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In the structure of the title compound, C16H20O7, the five-membered 1,3-dioxolane ring is disordered with two different positions, A and B (1/1); it adopts the OT4 conformation slightly distorted towards E4 for mol­ecule A, and the 1E conformation distorted towards 1TO for mol­ecule B. The pyran­ose ring adopts an almost ideal 1C4 conformation. The three-dimensional packing is stabilized by strong inter­molecular O—H...O inter­actions and weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018520/wk6054sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018520/wk6054Isup2.hkl
Contains datablock I

CCDC reference: 277803

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.041
  • wR factor = 0.103
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 1.00 mm PLAT417_ALERT_2_B Short Inter D-H..H-D H4 .. H5 .. 2.01 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.766 0.996 Tmin' and Tmax expected: 0.897 0.996 RR' = 0.854 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.97 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9A PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O1A PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O1B PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O4 .. 2.66 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12
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 25.42 From the CIF: _reflns_number_total 1700 Count of symmetry unique reflns 1702 Completeness (_total/calc) 99.88% 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 10 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2004 or? 2005); software used to prepare material for publication: SHELXTL.

3-O-Benzoyl-1,2-O-isopropylidene-β-D-fructopyranose top
Crystal data top
C16H20O7F(000) = 688
Mr = 324.32Dx = 1.376 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5729 reflections
a = 5.5771 (1) Åθ = 1.8–25.4°
b = 14.6164 (3) ŵ = 0.11 mm1
c = 19.2112 (4) ÅT = 173 K
V = 1566.04 (5) Å3Needle, colourless
Z = 41.00 × 0.06 × 0.04 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1700 independent reflections
Radiation source: fine-focus sealed tube1306 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ω scansθmax = 25.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 66
Tmin = 0.766, Tmax = 0.996k = 1717
17488 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0461P)2 + 0.7147P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1700 reflectionsΔρmax = 0.19 e Å3
244 parametersΔρmin = 0.19 e Å3
26 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (2)
