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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1681.
Published online 2010 June 16. doi:  10.1107/S1600536810022038
PMCID: PMC3006902

Diethyl 7,8,18,19-tetra­methyl-2,13-dioxo­hexa­cyclo­[10.10.2.03,24.05,10.014,23.016,21]tetra­cosa-5,7,9,16,18,20-hexa­ene-23,24-dicarboxyl­ate

Abstract

The asymmetric unit of the title compound, C30H34N4O6, contains two independent mol­ecules. In one independent mol­ecule, the two eth­oxy­carbonyl groups are each disordered over two conformations with occupancy ratios of 0.586 (2):0.414 (2) and 0.508 (2):0.492 (2). The crystal packing exhibits weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For the preparation and the crystal engineering studies on the title compound, see: Wang et al. (2006 [triangle]). For glycoluril and its derivatives, see: Freeman et al. (1981 [triangle]); Rebek (2005 [triangle]); Rowan et al. (1999 [triangle]); Wu et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1681-scheme1.jpg

Experimental

Crystal data

  • C30H34N4O6
  • M r = 546.61
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1681-efi1.jpg
  • a = 23.4988 (12) Å
  • b = 11.6005 (6) Å
  • c = 21.2685 (11) Å
  • β = 107.145 (1)°
  • V = 5540.1 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.16 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • 67299 measured reflections
  • 13767 independent reflections
  • 6896 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.116
  • S = 0.86
  • 13767 reflections
  • 809 parameters
  • 20 restraints
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022038/cv2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022038/cv2719Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Profressor An-Xin Wu for helpful discussions and Dr Xiang-Gao Meng for the X-ray data collection.

supplementary crystallographic information

Comment

Glycoluril and its derivatives are widely used as building blocks for studies of self-assembly in homogeneous solution (Freeman et al., 1981; Rebek, 2005; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives (Wang et al., 2006), here we report the structure of the title compound (I) (Fig. 1).

The asymmetric unit of (I) contains two independent molecules. In one independent molecule, two ethoxy carbonyl groups are disordered over two conformations each with ratios 0.586 (2)/0.414 (2) and 0.508 (2)/0.492 (2), respectively. The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

The title compound was synthesized according to the reported method (Wang et al.; 2006). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (4:1) solution of the title compound under 293 K.

Refinement

All H-atoms were positioned geometrically and constrained to ride on their parent atoms, with d(C—H) = 0.97 Å, Uĩso~ = 1.2U~eq~ (C) for CH~2~ and d(C—H) = 0.96 Å, Uĩso~ = 1.5U~eq~ (C) for CH~3~ atoms. In one independent molecule, two ethoxy carbonyl groups were treated as disordered over two conformations. The occupancies of the disordered positions C15A/ C15', C16A/ C16', O3A/O3' and O4A/O4' were refined to 0.508 (2) / 0.492 (2), while those for C19A/ C19', C20A/ C20', O5A/O5' and O6A/O6' were refined to 0.414 (2) / 0.586 (2).

Figures

Fig. 1.
A view of (I), showing one independent molecule with the atom-labelling scheme and 30% probability displacement ellipsoids.

Crystal data

C30H34N4O6F(000) = 2320
Mr = 546.61Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8852 reflections
a = 23.4988 (12) Åθ = 2.3–22.3°
b = 11.6005 (6) ŵ = 0.09 mm1
c = 21.2685 (11) ÅT = 298 K
β = 107.145 (1)°Block, colourless
V = 5540.1 (5) Å30.16 × 0.12 × 0.10 mm
Z = 8

Data collection

Bruker SMART 4K CCD area-detector diffractometer6896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
graphiteθmax = 28.3°, θmin = 1.8°
phi and ω scansh = −31→31
67299 measured reflectionsk = −15→15
13767 independent reflectionsl = −28→28

