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Acta Cryst. (2010). E66, o729-o730    [ doi:10.1107/S1600536810007294 ]

4,4',4''-(Methanetriyl)triphenyl tris(2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carboxylate) benzene trisolvate

D. Schuetz, D. Margraf, T. F. Prisner and J. W. Bats

Abstract top

In the asymmetric unit of the title compound, C46H52N3O9·3C6H6, two of the benzene solvent molecules are located in general positions and two are disposed about inversion centers. One of the benzene molecules on an inversion center was grossly disordered and was excluded using the SQUEEZE subroutine in PLATON [Spek (2009). Acta Cryst. D65, 148-155]. In addition, one of the 2,2,5,5-tetramethyl-1-oxyl-3-pyrrolin-3-ylcarbonyl groups is disordered over two orientations with refined occupancies of 0.506 (2) and 0.494 (2). The 1-oxyl-3-pyrroline-3-carboxylate groups are essentially planar, with mean deviations from the planes of 0.026 (2), 0.012 (2), 0.034 (4) and 0.011 (4) Å. In the crystal structure, molecules are connected by five weak intermolecular C-H...O and four weak intermolecular C-H...[pi](benzene) interactions.

Comment top

The title compound was prepared as a reference compound for pulsed electron-electron double resonance measurements (Godt et al., 2000).

The molecular structure is shown in Fig. 1. The 2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carbonyl group attached to atom O7 is disordered over two orientations with equal occupancies. Short intermolecular contact distances [O8···O8(at 1-x,1-y,-z)=2.371 (5)Å and O8'···O8'(at 1-x,-y,-z)=2.354 (5) Å] show that adjacent groups should occupy alternating orientations along the b-direction, resulting in space group symmetry P 1 with Z'=2. A refinement as an ordered structure in P 1, however, resulted in much higher R-values, showing that the packing must be randomly disordered along at least one other direction.

Each of the 1-oxyl-3-pyrroline groups is approximately planar [mean deviation from plane: 0.026 (2), 0.012 (2), 0.034 (4) and 0.011 (4)Å respectively] and is coplanar with the carbonyloxy group to which it is bonded [torsion angles O1—C8—C9—C10: -0.7 (3)° , O4—C23—C24—C25: 2.4 (4)° , O7—C38—C39—C40: -4.5 (7)° and O7—C38'-C39'-C40': 10.5 (9)° ]. Planarity of this group also has been observed in a related crystal structure (Margraf et al., 2009). The acetoxyphenyl groups are non-planar [torsion angles: C8—O1—C5—C6=-68.2 (3)° , C23—O4—C20—C19=86.6 (3)° , C38—O7—C35—C34=-78.9 (5)° and C38'-O7—C35—C34=67.7 (5)° .

The crystal packing is shown in Fig. 2. The asymmetric unit contains a triphenylmethane-4,4',4"-triyl tris(2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carboxylate) molecule, two benzene solvent molecules in general positions and two benzene solvent molecules positioned about inversion centers. One of the latter groups was found to be seriously disordered and was included in the calculations by using program PLATON/SQUEEZE (Spek, 2009). There are five intermolecular C—H···O contacts with H···O distances between 2.44 and 2.58 Å and four intermolecular C—H···πbenzene contacts with H···Cg distances between 2.78 and 2.94 Å (Table 1, Cg represents the centroid of the benzene ring).

Related literature top

For the preparation of the title compound see: Godt et al. (2000). For a related structure, see: Margraf et al. (2009). For the treatment of the disordered solvent, see: Spek (2009).

Experimental top

The title compound was prepared from tris(4-hydroxyphenyl)methane in analogy to the procedure described by Godt et al. (2000). Single crystals were obtained by recrystallization of the compound from benzene.

