Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032538/bt6756sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032538/bt6756Isup2.hkl |
CCDC reference: 289653
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C34H31ClN2O3 | F(000) = 1160 |
Mr = 551.06 | Dx = 1.235 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4958 reflections |
a = 11.3180 (8) Å | θ = 2.3–27.2° |
b = 11.6376 (8) Å | µ = 0.17 mm−1 |
c = 23.0980 (16) Å | T = 293 K |
β = 103.000 (1)° | Block, colourless |
V = 2964.4 (4) Å3 | 0.26 × 0.24 × 0.20 mm |
Z = 4 |
Bruker SMART APEX area detector diffractometer | 4748 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −14→14 |
17499 measured reflections | k = −15→10 |
6766 independent reflections | l = −29→29 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0679P)2 + 0.61P] where P = (Fo2 + 2Fc2)/3 |
6766 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | ||
Cl1 | 1.08586 (5) | 0.96037 (5) | 0.13744 (3) | 0.0868 (2) | |
O1 | 0.77516 (12) | 0.32500 (13) | −0.01879 (6) | 0.0668 (4) | |
O2 | 0.48165 (14) | −0.06350 (16) | 0.11410 (8) | 0.0892 (5) | |
O3 | 0.77282 (14) | 0.30822 (15) | 0.22502 (8) | 0.0839 (5) | |
N1 | 0.82798 (13) | 0.24719 (13) | 0.07727 (6) | 0.0506 (4) | |
N2 | 1.09946 (13) | 0.35115 (14) | 0.19204 (7) | 0.0540 (4) | |
C1 | 0.95557 (14) | 0.26111 (15) | 0.10979 (7) | 0.0454 (4) | |
H1 | 1.0003 | 0.1888 | 0.1106 | 0.055* | |
C2 | 0.97427 (15) | 0.33887 (16) | 0.05811 (7) | 0.0465 (4) | |
H2 | 0.9818 | 0.4198 | 0.0701 | 0.056* | |
C3 | 0.84249 (16) | 0.30818 (16) | 0.02868 (8) | 0.0498 (4) | |
C4 | 1.07021 (16) | 0.30550 (17) | 0.02552 (8) | 0.0516 (4) | |
C5 | 1.0759 (2) | 0.1955 (2) | 0.00374 (10) | 0.0690 (6) | |
H5 | 1.0197 | 0.1406 | 0.0093 | 0.083* | |
C6 | 1.1642 (3) | 0.1664 (3) | −0.02619 (11) | 0.0871 (8) | |
H6 | 1.1675 | 0.0921 | −0.0406 | 0.105* | |
C7 | 1.2467 (2) | 0.2463 (3) | −0.03476 (12) | 0.0972 (9) | |
H7 | 1.3061 | 0.2264 | −0.0550 | 0.117* | |
C8 | 1.2420 (2) | 0.3555 (3) | −0.01366 (12) | 0.0940 (9) | |
H8 | 1.2982 | 0.4099 | −0.0197 | 0.113* | |
C9 | 1.15410 (18) | 0.3854 (2) | 0.01670 (9) | 0.0684 (6) | |
H9 | 1.1517 | 0.4598 | 0.0312 | 0.082* | |
C10 | 0.73722 (15) | 0.17118 (16) | 0.08671 (8) | 0.0496 (4) | |
C11 | 0.76627 (16) | 0.08249 (17) | 0.12699 (9) | 0.0553 (5) | |
