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

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ISSN: 2056-9890

3,19-Di­acetyl-12-nitro­methyl-14-de­oxy­andrographolide

aCollege of Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: yaocheng@njut.edu.cn

(Received 15 October 2009; accepted 23 October 2009; online 31 October 2009)

In the crystal of the title compound, C24H33NO9, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules.

Related literature

For general background, see: Thunuguntla et al. (2004[Thunuguntla, S. S. R., Nyavanandi, V. K. & Nanduri, S. (2004). Tetrahedron Lett. 45, 9357-9360.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C24H33NO9

  • Mr = 479.51

  • Monoclinic, P 21

  • a = 10.533 (2) Å

  • b = 12.756 (3) Å

  • c = 10.659 (2) Å

  • β = 117.04 (3)°

  • V = 1275.6 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 2565 measured reflections

  • 2431 independent reflections

  • 1945 reflections with I > 2σ(I)

  • Rint = 0.024

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 0.199

  • S = 1.00

  • 2431 reflections

  • 302 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.69 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15A⋯O8i 0.97 2.59 3.312 (18) 131
C22—H22A⋯O9ii 0.97 2.47 3.388 (13) 158
C22—H22B⋯O1iii 0.97 2.51 3.301 (13) 139
C24—H24B⋯O3iv 0.97 2.56 3.376 (9) 142
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iv) x+1, y, z.

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: SHELXL97.

Supporting information


Related literature top

For general background, see: Thunuguntla et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

Andrographolide (15 g) and nitromethane (20 ml) in dry methanol were stired in the presence of sodium methoxide at room temperature for 3 h. After confirming the completion of reaction, the mixture was washed with brine. The organic phase was evaporated in vacuo, and the residue was recrystallized by ethyl acrtate. The product (10 g) and acetic anhydride (20 ml) was refluxed for 10 min. After confirming the completion of reaction, the mixture was washed with brine. The organic phase was evaporated in vacuo to afford corresponding product by flash chromatography. Colourless blocks of (I) were recrystallised from ethyl acetate.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.97Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

The deepest difference hole is 0.12Å from the N atom and the highest difference peak is 0.18Å from atom O9.

Structure description top

For general background, see: Thunuguntla et al. (2004). For bond-length data, see: Allen et al. (1987).

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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.
3,19-Diacetyl-12-nitromethyl-14-deoxyandrographolide top
Crystal data top
C24H33NO9F(000) = 512
Mr = 479.51Dx = 1.248 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 10.533 (2) Åθ = 9–12°
b = 12.756 (3) ŵ = 0.10 mm1
c = 10.659 (2) ÅT = 293 K
β = 117.04 (3)°Block, colourless
V = 1275.6 (4) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 25.3°, θmin = 2.2°
Graphite monochromatorh = 1112
ω/2θ scansk = 150
2565 measured reflectionsl = 120
2431 independent reflections3 standard reflections every 200 reflections
1945 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072H-atom parameters constrained
wR(F2) = 0.199 w = 1/[σ2(Fo2) + (0.1P)2 + 1.120P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2431 reflectionsΔρmax = 0.69 e Å3
302 parametersΔρmin = 0.48 e Å3
14 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.063 (8)
Crystal data top
C24H33NO9V = 1275.6 (4) Å3
Mr = 479.51Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.533 (2) ŵ = 0.10 mm1
b = 12.756 (3) ÅT = 293 K
c = 10.659 (2) Å0.30 × 0.20 × 0.20 mm
β = 117.04 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.024
2565 measured reflections3 standard reflections every 200 reflections
2431 independent reflections intensity decay: 1%
1945 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.07214 restraints
wR(F2) = 0.199H-atom parameters constrained
S = 1.00Δρmax = 0.69 e Å3
2431 reflectionsΔρmin = 0.48 e Å3
302 parameters
Special details top