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.86w = 1/[σ2(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3
13767 reflections(Δ/σ)max = 0.002
809 parametersΔρmax = 0.17 e Å3
20 restraintsΔρmin = −0.18 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
O1A0.18810 (5)1.18390 (11)0.17156 (6)0.0609 (3)
O2A0.13366 (5)0.74461 (11)0.24984 (6)0.0633 (4)
N1A0.18396 (6)1.08832 (11)0.26470 (7)0.0445 (3)
N2A0.15077 (6)0.91667 (12)0.30754 (7)0.0454 (3)
N3A0.10001 (6)1.11326 (12)0.18400 (7)0.0479 (4)
N4A0.08583 (6)0.91354 (12)0.20740 (7)0.0494 (4)
C1A0.42409 (8)0.89433 (17)0.27568 (10)0.0669 (6)
H1A10.45000.83180.29530.100*
H1A20.44350.96620.29100.100*
H1A30.41500.89030.22870.100*
C2A0.38198 (9)0.67344 (17)0.32156 (10)0.0693 (6)
H2A10.38240.64910.27850.104*
H2A20.36330.61530.34080.104*
H2A30.42210.68510.34880.104*
C3A0.36724 (7)0.88602 (16)0.29477 (8)0.0489 (4)
C4A0.33249 (7)0.98434 (15)0.29049 (8)0.0483 (4)
H4A0.34511.05210.27530.058*
C5A0.28011 (7)0.98636 (14)0.30767 (8)0.0423 (4)
C6A0.26109 (7)0.88475 (15)0.33059 (8)0.0439 (4)
C7A0.29503 (7)0.78633 (15)0.33343 (8)0.0483 (4)
H7A0.28200.71810.34760.058*
C8A0.34788 (7)0.78424 (15)0.31616 (8)0.0486 (4)
C9A0.24609 (7)1.09810 (14)0.30318 (8)0.0479 (4)
H9A10.24821.12350.34730.058*
H9A20.26501.15650.28350.058*
C10A0.20665 (7)0.88039 (16)0.35484 (9)0.0528 (5)
H10C0.20190.80200.36830.063*
H10D0.21390.92890.39360.063*
C11A0.16072 (8)1.13303 (14)0.20341 (9)0.0459 (4)
C12A0.12450 (7)0.84661 (17)0.25404 (9)0.0482 (4)
C13A0.13984 (7)1.03574 (15)0.29051 (8)0.0451 (4)
C14A0.13113 (9)1.1126 (2)0.34619 (10)0.0588 (5)
C15A0.1006 (6)1.1414 (7)0.4389 (5)0.081 (3)0.508 (14)
H15C0.07011.19790.41950.098*0.508 (14)
H15D0.13741.18160.46040.098*0.508 (14)
C16A0.0821 (7)1.0681 (10)0.4872 (5)0.107 (3)0.508 (14)
H16G0.04331.03670.46670.160*0.508 (14)
H16H0.08111.11410.52430.160*0.508 (14)
H16I0.11011.00640.50160.160*0.508 (14)
O3A0.1475 (4)1.2123 (5)0.3507 (6)0.077 (2)0.508 (14)
O4A0.1090 (5)1.0641 (9)0.3884 (5)0.067 (2)0.508 (14)
C16'0.0627 (3)1.1133 (12)0.4607 (7)0.101 (4)0.492 (14)
H16F0.04131.16440.42640.151*0.492 (14)
H16E0.06341.14490.50270.151*0.492 (14)
H16D0.04321.03950.45520.151*0.492 (14)
C15'0.1248 (3)1.0992 (11)0.4576 (4)0.074 (2)0.492 (14)
H15E0.14381.17420.46170.088*0.492 (14)
H15F0.14711.05200.49430.088*0.492 (14)
O3'0.1234 (6)1.2148 (7)0.3406 (6)0.107 (3)0.492 (14)
O4'0.1264 (5)1.0456 (9)0.3960 (4)0.063 (2)0.492 (14)
C17A0.08463 (7)1.03234 (15)0.22728 (8)0.0476 (4)
C18A0.02543 (9)1.0647 (2)0.23998 (11)0.0618 (5)
C19A−0.0582 (5)0.9725 (15)0.2662 (6)0.076 (3)0.414 (14)
H19D−0.08410.91050.24400.091*0.414 (14)
H19C−0.07821.04510.25140.091*0.414 (14)
C20A−0.0465 (6)0.961 (2)0.3392 (5)0.125 (6)0.414 (14)
H20A−0.02680.88920.35370.187*0.414 (14)
H20B−0.08360.96310.34950.187*0.414 (14)
H20C−0.02171.02360.36100.187*0.414 (14)
O5A0.0137 (4)1.1627 (7)0.2523 (6)0.083 (2)0.414 (14)
O6A−0.0033 (5)0.9682 (9)0.2497 (6)0.076 (3)0.414 (14)
C19'−0.0466 (4)1.0092 (8)0.2890 (5)0.072 (2)0.586 (14)
H19E−0.07991.01840.24960.087*0.586 (14)
H19F−0.04271.07900.31510.087*0.586 (14)
C20'−0.0562 (4)0.9078 (7)0.3277 (5)0.084 (2)0.586 (14)
H20D−0.06290.84030.30030.126*0.586 (14)
H20E−0.09030.92130.34280.126*0.586 (14)
H20F−0.02170.89640.36480.126*0.586 (14)
O5'−0.0028 (4)1.1489 (7)0.2157 (5)0.108 (2)0.586 (14)
O6'0.0079 (3)0.9872 (6)0.2718 (4)0.0645 (18)0.586 (14)
C21A0.06619 (8)1.11686 (16)0.11404 (9)0.0600 (5)
H21C0.07581.18800.09550.072*
H21D0.02411.11920.11050.072*
C22A0.04665 (8)0.87020 (17)0.14544 (9)0.0606 (5)
H22C0.00680.89940.13970.073*
H22D0.04500.78680.14770.073*
C23A0.07681 (8)1.01776 (17)0.07294 (9)0.0543 (5)
C24A0.06599 (7)0.90349 (17)0.08606 (9)0.0542 (5)
C25A0.07319 (8)0.81895 (18)0.04264 (10)0.0629 (5)
H25A0.06510.74280.05070.075*
C26A0.09188 (8)0.8428 (2)−0.01213 (10)0.0657 (6)
C27A0.10430 (9)0.9561 (2)−0.02375 (10)0.0689 (6)
C28A0.09629 (8)1.04109 (19)0.01882 (9)0.0661 (5)
H28A0.10441.11720.01060.079*
C29A0.12856 (11)0.9883 (3)−0.08023 (11)0.1068 (9)
H29D0.12981.0707−0.08380.160*
H29E0.10320.9569−0.12050.160*
H29F0.16800.9576−0.07210.160*
C30A0.09864 (10)0.7452 (2)−0.05647 (11)0.0939 (8)
H30D0.07440.7602−0.10060.141*
H30F0.08620.6743−0.04130.141*
H30E0.13960.7391−0.05570.141*
O1B0.43937 (5)0.04574 (12)0.71998 (6)0.0632 (4)
O2B0.28886 (5)0.12011 (11)0.46037 (6)0.0611 (3)
O3B0.23181 (6)−0.17082 (13)0.54130 (7)0.0830 (5)
O4B0.27176 (5)−0.20261 (11)0.64928 (6)0.0589 (3)
