Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001930/ya6278sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001930/ya6278Isup2.hkl |
CCDC reference: 298586
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C33H29N3 | Dx = 1.185 Mg m−3 |
Mr = 467.59 | Melting point: 437 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.875 (3) Å | Cell parameters from 2276 reflections |
b = 15.037 (3) Å | θ = 2.3–22.8° |
c = 13.591 (3) Å | µ = 0.07 mm−1 |
β = 95.107 (4)° | T = 294 K |
V = 2620.6 (10) Å3 | Block, yellow |
Z = 4 | 0.22 × 0.20 × 0.16 mm |
F(000) = 992 |
Bruker SMART-1000 CCD area-detector diffractometer | 5382 independent reflections |
Radiation source: fine-focus sealed tube | 2534 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −14→16 |
Tmin = 0.985, Tmax = 0.989 | k = −18→10 |
14697 measured reflections | l = −17→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.0947P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.126 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.16 e Å−3 |
5382 reflections | Δρmin = −0.16 e Å−3 |
327 parameters |
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 | ||
N1 | 0.26578 (13) | −0.01522 (11) | 0.82921 (13) | 0.0576 (5) | |
N2 | 0.63401 (12) | 0.20823 (12) | 0.66041 (12) | 0.0498 (5) | |
N3 | 0.71507 (13) | 0.24643 (11) | 0.61725 (13) | 0.0515 (5) | |
C1 | 0.26906 (17) | −0.09848 (15) | 0.87709 (15) | 0.0507 (6) | |
C2 | 0.18008 (18) | −0.15077 (15) | 0.87819 (15) | 0.0581 (6) | |
H2 | 0.1171 | −0.1309 | 0.8470 | 0.070* | |
C3 | 0.1849 (2) | −0.23207 (16) | 0.92541 (17) | 0.0704 (7) | |
H3 | 0.1243 | −0.2657 | 0.9255 | 0.084* | |
C4 | 0.2755 (3) | −0.26543 (16) | 0.97228 (18) | 0.0735 (8) | |
C5 | 0.3636 (2) | −0.21309 (18) | 0.97057 (18) | 0.0741 (7) | |
H5 | 0.4264 | −0.2334 | 1.0018 | 0.089* | |
C6 | 0.36101 (18) | −0.13167 (15) | 0.92390 (17) | 0.0622 (6) | |
H6 | 0.4219 | −0.0984 | 0.9238 | 0.075* | |
C7 | 0.2783 (3) | −0.35429 (17) | 1.0256 (2) | 0.1195 (12) | |
H7A | 0.2712 | −0.3447 | 1.0945 | 0.179* | |
H7B | 0.3435 | −0.3834 | 1.0180 | 0.179* | |
H7C | 0.2220 | −0.3909 | 0.9979 | 0.179* | |
C8 | 0.18033 (15) | 0.04386 (14) | 0.83211 (15) | 0.0478 (5) | |
C9 | 0.15464 (17) | 0.10051 (15) | 0.75333 (16) | 0.0590 (6) | |
H9 | 0.1907 | 0.0965 | 0.6972 | 0.071* | |
C10 | 0.07649 (17) | 0.16283 (15) | 0.75684 (16) | 0.0594 (6) | |