Refinement top

The H atoms were positioned geometrically and treated as riding: Cprimary—H=1.00 Å, Cmethyl—H=0.98 Å, Cplanar—H=0.95 Å, Uiso(H)=1.2Ueq(Cnon-methyl) and Uiso(H)=1.5Ueq(Cmethyl). A benzene solvent molecule seriously disordered about the inversion center at (0, 0, 0) was accounted for by using the program PLATON/SQUEEZE (Spek, 2009). The electron density count in this region was found to be 42 electrons, in perfect agreement with the value expected for a benzene molecule and the contribution from the additional benzene molecule was added to the empirical formula. The 2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carbonyl group attached to atom O7 was found to be disordered over two possible orientations. Consequently, atoms in this group were refined as split atoms and treated as isotropic, except for the O atoms which were refined with anisotropic displacement parameters. The occupancy factor refined to 0.494 (2) for atoms, O8, O9, N3 and C38 → C46 and to 0.506 (2) for atoms O8', O9', N3' and C38' → C46'. A refinement as an ordered structure in space group P 1 converged at wR(F2)=0.295, R[F2>2σ(F2)]=0.107 and showed residual density up to 1.21 e.A-3 in the 2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carbonyl group, which was disordered in space group P 1. Thus an ordered structure can be excluded. Oxygen atom O7 could not be split to meaningful positions within the experimental resolution. As a result, the observed values of the C35-O7-C38 and C35-O7-C38' angles [128.4 (3) and 140.5 (3)° ] are too large.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound shown with 50% probability displacement ellipsoids. The H atoms are drawn as small spheres of arbitrary radius. Symmetry equivalent atoms are related by i: 2-x, 1-y, 1-z. A disorder component is shown with open bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. H atoms have been omitted. Along the b-direction adjacent molecules are shown with alternating orientations of the disordered side-chain.
4,4',4''-(Methanetriyl)triphenyl tris(2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carboxylate) benzene trisolvate top
Crystal data top
C46H52N3O9·3C6H6Z = 2
Mr = 1025.23F(000) = 1094
Triclinic, P1Dx = 1.154 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0810 (13) ÅCell parameters from 204 reflections
b = 11.7372 (16) Åθ = 3–23°
c = 26.241 (4) ŵ = 0.08 mm−1
α = 98.324 (10)°T = 164 K
β = 92.765 (11)°Rod, yellow
γ = 105.308 (10)°0.70 × 0.20 × 0.20 mm
V = 2951.1 (7) Å3
Data collection top
Siemens SMART 1K CCD
diffractometer		12901 independent reflections
Radiation source: normal-focus sealed tube6172 reflections with I > 2σ(I)
graphiteRint = 0.054
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		h = −13→13
Tmin = 0.878, Tmax = 0.985k = −14→15
43135 measured reflectionsl = −32→33
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.09P)2]
where P = (Fo2 + 2Fc2)/3
12901 reflections(Δ/σ)max = 0.002
667 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C46H52N3O9·3C6H6γ = 105.308 (10)°
Mr = 1025.23V = 2951.1 (7) Å3
Triclinic, P1Z = 2
a = 10.0810 (13) ÅMo Kα radiation
b = 11.7372 (16) ŵ = 0.08 mm−1
c = 26.241 (4) ÅT = 164 K
α = 98.324 (10)°0.70 × 0.20 × 0.20 mm
β = 92.765 (11)°
Data collection top
Siemens SMART 1K CCD
diffractometer		12901 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		6172 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.985Rint = 0.054
43135 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.072H-atom parameters constrained
wR(F2) = 0.194Δρmax = 0.41 e Å−3
S = 1.04Δρmin = −0.40 e Å−3
12901 reflectionsAbsolute structure: ?
667 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/UeqOcc. (<1)
O10.53115 (18)−0.01253 (13)0.36733 (6)0.0452 (4)
O20.72796 (17)0.08878 (15)0.41627 (7)0.0503 (5)
O30.6843 (2)−0.28486 (17)0.51844 (8)0.0653 (6)
O40.81097 (19)0.83869 (14)0.30718 (7)0.0582 (5)
O50.8868 (2)0.81827 (17)0.22723 (9)0.0745 (6)
O61.12533 (19)1.29224 (14)0.25223 (7)0.0590 (5)
O70.4972 (2)0.25906 (19)0.03656 (8)0.0798 (7)
O80.5327 (5)0.4303 (3)0.02292 (14)0.0667 (13)0.494 (2)
O90.5887 (5)0.2649 (4)−0.17679 (13)0.0756 (15)0.494 (2)
