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In the title compound, C32H28N2O·0.5C3H6O, the two axial and two equatorial phenyl substituents are essentially planar. There are no hydrogen-bonded interactions between the two independent mol­ecules in the asymmetric unit. The crystal packing is characterized by C—H...O interactions. The solvent (acetone) mol­ecule in the crystal structure significantly influences the packing, features of which are distinctly different from those of unsolvated 4,8,9,10-tetra­phenyl-1,3-di­aza­adamantan-6-one and its methoxy- and chloro-substituted analogues.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017658/cf6210sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017658/cf6210Isup2.hkl
Contains datablock I

CCDC reference: 200755

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.147
  • Data-to-parameter ratio = 10.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5553
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

4,8,9,10-Tetraphenyl-1,3-diazaadamantan-6-one acetone solvate top
Crystal data top
2C32H28N2O·C3H6OZ = 2
Mr = 971.21F(000) = 1032
Triclinic, P1Dx = 1.223 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 12.6087 (14) ÅCell parameters from 1016 reflections
b = 13.7214 (12) Åθ = 12–31°
c = 17.056 (2) ŵ = 0.58 mm1
α = 92.76 (1)°T = 293 K
β = 103.57 (1)°Needles, colourless
γ = 111.60 (1)°0.34 × 0.26 × 0.12 mm
V = 2637.4 (5) Å3
Data collection top
Siemens SMART CCD
diffractometer
7313 independent reflections
Radiation source: fine-focus sealed tube5907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 8 pixels mm-1θmax = 58.9°, θmin = 2.7°
ω scansh = 1014
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1515
Tmin = 0.853, Tmax = 0.929l = 1818
10907 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.8497P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
7313 reflectionsΔρmax = 0.23 e Å3
668 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (2)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.80037 (15)0.08443 (15)0.38558 (10)0.0480 (5)
C2A0.88221 (18)0.04455 (17)0.43890 (13)0.0457 (5)
H2A10.93100.02930.40780.055*
H2A20.93440.10010.48390.055*
N3A0.82221 (14)0.05093 (14)0.47210 (10)0.0441 (4)
C4A0.74941 (19)0.13547 (18)0.40171 (13)0.0477 (5)
H4A0.80320.13610.36860.057*
C41A0.7051 (2)0.24597 (18)0.42565 (14)0.0520 (6)
C42A0.5903 (3)0.3194 (2)0.39799 (18)0.0771 (8)
H42A0.53290.30100.36470.093*
C43A0.7547 (3)0.3785 (2)0.49576 (19)0.0791 (8)
H43A0.81130.39740.52940.095*
C44A0.6407 (4)0.4505 (2)0.4675 (2)0.0897 (10)
H44A0.61910.51870.48100.108*
C45A0.5591 (4)0.4206 (3)0.4192 (2)0.1013 (11)
H45A0.48090.46890.39990.122*
C46A0.7865 (2)0.2782 (2)0.47475 (17)0.0679 (7)
H46A0.86500.23060.49410.081*
C5A0.65451 (19)0.1024 (2)0.34737 (13)0.0531 (6)
H5A0.60270.15870.30180.064*
C6A0.5833 (2)0.0733 (2)0.39666 (13)0.0524 (6)
O1A0.47528 (14)0.10945 (16)0.37686 (10)0.0709 (5)
C7A0.65949 (19)0.01111 (18)0.46867 (13)0.0483 (5)
H7A0.61090.02700.50050.058*
C8A0.7270 (2)0.11079 (18)0.43228 (13)0.0497 (6)
H8A0.66630.12490.39260.060*
C81A0.7973 (2)0.21226 (18)0.49320 (14)0.0508 (6)
C82A0.7519 (3)0.2383 (2)0.55432 (17)0.0704 (7)
H82A0.68070.19080.56080.084*
