Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021950/bt6361sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021950/bt6361Isup2.hkl |
CCDC reference: 226964
Data collection: COLLECT (Nonius, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C21H24N2O2 | Z = 4 |
Mr = 336.42 | F(000) = 720 |
Triclinic, P1 | Dx = 1.198 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.642 (1) Å | Cell parameters from 16348 reflections |
b = 12.2348 (11) Å | θ = 2.6–27.5° |
c = 13.5739 (13) Å | µ = 0.08 mm−1 |
α = 104.761 (5)° | T = 150 K |
β = 90.427 (4)° | Plate, colourless |
γ = 93.727 (5)° | 0.35 × 0.30 × 0.05 mm |
V = 1865.1 (3) Å3 |
Nonius KappaCCD diffractometer | 3937 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.100 |
Graphite monochromator | θmax = 27.6°, θmin = 2.6° |
Detector resolution: 9 pixels mm-1 | h = −15→15 |
φ scans and ω scans with κ offsets | k = −15→15 |
20141 measured reflections | l = −17→17 |
8463 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.0702P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
8463 reflections | Δρmax = 0.26 e Å−3 |
456 parameters | Δρmin = −0.30 e Å−3 |
6 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0087 (18) |
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) | |
O1A | 0.63087 (15) | 0.34416 (16) | 0.41158 (13) | 0.0503 (5) | |
O2A | 0.67978 (16) | 0.19217 (15) | 0.46402 (13) | 0.0493 (5) | |
N1A | 0.4473 (2) | 0.8531 (2) | 0.9126 (2) | 0.0728 (8) | |
N2A | 0.5847 (2) | 0.6134 (2) | 1.07078 (19) | 0.0602 (7) | |
C1A | 0.6210 (2) | 0.6322 (2) | 0.82053 (19) | 0.0417 (6) | |
C2A | 0.6176 (2) | 0.6700 (2) | 0.72322 (19) | 0.0480 (7) | |
H2AA | 0.6622 | 0.7435 | 0.7305 | 0.058* | |
H2AB | 0.5376 | 0.6762 | 0.7012 | 0.058* | |
C3A | 0.6747 (2) | 0.5728 (2) | 0.64900 (19) | 0.0445 (7) | |
H3AA | 0.7023 | 0.5903 | 0.5848 | 0.053* | |
C4A | 0.5884 (2) | 0.4691 (2) | 0.63343 (18) | 0.0425 (6) | |
H4AA | 0.5086 | 0.4804 | 0.6122 | 0.051* | |
C5A | 0.6309 (2) | 0.3536 (2) | 0.58707 (19) | 0.0397 (6) | |
C6A | 0.6441 (2) | 0.3254 (2) | 0.67590 (19) | 0.0391 (6) | |
C7A | 0.5992 (2) | 0.4355 (2) | 0.73792 (18) | 0.0389 (6) | |
H7AA | 0.5245 | 0.4266 | 0.7719 | 0.047* | |
C8A | 0.6870 (2) | 0.5277 (2) | 0.80118 (19) | 0.0407 (6) | |
H8AA | 0.7231 | 0.5107 | 0.8622 | 0.049* | |
C9A | 0.7698 (2) | 0.5491 (2) | 0.71847 (19) | 0.0453 (7) | |
H9AA | 0.8253 | 0.6153 | 0.7443 | 0.054* | |
H9AB | 0.8112 | 0.4815 | 0.6857 | 0.054* | |
C10A | 0.5695 (2) | 0.6827 (2) | 0.90694 (19) | 0.0427 (6) | |
