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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1128.
Published online 2010 April 21. doi:  10.1107/S1600536810013929
PMCID: PMC2979120

2,5,11,14-Tetra­oxa-8-aza­dispiro­[13.4.0]nona­deca-15,17,19-triene

Abstract

The title compound, C14H21NO4, has been synthesized from o-dihydroxy­benzene by a three-step reaction. There are two chemically equal but crystallographically independent mol­ecules in the asymmetric unit. The crystal packing is governed by C—H(...)O hydrogen bonds and C—H(...)π inter­actions, forming an infinite network.

Related literature

For general background to crown ethers, see: Gokel et al. (2004 [triangle]); Wainwright (1997 [triangle]). For the synthesis, see: Lu & Wu (1989 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1128-scheme1.jpg

Experimental

Crystal data

  • C14H21NO4
  • M r = 267.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1128-efi1.jpg
  • a = 10.771 (7) Å
  • b = 8.662 (5) Å
  • c = 15.961 (10) Å
  • β = 105.417 (11)°
  • V = 1435.6 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 294 K
  • 0.20 × 0.16 × 0.14 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.951, T max = 0.987
  • 7411 measured reflections
  • 2717 independent reflections
  • 1848 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.175
  • S = 1.05
  • 2717 reflections
  • 343 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013929/fk2017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013929/fk2017Isup2.hkl

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

Acknowledgments

The project was supported by the Hebei Province Science and Technology Research and Development Program of China (project grant No. 07215133). The data collection was undertaken on a instrument managed by the Central Experimental Laboratory at the University of Nan Kai.

supplementary crystallographic information

Comment

Crown ethers can be subjected to diverse modifications to give a wide variety of derivatives, which could not only extend the original molecular binding ability, but also alter the molecular selectivity. Therefore, they are currently significant topics in supramolecular chemistry (Gokel et al., 2004). Among the large number of compounds, aza-crown ethers are the important component (Wainwright,1997). Although the synthesis of the title compound has been reported previously (Lu & Wu, 1989), the crystal structure had not been determined. The compound is an important precursor in the synthesis of aza-crown ethers.

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). There are two chemically equal but crystallographically independent molecules per asymmetric unit.

As shown in Fig. 2, molecules are linked by C—H···π and C—H···O hydrogen bonds to compose the crystal packing. The molecules (that contains N2) form 1D supramolecular chain by the C26—H26A···π interactions involving the C15—C20 benzene ring (centroid Cg1 ).In addition, through C(21)—H(21B)···O(3) hydrogen bond, the 1D supramolecular chain is connected with the molecules (that contains N1) to form an infinite network (Table 1) .

Experimental

The title compound was prepared according the previous literature. The product was isolated, recrystallized from ethyl acetate, and then dried in vacuum to give the pure title compound in 63% yield. The single crystals suitable for X-ray analysis were obtained as colourless blocks by slow evaporation of an ethyl acetate solution.

Refinement

Due to insignificant anomalous dispersion effects, Friedel pairs were merged before refinement.

The H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H and N—H bond lengths and isotropic U parameters: 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2—H; 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene C—H; 0.89 Å and Uiso(H) = 1.2Ueq(N) for imino N—H.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Packing diagram for (I), with H bonds drawn as dashed lines.

Crystal data

C14H21NO4F(000) = 576
Mr = 267.32Dx = 1.237 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 936 reflections
a = 10.771 (7) Åθ = 2.6–22.4°
b = 8.662 (5) ŵ = 0.09 mm1
c = 15.961 (10) ÅT = 294 K
β = 105.417 (11)°Block, colourless
V = 1435.6 (15) Å30.20 × 0.16 × 0.14 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer2717 independent reflections
Radiation source: fine-focus sealed tube1848 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −12→9
Tmin = 0.951, Tmax = 0.987k = −9→10
7411 measured reflectionsl = −18→18

