Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027296/na6272sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027296/na6272Isup2.hkl |
CCDC reference: 232147
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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C32H23ClN2O3 | F(000) = 1056 |
Mr = 506.96 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5085 (9) Å | Cell parameters from 5762 reflections |
b = 9.5986 (8) Å | θ = 2.3–27.8° |
c = 23.0306 (18) Å | µ = 0.19 mm−1 |
β = 91.232 (1)° | T = 293 K |
V = 2543.5 (4) Å3 | Block, colourless |
Z = 4 | 0.21 × 0.20 × 0.20 mm |
CCD Aread Detector diffractometer | 4365 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −14→15 |
15033 measured reflections | k = −12→9 |
5829 independent reflections | l = −29→30 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0961P)2 + 0.4518P] where P = (Fo2 + 2Fc2)/3 |
5829 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.49 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 | 0.58467 (8) | 0.47853 (7) | 0.07672 (3) | 0.0923 (3) | |
N1 | 0.31891 (12) | 0.73861 (14) | 0.42971 (5) | 0.0399 (3) | |
C2 | 0.25572 (13) | 0.64243 (17) | 0.39191 (6) | 0.0364 (3) | |
C3 | 0.34992 (13) | 0.60414 (18) | 0.34645 (6) | 0.0405 (4) | |
C4 | 0.40642 (16) | 0.7502 (2) | 0.33614 (7) | 0.0479 (4) | |
H4 | 0.3550 | 0.8050 | 0.3105 | 0.057* | |
C5 | 0.40748 (18) | 0.8151 (2) | 0.39675 (8) | 0.0517 (5) | |
H5 | 0.4839 | 0.8001 | 0.4152 | 0.062* | |
C6 | 0.29528 (15) | 0.5359 (2) | 0.29125 (7) | 0.0487 (4) | |
N7 | 0.34923 (15) | 0.41263 (19) | 0.28397 (6) | 0.0574 (4) | |
H7 | 0.3334 | 0.3565 | 0.2558 | 0.069* | |
C8 | 0.43361 (16) | 0.3856 (2) | 0.32709 (7) | 0.0484 (4) | |
C9 | 0.5062 (2) | 0.2719 (2) | 0.33298 (9) | 0.0625 (5) | |
H9 | 0.5054 | 0.2005 | 0.3057 | 0.075* | |
C10 | 0.58038 (19) | 0.2683 (2) | 0.38110 (10) | 0.0629 (5) | |
H10 | 0.6298 | 0.1925 | 0.3864 | 0.075* | |
C11 | 0.58259 (16) | 0.3743 (2) | 0.42131 (9) | 0.0574 (5) | |
H11 | 0.6323 | 0.3685 | 0.4536 | 0.069* | |
C12 | 0.51142 (15) | 0.4897 (2) | 0.41408 (8) | 0.0495 (4) | |
H12 | 0.5143 | 0.5622 | 0.4408 | 0.059* | |
C13 | 0.43603 (14) | 0.49544 (18) | 0.36659 (7) | 0.0421 (4) | |
C14 | 0.52682 (18) | 0.7432 (3) | 0.30967 (8) | 0.0625 (6) | |