H10 | 0.0620 | 0.2009 | 0.7034 | 0.071* | |
C11 | 0.01907 (16) | 0.17018 (14) | 0.83790 (16) | 0.0509 (6) | |
C12 | 0.04321 (15) | 0.11176 (14) | 0.91489 (15) | 0.0499 (5) | |
H12 | 0.0048 | 0.1141 | 0.9696 | 0.060* | |
C13 | 0.12242 (15) | 0.05000 (13) | 0.91347 (15) | 0.0489 (5) | |
H13 | 0.1371 | 0.0123 | 0.9672 | 0.059* | |
C14 | −0.06401 (19) | 0.24048 (15) | 0.84233 (19) | 0.0751 (7) | |
H14A | −0.0436 | 0.2817 | 0.8945 | 0.113* | |
H14B | −0.1287 | 0.2128 | 0.8548 | 0.113* | |
H14C | −0.0725 | 0.2717 | 0.7805 | 0.113* | |
C15 | 0.35528 (16) | 0.01741 (14) | 0.78531 (16) | 0.0523 (6) | |
C16 | 0.40056 (17) | −0.03018 (15) | 0.71369 (17) | 0.0638 (7) | |
H16 | 0.3758 | −0.0866 | 0.6961 | 0.077* | |
C17 | 0.48305 (16) | 0.00576 (14) | 0.66773 (16) | 0.0608 (6) | |
H17 | 0.5134 | −0.0274 | 0.6201 | 0.073* | |
C18 | 0.52098 (15) | 0.08981 (13) | 0.69128 (15) | 0.0457 (5) | |
C19 | 0.47693 (16) | 0.13550 (14) | 0.76630 (16) | 0.0545 (6) | |
H19 | 0.5027 | 0.1912 | 0.7855 | 0.065* | |
C20 | 0.39599 (16) | 0.09951 (14) | 0.81233 (16) | 0.0556 (6) | |
H20 | 0.3682 | 0.1311 | 0.8626 | 0.067* | |
C21 | 0.60587 (15) | 0.12809 (14) | 0.64094 (15) | 0.0507 (6) | |
H21 | 0.6390 | 0.0947 | 0.5954 | 0.061* | |
C22 | 0.77350 (15) | 0.19932 (12) | 0.54925 (15) | 0.0416 (5) | |
C23 | 0.84658 (18) | 0.13801 (14) | 0.58387 (18) | 0.0633 (6) | |
H23 | 0.8572 | 0.1260 | 0.6511 | 0.076* | |
C24 | 0.9039 (2) | 0.09446 (16) | 0.5185 (2) | 0.0861 (9) | |
H24 | 0.9531 | 0.0524 | 0.5417 | 0.103* | |
C25 | 0.8896 (2) | 0.11215 (17) | 0.4194 (2) | 0.0789 (8) | |
H25 | 0.9288 | 0.0823 | 0.3755 | 0.095* | |
C26 | 0.8174 (2) | 0.17382 (17) | 0.38534 (18) | 0.0717 (7) | |
H26 | 0.8079 | 0.1866 | 0.3182 | 0.086* | |
C27 | 0.75842 (17) | 0.21734 (14) | 0.45035 (17) | 0.0577 (6) | |
H27 | 0.7086 | 0.2588 | 0.4270 | 0.069* | |
C28 | 0.72950 (16) | 0.33802 (13) | 0.63326 (14) | 0.0450 (5) | |
C29 | 0.81880 (16) | 0.38010 (14) | 0.60682 (15) | 0.0532 (6) | |
H29 | 0.8706 | 0.3471 | 0.5801 | 0.064* | |
C30 | 0.8312 (2) | 0.47036 (16) | 0.61996 (17) | 0.0665 (7) | |
H30 | 0.8908 | 0.4980 | 0.6008 | 0.080* | |
C31 | 0.7566 (2) | 0.52007 (16) | 0.66105 (19) | 0.0750 (8) | |
H31 | 0.7651 | 0.5811 | 0.6694 | 0.090* | |
C32 | 0.6694 (2) | 0.47842 (17) | 0.68955 (17) | 0.0708 (7) | |
H32 | 0.6192 | 0.5116 | 0.7183 | 0.085* | |
