Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022172/su6137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022172/su61372sup2.hkl |
CCDC reference: 229991
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C37H38N2 | Dx = 1.150 Mg m−3 |
Mr = 510.69 | Melting point: 224 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 20.694 (7) Å | Cell parameters from 625 reflections |
b = 12.031 (4) Å | θ = 2.1–25.0° |
c = 23.694 (8) Å | µ = 0.07 mm−1 |
V = 5899 (3) Å3 | T = 293 K |
Z = 8 | Prism, yellow |
F(000) = 2192 | 0.30 × 0.20 × 0.10 mm |
Bruker SMART CCD area detector diffractometer | 1878 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.132 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
φ and ω scans | h = −24→24 |
22761 measured reflections | k = −14→14 |
5112 independent reflections | l = −16→28 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0637P)2 + 2.0005P] where P = (Fo2 + 2Fc2)/3 |
5112 reflections | (Δ/σ)max = 0.002 |
352 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 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 | ||
C1 | 0.23266 (17) | 0.3796 (3) | 0.48395 (15) | 0.0582 (10) | |
H1A | 0.2604 | 0.3281 | 0.5041 | 0.070* | |
H1B | 0.2598 | 0.4303 | 0.4627 | 0.070* | |
C2 | 0.22118 (19) | 0.2916 (3) | 0.39181 (15) | 0.0637 (11) | |
H2A | 0.1933 | 0.2416 | 0.3708 | 0.076* | |
H2B | 0.2615 | 0.2532 | 0.3990 | 0.076* | |
C3 | 0.22607 (19) | 0.4686 (3) | 0.57666 (16) | 0.0642 (11) | |
H3A | 0.1993 | 0.5192 | 0.5983 | 0.077* | |
H3B | 0.2663 | 0.5065 | 0.5681 | 0.077* | |
C4 | 0.1651 (2) | 0.5412 (3) | 0.49639 (18) | 0.0764 (13) | |
H4A | 0.1906 | 0.6055 | 0.5071 | 0.092* | |
H4B | 0.1687 | 0.5328 | 0.4558 | 0.092* | |
C5 | 0.0972 (2) | 0.5629 (4) | 0.5107 (2) | 0.1124 (18) | |
H5A | 0.0937 | 0.5775 | 0.5508 | 0.135* | |
H5B | 0.0716 | 0.4974 | 0.5022 | 0.135* | |
C6 | 0.0700 (3) | 0.6628 (4) | 0.4776 (2) | 0.130 (2) | |
H6A | 0.0257 | 0.6746 | 0.4880 | 0.195* | |
H6B | 0.0726 | 0.6479 | 0.4378 | 0.195* | |
H6C | 0.0948 | 0.7280 | 0.4863 | 0.195* | |
C7 | 0.1640 (2) | 0.2189 (3) | 0.47441 (16) | 0.0699 (12) | |
H7A | 0.1930 | 0.1568 | 0.4679 | 0.084* | |
H7B | 0.1628 | 0.2326 | 0.5147 | 0.084* | |
C8 | 0.0991 (2) | 0.1883 (4) | 0.4552 (2) | 0.1053 (17) | |
