The crystal and molecular structure of the title compound, C
16H
28O
7, has been determined by X-ray analysis at 100 K. The six-membered ring adopts the chair conformation. Molecules are connected in pairs around twofold rotation axes
via two O—H
O hydrogen bonds with 2.852 (2) Å.
Supporting information
CCDC reference: 236081
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.108
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.46 Ratio
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 33.00 A 3
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 30.00
From the CIF: _reflns_number_total 2829
Count of symmetry unique reflns 2957
Completeness (_total/calc) 95.67%
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
0 ALERT level B = Potentially serious problem
3 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1990); software used to prepare material for publication: SHELXL97.
Methyl 3,4-di-O-pivaloyl-
β-
D-xylopyranoside
top
Crystal data top
C16H28O7 | F(000) = 720 |
Mr = 332.38 | Dx = 1.187 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 6732 reflections |
a = 19.111 (3) Å | θ = 8.3–28.2° |
b = 5.9619 (11) Å | µ = 0.09 mm−1 |
c = 18.726 (2) Å | T = 100 K |
β = 119.337 (12)° | Needle, colorless |
V = 1860.0 (5) Å3 | 0.59 × 0.23 × 0.16 mm |
Z = 4 | |
Data collection top
Xcalibur CCD diffractometer | 2507 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.094 |
Graphite monochromator | θmax = 30.0°, θmin = 4.7° |
ω scans | h = −26→26 |
19022 measured reflections | k = −8→7 |
2829 independent reflections | l = −26→26 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3 |
2829 reflections | (Δ/σ)max < 0.001 |
240 parameters | Δρmax = 0.37 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. The data did not permit the determination of the absolute structure; (the
stereochemistry is the relative configuration based on the absolute
stereochemistry of related compounds). |
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 | |
O1 | −0.11050 (7) | 0.5665 (2) | 0.60072 (7) | 0.0191 (3) | |
O2 | −0.11587 (7) | 0.3135 (3) | 0.50673 (7) | 0.0206 (3) | |
O3 | 0.05333 (8) | 0.2446 (3) | 0.60208 (8) | 0.0221 (3) | |
H3 | 0.0681 | 0.2626 | 0.5681 | 0.033* | |
O4 | 0.13200 (6) | 0.6439 (2) | 0.69507 (7) | 0.0175 (3) | |
O5 | 0.21488 (7) | 0.4831 (3) | 0.81793 (8) | 0.0224 (3) | |
O6 | 0.05944 (7) | 0.7826 (2) | 0.79202 (7) | 0.0176 (3) | |
O7 | −0.00009 (7) | 1.1205 (3) | 0.76669 (8) | 0.0211 (3) | |
C1 | −0.07108 (10) | 0.3772 (4) | 0.58920 (10) | 0.0165 (3) | |
C2 | 0.01356 (9) | 0.4420 (3) | 0.60646 (10) | 0.0158 (4) | |