C15 | 0.53889 (16) | 0.6809 (2) | 0.25089 (8) | 0.0541 (5) | |
C16 | 0.63972 (19) | 0.6086 (3) | 0.23878 (10) | 0.0725 (7) | |
H16 | 0.6988 | 0.6030 | 0.2669 | 0.087* | |
C17 | 0.6539 (2) | 0.5448 (3) | 0.18571 (11) | 0.0755 (7) | |
H17 | 0.7213 | 0.4952 | 0.1781 | 0.091* | |
C18 | 0.5673 (2) | 0.5560 (2) | 0.14462 (9) | 0.0608 (5) | |
C19 | 0.46770 (19) | 0.6280 (2) | 0.15453 (8) | 0.0574 (5) | |
H19 | 0.4101 | 0.6348 | 0.1257 | 0.069* | |
C20 | 0.45310 (17) | 0.6908 (2) | 0.20794 (8) | 0.0535 (5) | |
H20 | 0.3853 | 0.7400 | 0.2151 | 0.064* | |
C21 | 0.20194 (13) | 0.52053 (16) | 0.42374 (6) | 0.0349 (3) | |
C22 | 0.24517 (15) | 0.43008 (18) | 0.46471 (7) | 0.0412 (4) | |
H22 | 0.3229 | 0.4343 | 0.4765 | 0.049* | |
C23 | 0.16986 (17) | 0.33006 (18) | 0.48882 (7) | 0.0467 (4) | |
H23 | 0.1994 | 0.2699 | 0.5171 | 0.056* | |
C24 | 0.05621 (17) | 0.31819 (18) | 0.47237 (8) | 0.0486 (4) | |
H24 | 0.0100 | 0.2500 | 0.4889 | 0.058* | |
C25 | 0.00842 (15) | 0.40937 (18) | 0.43021 (7) | 0.0445 (4) | |
C26 | −0.10712 (17) | 0.4139 (2) | 0.40866 (9) | 0.0588 (5) | |
H26 | −0.1599 | 0.3469 | 0.4206 | 0.071* | |
C27 | −0.14292 (18) | 0.5149 (3) | 0.37063 (11) | 0.0683 (6) | |
H27 | −0.2200 | 0.5152 | 0.3577 | 0.082* | |
C28 | −0.06787 (17) | 0.6184 (2) | 0.35024 (9) | 0.0594 (5) | |
H28 | −0.0946 | 0.6874 | 0.3249 | 0.071* | |
C29 | 0.04601 (15) | 0.61456 (19) | 0.36881 (7) | 0.0440 (4) | |
C30 | 0.08329 (14) | 0.51003 (16) | 0.40771 (6) | 0.0379 (3) | |
C31 | 0.14544 (15) | 0.70743 (19) | 0.35959 (6) | 0.0431 (4) | |
C32 | 0.3748 (3) | 0.9681 (2) | 0.40221 (11) | 0.0796 (7) | |
H32A | 0.3199 | 0.9958 | 0.3718 | 0.096* | |
H32B | 0.4429 | 1.0275 | 0.4008 | 0.096* | |
C33 | 0.3198 (3) | 0.9727 (2) | 0.46178 (12) | 0.0816 (8) | |
H33A | 0.3788 | 0.9765 | 0.4925 | 0.098* | |
H33B | 0.2689 | 1.0527 | 0.4652 | 0.098* | |
C34 | 0.25176 (18) | 0.83813 (19) | 0.46427 (8) | 0.0510 (4) | |
H34A | 0.2455 | 0.8061 | 0.5040 | 0.061* | |
H34B | 0.1742 | 0.8503 | 0.4477 | 0.061* | |
O35 | 0.21838 (12) | 0.5840 (2) | 0.26043 (5) | 0.0671 (4) | |
O36 | 0.61161 (15) | 0.7849 (3) | 0.33588 (8) | 0.1074 (8) | |
O37 | 0.14390 (12) | 0.81920 (15) | 0.33534 (6) | 0.0581 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1321 (7) | 0.0769 (4) | 0.0695 (4) | −0.0004 (4) | 0.0374 (4) | −0.0141 (3) |