O5B0.18946 (6)0.03919 (13)0.62346 (7)0.0790 (4)
O6B0.26075 (5)0.05723 (12)0.71918 (6)0.0662 (4)
N1B0.36696 (6)−0.07053 (12)0.65219 (6)0.0456 (3)
N2B0.32046 (6)−0.02124 (13)0.53878 (6)0.0471 (4)
N3B0.34505 (6)0.11166 (13)0.66635 (6)0.0463 (4)
N4B0.26966 (6)0.12751 (12)0.56039 (6)0.0454 (3)
C1B0.59664 (8)−0.2226 (2)0.59397 (11)0.0791 (6)
H1B10.6071−0.24000.64010.119*
H1B20.6215−0.16140.58680.119*
H1B30.6023−0.28990.57020.119*
C2B0.53769 (9)−0.16490 (19)0.45324 (10)0.0748 (6)
H2B10.5753−0.12650.46990.112*
H2B20.5147−0.12740.41370.112*
H2B30.5442−0.24390.44380.112*
C3B0.53237 (8)−0.18567 (15)0.57005 (10)0.0544 (5)
C4B0.49900 (8)−0.17902 (14)0.61356 (9)0.0514 (4)
H4B0.5180−0.19310.65780.062*
C5B0.43871 (7)−0.15249 (14)0.59491 (8)0.0460 (4)
C6B0.41070 (8)−0.12653 (14)0.52904 (9)0.0478 (4)
C7B0.44481 (8)−0.12908 (14)0.48547 (9)0.0530 (5)
H7B0.4267−0.10910.44180.064*
C8B0.50443 (8)−0.15993 (15)0.50415 (10)0.0535 (5)
C9B0.40622 (8)−0.16434 (16)0.64638 (9)0.0536 (5)
H9B10.3828−0.23450.63720.064*
H9B20.4358−0.17430.68880.064*
C10B0.34481 (8)−0.10271 (16)0.50137 (8)0.0548 (5)
H10A0.3372−0.07340.45690.066*
H10B0.3235−0.17510.49860.066*
C11B0.38948 (8)0.03153 (16)0.68311 (8)0.0466 (4)
C12B0.29294 (7)0.07911 (16)0.51412 (8)0.0458 (4)
C13B0.31232 (7)−0.05049 (15)0.60153 (8)0.0450 (4)
C14B0.26692 (8)−0.14919 (16)0.59342 (10)0.0539 (5)
C15B0.23022 (9)−0.2983 (2)0.64711 (10)0.0754 (6)
H15A0.1907−0.27610.62030.091*
H15B0.2282−0.31370.69120.091*
C16B0.24875 (11)−0.4051 (2)0.61965 (12)0.0959 (8)
H16A0.2461−0.39300.57420.144*
H16B0.2230−0.46750.62320.144*
H16C0.2891−0.42370.64380.144*
C17B0.29055 (7)0.06692 (15)0.62221 (8)0.0451 (4)
C18B0.24006 (9)0.05387 (16)0.65443 (10)0.0536 (5)
C19B0.21676 (9)0.0420 (2)0.75488 (11)0.0920 (8)
H19A0.18380.09500.73810.110*
H19B0.2013−0.03600.74900.110*
C20B0.24566 (12)0.0646 (2)0.82460 (11)0.0992 (8)
H20G0.27680.00930.84140.149*
H20H0.21690.05850.84840.149*
H20I0.26230.14090.82980.149*
C21B0.35170 (8)0.23038 (15)0.68850 (8)0.0552 (5)
H21A0.38590.23630.72730.066*
H21B0.31680.25300.70090.066*
C22B0.25941 (7)0.25230 (15)0.55949 (9)0.0539 (5)
H22A0.23780.27040.59070.065*
H22B0.23450.27420.51610.065*
C23B0.35967 (8)0.31235 (15)0.63671 (8)0.0486 (4)
C24B0.31593 (8)0.32328 (15)0.57615 (8)0.0488 (4)
C25B0.32564 (9)0.39956 (16)0.53058 (9)0.0572 (5)
H25B0.29650.40730.49030.069*
C26B0.37723 (9)0.46536 (16)0.54247 (10)0.0595 (5)
C27B0.42118 (8)0.45323 (15)0.60225 (10)0.0554 (5)
C28B0.41137 (8)0.37727 (15)0.64819 (9)0.0529 (5)
H28B0.44060.36940.68840.063*
C29B0.47928 (9)0.51749 (17)0.61727 (11)0.0770 (6)
H29A0.50190.50410.66220.116*
H29B0.47160.59850.61050.116*
H29C0.50140.49090.58870.116*
C30B0.38487 (11)0.5469 (2)0.48971 (11)0.0910 (7)
H30A0.41280.51470.46950.136*
H30B0.39940.61980.50930.136*
H30C0.34720.55780.45700.136*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0681 (8)0.0636 (8)0.0582 (8)−0.0060 (7)0.0300 (7)0.0106 (7)
O2A0.0638 (8)0.0445 (8)0.0857 (10)−0.0010 (7)0.0284 (7)0.0005 (7)
N1A0.0429 (8)0.0496 (9)0.0438 (8)−0.0020 (7)0.0170 (7)0.0057 (7)
N2A0.0436 (8)0.0477 (9)0.0480 (9)0.0007 (7)0.0182 (7)0.0055 (7)
N3A0.0464 (9)0.0530 (9)0.0445 (9)0.0031 (7)0.0137 (7)0.0044 (7)
N4A0.0472 (9)0.0493 (9)0.0520 (9)−0.0025 (7)0.0151 (7)−0.0024 (7)
C1A0.0556 (12)0.0763 (14)0.0759 (14)0.0014 (10)0.0303 (11)0.0031 (11)
C2A0.0734 (14)0.0653 (14)0.0774 (14)0.0149 (11)0.0349 (12)0.0068 (11)
C3A0.0444 (10)0.0584 (12)0.0435 (10)−0.0022 (9)0.0125 (8)−0.0014 (9)
C4A0.0465 (10)0.0502 (11)0.0491 (11)−0.0080 (9)0.0154 (9)0.0007 (8)
C5A0.0428 (10)0.0462 (10)0.0376 (9)−0.0026 (8)0.0113 (8)−0.0022 (8)
C6A0.0431 (10)0.0512 (11)0.0376 (9)0.0001 (8)0.0123 (8)0.0022 (8)
C7A0.0536 (11)0.0471 (11)0.0445 (10)−0.0025 (9)0.0150 (9)0.0054 (8)
C8A0.0493 (11)0.0541 (12)0.0429 (10)0.0053 (9)0.0146 (8)0.0014 (8)
C9A0.0463 (10)0.0500 (11)0.0476 (10)−0.0056 (8)0.0141 (8)−0.0017 (8)
C10A0.0523 (11)0.0596 (12)0.0500 (11)0.0023 (9)0.0207 (9)0.0126 (9)
C11A0.0516 (11)0.0429 (10)0.0481 (11)0.0023 (8)0.0226 (9)−0.0012 (8)
C12A0.0424 (10)0.0516 (12)0.0590 (12)−0.0040 (9)0.0278 (9)0.0033 (10)
C13A0.0453 (10)0.0485 (11)0.0453 (10)0.0009 (8)0.0195 (8)0.0017 (8)
C14A0.0588 (13)0.0670 (15)0.0558 (13)0.0052 (13)0.0251 (10)−0.0033 (12)
C15A0.098 (7)0.091 (6)0.070 (5)−0.001 (4)0.046 (5)−0.029 (4)
C16A0.122 (9)0.148 (9)0.064 (5)0.013 (5)0.049 (6)−0.004 (4)
O3A0.088 (4)0.048 (3)0.109 (5)−0.001 (2)0.053 (4)−0.018 (3)
