organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aKey Laboratory of Pesticides and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: chlpcao@mails.ccnu.edu.cn

(Received 9 May 2010; accepted 9 June 2010; online 16 June 2010)

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[Wang, Z., Zhou, B., Chen, Y., Yin, G., Li, Y., Wu, A. & Isaacs, L. (2006). J. Org. Chem. 71, 4502-4508.]). For glycoluril and its derivatives, see: Freeman et al. (1981[Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc. 103, 7367-7368.]); Rebek (2005[Rebek, J. Jr (2005). Angew. Chem. Int. Ed. 44, 2068-2078.]); Rowan et al. (1999[Rowan, A. E., Elemans, J. A. A. W. & Nolte, R. J. M. (1999). Acc. Chem. Res. 32, 995-1006]); Wu et al. (2002[Wu, A., Fettinger, J. C. & Isaacs, L. (2002). Tetrahedron, 58, 9769-9777.]).

[Scheme 1]

Experimental

Crystal data
  • C30H34N4O6

  • Mr = 546.61

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9A—H9A1⋯O2Bi 0.97 2.31 3.205 (2) 153
C22B—H22A⋯O1Aii 0.97 2.41 3.375 (2) 178
C29B—H29A⋯O1Biii 0.96 2.53 3.441 (3) 160
Symmetry codes: (i) x, y+1, z; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of (I), showing one independent molecule with the atom-labelling scheme and 30% probability displacement ellipsoids.
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 top
Crystal data top
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 top
Bruker SMART 4K CCD area-detector
diffractometer
6896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
phi and ω scansh = 3131
67299 measured reflectionsk = 1515
13767 independent reflectionsl = 2828
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.86 w = 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
Crystal data top
C30H34N4O6V = 5540.1 (5) Å3
Mr = 546.61Z = 8
Monoclinic, P21/cMo Kα radiation
a = 23.4988 (12) ŵ = 0.09 mm1
b = 11.6005 (6) ÅT = 298 K
c = 21.2685 (11) Å0.16 × 0.12 × 0.10 mm
β = 107.145 (1)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
6896 reflections with I > 2σ(I)
67299 measured reflectionsRint = 0.052
13767 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04720 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 0.86Δρmax = 0.17 e Å3
13767 reflectionsΔρmin = 0.18 e Å3
809 parameters
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*/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)
C19A0.0582 (5)0.9725 (15)0.2662 (6)0.076 (3)0.414 (14)
H19D0.08410.91050.24400.091*0.414 (14)
H19C0.07821.04510.25140.091*0.414 (14)
C20A0.0465 (6)0.961 (2)0.3392 (5)0.125 (6)0.414 (14)
H20A0.02680.88920.35370.187*0.414 (14)
H20B0.08360.96310.34950.187*0.414 (14)
H20C0.02171.02360.36100.187*0.414 (14)
O5A0.0137 (4)1.1627 (7)0.2523 (6)0.083 (2)0.414 (14)
O6A0.0033 (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)
H19E0.07991.01840.24960.087*0.586 (14)
H19F0.04271.07900.31510.087*0.586 (14)
C20'0.0562 (4)0.9078 (7)0.3277 (5)0.084 (2)0.586 (14)
H20D0.06290.84030.30030.126*0.586 (14)
H20E0.09030.92130.34280.126*0.586 (14)
H20F0.02170.89640.36480.126*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)
