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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,3-Dioxo-2,3-di­hydro-1H-isoindol-2-yl 2,3,4-tri-O-acetyl-β-D-xyloside

aState Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, People's Republic of China, and bCollege of Landscape Architecture, Nanjing Forestry University, Nanjing 210037, People's Republic of China
*Correspondence e-mail: wangxm07@nju.edu.cn, yangyh@nju.edu.cn

(Received 27 October 2011; accepted 2 February 2012; online 10 February 2012)

The title compound, C19H19NO10, was obtained from the reaction of α-D-1-bromo-2,3,4-tri-O-acetylxylose with N-hy­droxy­phthalimide in the presence of potassium carbonate. The asymmetric unit contains two independent mol­ecules, in which the O—CH—O—N torsion angles are 73.0 (4) and 65.0 (4)°. The hexa­pyranosyl rings adopt chair conformations and the substituent groups are in equatorial positions. In the crystal, mol­ecules are linked by nonclassical C—H⋯O hydrogen bonds.

Related literature

For related structures, see: 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.]); Wang et al. (2008[Wang, X., Li, X., Yin, Y., Pang, Y. & Yang, Y. (2008). Acta Cryst. E64, o669.]); Bai et al. (2008[Bai, L., Wang, X. & Cai, B. (2008). Acta Cryst. E64, o1623.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19NO10

  • Mr = 421.35

  • Monoclinic, P 21

  • a = 11.722 (2) Å

  • b = 9.2270 (18) Å

  • c = 19.615 (4) Å

  • β = 104.52 (3)°

  • V = 2053.8 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 295 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.957, Tmax = 0.978

  • 4180 measured reflections

  • 3977 independent reflections

  • 2784 reflections with I > 2σ(I)

  • Rint = 0.058

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

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.131

  • S = 1.00

  • 3977 reflections

  • 541 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11A⋯O15i 0.98 2.42 3.339 (6) 157
C22—H22A⋯O1ii 0.96 2.39 3.329 (7) 165
C26—H26A⋯O3iii 0.98 2.54 3.385 (6) 144
C30—H30B⋯O5 0.97 2.56 3.429 (6) 149
C35—H35⋯O5iv 0.93 2.54 3.294 (8) 138
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) x, y+1, z; (iv) [-x+1, y-{\script{1\over 2}}, -z].

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the present work, the structure of 2,3,4-tri-O-acetyl-β-D-xyloside-N-hydroxyphthalimide, I, has been determined (Fig. 1). The asymmetric unit of I contains two independent molecules. The molecules are twisted at the CH–O bonds with the O7–C8–O8–N1 and O17–C29–O18–N2 torsion angles of 73.0 (4)° (molecule 1) and 65.0 (4)° (molecule 2), respectively. The bond lengths and angles in the title molecules show normal values. The hexapyranosyl ring adopts chair conformation (Fig. 1) and the substituented groups are individually planar and occupy equatorial positions (Yang et al., 2004; Wang et al., 2008; Bai et al., 2008).

Related literature top

For related structures, see: Yang et al. (2004); Wang et al. (2008); Bai et al. (2008).

Experimental top

The solution of α-D-1-bromo-2,3,4-tri-O-acetyl-xylose (0.1 mol) and N-hydroxyphthalimide (0.1 mol) in chloroform (100 ml) and water (100 ml) was treated with sodium carbonate (0.1 mol) with triethyl benzyl ammonium chloride in present at room temperature overnight. The chloroform layer was separated, washed with water and allowed to evaporate slowly. The residual 2,3,4-tri-O-acetyl-β-D-xyloside-N- hydroxyphthalimide was then recrystallized to constant melting point (m.p. 455.6-456 K) from ethyl acetate. The purity of the compound was checked and characterized by NMR spectra. Fine block colourless crystals for X-ray diffraction were obtained by slow evaporation of an ethyl acetate at room temperature. 1H NMR, 500 MHz, CDCl3, δ: 8.15 (d, J = 9.6 Hz, 1H, Ar–H), 7.85 (d, J = 9.3 Hz, 1H, Ar–H), 5.82(d, J = 8.2 Hz, 1H, G–H), 5.25 (t, J = 9.9 Hz, 1H, G–H), 4.87(t, J = 9.6 Hz, 1H, G–H), 4.62 (t, J = 9.0 Hz, 1H, G–H), 3.80 (m, 2H, G–H), 2.14, 2.12, 2.09 (3s, COCH3).