H8A | 0.1007 | 0.1667 | 0.4158 | 0.126* | |
H8B | 0.0706 | 0.2519 | 0.4585 | 0.126* | |
C9 | 0.0723 (2) | 0.0908 (4) | 0.4908 (2) | 0.134 (2) | |
H9A | 0.0299 | 0.0715 | 0.4776 | 0.201* | |
H9B | 0.0699 | 0.1127 | 0.5297 | 0.201* | |
H9C | 0.1004 | 0.0277 | 0.4873 | 0.201* | |
C10 | 0.2347 (2) | 0.3944 (3) | 0.35606 (15) | 0.0552 (10) | |
C11 | 0.2972 (2) | 0.4276 (3) | 0.34345 (16) | 0.0620 (11) | |
C12 | 0.3539 (2) | 0.3751 (4) | 0.36364 (18) | 0.0849 (14) | |
H12A | 0.3492 | 0.3138 | 0.3872 | 0.102* | |
C13 | 0.4146 (3) | 0.4091 (5) | 0.3507 (2) | 0.1055 (17) | |
H13A | 0.4502 | 0.3717 | 0.3654 | 0.127* | |
C14 | 0.4237 (3) | 0.5011 (5) | 0.3148 (2) | 0.1087 (18) | |
H14A | 0.4653 | 0.5240 | 0.3054 | 0.130* | |
C15 | 0.3725 (3) | 0.5556 (4) | 0.2942 (2) | 0.0895 (15) | |
H15A | 0.3792 | 0.6159 | 0.2704 | 0.107* | |
C16 | 0.3080 (2) | 0.5243 (4) | 0.30767 (16) | 0.0667 (12) | |
C17 | 0.2551 (3) | 0.5814 (4) | 0.28855 (17) | 0.0735 (13) | |
H17A | 0.2620 | 0.6430 | 0.2656 | 0.088* | |
C18 | 0.1927 (2) | 0.5533 (3) | 0.30111 (16) | 0.0660 (11) | |
C19 | 0.1381 (3) | 0.6135 (4) | 0.28158 (18) | 0.0838 (14) | |
H19A | 0.1450 | 0.6777 | 0.2605 | 0.101* | |
C20 | 0.0773 (3) | 0.5823 (4) | 0.2921 (2) | 0.0938 (15) | |
H20A | 0.0429 | 0.6234 | 0.2778 | 0.113* | |
C21 | 0.0657 (2) | 0.4861 (4) | 0.32513 (19) | 0.0844 (14) | |
H21A | 0.0235 | 0.4644 | 0.3328 | 0.101* | |
C22 | 0.1157 (2) | 0.4258 (4) | 0.34560 (16) | 0.0720 (12) | |
H22A | 0.1067 | 0.3631 | 0.3672 | 0.086* | |
C23 | 0.1813 (2) | 0.4544 (3) | 0.33549 (15) | 0.0579 (10) | |
C24 | 0.2404 (2) | 0.3669 (3) | 0.61199 (15) | 0.0561 (10) | |
C25 | 0.3036 (2) | 0.3329 (4) | 0.62310 (16) | 0.0634 (11) | |
C26 | 0.3603 (2) | 0.3868 (4) | 0.60368 (18) | 0.0885 (15) | |
H26A | 0.3554 | 0.4503 | 0.5817 | 0.106* | |
C27 | 0.4210 (3) | 0.3519 (5) | 0.6150 (2) | 0.1061 (18) | |
H27A | 0.4564 | 0.3915 | 0.6016 | 0.127* | |
C28 | 0.4302 (3) | 0.2547 (6) | 0.6475 (3) | 0.111 (2) | |
H28A | 0.4718 | 0.2302 | 0.6553 | 0.133* | |
C29 | 0.3795 (3) | 0.1978 (4) | 0.6670 (2) | 0.0952 (16) | |
H29A | 0.3868 | 0.1335 | 0.6879 | 0.114* | |
C30 | 0.3146 (2) | 0.2324 (4) | 0.65695 (18) | 0.0709 (12) | |
C31 | 0.2618 (3) | 0.1763 (4) | 0.67818 (17) | 0.0749 (13) | |
H31A | 0.2688 | 0.1129 | 0.6997 | 0.090* | |
