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

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ISSN: 2056-9890

4-(Dimeth­­oxy­meth­yl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-gluco­pyran­oside

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
*Correspondence e-mail: Helder.Marques@wits.ac.za

(Received 22 February 2012; accepted 14 March 2012; online 28 March 2012)

The enanti­omerically pure title compound, C23H30O12, crystallizes in the chiral space group P212121. The O-acetyl­ated-glucopyran­oside moiety adopts a chair conformation. Numerous C—H⋯O inter­actions as well as a C—H⋯π inter­action are present in the crystal structure.

Related literature

For similar compounds, see: Bin et al. (2008[Bin, Y., Zhao, F., Zhang, F. & Wang, R.-J. (2008). Acta Cryst. E64, o63.]); Ansari et al. (2006[Ansari, F. L., Sultana, S., Corrente, A. M. & Parvez, M. (2006). Acta Cryst. E62, o3139-o3141.]). For the use of sugars as water-solubilizing agents in macrocycle chemistry, see: Sol et al. (1997[Sol, V., Blais, J. C., Bolbach, G., Carré, V., Granet, R., Guilloton, M., Spiro, M. & Krausz, P. (1997). Tetrahedron Lett. 38, 6391-6394.]); Maillard et al. (1993[Maillard, P., Guerquin-Kern, J.-L., Huel, C. & Momenteau, M. (1993). J. Org. Chem. 58, 2774-2780.]); Oulmi et al. (1995[Oulmi, D., Maillard, P., Guerquin-Kern, J.-L., Huel, C. & Momenteau, M. (1995). J. Org. Chem. 60, 1554-1564.]). For the role of sugars in biological systems, especially proteins, see: Floyd et al. (2009[Floyd, N., Vijayakrishnan, B., Koeppe, J. R. & Davis, B. G. (2009). Angew. Chem. Int. Ed. 48, 7798-7802.]).

[Scheme 1]

Experimental

Crystal data
  • C23H30O12

  • Mr = 498.47

  • Orthorhombic, P 21 21 21

  • a = 7.9004 (2) Å

  • b = 10.9961 (3) Å

  • c = 29.2289 (8) Å

  • V = 2539.22 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 173 K

  • 0.45 × 0.32 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 13406 measured reflections

  • 3493 independent reflections

  • 2644 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.102

  • S = 0.97

  • 3493 reflections

  • 322 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O11i 1.00 2.44 3.347 (3) 151
C12—H12⋯O4ii 0.95 2.45 3.321 (3) 152
C19—H19A⋯O3iii 0.98 2.54 3.510 (3) 171
C19—H19C⋯O8iv 0.98 2.49 3.414 (3) 157
C21—H21C⋯O10iv 0.98 2.29 3.252 (4) 168
C23—H23CCgv 0.98 2.71 3.615 (4) 153
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iv) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (v) x, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Glycosylation is common in nature, with a large proportion of all proteins bearing sugar residues (Floyd et al., 2009). The title compound was synthesized as a precursor to a biomimetic model for vitamin B12a (aquacobalamin) as sugars can play a useful role in the solubilizing of large organic systems, such as glycosylated porphyrins (Sol et al., 1997; Maillard et al., 1993; Oulmi et al., 1995).

Related literature top

For similar compounds, see: Bin et al. (2008); Ansari et al. (2006). For the use of sugars as water-solubilizing agents in macrocycle chemistry, see: Sol et al. (1997); Maillard et al. (1993); Oulmi et al. (1995). For the role of sugars in biological systems, especially proteins, see: Floyd et al. (2009).

Experimental top

The title compound was synthesized from p-hydroxybenzaldehyde and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of NaOH. The product was purified by column chromatography and recrystallized from acidified methanol to yield colourless plate-like crystals.

Refinement top

All H atoms were positioned geometrically, and allowed to ride on their parent atoms. Hydrogen bond lengths were set as follows: C—H = 0.95 Å (Aromatic C—H), 1.00 Å (Methine C—H) 0.99 Å (CH2) or 0.98 Å (CH3). Isotropic displacement parameters for these atoms were set as 1.2 times Ueq of the parent atom for CH and CH2, and 1.5 times Ueq of the parent atom for CH3.

