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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1623.
Published online 2008 July 31. doi:  10.1107/S1600536808023192
PMCID: PMC2962232

3-Methyl-2,6-dinitro-N-(3-pent­yl)-4-[(2,3,4-tri-O-acetyl-β-d-xylos­yl)amino­methyl]­aniline

Abstract

In the title compound, C24H34N4O11, the hexopyranosyl ring adopts a chair conformation. The four substituents are in equatorial positions. The mol­ecule shows an intra­molecular N—H(...)O hydrogen bond.

Related literature

For related literature, see: Grichar & Dotray (2007 [triangle]); Kubátová et al. (2006 [triangle]); Wang et al. (2008 [triangle]); Yang et al. (2004 [triangle]).

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Object name is e-64-o1623-scheme1.jpg

Experimental

Crystal data

  • C24H34N4O11
  • M r = 554.55
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1623-efi1.jpg
  • a = 7.4100 (15) Å
  • b = 11.044 (2) Å
  • c = 34.106 (7) Å
  • V = 2791.1 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 [triangle]) T min = 0.969, T max = 0.990
  • 2870 measured reflections
  • 2870 independent reflections
  • 1662 reflections with I > 2σ(I)
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.196
  • S = 1.04
  • 2870 reflections
  • 352 parameters
  • 13 restraints
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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 global, I. DOI: 10.1107/S1600536808023192/er2053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023192/er2053Isup2.hkl

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

supplementary crystallographic information

Comment

Pendimethaline(3,4-dimethyl-2,6-dinitro-N-(pentan-3-yl)benzenamine) plays an important role in controlling weeds (Grichar & Dotray, 2007). However, problems such as toxic residues and environmental pollution were protruded increasingly by using amounts of herbicides during the past decades (Kubátová et al., 2006). In the search for a new herbicide with high efficiency and low toxicity, we obtained the title compound. All bond lengths and angles in the title molecule show normal values. The hexopyranosyl ring adopts a chair conformation (Fig. 1). The three acetyl groups are individually planar and occupy equatorial positions (Yang et al., 2004; Wang et al.,2008). The torsion angle C14—N4—C13—C9 is 95.8°.

Experimental

The title compound was prepared from β-D-1-amine-2,3,4-tri-O-acetyl-xylosyl with 4-(bromomethyl)-3-methyl-2,6-dinitro-N-(pentan-3-yl)benzenamine in dimethylformamide (DMF) in the presence of sodium carbonate. Fine yellow block crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of an acetonitrile and ethyl acetate (1:10) solution at room temperature.

