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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o990.
Published online 2010 March 31. doi:  10.1107/S1600536810011475
PMCID: PMC2983953

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

Abstract

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 [triangle]). For macrocyclic Schiff base compounds, see: Frischmann et al. (2008 [triangle]); Jiang et al. (2010 [triangle]). 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 [triangle]).

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Object name is e-66-0o990-scheme1.jpg

Experimental

Crystal data

  • C22H27NO11
  • M r = 481.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o990-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.126
  • S = 1.03
  • 2460 reflections
  • 314 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms were positioned geometrically and were refined as riding, with (C—H 0.93–0.98 Å, O—H 0.82 Å with Uiso(H) = 1.2 Ueq(aromatic C) and Uiso(H) = 1.5Ueq(other C or O).

In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

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

Crystal data

C22H27NO11F(000) = 1016
Mr = 481.45Dx = 1.311 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1384 reflections
a = 10.806 (3) Åθ = 2.6–18.6°
b = 11.151 (3) ŵ = 0.11 mm1
c = 20.243 (5) ÅT = 296 K
V = 2439.2 (11) Å3Block, colourless
Z = 40.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer1506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
graphiteθmax = 25.1°, θmin = 2.0°
phi and ω scansh = −12→12
12313 measured reflectionsk = −12→13
2460 independent reflectionsl = −24→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.126w = 1/[σ2(Fo2) + (0.0572P)2 + 0.177P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2460 reflectionsΔρmax = 0.17 e Å3
314 parametersΔρmin = −0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0074 (13)

Special details

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)

xyzUiso*/Ueq
N10.4441 (3)0.0108 (3)−0.01092 (15)0.0566 (9)
O10.2954 (3)−0.1155 (2)−0.08619 (14)0.0650 (8)
H10.3485−0.1041−0.05800.098*
O20.1136 (3)−0.1188 (3)−0.17050 (16)0.0796 (10)
O30.5742 (3)−0.0540 (2)0.15220 (13)0.0587 (8)
O40.3813 (3)0.0041 (3)0.12705 (14)0.0679 (8)
O50.2923 (4)−0.1724 (4)0.1455 (2)0.1216 (16)
O60.7049 (3)0.0885 (2)−0.01748 (13)0.0653 (8)
O70.7871 (5)−0.0297 (4)−0.09480 (18)0.1221 (16)
O80.8528 (3)−0.1002 (3)0.05512 (15)0.0654 (8)
O90.9690 (4)0.0649 (4)0.0508 (2)0.1069 (14)
O100.8042 (3)−0.0141 (3)0.21533 (14)0.0709 (9)
O110.9237 (4)−0.1041 (4)0.2885 (2)0.1134 (15)
C10.3183 (4)0.0980 (4)−0.09509 (19)0.0564 (11)
C20.2611 (4)−0.0094 (4)−0.11268 (17)0.0523 (10)
C30.1641 (4)−0.0085 (4)−0.1582 (2)0.0579 (11)
C40.1275 (5)0.0970 (4)−0.1868 (2)0.0686 (13)
H40.06200.0974−0.21660.082*
C50.1877 (6)0.2026 (4)−0.1716 (2)0.0830 (17)
H50.16510.2735−0.19250.100*
C60.2796 (5)0.2030 (4)−0.1261 (2)0.0763 (15)
H60.31780.2752−0.11530.092*
C70.0039 (5)−0.1240 (5)−0.2101 (2)0.0794 (15)
H7A−0.0601−0.0770−0.18980.119*
H7B−0.0230−0.2057−0.21390.119*
H7C0.0213−0.0927−0.25330.119*
C80.4107 (4)0.1028 (4)−0.0435 (2)0.0593 (11)
H80.44730.1762−0.03380.071*
C90.4872 (4)−0.0535 (4)0.1006 (2)0.0590 (11)
H90.4679−0.13510.08590.071*
C100.5319 (4)0.0245 (4)0.0434 (2)0.0545 (11)
H100.53340.10860.05750.065*
C110.6604 (4)−0.0123 (4)0.02084 (19)0.0537 (10)
H110.6556−0.0841−0.00700.064*
C120.7471 (4)−0.0339 (3)0.07825 (18)0.0524 (10)
H120.77370.04270.09720.063*
C130.6865 (4)−0.1114 (4)0.13127 (19)0.0562 (11)
H130.6663−0.18980.11230.067*
C140.2886 (5)−0.0675 (6)0.1493 (3)0.0823 (16)
C150.1874 (5)0.0050 (6)0.1787 (3)0.1032 (19)
H15A0.1311−0.04680.20180.155*
H15B0.14380.04660.14430.155*
H15C0.22170.06220.20910.155*
C160.7680 (6)0.0677 (5)−0.0739 (2)0.0792 (15)
C170.8086 (7)0.1835 (6)−0.1032 (3)0.120 (2)
H17A0.88820.1734−0.12340.180*
H17B0.81400.2432−0.06920.180*
H17C0.74980.2086−0.13590.180*
C180.9585 (5)−0.0393 (6)0.0418 (3)0.0821 (15)
C191.0539 (6)−0.1225 (6)0.0159 (3)0.124 (2)
H19A1.0194−0.1692−0.01940.187*
H19B1.0809−0.17500.05070.187*
H19C1.1231−0.0773−0.00030.187*
C200.7666 (5)−0.1294 (4)0.1910 (2)0.0670 (13)
H20A0.7209−0.17210.22490.080*
H20B0.8388−0.17660.17940.080*
C210.8859 (5)−0.0145 (5)0.2653 (2)0.0731 (14)