H29D0.12981.07070.08380.160*
H29E0.10320.95690.12050.160*
H29F0.16800.95760.07210.160*
C30A0.09864 (10)0.7452 (2)0.05647 (11)0.0939 (8)
H30D0.07440.76020.10060.141*
H30F0.08620.67430.04130.141*
H30E0.13960.73910.05570.141*
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)
H1B10.60710.24000.64010.119*
H1B20.62150.16140.58680.119*
H1B30.60230.28990.57020.119*
C2B0.53769 (9)0.16490 (19)0.45324 (10)0.0748 (6)
H2B10.57530.12650.46990.112*
H2B20.51470.12740.41370.112*
H2B30.54420.24390.44380.112*
C3B0.53237 (8)0.18567 (15)0.57005 (10)0.0544 (5)
C4B0.49900 (8)0.17902 (14)0.61356 (9)0.0514 (4)
H4B0.51800.19310.65780.062*
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)
H7B0.42670.10910.44180.064*
C8B0.50443 (8)0.15993 (15)0.50415 (10)0.0535 (5)
C9B0.40622 (8)0.16434 (16)0.64638 (9)0.0536 (5)
H9B10.38280.23450.63720.064*
H9B20.43580.17430.68880.064*
C10B0.34481 (8)0.10271 (16)0.50137 (8)0.0548 (5)
H10A0.33720.07340.45690.066*
H10B0.32350.17510.49860.066*
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)
H15A0.19070.27610.62030.091*
H15B0.22820.31370.69120.091*
C16B0.24875 (11)0.4051 (2)0.61965 (12)0.0959 (8)
H16A0.24610.39300.57420.144*
H16B0.22300.46750.62320.144*
H16C0.28910.42370.64380.144*
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*
H19B0.20130.03600.74900.110*
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) top
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, º) top
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—C23A53.5 (2)
C1A—C3A—C4A—C5A179.06 (16)C23A—C24A—C25A—C26A1.5 (3)
C3A—C4A—C5A—C6A0.1 (2)C22A—C24A—C25A—C26A178.75 (16)
C3A—C4A—C5A—C9A178.31 (15)C24A—C25A—C26A—C27A0.4 (3)
C4A—C5A—C6A—C7A1.5 (2)C24A—C25A—C26A—C30A179.80 (17)
C9A—C5A—C6A—C7A179.68 (15)C25A—C26A—C27A—C28A1.4 (3)
C4A—C5A—C6A—C10A175.81 (15)C30A—C26A—C27A—C28A179.23 (18)
C9A—C5A—C6A—C10A2.3 (2)C25A—C26A—C27A—C29A176.23 (18)
C5A—C6A—C7A—C8A1.7 (2)C30A—C26A—C27A—C29A3.1 (3)
C10A—C6A—C7A—C8A175.76 (15)C24A—C23A—C28A—C27A1.4 (3)
C4A—C3A—C8A—C7A1.2 (2)C21A—C23A—C28A—C27A176.58 (17)
C1A—C3A—C8A—C7A179.18 (16)C26A—C27A—C28A—C23A0.5 (3)
C4A—C3A—C8A—C2A179.21 (16)C29A—C27A—C28A—C23A177.18 (19)
C1A—C3A—C8A—C2A0.5 (3)C8B—C3B—C4B—C5B2.6 (3)
C6A—C7A—C8A—C3A0.3 (3)C1B—C3B—C4B—C5B176.01 (17)
C6A—C7A—C8A—C2A179.36 (16)C3B—C4B—C5B—C6B2.7 (3)
C11A—N1A—C9A—C5A106.97 (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—C7B173.89 (16)
C6A—C5A—C9A—N1A54.9 (2)C4B—C5B—C6B—C10B176.46 (16)
C12A—N2A—C10A—C6A71.0 (2)C9B—C5B—C6B—C10B2.3 (3)
C13A—N2A—C10A—C6A72.5 (2)C5B—C6B—C7B—C8B2.3 (3)
C7A—C6A—C10A—N2A124.46 (17)C10B—C6B—C7B—C8B174.17 (16)
C5A—C6A—C10A—N2A58.2 (2)C6B—C7B—C8B—C3B2.4 (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—N3A0.24 (18)C1B—C3B—C8B—C7B178.54 (17)
C9A—N1A—C11A—N3A176.31 (14)C4B—C3B—C8B—C2B179.91 (16)
C17A—N3A—C11A—O1A168.77 (16)C1B—C3B—C8B—C2B1.5 (3)
C21A—N3A—C11A—O1A21.5 (3)C11B—N1B—C9B—C5B76.6 (2)
C17A—N3A—C11A—N1A12.71 (18)C13B—N1B—C9B—C5B70.0 (2)
C21A—N3A—C11A—N1A159.99 (14)C4B—C5B—C9B—N1B134.07 (16)
C17A—N4A—C12A—O2A179.59 (16)C6B—C5B—C9B—N1B51.8 (2)