N1 | 0.0430 (7) | 0.0427 (7) | 0.0341 (6) | −0.0055 (6) | 0.0050 (5) | −0.0011 (5) |
C2 | 0.0347 (8) | 0.0441 (8) | 0.0304 (6) | −0.0017 (6) | 0.0025 (6) | 0.0021 (6) |
C3 | 0.0345 (8) | 0.0580 (10) | 0.0291 (7) | −0.0076 (7) | 0.0028 (6) | −0.0034 (6) |
C4 | 0.0441 (9) | 0.0619 (11) | 0.0378 (8) | −0.0130 (8) | 0.0060 (7) | 0.0019 (7) |
C5 | 0.0532 (11) | 0.0577 (11) | 0.0445 (9) | −0.0192 (9) | 0.0081 (8) | −0.0022 (8) |
C6 | 0.0411 (9) | 0.0762 (13) | 0.0290 (7) | −0.0136 (9) | 0.0044 (7) | −0.0056 (7) |
N7 | 0.0639 (10) | 0.0707 (11) | 0.0374 (7) | −0.0161 (9) | 0.0000 (7) | −0.0179 (7) |
C8 | 0.0478 (10) | 0.0571 (11) | 0.0407 (8) | −0.0123 (8) | 0.0083 (7) | −0.0108 (7) |
C9 | 0.0711 (13) | 0.0545 (12) | 0.0625 (11) | −0.0066 (10) | 0.0139 (10) | −0.0173 (9) |
C10 | 0.0510 (11) | 0.0589 (12) | 0.0792 (14) | 0.0047 (9) | 0.0080 (10) | −0.0032 (10) |
C11 | 0.0361 (9) | 0.0709 (13) | 0.0650 (11) | 0.0021 (9) | −0.0041 (8) | −0.0073 (10) |
C12 | 0.0365 (9) | 0.0641 (11) | 0.0479 (9) | 0.0000 (8) | −0.0004 (7) | −0.0145 (8) |
C13 | 0.0324 (8) | 0.0559 (10) | 0.0381 (8) | −0.0066 (7) | 0.0067 (6) | −0.0090 (7) |
C14 | 0.0497 (11) | 0.0931 (16) | 0.0450 (9) | −0.0254 (11) | 0.0092 (8) | 0.0010 (10) |
C15 | 0.0450 (10) | 0.0741 (13) | 0.0439 (9) | −0.0107 (9) | 0.0128 (8) | 0.0087 (8) |
C16 | 0.0490 (12) | 0.109 (2) | 0.0596 (12) | 0.0017 (12) | 0.0059 (10) | 0.0112 (12) |
C17 | 0.0645 (14) | 0.0874 (17) | 0.0755 (15) | 0.0128 (12) | 0.0221 (12) | 0.0052 (13) |
C18 | 0.0769 (14) | 0.0553 (11) | 0.0510 (10) | −0.0055 (10) | 0.0224 (10) | 0.0059 (8) |
C19 | 0.0628 (12) | 0.0695 (13) | 0.0403 (9) | −0.0056 (10) | 0.0096 (8) | 0.0096 (8) |
C20 | 0.0494 (10) | 0.0688 (12) | 0.0430 (9) | −0.0008 (9) | 0.0129 (8) | 0.0099 (8) |
C21 | 0.0346 (8) | 0.0405 (8) | 0.0298 (6) | 0.0001 (6) | 0.0042 (6) | −0.0018 (6) |
C22 | 0.0425 (9) | 0.0446 (9) | 0.0364 (7) | 0.0015 (7) | −0.0006 (6) | 0.0012 (6) |
C23 | 0.0589 (11) | 0.0393 (9) | 0.0419 (8) | 0.0037 (8) | 0.0041 (8) | 0.0055 (7) |
C24 | 0.0556 (11) | 0.0399 (9) | 0.0506 (9) | −0.0072 (8) | 0.0110 (8) | 0.0014 (7) |
C25 | 0.0421 (9) | 0.0459 (9) | 0.0460 (8) | −0.0057 (7) | 0.0092 (7) | −0.0057 (7) |
C26 | 0.0413 (10) | 0.0681 (13) | 0.0672 (12) | −0.0121 (9) | 0.0057 (9) | 0.0003 (10) |