C11A | 0.5018 (3) | 0.7786 (3) | 0.9117 (2) | 0.0513 (7) | |
C12A | 0.5779 (2) | 0.6436 (2) | 0.9982 (2) | 0.0455 (7) | |
C13A | 0.6471 (2) | 0.2987 (2) | 0.48004 (19) | 0.0404 (6) | |
C14A | 0.6860 (3) | 0.1280 (2) | 0.3583 (2) | 0.0541 (8) | |
H14A | 0.7441 | 0.0713 | 0.3525 | 0.065* | |
H14B | 0.7101 | 0.1797 | 0.3157 | 0.065* | |
C15A | 0.5704 (3) | 0.0689 (3) | 0.3207 (2) | 0.0651 (9) | |
H15A | 0.5755 | 0.0265 | 0.2493 | 0.098* | |
H15B | 0.5130 | 0.1252 | 0.3262 | 0.098* | |
H15C | 0.5474 | 0.0165 | 0.3621 | 0.098* | |
C16A | 0.6889 (2) | 0.2286 (2) | 0.70913 (18) | 0.0387 (6) | |
H16A | 0.6803 | 0.1603 | 0.6500 | 0.046* | |
C17A | 0.8172 (2) | 0.2512 (2) | 0.7381 (2) | 0.0513 (7) | |
H17A | 0.8605 | 0.2640 | 0.6791 | 0.062* | |
H17B | 0.8287 | 0.3205 | 0.7948 | 0.062* | |
C18A | 0.8636 (2) | 0.1513 (2) | 0.7706 (2) | 0.0537 (8) | |
H18A | 0.8590 | 0.0838 | 0.7117 | 0.064* | |
H18B | 0.9456 | 0.1695 | 0.7920 | 0.064* | |
C19A | 0.7962 (3) | 0.1246 (3) | 0.8575 (2) | 0.0576 (8) | |
H19A | 0.8071 | 0.1892 | 0.9187 | 0.069* | |
H19B | 0.8257 | 0.0572 | 0.8743 | 0.069* | |
C20A | 0.6687 (3) | 0.1019 (3) | 0.8294 (2) | 0.0596 (8) | |
H20A | 0.6259 | 0.0894 | 0.8887 | 0.072* | |
H20B | 0.6570 | 0.0323 | 0.7731 | 0.072* | |
C21A | 0.6219 (2) | 0.2015 (2) | 0.7965 (2) | 0.0506 (7) | |
H21A | 0.5399 | 0.1829 | 0.7752 | 0.061* | |
H21B | 0.6262 | 0.2691 | 0.8552 | 0.061* | |
O1B | 0.86733 (17) | 0.65894 (17) | 0.98421 (14) | 0.0579 (5) | |
O2B | 0.8254 (2) | 0.80794 (16) | 1.11036 (14) | 0.0643 (6) | |
N1B | 1.0636 (3) | 0.1454 (2) | 1.2499 (2) | 0.0797 (9) | |
N2B | 0.9171 (2) | 0.3840 (2) | 1.5130 (2) | 0.0620 (7) | |
C1B | 0.8844 (2) | 0.3615 (2) | 1.2538 (2) | 0.0436 (6) | |
C2B | 0.8895 (3) | 0.3266 (2) | 1.1393 (2) | 0.0527 (7) | |
H2BA | 0.8463 | 0.2527 | 1.1107 | 0.063* | |
H2BB | 0.9700 | 0.3222 | 1.1164 | 0.063* | |
C3B | 0.8316 (3) | 0.4233 (2) | 1.1098 (2) | 0.0508 (7) | |
H3BA | 0.8055 | 0.4066 | 1.0369 | 0.061* | |
C4B | 0.9148 (2) | 0.5289 (2) | 1.14604 (19) | 0.0437 (6) | |
H4BA | 0.9954 | 0.5206 | 1.1215 | 0.052* | |
C5B | 0.8688 (2) | 0.6435 (2) | 1.15400 (19) | 0.0430 (6) | |
C6B | 0.8537 (2) | 0.6681 (2) | 1.25495 (19) | 0.0411 (6) | |
C7B | 0.9018 (2) | 0.5587 (2) | 1.26601 (18) | 0.0397 (6) | |
H7BA | 0.9757 | 0.5688 | 1.3063 | 0.048* | |
C8B | 0.8161 (2) | 0.4639 (2) | 1.2821 (2) | 0.0438 (7) | |
H8BA | 0.7786 | 0.4782 | 1.3498 | 0.053* | |
C9B | 0.7344 (2) | 0.4422 (2) | 1.1875 (2) | 0.0506 (7) | |
