Literature DB >> 24427038

1,2:1',2'-Di-O-iso-propyl-idenedi-furan-ose-C12 higher carbon sugar.

Qiurong Zhang1, Guangqiang Zhou1, Peng He1, Xuebin Chen1, Hongmin Liu1.   

Abstract

In the title compound, C18H28O8, the five-membered ring with one O atom attached to the ethyl substituent has a twisted conformation about the C-O bond. The adjacent cis-fused ring with two O atoms also has a twisted conformation about one of the C-O bonds. The dihedral angle between these rings (all atoms) is 59.05 (12)°. The five-membered ring linked to the ethynyl susbtituent is twisted about a C-C bond; the cis-fused adjacent ring is twisted about a C-O bond [dihedral angle between the rings (all atoms) = 71.78 (12)°]. Two intra-molecular O-H⋯O hydrogen bonds occur. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating [001] chains.

Entities:  

Year:  2013        PMID: 24427038      PMCID: PMC3884459          DOI: 10.1107/S1600536813021776

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


Related literature

For further synthetic details, see: Meyer & Jochims (1969 ▶). For background to higher-carbon sugars, see: Iwasa et al. (1978 ▶); Harada et al. (1981 ▶); Liu et al. (2006 ▶).

Experimental

Crystal data

C18H28O8 M = 372.40 Orthorhombic, a = 21.5802 (6) Å b = 15.3758 (4) Å c = 5.73626 (14) Å V = 1903.37 (8) Å3 Z = 4 Cu Kα radiation μ = 0.86 mm−1 T = 291 K 0.28 × 0.25 × 0.25 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.796, T max = 0.815 7406 measured reflections 3407 independent reflections 3079 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.099 S = 1.05 3407 reflections 262 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.18 e Å−3 Δρmin = −0.14 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813021776/hb7100sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021776/hb7100Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813021776/hb7100Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H28O8Dx = 1.300 Mg m3
Mr = 372.40Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P21212Cell parameters from 3059 reflections
a = 21.5802 (6) Åθ = 2.9–66.9°
b = 15.3758 (4) ŵ = 0.86 mm1
c = 5.73626 (14) ÅT = 291 K
V = 1903.37 (8) Å3Prism, colourless
Z = 40.28 × 0.25 × 0.25 mm
F(000) = 800
Agilent Xcalibur (Eos, Gemini) diffractometer3407 independent reflections
Radiation source: fine-focus sealed tube3079 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 0 pixels mm-1θmax = 67.1°, θmin = 3.5°