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 > 2sigma(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
N0.7992 (9)0.3512 (6)0.7140 (12)0.1177 (19)
O10.1814 (7)0.3398 (4)0.6418 (6)0.0915 (17)
C10.0804 (12)0.4065 (7)0.7867 (12)0.108 (3)
H1A0.07690.47280.74270.162*
H1B0.13870.41270.88660.162*
H1C0.01430.38590.76790.162*
O20.1466 (6)0.2330 (3)0.7887 (5)0.0719 (13)
C20.1425 (7)0.3259 (5)0.7293 (8)0.0645 (16)
O30.1429 (6)0.0145 (5)0.8828 (7)0.0935 (18)
C30.1806 (8)0.1612 (7)0.9391 (9)0.084 (2)
H3A0.26680.13420.93650.126*
H3B0.20330.21600.87040.126*
H3C0.12070.18871.03120.126*
O40.0165 (4)0.1100 (3)0.9106 (4)0.0555 (10)
C40.1040 (7)0.0749 (5)0.9066 (6)0.0587 (15)
C50.1112 (7)0.0355 (5)0.8929 (6)0.0559 (14)
H5A0.08130.03500.90110.067*
H5B0.20700.04540.96810.067*
C60.1141 (6)0.0463 (5)0.7499 (5)0.0470 (12)
O50.3609 (8)0.3524 (5)0.7817 (8)0.115 (2)
C70.1806 (6)0.0527 (4)0.7167 (5)0.0424 (12)
H7A0.16590.04120.62010.051*
O60.4623 (8)0.1819 (6)0.3207 (5)0.106 (2)
C80.3456 (6)0.0689 (4)0.8036 (5)0.0456 (12)
O70.4337 (11)0.3352 (6)0.4088 (7)0.145 (3)
O80.8651 (14)0.3399 (8)0.6600 (15)0.218 (7)
C90.4175 (7)0.0340 (5)0.7949 (8)0.0644 (16)
H9A0.51870.02940.85800.077*
H9B0.40630.04200.69990.077*
O90.7740 (7)0.4391 (5)0.7441 (9)0.1177 (19)
C100.3570 (7)0.1318 (5)0.8330 (8)0.0655 (17)
H10A0.37760.12800.93130.079*
H10B0.40380.19370.82090.079*
C110.2003 (7)0.1420 (4)0.7444 (7)0.0558 (14)
H11A0.18170.15270.64650.067*
C120.0425 (6)0.0581 (5)0.6332 (6)0.0596 (15)
H12A0.04330.06590.54330.089*
H12B0.08480.11880.65230.089*
H12C0.09590.00320.63210.089*
C130.3944 (7)0.0991 (5)0.9598 (6)0.0595 (15)
H13A0.36760.04471.00530.089*
H13B0.49610.10751.00660.089*
H13C0.34980.16370.96400.089*
C140.0996 (6)0.1543 (4)0.7078 (6)0.0522 (13)
H14A0.00170.14260.65050.063*
H14B0.11500.17430.80140.063*
C150.1489 (7)0.2431 (5)0.6436 (7)0.0616 (16)
H15A0.10090.30750.64530.074*
H15B0.12340.22670.54620.074*
C160.3051 (6)0.2581 (5)0.7227 (6)0.0524 (13)
C170.3904 (6)0.1603 (4)0.7310 (6)0.0467 (12)
H17A0.35920.13790.63340.056*
C180.5504 (6)0.1759 (5)0.7935 (6)0.0554 (13)
H18A0.58370.20950.88470.066*
H18B0.59590.10780.80860.066*
C190.5979 (6)0.2425 (5)0.7016 (6)0.0526 (14)
H19A0.54790.30980.68360.063*
C200.5592 (6)0.1911 (5)0.5610 (6)0.0524 (13)
C210.4825 (11)0.2478 (8)0.4296 (8)0.087 (2)
C220.5278 (9)0.0844 (7)0.3765 (9)0.088 (2)
H22A0.45870.02790.34150.105*
H22B0.60360.07010.35110.105*
C230.5853 (8)0.0952 (6)0.5302 (8)0.0693 (17)
H23A0.63260.04280.59570.083*
C240.7548 (7)0.2639 (5)0.7812 (8)0.0649 (16)
H24A0.77840.28300.87740.078*
H24B0.80720.20080.78380.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.109 (3)0.059 (2)0.196 (6)0.008 (3)0.079 (4)0.003 (3)