Special details top

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 20 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 5729 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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*/UeqOcc. (<1)
C10.6775 (6)0.9536 (2)0.8001 (2)0.0430 (9)
H1A0.79570.96100.83810.052*
H1B0.75700.92310.76030.052*
O1A0.5848 (8)1.0386 (3)0.7800 (4)0.0485 (17)0.50
O1B0.5893 (8)1.0101 (4)0.7434 (3)0.0457 (16)0.50
O20.2659 (4)0.95327 (14)0.80672 (12)0.0372 (6)
O30.4352 (4)0.96379 (14)0.93888 (12)0.0406 (6)
O40.2831 (7)0.7950 (2)0.99338 (15)0.0701 (9)
H40.15030.78121.01110.105*
O50.4404 (6)0.67468 (17)0.89191 (17)0.0720 (9)
H50.41510.64840.93010.108*
O60.4647 (5)0.81483 (14)0.78726 (13)0.0478 (7)
O70.7761 (5)0.94053 (17)0.99800 (13)0.0513 (7)
C20.4640 (6)0.8984 (2)0.82457 (18)0.0369 (8)
C30.4578 (7)0.8776 (2)0.90163 (18)0.0403 (9)
H30.61090.84690.91550.048*
C40.2499 (8)0.8181 (2)0.9221 (2)0.0509 (10)
H4A0.09690.85300.91650.061*
C50.2442 (8)0.7328 (2)0.8760 (2)0.0575 (11)
H5A0.09110.69900.88430.069*
C60.2579 (8)0.7596 (2)0.8012 (2)0.0562 (11)
H6A0.26420.70380.77210.067*
H6B0.11160.79400.78840.067*
C70.3404 (6)1.0237 (2)0.75889 (18)0.0408 (9)
C8A0.210 (3)1.1084 (10)0.7802 (16)0.050 (5)0.50
H8A10.23771.12000.82980.075*0.50
H8A20.03811.10050.77180.075*0.50
H8A30.26931.16040.75290.075*0.50
C8B0.287 (3)1.1155 (9)0.7892 (13)0.045 (4)0.50
H8B10.37751.12340.83250.068*0.50
H8B20.11481.12010.79910.068*0.50
H8B30.33281.16330.75600.068*0.50
C9A0.309 (3)0.9888 (12)0.6864 (5)0.067 (5)0.50
H9A10.36841.03430.65330.100*0.50
H9A20.13790.97750.67770.100*0.50
H9A30.39820.93160.68080.100*0.50
C9B0.217 (2)1.0146 (11)0.6900 (4)0.054 (4)0.50
H9B10.28241.05960.65730.082*0.50
H9B20.04441.02540.69600.082*0.50
H9B30.24210.95280.67160.082*0.50
C100.5971 (6)0.9849 (2)0.98769 (18)0.0366 (8)
C110.5340 (7)1.0692 (2)1.02623 (17)0.0361 (8)
C120.6892 (7)1.0999 (2)1.07759 (18)0.0425 (9)
H120.83381.06771.08650.051*
C130.6345 (7)1.1771 (2)1.1158 (2)0.0493 (10)
H130.74091.19771.15110.059*
C140.4253 (7)1.2244 (2)1.10268 (18)0.0456 (10)
H140.38741.27751.12900.055*
C150.2719 (7)1.1949 (2)1.05165 (17)0.0408 (8)
H150.12951.22841.04230.049*
C160.3222 (7)1.1166 (2)1.01348 (17)0.0377 (9)
H160.21321.09560.97900.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0277 (18)0.045 (2)0.057 (2)0.0006 (16)0.0070 (17)0.0009 (19)
O1A0.032 (3)0.019 (3)0.095 (5)0.001 (2)0.014 (3)0.015 (3)
O1B0.027 (3)0.029 (3)0.081 (4)0.001 (2)0.021 (3)0.010 (3)
O20.0258 (12)0.0309 (12)0.0549 (14)0.0009 (11)0.0071 (12)0.0023 (11)
O30.0462 (14)0.0260 (11)0.0496 (14)0.0037 (12)0.0029 (13)0.0029 (10)