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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.1029P)2 + 0.0778P] where P = (Fo2 + 2Fc2)/3
2717 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.43 e Å3
1 restraintΔρmin = −0.19 e Å3

Special details

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 > 2σ(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*/Ueq
N10.3503 (4)0.5129 (6)0.1371 (3)0.0573 (12)
H10.43590.51870.15350.069*
N20.7083 (4)0.0166 (6)0.5069 (3)0.0595 (13)
H2A0.75190.01170.46680.071*
O10.7230 (3)0.4836 (4)0.2096 (2)0.0488 (9)
O20.6683 (4)0.6169 (4)0.0602 (2)0.0579 (10)
O30.4078 (4)0.5783 (5)−0.0279 (2)0.0585 (11)
O40.5273 (4)0.3439 (5)0.2723 (3)0.0604 (11)
O50.9938 (3)0.1199 (4)0.3925 (2)0.0545 (10)
O60.8056 (3)−0.0162 (4)0.2862 (2)0.0479 (9)
O70.6115 (4)−0.1540 (5)0.3498 (3)0.0637 (11)
O80.9812 (4)0.0834 (5)0.5652 (3)0.0596 (11)
C10.8137 (5)0.4670 (6)0.1632 (3)0.0488 (13)
C20.9266 (5)0.3848 (7)0.1912 (4)0.0650 (18)
H20.94670.33810.24570.078*
C31.0097 (6)0.3708 (11)0.1397 (6)0.091 (3)
H31.08500.31360.15860.109*
C40.9809 (6)0.4413 (12)0.0610 (6)0.091 (3)
H41.03760.43150.02650.109*
C50.8682 (6)0.5286 (8)0.0300 (4)0.0700 (18)
H50.85130.5778−0.02360.084*
C60.7824 (5)0.5399 (6)0.0812 (3)0.0480 (13)
C70.6160 (6)0.6595 (8)−0.0305 (4)0.0656 (17)
H7A0.61730.5720−0.06810.079*
H7B0.66560.7429−0.04620.079*
C80.4788 (6)0.7108 (7)−0.0382 (4)0.0621 (17)
H8A0.47700.78640.00630.075*
H8B0.44200.7573−0.09470.075*
C90.2861 (5)0.6140 (8)−0.0110 (4)0.0655 (17)
H9A0.22770.5281−0.02990.079*
H9B0.24920.7037−0.04500.079*
C100.2971 (6)0.6457 (8)0.0824 (4)0.0623 (16)
H10A0.35230.73460.10090.075*
H10B0.21270.67010.08960.075*
C110.3550 (6)0.5332 (8)0.2280 (4)0.0634 (16)
H11A0.26950.55750.23330.076*
H11B0.41130.61900.25160.076*
C120.4036 (6)0.3892 (8)0.2795 (4)0.0719 (18)
H12A0.40800.40730.34010.086*
H12B0.34310.30580.25900.086*
C130.6295 (6)0.4306 (8)0.3246 (4)0.0628 (16)
H13A0.64680.39780.38480.075*
H13B0.60740.53940.32140.075*
C140.7460 (6)0.4043 (7)0.2915 (4)0.0636 (17)
H14A0.82250.44490.33230.076*
H14B0.75830.29490.28380.076*
C151.0249 (5)0.0476 (6)0.3258 (3)0.0465 (13)
C161.1469 (6)0.0433 (9)0.3128 (5)0.0717 (18)
H161.21550.09180.35170.086*
C171.1656 (7)−0.0350 (12)0.2405 (5)0.093 (3)
H171.2469−0.03650.23060.111*
C181.0679 (9)−0.1073 (10)0.1856 (5)0.092 (3)
H181.0827−0.15930.13830.111*
C190.9450 (6)−0.1071 (8)0.1971 (4)0.0664 (18)
H190.8787−0.16000.15860.080*
C200.9218 (5)−0.0267 (6)0.2672 (3)0.0490 (13)
C210.6986 (6)−0.0989 (7)0.2322 (4)0.0611 (17)
H21A0.7184−0.20810.23160.073*
H21B0.6784−0.06040.17300.073*
C220.5881 (5)−0.0732 (8)0.2704 (4)0.0624 (16)
H22A0.57870.03620.28030.075*
H22B0.5090−0.10990.23070.075*
C230.5317 (6)−0.1077 (9)0.4040 (5)0.0733 (19)
H23A0.5265−0.19180.44300.088*
H23B0.4454−0.08810.36770.088*
C240.5793 (5)0.0330 (9)0.4564 (4)0.0691 (18)
