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The six-membered ring of the title compound, C
11H
20O
6, adopts the chair conformation, with the 4-
O-pivaloyl group in an equatorial position. Two vicinal hydroxyl groups of each molecule form four hydrogen bonds of the O—H
O type in a one-dimensional chain running along the
b axis.
Supporting information
CCDC reference: 613627
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.159
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.10 Ratio
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C8
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.08
From the CIF: _reflns_number_total 1728
Count of symmetry unique reflns 1745
Completeness (_total/calc) 99.03%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: SHELXL97.
Methyl 4-
O-pivaloyl-
β-
D-xylopyranoside
top
Crystal data top
C11H20O6 | F(000) = 536 |
Mr = 248.27 | Dx = 1.225 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1582 reflections |
a = 6.1419 (12) Å | θ = 2.9–21.3° |
b = 7.0145 (13) Å | µ = 0.10 mm−1 |
c = 31.244 (4) Å | T = 295 K |
V = 1346.1 (4) Å3 | Prism, colourless |
Z = 4 | 0.75 × 0.40 × 0.40 mm |
Data collection top
Oxford Diffraction Xcalibur3 CCD diffractometer | 1254 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 27.1°, θmin = 4.4° |
ω scans | h = −6→7 |
5650 measured reflections | k = −8→6 |
1728 independent reflections | l = −39→39 |
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)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0991P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
1728 reflections | Δρmax = 0.18 e Å−3 |
167 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.093 (16) |
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 | x | y | z | Uiso*/Ueq | |
H21 | −0.051 (8) | 0.435 (6) | 0.2559 (13) | 0.110 (14)* | |
H22 | −0.192 (7) | 0.214 (6) | 0.2102 (14) | 0.097 (14)* | |
O2 | 0.2557 (3) | 0.8154 (3) | 0.20758 (6) | 0.0652 (6) | |
O1 | 0.2196 (4) | 0.6765 (3) | 0.14287 (6) | 0.0763 (7) | |
O3 | 0.0735 (4) | 0.5020 (3) | 0.24780 (5) | 0.0628 (6) | |
O5 | −0.0244 (4) | 0.2282 (3) | 0.10837 (6) | 0.0730 (7) | |
O4 | −0.2126 (4) | 0.2836 (3) | 0.19122 (7) | 0.0728 (7) | |
C3 | −0.0080 (5) | 0.3600 (4) | 0.17876 (7) | 0.0557 (7) | |
H3 | 0.1064 | 0.2662 | 0.1847 | 0.067* | |
C1 | 0.2388 (5) | 0.6385 (4) | 0.18711 (8) | 0.0584 (7) | |
H1 | 0.3684 | 0.5610 | 0.1928 | 0.070* | |
C4 | −0.0100 (6) | 0.4049 (4) | 0.13122 (8) | 0.0620 (8) | |
H4 | −0.1354 | 0.4856 | 0.1243 | 0.074* | |
C2 | 0.0385 (4) | 0.5402 (4) | 0.20356 (7) | 0.0512 (6) | |