Structure description top

Glycosylation is common in nature, with a large proportion of all proteins bearing sugar residues (Floyd et al., 2009). The title compound was synthesized as a precursor to a biomimetic model for vitamin B12a (aquacobalamin) as sugars can play a useful role in the solubilizing of large organic systems, such as glycosylated porphyrins (Sol et al., 1997; Maillard et al., 1993; Oulmi et al., 1995).

For similar compounds, see: Bin et al. (2008); Ansari et al. (2006). For the use of sugars as water-solubilizing agents in macrocycle chemistry, see: Sol et al. (1997); Maillard et al. (1993); Oulmi et al. (1995). For the role of sugars in biological systems, especially proteins, see: Floyd et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Weak hydrogen bonding in the strucuture of (I). Four of the five C—H···O interactions listed in Table 1 are shown, while the location of the C—H···π interactions is indicated with a #.
4-(Dimethoxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside top
Crystal data top
C23H30O12F(000) = 1056
Mr = 498.47Dx = 1.304 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3488 reflections
a = 7.9004 (2) Åθ = 2.3–24.0°
b = 10.9961 (3) ŵ = 0.11 mm1
c = 29.2289 (8) ÅT = 173 K
V = 2539.22 (12) Å3Plate, colourless
Z = 40.45 × 0.32 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
2644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
φ and ω scansh = 1010
13406 measured reflectionsk = 1014
3493 independent reflectionsl = 3837
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0567P)2]
where P = (Fo2 + 2Fc2)/3
3493 reflections(Δ/σ)max = 0.001
322 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C23H30O12V = 2539.22 (12) Å3
Mr = 498.47Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.9004 (2) ŵ = 0.11 mm1
b = 10.9961 (3) ÅT = 173 K
c = 29.2289 (8) Å0.45 × 0.32 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
2644 reflections with I > 2σ(I)
13406 measured reflectionsRint = 0.053
3493 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.97Δρmax = 0.25 e Å3
3493 reflectionsΔρmin = 0.20 e Å3
322 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
C10.0801 (3)0.3057 (2)0.12632 (8)0.0238 (5)
H10.01130.24570.10860.029*
C20.2410 (3)0.3384 (2)0.10042 (8)0.0219 (5)
H20.31640.39050.11970.026*
C30.1944 (3)0.4037 (2)0.05649 (8)0.0225 (5)
H30.13730.34610.03500.027*
C40.0790 (3)0.5105 (2)0.06664 (8)0.0236 (5)
H40.14200.57530.08360.028*
C50.0749 (3)0.4686 (2)0.09422 (8)0.0254 (5)
H50.13990.40770.07590.031*
C60.1907 (3)0.5704 (2)0.10783 (9)0.0313 (6)
H6A0.23580.61130.08020.038*
H6B0.28730.53810.12570.038*
C70.0063 (3)0.1934 (2)0.19310 (8)0.0266 (5)
C80.0622 (4)0.1381 (2)0.23282 (9)0.0355 (7)
H80.17760.14370.24170.043*
C90.0526 (4)0.0745 (3)0.25957 (9)0.0389 (7)
H90.01490.03600.28680.047*
C100.2229 (4)0.0663 (2)0.24709 (9)0.0349 (6)
C110.2725 (4)0.1186 (2)0.20664 (10)0.0353 (6)
H110.38650.11000.19680.042*
C120.1597 (4)0.1839 (2)0.17970 (9)0.0339 (6)
H120.19710.22170.15230.041*
C130.3436 (4)0.0023 (3)0.27751 (10)0.0439 (7)
H130.30080.08750.28040.053*
C140.4138 (6)0.1676 (3)0.32407 (12)0.0660 (11)
H14A0.33710.22050.30680.099*
H14B0.41810.19440.35600.099*
H14C0.52740.17180.31070.099*
C150.6115 (6)0.0935 (3)0.27581 (13)0.0679 (11)
H15A0.55870.17410.27460.102*
H15B0.71820.09500.25870.102*
H15C0.63400.07160.30770.102*
C160.4919 (4)0.2178 (2)0.09375 (8)0.0284 (6)
C170.5515 (4)0.0911 (2)0.08455 (10)0.0428 (7)
H17A0.67520.08820.08650.064*
H17B0.51540.06620.05390.064*
H17C0.50270.03570.10730.064*
C180.4204 (3)0.3879 (2)0.00160 (8)0.0268 (5)
C190.5757 (4)0.4516 (2)0.01518 (10)0.0395 (7)
H19A0.63240.40090.03810.059*
H19B0.65270.46600.01060.059*
H19C0.54380.52960.02890.059*
C200.0206 (4)0.6785 (2)0.01657 (9)0.0329 (6)
C210.0371 (5)0.7100 (3)0.03023 (10)0.0481 (8)
H21A0.06920.79600.03130.072*
H21B0.13500.65970.03830.072*
H21C0.05480.69510.05200.072*
C220.1382 (4)0.7733 (3)0.13249 (11)0.0464 (8)
C230.0184 (5)0.8508 (3)0.15844 (13)0.0651 (11)
H23A0.07820.87160.13890.098*
H23B0.02160.80660.18550.098*
H23C0.07590.92550.16810.098*
O10.0151 (2)0.41192 (14)0.13529 (5)0.0264 (4)
O20.1293 (2)0.25639 (15)0.16843 (5)0.0283 (4)
O30.3219 (2)0.22387 (14)0.09025 (5)0.0257 (4)
O40.5794 (3)0.30351 (17)0.10281 (7)0.0401 (5)
O50.3456 (2)0.45309 (14)0.03546 (5)0.0249 (4)
O60.3683 (3)0.29251 (16)0.01228 (6)0.0401 (5)
O70.0199 (2)0.55613 (14)0.02296 (5)0.0280 (4)
O80.0625 (3)0.74887 (16)0.04572 (7)0.0538 (6)
O90.0958 (3)0.65541 (15)0.13508 (6)0.0370 (5)
O100.2594 (4)0.8089 (2)0.11206 (10)0.0741 (8)
O110.3548 (3)0.0473 (2)0.32214 (7)0.0566 (6)
O120.5013 (3)0.00697 (19)0.25616 (7)0.0510 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0264 (13)0.0235 (11)0.0216 (12)0.0017 (11)0.0011 (11)0.0001 (9)
C20.0204 (12)0.0216 (11)0.0235 (12)0.0004 (10)0.0008 (10)0.0046 (9)
C30.0225 (12)0.0197 (11)0.0253 (12)0.0027 (10)0.0022 (11)0.0003 (9)
C40.0265 (13)0.0213 (11)0.0230 (12)0.0000 (11)0.0013 (11)0.0005 (9)
C50.0247 (13)0.0257 (11)0.0259 (12)0.0010 (10)0.0008 (11)0.0006 (9)
C60.0295 (15)0.0337 (13)0.0309 (14)0.0078 (12)0.0020 (12)0.0011 (11)
C70.0297 (14)0.0253 (11)0.0248 (12)0.0009 (11)0.0044 (11)0.0003 (10)