C85A0.9639 (3)0.3795 (2)0.53926 (18)0.0755 (8)
H53A1.03630.42670.53440.091*
C84A0.9176 (3)0.4045 (2)0.5985 (2)0.0849 (9)
H84A0.95780.46850.63350.102*
C83A0.8119 (3)0.3347 (3)0.6056 (2)0.0865 (9)
H83A0.77960.35180.64540.104*
C86A0.9044 (2)0.28512 (19)0.48656 (16)0.0608 (7)
H86A0.93660.27010.44600.073*
C9A0.7206 (2)0.00208 (19)0.31543 (13)0.0527 (6)
H9A0.65960.02720.28900.063*
C91A0.7838 (2)0.0094 (2)0.25135 (13)0.0561 (6)
C92A0.7483 (2)0.1037 (2)0.19989 (15)0.0691 (7)
H92A0.68870.16420.20720.083*
C93A0.8005 (3)0.1085 (3)0.13784 (17)0.0827 (9)
H93A0.77600.17230.10390.099*
C94A0.8882 (3)0.0200 (3)0.12592 (18)0.0888 (10)
H94A0.92320.02360.08410.107*
C95A0.9241 (3)0.0739 (3)0.17617 (19)0.0911 (10)
H95A0.98310.13440.16820.109*
C96A0.8725 (3)0.0787 (2)0.23855 (16)0.0737 (8)
H96A0.89800.14260.27260.088*
C10A0.75245 (18)0.02359 (17)0.52255 (12)0.0441 (5)
H10A0.80870.03990.56080.053*
C11A0.70444 (19)0.10593 (17)0.57514 (12)0.0449 (5)
C12A0.5848 (2)0.1600 (2)0.56731 (15)0.0598 (6)
H12A0.52990.14770.52650.072*
C13A0.5447 (3)0.2321 (2)0.61866 (17)0.0680 (7)
H13A0.46370.26780.61180.082*
C14A0.6241 (3)0.2506 (2)0.67929 (17)0.0700 (8)
H14A0.59780.29940.71360.084*
C15A0.7435 (3)0.1963 (2)0.68905 (16)0.0709 (7)
H15A0.79780.20810.73070.085*
C16A0.7838 (2)0.1247 (2)0.63823 (14)0.0594 (6)
H16A0.86490.08860.64610.071*
N1B0.34468 (15)0.74897 (13)0.02138 (10)0.0436 (4)
C2B0.21908 (19)0.68652 (17)0.02756 (13)0.0438 (5)
H2B10.18600.73270.00690.053*
H2B20.17680.66130.08470.053*
N3B0.19843 (15)0.59501 (13)0.01698 (10)0.0420 (4)
C4B0.24574 (18)0.52321 (16)0.01815 (13)0.0430 (5)
H4B0.20700.50820.07690.052*
C41B0.21317 (19)0.41601 (16)0.01159 (12)0.0436 (5)
C42B0.2970 (2)0.37658 (18)0.04646 (15)0.0565 (6)
H42B0.37690.41770.05360.068*
C43B0.2650 (3)0.2779 (2)0.07080 (17)0.0649 (7)
H43B0.32310.25380.09470.078*
C44B0.1483 (3)0.2155 (2)0.05998 (17)0.0669 (7)
H44B0.12660.14890.07630.080*
C45B0.0633 (3)0.2521 (2)0.0248 (2)0.0783 (8)
H45B0.01640.20960.01650.094*
C46B0.0959 (2)0.3517 (2)0.00155 (17)0.0658 (7)
H46B0.03740.37590.02130.079*
C5B0.37971 (19)0.58357 (17)0.00941 (13)0.0443 (5)
H5B0.41260.53710.03120.053*
C6B0.44455 (19)0.62772 (17)0.07873 (14)0.0472 (5)
O1B0.53423 (15)0.61642 (14)0.11460 (11)0.0655 (5)
C7B0.39377 (19)0.69650 (16)0.11585 (13)0.0452 (5)
H7B0.43610.72250.17360.054*
C8B0.4117 (2)0.79056 (16)0.06467 (13)0.0452 (5)
H8B0.49580.82030.06600.054*
C81B0.3843 (2)0.88178 (17)0.09699 (13)0.0492 (6)
C82B0.3590 (3)0.9493 (2)0.04468 (16)0.0726 (8)
H82B0.35330.93540.01040.087*
C83B0.3423 (3)1.0370 (2)0.07313 (18)0.0928 (11)
H83B0.32431.08100.03710.111*
C84B0.3521 (3)1.0595 (2)0.15445 (17)0.0871 (10)
H84B0.34251.11940.17370.104*
C85B0.3762 (3)0.9932 (2)0.20719 (16)0.0715 (8)
H85B0.38171.00770.26220.086*
C86B0.3923 (2)0.90490 (19)0.17877 (14)0.0583 (6)
H86B0.40860.86050.21500.070*
C9B0.3963 (2)0.68192 (17)0.05547 (13)0.0468 (5)
H9B0.48180.72360.04280.056*
C91B0.3500 (2)0.65604 (17)0.14824 (13)0.0489 (6)
C92B0.3551 (2)0.5704 (2)0.19113 (16)0.0635 (7)
H92B0.38500.52570.16280.076*
C93B0.3164 (3)0.5502 (2)0.27532 (16)0.0746 (8)
H93B0.32130.49250.30300.090*
C94B0.2711 (3)0.6145 (2)0.31822 (16)0.0718 (8)
H94B0.24420.60020.37480.086*