ω scansh = −24→25
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −18→17
Tmin = 0.796, Tmax = 0.815l = −4→6
7406 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099w = 1/[σ2(Fo2) + (0.0493P)2 + 0.1435P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3407 reflectionsΔρmax = 0.18 e Å3
262 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: 0.0064 (4)
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
O10.67974 (7)0.17289 (11)0.8701 (3)0.0581 (4)
O1'0.43970 (8)0.11163 (12)0.6552 (3)0.0671 (5)
O20.63054 (6)0.23737 (9)0.5648 (2)0.0418 (3)
O2'0.48323 (7)0.15439 (10)0.9957 (3)0.0589 (4)
O30.66664 (9)0.40182 (11)0.5529 (3)0.0587 (4)
O3'0.53146 (7)0.31495 (9)1.0267 (2)0.0484 (3)
O40.69581 (7)0.31202 (12)1.0229 (3)0.0659 (5)
O4'0.48425 (7)0.23484 (9)0.4771 (2)0.0520 (3)
C10.65181 (9)0.24742 (14)0.9636 (4)0.0496 (5)
H10.62600.23251.09840.060*
C1'0.49427 (10)0.15364 (13)0.5914 (4)0.0506 (5)
H1'0.51990.11550.49440.061*
C20.61210 (9)0.28500 (12)0.7651 (3)0.0402 (4)
C2'0.52685 (9)0.17335 (13)0.8211 (3)0.0436 (4)
H2'0.56440.13820.83920.052*
C30.63097 (9)0.38264 (13)0.7514 (3)0.0440 (4)
H3A0.59380.41920.75380.053*
C3'0.54226 (9)0.27154 (13)0.8134 (3)0.0398 (4)
C40.66772 (10)0.39550 (15)0.9764 (4)0.0522 (5)
H40.63860.40871.10250.063*
C4'0.49988 (9)0.30348 (13)0.6225 (3)0.0430 (4)
C50.71713 (12)0.4649 (2)0.9732 (5)0.0689 (7)
C5'0.47675 (10)0.38174 (15)0.5919 (4)0.0528 (5)
C60.69055 (13)0.55472 (19)0.9364 (6)0.0798 (8)
H6A0.65810.56491.04760.120*
H6B0.67410.55910.78140.120*
H6C0.72260.59730.95700.120*
C6'0.43255 (12)0.40709 (18)0.4031 (5)0.0679 (7)
H6'A0.40210.44630.46480.102*
H6'B0.41240.35600.34370.102*
H6'C0.45480.43520.27940.102*
C70.68335 (10)0.18190 (16)0.6219 (4)0.0544 (5)
C7'0.42493 (10)0.13080 (15)0.8936 (4)0.0561 (6)
C80.74382 (10)0.2237 (2)0.5493 (5)0.0704 (7)
H8A0.77760.18600.58900.106*
H8B0.74860.27820.62880.106*
H8C0.74360.23350.38400.106*
C8'0.40403 (12)0.04898 (16)1.0145 (6)0.0737 (8)
H8'A0.43640.00631.00710.111*
H8'B0.36760.02680.93900.111*
H8'C0.39480.06171.17460.111*
C90.67296 (12)0.09468 (15)0.5109 (5)0.0677 (7)
H9A0.63400.07150.56210.101*
H9B0.70570.05580.55520.101*
H9C0.67250.10100.34440.101*
C9'0.37906 (14)0.2033 (2)0.9154 (7)0.0895 (10)
H9'A0.34090.18680.84200.134*
H9'B0.39520.25450.84080.134*
H9'C0.37170.21531.07720.134*
H5'0.4875 (10)0.4262 (15)0.710 (4)0.053 (6)*
H3'0.5069 (12)0.2890 (17)1.101 (5)0.058 (7)*
H30.6667 (15)0.360 (2)0.465 (7)0.098 (11)*