O10.128 (5)0.059 (3)0.100 (4)0.001 (3)0.062 (4)0.019 (3)
C10.147 (8)0.051 (4)0.152 (9)0.012 (5)0.090 (7)0.001 (5)
O20.112 (4)0.036 (2)0.090 (3)0.001 (2)0.066 (3)0.002 (2)
C20.068 (4)0.037 (3)0.083 (4)0.001 (3)0.030 (3)0.007 (3)
O30.114 (4)0.073 (3)0.120 (4)0.029 (3)0.077 (4)0.020 (3)
C30.072 (4)0.097 (6)0.093 (5)0.009 (4)0.046 (4)0.015 (5)
O40.066 (2)0.047 (2)0.062 (2)0.0022 (19)0.037 (2)0.0078 (18)
C40.069 (4)0.061 (4)0.054 (3)0.009 (3)0.035 (3)0.007 (3)
C50.072 (4)0.055 (3)0.051 (3)0.006 (3)0.036 (3)0.001 (3)
C60.061 (3)0.043 (3)0.040 (3)0.001 (3)0.026 (2)0.000 (2)
O50.157 (6)0.081 (4)0.128 (5)0.010 (4)0.082 (5)0.007 (4)
C70.049 (3)0.044 (3)0.036 (2)0.002 (2)0.021 (2)0.001 (2)
O60.155 (6)0.095 (4)0.065 (3)0.007 (4)0.048 (3)0.000 (3)
C80.051 (3)0.043 (3)0.044 (3)0.002 (2)0.022 (2)0.005 (2)
O70.241 (9)0.085 (5)0.084 (4)0.049 (6)0.054 (5)0.028 (4)
O80.294 (13)0.122 (7)0.410 (18)0.038 (8)0.310 (15)0.057 (9)
C90.062 (3)0.044 (3)0.092 (5)0.008 (3)0.039 (3)0.005 (3)
O90.109 (3)0.059 (2)0.196 (6)0.008 (3)0.079 (4)0.003 (3)
C100.075 (4)0.038 (3)0.088 (5)0.010 (3)0.040 (4)0.011 (3)
C110.078 (4)0.036 (3)0.062 (3)0.002 (3)0.040 (3)0.000 (3)
C120.065 (3)0.058 (4)0.053 (3)0.008 (3)0.023 (3)0.002 (3)
C130.072 (4)0.060 (4)0.044 (3)0.009 (3)0.023 (3)0.006 (3)
C140.053 (3)0.048 (3)0.061 (3)0.003 (3)0.030 (3)0.007 (3)
C150.059 (4)0.054 (4)0.073 (4)0.010 (3)0.031 (3)0.019 (3)
C160.065 (4)0.044 (3)0.056 (3)0.001 (3)0.034 (3)0.007 (2)
C170.051 (3)0.045 (3)0.046 (3)0.003 (2)0.024 (2)0.001 (2)
C180.056 (3)0.054 (3)0.054 (3)0.003 (3)0.023 (3)0.003 (3)
C190.053 (3)0.045 (3)0.062 (3)0.004 (3)0.029 (3)0.001 (3)
C200.055 (3)0.044 (3)0.066 (3)0.007 (3)0.034 (3)0.001 (3)
C210.114 (6)0.082 (6)0.069 (5)0.005 (5)0.044 (4)0.006 (4)
C220.104 (6)0.083 (6)0.099 (5)0.020 (5)0.066 (5)0.033 (5)
C230.076 (4)0.059 (4)0.085 (5)0.003 (3)0.048 (4)0.000 (3)
C240.058 (4)0.047 (3)0.085 (4)0.006 (3)0.029 (3)0.005 (3)
Geometric parameters (Å, º) top
N—O81.094 (10)C9—H9B0.9700
N—O91.228 (10)C10—C111.488 (9)
N—C241.508 (10)C10—H10A0.9700
O1—C21.190 (8)C10—H10B0.9700
C1—C21.492 (11)C11—H11A0.9800
C1—H1A0.9600C12—H12A0.9600
C1—H1B0.9600C12—H12B0.9600
C1—H1C0.9600C12—H12C0.9600
O2—C21.335 (7)C13—H13A0.9600
O2—C111.460 (7)C13—H13B0.9600
O3—C41.200 (8)C13—H13C0.9600
C3—C41.495 (10)C14—C151.531 (8)
C3—H3A0.9600C14—H14A0.9700
C3—H3B0.9600C14—H14B0.9700
C3—H3C0.9600C15—C161.481 (9)
O4—C41.327 (7)C15—H15A0.9700
O4—C51.451 (7)C15—H15B0.9700
C5—C61.544 (7)C16—C171.517 (8)
C5—H5A0.9700C17—C181.518 (7)
C5—H5B0.9700C17—H17A0.9800
C6—C111.538 (8)C18—C191.541 (8)
C6—C121.557 (8)C18—H18A0.9700
C6—C71.561 (8)C18—H18B0.9700
O5—C161.361 (9)C19—C241.500 (8)
C7—C141.530 (8)C19—C201.512 (8)
C7—C81.568 (7)C19—H19A0.9800