Refinement top

Hydrogen atoms were placed in calculated positions with appropriate riding models: C–H = 0.96Å for methyl H; C–H = 0.93Å for aryl H; C–H = 0.98Å for methine H and Uiso(H) = 1.2(1.5)Ueq(C). The atom C25 restrictive refinement by AFIX2 command.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (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. H atoms are presented as a small spheres of arbitrary radius.
1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl 2,3,4-tri-O-acetyl-β-D-xyloside top
Crystal data top
C19H19NO10F(000) = 880
Mr = 421.35Dx = 1.363 Mg m3
Monoclinic, P21Melting point = 455.6–456 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 11.722 (2) ÅCell parameters from 25 reflections
b = 9.2270 (18) Åθ = 9–12°
c = 19.615 (4) ŵ = 0.11 mm1
β = 104.52 (3)°T = 295 K
V = 2053.8 (7) Å3Block, colourless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2784 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 25.3°, θmin = 1.1°
ω/2θ scansh = 1413
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.957, Tmax = 0.978l = 023
4180 measured reflections3 standard reflections every 200 reflections
3977 independent reflections intensity decay: 1%
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) = 0.131H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0835P)2]
where P = (Fo2 + 2Fc2)/3
3977 reflections(Δ/σ)max < 0.001
541 parametersΔρmax = 0.24 e Å3
6 restraintsΔρmin = 0.22 e Å3
Crystal data top
C19H19NO10V = 2053.8 (7) Å3
Mr = 421.35Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.722 (2) ŵ = 0.11 mm1
b = 9.2270 (18) ÅT = 295 K
c = 19.615 (4) Å0.40 × 0.30 × 0.20 mm
β = 104.52 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2784 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.058
Tmin = 0.957, Tmax = 0.9783 standard reflections every 200 reflections
4180 measured reflections intensity decay: 1%
3977 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0476 restraints
wR(F2) = 0.131H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å3
3977 reflectionsΔρmin = 0.22 e Å3
541 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C10.7869 (7)0.0615 (11)0.5590 (4)0.122 (3)
H1A0.70570.07520.53470.183*
H1B0.79190.02930.60620.183*
H1C0.82860.15140.56040.183*
O10.8981 (5)0.1670 (8)0.5445 (3)0.134 (2)
O20.8245 (3)0.0151 (4)0.45501 (15)0.0650 (9)
O30.5499 (3)0.0723 (5)0.3498 (2)0.0833 (11)
O40.6896 (3)0.2426 (3)0.36472 (17)0.0570 (8)
O50.7255 (4)0.4574 (4)0.2203 (2)0.0873 (12)
O60.7291 (3)0.2142 (3)0.22473 (15)0.0532 (7)
O71.0122 (3)0.1240 (4)0.34194 (17)0.0668 (9)
O80.9724 (3)0.2386 (3)0.23545 (16)0.0564 (8)
O91.2187 (3)0.2686 (4)0.28619 (19)0.0749 (10)
O100.9277 (3)0.0843 (5)0.10753 (18)0.0738 (10)
N11.0553 (3)0.1711 (4)0.20799 (18)0.0505 (9)
C20.8407 (6)0.0501 (10)0.5213 (3)0.098 (2)
C30.5069 (4)0.3108 (7)0.3831 (3)0.0703 (15)
H3A0.42960.27250.37980.105*
H3B0.50180.38990.35070.105*
H3C0.54020.34470.43020.105*