C27 | 0.0338 (10) | 0.0941 (17) | 0.0767 (14) | −0.0067 (10) | −0.0083 (10) | 0.0053 (12) |
C28 | 0.0440 (10) | 0.0776 (14) | 0.0562 (10) | 0.0042 (9) | −0.0084 (8) | 0.0115 (10) |
C29 | 0.0376 (9) | 0.0563 (10) | 0.0381 (7) | 0.0013 (7) | 0.0005 (6) | 0.0039 (7) |
C30 | 0.0356 (8) | 0.0437 (8) | 0.0343 (7) | 0.0008 (6) | 0.0033 (6) | −0.0030 (6) |
C31 | 0.0435 (9) | 0.0537 (10) | 0.0323 (7) | 0.0024 (7) | 0.0029 (6) | 0.0080 (7) |
C32 | 0.113 (2) | 0.0510 (12) | 0.0757 (14) | −0.0271 (13) | 0.0254 (14) | −0.0013 (10) |
C33 | 0.116 (2) | 0.0512 (12) | 0.0790 (15) | −0.0122 (13) | 0.0249 (14) | −0.0133 (11) |
C34 | 0.0607 (12) | 0.0465 (10) | 0.0459 (9) | 0.0034 (8) | 0.0081 (8) | −0.0041 (7) |
O35 | 0.0501 (8) | 0.1151 (13) | 0.0358 (6) | −0.0034 (8) | −0.0069 (6) | −0.0060 (7) |
O36 | 0.0606 (10) | 0.195 (2) | 0.0676 (10) | −0.0584 (13) | 0.0156 (8) | −0.0300 (12) |
O37 | 0.0631 (9) | 0.0611 (8) | 0.0503 (7) | 0.0028 (6) | 0.0018 (6) | 0.0228 (6) |
Cl1—C18 | 1.747 (2) | C16—H16 | 0.9300 |
N1—C2 | 1.453 (2) | C17—C18 | 1.364 (3) |
N1—C34 | 1.473 (2) | C17—H17 | 0.9300 |
N1—C5 | 1.479 (2) | C18—C19 | 1.362 (3) |
C2—C21 | 1.520 (2) | C19—C20 | 1.383 (3) |
C2—C3 | 1.567 (2) | C19—H19 | 0.9300 |
C2—C31 | 1.585 (2) | C20—H20 | 0.9300 |
C3—C13 | 1.505 (2) | C21—C22 | 1.368 (2) |
C3—C6 | 1.551 (2) | C21—C30 | 1.410 (2) |
C3—C4 | 1.566 (2) | C22—C23 | 1.415 (2) |
C4—C14 | 1.527 (3) | C22—H22 | 0.9300 |
C4—C5 | 1.528 (2) | C23—C24 | 1.359 (3) |
C4—H4 | 0.9800 | C23—H23 | 0.9300 |
C5—C32 | 1.522 (3) | C24—C25 | 1.410 (3) |
C5—H5 | 0.9800 | C24—H24 | 0.9300 |
C6—O35 | 1.214 (2) | C25—C30 | 1.401 (2) |
C6—N7 | 1.348 (3) | C25—C26 | 1.410 (3) |
N7—C8 | 1.398 (2) | C26—C27 | 1.364 (3) |
N7—H7 | 0.8600 | C26—H26 | 0.9300 |
C8—C9 | 1.380 (3) | C27—C28 | 1.404 (3) |
C8—C13 | 1.392 (2) | C27—H27 | 0.9300 |
C9—C10 | 1.385 (3) | C28—C29 | 1.370 (3) |
C9—H9 | 0.9300 | C28—H28 | 0.9300 |
C10—C11 | 1.376 (3) | C29—C30 | 1.406 (2) |
C10—H10 | 0.9300 | C29—C31 | 1.470 (2) |
C11—C12 | 1.385 (3) | C31—O37 | 1.210 (2) |
C11—H11 | 0.9300 | C32—C33 | 1.524 (3) |
C12—C13 | 1.383 (3) | C32—H32A | 0.9700 |
C12—H12 | 0.9300 | C32—H32B | 0.9700 |
C14—O36 | 1.205 (2) | C33—C34 | 1.512 (3) |
C14—C15 | 1.489 (3) | C33—H33A | 0.9700 |
C15—C16 | 1.386 (3) | C33—H33B | 0.9700 |