H11 | 0.8456 | 0.0742 | 0.1487 | 0.066* | |
C12 | 0.67876 (18) | 0.00618 (19) | 0.13535 (10) | 0.0614 (5) | |
H12 | 0.6991 | −0.0534 | 0.1626 | 0.074* | |
C13 | 0.56110 (18) | 0.01796 (19) | 0.10342 (9) | 0.0622 (5) | |
C14 | 0.53099 (18) | 0.1068 (2) | 0.06388 (10) | 0.0734 (6) | |
H14 | 0.4512 | 0.1155 | 0.0428 | 0.088* | |
C15 | 0.61854 (18) | 0.1836 (2) | 0.05525 (10) | 0.0683 (6) | |
H15 | 0.5977 | 0.2436 | 0.0283 | 0.082* | |
C16 | 0.3582 (2) | −0.0507 (3) | 0.08639 (14) | 0.1072 (10) | |
H16A | 0.3284 | 0.0202 | 0.0990 | 0.161* | |
H16B | 0.3129 | −0.1137 | 0.0972 | 0.161* | |
H16C | 0.3490 | −0.0497 | 0.0440 | 0.161* | |
C17 | 0.97422 (15) | 0.31211 (15) | 0.17151 (7) | 0.0465 (4) | |
H17 | 0.9573 | 0.2530 | 0.1988 | 0.056* | |
C18 | 0.89826 (15) | 0.41868 (16) | 0.17669 (8) | 0.0471 (4) | |
H18 | 0.8820 | 0.4606 | 0.1389 | 0.057* | |
C19 | 0.98307 (17) | 0.49344 (18) | 0.22596 (8) | 0.0546 (5) | |
H19 | 0.9445 | 0.5030 | 0.2596 | 0.066* | |
C20 | 1.09496 (19) | 0.41783 (19) | 0.24486 (9) | 0.0654 (6) | |
H20A | 1.1674 | 0.4643 | 0.2572 | 0.079* | |
H20B | 1.0873 | 0.3678 | 0.2774 | 0.079* | |
C21 | 0.77823 (17) | 0.38806 (18) | 0.19243 (8) | 0.0550 (5) | |
C22 | 0.66804 (17) | 0.4575 (2) | 0.16775 (8) | 0.0588 (5) | |
C23 | 0.6723 (2) | 0.5739 (2) | 0.15919 (12) | 0.0850 (7) | |
H23 | 0.7471 | 0.6108 | 0.1659 | 0.102* | |
C24 | 0.5670 (3) | 0.6372 (3) | 0.14067 (16) | 0.1114 (10) | |
H24 | 0.5709 | 0.7166 | 0.1371 | 0.134* | |
C25 | 0.4582 (3) | 0.5829 (4) | 0.12781 (15) | 0.1186 (12) | |
H25 | 0.3875 | 0.6249 | 0.1142 | 0.142* | |
C26 | 0.4523 (2) | 0.4653 (4) | 0.13485 (14) | 0.1154 (12) | |
H26 | 0.3777 | 0.4282 | 0.1258 | 0.138* | |
C27 | 0.5564 (2) | 0.4033 (3) | 0.15517 (11) | 0.0852 (8) | |
H27 | 0.5519 | 0.3244 | 0.1605 | 0.102* | |
C28 | 1.00908 (15) | 0.60994 (17) | 0.20353 (8) | 0.0501 (4) | |
C29 | 0.96246 (17) | 0.70793 (19) | 0.22344 (9) | 0.0619 (5) | |
H29 | 0.9150 | 0.7014 | 0.2513 | 0.074* | |
C30 | 0.98438 (18) | 0.81535 (19) | 0.20310 (10) | 0.0656 (6) | |
H30 | 0.9515 | 0.8805 | 0.2168 | 0.079* | |
C31 | 1.05522 (16) | 0.82475 (17) | 0.16249 (9) | 0.0570 (5) | |
C32 | 1.10271 (16) | 0.72962 (18) | 0.14117 (9) | 0.0566 (5) | |
H32 | 1.1497 | 0.7370 | 0.1131 | 0.068* | |