C33 | 0.65486 (17) | 0.38841 (15) | 0.67639 (15) | 0.0565 (6) | |
H33 | 0.5953 | 0.3612 | 0.6963 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0441 (11) | 0.0565 (12) | 0.0761 (13) | 0.0004 (9) | 0.0268 (10) | 0.0129 (10) |
N2 | 0.0443 (11) | 0.0520 (12) | 0.0560 (11) | 0.0002 (9) | 0.0197 (9) | 0.0045 (9) |
N3 | 0.0508 (11) | 0.0400 (11) | 0.0678 (12) | −0.0017 (8) | 0.0287 (10) | −0.0029 (9) |
C1 | 0.0513 (15) | 0.0560 (15) | 0.0470 (13) | −0.0034 (12) | 0.0162 (11) | −0.0035 (11) |
C2 | 0.0614 (16) | 0.0677 (17) | 0.0468 (13) | −0.0107 (12) | 0.0131 (11) | 0.0011 (12) |
C3 | 0.095 (2) | 0.0634 (18) | 0.0568 (16) | −0.0191 (15) | 0.0298 (15) | −0.0039 (13) |
C4 | 0.107 (2) | 0.0575 (17) | 0.0612 (17) | 0.0140 (17) | 0.0392 (17) | 0.0031 (13) |
C5 | 0.087 (2) | 0.0706 (19) | 0.0679 (17) | 0.0262 (16) | 0.0219 (15) | 0.0030 (14) |
C6 | 0.0569 (16) | 0.0640 (17) | 0.0678 (16) | 0.0056 (12) | 0.0165 (13) | −0.0054 (13) |
C7 | 0.176 (3) | 0.076 (2) | 0.117 (3) | 0.035 (2) | 0.072 (2) | 0.0325 (18) |
C8 | 0.0387 (13) | 0.0582 (14) | 0.0479 (13) | −0.0040 (10) | 0.0120 (11) | 0.0049 (11) |
C9 | 0.0518 (15) | 0.0818 (17) | 0.0464 (14) | 0.0005 (12) | 0.0201 (11) | 0.0070 (12) |
C10 | 0.0548 (15) | 0.0742 (17) | 0.0502 (14) | 0.0019 (12) | 0.0098 (12) | 0.0137 (12) |
C11 | 0.0424 (13) | 0.0590 (15) | 0.0519 (14) | −0.0019 (10) | 0.0077 (11) | 0.0018 (11) |
C12 | 0.0417 (13) | 0.0659 (15) | 0.0440 (13) | −0.0043 (11) | 0.0139 (10) | 0.0005 (11) |
C13 | 0.0430 (13) | 0.0619 (14) | 0.0423 (12) | −0.0057 (11) | 0.0063 (10) | 0.0063 (10) |
C14 | 0.0726 (18) | 0.0765 (18) | 0.0786 (18) | 0.0158 (14) | 0.0194 (14) | 0.0079 (14) |
C15 | 0.0416 (13) | 0.0556 (15) | 0.0620 (15) | −0.0021 (11) | 0.0170 (11) | 0.0030 (12) |
C16 | 0.0587 (15) | 0.0595 (15) | 0.0763 (17) | −0.0141 (11) | 0.0241 (13) | −0.0119 (13) |
C17 | 0.0541 (15) | 0.0601 (16) | 0.0724 (16) | −0.0058 (12) | 0.0287 (13) | −0.0117 (12) |
C18 | 0.0374 (12) | 0.0482 (14) | 0.0532 (13) | 0.0012 (10) | 0.0129 (10) | 0.0009 (10) |
C19 | 0.0507 (14) | 0.0502 (13) | 0.0651 (15) | −0.0044 (11) | 0.0190 (12) | −0.0035 (11) |
C20 | 0.0511 (14) | 0.0585 (15) | 0.0605 (14) | −0.0011 (11) | 0.0227 (12) | −0.0051 (12) |
C21 | 0.0461 (13) | 0.0509 (15) | 0.0574 (14) | −0.0010 (11) | 0.0175 (11) | −0.0009 (11) |
C22 | 0.0371 (12) | 0.0391 (12) | 0.0503 (14) | −0.0025 (9) | 0.0138 (10) | 0.0016 (10) |