C95B0.2655 (3)0.7002 (2)0.27711 (16)0.0708 (7)
H95B0.23440.74390.30590.085*
C96B0.3062 (2)0.7219 (2)0.19267 (15)0.0630 (7)
H96B0.30420.78130.16540.076*
C10B0.25869 (19)0.63749 (17)0.10467 (12)0.0435 (5)
H10B0.23080.69280.11720.052*
C11B0.2202 (2)0.55679 (17)0.16118 (12)0.0465 (5)
C12B0.2962 (2)0.52597 (19)0.21650 (15)0.0592 (6)
H12B0.37680.55410.22020.071*
C13B0.2532 (3)0.4533 (2)0.26676 (17)0.0732 (8)
H13B0.30560.43310.30360.088*
C14B0.1358 (3)0.4110 (2)0.26321 (16)0.0717 (8)
H14B0.10800.36160.29670.086*
C15B0.0595 (3)0.4420 (3)0.20980 (15)0.0787 (9)
H15B0.02070.41480.20740.094*
C16B0.1015 (2)0.5138 (2)0.15952 (15)0.0698 (8)
H16B0.04850.53400.12330.084*
C321.1099 (5)0.3049 (3)0.7543 (3)0.1538 (19)
H32A1.16750.31670.72380.231*
H32B1.14630.30490.81050.231*
H32C1.08030.36020.75030.231*
C331.0110 (3)0.2016 (3)0.7209 (2)0.0932 (10)
C340.9117 (4)0.1685 (4)0.7603 (3)0.1431 (17)
H34A0.85350.10030.73310.215*
H34B0.87590.21960.75640.215*
H34C0.94180.16430.81660.215*
O31.0089 (2)0.1446 (2)0.66400 (16)0.1133 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0396 (10)0.0603 (12)0.0437 (10)0.0179 (9)0.0127 (8)0.0111 (9)
C2A0.0338 (11)0.0536 (13)0.0461 (12)0.0131 (10)0.0112 (10)0.0061 (10)
N3A0.0335 (9)0.0494 (10)0.0442 (10)0.0112 (8)0.0099 (8)0.0044 (8)
C4A0.0368 (12)0.0559 (14)0.0451 (12)0.0107 (10)0.0141 (10)0.0038 (10)
C41A0.0470 (14)0.0561 (14)0.0467 (13)0.0111 (12)0.0180 (11)0.0017 (11)
C42A0.0615 (18)0.0690 (19)0.0736 (18)0.0012 (15)0.0098 (14)0.0027 (15)
C43A0.099 (2)0.0654 (19)0.087 (2)0.0359 (18)0.0431 (18)0.0209 (16)
C44A0.123 (3)0.0529 (17)0.086 (2)0.013 (2)0.053 (2)0.0059 (16)
C45A0.093 (3)0.067 (2)0.101 (3)0.0144 (19)0.026 (2)0.0033 (19)
C46A0.0596 (16)0.0578 (16)0.0846 (19)0.0182 (13)0.0237 (15)0.0149 (14)
C5A0.0371 (12)0.0693 (15)0.0413 (12)0.0098 (11)0.0083 (10)0.0049 (11)
C6A0.0371 (14)0.0712 (16)0.0456 (13)0.0168 (12)0.0101 (10)0.0207 (11)
O1A0.0328 (10)0.1113 (15)0.0572 (10)0.0163 (9)0.0095 (8)0.0187 (10)
C7A0.0377 (12)0.0667 (15)0.0454 (12)0.0227 (11)0.0155 (10)0.0142 (11)
C8A0.0430 (13)0.0661 (15)0.0473 (13)0.0259 (11)0.0163 (10)0.0181 (11)
C81A0.0531 (14)0.0569 (14)0.0514 (13)0.0279 (12)0.0183 (11)0.0161 (11)
C82A0.0668 (17)0.0783 (19)0.0754 (18)0.0296 (15)0.0346 (15)0.0108 (15)
C85A0.085 (2)0.0526 (16)0.091 (2)0.0195 (15)0.0394 (17)0.0092 (15)
C84A0.100 (2)0.0642 (18)0.091 (2)0.0261 (18)0.0400 (19)0.0029 (16)
C83A0.100 (2)0.083 (2)0.088 (2)0.0356 (19)0.0483 (19)0.0025 (17)
C86A0.0702 (17)0.0555 (15)0.0658 (16)0.0252 (14)0.0329 (14)0.0145 (13)
C9A0.0413 (13)0.0706 (16)0.0427 (12)0.0185 (12)0.0101 (10)0.0115 (11)
C91A0.0499 (14)0.0765 (17)0.0387 (12)0.0206 (13)0.0127 (11)0.0113 (12)
C92A0.0648 (17)0.0815 (19)0.0473 (14)0.0129 (14)0.0170 (13)0.0042 (14)
C93A0.090 (2)0.097 (2)0.0521 (16)0.0264 (19)0.0220 (15)0.0021 (15)
C94A0.089 (2)0.120 (3)0.0575 (17)0.029 (2)0.0397 (17)0.0044 (18)
C95A0.086 (2)0.106 (3)0.0690 (19)0.0107 (19)0.0434 (17)0.0123 (18)
C96A0.0721 (18)0.0819 (19)0.0601 (16)0.0135 (15)0.0321 (14)0.0103 (14)
C10A0.0364 (12)0.0513 (13)0.0413 (11)0.0146 (10)0.0092 (9)0.0050 (10)
C11A0.0469 (13)0.0484 (13)0.0382 (11)0.0169 (11)0.0128 (10)0.0041 (10)
C12A0.0533 (15)0.0726 (17)0.0532 (14)0.0216 (13)0.0176 (12)0.0163 (12)