C80.0360 (16)0.0430 (15)0.0276 (14)0.0015 (13)0.0046 (13)0.0055 (11)
C90.046 (2)0.0437 (16)0.0270 (14)0.0015 (14)0.0033 (13)0.0115 (12)
C100.0400 (17)0.0347 (14)0.0299 (14)0.0026 (13)0.0057 (13)0.0056 (11)
C110.0287 (14)0.0391 (14)0.0382 (16)0.0037 (12)0.0046 (13)0.0074 (12)
C120.0332 (16)0.0394 (14)0.0290 (14)0.0050 (13)0.0043 (12)0.0097 (11)
C130.0493 (19)0.0431 (16)0.0393 (17)0.0007 (15)0.0052 (15)0.0149 (13)
C140.074 (3)0.065 (2)0.059 (2)0.012 (2)0.029 (2)0.0096 (17)
C150.076 (3)0.062 (2)0.066 (2)0.023 (2)0.017 (2)0.0088 (18)
C160.0278 (14)0.0338 (13)0.0237 (13)0.0067 (12)0.0010 (11)0.0011 (10)
C170.0434 (18)0.0376 (14)0.0474 (17)0.0151 (14)0.0015 (15)0.0033 (13)
C180.0295 (13)0.0244 (11)0.0265 (13)0.0036 (11)0.0040 (12)0.0005 (9)
C190.0407 (16)0.0323 (13)0.0455 (16)0.0004 (13)0.0207 (15)0.0010 (12)
C200.0327 (15)0.0252 (12)0.0409 (15)0.0023 (11)0.0092 (13)0.0066 (11)
C210.067 (2)0.0324 (14)0.0452 (17)0.0067 (15)0.0005 (17)0.0119 (13)
C220.052 (2)0.0367 (15)0.0510 (18)0.0163 (15)0.0011 (17)0.0032 (14)
C230.077 (3)0.0392 (16)0.079 (3)0.0126 (19)0.018 (2)0.0202 (17)
O10.0287 (10)0.0289 (8)0.0217 (8)0.0038 (7)0.0024 (8)0.0015 (7)
O20.0272 (10)0.0340 (9)0.0236 (9)0.0010 (8)0.0008 (8)0.0046 (7)
O30.0257 (10)0.0223 (8)0.0291 (9)0.0039 (7)0.0011 (8)0.0021 (7)
O40.0261 (10)0.0378 (10)0.0564 (13)0.0012 (9)0.0027 (10)0.0023 (9)
O50.0251 (9)0.0213 (7)0.0283 (9)0.0018 (7)0.0070 (8)0.0022 (7)
O60.0433 (12)0.0332 (10)0.0439 (11)0.0046 (9)0.0128 (10)0.0138 (8)
O70.0336 (10)0.0221 (8)0.0283 (9)0.0029 (7)0.0002 (8)0.0025 (7)
O80.0837 (18)0.0234 (9)0.0542 (13)0.0053 (11)0.0061 (13)0.0034 (9)
O90.0466 (12)0.0302 (9)0.0343 (10)0.0134 (9)0.0038 (10)0.0072 (7)
O100.0699 (18)0.0433 (12)0.109 (2)0.0250 (13)0.0303 (16)0.0047 (13)
O110.0628 (16)0.0706 (15)0.0365 (12)0.0076 (14)0.0116 (11)0.0106 (11)
O120.0476 (13)0.0543 (13)0.0511 (13)0.0148 (12)0.0048 (11)0.0135 (10)
Geometric parameters (Å, º) top
C1—O21.400 (3)C13—H131.0000
C1—O11.414 (3)C14—O111.404 (4)
C1—C21.522 (3)C14—H14A0.9800
C1—H11.0000C14—H14B0.9800
C2—O31.444 (3)C14—H14C0.9800
C2—C31.516 (3)C15—O121.412 (4)
C2—H21.0000C15—H15A0.9800
C3—O51.449 (3)C15—H15B0.9800
C3—C41.516 (3)C15—H15C0.9800
C3—H31.0000C16—O41.198 (3)
C4—O71.449 (3)C16—O31.348 (3)
C4—C51.530 (3)C16—C171.495 (3)
C4—H41.0000C17—H17A0.9800
C5—O11.433 (3)C17—H17B0.9800
C5—C61.500 (3)C17—H17C0.9800
C5—H51.0000C18—O61.198 (3)
C6—O91.439 (3)C18—O51.357 (3)
C6—H6A0.9900C18—C191.495 (4)
C6—H6B0.9900C19—H19A0.9800
C7—C121.373 (4)C19—H19B0.9800
C7—C81.383 (4)C19—H19C0.9800
C7—O21.394 (3)C20—O81.198 (3)
C8—C91.387 (4)C20—O71.359 (3)