Refinement

In the absence of significant anomalous scattering effects Friedel pairs have been merged.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C24H34N4O11F000 = 1176
Mr = 554.55Dx = 1.320 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.4100 (15) Åθ = 10–13º
b = 11.044 (2) ŵ = 0.11 mm1
c = 34.106 (7) ÅT = 293 (2) K
V = 2791.1 (10) Å3Block, yellow
Z = 40.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.0000
Radiation source: fine-focus sealed tubeθmax = 25.1º
Monochromator: graphiteθmin = 1.2º
T = 293(2) Kh = 0→8
ω/2θ scansk = 0→13
Absorption correction: ψ scan(XCAD4; Harms & Wocadlo, 1995)l = 0→40
Tmin = 0.969, Tmax = 0.9903 standard reflections
2870 measured reflections every 200 reflections
2870 independent reflections intensity decay: none
1662 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.196  w = 1/[σ2(Fo2) + (0.1035P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2870 reflectionsΔρmax = 0.18 e Å3
352 parametersΔρmin = −0.23 e Å3
13 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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*/Ueq
N10.8178 (10)0.2626 (5)0.1700 (2)0.095 (2)
H1A0.90240.22340.15830.114*
C10.8949 (13)0.0842 (12)0.2352 (3)0.142 (5)
H1B0.94370.00660.24220.213*
H1C0.82940.11690.25710.213*
H1D0.99160.13810.22840.213*
O10.6282 (15)0.4037 (7)0.2480 (2)0.166 (5)
C20.7702 (12)0.0702 (7)0.2009 (2)0.080 (2)
H2A0.67720.01230.20790.096*
H2B0.83820.03620.17920.096*
N20.5848 (15)0.4284 (7)0.2134 (4)0.124 (4)
O20.4388 (11)0.4255 (7)0.1997 (4)0.178 (5)
N31.1129 (8)0.3679 (5)0.12461 (15)0.0628 (15)
O31.2320 (8)0.4167 (5)0.10820 (17)0.0993 (19)
C30.3754 (17)0.0983 (10)0.1705 (3)0.139 (4)
H3A0.29380.08090.14940.209*
H3B0.31690.15010.18920.209*
H3C0.41020.02410.18310.209*
N41.1134 (7)0.8095 (4)0.14687 (15)0.0598 (14)
H4A1.22150.80420.15590.072*
O41.0911 (9)0.2574 (4)0.12117 (18)0.104 (2)
C40.5383 (12)0.1598 (8)0.1548 (3)0.100 (3)
H4B0.50280.23580.14280.120*
H4C0.59210.10950.13470.120*
O51.0104 (14)1.2551 (5)0.0281 (2)0.138 (3)
C50.6794 (10)0.1850 (6)0.1869 (2)0.0673 (19)
H5A0.62210.22620.20900.081*
O61.0543 (7)1.0657 (3)0.00833 (11)0.0597 (11)
C60.8401 (10)0.3854 (5)0.1690 (2)0.0645 (19)
C70.7377 (10)0.4713 (6)0.1903 (2)0.071 (2)
O71.3806 (6)0.9512 (4)0.02752 (12)0.0577 (11)
C80.7674 (9)0.5952 (5)0.18989 (18)0.0544 (16)
O81.3595 (8)0.8031 (5)−0.01708 (16)0.0878 (16)
O91.3373 (6)0.7535 (3)0.08050 (13)0.0579 (11)
C90.9162 (9)0.6406 (5)0.16961 (17)0.0497 (15)
O101.5721 (9)0.8095 (5)0.1159 (2)0.128 (3)
C101.0208 (9)0.5642 (5)0.14899 (18)0.0547 (16)
H10A1.11790.59540.13490.066*
O110.9818 (6)0.9650 (4)0.10992 (12)0.0625 (12)
C110.9889 (8)0.4396 (5)0.14790 (19)0.0576 (16)
C120.6414 (11)0.6798 (6)0.2129 (2)0.082 (2)
H12A0.54860.63290.22530.124*
H12B0.58730.73690.19520.124*
H12C0.70950.72240.23240.124*
C130.9561 (11)0.7768 (5)0.1707 (2)0.070 (2)
H13A0.85150.82070.16120.084*
H13B0.97730.80130.19760.084*
C141.0783 (9)0.8495 (5)0.1089 (2)0.0573 (17)
H14A1.00310.78930.09550.069*
C150.9289 (9)1.0028 (6)0.07198 (19)0.0647 (18)
H15A0.85251.07380.07390.078*
H15B0.86060.93900.05930.078*
C161.0952 (9)1.0320 (5)0.04803 (17)0.0544 (16)