H24A0.57350.12070.41780.083*
H24B0.52470.05370.49460.083*
C250.7610 (6)0.1461 (8)0.5623 (4)0.0652 (17)
H25A0.70630.16740.60040.078*
H25B0.76040.23660.52650.078*
C260.8935 (6)0.1184 (9)0.6157 (4)0.0680 (17)
H26A0.92380.20940.65050.082*
H26B0.89280.03330.65510.082*
C271.0351 (6)0.2157 (7)0.5353 (4)0.0598 (16)
H27A1.09860.26300.58310.072*
H27B0.96810.29090.51200.072*
C281.0969 (5)0.1666 (8)0.4664 (4)0.0623 (16)
H28A1.14510.25150.45070.075*
H28B1.15540.08120.48670.075*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.058 (3)0.052 (3)0.059 (3)0.006 (2)0.011 (2)−0.004 (2)
N20.057 (3)0.057 (3)0.061 (3)−0.001 (2)0.010 (2)−0.009 (3)
O10.055 (2)0.043 (2)0.043 (2)0.0067 (17)0.0039 (16)0.0097 (17)
O20.072 (2)0.055 (2)0.045 (2)0.010 (2)0.0130 (18)0.0087 (19)
O30.074 (2)0.045 (2)0.052 (2)0.000 (2)0.0089 (19)−0.0005 (18)
O40.065 (2)0.049 (2)0.064 (3)−0.002 (2)0.012 (2)0.004 (2)
O50.050 (2)0.054 (2)0.055 (2)−0.0023 (18)0.0058 (17)−0.011 (2)
O60.0511 (19)0.043 (2)0.045 (2)−0.0020 (17)0.0036 (16)−0.0105 (17)
O70.071 (2)0.057 (2)0.059 (3)−0.011 (2)0.010 (2)−0.004 (2)
O80.068 (2)0.053 (2)0.055 (2)−0.003 (2)0.0108 (19)−0.0064 (19)
C10.049 (3)0.041 (3)0.052 (3)−0.006 (2)0.005 (2)−0.011 (3)
C20.041 (3)0.063 (4)0.080 (5)0.004 (3)−0.004 (3)0.000 (3)
C30.048 (4)0.105 (6)0.109 (7)0.000 (4)0.003 (4)−0.029 (5)
C40.050 (4)0.122 (7)0.105 (6)−0.017 (4)0.029 (4)−0.043 (6)
C50.081 (4)0.067 (4)0.069 (4)−0.010 (4)0.032 (3)−0.010 (4)
C60.051 (3)0.038 (3)0.053 (3)−0.010 (3)0.011 (3)−0.006 (3)
C70.080 (4)0.058 (4)0.055 (3)−0.016 (3)0.011 (3)0.013 (3)
C80.072 (4)0.047 (3)0.058 (4)0.001 (3)0.001 (3)0.016 (3)
C90.063 (4)0.061 (4)0.064 (4)0.014 (3)0.004 (3)0.003 (3)
C100.065 (3)0.054 (4)0.064 (4)0.011 (3)0.008 (3)−0.009 (3)
C110.061 (3)0.070 (4)0.062 (4)0.002 (3)0.020 (3)−0.011 (3)
C120.083 (4)0.074 (5)0.064 (4)−0.019 (4)0.029 (3)−0.004 (4)
C130.080 (4)0.060 (4)0.043 (3)−0.005 (3)0.006 (3)0.008 (3)
C140.078 (4)0.046 (3)0.050 (3)−0.010 (3)−0.014 (3)0.011 (3)
C150.050 (3)0.043 (3)0.048 (3)0.007 (2)0.015 (2)0.008 (3)
C160.057 (3)0.079 (5)0.084 (5)0.008 (3)0.026 (3)0.011 (4)
C170.069 (4)0.140 (8)0.076 (5)0.039 (5)0.031 (4)0.041 (5)
C180.119 (6)0.105 (7)0.067 (5)0.056 (6)0.050 (5)0.020 (5)
C190.084 (4)0.065 (4)0.050 (4)0.019 (4)0.018 (3)−0.003 (3)
C200.064 (3)0.041 (3)0.040 (3)0.015 (3)0.010 (2)0.007 (2)
C210.082 (4)0.044 (3)0.042 (3)−0.016 (3)−0.010 (3)−0.003 (3)
C220.047 (3)0.064 (4)0.064 (4)−0.011 (3)−0.007 (3)−0.007 (3)
C230.054 (3)0.081 (5)0.086 (5)−0.014 (3)0.021 (3)0.007 (4)
C240.058 (4)0.081 (5)0.068 (4)0.016 (3)0.017 (3)−0.006 (4)
C250.075 (4)0.065 (4)0.058 (4)0.012 (3)0.021 (3)−0.006 (3)
C260.081 (4)0.073 (4)0.050 (3)−0.002 (4)0.017 (3)−0.010 (3)
C270.069 (4)0.048 (4)0.056 (4)−0.015 (3)0.005 (3)−0.019 (3)
C280.046 (3)0.062 (4)0.071 (4)−0.020 (3)0.000 (3)−0.010 (3)