C40.5824 (4)0.1965 (6)0.3658 (3)0.0603 (12)
C50.6116 (6)0.3217 (9)0.1216 (3)0.097 (2)
H5A0.54180.27250.12620.146*
H5B0.64990.26500.09280.146*
H5C0.59060.41460.09990.146*
C60.6941 (4)0.3424 (6)0.1934 (3)0.0607 (12)
C70.8168 (4)0.2182 (5)0.2902 (2)0.0500 (10)
H7A0.83510.31920.30410.060*
C80.9257 (4)0.1452 (5)0.2785 (2)0.0501 (10)
H8A0.90450.05200.25460.060*
C90.9693 (4)0.0343 (7)0.3882 (3)0.0712 (15)
H9A1.03260.01220.42920.085*
H9B0.94090.05610.36480.085*
C100.8700 (4)0.1095 (6)0.4110 (2)0.0560 (12)
H10A0.89860.19930.43630.067*
C110.7720 (4)0.1427 (5)0.3462 (2)0.0491 (10)
H11A0.73140.05300.32730.059*
C121.0261 (4)0.1045 (6)0.1424 (2)0.0562 (12)
C131.1421 (4)0.0666 (5)0.1293 (2)0.0569 (12)
C141.1708 (5)0.0142 (6)0.0768 (3)0.0657 (14)
H141.11250.05630.04120.079*
C151.2878 (6)0.0308 (7)0.0784 (4)0.0845 (17)
H151.30870.08420.04320.101*
C161.3747 (5)0.0298 (7)0.1309 (3)0.0835 (17)
H161.45330.01960.13020.100*
C171.3452 (5)0.1074 (6)0.1859 (3)0.0793 (16)
H171.40320.14630.22260.095*
C181.2312 (4)0.1231 (5)0.1834 (2)0.0529 (11)
C191.1734 (4)0.1982 (6)0.2336 (2)0.0564 (11)
O110.4128 (4)0.7342 (6)0.4406 (2)0.0991 (14)
O120.3423 (3)0.8357 (4)0.33808 (15)0.0564 (8)
O130.0676 (3)0.8442 (5)0.2317 (3)0.0949 (14)
O140.1691 (3)0.6402 (4)0.26372 (16)0.0538 (8)
O150.7126 (3)0.7988 (4)0.29705 (18)0.0669 (9)
O160.5774 (2)0.6731 (4)0.33357 (16)0.0566 (8)
O170.4092 (3)0.5377 (3)0.19975 (17)0.0581 (8)
O180.2382 (3)0.6188 (3)0.12131 (16)0.0591 (8)
O190.0646 (3)0.4089 (4)0.07830 (19)0.0710 (10)
O200.3982 (3)0.5904 (5)0.03530 (19)0.0799 (11)
N20.2382 (4)0.5133 (5)0.0720 (2)0.0599 (10)
C200.3261 (6)0.9705 (9)0.4350 (3)0.104 (2)
H20A0.34650.96420.48540.156*
H20B0.24270.98450.41800.156*
H20C0.36691.05070.42070.156*
C210.3611 (5)0.8328 (8)0.4048 (3)0.0790 (16)
C220.0176 (4)0.6513 (7)0.2828 (3)0.0678 (14)
H22A0.01120.63840.33270.102*
H22B0.03510.55850.26060.102*
H22C0.08770.70940.27320.102*
C230.0733 (4)0.7248 (6)0.2550 (2)0.0569 (12)
C240.7675 (5)0.6422 (8)0.3972 (3)0.0842 (17)
H24A0.76570.53960.38910.126*
H24B0.74340.66200.43960.126*
H24C0.84620.67770.40210.126*
C250.6864 (4)0.7153 (6)0.3371 (2)0.059
C260.4855 (4)0.7379 (5)0.2796 (2)0.0525 (11)
H26A0.49950.84220.27700.063*
C270.3697 (3)0.7111 (5)0.3015 (2)0.0496 (10)
H27A0.37840.62600.33230.060*
C280.2668 (4)0.6885 (5)0.2378 (2)0.0473 (10)
H28A0.24730.77890.21120.057*
C290.2899 (4)0.5686 (5)0.1910 (2)0.0517 (11)
H29A0.24900.48060.19980.062*
C300.4795 (4)0.6667 (6)0.2084 (2)0.0614 (13)
H30A0.44580.73440.17090.074*
H30B0.55850.64280.20510.074*
C310.1439 (4)0.4156 (5)0.0513 (2)0.0523 (11)
C320.1726 (4)0.3348 (5)0.0062 (2)0.0517 (11)
C330.1103 (5)0.2213 (6)0.0463 (2)0.0698 (14)
H330.03990.18750.03870.084*
C340.1565 (6)0.1625 (7)0.0968 (3)0.0941 (19)
H340.11930.08480.12350.113*
C350.2655 (7)0.2222 (10)0.1092 (4)0.125 (3)
H350.29410.18590.14590.149*
C360.3239 (6)0.3267 (8)0.0691 (4)0.097 (2)
H360.39560.35990.07520.117*
C370.2751 (4)0.3856 (6)0.0175 (2)0.0610 (13)