H5A0.7420 (12)0.4587 (17)1.114 (5)0.062 (7)*
H5B0.7476 (13)0.4461 (19)0.861 (6)0.073 (9)*
U11U22U33U12U13U23
O10.0578 (8)0.0739 (10)0.0424 (8)0.0150 (7)−0.0015 (7)0.0186 (7)
O1'0.0701 (10)0.0719 (10)0.0592 (10)−0.0228 (8)−0.0003 (8)−0.0176 (9)
O20.0427 (6)0.0527 (7)0.0299 (6)0.0081 (5)−0.0010 (5)0.0049 (6)
O2'0.0650 (9)0.0692 (9)0.0425 (8)−0.0251 (7)0.0092 (7)−0.0090 (7)
O30.0817 (11)0.0624 (9)0.0319 (8)−0.0183 (8)0.0031 (8)0.0065 (7)
O3'0.0597 (8)0.0523 (7)0.0330 (7)−0.0070 (7)0.0067 (7)−0.0056 (6)
O40.0618 (9)0.0881 (11)0.0478 (9)−0.0116 (8)−0.0254 (8)0.0167 (9)
O4'0.0642 (8)0.0547 (8)0.0370 (7)0.0048 (6)−0.0076 (7)−0.0093 (6)
C10.0485 (10)0.0668 (12)0.0334 (10)−0.0007 (9)−0.0060 (8)0.0112 (9)
C1'0.0598 (11)0.0494 (10)0.0426 (11)−0.0011 (9)0.0042 (10)−0.0135 (8)
C20.0438 (9)0.0489 (10)0.0279 (8)−0.0001 (8)−0.0022 (8)0.0044 (7)
C2'0.0465 (10)0.0446 (10)0.0396 (10)−0.0009 (8)0.0041 (8)−0.0010 (8)
C30.0470 (10)0.0539 (10)0.0311 (9)−0.0067 (8)−0.0039 (8)0.0044 (9)
C3'0.0451 (10)0.0434 (9)0.0310 (9)−0.0013 (8)0.0014 (7)−0.0023 (8)
C40.0516 (11)0.0718 (13)0.0334 (10)−0.0135 (10)−0.0070 (9)0.0048 (10)
C4'0.0397 (9)0.0521 (11)0.0371 (9)−0.0013 (8)0.0010 (8)−0.0058 (8)
C50.0569 (13)0.1004 (19)0.0494 (14)−0.0283 (13)−0.0095 (12)−0.0036 (14)
C5'0.0528 (11)0.0533 (11)0.0525 (12)0.0079 (9)−0.0060 (10)−0.0030 (10)
C60.0788 (16)0.0816 (18)0.079 (2)−0.0332 (14)0.0106 (16)−0.0152 (15)
C6'0.0632 (13)0.0748 (16)0.0657 (16)0.0218 (12)−0.0114 (12)0.0000 (13)
C70.0501 (11)0.0722 (14)0.0408 (11)0.0182 (10)0.0019 (9)0.0149 (10)
C7'0.0547 (11)0.0557 (12)0.0579 (13)−0.0105 (10)0.0084 (11)−0.0128 (11)
C80.0471 (11)0.1052 (19)0.0590 (15)0.0145 (12)0.0032 (11)0.0242 (15)
C8'0.0734 (15)0.0600 (13)0.088 (2)−0.0209 (11)0.0128 (15)−0.0109 (14)
C90.0784 (15)0.0659 (14)0.0587 (15)0.0272 (12)0.0125 (13)0.0090 (12)
C9'0.0757 (17)0.0783 (18)0.114 (3)0.0070 (14)0.0291 (19)0.0034 (18)
O1—C11.401 (3)C4'—C5'1.315 (3)
O1—C71.433 (3)C5—C61.510 (4)
O1'—C1'1.392 (3)C5—H5A0.98 (3)
O1'—C7'1.434 (3)C5—H5B0.96 (3)
O2—C21.420 (2)C5'—C6'1.495 (3)
O2—C71.461 (2)C5'—H5'0.99 (2)
O2'—C2'1.405 (2)C6—H6A0.9600
O2'—C7'1.435 (3)C6—H6B0.9600
O3—C31.406 (2)C6—H6C0.9600
O3—H30.82 (4)C6'—H6'A0.9600
O3'—C3'1.413 (2)C6'—H6'B0.9600
O3'—H3'0.79 (3)C6'—H6'C0.9600
O4—C11.416 (3)C7—C91.501 (4)
O4—C41.444 (3)C7—C81.513 (3)
O4'—C4'1.387 (2)C7'—C9'1.496 (4)
O4'—C1'1.427 (3)C7'—C8'1.506 (4)
C1—C21.538 (3)C8—H8A0.9600
C1—H10.9800C8—H8B0.9600
C1'—C2'1.524 (3)C8—H8C0.9600
C1'—H1'0.9800C8'—H8'A0.9600