C220.9208 (6)0.1090 (5)0.2857 (3)0.0973 (18)
H22A0.85100.14760.30590.146*
H22B0.94630.15400.24760.146*
H22C0.98780.10530.31680.146*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.062 (2)0.055 (2)0.0534 (19)0.0008 (19)−0.0100 (17)−0.0002 (18)
O10.069 (2)0.0494 (16)0.077 (2)0.0002 (16)−0.0246 (18)0.0102 (14)
O20.083 (2)0.061 (2)0.095 (2)−0.0107 (18)−0.037 (2)0.0081 (17)
O30.060 (2)0.0645 (18)0.0515 (17)0.0054 (15)−0.0011 (16)0.0003 (13)
O40.0571 (19)0.075 (2)0.0714 (18)0.0045 (19)0.0075 (17)0.0013 (17)
O50.099 (3)0.096 (3)0.170 (4)−0.015 (3)0.035 (3)0.016 (3)
O60.074 (2)0.0671 (18)0.0549 (17)−0.0070 (17)−0.0021 (17)0.0039 (15)
O70.175 (5)0.109 (3)0.083 (2)−0.002 (3)0.043 (3)−0.015 (2)
O80.057 (2)0.0658 (18)0.0736 (19)0.0114 (17)0.0010 (16)−0.0063 (16)
O90.073 (3)0.095 (3)0.153 (4)−0.014 (2)0.009 (3)−0.006 (3)
O100.080 (2)0.0673 (19)0.0651 (17)0.0067 (19)−0.0188 (18)−0.0055 (15)
O110.113 (4)0.111 (3)0.116 (3)0.022 (3)−0.055 (3)0.003 (3)
C10.067 (3)0.049 (2)0.054 (2)0.004 (2)−0.008 (2)0.000 (2)
C20.057 (3)0.050 (2)0.049 (2)0.001 (2)−0.005 (2)0.0066 (19)
C30.062 (3)0.052 (2)0.059 (2)0.002 (2)−0.011 (2)0.005 (2)
C40.072 (3)0.064 (3)0.070 (3)0.009 (3)−0.019 (3)0.003 (2)
C50.107 (5)0.051 (3)0.091 (3)0.006 (3)−0.042 (4)0.013 (2)
C60.094 (4)0.047 (2)0.088 (3)−0.004 (3)−0.030 (3)−0.001 (2)
C70.073 (4)0.079 (3)0.085 (3)−0.017 (3)−0.026 (3)0.014 (3)
C80.060 (3)0.054 (2)0.064 (3)−0.002 (2)−0.004 (2)−0.005 (2)
C90.054 (3)0.066 (3)0.057 (3)0.004 (2)−0.002 (2)−0.001 (2)
C100.056 (3)0.051 (2)0.057 (2)−0.003 (2)−0.007 (2)−0.004 (2)
C110.059 (3)0.047 (2)0.055 (2)−0.003 (2)−0.001 (2)−0.004 (2)
C120.054 (3)0.050 (2)0.053 (2)0.007 (2)−0.001 (2)−0.0019 (18)
C130.062 (3)0.053 (2)0.054 (2)0.002 (2)−0.006 (2)−0.002 (2)
C140.062 (4)0.103 (4)0.082 (3)0.000 (3)0.007 (3)0.019 (3)
C150.051 (3)0.151 (5)0.108 (4)0.009 (4)0.012 (3)0.021 (4)
C160.088 (4)0.092 (4)0.058 (3)−0.012 (3)0.000 (3)0.003 (3)
C170.147 (7)0.131 (5)0.083 (4)−0.049 (5)0.010 (4)0.017 (4)
C180.060 (4)0.101 (4)0.086 (4)0.012 (3)0.007 (3)0.004 (3)
C190.083 (4)0.158 (6)0.132 (5)0.035 (5)0.023 (4)−0.031 (5)
C200.072 (3)0.063 (3)0.066 (3)0.006 (3)−0.009 (3)0.000 (2)
C210.067 (3)0.088 (4)0.064 (3)0.006 (3)−0.013 (3)−0.006 (3)
C220.079 (4)0.119 (5)0.094 (4)−0.002 (4)−0.017 (3)−0.028 (4)