C380.3176 (4)0.5078 (6)0.0295 (2)0.0577 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.140 (6)0.152 (8)0.090 (5)0.014 (6)0.062 (4)0.032 (5)
O10.155 (5)0.141 (5)0.104 (3)0.035 (4)0.029 (3)0.008 (4)
O20.082 (2)0.069 (2)0.0509 (19)0.0061 (19)0.0297 (16)0.0099 (17)
O30.073 (2)0.068 (3)0.115 (3)0.013 (2)0.034 (2)0.020 (2)
O40.0583 (18)0.0449 (18)0.0749 (19)0.0017 (15)0.0299 (15)0.0017 (16)
O50.095 (3)0.043 (2)0.111 (3)0.002 (2)0.001 (2)0.015 (2)
O60.0639 (18)0.0388 (17)0.0554 (17)0.0029 (15)0.0120 (14)0.0043 (15)
O70.0572 (18)0.070 (2)0.076 (2)0.0014 (18)0.0216 (16)0.017 (2)
O80.0640 (18)0.0413 (17)0.0710 (19)0.0000 (15)0.0302 (16)0.0071 (16)
O90.073 (2)0.073 (3)0.078 (2)0.014 (2)0.0159 (18)0.028 (2)
O100.062 (2)0.083 (3)0.070 (2)0.003 (2)0.0042 (18)0.005 (2)
N10.052 (2)0.052 (2)0.053 (2)0.0043 (18)0.0235 (16)0.0007 (18)
C20.095 (4)0.144 (7)0.057 (3)0.037 (5)0.022 (3)0.008 (4)
C30.063 (3)0.076 (4)0.073 (3)0.002 (3)0.018 (3)0.007 (3)
C40.056 (3)0.055 (3)0.071 (3)0.006 (2)0.019 (2)0.007 (3)
C50.093 (4)0.105 (5)0.084 (4)0.001 (4)0.002 (3)0.024 (4)
C60.063 (3)0.056 (3)0.062 (3)0.008 (3)0.013 (2)0.006 (3)
C70.065 (3)0.031 (2)0.055 (2)0.006 (2)0.016 (2)0.003 (2)
C80.053 (2)0.042 (2)0.057 (2)0.000 (2)0.016 (2)0.006 (2)
C90.066 (3)0.082 (4)0.070 (3)0.020 (3)0.026 (3)0.030 (3)
C100.061 (3)0.059 (3)0.049 (2)0.006 (2)0.016 (2)0.000 (2)
C110.052 (2)0.041 (2)0.055 (2)0.000 (2)0.015 (2)0.004 (2)
C120.065 (3)0.059 (3)0.048 (2)0.012 (2)0.020 (2)0.006 (2)
C130.070 (3)0.042 (3)0.062 (3)0.000 (2)0.024 (2)0.007 (2)
C140.094 (4)0.047 (3)0.057 (3)0.001 (3)0.021 (3)0.002 (2)
C150.114 (5)0.055 (3)0.098 (4)0.016 (3)0.053 (4)0.006 (3)
C160.077 (3)0.078 (4)0.105 (4)0.008 (3)0.039 (3)0.002 (4)
C170.076 (4)0.062 (4)0.104 (4)0.007 (3)0.029 (3)0.001 (3)
C180.062 (3)0.049 (3)0.049 (2)0.002 (2)0.018 (2)0.011 (2)
C190.063 (3)0.047 (3)0.060 (3)0.002 (2)0.018 (2)0.003 (2)
O110.124 (3)0.108 (4)0.066 (2)0.033 (3)0.025 (2)0.002 (3)
O120.0646 (18)0.0526 (19)0.0551 (19)0.0081 (16)0.0207 (15)0.0096 (16)
O130.072 (2)0.061 (3)0.159 (4)0.024 (2)0.042 (3)0.039 (3)
O140.0517 (17)0.0447 (17)0.0716 (19)0.0041 (15)0.0278 (15)0.0066 (16)
O150.066 (2)0.052 (2)0.089 (2)0.0079 (17)0.0298 (18)0.0012 (19)
O160.0430 (16)0.056 (2)0.074 (2)0.0074 (15)0.0196 (15)0.0050 (17)
O170.0638 (19)0.0404 (18)0.076 (2)0.0079 (15)0.0285 (16)0.0060 (16)
O180.078 (2)0.0381 (17)0.0626 (19)0.0034 (16)0.0193 (16)0.0046 (16)
O190.065 (2)0.067 (2)0.088 (2)0.0089 (18)0.0313 (19)0.001 (2)
O200.084 (2)0.080 (3)0.087 (2)0.024 (2)0.043 (2)0.014 (2)
N20.071 (3)0.052 (2)0.059 (2)0.008 (2)0.022 (2)0.015 (2)
C200.110 (5)0.128 (6)0.077 (4)0.025 (5)0.028 (4)0.047 (4)
C210.088 (4)0.086 (4)0.064 (4)0.010 (4)0.023 (3)0.007 (4)
C220.048 (2)0.092 (4)0.071 (3)0.002 (3)0.029 (2)0.008 (3)
C230.054 (3)0.061 (3)0.056 (3)0.003 (3)0.014 (2)0.002 (3)
C240.072 (3)0.099 (5)0.080 (3)0.015 (4)0.017 (3)0.012 (4)
C250.0590.0590.0590.0000.0150.000