H9BA | 0.6808 | 0.3743 | 1.1802 | 0.061* | |
H9BB | 0.6911 | 0.5088 | 1.1859 | 0.061* | |
C10B | 0.9365 (2) | 0.3123 (2) | 1.3188 (2) | 0.0427 (6) | |
C11B | 1.0067 (3) | 0.2188 (3) | 1.2815 (2) | 0.0549 (8) | |
C12B | 0.9262 (2) | 0.3528 (2) | 1.4272 (2) | 0.0465 (7) | |
C13B | 0.8538 (2) | 0.7007 (2) | 1.0737 (2) | 0.0498 (7) | |
C14B | 0.8189 (3) | 0.8767 (3) | 1.0381 (2) | 0.0787 (11) | |
H14C | 0.8970 | 0.8940 | 1.0154 | 0.094* | 0.50 |
H14D | 0.7718 | 0.8349 | 0.9775 | 0.094* | 0.50 |
C15B | 0.7691 (6) | 0.9776 (5) | 1.0849 (5) | 0.0676 (19)* | 0.50 |
H15D | 0.7655 | 1.0249 | 1.0367 | 0.101* | 0.50 |
H15E | 0.8158 | 1.0184 | 1.1449 | 0.101* | 0.50 |
H15F | 0.6911 | 0.9600 | 1.1057 | 0.101* | 0.50 |
H14E | 0.8821 | 0.8611 | 0.9892 | 0.094* | 0.25 |
H14F | 0.7447 | 0.8587 | 0.9993 | 0.094* | 0.25 |
C15* | 0.8281 (10) | 0.9912 (4) | 1.0924 (7) | 0.035 (2)* | 0.25 |
H15G | 0.8261 | 1.0390 | 1.0446 | 0.053* | 0.25 |
H15H | 0.9009 | 1.0079 | 1.1318 | 0.053* | 0.25 |
H15I | 0.7637 | 1.0065 | 1.1389 | 0.053* | 0.25 |
H14G | 0.8279 | 0.8288 | 0.9682 | 0.094* | 0.25 |
H14H | 0.7422 | 0.9079 | 1.0412 | 0.094* | 0.25 |
C15$ | 0.9044 (11) | 0.9660 (10) | 1.0587 (12) | 0.094 (5)* | 0.25 |
H15J | 0.8978 | 1.0109 | 1.0088 | 0.141* | 0.25 |
H15K | 0.9804 | 0.9353 | 1.0544 | 0.141* | 0.25 |
H15L | 0.8949 | 1.0143 | 1.1274 | 0.141* | 0.25 |
C16B | 0.8078 (2) | 0.7632 (2) | 1.33363 (19) | 0.0450 (7) | |
H16B | 0.7899 | 0.8241 | 1.2999 | 0.054* | |
C17B | 0.6969 (3) | 0.7247 (3) | 1.3775 (3) | 0.0729 (10) | |
H17C | 0.6381 | 0.6980 | 1.3221 | 0.087* | |
H17D | 0.7115 | 0.6602 | 1.4065 | 0.087* | |
C18B | 0.6511 (3) | 0.8194 (3) | 1.4600 (3) | 0.0905 (12) | |
H18C | 0.6282 | 0.8801 | 1.4292 | 0.109* | |
H18D | 0.5817 | 0.7897 | 1.4889 | 0.109* | |
C19B | 0.7382 (3) | 0.8683 (3) | 1.5437 (2) | 0.0646 (8) | |
H19C | 0.7544 | 0.8102 | 1.5801 | 0.077* | |
H19D | 0.7067 | 0.9329 | 1.5931 | 0.077* | |
C20B | 0.8490 (3) | 0.9083 (2) | 1.5017 (2) | 0.0573 (8) | |
H20C | 0.9071 | 0.9350 | 1.5577 | 0.069* | |
H20D | 0.8345 | 0.9729 | 1.4728 | 0.069* | |
C21B | 0.8954 (2) | 0.8136 (2) | 1.4196 (2) | 0.0553 (8) | |
H21C | 0.9182 | 0.7531 | 1.4507 | 0.066* | |
H21D | 0.9651 | 0.8435 | 1.3911 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0574 (12) | 0.0539 (12) | 0.0403 (11) | 0.0020 (10) | −0.0037 (9) | 0.0142 (10) |
O2A | 0.0618 (12) | 0.0462 (11) | 0.0381 (10) | 0.0069 (10) | 0.0000 (9) | 0.0064 (9) |