C13A0.0671 (17)0.0669 (17)0.0682 (17)0.0151 (14)0.0322 (15)0.0156 (14)
C14A0.100 (2)0.0567 (16)0.0633 (17)0.0298 (16)0.0408 (17)0.0193 (13)
C15A0.086 (2)0.0759 (18)0.0584 (16)0.0396 (17)0.0182 (15)0.0234 (14)
C16A0.0577 (15)0.0662 (16)0.0550 (14)0.0257 (13)0.0129 (12)0.0154 (12)
N1B0.0453 (11)0.0442 (10)0.0428 (10)0.0214 (8)0.0089 (8)0.0039 (8)
C2B0.0455 (13)0.0480 (12)0.0412 (11)0.0246 (10)0.0072 (10)0.0073 (10)
N3B0.0426 (10)0.0477 (10)0.0386 (9)0.0241 (8)0.0062 (8)0.0051 (8)
C4B0.0440 (12)0.0441 (12)0.0419 (11)0.0200 (10)0.0094 (10)0.0043 (9)
C41B0.0496 (13)0.0425 (12)0.0418 (12)0.0205 (11)0.0138 (10)0.0049 (9)
C42B0.0573 (15)0.0478 (14)0.0709 (16)0.0276 (12)0.0179 (12)0.0086 (12)
C43B0.0763 (19)0.0552 (15)0.0801 (18)0.0397 (15)0.0276 (15)0.0173 (13)
C44B0.090 (2)0.0526 (15)0.0798 (18)0.0369 (15)0.0450 (16)0.0247 (13)
C45B0.0641 (18)0.0659 (18)0.112 (2)0.0232 (15)0.0362 (17)0.0343 (17)
C46B0.0534 (16)0.0625 (16)0.0843 (18)0.0253 (13)0.0163 (14)0.0264 (14)
C5B0.0450 (12)0.0441 (12)0.0504 (13)0.0232 (10)0.0155 (10)0.0059 (10)
C6B0.0412 (13)0.0422 (12)0.0584 (14)0.0184 (10)0.0097 (11)0.0109 (10)
O1B0.0503 (10)0.0707 (11)0.0765 (11)0.0353 (9)0.0008 (9)0.0070 (9)
C7B0.0453 (13)0.0454 (12)0.0418 (12)0.0205 (10)0.0027 (10)0.0018 (10)
C8B0.0431 (12)0.0435 (12)0.0465 (12)0.0180 (10)0.0062 (10)0.0040 (10)
C81B0.0552 (14)0.0401 (12)0.0488 (13)0.0197 (11)0.0068 (11)0.0026 (10)
C82B0.123 (3)0.0555 (15)0.0499 (14)0.0480 (17)0.0208 (15)0.0090 (12)
C83B0.167 (3)0.0713 (19)0.0636 (18)0.077 (2)0.0237 (19)0.0158 (15)
C84B0.149 (3)0.0666 (18)0.0651 (18)0.067 (2)0.0255 (19)0.0029 (15)
C85B0.104 (2)0.0657 (17)0.0494 (14)0.0448 (16)0.0120 (14)0.0023 (13)
C86B0.0720 (17)0.0535 (14)0.0485 (14)0.0315 (13)0.0044 (12)0.0027 (11)
C9B0.0445 (13)0.0463 (12)0.0523 (13)0.0198 (10)0.0148 (10)0.0061 (10)
C91B0.0521 (14)0.0466 (13)0.0495 (13)0.0172 (11)0.0205 (11)0.0073 (11)
C92B0.0793 (18)0.0579 (15)0.0608 (16)0.0312 (14)0.0260 (14)0.0081 (12)
C93B0.104 (2)0.0602 (16)0.0591 (17)0.0263 (16)0.0324 (16)0.0031 (13)
C94B0.088 (2)0.0705 (18)0.0486 (15)0.0169 (16)0.0254 (14)0.0084 (14)
C95B0.089 (2)0.0742 (18)0.0562 (16)0.0336 (16)0.0266 (14)0.0228 (14)
C96B0.0874 (19)0.0583 (15)0.0530 (15)0.0336 (14)0.0270 (13)0.0154 (12)
C10B0.0475 (13)0.0472 (12)0.0402 (11)0.0269 (10)0.0068 (10)0.0032 (9)
C11B0.0527 (14)0.0497 (13)0.0376 (11)0.0243 (11)0.0070 (10)0.0015 (10)
C12B0.0594 (16)0.0595 (15)0.0615 (15)0.0295 (13)0.0104 (12)0.0151 (12)
C13B0.086 (2)0.0698 (18)0.0683 (17)0.0387 (16)0.0122 (15)0.0270 (14)
C14B0.089 (2)0.0613 (16)0.0529 (16)0.0161 (15)0.0193 (15)0.0095 (13)
C15B0.0626 (18)0.108 (2)0.0469 (15)0.0113 (16)0.0156 (13)0.0136 (15)
C16B0.0560 (16)0.105 (2)0.0473 (14)0.0308 (15)0.0117 (12)0.0243 (14)
C320.154 (4)0.091 (3)0.159 (4)0.014 (3)0.003 (3)0.001 (3)
C330.094 (3)0.090 (2)0.082 (2)0.029 (2)0.0125 (19)0.0038 (19)
C340.146 (4)0.167 (4)0.131 (4)0.060 (3)0.069 (3)0.023 (3)
O30.0862 (16)0.130 (2)0.1020 (18)0.0257 (15)0.0197 (14)0.0175 (16)
Geometric parameters (Å, º) top
N1A—C8A1.478 (3)C2B—H2B20.970
N1A—C9A1.479 (3)N3B—C10B1.487 (3)
N1A—C2A1.488 (3)N3B—C4B1.493 (3)
C2A—N3A1.467 (3)C4B—C41B1.521 (3)
C2A—H2A10.970C4B—C5B1.550 (3)