C260.057 (2)0.039 (2)0.071 (3)0.004 (2)0.032 (2)0.002 (2)
C270.053 (2)0.040 (2)0.064 (3)0.001 (2)0.028 (2)0.002 (2)
C280.058 (2)0.035 (2)0.054 (2)0.003 (2)0.024 (2)0.0039 (19)
C290.061 (3)0.033 (2)0.065 (3)0.007 (2)0.024 (2)0.005 (2)
C300.062 (3)0.064 (3)0.071 (3)0.007 (3)0.040 (2)0.003 (3)
C310.052 (2)0.049 (3)0.058 (3)0.003 (2)0.018 (2)0.001 (2)
C320.064 (3)0.049 (3)0.045 (2)0.005 (2)0.018 (2)0.002 (2)
C330.098 (4)0.048 (3)0.059 (3)0.003 (3)0.010 (3)0.002 (3)
C340.140 (5)0.063 (4)0.074 (4)0.005 (4)0.015 (4)0.023 (3)
C350.166 (7)0.119 (7)0.107 (5)0.018 (6)0.068 (5)0.046 (5)
C360.121 (5)0.083 (5)0.110 (5)0.007 (4)0.072 (4)0.017 (4)
C370.064 (3)0.066 (3)0.057 (3)0.007 (3)0.022 (2)0.005 (3)
C380.057 (3)0.061 (3)0.059 (3)0.001 (3)0.022 (2)0.000 (3)
Geometric parameters (Å, º) top
C1—C21.497 (10)O11—C211.214 (7)
C1—H1A0.9600O12—C211.272 (6)
C1—H1B0.9600O12—C271.433 (5)
C1—H1C0.9600O13—C231.188 (6)
O1—C21.292 (10)O14—C231.343 (6)
O2—C21.307 (7)O14—C281.435 (5)
O2—C101.421 (5)O15—C251.194 (6)
O3—C41.224 (6)O16—C251.321 (6)
O4—C41.332 (6)O16—C261.437 (5)
O4—C111.446 (5)O17—C291.395 (5)
O5—C61.201 (6)O17—C301.433 (6)
O6—C61.349 (6)O18—N21.373 (5)
O6—C71.430 (5)O18—C291.426 (5)
O7—C81.408 (5)O19—C311.180 (5)
O7—C91.410 (6)O20—C381.198 (6)
O8—N11.373 (4)N2—C381.397 (6)
O8—C81.410 (5)N2—C311.405 (6)
O9—C191.222 (6)C20—C211.501 (9)
O10—C121.199 (5)C20—H20A0.9600
N1—C191.372 (6)C20—H20B0.9600
N1—C121.388 (6)C20—H20C0.9600
C3—C41.471 (7)C22—C231.477 (7)
C3—H3A0.9600C22—H22A0.9600
C3—H3B0.9600C22—H22B0.9600
C3—H3C0.9600C22—H22C0.9600
C5—C61.508 (8)C24—C251.479 (8)
C5—H5A0.9600C24—H24A0.9600
C5—H5B0.9600C24—H24B0.9600
C5—H5C0.9600C24—H24C0.9600
C7—C111.502 (6)C26—C301.530 (7)
C7—C81.511 (6)C26—C271.542 (5)
C7—H7A0.9800C26—H26A0.9800
C8—H8A0.9800C27—C281.517 (6)
C9—C101.516 (6)C27—H27A0.9800
C9—H9A0.9700C28—C291.506 (6)
C9—H9B0.9700C28—H28A0.9800
C10—C111.516 (6)C29—H29A0.9800
C10—H10A0.9800C30—H30A0.9700
C11—H11A0.9800C30—H30B0.9700
C12—C131.488 (7)C31—C321.461 (6)
C13—C141.381 (7)C32—C371.359 (6)
C13—C181.390 (6)C32—C331.401 (6)
C14—C151.372 (8)C33—C341.355 (8)
C14—H140.9300C33—H330.9300
C15—C161.373 (9)C34—C351.466 (5)
C15—H150.9300C34—H340.9300
C16—C171.407 (8)C35—C361.321 (9)
C16—H160.9300C35—H350.9300
C17—C181.334 (7)C36—C371.392 (7)
C17—H170.9300C36—H360.9300
C18—C191.497 (7)C37—C381.463 (7)
C2—C1—H1A109.5C21—O12—C27119.7 (4)
C2—C1—H1B109.5C23—O14—C28119.4 (4)
H1A—C1—H1B109.5C25—O16—C26116.9 (4)
C2—C1—H1C109.5C29—O17—C30111.9 (3)
H1A—C1—H1C109.5N2—O18—C29111.7 (3)
H1B—C1—H1C109.5O18—N2—C38124.3 (4)
C2—O2—C10118.0 (5)O18—N2—C31121.3 (4)
C4—O4—C11119.5 (4)C38—N2—C31113.5 (4)
C6—O6—C7117.1 (4)C21—C20—H20A109.5
C8—O7—C9110.9 (3)C21—C20—H20B109.5
N1—O8—C8112.1 (3)H20A—C20—H20B109.5
C19—N1—O8121.5 (4)C21—C20—H20C109.5
C19—N1—C12114.3 (4)H20A—C20—H20C109.5
O8—N1—C12122.0 (4)H20B—C20—H20C109.5
O1—C2—O2119.3 (6)O11—C21—O12122.9 (6)
O1—C2—C1130.3 (6)O11—C21—C20123.5 (6)