O4A0.074 (6)0.074 (3)0.068 (3)−0.010 (3)0.044 (4)−0.015 (2)
C16'0.090 (5)0.125 (9)0.099 (8)0.006 (5)0.047 (5)−0.036 (6)
C15'0.075 (5)0.091 (7)0.060 (4)−0.009 (3)0.027 (4)−0.014 (3)
O3'0.173 (9)0.084 (4)0.080 (4)0.052 (4)0.060 (6)0.002 (3)
O4'0.066 (5)0.087 (4)0.046 (3)−0.005 (3)0.034 (3)−0.012 (2)
C17A0.0428 (10)0.0525 (11)0.0505 (11)0.0024 (8)0.0184 (9)0.0008 (9)
C18A0.0478 (12)0.0689 (15)0.0725 (15)0.0086 (11)0.0235 (11)0.0072 (13)
C19A0.048 (5)0.108 (9)0.085 (7)0.003 (4)0.038 (5)0.008 (5)
C20A0.065 (5)0.23 (2)0.081 (6)−0.023 (10)0.028 (5)0.033 (9)
O5A0.071 (4)0.070 (3)0.122 (6)0.018 (2)0.050 (4)−0.003 (4)
O6A0.056 (4)0.098 (5)0.086 (6)−0.005 (3)0.038 (4)−0.004 (3)
C19'0.052 (4)0.094 (5)0.082 (6)0.012 (3)0.038 (4)0.008 (4)
C20'0.060 (5)0.086 (4)0.115 (6)−0.003 (3)0.041 (4)0.025 (3)
O5'0.089 (4)0.109 (4)0.150 (6)0.050 (3)0.071 (4)0.057 (4)
O6'0.046 (3)0.070 (3)0.088 (4)0.0134 (19)0.036 (3)0.025 (3)
C21A0.0614 (12)0.0628 (13)0.0524 (12)0.0090 (10)0.0114 (10)0.0075 (10)
C22A0.0513 (11)0.0633 (13)0.0652 (13)−0.0107 (9)0.0143 (10)−0.0087 (10)
C23A0.0453 (10)0.0653 (13)0.0478 (11)0.0060 (9)0.0068 (9)0.0010 (10)
C24A0.0407 (10)0.0660 (14)0.0523 (12)−0.0004 (9)0.0080 (9)−0.0042 (10)
C25A0.0504 (12)0.0681 (14)0.0630 (13)0.0014 (10)0.0058 (10)−0.0080 (11)
C26A0.0478 (11)0.0940 (17)0.0493 (12)0.0139 (11)0.0050 (10)−0.0123 (12)
C27A0.0582 (13)0.0947 (18)0.0524 (13)0.0076 (12)0.0142 (10)−0.0006 (12)
C28A0.0643 (13)0.0793 (15)0.0513 (12)0.0026 (11)0.0117 (10)0.0072 (11)
C29A0.112 (2)0.151 (3)0.0690 (16)0.0029 (18)0.0449 (15)−0.0001 (16)
C30A0.0838 (16)0.117 (2)0.0767 (16)0.0254 (15)0.0166 (13)−0.0248 (14)
O1B0.0422 (7)0.0888 (10)0.0525 (8)−0.0113 (7)0.0046 (6)0.0012 (7)
O2B0.0693 (8)0.0764 (9)0.0379 (7)0.0098 (7)0.0162 (6)0.0073 (6)
O3B0.0718 (9)0.0992 (12)0.0616 (9)−0.0304 (8)−0.0060 (8)0.0069 (8)
O4B0.0554 (8)0.0702 (9)0.0515 (8)−0.0185 (6)0.0164 (6)0.0035 (7)
O5B0.0440 (8)0.1239 (13)0.0725 (10)−0.0137 (8)0.0222 (7)−0.0035 (9)
O6B0.0534 (8)0.1029 (11)0.0513 (8)0.0017 (7)0.0292 (7)0.0122 (7)
N1B0.0379 (8)0.0579 (9)0.0410 (8)−0.0008 (7)0.0115 (7)0.0014 (7)
N2B0.0475 (8)0.0596 (10)0.0356 (8)0.0057 (7)0.0143 (7)0.0016 (7)
N3B0.0423 (8)0.0590 (10)0.0383 (8)−0.0057 (7)0.0129 (7)−0.0020 (7)
N4B0.0412 (8)0.0561 (10)0.0398 (8)0.0019 (7)0.0135 (7)0.0012 (7)
C1B0.0537 (13)0.0992 (18)0.0872 (16)0.0014 (12)0.0252 (12)−0.0178 (13)
C2B0.0789 (15)0.0823 (15)0.0762 (15)−0.0032 (12)0.0431 (12)−0.0137 (12)
C3B0.0504 (11)0.0492 (11)0.0664 (13)−0.0030 (9)0.0216 (10)−0.0132 (10)
C4B0.0500 (11)0.0502 (11)0.0535 (11)−0.0012 (9)0.0145 (9)−0.0032 (9)
C5B0.0477 (10)0.0437 (10)0.0482 (11)−0.0008 (8)0.0166 (9)−0.0007 (8)
C6B0.0522 (11)0.0453 (10)0.0475 (11)−0.0007 (8)0.0170 (9)−0.0062 (8)
C7B0.0673 (13)0.0488 (11)0.0470 (11)−0.0003 (9)0.0229 (10)−0.0071 (8)
C8B0.0611 (12)0.0443 (11)0.0622 (13)−0.0059 (9)0.0293 (10)−0.0128 (9)
C9B0.0479 (10)0.0641 (12)0.0482 (11)0.0050 (9)0.0132 (9)0.0087 (9)
C10B0.0584 (12)0.0650 (13)0.0406 (10)0.0036 (10)0.0139 (9)−0.0066 (9)
C11B0.0409 (10)0.0682 (13)0.0334 (9)−0.0075 (10)0.0153 (8)0.0048 (9)
C12B0.0392 (10)0.0614 (12)0.0352 (10)−0.0035 (9)0.0087 (8)−0.0008 (9)
C13B0.0380 (9)0.0580 (11)0.0381 (10)−0.0041 (8)0.0100 (8)0.0013 (8)
C14B0.0461 (11)0.0640 (13)0.0482 (12)−0.0051 (9)0.0088 (9)0.0003 (10)
C15B0.0674 (13)0.0936 (17)0.0682 (14)−0.0333 (12)0.0246 (11)0.0037 (12)
C16B0.112 (2)0.0737 (17)0.0967 (19)−0.0279 (15)0.0226 (16)−0.0022 (14)
C17B0.0378 (9)0.0603 (11)0.0389 (10)−0.0037 (8)0.0139 (8)0.0000 (8)
C18B0.0462 (11)0.0665 (13)0.0525 (12)−0.0008 (10)0.0215 (10)0.0026 (10)
C19B0.0712 (15)0.150 (2)0.0721 (16)0.0005 (15)0.0476 (13)0.0227 (15)
C20B0.134 (2)0.109 (2)0.0802 (18)0.0127 (16)0.0710 (17)0.0114 (14)
C21B0.0626 (12)0.0641 (13)0.0420 (10)−0.0079 (10)0.0202 (9)−0.0094 (9)
C22B0.0473 (11)0.0665 (13)0.0497 (11)0.0079 (9)0.0172 (9)0.0000 (9)
C23B0.0567 (11)0.0522 (11)0.0412 (10)−0.0011 (9)0.0211 (9)−0.0074 (8)
C24B0.0518 (11)0.0520 (11)0.0455 (11)0.0042 (9)0.0190 (9)−0.0049 (9)
C25B0.0654 (13)0.0560 (12)0.0503 (11)0.0063 (10)0.0173 (10)0.0013 (9)
C26B0.0751 (14)0.0485 (12)0.0605 (13)−0.0005 (10)0.0285 (11)0.0000 (10)
C27B0.0637 (12)0.0450 (11)0.0616 (13)−0.0013 (9)0.0249 (11)−0.0067 (9)
C28B0.0603 (12)0.0511 (11)0.0478 (11)0.0000 (9)0.0167 (9)−0.0068 (9)
C29B0.0784 (15)0.0599 (14)0.0920 (16)−0.0143 (11)0.0240 (13)0.0021 (12)
C30B0.1126 (19)0.0788 (16)0.0806 (16)−0.0167 (14)0.0272 (14)0.0201 (13)