C8—H80.9500C20—C211.483 (4)
C9—C101.397 (4)C21—H21A0.9800
C9—H90.9500C21—H21B0.9800
C10—C111.372 (4)C21—H21C0.9800
C10—C131.506 (4)C22—O101.195 (4)
C11—C121.390 (4)C22—O91.341 (3)
C11—H110.9500C22—C231.482 (5)
C12—H120.9500C23—H23A0.9800
C13—O121.395 (4)C23—H23B0.9800
C13—O111.417 (4)C23—H23C0.9800
O2—C1—O1107.73 (17)O11—C13—H13107.8
O2—C1—C2107.29 (19)C10—C13—H13107.8
O1—C1—C2109.94 (18)O11—C14—H14A109.5
O2—C1—H1110.6O11—C14—H14B109.5
O1—C1—H1110.6H14A—C14—H14B109.5
C2—C1—H1110.6O11—C14—H14C109.5
O3—C2—C3110.26 (18)H14A—C14—H14C109.5
O3—C2—C1105.40 (17)H14B—C14—H14C109.5
C3—C2—C1109.29 (19)O12—C15—H15A109.5
O3—C2—H2110.6O12—C15—H15B109.5
C3—C2—H2110.6H15A—C15—H15B109.5
C1—C2—H2110.6O12—C15—H15C109.5
O5—C3—C4106.76 (17)H15A—C15—H15C109.5
O5—C3—C2109.66 (19)H15B—C15—H15C109.5
C4—C3—C2110.31 (18)O4—C16—O3123.5 (2)
O5—C3—H3110.0O4—C16—C17126.2 (3)
C4—C3—H3110.0O3—C16—C17110.2 (2)
C2—C3—H3110.0C16—C17—H17A109.5
O7—C4—C3106.83 (17)C16—C17—H17B109.5
O7—C4—C5108.2 (2)H17A—C17—H17B109.5
C3—C4—C5110.31 (18)C16—C17—H17C109.5
O7—C4—H4110.5H17A—C17—H17C109.5
C3—C4—H4110.5H17B—C17—H17C109.5
C5—C4—H4110.5O6—C18—O5124.0 (2)
O1—C5—C6107.67 (18)O6—C18—C19125.5 (2)
O1—C5—C4108.10 (19)O5—C18—C19110.4 (2)
C6—C5—C4113.56 (19)C18—C19—H19A109.5
O1—C5—H5109.1C18—C19—H19B109.5
C6—C5—H5109.1H19A—C19—H19B109.5
C4—C5—H5109.1C18—C19—H19C109.5
O9—C6—C5108.3 (2)H19A—C19—H19C109.5
O9—C6—H6A110.0H19B—C19—H19C109.5
C5—C6—H6A110.0O8—C20—O7122.9 (2)
O9—C6—H6B110.0O8—C20—C21126.2 (2)
C5—C6—H6B110.0O7—C20—C21110.9 (2)
H6A—C6—H6B108.4C20—C21—H21A109.5
C12—C7—C8120.7 (2)C20—C21—H21B109.5
C12—C7—O2123.8 (2)H21A—C21—H21B109.5
C8—C7—O2115.5 (2)C20—C21—H21C109.5
C7—C8—C9119.1 (3)H21A—C21—H21C109.5
C7—C8—H8120.5H21B—C21—H21C109.5
C9—C8—H8120.5O10—C22—O9123.0 (3)
C8—C9—C10121.0 (2)O10—C22—C23125.4 (3)
C8—C9—H9119.5O9—C22—C23111.6 (3)
C10—C9—H9119.5C22—C23—H23A109.5
C11—C10—C9118.2 (3)C22—C23—H23B109.5
C11—C10—C13122.5 (3)H23A—C23—H23B109.5
C9—C10—C13119.2 (2)C22—C23—H23C109.5
C10—C11—C12121.5 (3)H23A—C23—H23C109.5
C10—C11—H11119.3H23B—C23—H23C109.5
C12—C11—H11119.3C1—O1—C5112.28 (16)
C7—C12—C11119.4 (2)C7—O2—C1117.00 (19)
C7—C12—H12120.3C16—O3—C2117.93 (19)
C11—C12—H12120.3C18—O5—C3118.07 (18)
O12—C13—O11111.7 (3)C20—O7—C4117.55 (19)
O12—C13—C10108.7 (2)C22—O9—C6117.8 (2)
O11—C13—C10113.0 (2)C14—O11—C13114.9 (2)
O12—C13—H13107.8C13—O12—C15113.2 (3)
O2—C1—C2—O367.0 (2)C11—C10—C13—O11121.4 (3)
O1—C1—C2—O3176.06 (17)C9—C10—C13—O1160.5 (4)
O2—C1—C2—C3174.46 (17)O2—C1—O1—C5178.82 (18)
O1—C1—C2—C357.6 (2)C2—C1—O1—C564.6 (2)
O3—C2—C3—O574.1 (2)C6—C5—O1—C1173.20 (19)