C32 | 0.1995 (2) | 0.2101 (4) | 0.66889 (16) | 0.0656 (11) | |
C33 | 0.1457 (3) | 0.1529 (4) | 0.69168 (18) | 0.0902 (15) | |
H33A | 0.1529 | 0.0895 | 0.7132 | 0.108* | |
C34 | 0.0848 (3) | 0.1869 (5) | 0.6833 (2) | 0.1058 (18) | |
H34A | 0.0505 | 0.1483 | 0.6994 | 0.127* | |
C35 | 0.0731 (2) | 0.2821 (5) | 0.6497 (2) | 0.0944 (16) | |
H35A | 0.0309 | 0.3055 | 0.6432 | 0.113* | |
C36 | 0.1233 (2) | 0.3394 (4) | 0.62699 (16) | 0.0743 (12) | |
H36A | 0.1144 | 0.4016 | 0.6050 | 0.089* | |
C37 | 0.1880 (2) | 0.3082 (3) | 0.63542 (14) | 0.0571 (10) | |
N1 | 0.19039 (14) | 0.3188 (2) | 0.44569 (12) | 0.0549 (8) | |
N2 | 0.19309 (14) | 0.4415 (2) | 0.52376 (13) | 0.0563 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.059 (3) | 0.063 (2) | 0.052 (3) | −0.005 (2) | 0.002 (2) | −0.001 (2) |
C2 | 0.076 (3) | 0.059 (3) | 0.057 (3) | −0.002 (2) | 0.005 (2) | 0.000 (2) |
C3 | 0.077 (3) | 0.058 (3) | 0.057 (3) | −0.007 (2) | −0.003 (2) | −0.004 (2) |
C4 | 0.077 (3) | 0.076 (3) | 0.076 (3) | 0.003 (3) | 0.002 (2) | 0.001 (2) |
C5 | 0.098 (4) | 0.116 (4) | 0.123 (5) | 0.029 (3) | 0.011 (3) | 0.030 (4) |
C6 | 0.126 (5) | 0.120 (5) | 0.144 (5) | 0.052 (4) | 0.002 (4) | 0.026 (4) |
C7 | 0.075 (3) | 0.072 (3) | 0.063 (3) | −0.006 (2) | 0.000 (2) | 0.009 (2) |
C8 | 0.082 (4) | 0.109 (4) | 0.124 (4) | −0.023 (3) | −0.016 (3) | 0.041 (3) |
C9 | 0.121 (5) | 0.124 (5) | 0.158 (5) | −0.064 (4) | −0.023 (4) | 0.070 (4) |
C10 | 0.065 (3) | 0.053 (3) | 0.047 (3) | 0.000 (2) | 0.006 (2) | −0.0042 (19) |
C11 | 0.065 (3) | 0.071 (3) | 0.050 (3) | 0.004 (2) | 0.009 (2) | −0.010 (2) |
C12 | 0.076 (4) | 0.089 (4) | 0.090 (4) | 0.001 (3) | 0.029 (3) | −0.005 (3) |
C13 | 0.077 (4) | 0.123 (5) | 0.117 (5) | 0.010 (3) | 0.022 (3) | −0.001 (4) |
C14 | 0.085 (5) | 0.123 (5) | 0.118 (5) | −0.015 (4) | 0.033 (4) | −0.008 (4) |
C15 | 0.105 (5) | 0.089 (4) | 0.074 (3) | −0.017 (3) | 0.024 (3) | −0.006 (3) |
C16 | 0.078 (4) | 0.071 (3) | 0.050 (3) | −0.013 (3) | 0.010 (2) | −0.005 (2) |
C17 | 0.100 (4) | 0.065 (3) | 0.055 (3) | −0.011 (3) | 0.008 (3) | 0.001 (2) |
C18 | 0.087 (4) | 0.065 (3) | 0.046 (3) | −0.003 (3) | −0.002 (2) | −0.006 (2) |
C19 | 0.113 (4) | 0.074 (3) | 0.064 (3) | 0.013 (3) | 0.000 (3) | 0.006 (2) |
