (11) | 0.0167 (10) |
C42 | 0.0789 (17) | 0.0811 (15) | 0.0841 (17) | −0.0202 (13) | 0.0144 (13) | 0.0290 (13) |
C43 | 0.094 (2) | 0.101 (2) | 0.133 (2) | −0.0148 (17) | 0.0379 (17) | 0.045 (2) |
C44 | 0.082 (2) | 0.085 (2) | 0.189 (3) | −0.0146 (17) | 0.042 (2) | 0.039 (2) |
C45 | 0.101 (2) | 0.093 (2) | 0.162 (3) | −0.0365 (18) | 0.028 (2) | −0.017 (2) |
C46 | 0.0797 (18) | 0.0876 (18) | 0.106 (2) | −0.0141 (15) | 0.0195 (14) | −0.0064 (15) |
C51 | 0.0659 (14) | 0.0455 (11) | 0.0544 (12) | 0.0095 (10) | 0.0164 (10) | 0.0141 (9) |
C52 | 0.0868 (17) | 0.0723 (15) | 0.0995 (18) | 0.0266 (13) | 0.0283 (13) | 0.0483 (14) |
C53 | 0.125 (2) | 0.105 (2) | 0.123 (2) | 0.054 (2) | 0.0373 (19) | 0.0707 (18) |
C54 | 0.098 (2) | 0.092 (2) | 0.099 (2) | 0.0429 (18) | 0.0086 (16) | 0.0169 (16) |
C55 | 0.0646 (17) | 0.0725 (17) | 0.135 (2) | 0.0150 (14) | 0.0187 (15) | 0.0166 (16) |
C56 | 0.0754 (17) | 0.0564 (13) | 0.1127 (19) | 0.0106 (12) | 0.0253 (14) | 0.0295 (13) |
P1—C31 | 1.8277 (19) | C21—C22 | 1.375 (2) |
P1—C21 | 1.8326 (18) | C21—C26 | 1.385 (2) |
P1—C9 | 1.8418 (17) | C22—C23 | 1.391 (2) |
P1—P2 | 4.2400 (7) | C22—H22A | 0.9300 |
P2—C41 | 1.828 (2) | C23—C24 | 1.356 (3) |
P2—C51 | 1.8300 (19) | C23—H23A | 0.9300 |
P2—C12 | 1.8353 (17) | C24—C25 | 1.371 (3) |
O1—C4 | 1.211 (2) | C24—H24A | 0.9300 |
O2—C10 | 1.3927 (18) | C25—C26 | 1.382 (3) |
O2—C11 | 1.3941 (18) | C25—H25A | 0.9300 |
N1—C4 | 1.346 (2) | C26—H26A | 0.9300 |
N1—C3 | 1.452 (2) | C31—C32 | 1.382 (2) |
N1—H1A | 0.8600 | C31—C36 | 1.386 (2) |
N2—C4 | 1.406 (2) | C32—C33 | 1.382 (3) |
N2—C16 | 1.428 (2) | C32—H32A | 0.9300 |
N2—C5 | 1.429 (2) | C33—C34 | 1.373 (3) |
C1'—C2 | 1.222 (6) | C33—H33A | 0.9300 |
C1'—H1'1 | 0.9300 | C34—C35 | 1.367 (3) |
C1'—H1'2 | 0.9300 | C34—H34A | 0.9300 |
C1—C2 | 1.067 (9) | C35—C36 | 1.378 (3) |
C1—H1B | 0.9300 | C35—H35A | 0.9300 |
C1—H1C | 0.9300 | C36—H36A | 0.9300 |
C2—C3 | 1.407 (4) | C41—C42 | 1.368 (3) |
C2—H2 | 0.9300 | C41—C46 | 1.377 (3) |
C3—H3A | 0.9700 | C42—C43 | 1.384 (3) |
C3—H3B | 0.9700 | C42—H42A | 0.9300 |
C5—C6 | 1.384 (2) | C43—C44 | 1.350 (4) |
C5—C10 | 1.387 (2) | C43—H43A | 0.9300 |
C6—C7 | 1.375 (2) | C44—C45 | 1.354 (4) |
C6—H6A | 0.9300 | C44—H44A | 0.9300 |
C7—C8 | 1.388 (2) | C45—C46 | 1.384 (4) |
C7—H7A | 0.9300 | C45—H45A | 0.9300 |
C8—C9 | 1.391 (2) | C46—H46A | 0.9300 |
C8—H8A | 0.9300 | C51—C52 | 1.368 (3) |
C9—C10 | 1.393 (2) | C51—C56 | 1.387 (3) |
C11—C12 | 1.378 (2) | C52—C53 | 1.384 (3) |
C11—C16 | 1.390 (2) | C52—H52A | 0.9300 |