C15—C20 | 1.386 (3) | C34—H34A | 0.9700 |
C16—C17 | 1.380 (3) | C34—H34B | 0.9700 |
C2—N1—C34 | 118.3 (1) | C16—C17—H17 | 120.6 |
C2—N1—C5 | 110.4 (1) | C19—C18—C17 | 121.9 (2) |
C34—N1—C5 | 109.3 (1) | C19—C18—Cl1 | 118.61 (18) |
N1—C2—C21 | 113.82 (12) | C17—C18—Cl1 | 119.44 (18) |
N1—C2—C3 | 101.82 (12) | C18—C19—C20 | 119.3 (2) |
C21—C2—C3 | 115.89 (13) | C18—C19—H19 | 120.4 |
N1—C2—C31 | 114.61 (13) | C20—C19—H19 | 120.4 |
C21—C2—C31 | 101.49 (12) | C19—C20—C15 | 120.43 (19) |
C3—C2—C31 | 109.70 (12) | C19—C20—H20 | 119.8 |
C13—C3—C6 | 102.26 (14) | C15—C20—H20 | 119.8 |
C13—C3—C4 | 113.24 (14) | C22—C21—C30 | 118.09 (14) |
C6—C3—C4 | 114.60 (13) | C22—C21—C2 | 132.50 (15) |
C13—C3—C2 | 114.65 (12) | C30—C21—C2 | 109.32 (13) |
C6—C3—C2 | 111.87 (13) | C21—C22—C23 | 118.98 (16) |
C4—C3—C2 | 100.77 (13) | C21—C22—H22 | 120.5 |
C14—C4—C5 | 113.15 (15) | C23—C22—H22 | 120.5 |
C14—C4—C3 | 113.86 (17) | C24—C23—C22 | 122.80 (16) |
C5—C4—C3 | 102.79 (13) | C24—C23—H23 | 118.6 |
C14—C4—H4 | 108.9 | C22—C23—H23 | 118.6 |
C5—C4—H4 | 108.9 | C23—C24—C25 | 119.92 (16) |
C3—C4—H4 | 108.9 | C23—C24—H24 | 120.0 |
N1—C5—C32 | 105.20 (16) | C25—C24—H24 | 120.0 |
N1—C5—C4 | 105.95 (14) | C30—C25—C26 | 115.54 (17) |
C32—C5—C4 | 118.12 (18) | C30—C25—C24 | 116.67 (16) |
N1—C5—H5 | 109.1 | C26—C25—C24 | 127.77 (17) |
C32—C5—H5 | 109.1 | C27—C26—C25 | 121.16 (18) |
C4—C5—H5 | 109.1 | C27—C26—H26 | 119.4 |
O35—C6—N7 | 126.40 (17) | C25—C26—H26 | 119.4 |
O35—C6—C3 | 126.58 (19) | C26—C27—C28 | 122.56 (18) |
N7—C6—C3 | 107.02 (15) | C26—C27—H27 | 118.7 |
C6—N7—C8 | 112.9 (1) | C28—C27—H27 | 118.7 |
C6—N7—H7 | 123.6 | C29—C28—C27 | 117.89 (18) |
C8—N7—H7 | 123.6 | C29—C28—H28 | 121.1 |
C9—C8—C13 | 122.1 (2) | C27—C28—H28 | 121.1 |
C9—C8—N7 | 128.78 (17) | C28—C29—C30 | 119.65 (17) |
C13—C8—N7 | 109.12 (17) | C28—C29—C31 | 132.93 (17) |
C8—C9—C10 | 117.4 (2) | C30—C29—C31 | 107.27 (14) |
C8—C9—H9 | 121.3 | C25—C30—C29 | 123.10 (16) |
C10—C9—H9 | 121.3 | C25—C30—C21 | 123.50 (15) |
C11—C10—C9 | 121.5 (2) | C29—C30—C21 | 113.35 (14) |
C11—C10—H10 | 119.2 | O37—C31—C29 | 126.94 (16) |
C9—C10—H10 | 119.2 | O37—C31—C2 | 124.72 (16) |
C10—C11—C12 | 120.5 (2) | C29—C31—C2 | 108.15 (13) |
C10—C11—H11 | 119.7 | C5—C32—C33 | 102.16 (18) |
C12—C11—H11 | 119.7 | C5—C32—H32A | 111.3 |
