Literature DB >> 22606142

4-(Dimeth-oxy-meth-yl)phenyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyran-oside.

Caitlin F Zipp1, Manuel Fernandes, Helder M Marques, Joseph P Michael.   

Abstract

The enanti-omerically pure title compound, C(23)H(30)O(12), crystallizes in the chiral space group P2(1)2(1)2(1). The O-acetyl-ated-glucopyran-oside moiety adopts a chair conformation. Numerous C-H⋯O inter-actions as well as a C-H⋯π inter-action are present in the crystal structure.

Entities:  

Year:  2012        PMID: 22606142      PMCID: PMC3344139          DOI: 10.1107/S160053681201121X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

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

Crystal data

C23H30O12 M = 498.47 Orthorhombic, 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) R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 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 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201121X/mw2057sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201121X/mw2057Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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
Bruker APEXII CCD diffractometer2644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
φ and ω scansh = −10→10
13406 measured reflectionsk = −10→14
3493 independent reflectionsl = −38→37
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 = 0.97w = 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
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.
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*
C5−0.0749 (3)0.4686 (2)0.09422 (8)0.0254 (5)
H5−0.13990.40770.07590.031*
C6−0.1907 (3)0.5704 (2)0.10783 (9)0.0313 (6)
H6A−0.23580.61130.08020.038*
H6B−0.28730.53810.12570.038*
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*
C9−0.0526 (4)0.0745 (3)0.25957 (9)0.0389 (7)
H9−0.01490.03600.28680.047*
C10−0.2229 (4)0.0663 (2)0.24709 (9)0.0349 (6)
C11−0.2725 (4)0.1186 (2)0.20664 (10)0.0353 (6)
H11−0.38650.11000.19680.042*
C12−0.1597 (4)0.1839 (2)0.17970 (9)0.0339 (6)
H12−0.19710.22170.15230.041*
C13−0.3436 (4)−0.0023 (3)0.27751 (10)0.0439 (7)
H13−0.3008−0.08750.28040.053*
C14−0.4138 (6)0.1676 (3)0.32407 (12)0.0660 (11)
H14A−0.33710.22050.30680.099*
H14B−0.41810.19440.35600.099*
H14C−0.52740.17180.31070.099*
C15−0.6115 (6)−0.0935 (3)0.27581 (13)0.0679 (11)
H15A−0.5587−0.17410.27460.102*
H15B−0.7182−0.09500.25870.102*
H15C−0.6340−0.07160.30770.102*
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)
H19A0.63240.4009−0.03810.059*
H19B0.65270.46600.01060.059*
H19C0.54380.5296−0.02890.059*
C200.0206 (4)0.6785 (2)0.01657 (9)0.0329 (6)
C21−0.0371 (5)0.7100 (3)−0.03023 (10)0.0481 (8)
H21A−0.06920.7960−0.03130.072*
H21B−0.13500.6597−0.03830.072*
H21C0.05480.6951−0.05200.072*
C22−0.1382 (4)0.7733 (3)0.13249 (11)0.0464 (8)
C23−0.0184 (5)0.8508 (3)0.15844 (13)0.0651 (11)
H23A0.07820.87160.13890.098*
H23B0.02160.80660.18550.098*
H23C−0.07590.92550.16810.098*
O1−0.0151 (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)
O9−0.0958 (3)0.65541 (15)0.13508 (6)0.0370 (5)
O10−0.2594 (4)0.8089 (2)0.11206 (10)0.0741 (8)
O11−0.3548 (3)0.0473 (2)0.32214 (7)0.0566 (6)
O12−0.5013 (3)−0.00697 (19)0.25616 (7)0.0510 (6)
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)
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—O11−121.4 (3)
O1—C1—C2—O3−176.06 (17)C9—C10—C13—O1160.5 (4)
O2—C1—C2—C3−174.46 (17)O2—C1—O1—C5−178.82 (18)
O1—C1—C2—C3−57.6 (2)C2—C1—O1—C564.6 (2)
O3—C2—C3—O5−74.1 (2)C6—C5—O1—C1173.20 (19)
C1—C2—C3—O5170.47 (17)C4—C5—O1—C1−63.7 (2)
O3—C2—C3—C4168.59 (18)C12—C7—O2—C1−4.1 (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—O7−171.43 (18)C2—C1—O2—C7−164.91 (18)
O5—C3—C4—C5−173.12 (18)O4—C16—O3—C2−3.5 (4)
C2—C3—C4—C5−54.0 (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—C16−140.5 (2)
O7—C4—C5—C6−66.6 (2)O6—C18—O5—C30.7 (3)
C3—C4—C5—C6176.9 (2)C19—C18—O5—C3−178.8 (2)
O1—C5—C6—O960.3 (2)C4—C3—O5—C18−143.3 (2)
C4—C5—C6—O9−59.4 (3)C2—C3—O5—C1897.2 (2)
C12—C7—C8—C9−1.2 (4)O8—C20—O7—C4−2.4 (4)
O2—C7—C8—C9179.4 (2)C21—C20—O7—C4177.8 (2)
C7—C8—C9—C10−0.4 (4)C3—C4—O7—C20−135.4 (2)
C8—C9—C10—C112.7 (4)C5—C4—O7—C20105.8 (2)
C8—C9—C10—C13−179.2 (3)O10—C22—O9—C66.9 (5)
C9—C10—C11—C12−3.5 (4)C23—C22—O9—C6−173.9 (3)
C13—C10—C11—C12178.5 (3)C5—C6—O9—C22148.1 (2)
C8—C7—C12—C110.4 (4)O12—C13—O11—C14−61.7 (3)
O2—C7—C12—C11179.8 (2)C10—C13—O11—C1461.2 (4)
C10—C11—C12—C72.0 (4)O11—C13—O12—C15−69.5 (3)
C11—C10—C13—O123.2 (4)C10—C13—O12—C15165.2 (3)
C9—C10—C13—O12−174.9 (3)
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
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯AD—HH⋯ADAD—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—H23CCgv0.982.713.615 (4)153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Thiyl glycosylation of olefinic proteins: S-linked glycoconjugate synthesis.

Authors:  Nicola Floyd; Balakumar Vijayakrishnan; Julia R Koeppe; Benjamin G Davis
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  3,4-Dicyano-phenyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyran-oside.

Authors:  Yuejing Bin; Fuqun Zhao; Fushi Zhang; Ru-Ji Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2007-12-06

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total

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