C2A—H2A20.970C4B—H4B0.980
N3A—C4A1.481 (3)C41B—C46B1.378 (3)
N3A—C10A1.491 (3)C41B—C42B1.386 (3)
C4A—C41A1.524 (3)C42B—C43B1.378 (3)
C4A—C5A1.555 (3)C42B—H42B0.930
C4A—H4A0.980C43B—C44B1.365 (4)
C41A—C42A1.376 (3)C43B—H43B0.930
C41A—C46A1.384 (4)C44B—C45B1.372 (4)
C42A—C45A1.387 (4)C44B—H44B0.930
C42A—H42A0.930C45B—C46B1.382 (4)
C43A—C44A1.363 (5)C45B—H45B0.930
C43A—C46A1.376 (4)C46B—H46B0.930
C43A—H43A0.930C5B—C6B1.506 (3)
C44A—C45A1.362 (5)C5B—C9B1.566 (3)
C44A—H44A0.930C5B—H5B0.980
C45A—H45A0.930C6B—O1B1.221 (2)
C46A—H46A0.930C6B—C7B1.510 (3)
C5A—C6A1.502 (3)C7B—C10B1.553 (3)
C5A—C9A1.566 (3)C7B—C8B1.570 (3)
C5A—H5A0.980C7B—H7B0.980
C6A—O1A1.219 (3)C8B—C81B1.527 (3)
C6A—C7A1.504 (3)C8B—H8B0.980
C7A—C10A1.547 (3)C81B—C82B1.386 (3)
C7A—C8A1.566 (3)C81B—C86B1.387 (3)
C7A—H7A0.980C82B—C83B1.381 (4)
C8A—C81A1.524 (3)C82B—H82B0.930
C8A—H8A0.980C83B—C84B1.373 (4)
C81A—C86A1.387 (3)C83B—H83B0.930
C81A—C82A1.392 (3)C84B—C85B1.372 (4)
C82A—C83A1.389 (4)C84B—H84B0.930
C82A—H82A0.930C85B—C86B1.384 (3)
C85A—C84A1.367 (4)C85B—H85B0.930
C85A—C86A1.380 (4)C86B—H86B0.930
C85A—H53A0.930C9B—C91B1.526 (3)
C84A—C83A1.363 (4)C9B—H9B0.980
C84A—H84A0.930C91B—C92B1.384 (3)
C83A—H83A0.930C91B—C96B1.390 (3)
C86A—H86A0.930C92B—C93B1.382 (4)
C9A—C91A1.530 (3)C92B—H92B0.930
C9A—H9A0.980C93B—C94B1.371 (4)
C91A—C96A1.380 (4)C93B—H93B0.930
C91A—C92A1.386 (4)C94B—C95B1.372 (4)
C92A—C93A1.383 (4)C94B—H94B0.930
C92A—H92A0.930C95B—C96B1.388 (4)
C93A—C94A1.371 (4)C95B—H95B0.930
C93A—H93A0.930C96B—H96B0.930
C94A—C95A1.373 (5)C10B—C11B1.522 (3)
C94A—H94A0.930C10B—H10B0.980
C95A—C96A1.381 (4)C11B—C12B1.378 (3)
C95A—H95A0.930C11B—C16B1.385 (3)
C96A—H96A0.930C12B—C13B1.388 (4)
C10A—C11A1.515 (3)C12B—H12B0.930
C10A—H10A0.980C13B—C14B1.361 (4)
C11A—C12A1.384 (3)C13B—H13B0.930
C11A—C16A1.392 (3)C14B—C15B1.366 (4)
C12A—C13A1.388 (3)C14B—H14B0.930
C12A—H12A0.930C15B—C16B1.377 (4)
C13A—C14A1.365 (4)C15B—H15B0.930
C13A—H13A0.930C16B—H16B0.930
C14A—C15A1.377 (4)C32—C331.475 (5)
C14A—H14A0.930C32—H32A0.960
C15A—C16A1.377 (4)C32—H32B0.960
C15A—H15A0.930C32—H32C0.960
C16A—H16A0.930C33—O31.206 (4)
N1B—C2B1.472 (3)C33—C341.493 (5)
N1B—C9B1.475 (3)C34—H34A0.960
N1B—C8B1.475 (3)C34—H34B0.960
C2B—N3B1.472 (3)C34—H34C0.960
C2B—H2B10.970
C8A—N1A—C9A108.40 (17)H2B1—C2B—H2B2107.6
C8A—N1A—C2A109.71 (16)C2B—N3B—C10B106.97 (16)
C9A—N1A—C2A110.15 (18)C2B—N3B—C4B107.61 (15)
N3A—C2A—N1A114.15 (16)C10B—N3B—C4B113.48 (15)
N3A—C2A—H2A1108.7N3B—C4B—C41B114.09 (17)
N1A—C2A—H2A1108.7N3B—C4B—C5B109.72 (16)
N3A—C2A—H2A2108.7C41B—C4B—C5B114.91 (17)
N1A—C2A—H2A2108.7N3B—C4B—H4B105.8
H2A1—C2A—H2A2107.6C41B—C4B—H4B105.8
C2A—N3A—C4A106.94 (16)C5B—C4B—H4B105.8
C2A—N3A—C10A107.43 (16)C46B—C41B—C42B117.1 (2)
C4A—N3A—C10A114.13 (16)C46B—C41B—C4B120.13 (19)
N3A—C4A—C41A113.40 (17)C42B—C41B—C4B122.8 (2)
N3A—C4A—C5A109.38 (18)C43B—C42B—C41B121.6 (2)
C41A—C4A—C5A116.49 (19)C43B—C42B—H42B119.2
N3A—C4A—H4A105.5C41B—C42B—H42B119.2
C41A—C4A—H4A105.5C44B—C43B—C42B120.3 (2)
C5A—C4A—H4A105.5C44B—C43B—H43B119.9
C42A—C41A—C46A116.9 (2)C42B—C43B—H43B119.9
C42A—C41A—C4A124.6 (2)C43B—C44B—C45B119.3 (2)
C46A—C41A—C4A118.4 (2)C43B—C44B—H44B120.3
C41A—C42A—C45A120.8 (3)C45B—C44B—H44B120.3
C41A—C42A—H42A119.6C44B—C45B—C46B120.2 (3)