C20 | 0.100 (4) | 0.108 (4) | 0.074 (4) | 0.025 (3) | −0.013 (3) | 0.009 (3) |
C21 | 0.081 (4) | 0.099 (4) | 0.073 (3) | −0.002 (3) | −0.008 (3) | 0.004 (3) |
C22 | 0.074 (3) | 0.083 (3) | 0.059 (3) | −0.001 (3) | −0.007 (2) | 0.005 (2) |
C23 | 0.071 (3) | 0.060 (3) | 0.043 (3) | −0.006 (2) | 0.000 (2) | −0.006 (2) |
C24 | 0.062 (3) | 0.060 (3) | 0.047 (3) | −0.003 (2) | 0.001 (2) | −0.011 (2) |
C25 | 0.068 (3) | 0.072 (3) | 0.050 (3) | −0.004 (2) | 0.001 (2) | −0.018 (2) |
C26 | 0.067 (4) | 0.116 (4) | 0.082 (4) | −0.002 (3) | 0.009 (3) | −0.017 (3) |
C27 | 0.062 (4) | 0.144 (6) | 0.112 (5) | −0.005 (4) | 0.016 (3) | −0.021 (4) |
C28 | 0.087 (5) | 0.138 (6) | 0.108 (5) | 0.032 (4) | −0.007 (4) | −0.037 (4) |
C29 | 0.108 (5) | 0.093 (4) | 0.085 (4) | 0.024 (4) | −0.015 (3) | −0.026 (3) |
C30 | 0.078 (4) | 0.079 (3) | 0.056 (3) | 0.018 (3) | −0.015 (2) | −0.027 (2) |
C31 | 0.100 (4) | 0.065 (3) | 0.060 (3) | −0.003 (3) | −0.010 (3) | −0.005 (2) |
C32 | 0.081 (4) | 0.069 (3) | 0.047 (3) | −0.010 (3) | −0.004 (2) | −0.003 (2) |
C33 | 0.109 (4) | 0.096 (4) | 0.065 (3) | −0.032 (3) | −0.014 (3) | 0.018 (3) |
C34 | 0.101 (5) | 0.144 (5) | 0.073 (4) | −0.051 (4) | 0.001 (3) | 0.018 (3) |
C35 | 0.075 (4) | 0.136 (5) | 0.072 (4) | −0.014 (3) | 0.007 (3) | 0.006 (3) |
C36 | 0.073 (3) | 0.094 (3) | 0.056 (3) | −0.006 (3) | 0.012 (2) | 0.002 (2) |
C37 | 0.067 (3) | 0.067 (3) | 0.037 (2) | −0.004 (2) | 0.002 (2) | −0.007 (2) |
N1 | 0.066 (2) | 0.0524 (19) | 0.0460 (19) | −0.0129 (16) | 0.0075 (16) | 0.0041 (16) |
N2 | 0.068 (2) | 0.054 (2) | 0.047 (2) | 0.0063 (17) | 0.0012 (17) | 0.0043 (16) |
C1—N2 | 1.454 (4) | C14—H14A | 0.9300 |
C1—N1 | 1.457 (4) | C15—C16 | 1.423 (6) |
C1—H1A | 0.9700 | C15—H15A | 0.9300 |
C1—H1B | 0.9700 | C16—C17 | 1.369 (5) |
C2—N1 | 1.464 (4) | C17—C18 | 1.368 (5) |
C2—C10 | 1.525 (5) | C17—H17A | 0.9300 |
C2—H2A | 0.9700 | C18—C19 | 1.419 (6) |
C2—H2B | 0.9700 | C18—C23 | 1.461 (5) |
C3—N2 | 1.464 (4) | C19—C20 | 1.337 (6) |
C3—C24 | 1.513 (5) | C19—H19A | 0.9300 |
C3—H3A | 0.9700 | C20—C21 | 1.418 (6) |
C3—H3B | 0.9700 | C20—H20A | 0.9300 |
C4—C5 | 1.470 (5) | C21—C22 | 1.353 (5) |
C4—N2 | 1.482 (4) | C21—H21A | 0.9300 |
C4—H4A | 0.9700 | C22—C23 | 1.422 (5) |
C4—H4B | 0.9700 | C22—H22A | 0.9300 |
C5—C6 | 1.542 (6) | C24—C25 | 1.395 (5) |
