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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aJiangsu Key Laboratory of Chinese Medicine Processing, Nanjing University of Chinese Medicine, Nanjing 210029, People's Republic of China, and bState Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Hankou Road, Nanjing 210093, People's Republic of China
*Correspondence e-mail: bccai@hotmail.com

(Received 2 April 2008; accepted 23 July 2008; online 31 July 2008)

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[Grichar, W. J. & Dotray, P. A. (2007). Crop Prot. 26, 1826-1830.]); Kubátová et al. (2006[Kubátová, A., Dronen, L. C. & Hawthorne, S. B. (2006). Environ. Toxicol. Chem. 25, 1742-1745.]); Wang et al. (2008[Wang, X., Li, X., Yin, Y., Pang, Y. & Yang, Y. (2008). Acta Cryst. E64, o669.]); Yang et al. (2004[Yang, B., Zhang, S.-S., Wang, Y.-F., Li, X.-M., Jiao, K., Kassim, M. & Yamin, B. M. (2004). Acta Cryst. E60, o1902-o1904.]).

[Scheme 1]

Experimental

Crystal data
  • C24H34N4O11

  • Mr = 554.55

  • Orthorhombic, P 21 21 21

  • 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[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]) Tmin = 0.969, Tmax = 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[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O4 0.86 1.92 2.621 (8) 138

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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

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°.

Related literature top

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

Experimental top

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 top

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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
3-Methyl-2,6-dinitro-N-(3-pentyl)-4-[(2,3,4-tri-O- acetyl-β-D-xylosyl)aminomethyl]aniline top
Crystal data top
C24H34N4O11F(000) = 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 = 10–13°
b = 11.044 (2) ŵ = 0.11 mm1
c = 34.106 (7) ÅT = 293 K
V = 2791.1 (10) Å3Block, yellow
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1662 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.1°, θmin = 1.2°
ω/2θ scansh = 08
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
k = 013
Tmin = 0.969, Tmax = 0.990l = 040
2870 measured reflections3 standard reflections every 200 reflections
2870 independent reflections intensity decay: none
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1035P)2]
where P = (Fo2 + 2Fc2)/3
2870 reflections(Δ/σ)max < 0.001
352 parametersΔρmax = 0.18 e Å3
13 restraintsΔρmin = 0.23 e Å3
Crystal data top
C24H34N4O11V = 2791.1 (10) Å3
Mr = 554.55Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.4100 (15) ŵ = 0.11 mm1
b = 11.044 (2) ÅT = 293 K
c = 34.106 (7) Å0.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1662 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
Rint = 0.000
Tmin = 0.969, Tmax = 0.9903 standard reflections every 200 reflections
2870 measured reflections intensity decay: none
2870 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06713 restraints
wR(F2) = 0.196H-atom parameters constrained
S = 1.04Δρmax = 0.18 e Å3
2870 reflectionsΔρmin = 0.23 e Å3
352 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*/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)
H19A0.99221.29570.04420.157*
H19B0.91131.16620.05110.157*
H19C1.12021.18670.05390.157*
C201.0292 (12)1.1850 (6)0.0003 (3)0.080 (2)
C211.6071 (11)0.9433 (6)0.0209 (2)0.077 (2)
H21A1.64190.89860.04380.115*
H21B1.70180.93910.00170.115*
H21C1.58601.02630.02780.115*
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) top
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, º) top
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—C2145.8 (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—C4173.4 (7)C8—C9—C13—N4178.2 (5)
C3—C4—C5—N1170.6 (8)C13—N4—C14—O1166.0 (6)
C3—C4—C5—C271.0 (10)C13—N4—C14—C18174.1 (5)
C5—N1—C6—C79.7 (15)C15—O11—C14—N4174.5 (5)
C5—N1—C6—C11176.7 (7)C15—O11—C14—C1863.1 (6)
N1—C6—C7—C8177.5 (8)C14—O11—C15—C1666.7 (6)
C11—C6—C7—C83.4 (12)C20—O6—C16—C1591.4 (7)
N1—C6—C7—N25.1 (14)C20—O6—C16—C17150.0 (6)
C11—C6—C7—N2179.2 (9)O11—C15—C16—O6177.2 (4)
O2—N2—C7—C885.5 (12)O11—C15—C16—C1760.2 (6)
O1—N2—C7—C891.0 (9)C22—O7—C17—C18114.5 (6)
O2—N2—C7—C692.1 (11)C22—O7—C17—C16126.7 (5)
O1—N2—C7—C691.4 (10)O6—C16—C17—O766.9 (6)
C6—C7—C8—C95.2 (12)C15—C16—C17—O7171.5 (5)
N2—C7—C8—C9177.4 (9)O6—C16—C17—C18175.6 (5)
C6—C7—C8—C12177.2 (8)C15—C16—C17—C1854.1 (6)
N2—C7—C8—C120.3 (12)C24—O9—C18—C17125.1 (6)
C7—C8—C9—C104.1 (10)C24—O9—C18—C14114.2 (6)
C12—C8—C9—C10178.3 (6)O7—C17—C18—O970.9 (6)
C7—C8—C9—C13176.8 (7)C16—C17—C18—O9172.1 (4)
C12—C8—C9—C130.8 (10)O7—C17—C18—C14170.5 (5)
C8—C9—C10—C111.7 (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—O9173.9 (5)
C9—C10—C11—N3179.7 (6)N4—C14—C18—C17177.4 (5)
N1—C6—C11—C10175.3 (7)O11—C14—C18—C1756.1 (6)
C7—C6—C11—C100.9 (10)C16—O6—C20—O512.9 (12)
N1—C6—C11—N34.6 (11)C16—O6—C20—C19172.6 (7)
C7—C6—C11—N3179.0 (7)C17—O7—C22—O84.5 (9)
O3—N3—C11—C100.2 (10)C17—O7—C22—C21175.2 (5)
O4—N3—C11—C10177.9 (7)C18—O9—C24—O101.5 (10)
O3—N3—C11—C6179.7 (7)C18—O9—C24—C23178.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.861.922.621 (8)138

Experimental details

Crystal data
Chemical formulaC24H34N4O11
Mr554.55
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.4100 (15), 11.044 (2), 34.106 (7)
V3)2791.1 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(XCAD4; Harms & Wocadlo, 1995)
Tmin, Tmax0.969, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
2870, 2870, 1662
Rint0.000
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.196, 1.04
No. of reflections2870
No. of parameters352
No. of restraints13
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.861.922.621 (8)137.5
 

References

First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationGrichar, W. J. & Dotray, P. A. (2007). Crop Prot. 26, 1826–1830.  Web of Science CrossRef CAS Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationKubátová, A., Dronen, L. C. & Hawthorne, S. B. (2006). Environ. Toxicol. Chem. 25, 1742–1745.  Web of Science PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, X., Li, X., Yin, Y., Pang, Y. & Yang, Y. (2008). Acta Cryst. E64, o669.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYang, B., Zhang, S.-S., Wang, Y.-F., Li, X.-M., Jiao, K., Kassim, M. & Yamin, B. M. (2004). Acta Cryst. E60, o1902–o1904.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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