Geometric parameters (Å, °)

N1—C111.450 (7)C10—H10B0.9700
N1—C101.465 (8)C11—C121.508 (10)
N1—H10.8900C11—H11A0.9700
N2—C241.416 (7)C11—H11B0.9700
N2—C251.448 (8)C12—H12A0.9700
N2—H2A0.8900C12—H12B0.9700
O1—C11.382 (6)C13—C141.503 (9)
O1—C141.439 (7)C13—H13A0.9700
O2—C61.360 (6)C13—H13B0.9700
O2—C71.454 (7)C14—H14A0.9700
O3—C81.413 (7)C14—H14B0.9700
O3—C91.440 (7)C15—C161.384 (8)
O4—C131.409 (7)C15—C201.403 (7)
O4—C121.422 (8)C16—C171.398 (11)
O5—C151.352 (6)C16—H160.9300
O5—C281.446 (6)C17—C181.333 (11)
O6—C201.367 (6)C17—H170.9300
O6—C211.434 (6)C18—C191.383 (10)
O7—C221.410 (7)C18—H180.9300
O7—C231.429 (8)C19—C201.395 (8)
O8—C271.423 (8)C19—H190.9300
O8—C261.428 (7)C21—C221.492 (9)
C1—C21.377 (8)C21—H21A0.9700
C1—C61.412 (8)C21—H21B0.9700
C2—C31.372 (10)C22—H22A0.9700
C2—H20.9300C22—H22B0.9700
C3—C41.357 (11)C23—C241.490 (10)
C3—H30.9300C23—H23A0.9700
C4—C51.403 (10)C23—H23B0.9700
C4—H40.9300C24—H24A0.9700
C5—C61.390 (8)C24—H24B0.9700
C5—H50.9300C25—C261.474 (8)
C7—C81.516 (9)C25—H25A0.9700
C7—H7A0.9700C25—H25B0.9700
C7—H7B0.9700C26—H26A0.9700
C8—H8A0.9700C26—H26B0.9700
C8—H8B0.9700C27—C281.490 (8)
C9—C101.489 (9)C27—H27A0.9700
C9—H9A0.9700C27—H27B0.9700
C9—H9B0.9700C28—H28A0.9700
C10—H10A0.9700C28—H28B0.9700
C11—N1—C10113.9 (5)H13A—C13—H13B108.5
C11—N1—H186.5O1—C14—C13106.8 (4)
C10—N1—H1110.0O1—C14—H14A110.4
C24—N2—C25115.8 (5)C13—C14—H14A110.4
C24—N2—H2A102.8O1—C14—H14B110.4
C25—N2—H2A106.3C13—C14—H14B110.4
C1—O1—C14117.5 (4)H14A—C14—H14B108.6
C6—O2—C7117.0 (4)O5—C15—C16125.0 (5)
C8—O3—C9113.3 (5)O5—C15—C20114.8 (4)
C13—O4—C12114.0 (5)C16—C15—C20120.1 (6)
C15—O5—C28118.4 (4)C15—C16—C17119.2 (7)
C20—O6—C21118.0 (4)C15—C16—H16120.4
C22—O7—C23114.3 (5)C17—C16—H16120.4
C27—O8—C26114.1 (5)C18—C17—C16120.5 (6)