O8'0.5441 (5)0.1012 (3)0.01896 (14)0.0781 (14)0.506 (2)
O9'0.5181 (7)0.1270 (5)−0.18702 (15)0.122 (2)0.506 (2)
N10.6415 (2)−0.24001 (18)0.48143 (8)0.0458 (5)
N21.0619 (2)1.20024 (17)0.27055 (8)0.0469 (6)
N30.5720 (5)0.2458 (5)−0.13101 (17)0.0466 (12)*0.494 (2)
N3'0.5159 (6)0.1762 (6)−0.1401 (2)0.0668 (15)*0.506 (2)
C10.4798 (2)0.35575 (19)0.25423 (9)0.0358 (6)
H1A0.38260.35720.25950.043*
C20.5085 (2)0.26105 (19)0.28438 (9)0.0327 (5)
C30.5311 (3)0.1558 (2)0.26070 (9)0.0453 (6)
H3A0.53870.14410.22450.054*
C40.5429 (3)0.0661 (2)0.28895 (9)0.0437 (6)
H4A0.5576−0.00630.27220.052*
C50.5329 (2)0.08435 (19)0.34088 (9)0.0381 (6)
C60.5110 (3)0.1883 (2)0.36585 (10)0.0483 (7)
H6A0.50290.19960.40200.058*
C70.5011 (3)0.2761 (2)0.33715 (10)0.0452 (7)
H7A0.48870.34910.35430.054*
C80.6331 (3)−0.0003 (2)0.40459 (9)0.0367 (6)
C90.6121 (2)−0.1091 (2)0.42854 (9)0.0348 (6)
C100.5068 (2)−0.2069 (2)0.41613 (9)0.0372 (6)
H10A0.4356−0.21580.38960.045*
C110.5119 (3)−0.3016 (2)0.44818 (10)0.0426 (6)
C120.5255 (3)−0.4162 (2)0.41644 (11)0.0627 (8)
H12A0.6038−0.39740.39550.094*
H12B0.4406−0.45450.39370.094*
H12C0.5407−0.47080.43970.094*
C130.3917 (3)−0.3261 (3)0.48212 (11)0.0567 (8)
H13A0.3862−0.25050.50210.085*
H13B0.4066−0.37980.50580.085*
H13C0.3053−0.36380.46020.085*
C140.7124 (2)−0.1188 (2)0.47093 (9)0.0409 (6)
C150.8546 (3)−0.1184 (3)0.45284 (12)0.0599 (8)
H15A0.8436−0.17760.42140.090*
H15B0.9102−0.13880.48000.090*
H15C0.9011−0.03870.44560.090*
C160.7252 (3)−0.0275 (3)0.51980 (10)0.0613 (8)
H16A0.6329−0.02890.53030.092*
H16B0.77170.05260.51300.092*
H16C0.7791−0.04760.54750.092*
C170.5699 (2)0.4829 (2)0.27361 (9)0.0381 (6)
C180.7073 (2)0.5096 (2)0.29182 (9)0.0398 (6)
H18A0.74670.44640.29670.048*
C190.7888 (3)0.6274 (2)0.30317 (10)0.0444 (6)
H19A0.88330.64500.31550.053*
C200.7306 (3)0.7174 (2)0.29620 (11)0.0516 (7)
C210.5926 (3)0.6943 (2)0.28051 (15)0.0825 (11)
H21A0.55250.75800.27760.099*
C220.5140 (3)0.5773 (2)0.26915 (14)0.0728 (10)
H22A0.41880.56060.25800.087*
C230.8817 (3)0.8800 (2)0.26730 (13)0.0531 (7)
C240.9470 (3)1.0102 (2)0.27938 (11)0.0443 (6)
C250.9442 (3)1.0799 (2)0.32329 (11)0.0492 (7)
H25A0.90211.05080.35220.059*
C261.0145 (3)1.2103 (2)0.32310 (10)0.0470 (7)
C271.1365 (3)1.2618 (3)0.36340 (11)0.0623 (8)
H27A1.20061.21190.35970.093*
H27B1.10391.26360.39800.093*
H27C1.18401.34340.35860.093*
C280.9105 (3)1.2851 (2)0.32690 (13)0.0644 (8)
H28A0.83361.24920.30020.097*
H28B0.95621.36690.32180.097*
H28C0.87541.28700.36110.097*
C291.0226 (3)1.0784 (2)0.24016 (10)0.0535 (7)
C301.1532 (4)1.0425 (2)0.22696 (14)0.0836 (11)
H30A1.20971.04620.25890.125*
H30B1.20591.09740.20580.125*
H30C1.12790.96060.20770.125*
C310.9301 (5)1.0754 (3)0.19274 (13)0.1072 (15)
H31A0.84841.09980.20330.161*
H31B0.90130.99400.17300.161*
H31C0.98051.13060.17110.161*
C320.4854 (3)0.3272 (2)0.19600 (9)0.0384 (6)
C330.6103 (3)0.3336 (2)0.17411 (10)0.0512 (7)
H33A0.69370.35390.19600.061*
C340.6145 (3)0.3109 (2)0.12123 (11)0.0534 (7)
H34A0.70000.31620.10670.064*
C350.4927 (3)0.2805 (2)0.08983 (9)0.0479 (7)
C360.3685 (3)0.2738 (2)0.10991 (10)0.0508 (7)
H36A0.28560.25340.08770.061*
C370.3655 (3)0.2974 (2)0.16310 (10)0.0435 (6)
H37A0.27960.29300.17720.052*
C380.5259 (5)0.3267 (5)0.00924 (18)0.0342 (11)*0.494 (2)
C390.5383 (5)0.2737 (6)−0.0439 (2)0.0372 (13)*0.494 (2)
C400.5269 (6)0.1600 (6)−0.0584 (3)0.0435 (19)*0.494 (2)
H40A0.51230.1041−0.03500.052*0.494 (2)
C410.5385 (8)0.1254 (7)−0.1142 (3)0.062 (2)*0.494 (2)
C420.6402 (8)0.0620 (7)−0.1295 (3)0.088 (2)*0.494 (2)
H42A0.73130.1072−0.11230.131*0.494 (2)
H42B0.64380.0537−0.16710.131*0.494 (2)
H42C0.6141−0.0176−0.11940.131*0.494 (2)
C430.3930 (7)0.0497 (7)−0.1432 (3)0.088 (2)*0.494 (2)
H43A0.40310.0283−0.18000.132*0.494 (2)
H43B0.32670.0975−0.13910.132*0.494 (2)
H43C0.3595−0.0234−0.12820.132*0.494 (2)
C440.5595 (5)0.3435 (5)−0.0885 (2)0.0382 (12)*0.494 (2)
C450.6952 (6)0.4419 (5)−0.0809 (2)0.0639 (17)*0.494 (2)
H45A0.77100.4084−0.07210.096*0.494 (2)
H45B0.69080.5052−0.05280.096*0.494 (2)
H45C0.71100.4754−0.11290.096*0.494 (2)
C460.4390 (6)0.3926 (5)−0.1013 (2)0.0616 (17)*0.494 (2)
H46A0.35290.3279−0.10560.092*0.494 (2)
H46B0.45210.4257−0.13350.092*0.494 (2)