C3 | 0.06122 (9) | 0.5443 (3) | 0.69143 (10) | 0.0140 (3) | |
C4 | 0.01398 (9) | 0.7278 (3) | 0.70560 (10) | 0.0150 (3) | |
C5 | −0.06902 (9) | 0.6401 (4) | 0.68469 (10) | 0.0181 (4) | |
C6 | −0.18385 (11) | 0.1762 (4) | 0.48985 (11) | 0.0257 (5) | |
H6A | −0.1660 | 0.0419 | 0.5222 | 0.039* | |
H6B | −0.2118 | 0.1373 | 0.4328 | 0.039* | |
H6C | −0.2193 | 0.2573 | 0.5033 | 0.039* | |
C7 | 0.20482 (9) | 0.5999 (3) | 0.76104 (10) | 0.0163 (4) | |
C8 | 0.27062 (10) | 0.7221 (4) | 0.75181 (11) | 0.0189 (4) | |
C9 | 0.26718 (11) | 0.6452 (4) | 0.67147 (11) | 0.0253 (4) | |
H9A | 0.2158 | 0.6832 | 0.6259 | 0.038* | |
H9B | 0.2748 | 0.4858 | 0.6729 | 0.038* | |
H9C | 0.3088 | 0.7189 | 0.6656 | 0.038* | |
C10 | 0.35258 (10) | 0.6606 (5) | 0.82513 (12) | 0.0299 (5) | |
H10A | 0.3945 | 0.7285 | 0.8184 | 0.045* | |
H10B | 0.3590 | 0.5006 | 0.8279 | 0.045* | |
H10C | 0.3553 | 0.7142 | 0.8748 | 0.045* | |
C11 | 0.25620 (13) | 0.9745 (4) | 0.74962 (14) | 0.0289 (5) | |
H11A | 0.2047 | 1.0099 | 0.7038 | 0.043* | |
H11B | 0.2974 | 1.0524 | 0.7443 | 0.043* | |
H11C | 0.2574 | 1.0198 | 0.7994 | 0.043* | |
C12 | 0.04880 (9) | 0.9885 (3) | 0.81484 (10) | 0.0155 (3) | |
C13 | 0.10340 (10) | 1.0299 (3) | 0.90630 (10) | 0.0177 (4) | |
C14 | 0.19084 (10) | 0.9730 (5) | 0.93042 (12) | 0.0287 (5) | |
H14A | 0.1935 | 0.8223 | 0.9138 | 0.043* | |
H14B | 0.2240 | 0.9860 | 0.9887 | 0.043* | |
H14C | 0.2095 | 1.0752 | 0.9038 | 0.043* | |
C15 | 0.07450 (14) | 0.8781 (4) | 0.95337 (12) | 0.0285 (4) | |
H15A | 0.0200 | 0.9150 | 0.9380 | 0.043* | |
H15B | 0.1080 | 0.9010 | 1.0112 | 0.043* | |
H15C | 0.0775 | 0.7240 | 0.9403 | 0.043* | |
C16 | 0.09744 (11) | 1.2758 (4) | 0.92512 (11) | 0.0211 (4) | |
H16A | 0.1133 | 1.3691 | 0.8937 | 0.032* | |
H16B | 0.1322 | 1.3033 | 0.9825 | 0.032* | |
H16C | 0.0431 | 1.3099 | 0.9110 | 0.032* | |
H11 | −0.0693 (12) | 0.245 (4) | 0.6265 (13) | 0.013 (5)* | |
H21 | 0.0077 (12) | 0.551 (4) | 0.5673 (14) | 0.015 (5)* | |
H31 | 0.0761 (14) | 0.427 (5) | 0.7335 (15) | 0.022 (6)* | |
H41 | 0.0108 (12) | 0.855 (5) | 0.6770 (13) | 0.013 (5)* | |
H51 | −0.1027 (14) | 0.758 (5) | 0.6878 (15) | 0.026 (6)* | |
H52 | −0.0664 (12) | 0.517 (4) | 0.7230 (14) | 0.016 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0154 (5) | 0.0238 (8) | 0.0152 (5) | 0.0025 (5) | 0.0051 (4) | −0.0018 (5) |
O2 | 0.0192 (5) | 0.0287 (9) | 0.0127 (5) | −0.0067 (5) | 0.0068 (4) | −0.0030 (5) |
O3 | 0.0259 (6) | 0.0241 (9) | 0.0208 (6) | 0.0052 (6) | 0.0149 (5) | −0.0012 (6) |
O4 | 0.0138 (5) | 0.0230 (8) | 0.0158 (5) | −0.0013 (5) | 0.0072 (4) | 0.0034 (5) |