H16A1.16381.09680.06080.065*
C171.2120 (8)0.9170 (5)0.04514 (17)0.0498 (15)
H17A1.15120.85560.02920.060*
C181.2506 (9)0.8685 (5)0.08543 (19)0.0559 (16)
H18A1.33100.92400.09950.067*
C191.0118 (14)1.2105 (7)−0.0406 (3)0.105 (3)
H19A0.99221.2957−0.04420.157*
H19B0.91131.1662−0.05110.157*
H19C1.12021.1867−0.05390.157*
C201.0292 (12)1.1850 (6)0.0003 (3)0.080 (2)
C211.6071 (11)0.9433 (6)−0.0209 (2)0.077 (2)
H21A1.64190.8986−0.04380.115*
H21B1.70180.9391−0.00170.115*
H21C1.58601.0263−0.02780.115*
C221.4367 (10)0.8896 (6)−0.00402 (19)0.0584 (17)
C231.5679 (9)0.6105 (6)0.0884 (2)0.079 (2)
H23A1.68640.60080.09930.118*
H23B1.57320.60020.06050.118*
H23C1.48830.55100.09950.118*
C241.4995 (9)0.7333 (7)0.0977 (2)0.070 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.101 (5)0.037 (3)0.148 (5)−0.011 (3)0.056 (4)−0.014 (3)
C10.098 (7)0.224 (14)0.104 (6)0.023 (9)−0.032 (6)−0.029 (8)
O10.280 (13)0.079 (4)0.140 (5)−0.068 (6)0.113 (8)−0.038 (4)
C20.100 (6)0.062 (5)0.079 (5)0.001 (5)0.003 (4)0.005 (4)
N20.115 (8)0.045 (4)0.212 (10)−0.009 (5)0.088 (8)−0.011 (6)
O20.076 (5)0.080 (5)0.379 (16)−0.002 (4)0.097 (8)−0.002 (7)
N30.067 (4)0.048 (3)0.073 (3)0.004 (3)0.026 (3)0.007 (3)
O30.088 (4)0.063 (3)0.147 (5)−0.010 (3)0.068 (4)−0.007 (3)
C30.141 (9)0.128 (9)0.148 (9)−0.052 (9)−0.028 (8)−0.006 (7)
N40.058 (3)0.050 (3)0.071 (3)−0.014 (3)−0.001 (3)0.010 (3)
O40.123 (5)0.045 (3)0.145 (5)−0.001 (3)0.073 (4)−0.011 (3)
C40.104 (7)0.072 (5)0.124 (7)−0.013 (6)−0.006 (6)0.009 (5)
O50.245 (10)0.046 (3)0.122 (5)0.025 (5)−0.041 (6)0.004 (3)
C50.077 (5)0.039 (3)0.086 (4)−0.008 (3)0.026 (4)−0.004 (3)
O60.078 (3)0.039 (2)0.062 (2)−0.002 (2)0.000 (2)0.0058 (19)
C60.073 (5)0.032 (3)0.088 (5)−0.011 (3)0.032 (4)−0.010 (3)
C70.056 (4)0.039 (4)0.119 (6)−0.012 (3)0.025 (4)0.002 (4)
O70.061 (3)0.039 (2)0.072 (3)−0.003 (2)0.001 (2)−0.004 (2)
C80.058 (4)0.035 (3)0.070 (4)−0.006 (3)0.018 (4)0.000 (3)
O80.096 (4)0.066 (3)0.101 (4)−0.001 (3)0.007 (3)−0.026 (3)
O90.050 (2)0.037 (2)0.087 (3)0.000 (2)−0.007 (2)−0.007 (2)
C90.057 (4)0.028 (3)0.064 (4)−0.005 (3)0.000 (3)0.006 (3)
O100.097 (5)0.076 (4)0.210 (7)−0.011 (4)−0.072 (5)−0.023 (5)
C100.048 (4)0.039 (3)0.077 (4)−0.006 (3)0.003 (3)0.006 (3)
O110.070 (3)0.045 (2)0.073 (3)0.009 (2)0.006 (2)0.003 (2)
C110.052 (4)0.037 (3)0.084 (4)0.002 (3)0.020 (3)−0.001 (3)
C120.084 (5)0.045 (4)0.118 (6)0.007 (4)0.058 (5)−0.007 (4)
C130.092 (5)0.033 (3)0.085 (5)−0.009 (4)0.027 (4)0.006 (3)
C140.059 (4)0.034 (3)0.078 (4)−0.002 (3)0.008 (4)−0.002 (3)
C150.065 (4)0.051 (4)0.078 (4)0.004 (4)0.016 (4)0.003 (3)
C160.063 (4)0.033 (3)0.068 (4)0.000 (3)0.000 (3)−0.002 (3)
C170.044 (3)0.034 (3)0.071 (4)−0.007 (3)−0.008 (3)0.009 (3)
C180.051 (4)0.028 (3)0.089 (4)0.000 (3)−0.001 (4)0.001 (3)
C190.122 (7)0.058 (5)0.135 (7)−0.013 (5)−0.033 (7)0.030 (5)
C200.104 (7)0.038 (4)0.100 (6)−0.006 (4)−0.024 (5)0.016 (4)
C210.084 (5)0.063 (4)0.082 (5)−0.002 (4)0.019 (4)−0.005 (4)
C220.059 (4)0.044 (4)0.072 (4)0.003 (3)−0.001 (4)−0.004 (3)
C230.046 (4)0.069 (5)0.121 (6)0.006 (4)−0.002 (4)0.012 (4)
C240.044 (4)0.059 (4)0.107 (5)−0.005 (4)−0.014 (4)0.014 (4)