C2—C3'1.546 (3)C8'—H8'B0.9600
C2—C31.557 (3)C8'—H8'C0.9600
C2'—C3'1.547 (3)C9—H9A0.9600
C2'—H2'0.9800C9—H9B0.9600
C3—C41.528 (3)C9—H9C0.9600
C3—H3A0.9800C9'—H9'A0.9600
C3'—C4'1.509 (3)C9'—H9'B0.9600
C4—C51.508 (3)C9'—H9'C0.9600
C4—H40.9800
C1—O1—C7108.93 (17)C6—C5—H5A114.4 (16)
C1'—O1'—C7'110.09 (16)C4—C5—H5B106.1 (18)
C2—O2—C7109.79 (14)C6—C5—H5B116.1 (19)
C2'—O2'—C7'110.41 (16)H5A—C5—H5B99 (2)
C3—O3—H3109 (2)C4'—C5'—C6'125.3 (2)
C3'—O3'—H3'109.9 (19)C4'—C5'—H5'116.9 (14)
C1—O4—C4107.33 (15)C6'—C5'—H5'117.7 (14)
C4'—O4'—C1'110.65 (15)C5—C6—H6A109.5
O1—C1—O4112.17 (17)C5—C6—H6B109.5
O1—C1—C2105.30 (17)H6A—C6—H6B109.5
O4—C1—C2106.74 (16)C5—C6—H6C109.5
O1—C1—H1110.8H6A—C6—H6C109.5
O4—C1—H1110.8H6B—C6—H6C109.5
C2—C1—H1110.8C5'—C6'—H6'A109.5
O1'—C1'—O4'113.50 (18)C5'—C6'—H6'B109.5
O1'—C1'—C2'104.77 (17)H6'A—C6'—H6'B109.5
O4'—C1'—C2'107.05 (16)C5'—C6'—H6'C109.5
O1'—C1'—H1'110.4H6'A—C6'—H6'C109.5
O4'—C1'—H1'110.4H6'B—C6'—H6'C109.5
C2'—C1'—H1'110.4O1—C7—O2103.70 (17)
O2—C2—C1104.42 (15)O1—C7—C9109.1 (2)
O2—C2—C3'110.43 (15)O2—C7—C9108.06 (19)
C1—C2—C3'111.12 (15)O1—C7—C8111.2 (2)
O2—C2—C3112.52 (15)O2—C7—C8111.28 (18)
C1—C2—C3104.71 (15)C9—C7—C8113.0 (2)
C3'—C2—C3113.14 (16)O1'—C7'—O2'104.26 (17)
O2'—C2'—C1'105.43 (16)O1'—C7'—C9'112.3 (3)
O2'—C2'—C3'111.52 (16)O2'—C7'—C9'110.9 (2)
C1'—C2'—C3'105.59 (16)O1'—C7'—C8'109.5 (2)
O2'—C2'—H2'111.3O2'—C7'—C8'106.6 (2)
C1'—C2'—H2'111.3C9'—C7'—C8'112.7 (2)
C3'—C2'—H2'111.3C7—C8—H8A109.5
O3—C3—C4111.89 (16)C7—C8—H8B109.5
O3—C3—C2112.73 (17)H8A—C8—H8B109.5
C4—C3—C2102.58 (16)C7—C8—H8C109.5
O3—C3—H3A109.8H8A—C8—H8C109.5
C4—C3—H3A109.8H8B—C8—H8C109.5
C2—C3—H3A109.8C7'—C8'—H8'A109.5
O3'—C3'—C4'112.00 (15)C7'—C8'—H8'B109.5
O3'—C3'—C2104.63 (15)H8'A—C8'—H8'B109.5
C4'—C3'—C2114.66 (15)C7'—C8'—H8'C109.5
O3'—C3'—C2'113.63 (16)H8'A—C8'—H8'C109.5
C4'—C3'—C2'102.01 (15)H8'B—C8'—H8'C109.5
C2—C3'—C2'110.20 (15)C7—C9—H9A109.5
O4—C4—C5109.52 (19)C7—C9—H9B109.5
O4—C4—C3104.99 (17)H9A—C9—H9B109.5
C5—C4—C3116.62 (19)C7—C9—H9C109.5
O4—C4—H4108.5H9A—C9—H9C109.5
C5—C4—H4108.5H9B—C9—H9C109.5
C3—C4—H4108.5C7'—C9'—H9'A109.5
C5'—C4'—O4'121.58 (19)C7'—C9'—H9'B109.5
C5'—C4'—C3'128.69 (19)H9'A—C9'—H9'B109.5
O4'—C4'—C3'109.65 (16)C7'—C9'—H9'C109.5
C4—C5—C6112.3 (2)H9'A—C9'—H9'C109.5
C4—C5—H5A108.0 (16)H9'B—C9'—H9'C109.5
C7—O1—C1—O4−90.8 (2)C3—C2—C3'—C2'179.19 (16)
C7—O1—C1—C224.9 (2)O2'—C2'—C3'—O3'24.3 (2)
C4—O4—C1—O1145.01 (18)C1'—C2'—C3'—O3'138.29 (16)
C4—O4—C1—C230.2 (2)O2'—C2'—C3'—C4'−96.47 (18)