C2—C1—O1124.7 (5)C18—C17—H17119.7
C2—C1—C6120.3 (5)C16—C17—H17119.7
O1—C1—C6115.0 (4)C17—C18—C19121.9 (7)
C3—C2—C1120.7 (7)C17—C18—H18119.0
C3—C2—H2119.6C19—C18—H18119.0
C1—C2—H2119.6C18—C19—C20119.2 (7)
C4—C3—C2119.3 (7)C18—C19—H19120.4
C4—C3—H3120.3C20—C19—H19120.4
C2—C3—H3120.3O6—C20—C19125.5 (5)
C3—C4—C5122.2 (7)O6—C20—C15115.5 (4)
C3—C4—H4118.9C19—C20—C15119.0 (5)
C5—C4—H4118.9O6—C21—C22106.3 (5)
C6—C5—C4118.6 (7)O6—C21—H21A110.5
C6—C5—H5120.7C22—C21—H21A110.5
C4—C5—H5120.7O6—C21—H21B110.5
O2—C6—C5126.1 (5)C22—C21—H21B110.5
O2—C6—C1115.1 (4)H21A—C21—H21B108.7
C5—C6—C1118.8 (5)O7—C22—C21108.8 (5)
O2—C7—C8105.5 (5)O7—C22—H22A109.9
O2—C7—H7A110.6C21—C22—H22A109.9
C8—C7—H7A110.6O7—C22—H22B109.9
O2—C7—H7B110.6C21—C22—H22B109.9
C8—C7—H7B110.6H22A—C22—H22B108.3
H7A—C7—H7B108.8O7—C23—C24113.4 (5)
O3—C8—C7107.3 (5)O7—C23—H23A108.9
O3—C8—H8A110.2C24—C23—H23A108.9
C7—C8—H8A110.2O7—C23—H23B108.9
O3—C8—H8B110.2C24—C23—H23B108.9
C7—C8—H8B110.2H23A—C23—H23B107.7
H8A—C8—H8B108.5N2—C24—C23112.1 (5)
O3—C9—C10113.1 (5)N2—C24—H24A109.2
O3—C9—H9A109.0C23—C24—H24A109.2
C10—C9—H9A109.0N2—C24—H24B109.2
O3—C9—H9B109.0C23—C24—H24B109.2
C10—C9—H9B109.0H24A—C24—H24B107.9
H9A—C9—H9B107.8N2—C25—C26112.9 (5)
N1—C10—C9111.5 (5)N2—C25—H25A109.0
N1—C10—H10A109.3C26—C25—H25A109.0
C9—C10—H10A109.3N2—C25—H25B109.0
N1—C10—H10B109.3C26—C25—H25B109.0
C9—C10—H10B109.3H25A—C25—H25B107.8
H10A—C10—H10B108.0O8—C26—C25113.1 (5)
N1—C11—C12111.1 (5)O8—C26—H26A109.0
N1—C11—H11A109.4C25—C26—H26A109.0
C12—C11—H11A109.4O8—C26—H26B109.0
N1—C11—H11B109.4C25—C26—H26B109.0
C12—C11—H11B109.4H26A—C26—H26B107.8
H11A—C11—H11B108.0O8—C27—C28108.7 (5)
O4—C12—C11112.4 (5)O8—C27—H27A110.0
O4—C12—H12A109.1C28—C27—H27A110.0
C11—C12—H12A109.1O8—C27—H27B110.0
O4—C12—H12B109.1C28—C27—H27B110.0