C22A—N4A—C12A—O2A3.3 (3)C12B—N2B—C10B—C6B120.76 (17)
C17A—N4A—C12A—N2A0.43 (18)C13B—N2B—C10B—C6B72.4 (2)
C22A—N4A—C12A—N2A175.90 (14)C7B—C6B—C10B—N2B135.78 (16)
C13A—N2A—C12A—O2A167.42 (16)C5B—C6B—C10B—N2B48.0 (2)
C10A—N2A—C12A—O2A20.6 (2)C17B—N3B—C11B—O1B179.01 (15)
C13A—N2A—C12A—N4A13.43 (17)C21B—N3B—C11B—O1B2.8 (3)
C10A—N2A—C12A—N4A160.29 (13)C17B—N3B—C11B—N1B0.94 (17)
C12A—N2A—C13A—N1A89.10 (16)C21B—N3B—C11B—N1B179.15 (13)
C10A—N2A—C13A—N1A57.23 (19)C13B—N1B—C11B—O1B166.92 (15)
C12A—N2A—C13A—C14A144.62 (15)C9B—N1B—C11B—O1B17.4 (2)
C10A—N2A—C13A—C14A69.05 (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—O2B174.47 (16)
C11A—N1A—C13A—N2A121.71 (15)C10B—N2B—C12B—O2B6.5 (3)
C9A—N1A—C13A—N2A62.13 (19)C13B—N2B—C12B—N4B5.16 (18)
C11A—N1A—C13A—C14A108.92 (16)C10B—N2B—C12B—N4B173.16 (14)
C9A—N1A—C13A—C14A67.24 (19)C17B—N4B—C12B—O2B170.80 (16)
C11A—N1A—C13A—C17A11.40 (17)C22B—N4B—C12B—O2B24.8 (2)
C9A—N1A—C13A—C17A172.44 (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—N2B62.35 (19)
N2A—C13A—C14A—O3A147.2 (6)C11B—N1B—C13B—C14B145.31 (14)
N1A—C13A—C14A—O3A18.2 (6)C9B—N1B—C13B—C14B64.94 (19)
C17A—C13A—C14A—O3A93.6 (6)C11B—N1B—C13B—C17B21.49 (16)
N2A—C13A—C14A—O4A29.2 (7)C9B—N1B—C13B—C17B171.25 (13)
N1A—C13A—C14A—O4A158.3 (6)C12B—N2B—C13B—N1B125.86 (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—C14B63.17 (19)
C17A—C13A—C14A—O4'109.4 (6)C12B—N2B—C13B—C17B16.01 (17)
O3'—C14A—O4A—C15A23.4 (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—C15A178.7 (6)N1B—C13B—C14B—O3B149.65 (17)
C16A—C15A—O4A—C14A173.2 (15)N2B—C13B—C14B—O3B20.7 (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—O4B86.73 (18)
C16'—C15'—O4'—C14A97.1 (17)C14B—O4B—C15B—C16B78.0 (2)
C11A—N3A—C17A—N4A89.73 (17)C11B—N3B—C17B—N4B121.39 (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—C18A71.0 (2)C21B—N3B—C17B—C18B71.54 (19)
C11A—N3A—C17A—C13A19.10 (17)C11B—N3B—C17B—C13B11.69 (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—N3A62.3 (2)C22B—N4B—C17B—N3B55.55 (19)
C12A—N4A—C17A—C18A110.77 (17)C12B—N4B—C17B—C18B140.11 (14)
C22A—N4A—C17A—C18A65.7 (2)C22B—N4B—C17B—C18B74.22 (18)
C12A—N4A—C17A—C13A11.01 (16)C12B—N4B—C17B—C13B18.71 (16)
C22A—N4A—C17A—C13A172.56 (14)C22B—N4B—C17B—C13B164.38 (13)
N2A—C13A—C17A—N3A135.92 (13)N1B—C13B—C17B—N3B19.17 (15)
N1A—C13A—C17A—N3A17.62 (15)N2B—C13B—C17B—N3B98.63 (13)
C14A—C13A—C17A—N3A98.73 (16)C14B—C13B—C17B—N3B142.81 (14)
N2A—C13A—C17A—N4A17.70 (15)N1B—C13B—C17B—N4B137.80 (12)
N1A—C13A—C17A—N4A100.60 (13)N2B—C13B—C17B—N4B20.01 (14)
C14A—C13A—C17A—N4A143.05 (15)C14B—C13B—C17B—N4B98.55 (15)
N2A—C13A—C17A—C18A103.02 (16)N1B—C13B—C17B—C18B102.72 (15)
N1A—C13A—C17A—C18A138.68 (15)N2B—C13B—C17B—C18B139.49 (14)
C14A—C13A—C17A—C18A22.3 (2)C14B—C13B—C17B—C18B20.9 (2)
N3A—C17A—C18A—O5'0.4 (8)C19B—O6B—C18B—O5B0.4 (3)
N4A—C17A—C18A—O5'129.7 (8)C19B—O6B—C18B—C17B178.18 (17)
C13A—C17A—C18A—O5'116.2 (8)N3B—C17B—C18B—O5B165.61 (18)
N3A—C17A—C18A—O5A45.0 (8)N4B—C17B—C18B—O5B35.2 (2)
N4A—C17A—C18A—O5A174.3 (7)C13B—C17B—C18B—O5B79.6 (2)
C13A—C17A—C18A—O5A71.5 (7)N3B—C17B—C18B—O6B16.5 (2)