C33 | 1.07982 (16) | 0.62300 (17) | 0.16192 (8) | 0.0545 (5) | |
H33 | 1.1124 | 0.5582 | 0.1478 | 0.065* | |
C34 | 1.1883 (2) | 0.2583 (2) | 0.20374 (12) | 0.0833 (7) | |
H34A | 1.1650 | 0.2035 | 0.2302 | 0.125* | |
H34B | 1.2666 | 0.2892 | 0.2217 | 0.125* | |
H34C | 1.1917 | 0.2211 | 0.1671 | 0.125* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0685 (3) | 0.0554 (3) | 0.1353 (6) | 0.0002 (3) | 0.0205 (3) | 0.0188 (3) |
O1 | 0.0581 (7) | 0.0823 (11) | 0.0519 (8) | −0.0016 (7) | −0.0048 (6) | 0.0136 (7) |
O2 | 0.0668 (9) | 0.0960 (12) | 0.1061 (13) | −0.0329 (9) | 0.0224 (9) | 0.0106 (10) |
O3 | 0.0727 (10) | 0.0870 (12) | 0.0998 (12) | −0.0005 (8) | 0.0356 (9) | 0.0396 (10) |
N1 | 0.0460 (8) | 0.0516 (9) | 0.0488 (8) | −0.0088 (7) | −0.0007 (6) | 0.0078 (7) |
N2 | 0.0462 (8) | 0.0554 (9) | 0.0530 (9) | 0.0003 (7) | −0.0045 (6) | −0.0007 (8) |
C1 | 0.0422 (8) | 0.0423 (9) | 0.0485 (9) | −0.0028 (7) | 0.0031 (7) | 0.0050 (8) |
C2 | 0.0486 (9) | 0.0437 (10) | 0.0450 (9) | −0.0034 (7) | 0.0061 (7) | 0.0031 (8) |
C3 | 0.0489 (9) | 0.0488 (10) | 0.0485 (10) | 0.0004 (8) | 0.0043 (8) | 0.0027 (9) |
C4 | 0.0507 (9) | 0.0591 (12) | 0.0425 (9) | −0.0007 (8) | 0.0054 (7) | 0.0068 (9) |
C5 | 0.0704 (13) | 0.0697 (15) | 0.0671 (13) | 0.0009 (11) | 0.0157 (11) | −0.0051 (11) |
C6 | 0.0895 (17) | 0.100 (2) | 0.0718 (15) | 0.0270 (16) | 0.0169 (13) | −0.0098 (14) |
C7 | 0.0734 (16) | 0.147 (3) | 0.0775 (17) | 0.0209 (18) | 0.0296 (13) | 0.0068 (19) |
C8 | 0.0725 (15) | 0.130 (3) | 0.0869 (18) | −0.0119 (16) | 0.0327 (13) | 0.0131 (18) |
C9 | 0.0622 (12) | 0.0796 (16) | 0.0643 (13) | −0.0096 (11) | 0.0163 (10) | 0.0088 (11) |
C10 | 0.0466 (9) | 0.0493 (11) | 0.0507 (10) | −0.0076 (8) | 0.0062 (7) | −0.0022 (9) |
C11 | 0.0450 (9) | 0.0567 (11) | 0.0620 (11) | −0.0025 (8) | 0.0075 (8) | 0.0064 (10) |
C12 | 0.0596 (11) | 0.0568 (12) | 0.0697 (13) | −0.0038 (9) | 0.0183 (9) | 0.0093 (10) |
C13 | 0.0560 (11) | 0.0659 (14) | 0.0668 (12) | −0.0157 (10) | 0.0183 (9) | −0.0050 (11) |
C14 | 0.0458 (10) | 0.0895 (17) | 0.0775 (15) | −0.0157 (11) | −0.0017 (10) | 0.0066 (13) |
C15 | 0.0551 (11) | 0.0730 (15) | 0.0690 (13) | −0.0101 (10) | −0.0025 (10) | 0.0147 (11) |
C16 | 0.0661 (15) | 0.135 (3) | 0.122 (2) | −0.0453 (16) | 0.0242 (15) | −0.004 (2) |