C45A—C42A—H42A119.6C44B—C45B—H45B119.9
C44A—C43A—C46A120.5 (3)C46B—C45B—H45B119.9
C44A—C43A—H43A119.8C41B—C46B—C45B121.4 (2)
C46A—C43A—H43A119.8C41B—C46B—H46B119.3
C45A—C44A—C43A118.6 (3)C45B—C46B—H46B119.3
C45A—C44A—H44A120.7C6B—C5B—C4B109.85 (17)
C43A—C44A—H44A120.7C6B—C5B—C9B105.83 (17)
C44A—C45A—C42A121.3 (3)C4B—C5B—C9B108.66 (17)
C44A—C45A—H45A119.3C6B—C5B—H5B110.8
C42A—C45A—H45A119.3C4B—C5B—H5B110.8
C43A—C46A—C41A121.9 (3)C9B—C5B—H5B110.8
C43A—C46A—H46A119.0O1B—C6B—C5B123.8 (2)
C41A—C46A—H46A119.0O1B—C6B—C7B123.3 (2)
C6A—C5A—C4A111.14 (18)C5B—C6B—C7B112.68 (18)
C6A—C5A—C9A105.02 (19)C6B—C7B—C10B111.64 (17)
C4A—C5A—C9A108.04 (18)C6B—C7B—C8B104.21 (17)
C6A—C5A—H5A110.8C10B—C7B—C8B107.88 (16)
C4A—C5A—H5A110.8C6B—C7B—H7B111.0
C9A—C5A—H5A110.8C10B—C7B—H7B111.0
O1A—C6A—C5A123.1 (2)C8B—C7B—H7B111.0
O1A—C6A—C7A124.0 (2)N1B—C8B—C81B111.35 (17)
C5A—C6A—C7A112.72 (19)N1B—C8B—C7B109.53 (16)
C6A—C7A—C10A110.22 (19)C81B—C8B—C7B115.56 (18)
C6A—C7A—C8A105.78 (17)N1B—C8B—H8B106.6
C10A—C7A—C8A108.09 (17)C81B—C8B—H8B106.6
C6A—C7A—H7A110.9C7B—C8B—H8B106.6
C10A—C7A—H7A110.9C82B—C81B—C86B118.0 (2)
C8A—C7A—H7A110.9C82B—C81B—C8B119.5 (2)
N1A—C8A—C81A112.32 (18)C86B—C81B—C8B122.3 (2)
N1A—C8A—C7A109.44 (18)C83B—C82B—C81B121.0 (2)
C81A—C8A—C7A115.45 (18)C83B—C82B—H82B119.5
N1A—C8A—H8A106.3C81B—C82B—H82B119.5
C81A—C8A—H8A106.3C84B—C83B—C82B120.2 (3)
C7A—C8A—H8A106.3C84B—C83B—H83B119.9
C86A—C81A—C82A117.6 (2)C82B—C83B—H83B119.9
C86A—C81A—C8A121.5 (2)C85B—C84B—C83B119.7 (2)
C82A—C81A—C8A120.7 (2)C85B—C84B—H84B120.1
C83A—C82A—C81A120.5 (3)C83B—C84B—H84B120.1
C83A—C82A—H82A119.7C84B—C85B—C86B120.2 (2)
C81A—C82A—H82A119.7C84B—C85B—H85B119.9
C84A—C85A—C86A120.8 (3)C86B—C85B—H85B119.9
C84A—C85A—H53A119.6C85B—C86B—C81B120.9 (2)
C86A—C85A—H53A119.6C85B—C86B—H86B119.6
C83A—C84A—C85A119.3 (3)C81B—C86B—H86B119.6
C83A—C84A—H84A120.3N1B—C9B—C91B111.79 (17)
C85A—C84A—H84A120.3N1B—C9B—C5B108.93 (16)
C84A—C83A—C82A120.8 (3)C91B—C9B—C5B115.21 (18)
C84A—C83A—H83A119.6N1B—C9B—H9B106.8
C82A—C83A—H83A119.6C91B—C9B—H9B106.8
C85A—C86A—C81A120.9 (2)C5B—C9B—H9B106.8
C85A—C86A—H86A119.5C92B—C91B—C96B117.8 (2)
C81A—C86A—H86A119.5C92B—C91B—C9B121.9 (2)
N1A—C9A—C91A112.21 (18)C96B—C91B—C9B120.3 (2)
N1A—C9A—C5A109.41 (17)C93B—C92B—C91B121.1 (2)
C91A—C9A—C5A116.0 (2)C93B—C92B—H92B119.4
N1A—C9A—H9A106.2C91B—C92B—H92B119.4
C91A—C9A—H9A106.2C94B—C93B—C92B120.4 (3)
C5A—C9A—H9A106.2C94B—C93B—H93B119.8
C96A—C91A—C92A118.0 (2)C92B—C93B—H93B119.8
C96A—C91A—C9A119.5 (2)C93B—C94B—C95B119.6 (2)
C92A—C91A—C9A122.3 (2)C93B—C94B—H94B120.2
C93A—C92A—C91A120.7 (3)C95B—C94B—H94B120.2
C93A—C92A—H92A119.7C94B—C95B—C96B120.2 (3)
C91A—C92A—H92A119.7C94B—C95B—H95B119.9
C94A—C93A—C92A120.5 (3)C96B—C95B—H95B119.9
C94A—C93A—H93A119.7C95B—C96B—C91B120.9 (2)
C92A—C93A—H93A119.7C95B—C96B—H96B119.6
C93A—C94A—C95A119.5 (3)C91B—C96B—H96B119.6
C93A—C94A—H94A120.3N3B—C10B—C11B113.23 (17)
C95A—C94A—H94A120.3N3B—C10B—C7B109.33 (16)
C94A—C95A—C96A120.1 (3)C11B—C10B—C7B117.50 (17)
C94A—C95A—H95A120.0N3B—C10B—H10B105.2
C96A—C95A—H95A120.0C11B—C10B—H10B105.2
C91A—C96A—C95A121.3 (3)C7B—C10B—H10B105.2
C91A—C96A—H96A119.4C12B—C11B—C16B117.2 (2)
C95A—C96A—H96A119.4C12B—C11B—C10B124.5 (2)