O5 | 0.0191 (5) | 0.0280 (9) | 0.0189 (6) | 0.0022 (5) | 0.0083 (5) | 0.0073 (6) |
O6 | 0.0202 (5) | 0.0163 (8) | 0.0128 (5) | 0.0021 (5) | 0.0053 (4) | −0.0014 (5) |
O7 | 0.0241 (6) | 0.0198 (8) | 0.0173 (6) | 0.0054 (5) | 0.0086 (5) | 0.0027 (6) |
C1 | 0.0168 (6) | 0.0200 (10) | 0.0128 (7) | −0.0010 (6) | 0.0074 (6) | −0.0008 (7) |
C2 | 0.0159 (6) | 0.0189 (10) | 0.0128 (7) | 0.0009 (6) | 0.0071 (6) | −0.0008 (7) |
C3 | 0.0118 (6) | 0.0177 (10) | 0.0130 (6) | −0.0004 (6) | 0.0066 (5) | 0.0012 (7) |
C4 | 0.0167 (7) | 0.0156 (10) | 0.0119 (7) | 0.0007 (6) | 0.0063 (6) | 0.0004 (7) |
C5 | 0.0155 (6) | 0.0229 (11) | 0.0156 (7) | 0.0006 (7) | 0.0076 (6) | −0.0031 (7) |
C6 | 0.0226 (8) | 0.0329 (14) | 0.0196 (8) | −0.0092 (8) | 0.0088 (7) | −0.0061 (8) |
C7 | 0.0161 (7) | 0.0180 (10) | 0.0154 (7) | 0.0013 (6) | 0.0081 (6) | −0.0014 (7) |
C8 | 0.0146 (7) | 0.0258 (11) | 0.0168 (7) | −0.0005 (7) | 0.0082 (6) | 0.0016 (7) |
C9 | 0.0235 (8) | 0.0350 (13) | 0.0223 (8) | −0.0037 (8) | 0.0151 (7) | −0.0045 (9) |
C10 | 0.0145 (7) | 0.0484 (16) | 0.0225 (9) | −0.0019 (8) | 0.0057 (6) | 0.0068 (10) |
C11 | 0.0307 (9) | 0.0255 (13) | 0.0378 (11) | −0.0078 (8) | 0.0223 (9) | −0.0043 (10) |
C12 | 0.0175 (7) | 0.0155 (10) | 0.0149 (7) | −0.0009 (6) | 0.0091 (6) | 0.0002 (7) |
C13 | 0.0196 (7) | 0.0177 (11) | 0.0143 (7) | 0.0018 (6) | 0.0072 (6) | −0.0003 (7) |
C14 | 0.0182 (7) | 0.0348 (13) | 0.0242 (9) | 0.0064 (8) | 0.0034 (7) | −0.0083 (9) |
C15 | 0.0492 (11) | 0.0208 (12) | 0.0200 (9) | −0.0053 (9) | 0.0205 (9) | −0.0012 (8) |
C16 | 0.0231 (7) | 0.0165 (11) | 0.0210 (8) | −0.0003 (7) | 0.0086 (7) | −0.0024 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.431 (2) | C8—C11 | 1.527 (4) |
O1—C5 | 1.440 (2) | C8—C10 | 1.538 (3) |
O2—C1 | 1.402 (2) | C8—C9 | 1.543 (2) |
O2—C6 | 1.434 (2) | C9—H9A | 0.9600 |
O3—C2 | 1.425 (2) | C9—H9B | 0.9600 |
O3—H3 | 0.8200 | C9—H9C | 0.9600 |
O4—C7 | 1.3591 (19) | C10—H10A | 0.9600 |
O4—C3 | 1.4479 (18) | C10—H10B | 0.9600 |
O5—C7 | 1.207 (2) | C10—H10C | 0.9600 |
O6—C12 | 1.348 (2) | C11—H11A | 0.9600 |
O6—C4 | 1.4500 (19) | C11—H11B | 0.9600 |
O7—C12 | 1.217 (2) | C11—H11C | 0.9600 |
C1—C2 | 1.536 (2) | C12—C13 | 1.527 (2) |
C1—H11 | 1.04 (2) | C13—C16 | 1.525 (3) |
C2—C3 | 1.521 (2) | C13—C14 | 1.540 (2) |
C2—H21 | 0.95 (2) | C13—C15 | 1.542 (3) |
C3—C4 | 1.522 (3) | C14—H14A | 0.9600 |
C3—H31 | 0.99 (3) | C14—H14B | 0.9600 |
C4—C5 | 1.528 (2) | C14—H14C | 0.9600 |
C4—H41 | 0.91 (3) | C15—H15A | 0.9600 |
C5—H51 | 0.97 (3) | C15—H15B | 0.9600 |
C5—H52 | 1.01 (2) | C15—H15C | 0.9600 |