C7—H7A0.9800C20—C231.328 (9)
O6—C211.369 (10)C20—C211.452 (10)
O6—C221.416 (12)C22—C231.473 (11)
C8—C91.539 (8)C22—H22A0.9700
C8—C131.551 (8)C22—H22B0.9700
C8—C171.585 (7)C23—H23A0.9300
O7—C211.205 (12)C24—H24A0.9700
C9—C101.538 (9)C24—H24B0.9700
C9—H9A0.9700
O8—N—O9121.4 (10)C6—C12—H12A109.5
O8—N—C24124.1 (9)C6—C12—H12B109.5
O9—N—C24113.5 (9)H12A—C12—H12B109.5
C2—C1—H1A109.5C6—C12—H12C109.5
C2—C1—H1B109.5H12A—C12—H12C109.5
H1A—C1—H1B109.5H12B—C12—H12C109.5
C2—C1—H1C109.5C8—C13—H13A109.5
H1A—C1—H1C109.5C8—C13—H13B109.5
H1B—C1—H1C109.5H13A—C13—H13B109.5
C2—O2—C11119.1 (5)C8—C13—H13C109.5
O1—C2—O2123.8 (7)H13A—C13—H13C109.5
O1—C2—C1126.2 (7)H13B—C13—H13C109.5
O2—C2—C1110.1 (6)C7—C14—C15111.2 (5)
C4—C3—H3A109.5C7—C14—H14A109.4
C4—C3—H3B109.5C15—C14—H14A109.4
H3A—C3—H3B109.5C7—C14—H14B109.4
C4—C3—H3C109.5C15—C14—H14B109.4
H3A—C3—H3C109.5H14A—C14—H14B108.0
H3B—C3—H3C109.5C16—C15—C14110.9 (5)
C4—O4—C5118.6 (5)C16—C15—H15A109.5
O3—C4—O4123.9 (6)C14—C15—H15A109.5
O3—C4—C3125.5 (7)C16—C15—H15B109.5
O4—C4—C3110.7 (6)C14—C15—H15B109.5
O4—C5—C6113.2 (5)H15A—C15—H15B108.1
O4—C5—H5A108.9O5—C16—C15120.8 (6)
C6—C5—H5A108.9O5—C16—C17125.5 (6)
O4—C5—H5B108.9C15—C16—C17113.7 (5)
C6—C5—H5B108.9C16—C17—C18115.3 (5)
H5A—C5—H5B107.8C16—C17—C8109.5 (4)
C11—C6—C5112.6 (5)C18—C17—C8113.6 (4)
C11—C6—C12108.8 (5)C16—C17—H17A105.9
C5—C6—C12108.0 (4)C18—C17—H17A105.9
C11—C6—C7107.5 (4)C8—C17—H17A105.9
C5—C6—C7111.3 (4)C17—C18—C19114.2 (5)
C12—C6—C7108.6 (4)C17—C18—H18A108.7
C14—C7—C6113.9 (4)C19—C18—H18A108.7
C14—C7—C8111.2 (4)C17—C18—H18B108.7
C6—C7—C8117.7 (4)C19—C18—H18B108.7
C14—C7—H7A104.1H18A—C18—H18B107.6
C6—C7—H7A104.1C24—C19—C20111.7 (5)
C8—C7—H7A104.1C24—C19—C18109.5 (5)
C21—O6—C22109.0 (6)C20—C19—C18111.9 (5)
C9—C8—C13110.1 (5)C24—C19—H19A107.9
C9—C8—C7107.2 (4)C20—C19—H19A107.9
C13—C8—C7113.8 (4)C18—C19—H19A107.9
C9—C8—C17109.5 (4)C23—C20—C21107.9 (6)
C13—C8—C17108.3 (4)C23—C20—C19130.6 (6)
C7—C8—C17107.7 (4)C21—C20—C19121.5 (6)
C10—C9—C8113.7 (5)O7—C21—O6121.6 (8)
C10—C9—H9A108.8O7—C21—C20129.9 (8)
C8—C9—H9A108.8O6—C21—C20108.4 (7)
C10—C9—H9B108.8O6—C22—C23105.1 (6)
C8—C9—H9B108.8O6—C22—H22A110.7
H9A—C9—H9B107.7C23—C22—H22A110.7
C11—C10—C9112.1 (5)O6—C22—H22B110.7
C11—C10—H10A109.2C23—C22—H22B110.7
C9—C10—H10A109.2H22A—C22—H22B108.8
C11—C10—H10B109.2C20—C23—C22109.5 (7)
C9—C10—H10B109.2C20—C23—H23A125.2
H10A—C10—H10B107.9C22—C23—H23A125.2
O2—C11—C10110.2 (5)C19—C24—N111.5 (6)
O2—C11—C6107.2 (4)C19—C24—H24A109.3
C10—C11—C6114.2 (5)N—C24—H24A109.3
O2—C11—H11A108.4C19—C24—H24B109.3
C10—C11—H11A108.4N—C24—H24B109.3
C6—C11—H11A108.4H24A—C24—H24B108.0
C11—O2—C2—O10.7 (10)C7—C14—C15—C1655.1 (7)
C11—O2—C2—C1178.3 (7)C14—C15—C16—O5122.3 (7)