C5—H5A | 0.9700 | C24—C37 | 1.408 (5) |
C5—H5B | 0.9700 | C25—C26 | 1.417 (5) |
C6—H6A | 0.9600 | C25—C30 | 1.469 (6) |
C6—H6B | 0.9600 | C26—C27 | 1.351 (6) |
C6—H6C | 0.9600 | C26—H26A | 0.9300 |
C7—C8 | 1.466 (5) | C27—C28 | 1.413 (7) |
C7—N1 | 1.485 (4) | C27—H27A | 0.9300 |
C7—H7A | 0.9700 | C28—C29 | 1.336 (7) |
C7—H7B | 0.9700 | C28—H28A | 0.9300 |
C8—C9 | 1.549 (5) | C29—C30 | 1.426 (6) |
C8—H8A | 0.9700 | C29—H29A | 0.9300 |
C8—H8B | 0.9700 | C30—C31 | 1.380 (6) |
C9—H9A | 0.9600 | C31—C32 | 1.370 (5) |
C9—H9B | 0.9600 | C31—H31A | 0.9300 |
C9—H9C | 0.9600 | C32—C33 | 1.415 (6) |
C10—C11 | 1.387 (5) | C32—C37 | 1.442 (5) |
C10—C23 | 1.406 (5) | C33—C34 | 1.340 (6) |
C11—C12 | 1.415 (5) | C33—H33A | 0.9300 |
C11—C16 | 1.456 (5) | C34—C35 | 1.415 (6) |
C12—C13 | 1.357 (6) | C34—H34A | 0.9300 |
C12—H12A | 0.9300 | C35—C36 | 1.357 (5) |
C13—C14 | 1.408 (7) | C35—H35A | 0.9300 |
C13—H13A | 0.9300 | C36—C37 | 1.406 (5) |
C14—C15 | 1.339 (6) | C36—H36A | 0.9300 |
N2—C1—N1 | 108.8 (3) | C17—C16—C15 | 122.9 (5) |
N2—C1—H1A | 109.9 | C17—C16—C11 | 118.1 (4) |
N1—C1—H1A | 109.9 | C15—C16—C11 | 119.0 (4) |
N2—C1—H1B | 109.9 | C18—C17—C16 | 124.0 (4) |
N1—C1—H1B | 109.9 | C18—C17—H17A | 118.0 |
H1A—C1—H1B | 108.3 | C16—C17—H17A | 118.0 |
N1—C2—C10 | 112.5 (3) | C17—C18—C19 | 123.6 (4) |
N1—C2—H2A | 109.1 | C17—C18—C23 | 118.3 (4) |
C10—C2—H2A | 109.1 | C19—C18—C23 | 118.1 (4) |
N1—C2—H2B | 109.1 | C20—C19—C18 | 123.0 (5) |
C10—C2—H2B | 109.1 | C20—C19—H19A | 118.5 |
H2A—C2—H2B | 107.8 | C18—C19—H19A | 118.5 |
N2—C3—C24 | 112.6 (3) | C19—C20—C21 | 119.4 (5) |
N2—C3—H3A | 109.1 | C19—C20—H20A | 120.3 |
C24—C3—H3A | 109.1 | C21—C20—H20A | 120.3 |
N2—C3—H3B | 109.1 | C22—C21—C20 | 120.4 (5) |
C24—C3—H3B | 109.1 | C22—C21—H21A | 119.8 |
H3A—C3—H3B | 107.8 | C20—C21—H21A | 119.8 |
C5—C4—N2 | 114.6 (4) | C21—C22—C23 | 122.7 (4) |
C5—C4—H4A | 108.6 | C21—C22—H22A | 118.6 |
N2—C4—H4A | 108.6 | C23—C22—H22A | 118.6 |
C5—C4—H4B | 108.6 | C10—C23—C22 | 124.6 (4) |
N2—C4—H4B | 108.6 | C10—C23—C18 | 119.0 (4) |
H4A—C4—H4B | 107.6 | C22—C23—C18 | 116.3 (4) |
C4—C5—C6 | 111.7 (4) | C25—C24—C37 | 120.1 (4) |
C4—C5—H5A | 109.3 | C25—C24—C3 | 121.7 (4) |
C6—C5—H5A | 109.3 | C37—C24—C3 | 118.2 (4) |
C4—C5—H5B | 109.3 | C24—C25—C26 | 125.5 (4) |