Geometric parameters (Å, °)

O1A—C11A1.2160 (18)C27A—C28A1.388 (3)
O2A—C12A1.211 (2)C27A—C29A1.520 (3)
N1A—C11A1.359 (2)C28A—H28A0.9300
N1A—C13A1.4435 (19)C29A—H29D0.9600
N1A—C9A1.452 (2)C29A—H29E0.9600
N2A—C12A1.386 (2)C29A—H29F0.9600
N2A—C13A1.432 (2)C30A—H30D0.9600
N2A—C10A1.461 (2)C30A—H30F0.9600
N3A—C11A1.382 (2)C30A—H30E0.9600
N3A—C17A1.434 (2)O1B—C11B1.2143 (19)
N3A—C21A1.466 (2)O2B—C12B1.2155 (19)
N4A—C12A1.371 (2)O3B—C14B1.197 (2)
N4A—C17A1.444 (2)O4B—C14B1.315 (2)
N4A—C22A1.457 (2)O4B—C15B1.470 (2)
C1A—C3A1.509 (2)O5B—C18B1.189 (2)
C1A—H1A10.9600O6B—C18B1.319 (2)
C1A—H1A20.9600O6B—C19B1.463 (2)
C1A—H1A30.9600N1B—C11B1.382 (2)
C2A—C8A1.501 (2)N1B—C13B1.431 (2)
C2A—H2A10.9600N1B—C9B1.455 (2)
C2A—H2A20.9600N2B—C12B1.360 (2)
C2A—H2A30.9600N2B—C13B1.4434 (19)
C3A—C8A1.389 (2)N2B—C10B1.457 (2)
C3A—C4A1.390 (2)N3B—C11B1.365 (2)
C4A—C5A1.383 (2)N3B—C17B1.443 (2)
C4A—H4A0.9300N3B—C21B1.449 (2)
C5A—C6A1.398 (2)N4B—C12B1.379 (2)
C5A—C9A1.511 (2)N4B—C17B1.443 (2)
C6A—C7A1.384 (2)N4B—C22B1.467 (2)
C6A—C10A1.515 (2)C1B—C3B1.507 (3)
C7A—C8A1.395 (2)C1B—H1B10.9600
C7A—H7A0.9300C1B—H1B20.9600
C9A—H9A10.9700C1B—H1B30.9600
C9A—H9A20.9700C2B—C8B1.512 (2)
C10A—H10C0.9700C2B—H2B10.9600
C10A—H10D0.9700C2B—H2B20.9600
C13A—C14A1.543 (2)C2B—H2B30.9600
C13A—C17A1.570 (2)C3B—C4B1.380 (2)
C14A—O3'1.200 (7)C3B—C8B1.394 (3)
C14A—O3A1.213 (6)C4B—C5B1.388 (2)
C14A—O4A1.291 (7)C4B—H4B0.9300
C14A—O4'1.346 (7)C5B—C6B1.394 (2)
C15A—O4A1.456 (7)C5B—C9B1.514 (2)
C15A—C16A1.494 (8)C6B—C7B1.393 (2)
C15A—H15C0.9700C6B—C10B1.511 (2)
C15A—H15D0.9700C7B—C8B1.386 (2)
C16A—H16G0.9600C7B—H7B0.9300
C16A—H16H0.9600C9B—H9B10.9700
C16A—H16I0.9600C9B—H9B20.9700
C16'—C15'1.490 (8)C10B—H10A0.9700
C16'—H16F0.9600C10B—H10B0.9700
C16'—H16E0.9600C13B—C14B1.540 (2)
C16'—H16D0.9600C13B—C17B1.563 (2)
C15'—O4'1.461 (7)C15B—C16B1.488 (3)
C15'—H15E0.9700C15B—H15A0.9700
C15'—H15F0.9700C15B—H15B0.9700
C17A—C18A1.540 (2)C16B—H16A0.9600
C18A—O5'1.208 (5)C16B—H16B0.9600
C18A—O5A1.216 (6)C16B—H16C0.9600
C18A—O6'1.264 (5)C17B—C18B1.543 (2)
C18A—O6A1.355 (8)C19B—C20B1.461 (3)
C19A—O6A1.434 (8)C19B—H19A0.9700
C19A—C20A1.500 (9)C19B—H19B0.9700
C19A—H19D0.9700C20B—H20G0.9600
C19A—H19C0.9700C20B—H20H0.9600
C20A—H20A0.9600C20B—H20I0.9600
C20A—H20B0.9600C21B—C23B1.508 (2)
C20A—H20C0.9600C21B—H21A0.9700
C19'—O6'1.455 (6)C21B—H21B0.9700
C19'—C20'1.491 (7)C22B—C24B1.513 (2)
C19'—H19E0.9700C22B—H22A0.9700
C19'—H19F0.9700C22B—H22B0.9700
C20'—H20D0.9600C23B—C28B1.388 (2)
C20'—H20E0.9600C23B—C24B1.397 (2)
C20'—H20F0.9600C24B—C25B1.380 (2)
C21A—C23A1.509 (2)C25B—C26B1.391 (3)
C21A—H21C0.9700C25B—H25B0.9300
C21A—H21D0.9700C26B—C27B1.389 (3)
C22A—C24A1.513 (2)C26B—C30B1.519 (3)
C22A—H22C0.9700C27B—C28B1.385 (2)
C22A—H22D0.9700C27B—C29B1.505 (3)
C23A—C28A1.385 (2)C28B—H28B0.9300
C23A—C24A1.394 (3)C29B—H29A0.9600
C24A—C25A1.391 (2)C29B—H29B0.9600
C25A—C26A1.389 (3)C29B—H29C0.9600
C25A—H25A0.9300C30B—H30A0.9600
C26A—C27A1.385 (3)C30B—H30B0.9600
C26A—C30A1.512 (3)C30B—H30C0.9600
C11A—N1A—C13A113.29 (14)C27A—C29A—H29D109.5
C11A—N1A—C9A124.30 (14)C27A—C29A—H29E109.5
C13A—N1A—C9A122.28 (13)H29D—C29A—H29E109.5
C12A—N2A—C13A110.77 (14)C27A—C29A—H29F109.5
C12A—N2A—C10A119.25 (15)H29D—C29A—H29F109.5
C13A—N2A—C10A120.65 (14)H29E—C29A—H29F109.5
C11A—N3A—C17A110.49 (14)C26A—C30A—H30D109.5
C11A—N3A—C21A120.08 (14)C26A—C30A—H30F109.5
C17A—N3A—C21A120.43 (14)H30D—C30A—H30F109.5
C12A—N4A—C17A113.23 (14)C26A—C30A—H30E109.5
C12A—N4A—C22A124.49 (15)H30D—C30A—H30E109.5
C17A—N4A—C22A122.17 (14)H30F—C30A—H30E109.5
C3A—C1A—H1A1109.5C14B—O4B—C15B116.61 (14)
C3A—C1A—H1A2109.5C18B—O6B—C19B116.05 (15)
H1A1—C1A—H1A2109.5C11B—N1B—C13B110.60 (14)
C3A—C1A—H1A3109.5C11B—N1B—C9B121.18 (14)
H1A1—C1A—H1A3109.5C13B—N1B—C9B120.54 (14)
H1A2—C1A—H1A3109.5C12B—N2B—C13B112.36 (13)
C8A—C2A—H2A1109.5C12B—N2B—C10B124.30 (14)
C8A—C2A—H2A2109.5C13B—N2B—C10B122.21 (14)
H2A1—C2A—H2A2109.5C11B—N3B—C17B112.89 (14)
C8A—C2A—H2A3109.5C11B—N3B—C21B124.17 (15)
H2A1—C2A—H2A3109.5C17B—N3B—C21B122.92 (14)
H2A2—C2A—H2A3109.5C12B—N4B—C17B110.61 (14)
C8A—C3A—C4A118.43 (15)C12B—N4B—C22B119.41 (14)
C8A—C3A—C1A122.93 (16)C17B—N4B—C22B120.20 (13)
C4A—C3A—C1A118.65 (16)C3B—C1B—H1B1109.5
C5A—C4A—C3A123.22 (16)C3B—C1B—H1B2109.5
C5A—C4A—H4A118.4H1B1—C1B—H1B2109.5
C3A—C4A—H4A118.4C3B—C1B—H1B3109.5
C4A—C5A—C6A118.58 (15)H1B1—C1B—H1B3109.5