C17 | 0.0461 (9) | 0.0462 (10) | 0.0441 (9) | −0.0046 (7) | 0.0038 (7) | 0.0080 (8) |
C18 | 0.0493 (9) | 0.0504 (10) | 0.0415 (9) | −0.0051 (8) | 0.0098 (7) | 0.0058 (8) |
C19 | 0.0623 (11) | 0.0601 (12) | 0.0429 (9) | −0.0090 (9) | 0.0149 (8) | −0.0042 (9) |
C20 | 0.0704 (13) | 0.0658 (13) | 0.0505 (11) | −0.0073 (10) | −0.0068 (9) | 0.0017 (10) |
C21 | 0.0552 (10) | 0.0600 (12) | 0.0512 (10) | −0.0058 (9) | 0.0150 (8) | 0.0049 (10) |
C22 | 0.0501 (10) | 0.0758 (15) | 0.0513 (10) | −0.0030 (9) | 0.0132 (8) | 0.0054 (10) |
C23 | 0.0580 (12) | 0.0790 (17) | 0.117 (2) | 0.0064 (12) | 0.0186 (13) | 0.0151 (15) |
C24 | 0.0786 (18) | 0.101 (2) | 0.156 (3) | 0.0269 (16) | 0.0279 (18) | 0.031 (2) |
C25 | 0.0645 (17) | 0.166 (4) | 0.121 (3) | 0.033 (2) | 0.0122 (16) | 0.046 (2) |
C26 | 0.0546 (14) | 0.171 (4) | 0.110 (2) | −0.0075 (18) | −0.0044 (14) | 0.030 (2) |
C27 | 0.0614 (13) | 0.109 (2) | 0.0792 (15) | −0.0144 (13) | 0.0029 (11) | 0.0141 (15) |
C28 | 0.0478 (9) | 0.0543 (11) | 0.0488 (10) | −0.0045 (8) | 0.0123 (8) | −0.0079 (9) |
C29 | 0.0560 (11) | 0.0660 (14) | 0.0694 (13) | −0.0031 (10) | 0.0258 (9) | −0.0103 (11) |
C30 | 0.0555 (11) | 0.0558 (13) | 0.0872 (15) | 0.0053 (9) | 0.0191 (10) | −0.0113 (11) |
C31 | 0.0429 (9) | 0.0482 (11) | 0.0762 (13) | −0.0016 (8) | 0.0054 (9) | 0.0026 (10) |
C32 | 0.0500 (10) | 0.0603 (13) | 0.0617 (11) | −0.0058 (9) | 0.0171 (9) | 0.0009 (10) |
C33 | 0.0552 (10) | 0.0518 (11) | 0.0595 (11) | −0.0024 (8) | 0.0191 (9) | −0.0084 (9) |
C34 | 0.0579 (12) | 0.0783 (16) | 0.0968 (17) | 0.0119 (11) | −0.0183 (12) | −0.0020 (14) |
Cl1—C31 | 1.743 (2) | C16—H16A | 0.9600 |
O1—C3 | 1.202 (2) | C16—H16B | 0.9600 |
O2—C13 | 1.367 (2) | C16—H16C | 0.9600 |
O2—C16 | 1.408 (3) | C17—C18 | 1.529 (3) |
O3—C21 | 1.206 (2) | C17—H17 | 0.9800 |
N1—C3 | 1.369 (2) | C18—C21 | 1.525 (2) |
N1—C10 | 1.409 (2) | C18—C19 | 1.576 (2) |
N1—C1 | 1.479 (2) | C18—H18 | 0.9800 |
N2—C20 | 1.456 (3) | C19—C28 | 1.504 (3) |
N2—C34 | 1.460 (3) | C19—C20 | 1.523 (3) |
N2—C17 | 1.462 (2) | C19—H19 | 0.9800 |
C1—C17 | 1.514 (2) | C20—H20A | 0.9700 |
C1—C2 | 1.550 (2) | C20—H20B | 0.9700 |
C1—H1 | 0.9800 | C21—C22 | 1.488 (3) |
C2—C4 | 1.505 (3) | C22—C23 | 1.370 (3) |
C2—C3 | 1.536 (2) | C22—C27 | 1.383 (3) |