C12—C13 | 1.400 (2) | C53—C54 | 1.362 (3) |
C13—C14 | 1.383 (2) | C53—H53A | 0.9300 |
C13—H13A | 0.9300 | C54—C55 | 1.356 (3) |
C14—C15 | 1.376 (2) | C54—H54A | 0.9300 |
C14—H14A | 0.9300 | C55—C56 | 1.380 (3) |
C15—C16 | 1.387 (2) | C55—H55A | 0.9300 |
C15—H15A | 0.9300 | C56—H56A | 0.9300 |
C31—P1—C21 | 101.67 (8) | C15—C16—N2 | 123.61 (15) |
C31—P1—C9 | 101.78 (8) | C11—C16—N2 | 117.74 (15) |
C21—P1—C9 | 101.67 (8) | C22—C21—C26 | 117.35 (17) |
C31—P1—P2 | 71.47 (6) | C22—C21—P1 | 123.15 (14) |
C21—P1—P2 | 163.14 (6) | C26—C21—P1 | 118.93 (15) |
C9—P1—P2 | 94.88 (6) | C21—C22—C23 | 121.01 (18) |
C41—P2—C51 | 102.49 (9) | C21—C22—H22A | 119.5 |
C41—P2—C12 | 100.46 (8) | C23—C22—H22A | 119.5 |
C51—P2—C12 | 100.36 (8) | C24—C23—C22 | 120.7 (2) |
C41—P2—P1 | 109.10 (6) | C24—C23—H23A | 119.7 |
C51—P2—P1 | 141.96 (7) | C22—C23—H23A | 119.7 |
C12—P2—P1 | 94.30 (5) | C23—C24—C25 | 119.5 (2) |
C10—O2—C11 | 114.83 (12) | C23—C24—H24A | 120.3 |
C4—N1—C3 | 121.25 (17) | C25—C24—H24A | 120.3 |
C4—N1—H1A | 119.4 | C24—C25—C26 | 119.9 (2) |
C3—N1—H1A | 119.4 | C24—C25—H25A | 120.0 |
C4—N2—C16 | 123.11 (15) | C26—C25—H25A | 120.0 |
C4—N2—C5 | 117.25 (14) | C25—C26—C21 | 121.5 (2) |
C16—N2—C5 | 113.14 (13) | C25—C26—H26A | 119.2 |
C2—C1'—H1'1 | 120.0 | C21—C26—H26A | 119.2 |
C2—C1'—H1'2 | 120.0 | C32—C31—C36 | 117.75 (18) |
H1'1—C1'—H1'2 | 120.0 | C32—C31—P1 | 117.48 (16) |
C2—C1—H1B | 120.0 | C36—C31—P1 | 124.75 (14) |
C2—C1—H1C | 120.0 | C31—C32—C33 | 120.8 (2) |
H1B—C1—H1C | 120.0 | C31—C32—H32A | 119.6 |
C1—C2—C1' | 73.0 (7) | C33—C32—H32A | 119.6 |
C1—C2—C3 | 144.6 (9) | C34—C33—C32 | 120.1 (2) |
C1'—C2—C3 | 135.0 (8) | C34—C33—H33A | 120.0 |
C1—C2—H2 | 46.9 | C32—C33—H33A | 120.0 |
C1'—C2—H2 | 112.5 | C35—C34—C33 | 120.1 (2) |
C3—C2—H2 | 112.5 | C35—C34—H34A | 119.9 |
C2—C3—N1 | 116.6 (2) | C33—C34—H34A | 119.9 |
C2—C3—H3A | 108.1 | C34—C35—C36 | 119.6 (2) |
N1—C3—H3A | 108.1 | C34—C35—H35A | 120.2 |
C2—C3—H3B | 108.1 | C36—C35—H35A | 120.2 |
N1—C3—H3B | 108.1 | C35—C36—C31 | 121.59 (19) |
H3A—C3—H3B | 107.3 | C35—C36—H36A | 119.2 |
O1—C4—N1 | 122.93 (19) | C31—C36—H36A | 119.2 |
O1—C4—N2 | 120.79 (19) | C42—C41—C46 | 116.8 (2) |
N1—C4—N2 | 116.27 (17) | C42—C41—P2 | 125.85 (15) |
C6—C5—C10 | 118.96 (17) | C46—C41—P2 | 117.31 (18) |
C6—C5—N2 | 123.62 (15) | C41—C42—C43 | 122.0 (2) |
C10—C5—N2 | 117.39 (15) | C41—C42—H42A | 119.0 |
C7—C6—C5 | 119.57 (17) | C43—C42—H42A | 119.0 |
C7—C6—H6A | 120.2 | C44—C43—C42 | 120.3 (3) |
C5—C6—H6A | 120.2 | C44—C43—H43A | 119.9 |
