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
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.179
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C15$ PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C15 PLAT432_ALERT_2_B Short Inter X...Y Contact C15$ .. C15$ = 2.94 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT070_ALERT_1_C Duplicate or Troublesome Atomic Label on Input . C15$ PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C18B PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10B - C11B = 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10B - C12B = 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10A - C11A = 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10A - C12A = 1.44 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 17 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H24 N2 O2
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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) |
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