N1A | 0.093 (2) | 0.0675 (18) | 0.0592 (17) | 0.0334 (17) | 0.0031 (15) | 0.0119 (14) |
N2A | 0.0573 (16) | 0.0799 (19) | 0.0493 (15) | 0.0176 (14) | 0.0083 (12) | 0.0239 (14) |
C1A | 0.0413 (15) | 0.0423 (15) | 0.0398 (15) | −0.0040 (12) | −0.0025 (12) | 0.0094 (12) |
C2A | 0.0573 (18) | 0.0455 (16) | 0.0416 (16) | 0.0045 (14) | 0.0024 (13) | 0.0113 (13) |
C3A | 0.0550 (17) | 0.0451 (16) | 0.0352 (14) | 0.0023 (13) | 0.0049 (12) | 0.0137 (13) |
C4A | 0.0441 (15) | 0.0471 (16) | 0.0368 (14) | 0.0045 (13) | −0.0022 (11) | 0.0116 (13) |
C5A | 0.0378 (14) | 0.0414 (15) | 0.0386 (15) | 0.0022 (12) | −0.0019 (11) | 0.0081 (12) |
C6A | 0.0337 (14) | 0.0413 (15) | 0.0415 (15) | −0.0005 (12) | −0.0004 (11) | 0.0100 (12) |
C7A | 0.0380 (14) | 0.0424 (15) | 0.0364 (14) | 0.0000 (12) | −0.0001 (11) | 0.0108 (12) |
C8A | 0.0430 (15) | 0.0432 (15) | 0.0357 (14) | 0.0055 (12) | 0.0015 (11) | 0.0091 (12) |
C9A | 0.0430 (16) | 0.0450 (16) | 0.0447 (16) | −0.0047 (13) | 0.0039 (12) | 0.0076 (13) |
C10A | 0.0442 (16) | 0.0428 (15) | 0.0400 (15) | 0.0067 (13) | −0.0002 (12) | 0.0074 (13) |
C11A | 0.0586 (19) | 0.0523 (18) | 0.0417 (16) | 0.0104 (16) | 0.0024 (13) | 0.0083 (14) |
C12A | 0.0418 (16) | 0.0516 (17) | 0.0426 (16) | 0.0087 (13) | 0.0060 (12) | 0.0097 (14) |
C13A | 0.0370 (14) | 0.0432 (15) | 0.0414 (15) | 0.0011 (12) | −0.0017 (11) | 0.0118 (13) |
C14A | 0.067 (2) | 0.0502 (17) | 0.0391 (16) | 0.0077 (15) | 0.0048 (14) | −0.0013 (14) |
C15A | 0.080 (2) | 0.060 (2) | 0.0473 (18) | −0.0076 (17) | −0.0026 (16) | 0.0027 (15) |
C16A | 0.0399 (15) | 0.0395 (14) | 0.0366 (14) | 0.0060 (12) | 0.0017 (11) | 0.0088 (12) |
C17A | 0.0429 (16) | 0.0502 (17) | 0.0633 (19) | 0.0014 (13) | −0.0039 (13) | 0.0199 (15) |
C18A | 0.0458 (17) | 0.0490 (17) | 0.068 (2) | 0.0038 (14) | −0.0082 (14) | 0.0183 (15) |
C19A | 0.082 (2) | 0.0492 (17) | 0.0408 (16) | 0.0152 (16) | −0.0090 (15) | 0.0075 (14) |
C20A | 0.073 (2) | 0.0584 (19) | 0.0558 (19) | 0.0171 (17) | 0.0235 (16) | 0.0262 (16) |
C21A | 0.0511 (17) | 0.0497 (17) | 0.0552 (18) | 0.0077 (14) | 0.0130 (13) | 0.0194 (15) |
O1B | 0.0724 (14) | 0.0646 (13) | 0.0358 (11) | −0.0059 (11) | 0.0013 (10) | 0.0137 (10) |
O2B | 0.1093 (18) | 0.0435 (12) | 0.0422 (12) | −0.0023 (12) | −0.0111 (11) | 0.0170 (10) |
N1B | 0.098 (2) | 0.0675 (19) | 0.077 (2) | 0.0302 (18) | 0.0071 (17) | 0.0180 (16) |
N2B | 0.0584 (16) | 0.0795 (19) | 0.0520 (17) | 0.0111 (14) | 0.0025 (13) | 0.0221 (15) |