H46C0.43450.4557−0.07310.092*0.494 (2)
C38'0.5238 (5)0.1855 (5)0.00195 (19)0.0417 (13)*0.506 (2)
C39'0.5230 (6)0.2059 (8)−0.0516 (2)0.0424 (16)*0.506 (2)
C40'0.5158 (5)0.3052 (5)−0.0676 (2)0.0384 (12)*0.506 (2)
H40B0.51160.3748−0.04490.046*0.506 (2)
C41'0.5147 (5)0.2980 (5)−0.1243 (2)0.0438 (13)*0.506 (2)
C42'0.6415 (7)0.3871 (6)−0.1412 (3)0.082 (2)*0.506 (2)
H42D0.72650.3733−0.12690.123*0.506 (2)
H42E0.63990.4693−0.12820.123*0.506 (2)
H42F0.63820.3750−0.17900.123*0.506 (2)
C43'0.3833 (6)0.3192 (5)−0.1471 (2)0.0643 (17)*0.506 (2)
H43D0.30280.2629−0.13660.096*0.506 (2)
H43E0.38100.3068−0.18490.096*0.506 (2)
H43F0.38140.4014−0.13430.096*0.506 (2)
C44'0.5244 (8)0.1077 (7)−0.0966 (4)0.071 (3)*0.506 (2)
C45'0.6756 (9)0.0850 (9)−0.0961 (4)0.119 (3)*0.506 (2)
H45D0.74630.1620−0.09200.178*0.506 (2)
H45E0.68320.0357−0.12870.178*0.506 (2)
H45F0.68910.0435−0.06720.178*0.506 (2)
C46'0.4074 (8)−0.0006 (6)−0.1012 (3)0.092 (2)*0.506 (2)
H46D0.32080.0223−0.10020.139*0.506 (2)
H46E0.4172−0.0432−0.07230.139*0.506 (2)
H46F0.4065−0.0529−0.13390.139*0.506 (2)
C470.2098 (3)−0.3127 (3)0.28489 (12)0.0630 (8)
H47A0.2370−0.33130.25120.076*
C480.1703 (3)−0.4011 (2)0.31486 (12)0.0572 (8)
H48A0.1703−0.48100.30180.069*
C490.1310 (3)−0.3743 (3)0.36369 (12)0.0563 (7)
H49A0.1036−0.43550.38420.068*
C500.1314 (3)−0.2589 (3)0.38264 (13)0.0654 (8)
H50A0.1049−0.24040.41640.078*
C510.1698 (3)−0.1704 (3)0.35336 (16)0.0736 (10)
H51A0.1693−0.09080.36660.088*
C520.2094 (3)−0.1976 (3)0.30418 (16)0.0753 (10)
H52A0.2364−0.13630.28370.090*
C530.9261 (6)0.5700 (5)0.4825 (2)0.1024 (15)
H53A0.87360.61840.47010.123*
C540.8921 (4)0.4510 (6)0.46383 (17)0.0996 (13)
H54A0.81640.41670.43830.119*
C550.9666 (7)0.3799 (4)0.4815 (2)0.1074 (17)
H55A0.94270.29650.46850.129*
C560.9982 (5)0.3708 (5)0.1088 (3)0.130 (2)
H56A1.02640.29920.10370.155*
C571.0004 (4)0.4293 (7)0.1570 (3)0.118 (2)
H57A1.02530.39700.18600.142*
C580.9666 (4)0.5348 (6)0.1639 (2)0.1088 (15)
H58A0.96960.57650.19800.131*
C590.9297 (5)0.5806 (5)0.1240 (3)0.1202 (17)
H59A0.90810.65520.12950.144*
C600.9229 (6)0.5220 (7)0.0763 (3)0.137 (2)
H60A0.89500.55530.04810.164*
C610.9551 (6)0.4146 (6)0.0666 (2)0.143 (2)
H61A0.94810.37230.03240.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0549 (11)0.0294 (9)0.0482 (10)0.0016 (8)−0.0070 (9)0.0187 (8)
O20.0420 (11)0.0401 (11)0.0661 (12)0.0012 (9)0.0022 (9)0.0196 (9)
O30.0700 (13)0.0698 (13)0.0685 (13)0.0271 (11)−0.0038 (10)0.0403 (11)
O40.0603 (12)0.0294 (10)0.0776 (14)−0.0058 (9)0.0028 (10)0.0202 (9)
O50.0835 (16)0.0350 (11)0.0957 (17)0.0015 (10)0.0256 (13)0.0019 (11)
O60.0695 (13)0.0312 (10)0.0778 (13)0.0054 (9)0.0229 (10)0.0241 (9)
O70.1142 (19)0.0721 (15)0.0448 (13)0.0173 (13)0.0237 (12)−0.0077 (11)
O80.126 (4)0.039 (2)0.044 (2)0.033 (2)0.021 (2)0.0153 (17)
O90.114 (4)0.114 (4)0.023 (2)0.054 (3)0.025 (2)0.039 (2)
O8'0.157 (4)0.048 (2)0.046 (2)0.051 (3)0.012 (2)0.0189 (18)
O9'0.267 (7)0.102 (4)0.031 (2)0.110 (5)0.033 (3)0.003 (2)
N10.0466 (13)0.0473 (13)0.0520 (14)0.0189 (11)0.0046 (11)0.0249 (11)
N20.0520 (14)0.0282 (12)0.0610 (15)0.0057 (10)0.0105 (11)0.0166 (10)
C10.0383 (14)0.0304 (13)0.0405 (14)0.0073 (11)0.0042 (11)0.0155 (10)
C20.0345 (13)0.0236 (12)0.0376 (14)0.0009 (10)0.0013 (10)0.0114 (10)
C30.0679 (18)0.0353 (15)0.0350 (14)0.0160 (13)0.0039 (13)0.0104 (11)
C40.0641 (18)0.0284 (13)0.0414 (16)0.0151 (12)0.0035 (13)0.0103 (11)
C50.0462 (15)0.0244 (13)0.0426 (15)0.0025 (11)−0.0002 (12)0.0164 (11)
C60.0709 (19)0.0384 (15)0.0399 (15)0.0151 (13)0.0148 (13)0.0169 (12)
C70.0634 (18)0.0296 (14)0.0455 (16)0.0131 (12)0.0140 (13)0.0120 (11)
C80.0374 (15)0.0338 (14)0.0413 (15)0.0085 (12)0.0116 (12)0.0138 (11)
C90.0358 (14)0.0347 (14)0.0392 (14)0.0133 (11)0.0097 (11)0.0144 (11)
C100.0386 (14)0.0372 (14)0.0394 (14)0.0105 (12)0.0048 (11)0.0167 (11)
C110.0476 (16)0.0340 (14)0.0510 (16)0.0117 (12)0.0058 (13)0.0210 (12)
C120.086 (2)0.0397 (16)0.069 (2)0.0240 (15)0.0102 (17)0.0195 (14)
C130.0541 (18)0.0594 (18)0.0647 (19)0.0140 (14)0.0143 (14)0.0363 (15)
C140.0412 (15)0.0409 (15)0.0449 (15)0.0150 (12)0.0024 (12)0.0146 (12)
C150.0400 (16)0.066 (2)0.080 (2)0.0177 (14)0.0050 (15)0.0270 (16)
C160.076 (2)0.0577 (19)0.0503 (18)0.0206 (16)−0.0059 (15)0.0069 (14)
C170.0392 (15)0.0290 (13)0.0473 (15)0.0054 (11)0.0017 (12)0.0184 (11)
C180.0418 (16)0.0321 (14)0.0496 (15)0.0128 (12)0.0045 (12)0.0156 (11)
C190.0373 (15)0.0381 (15)0.0586 (17)0.0074 (12)0.0060 (12)0.0153 (12)
C200.0487 (18)0.0263 (14)0.077 (2)−0.0002 (12)0.0014 (14)0.0205 (13)
C210.064 (2)0.0321 (17)0.151 (3)0.0093 (15)−0.027 (2)0.0321 (18)
C220.0427 (17)0.0339 (16)0.142 (3)0.0057 (13)−0.0173 (18)0.0319 (17)
C230.0465 (17)0.0308 (15)0.082 (2)0.0053 (13)0.0054 (16)0.0195 (15)
C240.0418 (15)0.0304 (14)0.0622 (18)0.0090 (12)0.0054 (13)0.0137 (13)
C250.0439 (16)0.0367 (15)0.071 (2)0.0089 (12)0.0178 (14)0.0227 (14)
C260.0436 (16)0.0330 (14)0.0651 (18)0.0063 (12)0.0166 (14)0.0143 (12)
C270.0563 (19)0.0573 (19)0.066 (2)0.0076 (15)−0.0022 (16)0.0045 (15)
C280.0548 (18)0.0371 (16)0.103 (2)0.0112 (14)0.0236 (17)0.0133 (15)
C290.078 (2)0.0296 (15)0.0514 (17)0.0084 (14)0.0068 (15)0.0124 (12)
C300.115 (3)0.0370 (17)0.106 (3)0.0186 (17)0.070 (2)0.0210 (16)
C310.178 (4)0.051 (2)0.074 (2)0.003 (2)−0.039 (3)0.0182 (17)
C320.0457 (16)0.0292 (13)0.0434 (15)0.0080 (11)0.0057 (13)0.0195 (11)
C330.0536 (18)0.0550 (17)0.0491 (17)0.0151 (14)0.0057 (14)0.0210 (13)
C340.066 (2)0.0510 (17)0.0520 (18)0.0192 (15)0.0219 (16)0.0239 (13)
C350.084 (2)0.0296 (14)0.0330 (15)0.0169 (14)0.0055 (15)0.0118 (11)
C360.0592 (19)0.0459 (16)0.0475 (17)0.0124 (14)0.0038 (14)0.0129 (13)
C370.0508 (17)0.0393 (15)0.0421 (16)0.0095 (12)0.0064 (13)0.0162 (11)
C470.0531 (19)0.065 (2)0.071 (2)0.0108 (16)0.0041 (15)0.0203 (17)
C480.0491 (18)0.0398 (16)0.080 (2)0.0088 (13)0.0016 (16)0.0097 (15)
C490.0403 (16)0.0519 (19)0.075 (2)0.0052 (13)0.0040 (15)0.0204 (15)
C500.0527 (19)0.059 (2)0.083 (2)0.0197 (16)−0.0031 (16)0.0030 (18)
C510.065 (2)0.047 (2)0.105 (3)0.0186 (16)−0.021 (2)0.0022 (19)
C520.065 (2)0.053 (2)0.105 (3)0.0042 (17)−0.021 (2)0.035 (2)
C530.119 (4)0.090 (4)0.130 (4)0.057 (3)0.074 (3)0.046 (3)
C540.079 (3)0.114 (4)0.107 (3)0.016 (3)0.051 (2)0.028 (3)
C550.134 (4)0.061 (3)0.132 (4)0.020 (3)0.085 (4)0.021 (3)
C560.112 (4)0.121 (4)0.202 (6)0.071 (3)0.083 (4)0.085 (5)
C570.055 (2)0.177 (6)0.145 (5)0.023 (3)0.019 (3)0.114 (5)
C580.058 (3)0.158 (5)0.102 (4)0.010 (3)0.011 (2)0.027 (3)
C590.092 (3)0.126 (4)0.166 (5)0.056 (3)0.031 (4)0.042 (4)
C600.147 (5)0.157 (6)0.146 (5)0.064 (4)0.040 (4)0.103 (5)
C610.157 (5)0.170 (6)0.119 (4)0.054 (4)0.089 (4)0.040 (4)
Geometric parameters (Å, °) top
O1—C81.348 (3)C31—H31A0.9800
O1—C51.412 (3)C31—H31B0.9800
O2—C81.205 (3)C31—H31C0.9800
O3—N11.279 (2)C32—C371.385 (3)
O4—C231.369 (3)C32—C331.398 (3)
O4—C201.419 (3)C33—C341.380 (4)
O5—C231.199 (3)C33—H33A0.9500
O6—N21.273 (2)C34—C351.379 (4)
O7—C381.137 (5)C34—H34A0.9500
O7—C38'1.250 (5)C35—C361.369 (4)
O7—C351.389 (3)C36—C371.387 (3)
O8—C381.200 (5)C36—H36A0.9500
O9—N31.264 (5)C37—H37A0.9500
O8'—C38'1.203 (6)C38—C391.466 (7)
O9'—N3'1.285 (6)C39—C401.306 (9)
N1—C111.483 (3)C39—C441.516 (8)
N1—C141.486 (3)C40—C411.481 (11)
N2—C291.476 (3)C40—H40A0.9500
N2—C261.480 (3)C41—C421.457 (10)
N3—C411.499 (10)C41—C431.590 (10)
N3—C441.515 (7)C42—H42A0.9800
N3'—C41'1.434 (8)C42—H42B0.9800
N3'—C44'1.500 (10)C42—H42C0.9800
C1—C321.523 (3)C43—H43A0.9800
C1—C171.527 (3)C43—H43B0.9800
C1—C21.532 (3)C43—H43C0.9800
C1—H1A1.0000C44—C461.518 (7)
C2—C71.379 (3)C44—C451.522 (8)
C2—C31.379 (3)C45—H45A0.9800
C3—C41.399 (3)C45—H45B0.9800
C3—H3A0.9500C45—H45C0.9800
C4—C51.361 (3)C46—H46A0.9800
C4—H4A0.9500C46—H46B0.9800
C5—C61.376 (3)C46—H46C0.9800
C6—C71.382 (3)C38'—C39'1.460 (8)
C6—H6A0.9500C39'—C40'1.313 (9)
C7—H7A0.9500C39'—C44'1.529 (11)
C8—C91.474 (3)C40'—C41'1.480 (8)
C9—C101.329 (3)C40'—H40B0.9500
C9—C141.504 (3)C41'—C43'1.521 (7)
C10—C111.498 (3)C41'—C42'1.550 (8)
C10—H10A0.9500C42'—H42D0.9800
C11—C121.518 (3)C42'—H42E0.9800
C11—C131.529 (3)C42'—H42F0.9800
C12—H12A0.9800C43'—H43D0.9800
C12—H12B0.9800C43'—H43E0.9800
C12—H12C0.9800C43'—H43F0.9800
C13—H13A0.9800C44'—C46'1.474 (10)
C13—H13B0.9800C44'—C45'1.615 (12)
C13—H13C0.9800C45'—H45D0.9800
C14—C161.524 (4)C45'—H45E0.9800
C14—C151.531 (3)C45'—H45F0.9800
C15—H15A0.9800C46'—H46D0.9800
C15—H15B0.9800C46'—H46E0.9800
C15—H15C0.9800C46'—H46F0.9800
C16—H16A0.9800C47—C521.374 (4)
C16—H16B0.9800C47—C481.379 (4)
C16—H16C0.9800C47—H47A0.9500
C17—C181.382 (3)C48—C491.377 (4)
C17—C221.385 (3)C48—H48A0.9500
C18—C191.390 (3)C49—C501.372 (4)
C18—H18A0.9500C49—H49A0.9500
C19—C201.367 (3)C50—C511.366 (4)
C19—H19A0.9500C50—H50A0.9500
C20—C211.375 (4)C51—C521.387 (5)
C21—C221.374 (4)C51—H51A0.9500
C21—H21A0.9500C52—H52A0.9500
C22—H22A0.9500C53—C55i1.347 (6)
C23—C241.475 (4)C53—C541.357 (6)
C24—C251.319 (4)C53—H53A0.9500
C24—C291.508 (3)C54—C551.373 (6)
C25—C261.508 (3)C54—H54A0.9500
C25—H25A0.9500C55—C53i1.347 (6)
C26—C271.515 (4)C55—H55A0.9500
C26—C281.532 (4)C56—C571.346 (7)
C27—H27A0.9800C56—C611.384 (7)
C27—H27B0.9800C56—H56A0.9500
C27—H27C0.9800C57—C581.358 (7)
C28—H28A0.9800C57—H57A0.9500
C28—H28B0.9800C58—C591.326 (6)
C28—H28C0.9800C58—H58A0.9500
C29—C311.509 (4)C59—C601.327 (7)
C29—C301.525 (4)C59—H59A0.9500
C30—H30A0.9800C60—C611.375 (7)
C30—H30B0.9800C60—H60A0.9500
C30—H30C0.9800C61—H61A0.9500
C8—O1—C5118.87 (18)C34—C33—C32121.1 (3)
C23—O4—C20115.0 (2)C34—C33—H33A119.4
C38—O7—C35128.4 (3)C32—C33—H33A119.4
C38'—O7—C35140.5 (3)C35—C34—C33118.9 (3)
O3—N1—C11122.38 (19)C35—C34—H34A120.5
O3—N1—C14122.5 (2)C33—C34—H34A120.5
C11—N1—C14115.02 (18)C36—C35—C34121.5 (2)
O6—N2—C29122.8 (2)C36—C35—O7119.6 (3)
O6—N2—C26121.55 (19)C34—C35—O7118.9 (3)
C29—N2—C26115.49 (18)C35—C36—C37119.1 (3)
O9—N3—C41125.6 (5)C35—C36—H36A120.5
O9—N3—C44121.5 (5)C37—C36—H36A120.5
C41—N3—C44112.1 (5)C32—C37—C36121.2 (2)
O9'—N3'—C41'125.1 (6)C32—C37—H37A119.4
O9'—N3'—C44'120.0 (6)C36—C37—H37A119.4
C41'—N3'—C44'114.8 (5)O7—C38—O8121.0 (5)
C32—C1—C17108.73 (17)O7—C38—C39114.1 (5)
C32—C1—C2114.44 (18)O8—C38—C39124.5 (5)
C17—C1—C2114.55 (19)C40—C39—C38123.7 (6)
C32—C1—H1A106.1C40—C39—C44112.4 (5)
C17—C1—H1A106.1C38—C39—C44123.8 (5)
C2—C1—H1A106.1C39—C40—C41114.6 (6)
C7—C2—C3117.7 (2)C39—C40—H40A122.7
C7—C2—C1119.1 (2)C41—C40—H40A122.7
C3—C2—C1123.0 (2)C42—C41—C40118.7 (8)
C2—C3—C4121.3 (2)C42—C41—N3111.0 (6)
C2—C3—H3A119.3C40—C41—N3100.5 (6)
C4—C3—H3A119.3C42—C41—C43107.8 (6)
C5—C4—C3118.8 (2)C40—C41—C43110.9 (6)
C5—C4—H4A120.6N3—C41—C43107.3 (7)
C3—C4—H4A120.6C41—C42—H42A109.5
C4—C5—C6121.5 (2)C41—C42—H42B109.5
C4—C5—O1117.3 (2)H42A—C42—H42B109.5
C6—C5—O1120.9 (2)C41—C42—H42C109.5
C5—C6—C7118.6 (2)H42A—C42—H42C109.5
C5—C6—H6A120.7H42B—C42—H42C109.5
C7—C6—H6A120.7C41—C43—H43A109.5
C2—C7—C6122.1 (2)C41—C43—H43B109.5
C2—C7—H7A119.0H43A—C43—H43B109.5
C6—C7—H7A119.0C41—C43—H43C109.5
O2—C8—O1123.6 (2)H43A—C43—H43C109.5
O2—C8—C9125.3 (2)H43B—C43—H43C109.5
O1—C8—C9111.1 (2)N3—C44—C3999.8 (4)
C10—C9—C8125.5 (2)N3—C44—C46111.7 (4)
C10—C9—C14112.9 (2)C39—C44—C46113.3 (5)
C8—C9—C14121.6 (2)N3—C44—C45107.8 (4)
C9—C10—C11113.2 (2)C39—C44—C45112.7 (4)
C9—C10—H10A123.4C46—C44—C45111.0 (4)
C11—C10—H10A123.4C44—C45—H45A109.5
N1—C11—C1099.52 (18)C44—C45—H45B109.5
N1—C11—C12110.3 (2)H45A—C45—H45B109.5
C10—C11—C12112.9 (2)C44—C45—H45C109.5
N1—C11—C13109.2 (2)H45A—C45—H45C109.5
C10—C11—C13112.6 (2)H45B—C45—H45C109.5
C12—C11—C13111.6 (2)C44—C46—H46A109.5
C11—C12—H12A109.5C44—C46—H46B109.5
C11—C12—H12B109.5H46A—C46—H46B109.5
H12A—C12—H12B109.5C44—C46—H46C109.5
C11—C12—H12C109.5H46A—C46—H46C109.5
H12A—C12—H12C109.5H46B—C46—H46C109.5
H12B—C12—H12C109.5O8'—C38'—O7111.5 (4)
C11—C13—H13A109.5O8'—C38'—C39'128.1 (6)
C11—C13—H13B109.5O7—C38'—C39'120.4 (5)
H13A—C13—H13B109.5C40'—C39'—C38'125.8 (7)
C11—C13—H13C109.5C40'—C39'—C44'112.0 (6)
H13A—C13—H13C109.5C38'—C39'—C44'122.2 (7)
H13B—C13—H13C109.5C39'—C40'—C41'113.3 (5)
N1—C14—C999.35 (19)C39'—C40'—H40B123.4
N1—C14—C16109.3 (2)C41'—C40'—H40B123.4
C9—C14—C16114.0 (2)N3'—C41'—C40'101.5 (4)
N1—C14—C15109.4 (2)N3'—C41'—C43'110.4 (5)
C9—C14—C15113.0 (2)C40'—C41'—C43'110.9 (4)
C16—C14—C15111.1 (2)N3'—C41'—C42'111.6 (5)
C14—C15—H15A109.5C40'—C41'—C42'113.1 (5)
C14—C15—H15B109.5C43'—C41'—C42'109.2 (5)
H15A—C15—H15B109.5C41'—C42'—H42D109.5
C14—C15—H15C109.5C41'—C42'—H42E109.5
H15A—C15—H15C109.5H42D—C42'—H42E109.5
H15B—C15—H15C109.5C41'—C42'—H42F109.5
C14—C16—H16A109.5H42D—C42'—H42F109.5
C14—C16—H16B109.5H42E—C42'—H42F109.5
H16A—C16—H16B109.5C41'—C43'—H43D109.5
C14—C16—H16C109.5C41'—C43'—H43E109.5