O2—C2—C1110.3 (7)O12—C21—C20113.2 (6)
C4—C3—H3A109.5C23—C22—H22A109.5
C4—C3—H3B109.5C23—C22—H22B109.5
H3A—C3—H3B109.5H22A—C22—H22B109.5
C4—C3—H3C109.5C23—C22—H22C109.5
H3A—C3—H3C109.5H22A—C22—H22C109.5
H3B—C3—H3C109.5H22B—C22—H22C109.5
O3—C4—O4122.0 (5)O13—C23—O14123.5 (5)
O3—C4—C3124.3 (5)O13—C23—C22126.3 (5)
O4—C4—C3113.6 (5)O14—C23—C22110.1 (5)
C6—C5—H5A109.5C25—C24—H24A109.5
C6—C5—H5B109.5C25—C24—H24B109.5
H5A—C5—H5B109.5H24A—C24—H24B109.5
C6—C5—H5C109.5C25—C24—H24C109.5
H5A—C5—H5C109.5H24A—C24—H24C109.5
H5B—C5—H5C109.5H24B—C24—H24C109.5
O5—C6—O6123.3 (4)O15—C25—O16124.1 (4)
O5—C6—C5125.2 (5)O15—C25—C24126.8 (5)
O6—C6—C5111.4 (5)O16—C25—C24109.1 (4)
O6—C7—C11109.9 (3)O16—C26—C30110.4 (4)
O6—C7—C8107.2 (3)O16—C26—C27106.2 (3)
C11—C7—C8111.6 (4)C30—C26—C27110.1 (4)
O6—C7—H7A109.4O16—C26—H26A110.1
C11—C7—H7A109.4C30—C26—H26A110.1
C8—C7—H7A109.4C27—C26—H26A110.1
O7—C8—O8108.2 (3)O12—C27—C28106.9 (3)
O7—C8—C7112.1 (3)O12—C27—C26109.5 (4)
O8—C8—C7106.7 (3)C28—C27—C26111.5 (3)
O7—C8—H8A109.9O12—C27—H27A109.6
O8—C8—H8A109.9C28—C27—H27A109.6
C7—C8—H8A109.9C26—C27—H27A109.6
O7—C9—C10110.2 (4)O14—C28—C29105.6 (3)
O7—C9—H9A109.6O14—C28—C27107.0 (3)
C10—C9—H9A109.6C29—C28—C27112.1 (4)
O7—C9—H9B109.6O14—C28—H28A110.7
C10—C9—H9B109.6C29—C28—H28A110.7
H9A—C9—H9B108.1C27—C28—H28A110.7
O2—C10—C11108.2 (4)O17—C29—O18110.9 (3)
O2—C10—C9109.4 (4)O17—C29—C28113.8 (4)
C11—C10—C9108.7 (4)O18—C29—C28104.3 (4)
O2—C10—H10A110.2O17—C29—H29A109.2
C11—C10—H10A110.2O18—C29—H29A109.2
C9—C10—H10A110.2C28—C29—H29A109.2
O4—C11—C7105.4 (4)O17—C30—C26111.0 (3)
O4—C11—C10109.3 (3)O17—C30—H30A109.4
C7—C11—C10112.2 (4)C26—C30—H30A109.4
O4—C11—H11A109.9O17—C30—H30B109.4
C7—C11—H11A109.9C26—C30—H30B109.4
C10—C11—H11A109.9H30A—C30—H30B108.0
O10—C12—N1125.2 (4)O19—C31—N2123.8 (5)
O10—C12—C13130.9 (4)O19—C31—C32132.8 (5)
N1—C12—C13103.9 (4)N2—C31—C32103.4 (4)
C14—C13—C18119.7 (5)C37—C32—C33121.6 (4)
C14—C13—C12131.3 (5)C37—C32—C31109.6 (4)
C18—C13—C12108.9 (4)C33—C32—C31128.9 (4)
C15—C14—C13118.1 (5)C34—C33—C32117.6 (5)
C15—C14—H14120.9C34—C33—H33121.2
C13—C14—H14120.9C32—C33—H33121.2
C14—C15—C16121.4 (5)C33—C34—C35119.6 (5)
C14—C15—H15119.3C33—C34—H34120.2
C16—C15—H15119.3C35—C34—H34120.2
C15—C16—C17120.2 (5)C36—C35—C34121.3 (6)
C15—C16—H16119.9C36—C35—H35119.4
C17—C16—H16119.9C34—C35—H35119.4
C18—C17—C16117.7 (6)C35—C36—C37118.1 (6)
C18—C17—H17121.2C35—C36—H36120.9
C16—C17—H17121.2C37—C36—H36120.9
C17—C18—C13122.7 (5)C32—C37—C36121.7 (5)
C17—C18—C19129.9 (5)C32—C37—C38109.7 (4)
C13—C18—C19107.4 (4)C36—C37—C38128.5 (5)
O9—C19—N1126.2 (4)O20—C38—N2123.3 (5)
O9—C19—C18129.0 (4)O20—C38—C37133.3 (4)
N1—C19—C18104.8 (4)N2—C38—C37103.4 (4)
C8—O8—N1—C19104.9 (4)C29—O18—N2—C38102.4 (5)
C8—O8—N1—C1293.0 (4)C29—O18—N2—C3189.3 (5)
C10—O2—C2—O10.8 (9)C27—O12—C21—O117.8 (9)
C10—O2—C2—C1179.9 (5)C27—O12—C21—C20179.1 (5)
C11—O4—C4—O31.9 (7)C28—O14—C23—O136.3 (7)
C11—O4—C4—C3178.0 (4)C28—O14—C23—C22177.7 (4)