C6—H6A | 0.9600 | C16—H16A | 0.9600 |
C6—H6B | 0.9600 | C16—H16B | 0.9600 |
C6—H6C | 0.9600 | C16—H16C | 0.9600 |
C7—C8 | 1.534 (2) | | |
| | | |
C1—O1—C5 | 110.89 (13) | C7—C8—C9 | 108.86 (16) |
C1—O2—C6 | 113.31 (13) | C10—C8—C9 | 109.75 (16) |
C2—O3—H3 | 109.5 | C8—C9—H9A | 109.5 |
C7—O4—C3 | 118.72 (13) | C8—C9—H9B | 109.5 |
C12—O6—C4 | 117.26 (14) | H9A—C9—H9B | 109.5 |
O2—C1—O1 | 107.30 (14) | C8—C9—H9C | 109.5 |
O2—C1—C2 | 108.16 (12) | H9A—C9—H9C | 109.5 |
O1—C1—C2 | 110.36 (16) | H9B—C9—H9C | 109.5 |
O2—C1—H11 | 109.5 (13) | C8—C10—H10A | 109.5 |
O1—C1—H11 | 110.0 (12) | C8—C10—H10B | 109.5 |
C2—C1—H11 | 111.4 (11) | H10A—C10—H10B | 109.5 |
O3—C2—C3 | 109.17 (13) | C8—C10—H10C | 109.5 |
O3—C2—C1 | 108.45 (16) | H10A—C10—H10C | 109.5 |
C3—C2—C1 | 110.50 (12) | H10B—C10—H10C | 109.5 |
O3—C2—H21 | 112.8 (14) | C8—C11—H11A | 109.5 |
C3—C2—H21 | 108.6 (15) | C8—C11—H11B | 109.5 |
C1—C2—H21 | 107.3 (12) | H11A—C11—H11B | 109.5 |
O4—C3—C2 | 106.29 (12) | C8—C11—H11C | 109.5 |
O4—C3—C4 | 108.50 (15) | H11A—C11—H11C | 109.5 |
C2—C3—C4 | 111.60 (13) | H11B—C11—H11C | 109.5 |
O4—C3—H31 | 110.9 (13) | O7—C12—O6 | 122.33 (16) |
C2—C3—H31 | 110.1 (15) | O7—C12—C13 | 125.55 (18) |
C4—C3—H31 | 109.5 (13) | O6—C12—C13 | 112.11 (15) |
O6—C4—C3 | 105.91 (13) | C16—C13—C12 | 109.10 (16) |
O6—C4—C5 | 110.01 (12) | C16—C13—C14 | 109.69 (17) |
C3—C4—C5 | 109.85 (16) | C12—C13—C14 | 109.90 (14) |
O6—C4—H41 | 107.3 (15) | C16—C13—C15 | 110.10 (15) |
C3—C4—H41 | 111.7 (13) | C12—C13—C15 | 107.89 (15) |
C5—C4—H41 | 111.8 (13) | C14—C13—C15 | 110.13 (18) |
O1—C5—C4 | 109.34 (12) | C13—C14—H14A | 109.5 |
O1—C5—H51 | 105.0 (15) | C13—C14—H14B | 109.5 |
C4—C5—H51 | 111.8 (16) | H14A—C14—H14B | 109.5 |
O1—C5—H52 | 111.2 (14) | C13—C14—H14C | 109.5 |
C4—C5—H52 | 112.5 (12) | H14A—C14—H14C | 109.5 |
H51—C5—H52 | 106.7 (19) | H14B—C14—H14C | 109.5 |
O2—C6—H6A | 109.5 | C13—C15—H15A | 109.5 |
O2—C6—H6B | 109.5 | C13—C15—H15B | 109.5 |
H6A—C6—H6B | 109.5 | H15A—C15—H15B | 109.5 |
O2—C6—H6C | 109.5 | C13—C15—H15C | 109.5 |
H6A—C6—H6C | 109.5 | H15A—C15—H15C | 109.5 |
H6B—C6—H6C | 109.5 | H15B—C15—H15C | 109.5 |
O5—C7—O4 | 124.28 (15) | C13—C16—H16A | 109.5 |
O5—C7—C8 | 126.04 (15) | C13—C16—H16B | 109.5 |
O4—C7—C8 | 109.68 (14) | H16A—C16—H16B | 109.5 |
C11—C8—C7 | 108.88 (15) | C13—C16—H16C | 109.5 |
C11—C8—C10 | 110.51 (19) | H16A—C16—H16C | 109.5 |
C7—C8—C10 | 108.58 (15) | H16B—C16—H16C | 109.5 |
C11—C8—C9 | 110.22 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 2.04 | 2.852 (2) | 174 |
Symmetry code: (i) −x, y, −z+1. |