H16A—C16—H16C109.5H43D—C43'—H43E109.5
H16B—C16—H16C109.5C41'—C43'—H43F109.5
C18—C17—C22118.0 (2)H43D—C43'—H43F109.5
C18—C17—C1123.6 (2)H43E—C43'—H43F109.5
C22—C17—C1118.2 (2)C46'—C44'—N3'111.9 (6)
C17—C18—C19121.1 (2)C46'—C44'—C39'114.3 (7)
C17—C18—H18A119.5N3'—C44'—C39'98.4 (5)
C19—C18—H18A119.5C46'—C44'—C45'115.5 (7)
C20—C19—C18118.8 (2)N3'—C44'—C45'105.6 (7)
C20—C19—H19A120.6C39'—C44'—C45'109.4 (7)
C18—C19—H19A120.6C44'—C45'—H45D109.5
C19—C20—C21121.5 (2)C44'—C45'—H45E109.5
C19—C20—O4120.3 (2)H45D—C45'—H45E109.5
C21—C20—O4118.1 (2)C44'—C45'—H45F109.5
C22—C21—C20118.7 (3)H45D—C45'—H45F109.5
C22—C21—H21A120.6H45E—C45'—H45F109.5
C20—C21—H21A120.6C44'—C46'—H46D109.5
C21—C22—C17121.7 (3)C44'—C46'—H46E109.5
C21—C22—H22A119.2H46D—C46'—H46E109.5
C17—C22—H22A119.2C44'—C46'—H46F109.5
O5—C23—O4124.0 (2)H46D—C46'—H46F109.5
O5—C23—C24124.5 (3)H46E—C46'—H46F109.5
O4—C23—C24111.4 (3)C52—C47—C48119.4 (3)
C25—C24—C23125.7 (2)C52—C47—H47A120.3
C25—C24—C29112.7 (2)C48—C47—H47A120.3
C23—C24—C29121.5 (2)C49—C48—C47120.3 (3)
C24—C25—C26113.4 (2)C49—C48—H48A119.8
C24—C25—H25A123.3C47—C48—H48A119.8
C26—C25—H25A123.3C50—C49—C48119.8 (3)
N2—C26—C2598.93 (19)C50—C49—H49A120.1
N2—C26—C27110.5 (2)C48—C49—H49A120.1
C25—C26—C27113.5 (2)C51—C50—C49120.6 (3)
N2—C26—C28110.1 (2)C51—C50—H50A119.7
C25—C26—C28111.2 (2)C49—C50—H50A119.7
C27—C26—C28111.9 (2)C50—C51—C52119.5 (3)
C26—C27—H27A109.5C50—C51—H51A120.2
C26—C27—H27B109.5C52—C51—H51A120.2
H27A—C27—H27B109.5C47—C52—C51120.4 (3)
C26—C27—H27C109.5C47—C52—H52A119.8
H27A—C27—H27C109.5C51—C52—H52A119.8
H27B—C27—H27C109.5C55i—C53—C54120.5 (4)
C26—C28—H28A109.5C55i—C53—H53A119.7
C26—C28—H28B109.5C54—C53—H53A119.7
H28A—C28—H28B109.5C53—C54—C55120.4 (4)
C26—C28—H28C109.5C53—C54—H54A119.8
H28A—C28—H28C109.5C55—C54—H54A119.8
H28B—C28—H28C109.5C53i—C55—C54119.1 (4)
N2—C29—C2499.4 (2)C53i—C55—H55A120.5
N2—C29—C31109.2 (2)C54—C55—H55A120.5
C24—C29—C31112.9 (3)C57—C56—C61120.2 (5)
N2—C29—C30109.1 (2)C57—C56—H56A119.9
C24—C29—C30112.7 (2)C61—C56—H56A119.9
C31—C29—C30112.7 (3)C56—C57—C58119.6 (5)
C29—C30—H30A109.5C56—C57—H57A120.2
C29—C30—H30B109.5C58—C57—H57A120.2
H30A—C30—H30B109.5C59—C58—C57121.2 (5)
C29—C30—H30C109.5C59—C58—H58A119.4
H30A—C30—H30C109.5C57—C58—H58A119.4
H30B—C30—H30C109.5C58—C59—C60119.9 (5)
C29—C31—H31A109.5C58—C59—H59A120.1
C29—C31—H31B109.5C60—C59—H59A120.1
H31A—C31—H31B109.5C59—C60—C61121.9 (5)
C29—C31—H31C109.5C59—C60—H60A119.0
H31A—C31—H31C109.5C61—C60—H60A119.0
H31B—C31—H31C109.5C60—C61—C56117.1 (5)
C37—C32—C33118.2 (2)C60—C61—H61A121.4
C37—C32—C1120.1 (2)C56—C61—H61A121.4
C33—C32—C1121.7 (2)
C32—C1—C2—C7−177.7 (2)C17—C1—C32—C37−120.5 (2)
C17—C1—C2—C755.8 (3)C2—C1—C32—C37110.0 (2)
C32—C1—C2—C3−3.0 (3)C17—C1—C32—C3357.6 (3)
C17—C1—C2—C3−129.5 (2)C2—C1—C32—C33−71.9 (3)
C7—C2—C3—C41.4 (4)C37—C32—C33—C340.0 (4)
C1—C2—C3—C4−173.3 (2)C1—C32—C33—C34−178.1 (2)
C2—C3—C4—C5−0.6 (4)C32—C33—C34—C35−0.6 (4)
C3—C4—C5—C60.3 (4)C33—C34—C35—C360.8 (4)
C3—C4—C5—O1173.7 (2)C33—C34—C35—O7179.3 (2)
C8—O1—C5—C4118.3 (2)C38—O7—C35—C3699.6 (4)
C8—O1—C5—C6−68.2 (3)C38'—O7—C35—C36−113.8 (5)
C4—C5—C6—C7−0.9 (4)C38—O7—C35—C34−78.9 (5)
O1—C5—C6—C7−174.1 (2)C38'—O7—C35—C3467.7 (5)
C3—C2—C7—C6−2.1 (4)C34—C35—C36—C37−0.5 (4)
C1—C2—C7—C6172.9 (2)O7—C35—C36—C37−178.9 (2)
C5—C6—C7—C21.9 (4)C33—C32—C37—C360.3 (3)
C5—O1—C8—O2−1.2 (3)C1—C32—C37—C36178.4 (2)
C5—O1—C8—C9178.68 (19)C35—C36—C37—C32−0.1 (4)
O2—C8—C9—C10179.2 (2)C35—O7—C38—O8−14.1 (7)
O1—C8—C9—C10−0.7 (3)C35—O7—C38—C39172.1 (3)
O2—C8—C9—C14−0.6 (4)O7—C38—C39—C40−4.5 (7)
O1—C8—C9—C14179.4 (2)O8—C38—C39—C40−178.1 (5)
C8—C9—C10—C11−178.5 (2)O7—C38—C39—C44172.8 (5)
C14—C9—C10—C111.4 (3)O8—C38—C39—C44−0.8 (8)
O3—N1—C11—C10175.2 (2)C38—C39—C40—C41178.1 (5)
C14—N1—C11—C10−0.7 (2)C44—C39—C40—C410.6 (7)
O3—N1—C11—C12−65.9 (3)C39—C40—C41—C42125.7 (7)
C14—N1—C11—C12118.2 (2)C39—C40—C41—N34.6 (7)
O3—N1—C11—C1357.1 (3)C39—C40—C41—C43−108.7 (7)
C14—N1—C11—C13−118.8 (2)O9—N3—C41—C4255.6 (9)
C9—C10—C11—N1−0.4 (3)C44—N3—C41—C42−134.6 (6)
C9—C10—C11—C12−117.3 (2)O9—N3—C41—C40−177.9 (5)
C9—C10—C11—C13115.1 (2)C44—N3—C41—C40−8.1 (7)
O3—N1—C14—C9−174.5 (2)O9—N3—C41—C43−62.0 (7)
C11—N1—C14—C91.4 (2)C44—N3—C41—C43107.9 (6)