Geometric parameters (Å, °)

N1—C81.271 (5)C7—H7B0.9600
N1—C101.461 (5)C7—H7C0.9600
O1—C21.351 (4)C8—H80.9300
O1—H10.8200C9—C101.526 (6)
O2—C31.368 (5)C9—H90.9800
O2—C71.433 (5)C10—C111.519 (6)
O3—C91.406 (5)C10—H100.9800
O3—C131.435 (5)C11—C121.512 (5)
O4—C141.359 (6)C11—H110.9800
O4—C91.417 (5)C12—C131.525 (6)
O5—C141.172 (6)C12—H120.9800
O6—C161.350 (6)C13—C201.501 (6)
O6—C111.448 (5)C13—H130.9800
O7—C161.184 (6)C14—C151.485 (7)
O8—C181.356 (6)C15—H15A0.9600
O8—C121.438 (5)C15—H15B0.9600
O9—C181.182 (6)C15—H15C0.9600
O10—C211.343 (5)C16—C171.486 (7)
O10—C201.435 (5)C17—H17A0.9600
O11—C211.176 (5)C17—H17B0.9600
C1—C61.393 (6)C17—H17C0.9600
C1—C21.394 (5)C18—C191.483 (7)
C1—C81.446 (6)C19—H19A0.9600
C2—C31.395 (5)C19—H19B0.9600
C3—C41.370 (6)C19—H19C0.9600
C4—C51.380 (6)C20—H20A0.9700
C4—H40.9300C20—H20B0.9700
C5—C61.354 (6)C21—C221.487 (7)
C5—H50.9300C22—H22A0.9600
C6—H60.9300C22—H22B0.9600
C7—H7A0.9600C22—H22C0.9600
C8—N1—C10119.4 (3)O8—C12—C13106.2 (3)
C2—O1—H1109.5C11—C12—C13111.4 (3)
C3—O2—C7117.9 (3)O8—C12—H12110.1
C9—O3—C13110.4 (3)C11—C12—H12110.1
C14—O4—C9117.0 (4)C13—C12—H12110.1
C16—O6—C11119.2 (4)O3—C13—C20108.0 (3)
C18—O8—C12118.5 (3)O3—C13—C12108.6 (3)
C21—O10—C20116.2 (4)C20—C13—C12113.3 (4)
C6—C1—C2118.3 (4)O3—C13—H13109.0
C6—C1—C8120.2 (4)C20—C13—H13109.0
C2—C1—C8121.5 (4)C12—C13—H13109.0
O1—C2—C1122.0 (3)O5—C14—O4122.6 (6)
O1—C2—C3118.3 (4)O5—C14—C15126.5 (6)
C1—C2—C3119.7 (4)O4—C14—C15110.8 (5)
O2—C3—C4125.4 (4)C14—C15—H15A109.5
O2—C3—C2114.4 (3)C14—C15—H15B109.5
C4—C3—C2120.2 (4)H15A—C15—H15B109.5
C3—C4—C5120.1 (4)C14—C15—H15C109.5
C3—C4—H4120.0H15A—C15—H15C109.5
C5—C4—H4120.0H15B—C15—H15C109.5
C6—C5—C4120.1 (4)O7—C16—O6123.2 (5)
C6—C5—H5120.0O7—C16—C17127.0 (5)
C4—C5—H5120.0O6—C16—C17109.7 (5)
C5—C6—C1121.6 (4)C16—C17—H17A109.5
C5—C6—H6119.2C16—C17—H17B109.5
C1—C6—H6119.2H17A—C17—H17B109.5
O2—C7—H7A109.5C16—C17—H17C109.5
O2—C7—H7B109.5H17A—C17—H17C109.5
H7A—C7—H7B109.5H17B—C17—H17C109.5
O2—C7—H7C109.5O9—C18—O8122.9 (5)
H7A—C7—H7C109.5O9—C18—C19127.1 (6)
H7B—C7—H7C109.5O8—C18—C19110.0 (5)
N1—C8—C1122.8 (4)C18—C19—H19A109.5
N1—C8—H8118.6C18—C19—H19B109.5
C1—C8—H8118.6H19A—C19—H19B109.5
O3—C9—O4105.2 (3)C18—C19—H19C109.5
O3—C9—C10110.7 (3)H19A—C19—H19C109.5
O4—C9—C10106.5 (3)H19B—C19—H19C109.5
O3—C9—H9111.4O10—C20—C13108.6 (3)
O4—C9—H9111.4O10—C20—H20A110.0
C10—C9—H9111.4C13—C20—H20A110.0
N1—C10—C11109.8 (3)O10—C20—H20B110.0
N1—C10—C9107.9 (3)C13—C20—H20B110.0
C11—C10—C9111.4 (3)H20A—C20—H20B108.3
N1—C10—H10109.3O11—C21—O10122.1 (5)
C11—C10—H10109.3O11—C21—C22126.0 (5)
C9—C10—H10109.3O10—C21—C22111.9 (5)
O6—C11—C12109.3 (3)C21—C22—H22A109.5
O6—C11—C10104.8 (3)C21—C22—H22B109.5
C12—C11—C10112.2 (3)H22A—C22—H22B109.5
O6—C11—H11110.1C21—C22—H22C109.5
C12—C11—H11110.1H22A—C22—H22C109.5
C10—C11—H11110.1H22B—C22—H22C109.5
O8—C12—C11108.9 (3)
C6—C1—C2—O1178.2 (4)C16—O6—C11—C12100.4 (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—O677.7 (4)
C8—C1—C2—C3173.9 (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—C2172.3 (4)C9—C10—C11—C12−44.4 (4)
O1—C2—C3—O20.3 (6)C18—O8—C12—C1199.4 (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—C41.8 (6)C10—C11—C12—O8163.6 (3)
O2—C3—C4—C5−178.4 (5)O6—C11—C12—C13162.6 (3)
C2—C3—C4—C51.0 (7)C10—C11—C12—C1346.8 (4)
C3—C4—C5—C6−2.8 (8)C9—O3—C13—C20−169.9 (3)
C4—C5—C6—C11.8 (8)C9—O3—C13—C1266.9 (4)
C2—C1—C6—C50.9 (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—C2064.9 (4)
C6—C1—C8—N1175.8 (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—O4179.7 (3)C9—O4—C14—C15176.9 (4)
C13—O3—C9—C10−65.7 (4)C11—O6—C16—O71.7 (8)
C14—O4—C9—O3−98.4 (4)C11—O6—C16—C17−177.7 (4)
C14—O4—C9—C10144.0 (4)C12—O8—C18—O93.0 (8)
C8—N1—C10—C11−100.9 (4)C12—O8—C18—C19−177.5 (4)
C8—N1—C10—C9137.6 (4)C21—O10—C20—C13−174.1 (4)
O3—C9—C10—N1174.0 (3)O3—C13—C20—O10−66.5 (4)
O4—C9—C10—N1−72.1 (4)C12—C13—C20—O1053.8 (5)
O3—C9—C10—C1153.4 (4)C20—O10—C21—O11−0.8 (7)
O4—C9—C10—C11167.3 (3)C20—O10—C21—C22178.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.625 (4)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2250).

References

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