C2—H2 | 0.9800 | C23—C24 | 1.385 (3) |
C4—C9 | 1.377 (3) | C23—H23 | 0.9300 |
C4—C5 | 1.382 (3) | C24—C25 | 1.356 (4) |
C5—C6 | 1.379 (3) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.381 (5) |
C6—C7 | 1.362 (4) | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—C27 | 1.371 (4) |
C7—C8 | 1.367 (4) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—H27 | 0.9300 |
C8—C9 | 1.385 (3) | C28—C29 | 1.378 (3) |
C8—H8 | 0.9300 | C28—C33 | 1.391 (3) |
C9—H9 | 0.9300 | C29—C30 | 1.377 (3) |
C10—C11 | 1.379 (3) | C29—H29 | 0.9300 |
C10—C15 | 1.383 (3) | C30—C31 | 1.369 (3) |
C11—C12 | 1.376 (3) | C30—H30 | 0.9300 |
C11—H11 | 0.9300 | C31—C32 | 1.370 (3) |
C12—C13 | 1.376 (3) | C32—C33 | 1.376 (3) |
C12—H12 | 0.9300 | C32—H32 | 0.9300 |
C13—C14 | 1.371 (3) | C33—H33 | 0.9300 |
C14—C15 | 1.381 (3) | C34—H34A | 0.9600 |
C14—H14 | 0.9300 | C34—H34B | 0.9600 |
C15—H15 | 0.9300 | C34—H34C | 0.9600 |
C13—O2—C16 | 118.1 (2) | N2—C17—H17 | 108.9 |
C3—N1—C10 | 132.72 (15) | C1—C17—H17 | 108.9 |
C3—N1—C1 | 94.36 (13) | C18—C17—H17 | 108.9 |
C10—N1—C1 | 130.73 (14) | C21—C18—C17 | 112.07 (15) |
C20—N2—C34 | 113.1 (2) | C21—C18—C19 | 112.79 (15) |
C20—N2—C17 | 102.9 (2) | C17—C18—C19 | 104.04 (14) |
C34—N2—C17 | 114.0 (2) | C21—C18—H18 | 109.3 |
N1—C1—C17 | 115.74 (14) | C17—C18—H18 | 109.3 |
N1—C1—C2 | 87.69 (12) | C19—C18—H18 | 109.3 |
C17—C1—C2 | 118.81 (15) | C28—C19—C20 | 113.89 (16) |
N1—C1—H1 | 110.9 | C28—C19—C18 | 112.56 (14) |
C17—C1—H1 | 110.9 | C20—C19—C18 | 102.72 (16) |
C2—C1—H1 | 110.9 | C28—C19—H19 | 109.1 |
C4—C2—C3 | 117.19 (15) | C20—C19—H19 | 109.1 |
C4—C2—C1 | 118.27 (15) | C18—C19—H19 | 109.1 |
C3—C2—C1 | 85.29 (12) | N2—C20—C19 | 104.55 (14) |
C4—C2—H2 | 111.2 | N2—C20—H20A | 110.8 |
C3—C2—H2 | 111.2 | C19—C20—H20A | 110.8 |
C1—C2—H2 | 111.2 | N2—C20—H20B | 110.8 |
O1—C3—N1 | 131.60 (17) | C19—C20—H20B | 110.8 |
O1—C3—C2 | 135.98 (17) | H20A—C20—H20B | 108.9 |
N1—C3—C2 | 92.37 (13) | O3—C21—C22 | 120.13 (17) |
C9—C4—C5 | 118.8 (2) | O3—C21—C18 | 120.11 (18) |
C9—C4—C2 | 119.93 (19) | C22—C21—C18 | 119.75 (17) |
C5—C4—C2 | 121.27 (18) | C23—C22—C27 | 118.7 (2) |
C6—C5—C4 | 120.5 (2) | C23—C22—C21 | 122.56 (19) |
C6—C5—H5 | 119.7 | C27—C22—C21 | 118.7 (2) |
C4—C5—H5 | 119.7 | C22—C23—C24 | 121.0 (3) |