H2 | −0.0859 | 0.6266 | 0.2007 | 0.061* | |
C5 | 0.1966 (7) | 0.5040 (5) | 0.11895 (9) | 0.0807 (10) | |
H5B | 0.3198 | 0.4212 | 0.1245 | 0.097* | |
H5A | 0.1945 | 0.5329 | 0.0886 | 0.097* | |
O6 | −0.2524 (7) | 0.3581 (4) | 0.06194 (9) | 0.1228 (14) | |
C7 | −0.1585 (7) | 0.2206 (5) | 0.07470 (9) | 0.0731 (9) | |
C6 | 0.4557 (7) | 0.9130 (6) | 0.20168 (16) | 0.1071 (14) | |
H6B | 0.5740 | 0.8323 | 0.2104 | 0.161* | |
H6C | 0.4562 | 1.0271 | 0.2186 | 0.161* | |
H6A | 0.4724 | 0.9458 | 0.1720 | 0.161* | |
C8 | −0.1662 (9) | 0.0252 (5) | 0.05508 (11) | 0.0932 (14) | |
C9 | 0.0677 (12) | −0.0498 (6) | 0.04903 (15) | 0.135 (2) | |
H9C | 0.1407 | 0.0252 | 0.0277 | 0.203* | |
H9A | 0.0629 | −0.1805 | 0.0400 | 0.203* | |
H9B | 0.1452 | −0.0408 | 0.0756 | 0.203* | |
C11 | −0.2834 (12) | 0.0378 (7) | 0.01248 (14) | 0.167 (3) | |
H11B | −0.4210 | 0.1003 | 0.0164 | 0.250* | |
H11A | −0.3071 | −0.0883 | 0.0015 | 0.250* | |
H11C | −0.1964 | 0.1093 | −0.0074 | 0.250* | |
C10 | −0.2863 (10) | −0.1069 (6) | 0.08612 (13) | 0.1190 (17) | |
H10A | −0.2111 | −0.1093 | 0.1130 | 0.179* | |
H10C | −0.2913 | −0.2334 | 0.0744 | 0.179* | |
H10B | −0.4320 | −0.0610 | 0.0904 | 0.179* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0633 (12) | 0.0647 (11) | 0.0676 (11) | −0.0163 (10) | 0.0090 (10) | −0.0156 (9) |
O1 | 0.1112 (18) | 0.0656 (12) | 0.0522 (10) | −0.0183 (14) | 0.0119 (11) | −0.0040 (8) |
O3 | 0.0714 (13) | 0.0714 (12) | 0.0456 (9) | −0.0132 (11) | −0.0044 (9) | −0.0028 (9) |
O5 | 0.1093 (17) | 0.0543 (11) | 0.0554 (10) | 0.0098 (12) | −0.0239 (11) | −0.0087 (8) |
O4 | 0.0777 (14) | 0.0751 (13) | 0.0657 (12) | −0.0223 (12) | −0.0162 (11) | 0.0133 (11) |
C3 | 0.0662 (16) | 0.0535 (13) | 0.0473 (12) | −0.0043 (14) | −0.0106 (11) | 0.0008 (11) |
C1 | 0.0632 (16) | 0.0627 (15) | 0.0494 (12) | −0.0051 (14) | 0.0037 (12) | −0.0111 (11) |
C4 | 0.091 (2) | 0.0507 (13) | 0.0447 (12) | 0.0004 (16) | −0.0106 (13) | −0.0076 (11) |
C2 | 0.0557 (14) | 0.0547 (14) | 0.0432 (11) | −0.0019 (12) | −0.0027 (10) | −0.0032 (10) |
C5 | 0.115 (3) | 0.0746 (18) | 0.0529 (15) | −0.012 (2) | 0.0151 (16) | −0.0126 (14) |
O6 | 0.188 (4) | 0.0777 (16) | 0.1032 (18) | 0.040 (2) | −0.075 (2) | −0.0221 (14) |
C7 | 0.105 (2) | 0.0609 (16) | 0.0539 (14) | 0.0002 (18) | −0.0158 (16) | −0.0055 (13) |
C6 | 0.077 (2) | 0.099 (3) | 0.145 (3) | −0.041 (2) | 0.023 (2) | −0.037 (3) |
C8 | 0.158 (4) | 0.0626 (18) | 0.0594 (17) | −0.001 (2) | −0.020 (2) | −0.0092 (14) |
C9 | 0.205 (6) | 0.087 (3) | 0.115 (3) | 0.038 (4) | 0.033 (4) | −0.026 (3) |
C11 | 0.324 (10) | 0.086 (3) | 0.090 (3) | −0.022 (5) | −0.098 (4) | −0.017 (2) |