N3A—C10A—C11A114.48 (17)C16B—C11B—C10B118.25 (19)
N3A—C10A—C7A109.74 (16)C11B—C12B—C13B120.4 (2)
C11A—C10A—C7A114.95 (17)C11B—C12B—H12B119.8
N3A—C10A—H10A105.6C13B—C12B—H12B119.8
C11A—C10A—H10A105.6C14B—C13B—C12B121.3 (2)
C7A—C10A—H10A105.6C14B—C13B—H13B119.4
C12A—C11A—C16A117.3 (2)C12B—C13B—H13B119.4
C12A—C11A—C10A123.7 (2)C13B—C14B—C15B119.1 (3)
C16A—C11A—C10A119.0 (2)C13B—C14B—H14B120.4
C11A—C12A—C13A121.8 (2)C15B—C14B—H14B120.4
C11A—C12A—H12A119.1C14B—C15B—C16B119.9 (3)
C13A—C12A—H12A119.1C14B—C15B—H15B120.1
C14A—C13A—C12A119.9 (3)C16B—C15B—H15B120.1
C14A—C13A—H13A120.0C15B—C16B—C11B122.1 (2)
C12A—C13A—H13A120.0C15B—C16B—H16B119.0
C13A—C14A—C15A119.2 (2)C11B—C16B—H16B119.0
C13A—C14A—H14A120.4C33—C32—H32A109.5
C15A—C14A—H14A120.4C33—C32—H32B109.5
C16A—C15A—C14A121.1 (3)H32A—C32—H32B109.5
C16A—C15A—H15A119.4C33—C32—H32C109.5
C14A—C15A—H15A119.4H32A—C32—H32C109.5
C15A—C16A—C11A120.7 (2)H32B—C32—H32C109.5
C15A—C16A—H16A119.7O3—C33—C32122.1 (4)
C11A—C16A—H16A119.7O3—C33—C34120.2 (4)
C2B—N1B—C9B109.95 (16)C32—C33—C34117.7 (4)
C2B—N1B—C8B110.29 (16)C33—C34—H34A109.5
C9B—N1B—C8B108.95 (16)C33—C34—H34B109.5
N3B—C2B—N1B114.40 (16)H34A—C34—H34B109.5
N3B—C2B—H2B1108.7C33—C34—H34C109.5
N1B—C2B—H2B1108.7H34A—C34—H34C109.5
N3B—C2B—H2B2108.7H34B—C34—H34C109.5
N1B—C2B—H2B2108.7
C8A—N1A—C2A—N3A59.9 (2)C9B—N1B—C2B—N3B60.7 (2)
C9A—N1A—C2A—N3A59.4 (2)C8B—N1B—C2B—N3B59.5 (2)
N1A—C2A—N3A—C4A61.9 (2)N1B—C2B—N3B—C10B61.6 (2)
N1A—C2A—N3A—C10A61.0 (2)N1B—C2B—N3B—C4B60.6 (2)
C2A—N3A—C4A—C41A166.01 (17)C2B—N3B—C4B—C41B170.39 (17)
C10A—N3A—C4A—C41A75.3 (2)C10B—N3B—C4B—C41B71.5 (2)
C2A—N3A—C4A—C5A62.1 (2)C2B—N3B—C4B—C5B59.0 (2)
C10A—N3A—C4A—C5A56.5 (2)C10B—N3B—C4B—C5B59.1 (2)
N3A—C4A—C41A—C42A133.1 (2)N3B—C4B—C41B—C46B56.7 (3)
C5A—C4A—C41A—C42A4.8 (3)C5B—C4B—C41B—C46B175.3 (2)
N3A—C4A—C41A—C46A51.0 (3)N3B—C4B—C41B—C42B125.9 (2)
C5A—C4A—C41A—C46A179.3 (2)C5B—C4B—C41B—C42B2.1 (3)
C46A—C41A—C42A—C45A0.2 (4)C46B—C41B—C42B—C43B0.6 (3)
C4A—C41A—C42A—C45A176.2 (3)C4B—C41B—C42B—C43B178.1 (2)
C46A—C43A—C44A—C45A0.8 (5)C41B—C42B—C43B—C44B0.9 (4)
C43A—C44A—C45A—C42A0.5 (5)C42B—C43B—C44B—C45B0.1 (4)
C41A—C42A—C45A—C44A0.2 (5)C43B—C44B—C45B—C46B0.9 (4)
C44A—C43A—C46A—C41A0.8 (4)C42B—C41B—C46B—C45B0.4 (4)
C42A—C41A—C46A—C43A0.5 (4)C4B—C41B—C46B—C45B177.2 (2)
C4A—C41A—C46A—C43A176.7 (2)C44B—C45B—C46B—C41B1.2 (4)
N3A—C4A—C5A—C6A53.5 (2)N3B—C4B—C5B—C6B56.1 (2)
C41A—C4A—C5A—C6A76.7 (2)C41B—C4B—C5B—C6B74.0 (2)
N3A—C4A—C5A—C9A61.2 (2)N3B—C4B—C5B—C9B59.3 (2)
C41A—C4A—C5A—C9A168.55 (18)C41B—C4B—C5B—C9B170.61 (17)
C4A—C5A—C6A—O1A129.8 (2)C4B—C5B—C6B—O1B130.6 (2)
C9A—C5A—C6A—O1A113.7 (2)C9B—C5B—C6B—O1B112.3 (2)
C4A—C5A—C6A—C7A54.8 (3)C4B—C5B—C6B—C7B55.0 (2)
C9A—C5A—C6A—C7A61.8 (2)C9B—C5B—C6B—C7B62.1 (2)
O1A—C6A—C7A—C10A129.3 (2)O1B—C6B—C7B—C10B131.5 (2)
C5A—C6A—C7A—C10A55.3 (2)C5B—C6B—C7B—C10B54.1 (2)
O1A—C6A—C7A—C8A114.1 (2)O1B—C6B—C7B—C8B112.3 (2)
C5A—C6A—C7A—C8A61.3 (2)C5B—C6B—C7B—C8B62.1 (2)
C9A—N1A—C8A—C81A166.26 (17)C2B—N1B—C8B—C81B73.8 (2)
C2A—N1A—C8A—C81A73.4 (2)C9B—N1B—C8B—C81B165.41 (17)
C9A—N1A—C8A—C7A64.1 (2)C2B—N1B—C8B—C7B55.2 (2)
C2A—N1A—C8A—C7A56.2 (2)C9B—N1B—C8B—C7B65.5 (2)
C6A—C7A—C8A—N1A60.4 (2)C6B—C7B—C8B—N1B61.8 (2)
C10A—C7A—C8A—N1A57.7 (2)C10B—C7B—C8B—N1B57.0 (2)