C13—C12—C11 | 119.1 (2) | C33—C32—H32A | 111.3 |
C13—C12—H12 | 120.4 | C5—C32—H32B | 111.3 |
C11—C12—H12 | 120.4 | C33—C32—H32B | 111.3 |
C12—C13—C8 | 119.33 (17) | H32A—C32—H32B | 109.2 |
C12—C13—C3 | 132.02 (15) | C34—C33—C32 | 103.57 (18) |
C8—C13—C3 | 108.64 (15) | C34—C33—H33A | 111.0 |
O36—C14—C15 | 119.90 (19) | C32—C33—H33A | 111.0 |
O36—C14—C4 | 121.16 (18) | C34—C33—H33B | 111.0 |
C15—C14—C4 | 118.93 (16) | C32—C33—H33B | 111.0 |
C16—C15—C20 | 118.52 (19) | H33A—C33—H33B | 109.0 |
C16—C15—C14 | 118.62 (19) | N1—C34—C33 | 104.80 (16) |
C20—C15—C14 | 122.85 (18) | N1—C34—H34A | 110.8 |
C17—C16—C15 | 121.1 (2) | C33—C34—H34A | 110.8 |
C17—C16—H16 | 119.5 | N1—C34—H34B | 110.8 |
C15—C16—H16 | 119.5 | C33—C34—H34B | 110.8 |
C18—C17—C16 | 118.7 (2) | H34A—C34—H34B | 108.9 |
C18—C17—H17 | 120.6 | ||
C34—N1—C2—C21 | −77.33 (18) | O36—C14—C15—C16 | 32.1 (3) |
C5—N1—C2—C21 | 155.66 (14) | C4—C14—C15—C16 | −146.6 (2) |
C34—N1—C2—C3 | 157.22 (14) | O36—C14—C15—C20 | −148.6 (3) |
C5—N1—C2—C3 | 30.22 (17) | C4—C14—C15—C20 | 32.7 (3) |
C34—N1—C2—C31 | 38.89 (18) | C20—C15—C16—C17 | −1.5 (3) |
C5—N1—C2—C31 | −88.12 (16) | C14—C15—C16—C17 | 177.8 (2) |
N1—C2—C3—C13 | 80.47 (15) | C15—C16—C17—C18 | 1.1 (4) |
C21—C2—C3—C13 | −43.60 (18) | C16—C17—C18—C19 | 0.0 (4) |
C31—C2—C3—C13 | −157.74 (14) | C16—C17—C18—Cl1 | 178.90 (19) |
N1—C2—C3—C6 | −163.68 (14) | C17—C18—C19—C20 | −0.6 (3) |
C21—C2—C3—C6 | 72.25 (18) | Cl1—C18—C19—C20 | −179.49 (15) |
C31—C2—C3—C6 | −41.89 (19) | C18—C19—C20—C15 | 0.1 (3) |
N1—C2—C3—C4 | −41.48 (14) | C16—C15—C20—C19 | 0.9 (3) |
C21—C2—C3—C4 | −165.55 (13) | C14—C15—C20—C19 | −178.39 (19) |
C31—C2—C3—C4 | 80.31 (15) | N1—C2—C21—C22 | −47.8 (2) |
C13—C3—C4—C14 | 37.80 (19) | C3—C2—C21—C22 | 69.7 (2) |
C6—C3—C4—C14 | −78.99 (19) | C31—C2—C21—C22 | −171.50 (16) |
C2—C3—C4—C14 | 160.74 (14) | N1—C2—C21—C30 | 128.53 (14) |
C13—C3—C4—C5 | −84.96 (16) | C3—C2—C21—C30 | −113.88 (14) |
C6—C3—C4—C5 | 158.25 (15) | C31—C2—C21—C30 | 4.87 (15) |
C2—C3—C4—C5 | 37.98 (16) | C30—C21—C22—C23 | 0.4 (2) |
C2—N1—C5—C32 | 119.82 (18) | C2—C21—C22—C23 | 176.50 (15) |
C34—N1—C5—C32 | −12.0 (2) | C21—C22—C23—C24 | 1.1 (3) |
C2—N1—C5—C4 | −6.0 (2) | C22—C23—C24—C25 | −1.0 (3) |
C34—N1—C5—C4 | −137.86 (16) | C23—C24—C25—C30 | −0.5 (2) |