N3A—C17A—C18A—O6'172.4 (5)N4B—C17B—C18B—O6B146.88 (15)
N4A—C17A—C18A—O6'43.1 (5)C13B—C17B—C18B—O6B98.31 (17)
C13A—C17A—C18A—O6'71.1 (5)C18B—O6B—C19B—C20B171.94 (18)
N3A—C17A—C18A—O6A148.5 (6)C11B—N3B—C21B—C23B101.56 (18)
N4A—C17A—C18A—O6A19.2 (6)C17B—N3B—C21B—C23B76.48 (19)
C13A—C17A—C18A—O6A95.0 (6)C12B—N4B—C22B—C24B66.68 (19)
O5'—C18A—O6A—C19A33.7 (11)C17B—N4B—C22B—C24B76.02 (18)
O5A—C18A—O6A—C19A10.6 (12)N3B—C21B—C23B—C28B118.73 (17)
O6'—C18A—O6A—C19A77 (2)N3B—C21B—C23B—C24B60.3 (2)
C17A—C18A—O6A—C19A176.6 (7)C28B—C23B—C24B—C25B0.9 (2)
C20A—C19A—O6A—C18A97 (2)C21B—C23B—C24B—C25B179.94 (16)
O5'—C18A—O6'—C19'9.7 (9)C28B—C23B—C24B—C22B177.98 (15)
O5A—C18A—O6'—C19'32.2 (8)C21B—C23B—C24B—C22B1.0 (2)
O6A—C18A—O6'—C19'93 (2)N4B—C22B—C24B—C25B118.61 (18)
C17A—C18A—O6'—C19'177.9 (5)N4B—C22B—C24B—C23B60.3 (2)
C20'—C19'—O6'—C18A178.2 (12)C23B—C24B—C25B—C26B0.3 (3)
C11A—N3A—C21A—C23A71.3 (2)C22B—C24B—C25B—C26B178.62 (16)
C17A—N3A—C21A—C23A72.7 (2)C24B—C25B—C26B—C27B0.7 (3)
C12A—N4A—C22A—C24A107.15 (19)C24B—C25B—C26B—C30B179.62 (18)
C17A—N4A—C22A—C24A76.8 (2)C25B—C26B—C27B—C28B1.1 (3)
N3A—C21A—C23A—C28A122.71 (18)C30B—C26B—C27B—C28B179.96 (18)
N3A—C21A—C23A—C24A59.4 (2)C25B—C26B—C27B—C29B177.13 (17)
C28A—C23A—C24A—C25A2.4 (3)C30B—C26B—C27B—C29B1.7 (3)
C21A—C23A—C24A—C25A175.58 (16)C26B—C27B—C28B—C23B0.5 (3)
C28A—C23A—C24A—C22A177.89 (16)C29B—C27B—C28B—C23B177.79 (16)
C21A—C23A—C24A—C22A4.2 (3)C24B—C23B—C28B—C27B0.6 (3)
N4A—C22A—C24A—C25A126.78 (18)C21B—C23B—C28B—C27B179.57 (16)
Hydrogen-bond geometry (Å, º) top
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.

Experimental details

Crystal data
Chemical formulaC30H34N4O6
Mr546.61
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)23.4988 (12), 11.6005 (6), 21.2685 (11)
β (°) 107.145 (1)
V3)5540.1 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.16 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
67299, 13767, 6896
Rint0.052
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.116, 0.86
No. of reflections13767
No. of parameters809
No. of restraints20
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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.
 

Acknowledgements

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

References

First citationBruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.  Google Scholar
First citationFreeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc. 103, 7367–7368.  CSD CrossRef CAS Web of Science Google Scholar
First citationRebek, J. Jr (2005). Angew. Chem. Int. Ed. 44, 2068–2078.  Web of Science CrossRef CAS Google Scholar
First citationRowan, A. E., Elemans, J. A. A. W. & Nolte, R. J. M. (1999). Acc. Chem. Res. 32, 995–1006  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Z., Zhou, B., Chen, Y., Yin, G., Li, Y., Wu, A. & Isaacs, L. (2006). J. Org. Chem. 71, 4502–4508.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationWu, A., Fettinger, J. C. & Isaacs, L. (2002). Tetrahedron, 58, 9769–9777.  Web of Science CSD CrossRef CAS Google Scholar

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