C23 | 0.0685 (17) | 0.0605 (15) | 0.0629 (15) | 0.0181 (13) | 0.0171 (13) | 0.0124 (12) |
C24 | 0.090 (2) | 0.0691 (18) | 0.103 (2) | 0.0350 (15) | 0.0335 (19) | 0.0062 (17) |
C25 | 0.083 (2) | 0.0685 (18) | 0.091 (2) | 0.0006 (15) | 0.0408 (18) | −0.0250 (16) |
C26 | 0.0767 (19) | 0.089 (2) | 0.0513 (15) | −0.0127 (15) | 0.0152 (14) | −0.0121 (14) |
C27 | 0.0522 (15) | 0.0658 (16) | 0.0557 (15) | 0.0057 (11) | 0.0075 (12) | 0.0042 (12) |
C28 | 0.0486 (14) | 0.0416 (13) | 0.0443 (13) | 0.0042 (10) | 0.0017 (10) | 0.0022 (10) |
C29 | 0.0505 (14) | 0.0487 (15) | 0.0603 (14) | −0.0017 (11) | 0.0048 (11) | 0.0021 (11) |
C30 | 0.0719 (18) | 0.0514 (16) | 0.0735 (17) | −0.0127 (13) | −0.0086 (14) | 0.0009 (13) |
C31 | 0.091 (2) | 0.0465 (15) | 0.0832 (19) | 0.0028 (15) | −0.0172 (17) | −0.0117 (14) |
C32 | 0.084 (2) | 0.0607 (18) | 0.0663 (17) | 0.0192 (14) | −0.0024 (15) | −0.0186 (13) |
C33 | 0.0607 (15) | 0.0570 (15) | 0.0522 (14) | 0.0070 (12) | 0.0065 (11) | −0.0070 (12) |
N1—C1 | 1.410 (2) | C15—C20 | 1.378 (3) |
N1—C8 | 1.417 (2) | C15—C16 | 1.379 (3) |
N1—C15 | 1.431 (2) | C16—C17 | 1.389 (3) |
N2—C21 | 1.279 (2) | C16—H16 | 0.9300 |
N2—N3 | 1.368 (2) | C17—C18 | 1.382 (3) |
N3—C28 | 1.404 (2) | C17—H17 | 0.9300 |
N3—C22 | 1.430 (2) | C18—C19 | 1.391 (3) |
C1—C6 | 1.386 (3) | C18—C21 | 1.458 (3) |
C1—C2 | 1.391 (3) | C19—C20 | 1.373 (3) |
C2—C3 | 1.380 (3) | C19—H19 | 0.9300 |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.374 (3) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C22—C27 | 1.368 (3) |
C4—C5 | 1.382 (3) | C22—C23 | 1.370 (3) |
C4—C7 | 1.519 (3) | C23—C24 | 1.371 (3) |
C5—C6 | 1.378 (3) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.369 (3) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—H7A | 0.9600 | C25—C26 | 1.364 (3) |
C7—H7B | 0.9600 | C25—H25 | 0.9300 |
C7—H7C | 0.9600 | C26—C27 | 1.380 (3) |
C8—C9 | 1.385 (3) | C26—H26 | 0.9300 |
C8—C13 | 1.391 (3) | C27—H27 | 0.9300 |
C9—C10 | 1.379 (3) | C28—C29 | 1.387 (3) |
C9—H9 | 0.9300 | C28—C33 | 1.393 (3) |
C10—C11 | 1.385 (3) | C29—C30 | 1.376 (3) |
C10—H10 | 0.9300 | C29—H29 | 0.9300 |
C11—C12 | 1.380 (3) | C30—C31 | 1.374 (3) |
C11—C14 | 1.509 (3) | C30—H30 | 0.9300 |
C12—C13 | 1.381 (3) | C31—C32 | 1.371 (3) |
C12—H12 | 0.9300 | C31—H31 | 0.9300 |
C13—H13 | 0.9300 | C32—C33 | 1.376 (3) |
C14—H14A | 0.9600 | C32—H32 | 0.9300 |