C4A—C5A—C9A119.55 (15)H1B2—C1B—H1B3109.5
C6A—C5A—C9A121.85 (14)C8B—C2B—H2B1109.5
C7A—C6A—C5A118.13 (15)C8B—C2B—H2B2109.5
C7A—C6A—C10A119.43 (15)H2B1—C2B—H2B2109.5
C5A—C6A—C10A122.39 (15)C8B—C2B—H2B3109.5
C6A—C7A—C8A123.30 (16)H2B1—C2B—H2B3109.5
C6A—C7A—H7A118.3H2B2—C2B—H2B3109.5
C8A—C7A—H7A118.3C4B—C3B—C8B118.02 (17)
C3A—C8A—C7A118.31 (16)C4B—C3B—C1B120.04 (18)
C3A—C8A—C2A122.26 (16)C8B—C3B—C1B121.92 (17)
C7A—C8A—C2A119.43 (16)C3B—C4B—C5B123.67 (17)
N1A—C9A—C5A113.18 (13)C3B—C4B—H4B118.2
N1A—C9A—H9A1108.9C5B—C4B—H4B118.2
C5A—C9A—H9A1108.9C4B—C5B—C6B118.33 (16)
N1A—C9A—H9A2108.9C4B—C5B—C9B117.57 (15)
C5A—C9A—H9A2108.9C6B—C5B—C9B123.85 (15)
H9A1—C9A—H9A2107.8C7B—C6B—C5B118.06 (16)
N2A—C10A—C6A115.70 (13)C7B—C6B—C10B117.99 (16)
N2A—C10A—H10C108.4C5B—C6B—C10B123.84 (15)
C6A—C10A—H10C108.4C8B—C7B—C6B123.10 (17)
N2A—C10A—H10D108.4C8B—C7B—H7B118.5
C6A—C10A—H10D108.4C6B—C7B—H7B118.5
H10C—C10A—H10D107.4C7B—C8B—C3B118.72 (17)
O1A—C11A—N1A126.20 (16)C7B—C8B—C2B119.80 (18)
O1A—C11A—N3A125.68 (16)C3B—C8B—C2B121.48 (18)
N1A—C11A—N3A108.10 (14)N1B—C9B—C5B117.44 (14)
O2A—C12A—N4A126.46 (18)N1B—C9B—H9B1107.9
O2A—C12A—N2A125.99 (18)C5B—C9B—H9B1107.9
N4A—C12A—N2A107.54 (16)N1B—C9B—H9B2107.9
N2A—C13A—N1A114.10 (13)C5B—C9B—H9B2107.9
N2A—C13A—C14A114.70 (15)H9B1—C9B—H9B2107.2
N1A—C13A—C14A108.67 (14)N2B—C10B—C6B115.36 (14)
N2A—C13A—C17A103.51 (13)N2B—C10B—H10A108.4
N1A—C13A—C17A100.93 (12)C6B—C10B—H10A108.4
C14A—C13A—C17A114.13 (14)N2B—C10B—H10B108.4
O3'—C14A—O4A114.8 (7)C6B—C10B—H10B108.4
O3A—C14A—O4A122.9 (7)H10A—C10B—H10B107.5
O3'—C14A—O4'127.2 (7)O1B—C11B—N3B126.51 (18)
O3A—C14A—O4'125.9 (8)O1B—C11B—N1B125.81 (18)
O3'—C14A—C13A123.0 (6)N3B—C11B—N1B107.65 (15)
O3A—C14A—C13A120.1 (5)O2B—C12B—N2B126.48 (16)
O4A—C14A—C13A117.0 (5)O2B—C12B—N4B125.03 (17)
O4'—C14A—C13A109.3 (5)N2B—C12B—N4B108.48 (14)
O4A—C15A—C16A106.7 (7)N1B—C13B—N2B113.60 (13)
O4A—C15A—H15C110.4N1B—C13B—C14B113.69 (14)
C16A—C15A—H15C110.4N2B—C13B—C14B110.33 (14)
O4A—C15A—H15D110.4N1B—C13B—C17B103.02 (13)
C16A—C15A—H15D110.4N2B—C13B—C17B101.48 (13)
H15C—C15A—H15D108.6C14B—C13B—C17B113.95 (13)
C14A—O4A—C15A114.5 (8)O3B—C14B—O4B126.18 (17)
C15'—C16'—H16F109.5O3B—C14B—C13B121.69 (17)
C15'—C16'—H16E109.5O4B—C14B—C13B112.13 (15)
H16F—C16'—H16E109.5O4B—C15B—C16B111.87 (17)
C15'—C16'—H16D109.5O4B—C15B—H15A109.2
H16F—C16'—H16D109.5C16B—C15B—H15A109.2
H16E—C16'—H16D109.5O4B—C15B—H15B109.2
O4'—C15'—C16'111.8 (7)C16B—C15B—H15B109.2
O4'—C15'—H15E109.3H15A—C15B—H15B107.9
C16'—C15'—H15E109.3C15B—C16B—H16A109.5
O4'—C15'—H15F109.3C15B—C16B—H16B109.5
C16'—C15'—H15F109.3H16A—C16B—H16B109.5
H15E—C15'—H15F107.9C15B—C16B—H16C109.5
C14A—O4'—C15'119.3 (8)H16A—C16B—H16C109.5
N3A—C17A—N4A113.99 (13)H16B—C16B—H16C109.5
N3A—C17A—C18A111.39 (15)N3B—C17B—N4B114.56 (13)
N4A—C17A—C18A112.37 (15)N3B—C17B—C18B113.43 (14)
N3A—C17A—C13A103.45 (13)N4B—C17B—C18B110.67 (14)
N4A—C17A—C13A101.09 (13)N3B—C17B—C13B101.25 (12)
C18A—C17A—C13A113.87 (15)N4B—C17B—C13B102.69 (13)
O5'—C18A—O6'125.4 (5)C18B—C17B—C13B113.46 (14)
O5A—C18A—O6'114.8 (6)O5B—C18B—O6B125.66 (16)
O5'—C18A—O6A119.9 (7)O5B—C18B—C17B122.84 (17)
O5A—C18A—O6A125.8 (7)O6B—C18B—C17B111.46 (16)
O5'—C18A—C17A122.2 (4)C20B—C19B—O6B108.48 (18)
O5A—C18A—C17A122.6 (5)C20B—C19B—H19A110.0
O6'—C18A—C17A112.0 (4)O6B—C19B—H19A110.0
O6A—C18A—C17A110.0 (5)C20B—C19B—H19B110.0
O6A—C19A—C20A110.2 (8)O6B—C19B—H19B110.0
O6A—C19A—H19D109.6H19A—C19B—H19B108.4
C20A—C19A—H19D109.6C19B—C20B—H20G109.5
O6A—C19A—H19C109.6C19B—C20B—H20H109.5
C20A—C19A—H19C109.6H20G—C20B—H20H109.5
H19D—C19A—H19C108.1C19B—C20B—H20I109.5
C18A—O6A—C19A122.3 (10)H20G—C20B—H20I109.5
O6'—C19'—C20'106.8 (6)H20H—C20B—H20I109.5
O6'—C19'—H19E110.4N3B—C21B—C23B112.75 (14)
C20'—C19'—H19E110.4N3B—C21B—H21A109.0
O6'—C19'—H19F110.4C23B—C21B—H21A109.0
C20'—C19'—H19F110.4N3B—C21B—H21B109.0
H19E—C19'—H19F108.6C23B—C21B—H21B109.0
C19'—C20'—H20D109.5H21A—C21B—H21B107.8
C19'—C20'—H20E109.5N4B—C22B—C24B113.86 (14)
H20D—C20'—H20E109.5N4B—C22B—H22A108.8
C19'—C20'—H20F109.5C24B—C22B—H22A108.8
H20D—C20'—H20F109.5N4B—C22B—H22B108.8
H20E—C20'—H20F109.5C24B—C22B—H22B108.8
C18A—O6'—C19'117.4 (6)H22A—C22B—H22B107.7
N3A—C21A—C23A115.69 (15)C28B—C23B—C24B118.74 (16)
N3A—C21A—H21C108.4C28B—C23B—C21B120.28 (16)
C23A—C21A—H21C108.4C24B—C23B—C21B120.97 (16)
N3A—C21A—H21D108.4C25B—C24B—C23B118.46 (17)