O3—N1—C14—C16−54.8 (3)O9—N3—C44—C39178.7 (5)
C11—N1—C14—C16121.0 (2)C41—N3—C44—C398.3 (6)
O3—N1—C14—C1567.0 (3)O9—N3—C44—C4658.7 (7)
C11—N1—C14—C15−117.2 (2)C41—N3—C44—C46−111.7 (6)
C10—C9—C14—N1−1.6 (2)O9—N3—C44—C45−63.5 (6)
C8—C9—C14—N1178.25 (19)C41—N3—C44—C45126.2 (5)
C10—C9—C14—C16−117.7 (2)C40—C39—C44—N3−5.4 (6)
C8—C9—C14—C1662.2 (3)C38—C39—C44—N3177.1 (5)
C10—C9—C14—C15114.2 (2)C40—C39—C44—C46113.5 (5)
C8—C9—C14—C15−65.9 (3)C38—C39—C44—C46−64.1 (7)
C32—C1—C17—C18−92.5 (3)C40—C39—C44—C45−119.5 (5)
C2—C1—C17—C1837.0 (3)C38—C39—C44—C4562.9 (7)
C32—C1—C17—C2282.6 (3)C35—O7—C38'—O8'6.4 (7)
C2—C1—C17—C22−148.0 (2)C35—O7—C38'—C39'−175.6 (4)
C22—C17—C18—C19−2.8 (4)O8'—C38'—C39'—C40'−171.8 (6)
C1—C17—C18—C19172.2 (2)O7—C38'—C39'—C40'10.5 (9)
C17—C18—C19—C200.3 (4)O8'—C38'—C39'—C44'10.9 (9)
C18—C19—C20—C212.9 (4)O7—C38'—C39'—C44'−166.8 (5)
C18—C19—C20—O4−179.7 (2)C38'—C39'—C40'—C41'−179.1 (5)
C23—O4—C20—C1986.6 (3)C44'—C39'—C40'—C41'−1.5 (7)
C23—O4—C20—C21−95.9 (3)O9'—N3'—C41'—C40'−178.7 (6)
C19—C20—C21—C22−3.3 (5)C44'—N3'—C41'—C40'−2.7 (7)
O4—C20—C21—C22179.2 (3)O9'—N3'—C41'—C43'63.7 (8)
C20—C21—C22—C170.6 (5)C44'—N3'—C41'—C43'−120.4 (6)
C18—C17—C22—C212.4 (5)O9'—N3'—C41'—C42'−58.0 (8)
C1—C17—C22—C21−172.9 (3)C44'—N3'—C41'—C42'118.0 (6)
C20—O4—C23—O5−6.1 (4)C39'—C40'—C41'—N3'2.6 (6)
C20—O4—C23—C24172.3 (2)C39'—C40'—C41'—C43'119.8 (5)
O5—C23—C24—C25−179.2 (3)C39'—C40'—C41'—C42'−117.1 (6)
O4—C23—C24—C252.4 (4)O9'—N3'—C44'—C46'−61.3 (9)
O5—C23—C24—C292.6 (4)C41'—N3'—C44'—C46'122.5 (7)
O4—C23—C24—C29−175.8 (2)O9'—N3'—C44'—C39'178.1 (6)
C23—C24—C25—C26−177.2 (2)C41'—N3'—C44'—C39'1.9 (7)
C29—C24—C25—C261.2 (3)O9'—N3'—C44'—C45'65.1 (8)
O6—N2—C26—C25177.9 (2)C41'—N3'—C44'—C45'−111.0 (7)
C29—N2—C26—C251.7 (3)C40'—C39'—C44'—C46'−118.9 (7)
O6—N2—C26—C27−62.8 (3)C38'—C39'—C44'—C46'58.7 (9)
C29—N2—C26—C27121.0 (2)C40'—C39'—C44'—N3'−0.2 (7)
O6—N2—C26—C2861.3 (3)C38'—C39'—C44'—N3'177.5 (5)
C29—N2—C26—C28−114.9 (2)C40'—C39'—C44'—C45'109.7 (7)
C24—C25—C26—N2−1.7 (3)C38'—C39'—C44'—C45'−72.6 (8)
C24—C25—C26—C27−118.7 (3)C52—C47—C48—C490.0 (4)
C24—C25—C26—C28114.0 (3)C47—C48—C49—C50−0.2 (4)
O6—N2—C29—C24−177.2 (2)C48—C49—C50—C510.4 (4)
C26—N2—C29—C24−1.1 (3)C49—C50—C51—C52−0.4 (5)
O6—N2—C29—C31−58.9 (3)C48—C47—C52—C510.0 (5)
C26—N2—C29—C31117.2 (3)C50—C51—C52—C470.2 (5)
O6—N2—C29—C3064.7 (3)C55i—C53—C54—C550.3 (6)
C26—N2—C29—C30−119.2 (2)C53—C54—C55—C53i−0.3 (6)
C25—C24—C29—N2−0.1 (3)C61—C56—C57—C58−3.3 (7)
C23—C24—C29—N2178.4 (2)C56—C57—C58—C590.9 (7)
C25—C24—C29—C31−115.7 (3)C57—C58—C59—C601.2 (7)
C23—C24—C29—C3162.8 (3)C58—C59—C60—C61−0.9 (8)
C25—C24—C29—C30115.3 (3)C59—C60—C61—C56−1.4 (8)
C23—C24—C29—C30−66.3 (3)C57—C56—C61—C603.5 (7)
Symmetry codes: (i) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
Cg1, Cg2, and Cg3 are the centroids of the C47–C52, C17–C22 and C56–C61 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1A···O6ii1.002.493.448 (3)160
C4—H4A···O9'iii0.952.443.165 (5)133
C25—H25A···O2iv0.952.573.358 (4)141
C37—H37A···O6ii0.952.573.442 (3)153
C57—H57A···O6v0.952.583.514 (8)168
C10—H10A···Cg10.952.843.752 (3)161
C12—H12A···Cg2v0.982.943.726 (3)138
C19—H19A···Cg1vi0.952.793.725 (3)169
C34—H34A···Cg30.952.783.547 (4)138
Symmetry codes: (ii) x−1, y−1, z; (iii) −x+1, −y, −z; (iv) x, y+1, z; (v) x, y−1, z; (vi) x+1, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg1, Cg2, and Cg3 are the centroids of the C47–C52, C17–C22 and C56–C61 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1A···O6i1.002.493.448 (3)160
C4—H4A···O9'ii0.952.443.165 (5)133
C25—H25A···O2iii0.952.573.358 (4)141
C37—H37A···O6i0.952.573.442 (3)153
C57—H57A···O6iv0.952.583.514 (8)168
C10—H10A···Cg10.952.843.752 (3)161
C12—H12A···Cg2iv0.982.943.726 (3)138
C19—H19A···Cg1v0.952.793.725 (3)169
C34—H34A···Cg30.952.783.547 (4)138
Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, −y, −z; (iii) x, y+1, z; (iv) x, y−1, z; (v) x+1, y+1, z.
references
References top

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Margraf, D., Schuetz, D., Prisner, T. F. & Bats, J. W. (2009). Acta Cryst. E65, o1784.

Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.