C7—C6—C5 | 120.2 (3) | C22—C23—H23 | 119.5 |
C7—C6—H6 | 119.9 | C24—C23—H23 | 119.5 |
C5—C6—H6 | 119.9 | C25—C24—C23 | 119.7 (3) |
C6—C7—C8 | 120.0 (3) | C25—C24—H24 | 120.1 |
C6—C7—H7 | 120.0 | C23—C24—H24 | 120.1 |
C8—C7—H7 | 120.0 | C24—C25—C26 | 120.1 (3) |
C7—C8—C9 | 120.3 (3) | C24—C25—H25 | 120.0 |
C7—C8—H8 | 119.9 | C26—C25—H25 | 120.0 |
C9—C8—H8 | 119.9 | C27—C26—C25 | 120.1 (3) |
C4—C9—C8 | 120.2 (3) | C27—C26—H26 | 120.0 |
C4—C9—H9 | 119.9 | C25—C26—H26 | 120.0 |
C8—C9—H9 | 119.9 | C26—C27—C22 | 120.4 (3) |
C11—C10—C15 | 119.24 (17) | C26—C27—H27 | 119.8 |
C11—C10—N1 | 120.18 (15) | C22—C27—H27 | 119.8 |
C15—C10—N1 | 120.57 (17) | C29—C28—C33 | 117.60 (18) |
C12—C11—C10 | 120.53 (18) | C29—C28—C19 | 120.78 (17) |
C12—C11—H11 | 119.7 | C33—C28—C19 | 121.62 (17) |
C10—C11—H11 | 119.7 | C30—C29—C28 | 121.69 (19) |
C11—C12—C13 | 120.1 (2) | C30—C29—H29 | 119.2 |
C11—C12—H12 | 120.0 | C28—C29—H29 | 119.2 |
C13—C12—H12 | 120.0 | C31—C30—C29 | 118.98 (19) |
O2—C13—C14 | 124.64 (19) | C31—C30—H30 | 120.5 |
O2—C13—C12 | 115.5 (2) | C29—C30—H30 | 120.5 |
C14—C13—C12 | 119.84 (18) | C30—C31—C32 | 121.31 (19) |
C13—C14—C15 | 120.33 (19) | C30—C31—Cl1 | 119.41 (16) |
C13—C14—H14 | 119.8 | C32—C31—Cl1 | 119.28 (16) |
C15—C14—H14 | 119.8 | C31—C32—C33 | 118.94 (18) |
C14—C15—C10 | 120.0 (2) | C31—C32—H32 | 120.5 |
C14—C15—H15 | 120.0 | C33—C32—H32 | 120.5 |
C10—C15—H15 | 120.0 | C32—C33—C28 | 121.48 (18) |
O2—C16—H16A | 109.5 | C32—C33—H33 | 119.3 |
O2—C16—H16B | 109.5 | C28—C33—H33 | 119.3 |
H16A—C16—H16B | 109.5 | N2—C34—H34A | 109.5 |
O2—C16—H16C | 109.5 | N2—C34—H34B | 109.5 |
H16A—C16—H16C | 109.5 | H34A—C34—H34B | 109.5 |
H16B—C16—H16C | 109.5 | N2—C34—H34C | 109.5 |
N2—C17—C1 | 110.29 (14) | H34A—C34—H34C | 109.5 |
N2—C17—C18 | 104.11 (14) | H34B—C34—H34C | 109.5 |
C1—C17—C18 | 115.45 (14) | ||
C3—N1—C1—C17 | 125.27 (16) | C34—N2—C17—C18 | 167.0 (2) |
C10—N1—C1—C17 | −70.2 (2) | N1—C1—C17—N2 | −164.11 (14) |
C3—N1—C1—C2 | 4.21 (14) | C2—C1—C17—N2 | −61.75 (19) |
C10—N1—C1—C2 | 168.71 (19) | N1—C1—C17—C18 | −46.5 (2) |
N1—C1—C2—C4 | −122.19 (16) | C2—C1—C17—C18 | 55.9 (2) |
C17—C1—C2—C4 | 119.53 (17) | N2—C17—C18—C21 | −147.02 (15) |
N1—C1—C2—C3 | −3.75 (13) | C1—C17—C18—C21 | 91.94 (18) |
C17—C1—C2—C3 | −122.04 (16) | N2—C17—C18—C19 | −24.87 (17) |