C7—O6—C6—O56.3 (7)C26—O16—C25—O152.8 (7)
C7—O6—C6—C5173.9 (4)C26—O16—C25—C24177.5 (4)
C6—O6—C7—C11123.6 (4)C25—O16—C26—C3078.9 (5)
C6—O6—C7—C8114.9 (4)C25—O16—C26—C27161.8 (4)
C9—O7—C8—O8178.3 (4)C21—O12—C27—C28135.9 (5)
C9—O7—C8—C760.9 (5)C21—O12—C27—C26103.2 (5)
N1—O8—C8—O773.0 (4)O16—C26—C27—O1295.9 (4)
N1—O8—C8—C7166.2 (3)C30—C26—C27—O12144.7 (4)
O6—C7—C8—O7171.4 (3)O16—C26—C27—C28146.0 (4)
C11—C7—C8—O751.0 (5)C30—C26—C27—C2826.6 (5)
O6—C7—C8—O870.3 (4)C23—O14—C28—C29125.7 (4)
C11—C7—C8—O8169.3 (3)C23—O14—C28—C27114.7 (4)
C8—O7—C9—C1065.7 (5)O12—C27—C28—O1470.1 (4)
C2—O2—C10—C11129.1 (5)C26—C27—C28—O14170.2 (4)
C2—O2—C10—C9112.6 (6)O12—C27—C28—C29174.6 (3)
O7—C9—C10—O2177.4 (4)C26—C27—C28—C2954.9 (5)
O7—C9—C10—C1159.4 (6)C30—O17—C29—O1876.9 (4)
C4—O4—C11—C7129.4 (4)C30—O17—C29—C2840.3 (5)
C4—O4—C11—C10109.8 (5)N2—O18—C29—O1765.0 (4)
O6—C7—C11—O475.7 (4)N2—O18—C29—C28172.1 (3)
C8—C7—C11—O4165.5 (3)O14—C28—C29—O17137.4 (4)
O6—C7—C11—C10165.4 (4)C27—C28—C29—O1721.3 (5)
C8—C7—C11—C1046.6 (5)O14—C28—C29—O18101.6 (4)
O2—C10—C11—O474.4 (5)C27—C28—C29—O18142.3 (3)
C9—C10—C11—O4166.9 (4)C29—O17—C30—C2670.2 (5)
O2—C10—C11—C7169.0 (4)O16—C26—C30—O1784.7 (4)
C9—C10—C11—C750.3 (5)C27—C26—C30—O1732.2 (5)
C19—N1—C12—O10172.2 (5)O18—N2—C31—O196.6 (7)
O8—N1—C12—O108.9 (7)C38—N2—C31—O19176.1 (5)
C19—N1—C12—C138.5 (5)O18—N2—C31—C32174.0 (4)
O8—N1—C12—C13171.7 (4)C38—N2—C31—C324.4 (5)
O10—C12—C13—C146.9 (9)O19—C31—C32—C37179.7 (5)
N1—C12—C13—C14172.3 (5)N2—C31—C32—C370.9 (5)
O10—C12—C13—C18175.5 (5)O19—C31—C32—C330.3 (9)
N1—C12—C13—C185.2 (5)N2—C31—C32—C33179.0 (5)
C18—C13—C14—C152.7 (7)C37—C32—C33—C340.6 (7)
C12—C13—C14—C15179.9 (5)C31—C32—C33—C34179.4 (5)
C13—C14—C15—C160.6 (9)C32—C33—C34—C352.2 (9)
C14—C15—C16—C171.9 (10)C33—C34—C35—C364.2 (12)
C15—C16—C17—C182.1 (9)C34—C35—C36—C374.2 (12)
C16—C17—C18—C130.1 (8)C33—C32—C37—C360.6 (8)
C16—C17—C18—C19179.6 (5)C31—C32—C37—C36179.3 (5)
C14—C13—C18—C172.5 (8)C33—C32—C37—C38177.4 (4)
C12—C13—C18—C17179.6 (5)C31—C32—C37—C382.7 (6)
C14—C13—C18—C19177.2 (4)C35—C36—C37—C322.5 (10)
C12—C13—C18—C190.6 (5)C35—C36—C37—C38175.1 (6)
O8—N1—C19—O98.5 (7)O18—N2—C38—O204.7 (8)
C12—N1—C19—O9171.9 (5)C31—N2—C38—O20173.9 (5)
O8—N1—C19—C18171.5 (4)O18—N2—C38—C37175.1 (4)
C12—N1—C19—C188.2 (5)C31—N2—C38—C375.9 (5)
C17—C18—C19—O94.5 (9)C32—C37—C38—O20174.7 (6)
C13—C18—C19—O9175.8 (5)C36—C37—C38—O203.1 (10)
C17—C18—C19—N1175.5 (5)C32—C37—C38—N25.1 (5)
C13—C18—C19—N14.2 (5)C36—C37—C38—N2177.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O50.982.222.676 (6)107
C10—H10A···O10.982.142.609 (7)107
C11—H11A···O30.982.292.702 (6)104
C11—H11A···O15i0.982.423.339 (6)157
C22—H22A···O1ii0.962.393.329 (7)165
C26—H26A···O3iii0.982.543.385 (6)144
C27—H27A···O110.982.292.656 (6)101
C28—H28A···O130.982.322.718 (6)103
C30—H30B···O50.972.563.429 (6)149
C35—H35···O5iv0.932.543.294 (8)138
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+1; (iii) x, y+1, z; (iv) x+1, y1/2, z.

Experimental details

Crystal data
Chemical formulaC19H19NO10
Mr421.35
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)11.722 (2), 9.2270 (18), 19.615 (4)
β (°) 104.52 (3)
V3)2053.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.957, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
4180, 3977, 2784
Rint0.058
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.131, 1.00
No. of reflections3977
No. of parameters541
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.22

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O50.982.222.676 (6)107.2
C10—H10A···O10.982.142.609 (7)107.3
C11—H11A···O30.982.292.702 (6)104.4
C11—H11A···O15i0.982.423.339 (6)156.7
C22—H22A···O1ii0.962.393.329 (7)165.4
C26—H26A···O3iii0.982.543.385 (6)143.9
C27—H27A···O110.982.292.656 (6)100.9
C28—H28A···O130.982.322.718 (6)103.2
C30—H30B···O50.972.563.429 (6)149.2
C35—H35···O5iv0.932.543.294 (8)138.2
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+1; (iii) x, y+1, z; (iv) x+1, y1/2, z.
 

Acknowledgements

We are grateful to the National Natural Science Foundation of China (grant No. 30711041) and the Fundamental Research Funds for the Central Universities (grant No. 1106020824)

References

First citationBai, L., Wang, X. & Cai, B. (2008). Acta Cryst. E64, o1623.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds