1-Azido­ethoxy-2,3,4,6-tetra-O-acetyl-β-d-glucoside

Yang, X.-H.; Zhou, Y.-H.; Liu, H.-J.; Guo, X.-X.

doi:10.1107/S1600536809039737

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2651

https://doi.org/10.1107/S1600536809039737

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1-Azidoethoxy-2,3,4,6-tetra-O-acetyl-β-D-glucoside

Xiao-Hui Yang,^a Yong-Hong Zhou,^a ^* Hong-Jun Liu ^a and Xiao-Xin Guo ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, 210042, People's Republic of China
^*Correspondence e-mail: yhzhou1966@yahoo.com.cn

(Received 16 July 2009; accepted 30 September 2009; online 3 October 2009)

In the title compound, C₁₆H₂₃N₃O₁₀, the galactopyranoside ring adopts a chair conformation. All the non-H substituents are situated in equatorial positions. There are short intramolecular C—H⋯O contacts and an intermolecular C—H⋯O interaction in the structure.

Related literature

For renewable compounds generated by living organisms that can be turned into useful macromolecular materials, see: Gandini (2008 ). For industrial applications of lignin, see: Gandini & Belgacem (2002 ). For attempts to obtain new polyurethanes between lignin and saccharide, see: Hatakeyama & Hatakeyama (2005 ).

Experimental

Crystal data

C₁₆H₂₃N₃O₁₀
M_r = 417.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9730 (14) Å
b = 14.747 (3) Å
c = 19.916 (4) Å
V = 2048.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.967, T_max = 0.989
3276 measured reflections
2152 independent reflections
1428 reflections with I > 2σ(I)
R_int = 0.036
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.156
S = 1.06
2152 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O4	0.98	2.21	2.666 (6)	107
C15—H15A⋯O2	0.98	2.32	2.723 (6)	104
C16—H16A⋯O7	0.98	2.27	2.702 (6)	106
C16—H16A⋯O9	0.98	2.44	2.824 (5)	103
C9—H9B⋯O1ⁱ	0.96	2.48	3.402 (6)	160
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039737/fb2162sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039737/fb2162Isup2.hkl

checkCIF report

Comment top

The incessant biological activity in living organisms generates a multitude of compounds, including a variety of monomers and polymers such as saccharide, cellulose, hemicellulose, lignin and so on. More and more scientists are exclusively concerned with those renewable compounds that can be turned into useful macromolecular materials (Gandini, 2008). However, most of lignin as a by-product from the paper industry is being discharged into the environment. This causes serious environmental pollution. Also for this reason industrial applications of lignin have attracted a great deal of attention (Gandini & Belgacem, 2002).

In attempt to obtain new polyurethanes between lignin and saccharide (Hatakeyama & Hatakeyama, 2005) and to optimize their properties, the title structure, a new galactopyranoside, 2-azidoethoxy 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside, has been synthesized and its structure determined. The galactopyranoside ring adopts a chair conformation. There are present four intramolecular C-H···O interactionss (Tab. 1). Each of them forms four five-membered rings. In the crystal structure, the molecules are linked into chains along the a axis by C—H···O interactions (Fig. 2 and Tab. 1).

Related literature top

For renewable compounds that can be turned into useful macromolecular materials, see: Gandini (2008). For industrial applications of lignin, see: Gandini & Belgacem (2002). For attempts to obtain new polyurethanes between lignin and saccharide, see: Hatakeyama & Hatakeyama (2005).

Experimental top

β-D-glucose pentaacetate (5.0 g, 12.8 mmol) was dissolved in 25 ml of the anhydrous CH₂Cl₂. 2-azidoethanol (1.9 g, 22.3 mmol) was added to this solution by a syringe. The resulting solution was stirred under argon and cooled to 273 K. BF₃.Et₂O (2.1 ml, 16.7 mmol) was then added dropwise at 273 K. The mixture was stirred for 1 h at 273 K and then overnight at room temperature. The mixture was diluted with 50 ml CH₂Cl₂ and washed with cold water and with saturated aqueous NaHCO₃ at room temperature, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a fawn crude residue that was purified by column chromatography (hexane/EtOAc 2:1) and recrystallization from the solution of hexane/EtOAc (1:1) in order to obtain a pure solid of the title compound. Colourless single crystals suitable for X-ray crystallographic analysis were grown by slow evaporation from an ethyl acetate solution of the title compound.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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

	Fig. 1. The title molecule with the atom-labelling scheme. The displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the title molecules, viewed along the c axis.

1-Azidoethoxy-2,3,4,6-tetra-O-acetyl-β-D-glucoside top

Crystal data top

C₁₆H₂₃N₃O₁₀	F(000) = 880
M_r = 417.37	D_x = 1.354 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.9730 (14) Å	θ = 9–12°
b = 14.747 (3) Å	µ = 0.11 mm⁻¹
c = 19.916 (4) Å	T = 293 K
V = 2048.0 (7) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 25.3°, θ_min = 1.7°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
T_min = 0.967, T_max = 0.989	l = 0→23
3276 measured reflections	3 standard reflections every 200 reflections
2152 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: difference Fourier map
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0842P)² + 0.0427P] where P = (F_o² + 2F_c²)/3
2152 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³
88 constraints

Crystal data top

C₁₆H₂₃N₃O₁₀	V = 2048.0 (7) Å³
M_r = 417.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9730 (14) Å	µ = 0.11 mm⁻¹
b = 14.747 (3) Å	T = 293 K
c = 19.916 (4) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1428 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.036
T_min = 0.967, T_max = 0.989	3 standard reflections every 200 reflections
3276 measured reflections	intensity decay: 1%
2152 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
2152 reflections	Δρ_min = −0.20 e Å⁻³
266 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

	x	y	z	U_iso*/U_eq
O1	0.7582 (5)	0.6069 (2)	0.05712 (18)	0.0722 (10)
N1	1.0447 (9)	0.6905 (4)	0.1458 (3)	0.0961 (17)
N2	1.0080 (9)	0.6436 (4)	0.1911 (4)	0.0987 (18)
N3	0.9676 (16)	0.6099 (5)	0.2393 (4)	0.167 (3)
O2	0.3076 (8)	0.2527 (2)	0.0360 (2)	0.1001 (14)
C1	1.0868 (10)	0.6426 (5)	0.0830 (3)	0.103 (2)
H1B	1.1128	0.5794	0.0929	0.123*
H1C	1.2014	0.6684	0.0630	0.123*
O3	0.2457 (5)	0.40003 (19)	0.05186 (15)	0.0560 (8)
C2	0.9245 (9)	0.6483 (5)	0.0333 (3)	0.0917 (19)
H2A	0.8978	0.7115	0.0237	0.110*
H2B	0.9631	0.6193	−0.0083	0.110*
O4	0.4451 (8)	0.5373 (3)	0.18472 (18)	0.0927 (13)
C3	0.0437 (9)	0.2978 (4)	0.1058 (3)	0.0820 (17)
H3A	0.0147	0.2344	0.1099	0.123*
H3B	−0.0647	0.3290	0.0872	0.123*
H3C	0.0724	0.3223	0.1493	0.123*
O5	0.6040 (5)	0.4482 (2)	0.11247 (15)	0.0626 (9)
C4	0.2113 (9)	0.3097 (3)	0.0612 (2)	0.0647 (13)
O6	0.2735 (5)	0.40451 (19)	−0.09523 (15)	0.0554 (8)
C5	0.6697 (10)	0.4265 (4)	0.2258 (3)	0.0854 (18)
H5A	0.6339	0.4465	0.2700	0.128*
H5B	0.8048	0.4357	0.2195	0.128*
H5C	0.6403	0.3633	0.2210	0.128*
O7	−0.0125 (5)	0.4706 (3)	−0.1036 (2)	0.0817 (11)
C6	0.5624 (9)	0.4791 (3)	0.1751 (3)	0.0636 (13)
O8	0.2457 (7)	0.6740 (3)	−0.23285 (18)	0.0903 (13)
C7	0.0537 (10)	0.3357 (4)	−0.1658 (3)	0.0838 (18)
H7A	−0.0777	0.3390	−0.1799	0.126*
H7B	0.0760	0.2789	−0.1436	0.126*
H7C	0.1360	0.3404	−0.2043	0.126*
O9	0.2845 (5)	0.63294 (19)	−0.12588 (15)	0.0557 (8)
C8	0.0953 (7)	0.4111 (3)	−0.1188 (2)	0.0541 (11)
O10	0.5898 (5)	0.5863 (2)	−0.03885 (16)	0.0603 (8)
C9	0.0336 (9)	0.7316 (3)	−0.1504 (3)	0.0789 (17)
H9A	−0.0210	0.7666	−0.1863	0.118*
H9B	0.0762	0.7716	−0.1154	0.118*
H9C	−0.0614	0.6909	−0.1329	0.118*
C10	0.1978 (8)	0.6792 (3)	−0.1759 (3)	0.0626 (13)
C11	0.4448 (8)	0.5767 (3)	−0.1452 (2)	0.0636 (13)
H11A	0.5502	0.6141	−0.1608	0.076*
H11B	0.4076	0.5362	−0.1813	0.076*
C12	0.5050 (7)	0.5231 (3)	−0.0851 (2)	0.0525 (11)
H12A	0.6027	0.4791	−0.0987	0.063*
C13	0.6755 (7)	0.5413 (3)	0.0177 (2)	0.0570 (12)
H13A	0.7714	0.4970	0.0028	0.068*
C14	0.5181 (7)	0.4956 (3)	0.0570 (2)	0.0520 (11)
H14A	0.4290	0.5415	0.0740	0.062*
C15	0.4101 (7)	0.4284 (3)	0.0141 (2)	0.0509 (11)
H15A	0.4918	0.3761	0.0039	0.061*
C16	0.3439 (6)	0.4733 (3)	−0.0504 (2)	0.0492 (11)
H16A	0.2403	0.5161	−0.0403	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.061 (2)	0.093 (2)	0.063 (2)	−0.014 (2)	0.0038 (19)	−0.021 (2)
N1	0.115 (4)	0.086 (3)	0.087 (4)	−0.004 (4)	−0.025 (4)	−0.003 (3)
N2	0.098 (4)	0.085 (4)	0.114 (5)	−0.005 (3)	−0.024 (4)	0.023 (3)
N3	0.200 (9)	0.142 (6)	0.158 (7)	0.013 (7)	−0.005 (8)	0.058 (6)
O2	0.148 (4)	0.0562 (19)	0.097 (3)	0.010 (3)	0.026 (3)	0.005 (2)
C1	0.064 (4)	0.126 (5)	0.117 (6)	−0.009 (4)	0.006 (4)	−0.040 (5)
O3	0.0622 (18)	0.0532 (16)	0.0526 (18)	0.0000 (16)	0.0079 (16)	−0.0005 (15)
C2	0.071 (4)	0.127 (5)	0.077 (4)	−0.024 (4)	0.013 (4)	0.001 (4)
O4	0.136 (4)	0.092 (3)	0.050 (2)	0.034 (3)	0.001 (2)	−0.016 (2)
C3	0.088 (4)	0.092 (4)	0.066 (4)	−0.022 (3)	−0.001 (3)	0.003 (3)
O5	0.073 (2)	0.075 (2)	0.0399 (17)	0.0134 (19)	−0.0103 (18)	−0.0057 (15)
C4	0.093 (4)	0.054 (3)	0.047 (3)	−0.005 (3)	−0.004 (3)	0.006 (2)
O6	0.065 (2)	0.0550 (16)	0.0466 (17)	0.0097 (16)	−0.0055 (17)	−0.0104 (15)
C5	0.109 (5)	0.097 (4)	0.050 (3)	0.000 (4)	−0.011 (3)	0.006 (3)
O7	0.062 (2)	0.098 (3)	0.085 (3)	0.011 (2)	−0.016 (2)	−0.014 (2)
C6	0.077 (3)	0.064 (3)	0.049 (3)	−0.002 (3)	−0.011 (3)	−0.008 (3)
O8	0.107 (3)	0.118 (3)	0.046 (2)	0.020 (3)	0.003 (2)	0.012 (2)
C7	0.106 (5)	0.090 (4)	0.055 (3)	−0.018 (4)	−0.007 (3)	−0.013 (3)
O9	0.062 (2)	0.0580 (16)	0.0475 (17)	0.0098 (16)	0.0027 (16)	0.0056 (15)
C8	0.053 (3)	0.066 (3)	0.044 (3)	0.002 (3)	0.000 (2)	−0.002 (2)
O10	0.0659 (19)	0.0599 (17)	0.0551 (19)	0.0019 (17)	−0.0010 (18)	0.0001 (16)
C9	0.094 (4)	0.072 (3)	0.071 (4)	0.018 (3)	−0.011 (3)	0.004 (3)
C10	0.074 (3)	0.059 (3)	0.054 (3)	−0.004 (3)	−0.012 (3)	0.003 (3)
C11	0.072 (3)	0.069 (3)	0.051 (3)	0.002 (3)	0.014 (3)	0.001 (2)
C12	0.057 (3)	0.053 (2)	0.048 (3)	0.006 (2)	0.002 (2)	−0.007 (2)
C13	0.053 (3)	0.065 (3)	0.054 (3)	0.003 (2)	−0.006 (2)	−0.009 (2)
C14	0.055 (3)	0.063 (3)	0.039 (2)	0.008 (2)	0.000 (2)	−0.002 (2)
C15	0.052 (3)	0.055 (2)	0.046 (2)	0.011 (2)	−0.005 (2)	−0.006 (2)
C16	0.053 (2)	0.051 (2)	0.043 (3)	0.012 (2)	−0.004 (2)	−0.010 (2)

Geometric parameters (Å, º) top

O1—C13	1.373 (5)	O7—C8	1.194 (5)
O1—C2	1.394 (7)	O8—C10	1.184 (6)
N1—N2	1.165 (7)	C7—C8	1.482 (6)
N1—C1	1.467 (7)	C7—H7A	0.9600
N2—N3	1.117 (9)	C7—H7B	0.9600
O2—C4	1.188 (6)	C7—H7C	0.9600
C1—C2	1.505 (9)	O9—C10	1.351 (6)
C1—H1B	0.9700	O9—C11	1.445 (6)
C1—H1C	0.9700	O10—C12	1.437 (5)
O3—C4	1.366 (5)	O10—C13	1.437 (5)
O3—C15	1.433 (5)	C9—C10	1.472 (7)
C2—H2A	0.9700	C9—H9A	0.9600
C2—H2B	0.9700	C9—H9B	0.9600
O4—C6	1.201 (6)	C9—H9C	0.9600
C3—C4	1.478 (8)	C11—C12	1.495 (6)
C3—H3A	0.9600	C11—H11A	0.9700
C3—H3B	0.9600	C11—H11B	0.9700
C3—H3C	0.9600	C12—C16	1.509 (6)
O5—C6	1.360 (6)	C12—H12A	0.9800
O5—C14	1.439 (5)	C13—C14	1.507 (7)
O6—C8	1.332 (6)	C13—H13A	0.9800
O6—C16	1.437 (5)	C14—C15	1.509 (6)
C5—C6	1.476 (8)	C14—H14A	0.9800
C5—H5A	0.9600	C15—C16	1.518 (6)
C5—H5B	0.9600	C15—H15A	0.9800
C5—H5C	0.9600	C16—H16A	0.9800

C13—O1—C2	117.6 (4)	C12—O10—C13	111.9 (3)
N2—N1—C1	114.7 (6)	C10—C9—H9A	109.5
N3—N2—N1	170.0 (9)	C10—C9—H9B	109.5
N1—C1—C2	112.5 (6)	H9A—C9—H9B	109.5
N1—C1—H1B	109.1	C10—C9—H9C	109.5
C2—C1—H1B	109.1	H9A—C9—H9C	109.5
N1—C1—H1C	109.1	H9B—C9—H9C	109.5
C2—C1—H1C	109.1	O8—C10—O9	123.2 (5)
H1B—C1—H1C	107.8	O8—C10—C9	125.8 (5)
C4—O3—C15	119.8 (4)	O9—C10—C9	111.0 (4)
O1—C2—C1	112.2 (5)	O9—C11—C12	107.9 (4)
O1—C2—H2A	109.2	O9—C11—H11A	110.1
C1—C2—H2A	109.2	C12—C11—H11A	110.1
O1—C2—H2B	109.2	O9—C11—H11B	110.1
C1—C2—H2B	109.2	C12—C11—H11B	110.1
H2A—C2—H2B	107.9	H11A—C11—H11B	108.4
C4—C3—H3A	109.5	O10—C12—C11	106.6 (3)
C4—C3—H3B	109.5	O10—C12—C16	109.2 (4)
H3A—C3—H3B	109.5	C11—C12—C16	114.5 (4)
C4—C3—H3C	109.5	O10—C12—H12A	108.8
H3A—C3—H3C	109.5	C11—C12—H12A	108.8
H3B—C3—H3C	109.5	C16—C12—H12A	108.8
C6—O5—C14	117.0 (4)	O1—C13—O10	107.3 (4)
O2—C4—O3	122.3 (5)	O1—C13—C14	108.9 (4)
O2—C4—C3	128.1 (5)	O10—C13—C14	108.1 (4)
O3—C4—C3	109.7 (5)	O1—C13—H13A	110.8
C8—O6—C16	119.1 (4)	O10—C13—H13A	110.8
C6—C5—H5A	109.5	C14—C13—H13A	110.8
C6—C5—H5B	109.5	O5—C14—C13	108.2 (4)
H5A—C5—H5B	109.5	O5—C14—C15	108.9 (3)
C6—C5—H5C	109.5	C13—C14—C15	111.3 (4)
H5A—C5—H5C	109.5	O5—C14—H14A	109.5
H5B—C5—H5C	109.5	C13—C14—H14A	109.5
O4—C6—O5	122.0 (5)	C15—C14—H14A	109.5
O4—C6—C5	127.7 (5)	O3—C15—C14	107.1 (3)
O5—C6—C5	110.1 (5)	O3—C15—C16	109.2 (4)
C8—C7—H7A	109.5	C14—C15—C16	110.1 (3)
C8—C7—H7B	109.5	O3—C15—H15A	110.1
H7A—C7—H7B	109.5	C14—C15—H15A	110.1
C8—C7—H7C	109.5	C16—C15—H15A	110.1
H7A—C7—H7C	109.5	O6—C16—C12	108.3 (3)
H7B—C7—H7C	109.5	O6—C16—C15	108.8 (3)
C10—O9—C11	116.1 (4)	C12—C16—C15	111.9 (4)
O7—C8—O6	123.5 (4)	O6—C16—H16A	109.3
O7—C8—C7	126.0 (5)	C12—C16—H16A	109.3
O6—C8—C7	110.5 (5)	C15—C16—H16A	109.3

C1—N1—N2—N3	−175 (5)	C6—O5—C14—C15	−125.1 (4)
N2—N1—C1—C2	104.9 (7)	O1—C13—C14—O5	−65.4 (5)
C13—O1—C2—C1	−125.6 (6)	O10—C13—C14—O5	178.3 (3)
N1—C1—C2—O1	−62.8 (8)	O1—C13—C14—C15	175.0 (4)
C15—O3—C4—O2	−4.1 (7)	O10—C13—C14—C15	58.7 (5)
C15—O3—C4—C3	175.6 (4)	C4—O3—C15—C14	−127.5 (4)
C14—O5—C6—O4	7.2 (7)	C4—O3—C15—C16	113.3 (4)
C14—O5—C6—C5	−176.9 (4)	O5—C14—C15—O3	70.1 (4)
C16—O6—C8—O7	−1.7 (7)	C13—C14—C15—O3	−170.6 (3)
C16—O6—C8—C7	177.9 (4)	O5—C14—C15—C16	−171.2 (3)
C11—O9—C10—O8	1.2 (7)	C13—C14—C15—C16	−52.0 (5)
C11—O9—C10—C9	178.3 (4)	C8—O6—C16—C12	−114.6 (4)
C10—O9—C11—C12	−173.2 (4)	C8—O6—C16—C15	123.6 (4)
C13—O10—C12—C11	−172.7 (4)	O10—C12—C16—O6	−174.5 (3)
C13—O10—C12—C16	63.1 (5)	C11—C12—C16—O6	66.0 (4)
O9—C11—C12—O10	−69.9 (5)	O10—C12—C16—C15	−54.6 (4)
O9—C11—C12—C16	51.0 (5)	C11—C12—C16—C15	−174.1 (4)
C2—O1—C13—O10	−72.1 (6)	O3—C15—C16—O6	−73.1 (4)
C2—O1—C13—C14	171.2 (4)	C14—C15—C16—O6	169.5 (3)
C12—O10—C13—O1	177.7 (3)	O3—C15—C16—C12	167.2 (3)
C12—O10—C13—C14	−65.0 (5)	C14—C15—C16—C12	49.9 (5)
C6—O5—C14—C13	113.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O4	0.98	2.21	2.666 (6)	107
C15—H15A···O2	0.98	2.32	2.723 (6)	104
C16—H16A···O7	0.98	2.27	2.702 (6)	106
C16—H16A···O9	0.98	2.44	2.824 (5)	103
C9—H9B···O1ⁱ	0.96	2.48	3.402 (6)	160

Symmetry code: (i) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₃N₃O₁₀
M_r	417.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.9730 (14), 14.747 (3), 19.916 (4)
V (Å³)	2048.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.967, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	3276, 2152, 1428
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.156, 1.06
No. of reflections	2152
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O4	0.98	2.21	2.666 (6)	107
C15—H15A···O2	0.98	2.32	2.723 (6)	104
C16—H16A···O7	0.98	2.27	2.702 (6)	106
C16—H16A···O9	0.98	2.44	2.824 (5)	103
C9—H9B···O1ⁱ	0.96	2.48	3.402 (6)	160

Symmetry code: (i) x−1/2, −y+3/2, −z.

Acknowledgements

This work was supported by the President of the Chinese Academy of Forestry Foundation (CAFYBB2008009).

References

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