C10—N1—C3—O1 | 9.6 (4) | C1—C17—C18—C19 | −145.91 (14) |
C1—N1—C3—O1 | 173.6 (2) | C21—C18—C19—C28 | −117.86 (17) |
C10—N1—C3—C2 | −168.3 (2) | C17—C18—C19—C28 | 120.46 (16) |
C1—N1—C3—C2 | −4.25 (14) | C21—C18—C19—C20 | 119.22 (17) |
C4—C2—C3—O1 | −54.1 (3) | C17—C18—C19—C20 | −2.46 (18) |
C1—C2—C3—O1 | −173.6 (2) | C34—N2—C20—C19 | −169.7 (2) |
C4—C2—C3—N1 | 123.52 (17) | C17—N2—C20—C19 | −46.26 (19) |
C1—C2—C3—N1 | 4.05 (14) | C28—C19—C20—N2 | −92.82 (18) |
C3—C2—C4—C9 | 130.17 (19) | C18—C19—C20—N2 | 29.20 (19) |
C1—C2—C4—C9 | −129.97 (18) | C17—C18—C21—O3 | 35.0 (3) |
C3—C2—C4—C5 | −49.5 (2) | C19—C18—C21—O3 | −82.0 (2) |
C1—C2—C4—C5 | 50.3 (2) | C17—C18—C21—C22 | −145.35 (17) |
C9—C4—C5—C6 | 0.1 (3) | C19—C18—C21—C22 | 97.6 (2) |
C2—C4—C5—C6 | 179.81 (19) | O3—C21—C22—C23 | 143.9 (2) |
C4—C5—C6—C7 | −0.2 (4) | C18—C21—C22—C23 | −35.7 (3) |
C5—C6—C7—C8 | 0.0 (4) | O3—C21—C22—C27 | −33.4 (3) |
C6—C7—C8—C9 | 0.3 (4) | C18—C21—C22—C27 | 147.0 (2) |
C5—C4—C9—C8 | 0.2 (3) | C27—C22—C23—C24 | 2.6 (4) |
C2—C4—C9—C8 | −179.49 (19) | C21—C22—C23—C24 | −174.7 (2) |
C7—C8—C9—C4 | −0.4 (4) | C22—C23—C24—C25 | −3.4 (5) |
C3—N1—C10—C11 | 149.3 (2) | C23—C24—C25—C26 | 1.9 (5) |
C1—N1—C10—C11 | −9.5 (3) | C24—C25—C26—C27 | 0.3 (6) |
C3—N1—C10—C15 | −29.9 (3) | C25—C26—C27—C22 | −1.1 (5) |
C1—N1—C10—C15 | 171.39 (19) | C23—C22—C27—C26 | −0.4 (4) |
C15—C10—C11—C12 | 0.8 (3) | C21—C22—C27—C26 | 177.1 (2) |
N1—C10—C11—C12 | −178.34 (18) | C20—C19—C28—C29 | −132.55 (19) |
C10—C11—C12—C13 | 0.0 (3) | C18—C19—C28—C29 | 111.04 (19) |
C16—O2—C13—C14 | −5.4 (4) | C20—C19—C28—C33 | 47.9 (2) |
C16—O2—C13—C12 | 174.9 (2) | C18—C19—C28—C33 | −68.5 (2) |
C11—C12—C13—O2 | 178.7 (2) | C33—C28—C29—C30 | 0.1 (3) |
C11—C12—C13—C14 | −0.9 (3) | C19—C28—C29—C30 | −179.46 (19) |
O2—C13—C14—C15 | −178.6 (2) | C28—C29—C30—C31 | −0.6 (3) |
C12—C13—C14—C15 | 1.0 (4) | C29—C30—C31—C32 | 1.1 (3) |
C13—C14—C15—C10 | −0.2 (4) | C29—C30—C31—Cl1 | −178.85 (16) |
C11—C10—C15—C14 | −0.7 (3) | C30—C31—C32—C33 | −1.0 (3) |
N1—C10—C15—C14 | 178.4 (2) | Cl1—C31—C32—C33 | 178.91 (14) |
C20—N2—C17—C1 | 168.57 (15) | C31—C32—C33—C28 | 0.5 (3) |
C34—N2—C17—C1 | −68.6 (2) | C29—C28—C33—C32 | 0.0 (3) |
C20—N2—C17—C18 | 44.15 (17) | C19—C28—C33—C32 | 179.52 (17) |