C14—H14B | 0.9600 | C33—H33 | 0.9300 |
C14—H14C | 0.9600 | ||
C1—N1—C8 | 122.36 (16) | C20—C15—N1 | 119.83 (19) |
C1—N1—C15 | 120.32 (17) | C16—C15—N1 | 121.6 (2) |
C8—N1—C15 | 116.91 (17) | C15—C16—C17 | 120.3 (2) |
C21—N2—N3 | 121.31 (16) | C15—C16—H16 | 119.9 |
N2—N3—C28 | 116.15 (16) | C17—C16—H16 | 119.9 |
N2—N3—C22 | 122.29 (16) | C18—C17—C16 | 121.3 (2) |
C28—N3—C22 | 121.07 (16) | C18—C17—H17 | 119.3 |
C6—C1—C2 | 117.5 (2) | C16—C17—H17 | 119.3 |
C6—C1—N1 | 121.4 (2) | C17—C18—C19 | 117.55 (18) |
C2—C1—N1 | 121.1 (2) | C17—C18—C21 | 121.08 (18) |
C3—C2—C1 | 120.2 (2) | C19—C18—C21 | 121.35 (19) |
C3—C2—H2 | 119.9 | C20—C19—C18 | 121.0 (2) |
C1—C2—H2 | 119.9 | C20—C19—H19 | 119.5 |
C4—C3—C2 | 122.7 (2) | C18—C19—H19 | 119.5 |
C4—C3—H3 | 118.6 | C19—C20—C15 | 121.2 (2) |
C2—C3—H3 | 118.6 | C19—C20—H20 | 119.4 |
C3—C4—C5 | 116.7 (2) | C15—C20—H20 | 119.4 |
C3—C4—C7 | 121.7 (3) | N2—C21—C18 | 119.01 (19) |
C5—C4—C7 | 121.6 (3) | N2—C21—H21 | 120.5 |
C6—C5—C4 | 121.8 (3) | C18—C21—H21 | 120.5 |
C6—C5—H5 | 119.1 | C27—C22—C23 | 120.24 (19) |
C4—C5—H5 | 119.1 | C27—C22—N3 | 120.00 (18) |
C5—C6—C1 | 121.1 (2) | C23—C22—N3 | 119.73 (19) |
C5—C6—H6 | 119.5 | C22—C23—C24 | 119.4 (2) |
C1—C6—H6 | 119.5 | C22—C23—H23 | 120.3 |
C4—C7—H7A | 109.5 | C24—C23—H23 | 120.3 |
C4—C7—H7B | 109.5 | C25—C24—C23 | 120.8 (2) |
H7A—C7—H7B | 109.5 | C25—C24—H24 | 119.6 |
C4—C7—H7C | 109.5 | C23—C24—H24 | 119.6 |
H7A—C7—H7C | 109.5 | C26—C25—C24 | 119.6 (2) |
H7B—C7—H7C | 109.5 | C26—C25—H25 | 120.2 |
C9—C8—C13 | 117.76 (19) | C24—C25—H25 | 120.2 |
C9—C8—N1 | 119.77 (18) | C25—C26—C27 | 120.2 (2) |
C13—C8—N1 | 122.42 (19) | C25—C26—H26 | 119.9 |
C10—C9—C8 | 121.1 (2) | C27—C26—H26 | 119.9 |
C10—C9—H9 | 119.5 | C22—C27—C26 | 119.8 (2) |
C8—C9—H9 | 119.5 | C22—C27—H27 | 120.1 |
C9—C10—C11 | 121.6 (2) | C26—C27—H27 | 120.1 |
C9—C10—H10 | 119.2 | C29—C28—C33 | 118.6 (2) |
C11—C10—H10 | 119.2 | C29—C28—N3 | 120.56 (18) |
C12—C11—C10 | 116.88 (19) | C33—C28—N3 | 120.80 (19) |
C12—C11—C14 | 121.89 (19) | C30—C29—C28 | 120.3 (2) |
C10—C11—C14 | 121.2 (2) | C30—C29—H29 | 119.8 |
C11—C12—C13 | 122.29 (19) | C28—C29—H29 | 119.8 |
C11—C12—H12 | 118.9 | C31—C30—C29 | 120.8 (2) |
C13—C12—H12 | 118.9 | C31—C30—H30 | 119.6 |
C12—C13—C8 | 120.31 (19) | C29—C30—H30 | 119.6 |
C12—C13—H13 | 119.8 | C32—C31—C30 | 119.1 (2) |
C8—C13—H13 | 119.8 | C32—C31—H31 | 120.5 |