C6—C5—H5B | 109.3 | C24—C25—C30 | 119.3 (4) |
H5A—C5—H5B | 107.9 | C26—C25—C30 | 115.2 (4) |
C5—C6—H6A | 109.5 | C27—C26—C25 | 124.3 (5) |
C5—C6—H6B | 109.5 | C27—C26—H26A | 117.9 |
H6A—C6—H6B | 109.5 | C25—C26—H26A | 117.9 |
C5—C6—H6C | 109.5 | C26—C27—C28 | 119.4 (5) |
H6A—C6—H6C | 109.5 | C26—C27—H27A | 120.3 |
H6B—C6—H6C | 109.5 | C28—C27—H27A | 120.3 |
C8—C7—N1 | 113.4 (3) | C29—C28—C27 | 120.5 (6) |
C8—C7—H7A | 108.9 | C29—C28—H28A | 119.7 |
N1—C7—H7A | 108.9 | C27—C28—H28A | 119.7 |
C8—C7—H7B | 108.9 | C28—C29—C30 | 122.1 (6) |
N1—C7—H7B | 108.9 | C28—C29—H29A | 119.0 |
H7A—C7—H7B | 107.7 | C30—C29—H29A | 119.0 |
C7—C8—C9 | 110.5 (4) | C31—C30—C29 | 122.8 (5) |
C7—C8—H8A | 109.6 | C31—C30—C25 | 118.6 (4) |
C9—C8—H8A | 109.6 | C29—C30—C25 | 118.6 (5) |
C7—C8—H8B | 109.6 | C32—C31—C30 | 122.9 (4) |
C9—C8—H8B | 109.6 | C32—C31—H31A | 118.6 |
H8A—C8—H8B | 108.1 | C30—C31—H31A | 118.6 |
C8—C9—H9A | 109.5 | C31—C32—C33 | 122.3 (5) |
C8—C9—H9B | 109.5 | C31—C32—C37 | 119.1 (4) |
H9A—C9—H9B | 109.5 | C33—C32—C37 | 118.6 (4) |
C8—C9—H9C | 109.5 | C34—C33—C32 | 122.3 (5) |
H9A—C9—H9C | 109.5 | C34—C33—H33A | 118.8 |
H9B—C9—H9C | 109.5 | C32—C33—H33A | 118.8 |
C11—C10—C23 | 120.7 (4) | C33—C34—C35 | 119.4 (5) |
C11—C10—C2 | 121.6 (4) | C33—C34—H34A | 120.3 |
C23—C10—C2 | 117.7 (4) | C35—C34—H34A | 120.3 |
C10—C11—C12 | 124.9 (4) | C36—C35—C34 | 120.3 (5) |
C10—C11—C16 | 119.9 (4) | C36—C35—H35A | 119.9 |
C12—C11—C16 | 115.3 (4) | C34—C35—H35A | 119.9 |
C13—C12—C11 | 123.8 (5) | C35—C36—C37 | 122.5 (4) |
C13—C12—H12A | 118.1 | C35—C36—H36A | 118.8 |
C11—C12—H12A | 118.1 | C37—C36—H36A | 118.8 |
C12—C13—C14 | 119.8 (5) | C36—C37—C24 | 123.0 (4) |
C12—C13—H13A | 120.1 | C36—C37—C32 | 117.0 (4) |
C14—C13—H13A | 120.1 | C24—C37—C32 | 120.0 (4) |
C15—C14—C13 | 120.0 (5) | C1—N1—C2 | 113.2 (3) |
C15—C14—H14A | 120.0 | C1—N1—C7 | 110.0 (3) |
C13—C14—H14A | 120.0 | C2—N1—C7 | 112.3 (3) |
C14—C15—C16 | 122.1 (5) | C1—N2—C3 | 114.0 (3) |
C14—C15—H15A | 118.9 | C1—N2—C4 | 110.5 (3) |
C16—C15—H15A | 118.9 | C3—N2—C4 | 112.1 (3) |
N2—C4—C5—C6 | −176.0 (4) | C3—C24—C25—C30 | −179.1 (3) |
N1—C7—C8—C9 | −174.6 (4) | C24—C25—C26—C27 | −179.9 (4) |
N1—C2—C10—C11 | 114.7 (4) | C30—C25—C26—C27 | −0.8 (6) |
N1—C2—C10—C23 | −66.0 (4) | C25—C26—C27—C28 | 1.1 (7) |
C23—C10—C11—C12 | 177.8 (4) | C26—C27—C28—C29 | −0.2 (8) |
C2—C10—C11—C12 | −3.0 (6) | C27—C28—C29—C30 | −0.8 (8) |
C23—C10—C11—C16 | −1.2 (5) | C28—C29—C30—C31 | −178.1 (5) |
C2—C10—C11—C16 | 178.1 (3) | C28—C29—C30—C25 | 1.1 (7) |
C10—C11—C12—C13 | 179.9 (4) | C24—C25—C30—C31 | −1.9 (5) |
C16—C11—C12—C13 | −1.1 (6) | C26—C25—C30—C31 | 178.9 (4) |
C11—C12—C13—C14 | −0.5 (8) | C24—C25—C30—C29 | 178.9 (4) |
C12—C13—C14—C15 | 0.9 (8) | C26—C25—C30—C29 | −0.3 (5) |
C13—C14—C15—C16 | 0.4 (8) | C29—C30—C31—C32 | 179.5 (4) |
C14—C15—C16—C17 | 177.7 (5) | C25—C30—C31—C32 | 0.3 (6) |
C14—C15—C16—C11 | −2.1 (7) | C30—C31—C32—C33 | −178.9 (4) |
C10—C11—C16—C17 | 1.5 (6) | C30—C31—C32—C37 | 0.1 (6) |
C12—C11—C16—C17 | −177.5 (4) | C31—C32—C33—C34 | 178.9 (5) |
C10—C11—C16—C15 | −178.7 (4) | C37—C32—C33—C34 | −0.1 (7) |
C12—C11—C16—C15 | 2.3 (5) | C32—C33—C34—C35 | 1.1 (8) |
C15—C16—C17—C18 | −179.7 (4) | C33—C34—C35—C36 | −1.0 (8) |
C11—C16—C17—C18 | 0.1 (6) | C34—C35—C36—C37 | −0.1 (7) |
C16—C17—C18—C19 | 179.4 (4) | C35—C36—C37—C24 | 179.9 (4) |
C16—C17—C18—C23 | −2.0 (6) | C35—C36—C37—C32 | 1.2 (6) |
C17—C18—C19—C20 | 176.9 (4) | C25—C24—C37—C36 | 178.5 (3) |
C23—C18—C19—C20 | −1.7 (6) | C3—C24—C37—C36 | 0.6 (5) |
C18—C19—C20—C21 | 1.4 (7) | C25—C24—C37—C32 | −2.8 (5) |
C19—C20—C21—C22 | −0.5 (7) | C3—C24—C37—C32 | 179.3 (3) |
C20—C21—C22—C23 | 0.0 (7) | C31—C32—C37—C36 | 179.9 (4) |
C11—C10—C23—C22 | 179.2 (3) | C33—C32—C37—C36 | −1.0 (5) |
C2—C10—C23—C22 | −0.1 (5) | C31—C32—C37—C24 | 1.1 (5) |
C11—C10—C23—C18 | −0.7 (5) | C33—C32—C37—C24 | −179.8 (4) |
C2—C10—C23—C18 | 180.0 (3) | N2—C1—N1—C2 | 156.5 (3) |
C21—C22—C23—C10 | 179.8 (4) | N2—C1—N1—C7 | −77.0 (4) |
C21—C22—C23—C18 | −0.3 (6) | C10—C2—N1—C1 | −67.7 (4) |
C17—C18—C23—C10 | 2.3 (5) | C10—C2—N1—C7 | 167.1 (3) |
C19—C18—C23—C10 | −179.0 (3) | C8—C7—N1—C1 | 148.3 (4) |
C17—C18—C23—C22 | −177.6 (3) | C8—C7—N1—C2 | −84.7 (4) |
C19—C18—C23—C22 | 1.1 (5) | N1—C1—N2—C3 | 156.6 (3) |
N2—C3—C24—C25 | 114.9 (4) | N1—C1—N2—C4 | −76.1 (4) |
N2—C3—C24—C37 | −67.2 (4) | C24—C3—N2—C1 | −67.5 (4) |
C37—C24—C25—C26 | −177.8 (4) | C24—C3—N2—C4 | 166.0 (3) |
C3—C24—C25—C26 | 0.0 (6) | C5—C4—N2—C1 | 138.0 (4) |
C37—C24—C25—C30 | 3.1 (5) | C5—C4—N2—C3 | −93.6 (5) |