C23A—C21A—H21D108.4C25B—C24B—C22B120.00 (16)
H21C—C21A—H21D107.4C23B—C24B—C22B121.53 (16)
N4A—C22A—C24A113.69 (14)C24B—C25B—C26B122.67 (18)
N4A—C22A—H22C108.8C24B—C25B—H25B118.7
C24A—C22A—H22C108.8C26B—C25B—H25B118.7
N4A—C22A—H22D108.8C27B—C26B—C25B118.94 (17)
C24A—C22A—H22D108.8C27B—C26B—C30B121.43 (19)
H22C—C22A—H22D107.7C25B—C26B—C30B119.61 (19)
C28A—C23A—C24A118.49 (18)C28B—C27B—C26B118.48 (17)
C28A—C23A—C21A118.96 (18)C28B—C27B—C29B119.65 (18)
C24A—C23A—C21A122.52 (17)C26B—C27B—C29B121.84 (18)
C25A—C24A—C23A118.19 (18)C27B—C28B—C23B122.69 (17)
C25A—C24A—C22A119.97 (18)C27B—C28B—H28B118.7
C23A—C24A—C22A121.84 (17)C23B—C28B—H28B118.7
C26A—C25A—C24A123.2 (2)C27B—C29B—H29A109.5
C26A—C25A—H25A118.4C27B—C29B—H29B109.5
C24A—C25A—H25A118.4H29A—C29B—H29B109.5
C27A—C26A—C25A118.32 (19)C27B—C29B—H29C109.5
C27A—C26A—C30A122.2 (2)H29A—C29B—H29C109.5
C25A—C26A—C30A119.4 (2)H29B—C29B—H29C109.5
C26A—C27A—C28A118.79 (19)C26B—C30B—H30A109.5
C26A—C27A—C29A121.4 (2)C26B—C30B—H30B109.5
C28A—C27A—C29A119.7 (2)H30A—C30B—H30B109.5
C23A—C28A—C27A123.0 (2)C26B—C30B—H30C109.5
C23A—C28A—H28A118.5H30A—C30B—H30C109.5
C27A—C28A—H28A118.5H30B—C30B—H30C109.5
C8A—C3A—C4A—C5A1.3 (3)N4A—C22A—C24A—C23A−53.5 (2)
C1A—C3A—C4A—C5A−179.06 (16)C23A—C24A—C25A—C26A1.5 (3)
C3A—C4A—C5A—C6A0.1 (2)C22A—C24A—C25A—C26A−178.75 (16)
C3A—C4A—C5A—C9A178.31 (15)C24A—C25A—C26A—C27A0.4 (3)
C4A—C5A—C6A—C7A−1.5 (2)C24A—C25A—C26A—C30A179.80 (17)
C9A—C5A—C6A—C7A−179.68 (15)C25A—C26A—C27A—C28A−1.4 (3)
C4A—C5A—C6A—C10A175.81 (15)C30A—C26A—C27A—C28A179.23 (18)
C9A—C5A—C6A—C10A−2.3 (2)C25A—C26A—C27A—C29A176.23 (18)
C5A—C6A—C7A—C8A1.7 (2)C30A—C26A—C27A—C29A−3.1 (3)
C10A—C6A—C7A—C8A−175.76 (15)C24A—C23A—C28A—C27A1.4 (3)
C4A—C3A—C8A—C7A−1.2 (2)C21A—C23A—C28A—C27A−176.58 (17)
C1A—C3A—C8A—C7A179.18 (16)C26A—C27A—C28A—C23A0.5 (3)
C4A—C3A—C8A—C2A179.21 (16)C29A—C27A—C28A—C23A−177.18 (19)
C1A—C3A—C8A—C2A−0.5 (3)C8B—C3B—C4B—C5B2.6 (3)
C6A—C7A—C8A—C3A−0.3 (3)C1B—C3B—C4B—C5B−176.01 (17)
C6A—C7A—C8A—C2A179.36 (16)C3B—C4B—C5B—C6B−2.7 (3)
C11A—N1A—C9A—C5A−106.97 (17)C3B—C4B—C5B—C9B171.81 (16)
C13A—N1A—C9A—C5A77.30 (18)C4B—C5B—C6B—C7B0.2 (2)
C4A—C5A—C9A—N1A126.93 (16)C9B—C5B—C6B—C7B−173.89 (16)
C6A—C5A—C9A—N1A−54.9 (2)C4B—C5B—C6B—C10B176.46 (16)
C12A—N2A—C10A—C6A71.0 (2)C9B—C5B—C6B—C10B2.3 (3)
C13A—N2A—C10A—C6A−72.5 (2)C5B—C6B—C7B—C8B2.3 (3)
C7A—C6A—C10A—N2A−124.46 (17)C10B—C6B—C7B—C8B−174.17 (16)
C5A—C6A—C10A—N2A58.2 (2)C6B—C7B—C8B—C3B−2.4 (3)
C13A—N1A—C11A—O1A178.27 (16)C6B—C7B—C8B—C2B177.66 (16)
C9A—N1A—C11A—O1A2.2 (3)C4B—C3B—C8B—C7B0.0 (3)
C13A—N1A—C11A—N3A−0.24 (18)C1B—C3B—C8B—C7B178.54 (17)
C9A—N1A—C11A—N3A−176.31 (14)C4B—C3B—C8B—C2B179.91 (16)
C17A—N3A—C11A—O1A168.77 (16)C1B—C3B—C8B—C2B−1.5 (3)
C21A—N3A—C11A—O1A21.5 (3)C11B—N1B—C9B—C5B−76.6 (2)
C17A—N3A—C11A—N1A−12.71 (18)C13B—N1B—C9B—C5B70.0 (2)
C21A—N3A—C11A—N1A−159.99 (14)C4B—C5B—C9B—N1B134.07 (16)
C17A—N4A—C12A—O2A179.59 (16)C6B—C5B—C9B—N1B−51.8 (2)
C22A—N4A—C12A—O2A3.3 (3)C12B—N2B—C10B—C6B120.76 (17)
C17A—N4A—C12A—N2A0.43 (18)C13B—N2B—C10B—C6B−72.4 (2)
C22A—N4A—C12A—N2A−175.90 (14)C7B—C6B—C10B—N2B−135.78 (16)
C13A—N2A—C12A—O2A167.42 (16)C5B—C6B—C10B—N2B48.0 (2)
C10A—N2A—C12A—O2A20.6 (2)C17B—N3B—C11B—O1B−179.01 (15)
C13A—N2A—C12A—N4A−13.43 (17)C21B—N3B—C11B—O1B2.8 (3)
C10A—N2A—C12A—N4A−160.29 (13)C17B—N3B—C11B—N1B−0.94 (17)
C12A—N2A—C13A—N1A−89.10 (16)C21B—N3B—C11B—N1B−179.15 (13)
C10A—N2A—C13A—N1A57.23 (19)C13B—N1B—C11B—O1B−166.92 (15)
C12A—N2A—C13A—C14A144.62 (15)C9B—N1B—C11B—O1B−17.4 (2)
C10A—N2A—C13A—C14A−69.05 (19)C13B—N1B—C11B—N3B14.99 (17)
C12A—N2A—C13A—C17A19.63 (16)C9B—N1B—C11B—N3B164.52 (13)
C10A—N2A—C13A—C17A165.96 (13)C13B—N2B—C12B—O2B−174.47 (16)
C11A—N1A—C13A—N2A121.71 (15)C10B—N2B—C12B—O2B−6.5 (3)
C9A—N1A—C13A—N2A−62.13 (19)C13B—N2B—C12B—N4B5.16 (18)
C11A—N1A—C13A—C14A−108.92 (16)C10B—N2B—C12B—N4B173.16 (14)
C9A—N1A—C13A—C14A67.24 (19)C17B—N4B—C12B—O2B−170.80 (16)
C11A—N1A—C13A—C17A11.40 (17)C22B—N4B—C12B—O2B−24.8 (2)
C9A—N1A—C13A—C17A−172.44 (14)C17B—N4B—C12B—N2B9.56 (18)
N2A—C13A—C14A—O3'177.6 (8)C22B—N4B—C12B—N2B155.54 (14)
N1A—C13A—C14A—O3'48.6 (9)C11B—N1B—C13B—N2B87.41 (16)
C17A—C13A—C14A—O3'−63.2 (9)C9B—N1B—C13B—N2B−62.35 (19)
N2A—C13A—C14A—O3A147.2 (6)C11B—N1B—C13B—C14B−145.31 (14)
N1A—C13A—C14A—O3A18.2 (6)C9B—N1B—C13B—C14B64.94 (19)