C5—O4—C4—O33.5 (9)C14—C15—C16—C1757.0 (7)
C5—O4—C4—C3175.1 (5)O5—C16—C17—C188.8 (8)
C4—O4—C5—C6108.6 (6)C15—C16—C17—C18172.0 (5)
O4—C5—C6—C1175.4 (6)O5—C16—C17—C8120.8 (6)
O4—C5—C6—C1244.7 (7)C15—C16—C17—C858.5 (6)
O4—C5—C6—C7163.8 (4)C9—C8—C17—C16172.8 (5)
C11—C6—C7—C14175.9 (5)C13—C8—C17—C1667.1 (6)
C5—C6—C7—C1460.3 (6)C7—C8—C17—C1656.5 (5)
C12—C6—C7—C1458.4 (6)C9—C8—C17—C1856.7 (6)
C11—C6—C7—C851.4 (5)C13—C8—C17—C1863.4 (6)
C5—C6—C7—C872.4 (6)C7—C8—C17—C18173.0 (4)
C12—C6—C7—C8168.9 (4)C16—C17—C18—C1967.9 (6)
C14—C7—C8—C9174.9 (5)C8—C17—C18—C19164.6 (5)
C6—C7—C8—C951.2 (6)C17—C18—C19—C24173.0 (5)
C14—C7—C8—C1363.1 (6)C17—C18—C19—C2062.6 (7)
C6—C7—C8—C1370.8 (6)C24—C19—C20—C2370.8 (8)
C14—C7—C8—C1757.1 (5)C18—C19—C20—C2352.4 (8)
C6—C7—C8—C17169.0 (4)C24—C19—C20—C21108.2 (7)
C13—C8—C9—C1073.4 (7)C18—C19—C20—C21128.6 (7)
C7—C8—C9—C1050.9 (7)C22—O6—C21—O7178.3 (11)
C17—C8—C9—C10167.6 (5)C22—O6—C21—C202.0 (9)
C8—C9—C10—C1156.1 (8)C23—C20—C21—O7176.9 (12)
C2—O2—C11—C1089.9 (7)C19—C20—C21—O73.9 (16)
C2—O2—C11—C6145.2 (5)C23—C20—C21—O60.9 (9)
C9—C10—C11—O2177.3 (5)C19—C20—C21—O6179.9 (6)
C9—C10—C11—C656.5 (7)C21—O6—C22—C232.2 (9)
C5—C6—C11—O251.7 (6)C21—C20—C23—C220.5 (8)
C12—C6—C11—O268.0 (6)C19—C20—C23—C22178.6 (6)
C7—C6—C11—O2174.6 (5)O6—C22—C23—C201.7 (8)
C5—C6—C11—C1070.7 (6)C20—C19—C24—N70.7 (7)
C12—C6—C11—C10169.6 (5)C18—C19—C24—N164.7 (6)
C7—C6—C11—C1052.3 (6)O8—N—C24—C19110.7 (14)
C6—C7—C14—C15167.4 (5)O9—N—C24—C1980.2 (10)
C8—C7—C14—C1556.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O8i0.972.593.312 (18)131
C22—H22A···O9ii0.972.473.388 (13)158
C22—H22B···O1iii0.972.513.301 (13)139
C24—H24B···O3iv0.972.563.376 (9)142
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1; (iii) x+1, y1/2, z+1; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC24H33NO9
Mr479.51
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)10.533 (2), 12.756 (3), 10.659 (2)
β (°) 117.04 (3)
V3)1275.6 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2565, 2431, 1945
Rint0.024
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.199, 1.00
No. of reflections2431
No. of parameters302
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.69, 0.48

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
C15—H15A···O8i0.972.593.312 (18)131
C22—H22A···O9ii0.972.473.388 (13)158
C22—H22B···O1iii0.972.513.301 (13)139
C24—H24B···O3iv0.972.563.376 (9)142
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1; (iii) x+1, y1/2, z+1; (iv) x+1, y, z.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationThunuguntla, S. S. R., Nyavanandi, V. K. & Nanduri, S. (2004). Tetrahedron Lett. 45, 9357–9360.  CAS Google Scholar

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