C11—C14—H14A | 109.5 | C30—C31—H31 | 120.5 |
C11—C14—H14B | 109.5 | C31—C32—C33 | 121.2 (2) |
H14A—C14—H14B | 109.5 | C31—C32—H32 | 119.4 |
C11—C14—H14C | 109.5 | C33—C32—H32 | 119.4 |
H14A—C14—H14C | 109.5 | C32—C33—C28 | 119.9 (2) |
H14B—C14—H14C | 109.5 | C32—C33—H33 | 120.0 |
C20—C15—C16 | 118.58 (19) | C28—C33—H33 | 120.0 |
C21—N2—N3—C28 | 171.33 (18) | C15—C16—C17—C18 | −0.8 (4) |
C21—N2—N3—C22 | −0.7 (3) | C16—C17—C18—C19 | 3.1 (3) |
C8—N1—C1—C6 | −141.9 (2) | C16—C17—C18—C21 | −178.4 (2) |
C15—N1—C1—C6 | 30.5 (3) | C17—C18—C19—C20 | −2.5 (3) |
C8—N1—C1—C2 | 38.7 (3) | C21—C18—C19—C20 | 179.04 (19) |
C15—N1—C1—C2 | −148.8 (2) | C18—C19—C20—C15 | −0.5 (3) |
C6—C1—C2—C3 | 0.6 (3) | C16—C15—C20—C19 | 2.9 (3) |
N1—C1—C2—C3 | 179.97 (18) | N1—C15—C20—C19 | −175.11 (19) |
C1—C2—C3—C4 | −0.4 (3) | N3—N2—C21—C18 | 178.18 (17) |
C2—C3—C4—C5 | 0.2 (3) | C17—C18—C21—N2 | 175.5 (2) |
C2—C3—C4—C7 | 178.7 (2) | C19—C18—C21—N2 | −6.1 (3) |
C3—C4—C5—C6 | −0.3 (3) | N2—N3—C22—C27 | 105.1 (2) |
C7—C4—C5—C6 | −178.7 (2) | C28—N3—C22—C27 | −66.6 (3) |
C4—C5—C6—C1 | 0.5 (3) | N2—N3—C22—C23 | −76.8 (3) |
C2—C1—C6—C5 | −0.6 (3) | C28—N3—C22—C23 | 111.6 (2) |
N1—C1—C6—C5 | 179.99 (19) | C27—C22—C23—C24 | −0.4 (3) |
C1—N1—C8—C9 | −149.6 (2) | N3—C22—C23—C24 | −178.6 (2) |
C15—N1—C8—C9 | 37.7 (3) | C22—C23—C24—C25 | 0.6 (4) |
C1—N1—C8—C13 | 32.9 (3) | C23—C24—C25—C26 | 0.0 (4) |
C15—N1—C8—C13 | −139.8 (2) | C24—C25—C26—C27 | −0.7 (4) |
C13—C8—C9—C10 | 2.0 (3) | C23—C22—C27—C26 | −0.3 (3) |
N1—C8—C9—C10 | −175.6 (2) | N3—C22—C27—C26 | 177.88 (19) |
C8—C9—C10—C11 | −1.4 (3) | C25—C26—C27—C22 | 0.9 (4) |
C9—C10—C11—C12 | −0.4 (3) | N2—N3—C28—C29 | 169.37 (18) |
C9—C10—C11—C14 | 178.1 (2) | C22—N3—C28—C29 | −18.5 (3) |
C10—C11—C12—C13 | 1.6 (3) | N2—N3—C28—C33 | −10.3 (3) |
C14—C11—C12—C13 | −176.9 (2) | C22—N3—C28—C33 | 161.83 (19) |
C11—C12—C13—C8 | −1.0 (3) | C33—C28—C29—C30 | −2.2 (3) |
C9—C8—C13—C12 | −0.9 (3) | N3—C28—C29—C30 | 178.07 (19) |
N1—C8—C13—C12 | 176.68 (18) | C28—C29—C30—C31 | 1.2 (3) |
C1—N1—C15—C20 | −124.7 (2) | C29—C30—C31—C32 | 0.4 (4) |
C8—N1—C15—C20 | 48.1 (3) | C30—C31—C32—C33 | −1.0 (4) |
C1—N1—C15—C16 | 57.4 (3) | C31—C32—C33—C28 | −0.1 (3) |
C8—N1—C15—C16 | −129.8 (2) | C29—C28—C33—C32 | 1.7 (3) |
C20—C15—C16—C17 | −2.2 (3) | N3—C28—C33—C32 | −178.63 (19) |
N1—C15—C16—C17 | 175.7 (2) |