C1B | 0.0397 (15) | 0.0451 (15) | 0.0463 (16) | −0.0039 (13) | 0.0010 (12) | 0.0137 (13) |
C2B | 0.071 (2) | 0.0406 (16) | 0.0440 (16) | 0.0012 (15) | −0.0027 (14) | 0.0069 (13) |
C3B | 0.071 (2) | 0.0426 (16) | 0.0365 (15) | −0.0021 (14) | −0.0115 (14) | 0.0070 (13) |
C4B | 0.0489 (16) | 0.0452 (16) | 0.0356 (14) | −0.0035 (13) | 0.0026 (12) | 0.0092 (13) |
C5B | 0.0526 (17) | 0.0413 (15) | 0.0342 (15) | −0.0027 (13) | −0.0008 (12) | 0.0094 (12) |
C6B | 0.0398 (15) | 0.0428 (15) | 0.0399 (15) | −0.0009 (12) | −0.0011 (11) | 0.0099 (13) |
C7B | 0.0401 (15) | 0.0429 (15) | 0.0350 (14) | 0.0011 (12) | 0.0005 (11) | 0.0086 (12) |
C8B | 0.0424 (15) | 0.0489 (16) | 0.0431 (15) | 0.0054 (13) | 0.0023 (12) | 0.0166 (13) |
C9B | 0.0486 (17) | 0.0522 (17) | 0.0550 (18) | −0.0051 (14) | −0.0101 (14) | 0.0231 (15) |
C10B | 0.0421 (15) | 0.0422 (15) | 0.0445 (16) | 0.0035 (12) | 0.0024 (12) | 0.0119 (13) |
C11B | 0.062 (2) | 0.0505 (18) | 0.0548 (19) | 0.0144 (16) | 0.0040 (15) | 0.0160 (15) |
C12B | 0.0415 (16) | 0.0518 (17) | 0.0497 (18) | 0.0079 (13) | 0.0003 (13) | 0.0183 (15) |
C13B | 0.0586 (18) | 0.0472 (17) | 0.0425 (17) | −0.0084 (14) | −0.0042 (14) | 0.0126 (14) |
C14B | 0.125 (3) | 0.056 (2) | 0.061 (2) | −0.010 (2) | −0.023 (2) | 0.0320 (18) |
C14* | 0.125 (3) | 0.056 (2) | 0.061 (2) | −0.010 (2) | −0.023 (2) | 0.0320 (18) |
C14$ | 0.125 (3) | 0.056 (2) | 0.061 (2) | −0.010 (2) | −0.023 (2) | 0.0320 (18) |
C16B | 0.0532 (17) | 0.0451 (16) | 0.0383 (15) | 0.0080 (13) | −0.0019 (12) | 0.0125 (13) |
C17B | 0.0423 (18) | 0.080 (2) | 0.075 (2) | −0.0031 (17) | 0.0056 (16) | −0.0184 (19) |
C18B | 0.051 (2) | 0.097 (3) | 0.094 (3) | 0.004 (2) | 0.0114 (19) | −0.030 (2) |
C19B | 0.068 (2) | 0.0570 (19) | 0.059 (2) | 0.0035 (17) | 0.0172 (16) | −0.0035 (16) |
C20B | 0.063 (2) | 0.0506 (17) | 0.0511 (18) | 0.0012 (15) | 0.0094 (15) | −0.0006 (15) |
C21B | 0.0482 (17) | 0.0531 (18) | 0.0529 (18) | −0.0036 (14) | 0.0060 (14) | −0.0064 (14) |
O1A—C13A | 1.218 (3) | N1B—C11B | 1.146 (3) |
O2A—C13A | 1.347 (3) | N2B—C12B | 1.137 (3) |
O2A—C14A | 1.455 (3) | C1B—C10B | 1.350 (3) |
N1A—C11A | 1.142 (3) | C1B—C8B | 1.496 (3) |
N2A—C12A | 1.140 (3) | C1B—C2B | 1.505 (4) |
C1A—C10A | 1.344 (3) | C2B—C3B | 1.534 (3) |
C1A—C8A | 1.501 (3) | C2B—H2BA | 0.9900 |
C1A—C2A | 1.508 (3) | C2B—H2BB | 0.9900 |
C2A—C3A | 1.540 (4) | C3B—C4B | 1.536 (4) |
C2A—H2AA | 0.9900 | C3B—C9B | 1.541 (4) |
C2A—H2AB | 0.9900 | C3B—H3BA | 1.0000 |
C3A—C4A | 1.535 (4) | C4B—C5B | 1.511 (4) |