C17A—C13A—C14A—O3A−93.6 (6)C11B—N1B—C13B—C17B−21.49 (16)
N2A—C13A—C14A—O4A−29.2 (7)C9B—N1B—C13B—C17B−171.25 (13)
N1A—C13A—C14A—O4A−158.3 (6)C12B—N2B—C13B—N1B−125.86 (15)
C17A—C13A—C14A—O4A90.0 (7)C10B—N2B—C13B—N1B65.85 (19)
N2A—C13A—C14A—O4'−9.8 (6)C12B—N2B—C13B—C14B105.12 (16)
N1A—C13A—C14A—O4'−138.9 (6)C10B—N2B—C13B—C14B−63.17 (19)
C17A—C13A—C14A—O4'109.4 (6)C12B—N2B—C13B—C17B−16.01 (17)
O3'—C14A—O4A—C15A−23.4 (12)C10B—N2B—C13B—C17B175.70 (13)
O3A—C14A—O4A—C15A4.9 (12)C15B—O4B—C14B—O3B0.4 (3)
O4'—C14A—O4A—C15A110 (3)C15B—O4B—C14B—C13B179.78 (15)
C13A—C14A—O4A—C15A−178.7 (6)N1B—C13B—C14B—O3B−149.65 (17)
C16A—C15A—O4A—C14A−173.2 (15)N2B—C13B—C14B—O3B−20.7 (2)
O3'—C14A—O4'—C15'−14.9 (14)C17B—C13B—C14B—O3B92.7 (2)
O3A—C14A—O4'—C15'17.5 (12)N1B—C13B—C14B—O4B30.9 (2)
O4A—C14A—O4'—C15'−70 (2)N2B—C13B—C14B—O4B159.89 (14)
C13A—C14A—O4'—C15'172.9 (6)C17B—C13B—C14B—O4B−86.73 (18)
C16'—C15'—O4'—C14A97.1 (17)C14B—O4B—C15B—C16B78.0 (2)
C11A—N3A—C17A—N4A−89.73 (17)C11B—N3B—C17B—N4B−121.39 (15)
C21A—N3A—C17A—N4A57.41 (19)C21B—N3B—C17B—N4B56.85 (19)
C11A—N3A—C17A—C18A141.83 (15)C11B—N3B—C17B—C18B110.21 (16)
C21A—N3A—C17A—C18A−71.0 (2)C21B—N3B—C17B—C18B−71.54 (19)
C11A—N3A—C17A—C13A19.10 (17)C11B—N3B—C17B—C13B−11.69 (16)
C21A—N3A—C17A—C13A166.24 (14)C21B—N3B—C17B—C13B166.55 (13)
C12A—N4A—C17A—N3A121.29 (15)C12B—N4B—C17B—N3B90.12 (17)
C22A—N4A—C17A—N3A−62.3 (2)C22B—N4B—C17B—N3B−55.55 (19)
C12A—N4A—C17A—C18A−110.77 (17)C12B—N4B—C17B—C18B−140.11 (14)
C22A—N4A—C17A—C18A65.7 (2)C22B—N4B—C17B—C18B74.22 (18)
C12A—N4A—C17A—C13A11.01 (16)C12B—N4B—C17B—C13B−18.71 (16)
C22A—N4A—C17A—C13A−172.56 (14)C22B—N4B—C17B—C13B−164.38 (13)
N2A—C13A—C17A—N3A−135.92 (13)N1B—C13B—C17B—N3B19.17 (15)
N1A—C13A—C17A—N3A−17.62 (15)N2B—C13B—C17B—N3B−98.63 (13)
C14A—C13A—C17A—N3A98.73 (16)C14B—C13B—C17B—N3B142.81 (14)
N2A—C13A—C17A—N4A−17.70 (15)N1B—C13B—C17B—N4B137.80 (12)
N1A—C13A—C17A—N4A100.60 (13)N2B—C13B—C17B—N4B20.01 (14)
C14A—C13A—C17A—N4A−143.05 (15)C14B—C13B—C17B—N4B−98.55 (15)
N2A—C13A—C17A—C18A103.02 (16)N1B—C13B—C17B—C18B−102.72 (15)
N1A—C13A—C17A—C18A−138.68 (15)N2B—C13B—C17B—C18B139.49 (14)
C14A—C13A—C17A—C18A−22.3 (2)C14B—C13B—C17B—C18B20.9 (2)
N3A—C17A—C18A—O5'−0.4 (8)C19B—O6B—C18B—O5B−0.4 (3)
N4A—C17A—C18A—O5'−129.7 (8)C19B—O6B—C18B—C17B−178.18 (17)
C13A—C17A—C18A—O5'116.2 (8)N3B—C17B—C18B—O5B165.61 (18)
N3A—C17A—C18A—O5A−45.0 (8)N4B—C17B—C18B—O5B35.2 (2)
N4A—C17A—C18A—O5A−174.3 (7)C13B—C17B—C18B—O5B−79.6 (2)
C13A—C17A—C18A—O5A71.5 (7)N3B—C17B—C18B—O6B−16.5 (2)
N3A—C17A—C18A—O6'172.4 (5)N4B—C17B—C18B—O6B−146.88 (15)
N4A—C17A—C18A—O6'43.1 (5)C13B—C17B—C18B—O6B98.31 (17)
C13A—C17A—C18A—O6'−71.1 (5)C18B—O6B—C19B—C20B−171.94 (18)
N3A—C17A—C18A—O6A148.5 (6)C11B—N3B—C21B—C23B101.56 (18)
N4A—C17A—C18A—O6A19.2 (6)C17B—N3B—C21B—C23B−76.48 (19)
C13A—C17A—C18A—O6A−95.0 (6)C12B—N4B—C22B—C24B−66.68 (19)
O5'—C18A—O6A—C19A−33.7 (11)C17B—N4B—C22B—C24B76.02 (18)
O5A—C18A—O6A—C19A10.6 (12)N3B—C21B—C23B—C28B−118.73 (17)
O6'—C18A—O6A—C19A77 (2)N3B—C21B—C23B—C24B60.3 (2)
C17A—C18A—O6A—C19A176.6 (7)C28B—C23B—C24B—C25B−0.9 (2)
C20A—C19A—O6A—C18A−97 (2)C21B—C23B—C24B—C25B−179.94 (16)
O5'—C18A—O6'—C19'−9.7 (9)C28B—C23B—C24B—C22B177.98 (15)
O5A—C18A—O6'—C19'32.2 (8)C21B—C23B—C24B—C22B−1.0 (2)
O6A—C18A—O6'—C19'−93 (2)N4B—C22B—C24B—C25B118.61 (18)
C17A—C18A—O6'—C19'177.9 (5)N4B—C22B—C24B—C23B−60.3 (2)
C20'—C19'—O6'—C18A−178.2 (12)C23B—C24B—C25B—C26B0.3 (3)
C11A—N3A—C21A—C23A71.3 (2)C22B—C24B—C25B—C26B−178.62 (16)
C17A—N3A—C21A—C23A−72.7 (2)C24B—C25B—C26B—C27B0.7 (3)
C12A—N4A—C22A—C24A−107.15 (19)C24B—C25B—C26B—C30B179.62 (18)
C17A—N4A—C22A—C24A76.8 (2)C25B—C26B—C27B—C28B−1.1 (3)
N3A—C21A—C23A—C28A−122.71 (18)C30B—C26B—C27B—C28B−179.96 (18)
N3A—C21A—C23A—C24A59.4 (2)C25B—C26B—C27B—C29B177.13 (17)
C28A—C23A—C24A—C25A−2.4 (3)C30B—C26B—C27B—C29B−1.7 (3)
C21A—C23A—C24A—C25A175.58 (16)C26B—C27B—C28B—C23B0.5 (3)
C28A—C23A—C24A—C22A177.89 (16)C29B—C27B—C28B—C23B−177.79 (16)
C21A—C23A—C24A—C22A−4.2 (3)C24B—C23B—C28B—C27B0.6 (3)
N4A—C22A—C24A—C25A126.78 (18)C21B—C23B—C28B—C27B179.57 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9A—H9A1···O2Bi0.972.313.205 (2)153
C22B—H22A···O1Aii0.972.413.375 (2)178
C29B—H29A···O1Biii0.962.533.441 (3)160

Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2719).

References

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