Geometric parameters (Å, °)

N1—C61.367 (8)O8—C221.199 (8)
N1—C51.455 (9)O9—C241.355 (8)
N1—H1A0.8600O9—C181.433 (7)
C1—C21.500 (10)C9—C101.345 (8)
C1—H1B0.9600C9—C131.533 (8)
C1—H1C0.9600O10—C241.177 (8)
C1—H1D0.9600C10—C111.396 (8)
O1—N21.253 (15)C10—H10A0.9300
C2—C51.512 (10)O11—C151.415 (7)
C2—H2A0.9700O11—C141.463 (7)
C2—H2B0.9700C12—H12A0.9600
N2—O21.178 (15)C12—H12B0.9600
N2—C71.458 (10)C12—H12C0.9600
N3—O31.176 (7)C13—H13A0.9700
N3—O41.238 (7)C13—H13B0.9700
N3—C111.450 (8)C14—C181.522 (9)
C3—C41.484 (13)C14—H14A0.9800
C3—H3A0.9600C15—C161.513 (8)
C3—H3B0.9600C15—H15A0.9700
C3—H3C0.9600C15—H15B0.9700
N4—C141.393 (8)C16—C171.540 (8)
N4—C131.465 (9)C16—H16A0.9800
N4—H4A0.8600C17—C181.503 (8)
C4—C51.538 (11)C17—H17A0.9800
C4—H4B0.9700C18—H18A0.9800
C4—H4C0.9700C19—C201.427 (11)
O5—C201.231 (9)C19—H19A0.9600
C5—H5A0.9800C19—H19B0.9600
O6—C201.359 (8)C19—H19C0.9600
O6—C161.436 (7)C21—C221.509 (10)
C6—C71.416 (9)C21—H21A0.9600
C6—C111.446 (9)C21—H21B0.9600
C7—C81.386 (8)C21—H21C0.9600
O7—C221.339 (7)C23—C241.482 (10)
O7—C171.437 (7)C23—H23A0.9600
C8—C91.395 (8)C23—H23B0.9600
C8—C121.536 (9)C23—H23C0.9600
C6—N1—C5132.8 (6)C8—C12—H12C109.5
C6—N1—H1A113.6H12A—C12—H12C109.5
C5—N1—H1A113.6H12B—C12—H12C109.5
C2—C1—H1B109.5N4—C13—C9112.4 (6)
C2—C1—H1C109.5N4—C13—H13A109.1
H1B—C1—H1C109.5C9—C13—H13A109.1
C2—C1—H1D109.5N4—C13—H13B109.1
H1B—C1—H1D109.5C9—C13—H13B109.1
H1C—C1—H1D109.5H13A—C13—H13B107.9
C1—C2—C5115.8 (8)N4—C14—O11110.2 (5)
C1—C2—H2A108.3N4—C14—C18112.1 (6)
C5—C2—H2A108.3O11—C14—C18107.6 (4)
C1—C2—H2B108.3N4—C14—H14A109.0
C5—C2—H2B108.3O11—C14—H14A109.0
H2A—C2—H2B107.4C18—C14—H14A109.0
O2—N2—O1127.1 (11)O11—C15—C16109.3 (5)
O2—N2—C7120.6 (13)O11—C15—H15A109.8
O1—N2—C7112.2 (12)C16—C15—H15A109.8
O3—N3—O4120.3 (6)O11—C15—H15B109.8
O3—N3—C11119.1 (5)C16—C15—H15B109.8
O4—N3—C11120.5 (6)H15A—C15—H15B108.3
C4—C3—H3A109.5O6—C16—C15113.1 (5)
C4—C3—H3B109.5O6—C16—C17105.8 (4)
H3A—C3—H3B109.5C15—C16—C17108.4 (5)
C4—C3—H3C109.5O6—C16—H16A109.8
H3A—C3—H3C109.5C15—C16—H16A109.8
H3B—C3—H3C109.5C17—C16—H16A109.8
C14—N4—C13116.4 (6)O7—C17—C18108.1 (5)
C14—N4—H4A121.8O7—C17—C16107.4 (4)
C13—N4—H4A121.8C18—C17—C16110.1 (5)
C3—C4—C5112.4 (7)O7—C17—H17A110.4
C3—C4—H4B109.1C18—C17—H17A110.4
C5—C4—H4B109.1C16—C17—H17A110.4
C3—C4—H4C109.1O9—C18—C17107.1 (5)
C5—C4—H4C109.1O9—C18—C14108.4 (4)
H4B—C4—H4C107.9C17—C18—C14111.7 (5)
N1—C5—C2107.8 (6)O9—C18—H18A109.8
N1—C5—C4107.8 (6)C17—C18—H18A109.8
C2—C5—C4112.1 (6)C14—C18—H18A109.8
N1—C5—H5A109.7C20—C19—H19A109.5
C2—C5—H5A109.7C20—C19—H19B109.5
C4—C5—H5A109.7H19A—C19—H19B109.5
C20—O6—C16118.1 (5)C20—C19—H19C109.5
N1—C6—C7125.9 (6)H19A—C19—H19C109.5