C3A—C9A | 1.539 (3) | C4B—C7B | 1.586 (3) |
C3A—H3AA | 1.0000 | C4B—H4BA | 1.0000 |
C4A—C5A | 1.509 (3) | C5B—C6B | 1.341 (3) |
C4A—C7A | 1.580 (3) | C5B—C13B | 1.453 (3) |
C4A—H4AA | 1.0000 | C6B—C16B | 1.495 (4) |
C5A—C6A | 1.346 (3) | C6B—C7B | 1.525 (3) |
C5A—C13A | 1.456 (3) | C7B—C8B | 1.540 (4) |
C6A—C16A | 1.493 (3) | C7B—H7BA | 1.0000 |
C6A—C7A | 1.522 (3) | C8B—C9B | 1.549 (3) |
C7A—C8A | 1.548 (4) | C8B—H8BA | 1.0000 |
C7A—H7AA | 1.0000 | C9B—H9BA | 0.9900 |
C8A—C9A | 1.547 (4) | C9B—H9BB | 0.9900 |
C8A—H8AA | 1.0000 | C10B—C12B | 1.436 (4) |
C9A—H9AA | 0.9900 | C10B—C11B | 1.437 (4) |
C9A—H9AB | 0.9900 | C14B—C15B | 1.400 (5) |
C10A—C12A | 1.442 (4) | C14B—H14C | 0.9900 |
C10A—C11A | 1.445 (4) | C14B—H14D | 0.9900 |
C14A—C15A | 1.506 (4) | C15B—H15D | 0.9800 |
C14A—H14A | 0.9900 | C15B—H15E | 0.9800 |
C14A—H14B | 0.9900 | C15B—H15F | 0.9800 |
C15A—H15A | 0.9800 | C15*—H15G | 0.9800 |
C15A—H15B | 0.9800 | C15*—H15H | 0.9800 |
C15A—H15C | 0.9800 | C15*—H15I | 0.9800 |
C16A—C21A | 1.519 (3) | C15$—H15J | 0.9800 |
C16A—C17A | 1.531 (3) | C15$—H15K | 0.9800 |
C16A—H16A | 1.0000 | C15$—H15L | 0.9800 |
C17A—C18A | 1.528 (3) | C16B—C21B | 1.522 (4) |
C17A—H17A | 0.9900 | C16B—C17B | 1.523 (4) |
C17A—H17B | 0.9900 | C16B—H16B | 1.0000 |
C18A—C19A | 1.514 (4) | C17B—C18B | 1.519 (4) |
C18A—H18A | 0.9900 | C17B—H17C | 0.9900 |
C18A—H18B | 0.9900 | C17B—H17D | 0.9900 |
C19A—C20A | 1.520 (4) | C18B—C19B | 1.494 (4) |
C19A—H19A | 0.9900 | C18B—H18C | 0.9900 |
C19A—H19B | 0.9900 | C18B—H18D | 0.9900 |
C20A—C21A | 1.531 (3) | C19B—C20B | 1.516 (4) |
C20A—H20A | 0.9900 | C19B—H19C | 0.9900 |
C20A—H20B | 0.9900 | C19B—H19D | 0.9900 |
C21A—H21A | 0.9900 | C20B—C21B | 1.520 (4) |
C21A—H21B | 0.9900 | C20B—H20C | 0.9900 |
O1B—C13B | 1.208 (3) | C20B—H20D | 0.9900 |
O2B—C13B | 1.343 (3) | C21B—H21C | 0.9900 |
O2B—C14B | 1.451 (3) | C21B—H21D | 0.9900 |
C13A—O2A—C14A | 116.46 (19) | C8B—C1B—C2B | 107.6 (2) |
C10A—C1A—C8A | 127.3 (2) | C1B—C2B—C3B | 101.7 (2) |
C10A—C1A—C2A | 124.8 (2) | C1B—C2B—H2BA | 111.4 |
C8A—C1A—C2A | 107.8 (2) | C3B—C2B—H2BA | 111.4 |
C1A—C2A—C3A | 101.3 (2) | C1B—C2B—H2BB | 111.4 |
C1A—C2A—H2AA | 111.5 | C3B—C2B—H2BB | 111.4 |
C3A—C2A—H2AA | 111.5 | H2BA—C2B—H2BB | 109.3 |
C1A—C2A—H2AB | 111.5 | C2B—C3B—C4B | 106.1 (2) |
C3A—C2A—H2AB | 111.5 | C2B—C3B—C9B | 100.2 (2) |
H2AA—C2A—H2AB | 109.3 | C4B—C3B—C9B | 104.1 (2) |
C4A—C3A—C9A | 104.0 (2) | C2B—C3B—H3BA | 114.9 |
C4A—C3A—C2A | 105.6 (2) | C4B—C3B—H3BA | 114.9 |