C6A—C7A—C8A—C81A171.76 (18)C6B—C7B—C8B—C81B171.47 (18)
C10A—C7A—C8A—C81A70.2 (2)C10B—C7B—C8B—C81B69.8 (2)
N1A—C8A—C81A—C86A18.1 (3)N1B—C8B—C81B—C82B32.9 (3)
C7A—C8A—C81A—C86A144.6 (2)C7B—C8B—C81B—C82B158.7 (2)
N1A—C8A—C81A—C82A166.3 (2)N1B—C8B—C81B—C86B152.1 (2)
C7A—C8A—C81A—C82A39.9 (3)C7B—C8B—C81B—C86B26.3 (3)
C86A—C81A—C82A—C83A0.8 (4)C86B—C81B—C82B—C83B0.0 (4)
C8A—C81A—C82A—C83A174.9 (3)C8B—C81B—C82B—C83B175.3 (3)
C86A—C85A—C84A—C83A0.5 (5)C81B—C82B—C83B—C84B0.9 (6)
C85A—C84A—C83A—C82A0.8 (5)C82B—C83B—C84B—C85B1.4 (6)
C81A—C82A—C83A—C84A1.5 (5)C83B—C84B—C85B—C86B1.0 (5)
C84A—C85A—C86A—C81A1.2 (4)C84B—C85B—C86B—C81B0.1 (4)
C82A—C81A—C86A—C85A0.5 (4)C82B—C81B—C86B—C85B0.4 (4)
C8A—C81A—C86A—C85A176.2 (2)C8B—C81B—C86B—C85B174.7 (2)
C8A—N1A—C9A—C91A164.72 (18)C2B—N1B—C9B—C91B71.6 (2)
C2A—N1A—C9A—C91A75.2 (2)C8B—N1B—C9B—C91B167.44 (17)
C8A—N1A—C9A—C5A65.1 (2)C2B—N1B—C9B—C5B56.9 (2)
C2A—N1A—C9A—C5A54.9 (2)C8B—N1B—C9B—C5B64.1 (2)
C6A—C5A—C9A—N1A61.8 (2)C6B—C5B—C9B—N1B60.4 (2)
C4A—C5A—C9A—N1A56.9 (2)C4B—C5B—C9B—N1B57.5 (2)
C6A—C5A—C9A—C91A170.07 (18)C6B—C5B—C9B—C91B173.09 (18)
C4A—C5A—C9A—C91A71.2 (2)C4B—C5B—C9B—C91B69.0 (2)
N1A—C9A—C91A—C96A33.2 (3)N1B—C9B—C91B—C92B159.4 (2)
C5A—C9A—C91A—C96A160.0 (2)C5B—C9B—C91B—C92B34.4 (3)
N1A—C9A—C91A—C92A152.8 (2)N1B—C9B—C91B—C96B23.7 (3)
C5A—C9A—C91A—C92A26.1 (3)C5B—C9B—C91B—C96B148.8 (2)
C96A—C91A—C92A—C93A0.0 (4)C96B—C91B—C92B—C93B0.9 (4)
C9A—C91A—C92A—C93A174.1 (2)C9B—C91B—C92B—C93B177.8 (2)
C91A—C92A—C93A—C94A0.2 (5)C91B—C92B—C93B—C94B0.5 (4)
C92A—C93A—C94A—C95A0.0 (5)C92B—C93B—C94B—C95B0.8 (4)
C93A—C94A—C95A—C96A0.5 (5)C93B—C94B—C95B—C96B0.4 (4)
C92A—C91A—C96A—C95A0.4 (4)C94B—C95B—C96B—C91B1.8 (4)
C9A—C91A—C96A—C95A173.8 (3)C92B—C91B—C96B—C95B2.1 (4)
C94A—C95A—C96A—C91A0.7 (5)C9B—C91B—C96B—C95B179.0 (2)
C2A—N3A—C10A—C11A168.35 (17)C2B—N3B—C10B—C11B165.33 (16)
C4A—N3A—C10A—C11A73.3 (2)C4B—N3B—C10B—C11B76.2 (2)
C2A—N3A—C10A—C7A60.7 (2)C2B—N3B—C10B—C7B61.58 (19)
C4A—N3A—C10A—C7A57.7 (2)C4B—N3B—C10B—C7B56.9 (2)
C6A—C7A—C10A—N3A54.9 (2)C6B—C7B—C10B—N3B53.0 (2)
C8A—C7A—C10A—N3A60.3 (2)C8B—C7B—C10B—N3B60.9 (2)
C6A—C7A—C10A—C11A75.9 (2)C6B—C7B—C10B—C11B77.8 (2)
C8A—C7A—C10A—C11A168.97 (17)C8B—C7B—C10B—C11B168.30 (17)
N3A—C10A—C11A—C12A118.2 (2)N3B—C10B—C11B—C12B123.1 (2)
C7A—C10A—C11A—C12A10.2 (3)C7B—C10B—C11B—C12B5.9 (3)
N3A—C10A—C11A—C16A65.8 (3)N3B—C10B—C11B—C16B59.4 (3)
C7A—C10A—C11A—C16A165.8 (2)C7B—C10B—C11B—C16B171.6 (2)
C16A—C11A—C12A—C13A1.5 (4)C16B—C11B—C12B—C13B1.2 (4)
C10A—C11A—C12A—C13A177.6 (2)C10B—C11B—C12B—C13B178.7 (2)
C11A—C12A—C13A—C14A0.5 (4)C11B—C12B—C13B—C14B0.3 (4)
C12A—C13A—C14A—C15A0.7 (4)C12B—C13B—C14B—C15B0.9 (4)
C13A—C14A—C15A—C16A0.7 (4)C13B—C14B—C15B—C16B1.1 (4)
C14A—C15A—C16A—C11A0.4 (4)C14B—C15B—C16B—C11B0.2 (4)
C12A—C11A—C16A—C15A1.4 (4)C12B—C11B—C16B—C15B0.9 (4)
C10A—C11A—C16A—C15A177.8 (2)C10B—C11B—C16B—C15B178.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O3i0.982.603.525 (3)158
C10A—H10A···O30.982.563.451 (3)152
C82A—H82A···O1Aii0.932.393.279 (3)160
C92B—H92B···O1Biii0.932.603.511 (3)168
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1; (iii) x+1, y+1, z.
 

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