C11—C12—H12B109.1H27A—C27—H27B108.3
H12A—C12—H12B107.8O5—C28—C27106.5 (4)
O4—C13—C14107.7 (5)O5—C28—H28A110.4
O4—C13—H13A110.2C27—C28—H28A110.4
C14—C13—H13A110.2O5—C28—H28B110.4
O4—C13—H13B110.2C27—C28—H28B110.4
C14—C13—H13B110.2H28A—C28—H28B108.6
C14—O1—C1—C2−2.5 (7)C28—O5—C15—C16−14.8 (8)
C14—O1—C1—C6176.5 (4)C28—O5—C15—C20165.2 (5)
O1—C1—C2—C3178.2 (6)O5—C15—C16—C17−179.5 (6)
C6—C1—C2—C3−0.7 (9)C20—C15—C16—C170.4 (9)
C1—C2—C3—C41.1 (11)C15—C16—C17—C18−1.4 (11)
C2—C3—C4—C5−0.1 (12)C16—C17—C18—C190.6 (13)
C3—C4—C5—C6−1.4 (11)C17—C18—C19—C201.2 (11)
C7—O2—C6—C515.7 (8)C21—O6—C20—C192.5 (8)
C7—O2—C6—C1−164.7 (5)C21—O6—C20—C15−175.7 (4)
C4—C5—C6—O2−178.6 (6)C18—C19—C20—O6179.8 (6)
C4—C5—C6—C11.8 (8)C18—C19—C20—C15−2.1 (9)
C2—C1—C6—O2179.6 (5)O5—C15—C20—O6−0.4 (6)
O1—C1—C6—O20.6 (6)C16—C15—C20—O6179.6 (5)
C2—C1—C6—C5−0.8 (7)O5—C15—C20—C19−178.7 (5)
O1—C1—C6—C5−179.8 (5)C16—C15—C20—C191.3 (8)
C6—O2—C7—C8168.2 (5)C20—O6—C21—C22177.2 (5)
C9—O3—C8—C7164.6 (4)C23—O7—C22—C21164.3 (5)
O2—C7—C8—O3−69.4 (6)O6—C21—C22—O7−70.3 (6)
C8—O3—C9—C10−83.9 (7)C22—O7—C23—C24−82.3 (6)
C11—N1—C10—C9−176.0 (5)C25—N2—C24—C23−177.9 (5)
O3—C9—C10—N1−59.7 (7)O7—C23—C24—N2−54.7 (8)
C10—N1—C11—C12176.8 (5)C24—N2—C25—C26177.5 (5)
C13—O4—C12—C1178.4 (6)C27—O8—C26—C2585.5 (7)
N1—C11—C12—O457.2 (7)N2—C25—C26—O857.8 (8)
C12—O4—C13—C14−163.3 (5)C26—O8—C27—C28−165.8 (4)
C1—O1—C14—C13−175.5 (5)C15—O5—C28—C27−169.9 (5)
O4—C13—C14—O171.4 (6)O8—C27—C28—O568.3 (6)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 ring.
D—H···AD—HH···AD···AD—H···A
C21—H21B···O3i0.972.563.511 (2)168
C26—H26A···Cg10.972.693.646 (2)168

Symmetry codes: (i) −x+1, y−1/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2017).

References

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