C9A—C3A—C2A | 100.8 (2) | C9B—C3B—H3BA | 114.9 |
C4A—C3A—H3AA | 114.9 | C5B—C4B—C3B | 118.1 (2) |
C9A—C3A—H3AA | 114.9 | C5B—C4B—C7B | 84.98 (18) |
C2A—C3A—H3AA | 114.9 | C3B—C4B—C7B | 102.3 (2) |
C5A—C4A—C3A | 118.2 (2) | C5B—C4B—H4BA | 115.5 |
C5A—C4A—C7A | 84.86 (17) | C3B—C4B—H4BA | 115.5 |
C3A—C4A—C7A | 102.52 (19) | C7B—C4B—H4BA | 115.5 |
C5A—C4A—H4AA | 115.5 | C6B—C5B—C13B | 135.9 (3) |
C3A—C4A—H4AA | 115.5 | C6B—C5B—C4B | 95.6 (2) |
C7A—C4A—H4AA | 115.5 | C13B—C5B—C4B | 128.4 (2) |
C6A—C5A—C13A | 135.6 (2) | C5B—C6B—C16B | 136.3 (2) |
C6A—C5A—C4A | 95.8 (2) | C5B—C6B—C7B | 93.6 (2) |
C13A—C5A—C4A | 128.6 (2) | C16B—C6B—C7B | 130.1 (2) |
C5A—C6A—C16A | 136.4 (2) | C6B—C7B—C8B | 118.0 (2) |
C5A—C6A—C7A | 93.03 (19) | C6B—C7B—C4B | 85.73 (18) |
C16A—C6A—C7A | 130.6 (2) | C8B—C7B—C4B | 103.5 (2) |
C6A—C7A—C8A | 118.3 (2) | C6B—C7B—H7BA | 115.1 |
C6A—C7A—C4A | 86.26 (18) | C8B—C7B—H7BA | 115.1 |
C8A—C7A—C4A | 103.54 (19) | C4B—C7B—H7BA | 115.1 |
C6A—C7A—H7AA | 114.9 | C1B—C8B—C7B | 102.7 (2) |
C8A—C7A—H7AA | 114.9 | C1B—C8B—C9B | 100.6 (2) |
C4A—C7A—H7AA | 114.9 | C7B—C8B—C9B | 102.4 (2) |
C1A—C8A—C9A | 100.6 (2) | C1B—C8B—H8BA | 116.3 |
C1A—C8A—C7A | 102.48 (19) | C7B—C8B—H8BA | 116.3 |
C9A—C8A—C7A | 102.0 (2) | C9B—C8B—H8BA | 116.3 |
C1A—C8A—H8AA | 116.4 | C3B—C9B—C8B | 94.8 (2) |
C9A—C8A—H8AA | 116.4 | C3B—C9B—H9BA | 112.8 |
C7A—C8A—H8AA | 116.4 | C8B—C9B—H9BA | 112.8 |
C3A—C9A—C8A | 95.0 (2) | C3B—C9B—H9BB | 112.8 |
C3A—C9A—H9AA | 112.7 | C8B—C9B—H9BB | 112.8 |
C8A—C9A—H9AA | 112.7 | H9BA—C9B—H9BB | 110.2 |
C3A—C9A—H9AB | 112.7 | C1B—C10B—C12B | 121.5 (2) |
C8A—C9A—H9AB | 112.7 | C1B—C10B—C11B | 120.7 (2) |
H9AA—C9A—H9AB | 110.2 | C12B—C10B—C11B | 117.8 (2) |
C1A—C10A—C12A | 122.1 (2) | N1B—C11B—C10B | 178.3 (3) |
C1A—C10A—C11A | 120.9 (2) | N2B—C12B—C10B | 179.2 (3) |
C12A—C10A—C11A | 117.0 (2) | O1B—C13B—O2B | 123.1 (2) |
N1A—C11A—C10A | 178.0 (3) | O1B—C13B—C5B | 124.7 (3) |
N2A—C12A—C10A | 179.5 (3) | O2B—C13B—C5B | 112.2 (2) |
O1A—C13A—O2A | 123.3 (2) | C15B—C14B—O2B | 109.1 (4) |
O1A—C13A—C5A | 123.3 (2) | C15B—C14B—H14C | 109.9 |
O2A—C13A—C5A | 113.4 (2) | O2B—C14B—H14C | 109.9 |
O2A—C14A—C15A | 110.2 (2) | C15B—C14B—H14D | 109.9 |
O2A—C14A—H14A | 109.6 | O2B—C14B—H14D | 109.9 |
C15A—C14A—H14A | 109.6 | H14C—C14B—H14D | 108.3 |
O2A—C14A—H14B | 109.6 | C14B—C15B—H15D | 109.5 |
C15A—C14A—H14B | 109.6 | C14B—C15B—H15E | 109.5 |
H14A—C14A—H14B | 108.1 | H15D—C15B—H15E | 109.5 |
C14A—C15A—H15A | 109.5 | C14B—C15B—H15F | 109.5 |