C10 | 0.170 (5) | 0.083 (2) | 0.105 (3) | −0.039 (3) | −0.020 (3) | 0.010 (2) |
Geometric parameters (Å, º) top
O2—C1 | 1.400 (3) | C5—H5A | 0.970 |
O2—C6 | 1.419 (4) | O6—C7 | 1.192 (4) |
O1—C1 | 1.413 (3) | C7—C8 | 1.503 (5) |
O1—C5 | 1.429 (4) | C6—H6B | 0.960 |
O3—C2 | 1.424 (3) | C6—H6C | 0.960 |
O3—H21 | 0.93 (5) | C6—H6A | 0.960 |
O5—C7 | 1.337 (4) | C8—C11 | 1.516 (5) |
O5—C4 | 1.433 (3) | C8—C10 | 1.531 (6) |
O4—C3 | 1.421 (4) | C8—C9 | 1.541 (8) |
O4—H22 | 0.78 (4) | C9—H9C | 0.960 |
C3—C2 | 1.510 (3) | C9—H9A | 0.960 |
C3—C4 | 1.518 (3) | C9—H9B | 0.960 |
C3—H3 | 0.980 | C11—H11B | 0.960 |
C1—C2 | 1.501 (4) | C11—H11A | 0.960 |
C1—H1 | 0.980 | C11—H11C | 0.960 |
C4—C5 | 1.497 (5) | C10—H10A | 0.960 |
C4—H4 | 0.980 | C10—H10C | 0.960 |
C2—H2 | 0.980 | C10—H10B | 0.960 |
C5—H5B | 0.970 | | |
| | | |
C1—O2—C6 | 115.7 (3) | H5B—C5—H5A | 108.2 |
C1—O1—C5 | 111.1 (2) | O6—C7—O5 | 121.9 (3) |
C2—O3—H21 | 104 (2) | O6—C7—C8 | 125.9 (3) |
C7—O5—C4 | 117.7 (2) | O5—C7—C8 | 112.1 (3) |
C3—O4—H22 | 107 (3) | O2—C6—H6B | 109.5 |
O4—C3—C2 | 110.0 (2) | O2—C6—H6C | 109.5 |
O4—C3—C4 | 109.8 (2) | H6B—C6—H6C | 109.5 |
C2—C3—C4 | 109.3 (2) | O2—C6—H6A | 109.5 |
O4—C3—H3 | 109.2 | H6B—C6—H6A | 109.5 |
C2—C3—H3 | 109.2 | H6C—C6—H6A | 109.5 |
C4—C3—H3 | 109.2 | C7—C8—C11 | 108.7 (3) |
O2—C1—O1 | 106.6 (2) | C7—C8—C10 | 108.0 (3) |
O2—C1—C2 | 108.2 (2) | C11—C8—C10 | 111.2 (5) |
O1—C1—C2 | 110.7 (2) | C7—C8—C9 | 109.4 (4) |
O2—C1—H1 | 110.4 | C11—C8—C9 | 110.8 (4) |
O1—C1—H1 | 110.4 | C10—C8—C9 | 108.7 (4) |
C2—C1—H1 | 110.4 | C8—C9—H9C | 109.5 |
O5—C4—C5 | 109.1 (3) | C8—C9—H9A | 109.5 |
O5—C4—C3 | 108.0 (2) | H9C—C9—H9A | 109.5 |
C5—C4—C3 | 109.9 (2) | C8—C9—H9B | 109.5 |
O5—C4—H4 | 110.0 | H9C—C9—H9B | 109.5 |
C5—C4—H4 | 110.0 | H9A—C9—H9B | 109.5 |
C3—C4—H4 | 110.0 | C8—C11—H11B | 109.5 |
O3—C2—C1 | 107.2 (2) | C8—C11—H11A | 109.5 |
O3—C2—C3 | 111.7 (2) | H11B—C11—H11A | 109.5 |
C1—C2—C3 | 111.3 (2) | C8—C11—H11C | 109.5 |
O3—C2—H2 | 108.9 | H11B—C11—H11C | 109.5 |
C1—C2—H2 | 108.9 | H11A—C11—H11C | 109.5 |
C3—C2—H2 | 108.9 | C8—C10—H10A | 109.5 |
O1—C5—C4 | 110.1 (3) | C8—C10—H10C | 109.5 |
O1—C5—H5B | 109.6 | H10A—C10—H10C | 109.5 |
C4—C5—H5B | 109.6 | C8—C10—H10B | 109.5 |
O1—C5—H5A | 109.6 | H10A—C10—H10B | 109.5 |
C4—C5—H5A | 109.6 | H10C—C10—H10B | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H21···O2i | 0.93 (4) | 1.89 (5) | 2.784 (3) | 159 (3) |
O4—H22···O3i | 0.78 (4) | 2.11 (4) | 2.874 (3) | 166 (4) |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
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