C7'—O1'—C1'—O4'−95.8 (2)C1'—C2'—C3'—C4'17.55 (19)
C7'—O1'—C1'—C2'20.6 (2)O2'—C2'—C3'—C2141.33 (16)
C4'—O4'—C1'—O1'107.62 (19)C1'—C2'—C3'—C2−104.65 (18)
C4'—O4'—C1'—C2'−7.5 (2)C1—O4—C4—C5−164.72 (19)
C7—O2—C2—C1−6.9 (2)C1—O4—C4—C3−38.8 (2)
C7—O2—C2—C3'−126.46 (17)O3—C3—C4—O4−90.6 (2)
C7—O2—C2—C3106.07 (18)C2—C3—C4—O430.5 (2)
O1—C1—C2—O2−10.73 (19)O3—C3—C4—C530.8 (3)
O4—C1—C2—O2108.66 (18)C2—C3—C4—C5151.9 (2)
O1—C1—C2—C3'108.34 (18)C1'—O4'—C4'—C5'−157.3 (2)
O4—C1—C2—C3'−132.27 (17)C1'—O4'—C4'—C3'19.9 (2)
O1—C1—C2—C3−129.19 (17)O3'—C3'—C4'—C5'32.0 (3)
O4—C1—C2—C3−9.8 (2)C2—C3'—C4'—C5'−87.0 (3)
C7'—O2'—C2'—C1'−4.3 (2)C2'—C3'—C4'—C5'153.9 (2)
C7'—O2'—C2'—C3'109.84 (19)O3'—C3'—C4'—O4'−144.87 (16)
O1'—C1'—C2'—O2'−9.9 (2)C2—C3'—C4'—O4'96.09 (19)
O4'—C1'—C2'—O2'110.96 (17)C2'—C3'—C4'—O4'−23.00 (19)
O1'—C1'—C2'—C3'−128.03 (17)O4—C4—C5—C6−177.3 (2)
O4'—C1'—C2'—C3'−7.2 (2)C3—C4—C5—C663.7 (3)
O2—C2—C3—O3−4.8 (2)O4'—C4'—C5'—C6'−0.5 (4)
C1—C2—C3—O3107.97 (18)C3'—C4'—C5'—C6'−177.0 (2)
C3'—C2—C3—O3−130.87 (17)C1—O1—C7—O2−28.9 (2)
O2—C2—C3—C4−125.35 (16)C1—O1—C7—C9−143.91 (18)
C1—C2—C3—C4−12.5 (2)C1—O1—C7—C890.7 (2)
C3'—C2—C3—C4108.61 (18)C2—O2—C7—O121.6 (2)
O2—C2—C3'—O3'174.56 (14)C2—O2—C7—C9137.29 (18)
C1—C2—C3'—O3'59.2 (2)C2—O2—C7—C8−98.0 (2)
C3—C2—C3'—O3'−58.30 (19)C1'—O1'—C7'—O2'−23.2 (3)
O2—C2—C3'—C4'−62.3 (2)C1'—O1'—C7'—C9'97.0 (2)
C1—C2—C3'—C4'−177.75 (17)C1'—O1'—C7'—C8'−137.0 (2)
C3—C2—C3'—C4'64.8 (2)C2'—O2'—C7'—O1'16.3 (2)
O2—C2—C3'—C2'52.04 (19)C2'—O2'—C7'—C9'−104.8 (2)
C1—C2—C3'—C2'−63.4 (2)C2'—O2'—C7'—C8'132.2 (2)
D—H···AD—HH···AD···AD—H···A
O3′—H3′···O4′i0.79 (3)2.36 (3)3.038 (2)144 (2)
O3′—H3′···O2′0.79 (3)2.22 (3)2.685 (2)119 (2)
O3—H3···O20.82 (4)2.11 (3)2.647 (2)122 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
O3′—H3′⋯O4′i 0.79 (3)2.36 (3)3.038 (2)144 (2)
O3′—H3′⋯O2′0.79 (3)2.22 (3)2.685 (2)119 (2)
O3—H3⋯O20.82 (4)2.11 (3)2.647 (2)122 (3)

Symmetry code: (i) .

  3 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.  [Formation and reactions of 5-desoxy-4-hexenofuranos-3-ulosen, a new class of alpha-beta-unsaturated monosaccharide ketone].

Authors:  W Meyer zu Reckendorf; J C Jochims
Journal:  Chem Ber       Date:  1969

3.  Taxonomic study and fermentation of producing organism and antimicrobial activity of mildiomycin.

Authors:  T Iwasa; K Suetomi; T Kusaka
Journal:  J Antibiot (Tokyo)       Date:  1978-06       Impact factor: 2.649

  3 in total

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