C14A—C15A—H15B | 109.5 | H15D—C15B—H15F | 109.5 |
H15A—C15A—H15B | 109.5 | H15E—C15B—H15F | 109.5 |
C14A—C15A—H15C | 109.5 | H15G—C15*—H15H | 109.5 |
H15A—C15A—H15C | 109.5 | H15G—C15*—H15I | 109.5 |
H15B—C15A—H15C | 109.5 | H15H—C15*—H15I | 109.5 |
C6A—C16A—C21A | 112.4 (2) | H15J—C15$—H15K | 109.5 |
C6A—C16A—C17A | 110.9 (2) | H15J—C15$—H15L | 109.5 |
C21A—C16A—C17A | 110.3 (2) | H15K—C15$—H15L | 109.5 |
C6A—C16A—H16A | 107.7 | C6B—C16B—C21B | 111.8 (2) |
C21A—C16A—H16A | 107.7 | C6B—C16B—C17B | 111.2 (2) |
C17A—C16A—H16A | 107.7 | C21B—C16B—C17B | 109.5 (2) |
C18A—C17A—C16A | 111.0 (2) | C6B—C16B—H16B | 108.0 |
C18A—C17A—H17A | 109.4 | C21B—C16B—H16B | 108.0 |
C16A—C17A—H17A | 109.4 | C17B—C16B—H16B | 108.0 |
C18A—C17A—H17B | 109.4 | C18B—C17B—C16B | 111.9 (3) |
C16A—C17A—H17B | 109.4 | C18B—C17B—H17C | 109.2 |
H17A—C17A—H17B | 108.0 | C16B—C17B—H17C | 109.2 |
C19A—C18A—C17A | 111.5 (2) | C18B—C17B—H17D | 109.2 |
C19A—C18A—H18A | 109.3 | C16B—C17B—H17D | 109.2 |
C17A—C18A—H18A | 109.3 | H17C—C17B—H17D | 107.9 |
C19A—C18A—H18B | 109.3 | C19B—C18B—C17B | 112.2 (3) |
C17A—C18A—H18B | 109.3 | C19B—C18B—H18C | 109.2 |
H18A—C18A—H18B | 108.0 | C17B—C18B—H18C | 109.2 |
C18A—C19A—C20A | 110.9 (2) | C19B—C18B—H18D | 109.2 |
C18A—C19A—H19A | 109.5 | C17B—C18B—H18D | 109.2 |
C20A—C19A—H19A | 109.5 | H18C—C18B—H18D | 107.9 |
C18A—C19A—H19B | 109.5 | C18B—C19B—C20B | 110.9 (3) |
C20A—C19A—H19B | 109.5 | C18B—C19B—H19C | 109.5 |
H19A—C19A—H19B | 108.0 | C20B—C19B—H19C | 109.5 |
C19A—C20A—C21A | 110.9 (2) | C18B—C19B—H19D | 109.5 |
C19A—C20A—H20A | 109.5 | C20B—C19B—H19D | 109.5 |
C21A—C20A—H20A | 109.5 | H19C—C19B—H19D | 108.0 |
C19A—C20A—H20B | 109.5 | C19B—C20B—C21B | 111.1 (3) |
C21A—C20A—H20B | 109.5 | C19B—C20B—H20C | 109.4 |
H20A—C20A—H20B | 108.0 | C21B—C20B—H20C | 109.4 |
C16A—C21A—C20A | 111.7 (2) | C19B—C20B—H20D | 109.4 |
C16A—C21A—H21A | 109.3 | C21B—C20B—H20D | 109.4 |
C20A—C21A—H21A | 109.3 | H20C—C20B—H20D | 108.0 |
C16A—C21A—H21B | 109.3 | C20B—C21B—C16B | 112.5 (2) |
C20A—C21A—H21B | 109.3 | C20B—C21B—H21C | 109.1 |
H21A—C21A—H21B | 107.9 | C16B—C21B—H21C | 109.1 |
C13B—O2B—C14B | 117.0 (2) | C20B—C21B—H21D | 109.1 |
C10B—C1B—C8B | 126.4 (2) | C16B—C21B—H21D | 109.1 |
C10B—C1B—C2B | 126.0 (2) | H21C—C21B—H21D | 107.8 |
C13A—O2A—C14A—C15A | −87.4 (3) | C13B—O2B—C14B—C15$ | −114.0 (8) |
C13B—O2B—C14B—C15B | 169.6 (4) | C7A—C6A—C16A—C17A | −85.1 (3) |
C13B—O2B—C14B—C15* | −159.9 (6) | C7B—C6B—C16B—C17B | −66.3 (4) |