C6—C7—C8 | 120.67 (18) | C42—C43—H43A | 119.9 |
C6—C7—H7A | 119.7 | C43—C44—C45 | 119.0 (3) |
C8—C7—H7A | 119.7 | C43—C44—H44A | 120.5 |
C7—C8—C9 | 121.46 (18) | C45—C44—H44A | 120.5 |
C7—C8—H8A | 119.3 | C44—C45—C46 | 121.0 (3) |
C9—C8—H8A | 119.3 | C44—C45—H45A | 119.5 |
C8—C9—C10 | 116.34 (16) | C46—C45—H45A | 119.5 |
C8—C9—P1 | 125.66 (14) | C41—C46—C45 | 120.9 (3) |
C10—C9—P1 | 117.99 (13) | C41—C46—H46A | 119.6 |
C5—C10—O2 | 118.97 (15) | C45—C46—H46A | 119.6 |
C5—C10—C9 | 122.97 (16) | C52—C51—C56 | 117.15 (19) |
O2—C10—C9 | 118.05 (15) | C52—C51—P2 | 125.79 (17) |
C12—C11—C16 | 123.26 (15) | C56—C51—P2 | 117.01 (16) |
C12—C11—O2 | 118.28 (15) | C51—C52—C53 | 120.9 (2) |
C16—C11—O2 | 118.46 (15) | C51—C52—H52A | 119.5 |
C11—C12—C13 | 116.46 (15) | C53—C52—H52A | 119.5 |
C11—C12—P2 | 118.80 (12) | C54—C53—C52 | 120.7 (3) |
C13—C12—P2 | 124.74 (13) | C54—C53—H53A | 119.6 |
C14—C13—C12 | 121.34 (16) | C52—C53—H53A | 119.6 |
C14—C13—H13A | 119.3 | C55—C54—C53 | 119.6 (3) |
C12—C13—H13A | 119.3 | C55—C54—H54A | 120.2 |
C15—C14—C13 | 120.60 (16) | C53—C54—H54A | 120.2 |
C15—C14—H14A | 119.7 | C54—C55—C56 | 119.7 (2) |
C13—C14—H14A | 119.7 | C54—C55—H55A | 120.1 |
C14—C15—C16 | 119.67 (16) | C56—C55—H55A | 120.1 |
C14—C15—H15A | 120.2 | C55—C56—C51 | 121.8 (2) |
C16—C15—H15A | 120.2 | C55—C56—H56A | 119.1 |
C15—C16—C11 | 118.57 (16) | C51—C56—H56A | 119.1 |
C31—P1—P2—C41 | −156.44 (9) | O2—C11—C16—C15 | −175.34 (14) |
C21—P1—P2—C41 | −88.2 (2) | C12—C11—C16—N2 | −179.20 (15) |
C9—P1—P2—C41 | 102.76 (8) | O2—C11—C16—N2 | 1.5 (2) |
C31—P1—P2—C51 | −11.94 (11) | C4—N2—C16—C15 | −68.0 (2) |
C21—P1—P2—C51 | 56.3 (2) | C5—N2—C16—C15 | 141.19 (16) |
C9—P1—P2—C51 | −112.75 (11) | C4—N2—C16—C11 | 115.37 (17) |
C31—P1—P2—C12 | 100.93 (8) | C5—N2—C16—C11 | −35.4 (2) |
C21—P1—P2—C12 | 169.2 (2) | C31—P1—C21—C22 | 17.78 (17) |
C9—P1—P2—C12 | 0.12 (7) | C9—P1—C21—C22 | 122.59 (15) |
C1—C2—C3—N1 | 6.7 (12) | P2—P1—C21—C22 | −46.3 (3) |
C1'—C2—C3—N1 | −127.3 (6) | C31—P1—C21—C26 | −171.01 (14) |
C4—N1—C3—C2 | −95.7 (3) | C9—P1—C21—C26 | −66.21 (15) |
C3—N1—C4—O1 | 4.2 (3) | P2—P1—C21—C26 | 124.90 (19) |
C3—N1—C4—N2 | −177.06 (16) | C26—C21—C22—C23 | −0.6 (3) |
C16—N2—C4—O1 | −166.34 (16) | P1—C21—C22—C23 | 170.73 (14) |
C5—N2—C4—O1 | −16.6 (2) | C21—C22—C23—C24 | 0.5 (3) |
C16—N2—C4—N1 | 14.8 (2) | C22—C23—C24—C25 | 0.4 (3) |
C5—N2—C4—N1 | 164.54 (15) | C23—C24—C25—C26 | −1.2 (3) |
C4—N2—C5—C6 | 64.4 (2) | C24—C25—C26—C21 | 1.1 (3) |
C16—N2—C5—C6 | −142.97 (17) | C22—C21—C26—C25 | −0.2 (3) |