N1—C6—C11121.0 (6)H19B—C19—H19C109.5
C7—C6—C11112.8 (5)O5—C20—O6117.9 (7)
C8—C7—C6124.8 (6)O5—C20—C19128.1 (7)
C8—C7—N2116.7 (6)O6—C20—C19113.7 (7)
C6—C7—N2118.5 (6)C22—C21—H21A109.5
C22—O7—C17118.2 (5)C22—C21—H21B109.5
C7—C8—C9119.1 (6)H21A—C21—H21B109.5
C7—C8—C12119.9 (6)C22—C21—H21C109.5
C9—C8—C12121.0 (5)H21A—C21—H21C109.5
C24—O9—C18119.5 (5)H21B—C21—H21C109.5
C10—C9—C8119.3 (5)O8—C22—O7123.7 (7)
C10—C9—C13121.2 (6)O8—C22—C21124.8 (7)
C8—C9—C13119.5 (6)O7—C22—C21111.5 (6)
C9—C10—C11122.3 (6)C24—C23—H23A109.5
C9—C10—H10A118.8C24—C23—H23B109.5
C11—C10—H10A118.8H23A—C23—H23B109.5
C15—O11—C14111.7 (5)C24—C23—H23C109.5
C10—C11—C6121.6 (6)H23A—C23—H23C109.5
C10—C11—N3116.4 (6)H23B—C23—H23C109.5
C6—C11—N3122.0 (5)O10—C24—O9121.1 (7)
C8—C12—H12A109.5O10—C24—C23127.6 (7)
C8—C12—H12B109.5O9—C24—C23111.2 (7)
H12A—C12—H12B109.5
C6—N1—C5—C2−145.8 (9)O4—N3—C11—C62.2 (10)
C6—N1—C5—C493.0 (11)C14—N4—C13—C995.8 (7)
C1—C2—C5—N168.2 (9)C10—C9—C13—N40.9 (9)
C1—C2—C5—C4−173.4 (7)C8—C9—C13—N4−178.2 (5)
C3—C4—C5—N1−170.6 (8)C13—N4—C14—O1166.0 (6)
C3—C4—C5—C271.0 (10)C13—N4—C14—C18−174.1 (5)
C5—N1—C6—C79.7 (15)C15—O11—C14—N4−174.5 (5)
C5—N1—C6—C11−176.7 (7)C15—O11—C14—C1863.1 (6)
N1—C6—C7—C8177.5 (8)C14—O11—C15—C16−66.7 (6)
C11—C6—C7—C83.4 (12)C20—O6—C16—C1591.4 (7)
N1—C6—C7—N2−5.1 (14)C20—O6—C16—C17−150.0 (6)
C11—C6—C7—N2−179.2 (9)O11—C15—C16—O6177.2 (4)
O2—N2—C7—C885.5 (12)O11—C15—C16—C1760.2 (6)
O1—N2—C7—C8−91.0 (9)C22—O7—C17—C18114.5 (6)
O2—N2—C7—C6−92.1 (11)C22—O7—C17—C16−126.7 (5)
O1—N2—C7—C691.4 (10)O6—C16—C17—O766.9 (6)
C6—C7—C8—C9−5.2 (12)C15—C16—C17—O7−171.5 (5)
N2—C7—C8—C9177.4 (9)O6—C16—C17—C18−175.6 (5)
C6—C7—C8—C12177.2 (8)C15—C16—C17—C18−54.1 (6)
N2—C7—C8—C12−0.3 (12)C24—O9—C18—C17125.1 (6)
C7—C8—C9—C104.1 (10)C24—O9—C18—C14−114.2 (6)
C12—C8—C9—C10−178.3 (6)O7—C17—C18—O9−70.9 (6)
C7—C8—C9—C13−176.8 (7)C16—C17—C18—O9172.1 (4)
C12—C8—C9—C130.8 (10)O7—C17—C18—C14170.5 (5)
C8—C9—C10—C11−1.7 (10)C16—C17—C18—C1453.5 (6)
C13—C9—C10—C11179.2 (7)N4—C14—C18—O964.8 (7)
C9—C10—C11—C60.2 (10)O11—C14—C18—O9−173.9 (5)
C9—C10—C11—N3−179.7 (6)N4—C14—C18—C17−177.4 (5)
N1—C6—C11—C10−175.3 (7)O11—C14—C18—C17−56.1 (6)
C7—C6—C11—C10−0.9 (10)C16—O6—C20—O5−12.9 (12)
N1—C6—C11—N34.6 (11)C16—O6—C20—C19172.6 (7)
C7—C6—C11—N3179.0 (7)C17—O7—C22—O8−4.5 (9)
O3—N3—C11—C100.2 (10)C17—O7—C22—C21175.2 (5)
O4—N3—C11—C10−177.9 (7)C18—O9—C24—O10−1.5 (10)
O3—N3—C11—C6−179.7 (7)C18—O9—C24—C23−178.9 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.861.922.621 (8)138

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ER2053).

References

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