C1—C2—C3—O5170.47 (17)C4—C5—O1—C163.7 (2)
O3—C2—C3—C4168.59 (18)C12—C7—O2—C14.1 (3)
C1—C2—C3—C453.2 (2)C8—C7—O2—C1175.4 (2)
O5—C3—C4—O769.5 (2)O1—C1—O2—C776.8 (2)
C2—C3—C4—O7171.43 (18)C2—C1—O2—C7164.91 (18)
O5—C3—C4—C5173.12 (18)O4—C16—O3—C23.5 (4)
C2—C3—C4—C554.0 (3)C17—C16—O3—C2176.82 (19)
O7—C4—C5—O1174.03 (16)C3—C2—O3—C16101.6 (2)
C3—C4—C5—O157.5 (2)C1—C2—O3—C16140.5 (2)
O7—C4—C5—C666.6 (2)O6—C18—O5—C30.7 (3)
C3—C4—C5—C6176.9 (2)C19—C18—O5—C3178.8 (2)
O1—C5—C6—O960.3 (2)C4—C3—O5—C18143.3 (2)
C4—C5—C6—O959.4 (3)C2—C3—O5—C1897.2 (2)
C12—C7—C8—C91.2 (4)O8—C20—O7—C42.4 (4)
O2—C7—C8—C9179.4 (2)C21—C20—O7—C4177.8 (2)
C7—C8—C9—C100.4 (4)C3—C4—O7—C20135.4 (2)
C8—C9—C10—C112.7 (4)C5—C4—O7—C20105.8 (2)
C8—C9—C10—C13179.2 (3)O10—C22—O9—C66.9 (5)
C9—C10—C11—C123.5 (4)C23—C22—O9—C6173.9 (3)
C13—C10—C11—C12178.5 (3)C5—C6—O9—C22148.1 (2)
C8—C7—C12—C110.4 (4)O12—C13—O11—C1461.7 (3)
O2—C7—C12—C11179.8 (2)C10—C13—O11—C1461.2 (4)
C10—C11—C12—C72.0 (4)O11—C13—O12—C1569.5 (3)
C11—C10—C13—O123.2 (4)C10—C13—O12—C15165.2 (3)
C9—C10—C13—O12174.9 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O11i1.002.443.347 (3)151
C12—H12···O4ii0.952.453.321 (3)152
C19—H19A···O3iii0.982.543.510 (3)171
C19—H19C···O8iv0.982.493.414 (3)157
C21—H21C···O10iv0.982.293.252 (4)168
C23—H23C···Cgv0.982.713.615 (4)153
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x1, y, z; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y+3/2, z; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC23H30O12
Mr498.47
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)7.9004 (2), 10.9961 (3), 29.2289 (8)
V3)2539.22 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.45 × 0.32 × 0.10
Data collection
DiffractometerBruker APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13406, 3493, 2644
Rint0.053
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.102, 0.97
No. of reflections3493
No. of parameters322
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O11i1.002.443.347 (3)151
C12—H12···O4ii0.952.453.321 (3)152
C19—H19A···O3iii0.982.543.510 (3)171
C19—H19C···O8iv0.982.493.414 (3)157
C21—H21C···O10iv0.982.293.252 (4)168
C23—H23C···Cgv0.982.713.615 (4)153
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x1, y, z; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y+3/2, z; (v) x, y+1, z.
 

Acknowledgements

This work was supported by the National Research Foundation, Pretoria (NRF, GUN 2053652), the South African Research Chairs Initiative and the University of the Witwatersrand.

References

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