C4—N2—C5—C10 | −117.71 (17) | P1—C21—C26—C25 | −171.91 (16) |
C16—N2—C5—C10 | 34.9 (2) | C21—P1—C31—C32 | −99.09 (15) |
C10—C5—C6—C7 | 1.4 (3) | C9—P1—C31—C32 | 156.19 (14) |
N2—C5—C6—C7 | 179.28 (16) | P2—P1—C31—C32 | 64.94 (14) |
C5—C6—C7—C8 | −0.1 (3) | C21—P1—C31—C36 | 79.46 (16) |
C6—C7—C8—C9 | −0.7 (3) | C9—P1—C31—C36 | −25.26 (17) |
C7—C8—C9—C10 | 0.2 (3) | P2—P1—C31—C36 | −116.51 (16) |
C7—C8—C9—P1 | 178.87 (14) | C36—C31—C32—C33 | −0.7 (3) |
C31—P1—C9—C8 | 89.81 (16) | P1—C31—C32—C33 | 177.92 (16) |
C21—P1—C9—C8 | −14.92 (17) | C31—C32—C33—C34 | 1.7 (3) |
P2—P1—C9—C8 | 161.87 (15) | C32—C33—C34—C35 | −1.6 (4) |
C31—P1—C9—C10 | −91.55 (14) | C33—C34—C35—C36 | 0.5 (4) |
C21—P1—C9—C10 | 163.73 (13) | C34—C35—C36—C31 | 0.5 (3) |
P2—P1—C9—C10 | −19.49 (13) | C32—C31—C36—C35 | −0.4 (3) |
C6—C5—C10—O2 | 177.46 (14) | P1—C31—C36—C35 | −178.93 (15) |
N2—C5—C10—O2 | −0.5 (2) | C51—P2—C41—C42 | 89.71 (19) |
C6—C5—C10—C9 | −2.0 (3) | C12—P2—C41—C42 | −13.5 (2) |
N2—C5—C10—C9 | 179.99 (15) | P1—P2—C41—C42 | −111.79 (18) |
C11—O2—C10—C5 | −34.2 (2) | C51—P2—C41—C46 | −92.38 (18) |
C11—O2—C10—C9 | 145.26 (14) | C12—P2—C41—C46 | 164.44 (17) |
C8—C9—C10—C5 | 1.2 (2) | P1—P2—C41—C46 | 66.12 (17) |
P1—C9—C10—C5 | −177.59 (13) | C46—C41—C42—C43 | 1.8 (4) |
C8—C9—C10—O2 | −178.29 (14) | P2—C41—C42—C43 | 179.71 (18) |
P1—C9—C10—O2 | 2.9 (2) | C41—C42—C43—C44 | 0.6 (4) |
C10—O2—C11—C12 | −145.70 (14) | C42—C43—C44—C45 | −1.9 (5) |
C10—O2—C11—C16 | 33.7 (2) | C43—C44—C45—C46 | 0.7 (5) |
C16—C11—C12—C13 | −2.4 (2) | C42—C41—C46—C45 | −2.9 (4) |
O2—C11—C12—C13 | 176.98 (13) | P2—C41—C46—C45 | 179.0 (2) |
C16—C11—C12—P2 | 177.91 (12) | C44—C45—C46—C41 | 1.8 (5) |
O2—C11—C12—P2 | −2.8 (2) | C41—P2—C51—C52 | −1.91 (19) |
C41—P2—C12—C11 | −90.99 (14) | C12—P2—C51—C52 | 101.36 (18) |
C51—P2—C12—C11 | 164.10 (14) | P1—P2—C51—C52 | −147.71 (15) |
P1—P2—C12—C11 | 19.34 (13) | C41—P2—C51—C56 | 175.42 (15) |
C41—P2—C12—C13 | 89.29 (15) | C12—P2—C51—C56 | −81.31 (16) |
C51—P2—C12—C13 | −15.62 (16) | P1—P2—C51—C56 | 29.6 (2) |
P1—P2—C12—C13 | −160.38 (14) | C56—C51—C52—C53 | 1.3 (3) |
C11—C12—C13—C14 | 0.1 (2) | P2—C51—C52—C53 | 178.67 (17) |
P2—C12—C13—C14 | 179.79 (13) | C51—C52—C53—C54 | 0.2 (4) |
C12—C13—C14—C15 | 0.5 (3) | C52—C53—C54—C55 | −0.9 (4) |
C13—C14—C15—C16 | 1.1 (3) | C53—C54—C55—C56 | −0.2 (4) |
C14—C15—C16—C11 | −3.3 (2) | C54—C55—C56—C51 | 1.8 (4) |
C14—C15—C16—N2 | −179.88 (15) | C52—C51—C56—C55 | −2.4 (3) |
C12—C11—C16—C15 | 4.0 (2) | P2—C51—C56—C55 | −179.96 (17) |