C14—C4—C5—N1 | −144.13 (17) | C23—C24—C25—C26 | −178.92 (19) |
C3—C4—C5—N1 | −20.89 (19) | C30—C25—C26—C27 | −3.1 (3) |
C14—C4—C5—C32 | 98.4 (2) | C24—C25—C26—C27 | 175.3 (2) |
C3—C4—C5—C32 | −138.40 (19) | C25—C26—C27—C28 | 0.7 (4) |
C13—C3—C6—O35 | 178.22 (17) | C26—C27—C28—C29 | 1.4 (4) |
C4—C3—C6—O35 | −58.9 (2) | C27—C28—C29—C30 | −0.9 (3) |
C2—C3—C6—O35 | 55.1 (2) | C27—C28—C29—C31 | −176.0 (2) |
C13—C3—C6—N7 | −1.67 (16) | C26—C25—C30—C29 | 3.6 (2) |
C4—C3—C6—N7 | 121.26 (16) | C24—C25—C30—C29 | −175.00 (15) |
C2—C3—C6—N7 | −124.84 (15) | C26—C25—C30—C21 | −179.36 (16) |
O35—C6—N7—C8 | −179.43 (17) | C24—C25—C30—C21 | 2.0 (2) |
C3—C6—N7—C8 | 0.46 (19) | C28—C29—C30—C25 | −1.7 (3) |
C6—N7—C8—C9 | −178.98 (18) | C31—C29—C30—C25 | 174.57 (15) |
C6—N7—C8—C13 | 1.1 (2) | C28—C29—C30—C21 | −178.97 (16) |
C13—C8—C9—C10 | 1.9 (3) | C31—C29—C30—C21 | −2.74 (19) |
N7—C8—C9—C10 | −178.04 (18) | C22—C21—C30—C25 | −2.0 (2) |
C8—C9—C10—C11 | −0.5 (3) | C2—C21—C30—C25 | −178.95 (14) |
C9—C10—C11—C12 | −1.2 (3) | C22—C21—C30—C29 | 175.32 (14) |
C10—C11—C12—C13 | 1.5 (3) | C2—C21—C30—C29 | −1.65 (18) |
C11—C12—C13—C8 | −0.2 (3) | C28—C29—C31—O37 | 6.2 (3) |
C11—C12—C13—C3 | −179.46 (17) | C30—C29—C31—O37 | −169.34 (17) |
C9—C8—C13—C12 | −1.5 (3) | C28—C29—C31—C2 | −178.67 (19) |
N7—C8—C13—C12 | 178.39 (16) | C30—C29—C31—C2 | 5.81 (18) |
C9—C8—C13—C3 | 177.88 (16) | N1—C2—C31—O37 | 45.7 (2) |
N7—C8—C13—C3 | −2.18 (19) | C21—C2—C31—O37 | 168.84 (16) |
C6—C3—C13—C12 | −178.36 (18) | C3—C2—C31—O37 | −68.1 (2) |
C4—C3—C13—C12 | 57.8 (2) | N1—C2—C31—C29 | −129.57 (14) |
C2—C3—C13—C12 | −57.1 (2) | C21—C2—C31—C29 | −6.45 (16) |
C6—C3—C13—C8 | 2.31 (16) | C3—C2—C31—C29 | 116.65 (14) |
C4—C3—C13—C8 | −121.53 (15) | N1—C5—C32—C33 | 31.2 (2) |
C2—C3—C13—C8 | 123.59 (15) | C4—C5—C32—C33 | 149.1 (2) |
C5—C4—C14—O36 | 0.6 (3) | C5—C32—C33—C34 | −38.7 (3) |
C3—C4—C14—O36 | −116.3 (3) | C2—N1—C34—C33 | −139.96 (17) |
C5—C4—C14—C15 | 179.34 (18) | C5—N1—C34—C33 | −12.4 (2) |
C3—C4—C14—C15 | 62.4 (2) | C32—C33—C34—N1 | 31.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O37 | 0.98 | 2.51 | 3.093 (2) | 118 |
C5—H5···O36 | 0.98 | 2.37 | 2.777 (3) | 104 |
N7—H7···O37i | 0.86 | 2.15 | 2.893 (2) | 144 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |