6-Acetoxy­methyl-3-[(2-hydr­oxy-3-methoxy­benzyl­idene)amino]-3,4,5,6-tetra­hydro-2H-pyran-2,4,5-triyl triacetate

Wang, Y.F.; Zhang, S.-H.; Chen, Z.F.; Liang, H.

doi:10.1107/S1600536810011475

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o990

doi:10.1107/S1600536810011475

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6-Acetoxymethyl-3-[(2-hydroxy-3-methoxybenzylidene)amino]-3,4,5,6-tetrahydro-2H-pyran-2,4,5-triyl triacetate

Yan Fei Wang,^a,^b Shu-Hua Zhang,^c Zhen Feng Chen ^b and Hong Liang ^b ^*

^aCollege of Chemistry and Chemical Engineering, Central South University, Changsha 410083, People's Republic of China, ^bSchool of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China, and ^cCollege of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China
^*Correspondence e-mail: zsh720108@163.com

(Received 18 March 2010; accepted 26 March 2010; online 31 March 2010)

The title compound, C₂₂H₂₇NO₁₁, was synthesized by the reaction of 4,5-diacetoxy-6-acetoxymethyl-3-aminotetrahydropyran-2-yl acetate and 2-hydroxy-3-methoxybenzaldehyde in ethanol. The molecule contains two six-membered rings, one of which is in a chair conformation, and an intramolecular O—H⋯N hydrogen bond is present.

Related literature

For a Schiff base complex, see: Zhang et al. (2003 ). For macrocyclic Schiff base compounds, see: Frischmann et al. (2008 ); Jiang et al. (2010 ). For 5,5′-dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol, which shows similar hydrogen-bonding to the title compound, see: Kargar et al. (2010 ).

Experimental

Crystal data

C₂₂H₂₇NO₁₁
M_r = 481.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.806 (3) Å
b = 11.151 (3) Å
c = 20.243 (5) Å
V = 2439.2 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
12313 measured reflections
2460 independent reflections
1506 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 1.03
2460 reflections
314 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.625 (4)	147

Data collection: SMART (Bruker 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011475/si2250sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011475/si2250Isup2.hkl

checkCIF report

Comment top

Schiff base compounds (Zhang, et al. 2003; Frischmann, et al. 2008; Jiang, et al. 2010) have aroused increasing interest because of their antiviral, anticancer and antibacterial activities. Herein, we report the synthesis and crystal structure of a new schiff base compound, (I), prepared by the reaction of Acetic acid 4,5-diacetoxy-6-acetoxymethyl-3-amino]-tetrahydro-pyran-2-yl ester and 2-hydroxy-3-methoxy-benzaldehyde.

The molecular structure of (I) reveals the 2-hydroxy-3-methoxy-benzaldehyde configuration with one acetic acid 4,5-diacetoxy-6-acetoxymethyl-3-amino]-tetrahydro-pyran-2-yl ester molecule on N1-position (Fig. 1). The dihedral angle between the benzene ring of 2-hydroxy-3-methoxy-benzylidene group and the plane of C9, C10, C12, C13 is 56.78 (3) °. The other dihedral angle between the four acetic acid groups and the plane of C9, C10, C12, C13 are in the range of 57.0–111.7°. There is an intramolecular O–H···N hygrogen bond between the phenol and imido-group(Table 1). The distance of N1···H1 is substantially shorter than the van der Waals distance of 2.75 Å for the N and H distance. The hydrogen bond between the phenol and imido-group are similar to those found in the crystal structure of 5,5'-Dimethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenol (Kargar, et al. 2010). In the molecule, the C9 has S* configuration, while the C10, C11, C12, C13 are in R* configuration which form a R* configuration molecule.

Related literature top

For a Schiff base complex, see: Zhang et al. (2007). For macrocyclic Schiff base compounds, see: Frischmann et al. (2008); Jiang et al. (2010). [How are these compounds related to the title compound?] For 5,5'-dimethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenol, which shows similar hydrogen-bonding, see: Kargar et al. (2010).

For related literature, see: Zhang et al. (2003).

Experimental top

The compound Acetic acid 4,5-diacetoxy-6-acetoxymethyl- 3-amino]-tetrahydro-pyran-2-yl ester (0.182 g, 0.5 mmol) was dissolved in ethanol (10 ml). To this solution, 2-hydroxy-3-methoxy-benzaldehyde (0.076 g, 1 mmol) was added and the mixture was stirred and refluxed at 333 K for 3 h. After cooling to room temperature and filtration, the filtrate was left to stand at room temperature. Colourless block crystals suitable for X-ray diffraction were obtained in a yield of 53 %. Analysis found (%): C 54.64, H 5.69, N 2.94; C₂₂H₂₇NO₁₁ requires (%) : C 54.88, H 5.65, N 2.91.

Computing details top

Data collection: SMART (Bruker 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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

Fig. 1. The molecular structure of (I), showing 30 % probability displacement ellipsoids. H-atoms were omitted.

6-Acetoxymethyl-3-[(2-hydroxy-3-methoxybenzylidene)amino]-3,4,5,6-tetrahydro- 2H-pyran-2,4,5-triyl triacetate top

Crystal data top

C₂₂H₂₇NO₁₁	F(000) = 1016
M_r = 481.45	D_x = 1.311 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1384 reflections
a = 10.806 (3) Å	θ = 2.6–18.6°
b = 11.151 (3) Å	µ = 0.11 mm⁻¹
c = 20.243 (5) Å	T = 296 K
V = 2439.2 (11) Å³	Block, colourless
Z = 4	0.32 × 0.28 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.061
Graphite monochromator	θ_max = 25.1°, θ_min = 2.0°
phi and ω scans	h = −12→12
12313 measured reflections	k = −12→13
2460 independent reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0572P)² + 0.177P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2460 reflections	Δρ_max = 0.17 e Å⁻³
314 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (13)

Crystal data top

C₂₂H₂₇NO₁₁	V = 2439.2 (11) Å³
M_r = 481.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.806 (3) Å	µ = 0.11 mm⁻¹
b = 11.151 (3) Å	T = 296 K
c = 20.243 (5) Å	0.32 × 0.28 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1506 reflections with I > 2σ(I)
12313 measured reflections	R_int = 0.061
2460 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
2460 reflections	Δρ_min = −0.14 e Å⁻³
314 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
N1	0.4441 (3)	0.0108 (3)	−0.01092 (15)	0.0566 (9)
O1	0.2954 (3)	−0.1155 (2)	−0.08619 (14)	0.0650 (8)
H1	0.3485	−0.1041	−0.0580	0.098*
O2	0.1136 (3)	−0.1188 (3)	−0.17050 (16)	0.0796 (10)
O3	0.5742 (3)	−0.0540 (2)	0.15220 (13)	0.0587 (8)
O4	0.3813 (3)	0.0041 (3)	0.12705 (14)	0.0679 (8)
O5	0.2923 (4)	−0.1724 (4)	0.1455 (2)	0.1216 (16)
O6	0.7049 (3)	0.0885 (2)	−0.01748 (13)	0.0653 (8)
O7	0.7871 (5)	−0.0297 (4)	−0.09480 (18)	0.1221 (16)
O8	0.8528 (3)	−0.1002 (3)	0.05512 (15)	0.0654 (8)
O9	0.9690 (4)	0.0649 (4)	0.0508 (2)	0.1069 (14)
O10	0.8042 (3)	−0.0141 (3)	0.21533 (14)	0.0709 (9)
O11	0.9237 (4)	−0.1041 (4)	0.2885 (2)	0.1134 (15)
C1	0.3183 (4)	0.0980 (4)	−0.09509 (19)	0.0564 (11)
C2	0.2611 (4)	−0.0094 (4)	−0.11268 (17)	0.0523 (10)
C3	0.1641 (4)	−0.0085 (4)	−0.1582 (2)	0.0579 (11)
C4	0.1275 (5)	0.0970 (4)	−0.1868 (2)	0.0686 (13)
H4	0.0620	0.0974	−0.2166	0.082*
C5	0.1877 (6)	0.2026 (4)	−0.1716 (2)	0.0830 (17)
H5	0.1651	0.2735	−0.1925	0.100*
C6	0.2796 (5)	0.2030 (4)	−0.1261 (2)	0.0763 (15)
H6	0.3178	0.2752	−0.1153	0.092*
C7	0.0039 (5)	−0.1240 (5)	−0.2101 (2)	0.0794 (15)
H7A	−0.0601	−0.0770	−0.1898	0.119*
H7B	−0.0230	−0.2057	−0.2139	0.119*
H7C	0.0213	−0.0927	−0.2533	0.119*
C8	0.4107 (4)	0.1028 (4)	−0.0435 (2)	0.0593 (11)
H8	0.4473	0.1762	−0.0338	0.071*
C9	0.4872 (4)	−0.0535 (4)	0.1006 (2)	0.0590 (11)
H9	0.4679	−0.1351	0.0859	0.071*
C10	0.5319 (4)	0.0245 (4)	0.0434 (2)	0.0545 (11)
H10	0.5334	0.1086	0.0575	0.065*
C11	0.6604 (4)	−0.0123 (4)	0.02084 (19)	0.0537 (10)
H11	0.6556	−0.0841	−0.0070	0.064*
C12	0.7471 (4)	−0.0339 (3)	0.07825 (18)	0.0524 (10)
H12	0.7737	0.0427	0.0972	0.063*
C13	0.6865 (4)	−0.1114 (4)	0.13127 (19)	0.0562 (11)
H13	0.6663	−0.1898	0.1123	0.067*
C14	0.2886 (5)	−0.0675 (6)	0.1493 (3)	0.0823 (16)
C15	0.1874 (5)	0.0050 (6)	0.1787 (3)	0.1032 (19)
H15A	0.1311	−0.0468	0.2018	0.155*
H15B	0.1438	0.0466	0.1443	0.155*
H15C	0.2217	0.0622	0.2091	0.155*
C16	0.7680 (6)	0.0677 (5)	−0.0739 (2)	0.0792 (15)
C17	0.8086 (7)	0.1835 (6)	−0.1032 (3)	0.120 (2)
H17A	0.8882	0.1734	−0.1234	0.180*
H17B	0.8140	0.2432	−0.0692	0.180*
H17C	0.7498	0.2086	−0.1359	0.180*
C18	0.9585 (5)	−0.0393 (6)	0.0418 (3)	0.0821 (15)
C19	1.0539 (6)	−0.1225 (6)	0.0159 (3)	0.124 (2)
H19A	1.0194	−0.1692	−0.0194	0.187*
H19B	1.0809	−0.1750	0.0507	0.187*
H19C	1.1231	−0.0773	−0.0003	0.187*
C20	0.7666 (5)	−0.1294 (4)	0.1910 (2)	0.0670 (13)
H20A	0.7209	−0.1721	0.2249	0.080*
H20B	0.8388	−0.1766	0.1794	0.080*
C21	0.8859 (5)	−0.0145 (5)	0.2653 (2)	0.0731 (14)
C22	0.9208 (6)	0.1090 (5)	0.2857 (3)	0.0973 (18)
H22A	0.8510	0.1476	0.3059	0.146*
H22B	0.9463	0.1540	0.2476	0.146*
H22C	0.9878	0.1053	0.3168	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.062 (2)	0.055 (2)	0.0534 (19)	0.0008 (19)	−0.0100 (17)	−0.0002 (18)
O1	0.069 (2)	0.0494 (16)	0.077 (2)	0.0002 (16)	−0.0246 (18)	0.0102 (14)
O2	0.083 (2)	0.061 (2)	0.095 (2)	−0.0107 (18)	−0.037 (2)	0.0081 (17)
O3	0.060 (2)	0.0645 (18)	0.0515 (17)	0.0054 (15)	−0.0011 (16)	0.0003 (13)
O4	0.0571 (19)	0.075 (2)	0.0714 (18)	0.0045 (19)	0.0075 (17)	0.0013 (17)
O5	0.099 (3)	0.096 (3)	0.170 (4)	−0.015 (3)	0.035 (3)	0.016 (3)
O6	0.074 (2)	0.0671 (18)	0.0549 (17)	−0.0070 (17)	−0.0021 (17)	0.0039 (15)
O7	0.175 (5)	0.109 (3)	0.083 (2)	−0.002 (3)	0.043 (3)	−0.015 (2)
O8	0.057 (2)	0.0658 (18)	0.0736 (19)	0.0114 (17)	0.0010 (16)	−0.0063 (16)
O9	0.073 (3)	0.095 (3)	0.153 (4)	−0.014 (2)	0.009 (3)	−0.006 (3)
O10	0.080 (2)	0.0673 (19)	0.0651 (17)	0.0067 (19)	−0.0188 (18)	−0.0055 (15)
O11	0.113 (4)	0.111 (3)	0.116 (3)	0.022 (3)	−0.055 (3)	0.003 (3)
C1	0.067 (3)	0.049 (2)	0.054 (2)	0.004 (2)	−0.008 (2)	0.000 (2)
C2	0.057 (3)	0.050 (2)	0.049 (2)	0.001 (2)	−0.005 (2)	0.0066 (19)
C3	0.062 (3)	0.052 (2)	0.059 (2)	0.002 (2)	−0.011 (2)	0.005 (2)
C4	0.072 (3)	0.064 (3)	0.070 (3)	0.009 (3)	−0.019 (3)	0.003 (2)
C5	0.107 (5)	0.051 (3)	0.091 (3)	0.006 (3)	−0.042 (4)	0.013 (2)
C6	0.094 (4)	0.047 (2)	0.088 (3)	−0.004 (3)	−0.030 (3)	−0.001 (2)
C7	0.073 (4)	0.079 (3)	0.085 (3)	−0.017 (3)	−0.026 (3)	0.014 (3)
C8	0.060 (3)	0.054 (2)	0.064 (3)	−0.002 (2)	−0.004 (2)	−0.005 (2)
C9	0.054 (3)	0.066 (3)	0.057 (3)	0.004 (2)	−0.002 (2)	−0.001 (2)
C10	0.056 (3)	0.051 (2)	0.057 (2)	−0.003 (2)	−0.007 (2)	−0.004 (2)
C11	0.059 (3)	0.047 (2)	0.055 (2)	−0.003 (2)	−0.001 (2)	−0.004 (2)
C12	0.054 (3)	0.050 (2)	0.053 (2)	0.007 (2)	−0.001 (2)	−0.0019 (18)
C13	0.062 (3)	0.053 (2)	0.054 (2)	0.002 (2)	−0.006 (2)	−0.002 (2)
C14	0.062 (4)	0.103 (4)	0.082 (3)	0.000 (3)	0.007 (3)	0.019 (3)
C15	0.051 (3)	0.151 (5)	0.108 (4)	0.009 (4)	0.012 (3)	0.021 (4)
C16	0.088 (4)	0.092 (4)	0.058 (3)	−0.012 (3)	0.000 (3)	0.003 (3)
C17	0.147 (7)	0.131 (5)	0.083 (4)	−0.049 (5)	0.010 (4)	0.017 (4)
C18	0.060 (4)	0.101 (4)	0.086 (4)	0.012 (3)	0.007 (3)	0.004 (3)
C19	0.083 (4)	0.158 (6)	0.132 (5)	0.035 (5)	0.023 (4)	−0.031 (5)
C20	0.072 (3)	0.063 (3)	0.066 (3)	0.006 (3)	−0.009 (3)	0.000 (2)
C21	0.067 (3)	0.088 (4)	0.064 (3)	0.006 (3)	−0.013 (3)	−0.006 (3)
C22	0.079 (4)	0.119 (5)	0.094 (4)	−0.002 (4)	−0.017 (3)	−0.028 (4)

Geometric parameters (Å, º) top

N1—C8	1.271 (5)	C7—H7B	0.9600
N1—C10	1.461 (5)	C7—H7C	0.9600
O1—C2	1.351 (4)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.526 (6)
O2—C3	1.368 (5)	C9—H9	0.9800
O2—C7	1.433 (5)	C10—C11	1.519 (6)
O3—C9	1.406 (5)	C10—H10	0.9800
O3—C13	1.435 (5)	C11—C12	1.512 (5)
O4—C14	1.359 (6)	C11—H11	0.9800
O4—C9	1.417 (5)	C12—C13	1.525 (6)
O5—C14	1.172 (6)	C12—H12	0.9800
O6—C16	1.350 (6)	C13—C20	1.501 (6)
O6—C11	1.448 (5)	C13—H13	0.9800
O7—C16	1.184 (6)	C14—C15	1.485 (7)
O8—C18	1.356 (6)	C15—H15A	0.9600
O8—C12	1.438 (5)	C15—H15B	0.9600
O9—C18	1.182 (6)	C15—H15C	0.9600
O10—C21	1.343 (5)	C16—C17	1.486 (7)
O10—C20	1.435 (5)	C17—H17A	0.9600
O11—C21	1.176 (5)	C17—H17B	0.9600
C1—C6	1.393 (6)	C17—H17C	0.9600
C1—C2	1.394 (5)	C18—C19	1.483 (7)
C1—C8	1.446 (6)	C19—H19A	0.9600
C2—C3	1.395 (5)	C19—H19B	0.9600
C3—C4	1.370 (6)	C19—H19C	0.9600
C4—C5	1.380 (6)	C20—H20A	0.9700
C4—H4	0.9300	C20—H20B	0.9700
C5—C6	1.354 (6)	C21—C22	1.487 (7)
C5—H5	0.9300	C22—H22A	0.9600
C6—H6	0.9300	C22—H22B	0.9600
C7—H7A	0.9600	C22—H22C	0.9600

C8—N1—C10	119.4 (3)	O8—C12—C13	106.2 (3)
C2—O1—H1	109.5	C11—C12—C13	111.4 (3)
C3—O2—C7	117.9 (3)	O8—C12—H12	110.1
C9—O3—C13	110.4 (3)	C11—C12—H12	110.1
C14—O4—C9	117.0 (4)	C13—C12—H12	110.1
C16—O6—C11	119.2 (4)	O3—C13—C20	108.0 (3)
C18—O8—C12	118.5 (3)	O3—C13—C12	108.6 (3)
C21—O10—C20	116.2 (4)	C20—C13—C12	113.3 (4)
C6—C1—C2	118.3 (4)	O3—C13—H13	109.0
C6—C1—C8	120.2 (4)	C20—C13—H13	109.0
C2—C1—C8	121.5 (4)	C12—C13—H13	109.0
O1—C2—C1	122.0 (3)	O5—C14—O4	122.6 (6)
O1—C2—C3	118.3 (4)	O5—C14—C15	126.5 (6)
C1—C2—C3	119.7 (4)	O4—C14—C15	110.8 (5)
O2—C3—C4	125.4 (4)	C14—C15—H15A	109.5
O2—C3—C2	114.4 (3)	C14—C15—H15B	109.5
C4—C3—C2	120.2 (4)	H15A—C15—H15B	109.5
C3—C4—C5	120.1 (4)	C14—C15—H15C	109.5
C3—C4—H4	120.0	H15A—C15—H15C	109.5
C5—C4—H4	120.0	H15B—C15—H15C	109.5
C6—C5—C4	120.1 (4)	O7—C16—O6	123.2 (5)
C6—C5—H5	120.0	O7—C16—C17	127.0 (5)
C4—C5—H5	120.0	O6—C16—C17	109.7 (5)
C5—C6—C1	121.6 (4)	C16—C17—H17A	109.5
C5—C6—H6	119.2	C16—C17—H17B	109.5
C1—C6—H6	119.2	H17A—C17—H17B	109.5
O2—C7—H7A	109.5	C16—C17—H17C	109.5
O2—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
O2—C7—H7C	109.5	O9—C18—O8	122.9 (5)
H7A—C7—H7C	109.5	O9—C18—C19	127.1 (6)
H7B—C7—H7C	109.5	O8—C18—C19	110.0 (5)
N1—C8—C1	122.8 (4)	C18—C19—H19A	109.5
N1—C8—H8	118.6	C18—C19—H19B	109.5
C1—C8—H8	118.6	H19A—C19—H19B	109.5
O3—C9—O4	105.2 (3)	C18—C19—H19C	109.5
O3—C9—C10	110.7 (3)	H19A—C19—H19C	109.5
O4—C9—C10	106.5 (3)	H19B—C19—H19C	109.5
O3—C9—H9	111.4	O10—C20—C13	108.6 (3)
O4—C9—H9	111.4	O10—C20—H20A	110.0
C10—C9—H9	111.4	C13—C20—H20A	110.0
N1—C10—C11	109.8 (3)	O10—C20—H20B	110.0
N1—C10—C9	107.9 (3)	C13—C20—H20B	110.0
C11—C10—C9	111.4 (3)	H20A—C20—H20B	108.3
N1—C10—H10	109.3	O11—C21—O10	122.1 (5)
C11—C10—H10	109.3	O11—C21—C22	126.0 (5)
C9—C10—H10	109.3	O10—C21—C22	111.9 (5)
O6—C11—C12	109.3 (3)	C21—C22—H22A	109.5
O6—C11—C10	104.8 (3)	C21—C22—H22B	109.5
C12—C11—C10	112.2 (3)	H22A—C22—H22B	109.5
O6—C11—H11	110.1	C21—C22—H22C	109.5
C12—C11—H11	110.1	H22A—C22—H22C	109.5
C10—C11—H11	110.1	H22B—C22—H22C	109.5
O8—C12—C11	108.9 (3)

C6—C1—C2—O1	178.2 (4)	C16—O6—C11—C12	100.4 (4)
C8—C1—C2—O1	−5.2 (6)	C16—O6—C11—C10	−139.2 (4)
C6—C1—C2—C3	−2.7 (6)	N1—C10—C11—O6	77.7 (4)
C8—C1—C2—C3	173.9 (4)	C9—C10—C11—O6	−162.9 (3)
C7—O2—C3—C4	−8.2 (7)	N1—C10—C11—C12	−163.8 (3)
C7—O2—C3—C2	172.3 (4)	C9—C10—C11—C12	−44.4 (4)
O1—C2—C3—O2	0.3 (6)	C18—O8—C12—C11	99.4 (4)
C1—C2—C3—O2	−178.7 (4)	C18—O8—C12—C13	−140.6 (4)
O1—C2—C3—C4	−179.1 (4)	O6—C11—C12—O8	−80.6 (4)
C1—C2—C3—C4	1.8 (6)	C10—C11—C12—O8	163.6 (3)
O2—C3—C4—C5	−178.4 (5)	O6—C11—C12—C13	162.6 (3)
C2—C3—C4—C5	1.0 (7)	C10—C11—C12—C13	46.8 (4)
C3—C4—C5—C6	−2.8 (8)	C9—O3—C13—C20	−169.9 (3)
C4—C5—C6—C1	1.8 (8)	C9—O3—C13—C12	66.9 (4)
C2—C1—C6—C5	0.9 (7)	O8—C12—C13—O3	−175.1 (3)
C8—C1—C6—C5	−175.7 (5)	C11—C12—C13—O3	−56.7 (4)
C10—N1—C8—C1	−175.9 (4)	O8—C12—C13—C20	64.9 (4)
C6—C1—C8—N1	175.8 (4)	C11—C12—C13—C20	−176.7 (3)
C2—C1—C8—N1	−0.8 (7)	C9—O4—C14—O5	−2.3 (8)
C13—O3—C9—O4	179.7 (3)	C9—O4—C14—C15	176.9 (4)
C13—O3—C9—C10	−65.7 (4)	C11—O6—C16—O7	1.7 (8)
C14—O4—C9—O3	−98.4 (4)	C11—O6—C16—C17	−177.7 (4)
C14—O4—C9—C10	144.0 (4)	C12—O8—C18—O9	3.0 (8)
C8—N1—C10—C11	−100.9 (4)	C12—O8—C18—C19	−177.5 (4)
C8—N1—C10—C9	137.6 (4)	C21—O10—C20—C13	−174.1 (4)
O3—C9—C10—N1	174.0 (3)	O3—C13—C20—O10	−66.5 (4)
O4—C9—C10—N1	−72.1 (4)	C12—C13—C20—O10	53.8 (5)
O3—C9—C10—C11	53.4 (4)	C20—O10—C21—O11	−0.8 (7)
O4—C9—C10—C11	167.3 (3)	C20—O10—C21—C22	178.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.625 (4)	147

Experimental details

Crystal data
Chemical formula	C₂₂H₂₇NO₁₁
M_r	481.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	10.806 (3), 11.151 (3), 20.243 (5)
V (Å³)	2439.2 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12313, 2460, 1506
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.126, 1.03
No. of reflections	2460
No. of parameters	314
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: SMART (Bruker 2004), SAINT (Bruker, 2004), 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
O1—H1···N1	0.82	1.90	2.625 (4)	146.5

Acknowledgements

We acknowledge financial support by the National Natural Science Foundation of China (No. 20861002) and the 973 Plan of China (2009CB526503).

References

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Frischmann, P. D., Jiang, J., Hui, J. K. H., Grzybowski, J. J. & MacLachlan, M. J. (2008). Org. Lett. 10, 1255–1258. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jiang, J. & MacLachlan, M. J. (2010). Org. Lett. 12, 1020–1023. Web of Science CrossRef CAS PubMed Google Scholar
Kargar, H., Kia, R., Khan, I. U., Sahraei, A. & Aberoomand Azar, P. (2010). Acta Cryst. E66, o728. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S. H., Jiang, Y. M., Xiao, Y. & Zhou, Z. Y. (2003). Chin. J. Inorg. Chem. 19, 517–520. CAS Google Scholar

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Volume 66| Part 4| April 2010| Page o990

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

6-Acet­oxy­methyl-3-[(2-hydr­­oxy-3-meth­oxy­benzyl­­idene)amino]-3,4,5,6-tetra­hydro-2H-pyran-2,4,5-triyl tri­acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-Acetoxymethyl-3-[(2-hydroxy-3-methoxybenzylidene)amino]-3,4,5,6-tetrahydro-2H-pyran-2,4,5-triyl triacetate