O40.088 (2)0.0422 (14)0.080 (2)0.0008 (17)0.024 (2)0.0140 (14)
O50.079 (2)0.0286 (13)0.108 (2)0.0099 (16)0.002 (2)0.0002 (14)
O60.0448 (14)0.0300 (12)0.0688 (16)0.0008 (12)0.0040 (14)0.0137 (12)
O70.0424 (15)0.0523 (15)0.0592 (16)0.0115 (15)0.0001 (14)0.0041 (13)
C20.0292 (18)0.0237 (16)0.058 (2)0.0026 (15)0.0056 (18)0.0066 (15)
C30.0377 (19)0.0205 (15)0.063 (2)0.0034 (16)0.0014 (19)0.0014 (15)
C40.051 (2)0.0285 (17)0.073 (3)0.0030 (19)0.012 (2)0.0078 (17)
C50.050 (2)0.0233 (17)0.099 (3)0.0075 (19)0.007 (3)0.0018 (19)
C60.045 (2)0.0325 (18)0.091 (3)0.0042 (19)0.004 (3)0.015 (2)
C70.0306 (18)0.0286 (17)0.063 (2)0.0036 (15)0.0060 (17)0.0015 (17)
C8A0.042 (9)0.035 (6)0.073 (10)0.006 (5)0.012 (8)0.001 (5)
C8B0.050 (10)0.028 (5)0.057 (9)0.002 (6)0.015 (9)0.001 (4)
C9A0.105 (13)0.053 (9)0.043 (6)0.022 (7)0.035 (6)0.023 (4)
C9B0.071 (9)0.050 (9)0.042 (6)0.017 (6)0.026 (5)0.013 (4)
C100.037 (2)0.0337 (18)0.0389 (19)0.0035 (17)0.0041 (17)0.0072 (15)
C110.0397 (19)0.0297 (16)0.0389 (18)0.0029 (17)0.0050 (17)0.0048 (14)
C120.032 (2)0.045 (2)0.051 (2)0.0027 (17)0.0002 (18)0.0015 (17)
C130.047 (2)0.046 (2)0.056 (2)0.010 (2)0.003 (2)0.0064 (19)
C140.049 (2)0.0369 (18)0.051 (2)0.009 (2)0.008 (2)0.0095 (16)
C150.040 (2)0.0321 (17)0.051 (2)0.0015 (17)0.0010 (19)0.0001 (15)
C160.042 (2)0.0327 (17)0.0383 (19)0.0057 (16)0.0001 (17)0.0009 (15)
Geometric parameters (Å, º) top
C1—O1A1.400 (5)C7—C8A1.493 (6)
C1—O1B1.452 (5)C7—C8B1.493 (6)
C1—C21.514 (5)C7—C9B1.499 (6)
C1—H1A0.9900C8A—H8A10.9800
C1—H1B0.9900C8A—H8A20.9800
O1A—C71.438 (5)C8A—H8A30.9800
O1B—C71.433 (5)C8B—H8B10.9800
O2—C21.407 (4)C8B—H8B20.9800
O2—C71.441 (4)C8B—H8B30.9800
O3—C101.338 (4)C9A—H9A10.9800
O3—C31.455 (4)C9A—H9A20.9800
O4—C41.423 (5)C9A—H9A30.9800
O4—H40.8400C9B—H9B10.9800
O5—C51.419 (5)C9B—H9B20.9800
O5—H50.8400C9B—H9B30.9800
O6—C21.417 (4)C10—C111.481 (5)
O6—C61.433 (5)C11—C161.391 (5)
O7—C101.207 (4)C11—C121.387 (5)
C2—C31.512 (5)C12—C131.381 (5)
C3—C41.501 (5)C12—H120.9500
C3—H31.0000C13—C141.379 (6)
C4—C51.530 (5)C13—H130.9500
C4—H4A1.0000C14—C151.371 (5)
C5—C61.491 (6)C14—H140.9500
C5—H5A1.0000C15—C161.388 (5)
C6—H6A0.9900C15—H150.9500
C6—H6B0.9900C16—H160.9500
C7—C9A1.493 (6)
O1A—C1—C2105.5 (3)O2—C7—C8A106.1 (12)
O1B—C1—C2105.6 (3)C9A—C7—C8A118.8 (12)
O1A—C1—H1A110.6O1A—C7—C8A105.0 (7)
C2—C1—H1A110.6O1B—C7—C8B113.6 (8)
O1A—C1—H1B110.6O2—C7—C8B109.6 (11)
C2—C1—H1B110.6O1B—C7—C9B104.5 (6)
H1A—C1—H1B108.8O2—C7—C9B111.5 (8)
C1—O1A—C7107.0 (4)C8B—C7—C9B109.4 (11)
C7—O1B—C1104.6 (3)C7—C8A—H8A1109.5
C2—O2—C7109.6 (2)C7—C8A—H8A2109.5
C10—O3—C3119.0 (3)C7—C8A—H8A3109.5
C4—O4—H4109.5C7—C8B—H8B1109.5
C5—O5—H5109.5C7—C8B—H8B2109.5
C2—O6—C6112.9 (3)H8B1—C8B—H8B2109.5
O2—C2—O6111.7 (3)C7—C8B—H8B3109.5
O2—C2—C1103.8 (2)H8B1—C8B—H8B3109.5
O6—C2—C1107.5 (3)H8B2—C8B—H8B3109.5
O2—C2—C3109.6 (3)C7—C9A—H9A1109.5
O6—C2—C3108.7 (3)C7—C9A—H9A2109.5
C1—C2—C3115.5 (3)C7—C9A—H9A3109.5
O3—C3—C4107.8 (3)C7—C9B—H9B1109.5
O3—C3—C2108.0 (2)C7—C9B—H9B2109.5
C4—C3—C2113.0 (3)H9B1—C9B—H9B2109.5
O3—C3—H3109.3C7—C9B—H9B3109.5
C4—C3—H3109.3H9B1—C9B—H9B3109.5
C2—C3—H3109.3H9B2—C9B—H9B3109.5
O4—C4—C3106.8 (3)O7—C10—O3123.4 (3)
O4—C4—C5111.5 (3)O7—C10—C11124.2 (3)
C3—C4—C5109.7 (3)O3—C10—C11112.4 (3)
O4—C4—H4A109.6C16—C11—C12119.6 (3)
C3—C4—H4A109.6C16—C11—C10121.9 (3)
C5—C4—H4A109.6C12—C11—C10118.5 (3)
O5—C5—C6109.0 (4)C13—C12—C11120.3 (4)
O5—C5—C4110.3 (4)C13—C12—H12119.8
C6—C5—C4110.0 (3)C11—C12—H12119.8
O5—C5—H5A109.2C14—C13—C12119.9 (4)
C6—C5—H5A109.2C14—C13—H13120.0
C4—C5—H5A109.2C12—C13—H13120.0
O6—C6—C5111.7 (3)C13—C14—C15120.1 (3)
O6—C6—H6A109.3C13—C14—H14120.0
C5—C6—H6A109.3C15—C14—H14120.0
O6—C6—H6B109.3C16—C15—C14120.8 (4)
C5—C6—H6B109.3C16—C15—H15119.6
H6A—C6—H6B107.9C14—C15—H15119.6
O1B—C7—O2108.2 (3)C15—C16—C11119.3 (3)
O2—C7—C9A108.4 (8)C15—C16—H16120.4
O2—C7—O1A101.7 (3)C11—C16—H16120.4
C9A—C7—O1A115.3 (8)
C2—C1—O1A—C727.5 (5)C2—O6—C6—C561.8 (4)
C2—C1—O1B—C728.3 (5)O5—C5—C6—O665.6 (4)
C7—O2—C2—O6101.1 (3)C4—C5—C6—O655.5 (5)
C7—O2—C2—C114.4 (3)C1—O1B—C7—O219.8 (5)
C7—O2—C2—C3138.3 (3)C1—O1B—C7—C8B102.1 (12)
C6—O6—C2—O261.4 (4)C1—O1B—C7—C9B138.7 (8)
C6—O6—C2—C1174.7 (3)C2—O2—C7—O1B3.0 (4)
C6—O6—C2—C359.7 (4)C2—O2—C7—C9A91.3 (7)
O1A—C1—C2—O28.0 (4)C2—O2—C7—O1A30.6 (4)
O1B—C1—C2—O226.5 (4)C2—O2—C7—C8A140.1 (8)
O1A—C1—C2—O6126.5 (4)C2—O2—C7—C8B121.3 (8)
O1B—C1—C2—O692.0 (4)C2—O2—C7—C9B117.4 (6)
O1A—C1—C2—C3112.0 (4)C1—O1A—C7—O235.5 (5)
O1B—C1—C2—C3146.5 (4)C1—O1A—C7—C9A81.5 (9)
C10—O3—C3—C4112.8 (3)C1—O1A—C7—C8A145.9 (14)
C10—O3—C3—C2124.8 (3)C3—O3—C10—O77.8 (5)
O2—C2—C3—O352.5 (4)C3—O3—C10—C11173.4 (3)
O6—C2—C3—O3174.9 (3)O7—C10—C11—C16178.4 (3)
C1—C2—C3—O364.2 (4)O3—C10—C11—C162.8 (4)
O2—C2—C3—C466.6 (3)O7—C10—C11—C120.0 (5)
O6—C2—C3—C455.8 (4)O3—C10—C11—C12178.8 (3)
C1—C2—C3—C4176.6 (3)C16—C11—C12—C130.1 (5)
O3—C3—C4—O467.8 (3)C10—C11—C12—C13178.6 (3)
C2—C3—C4—O4173.0 (3)C11—C12—C13—C140.4 (5)
O3—C3—C4—C5171.3 (3)C12—C13—C14—C150.1 (5)
C2—C3—C4—C552.0 (4)C13—C14—C15—C161.1 (5)
O4—C4—C5—O548.6 (5)C14—C15—C16—C111.6 (5)
C3—C4—C5—O569.5 (4)C12—C11—C16—C151.1 (5)
O4—C4—C5—C6168.9 (4)C10—C11—C16—C15179.5 (3)
C3—C4—C5—C650.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O4i0.842.333.093 (5)151
O4—H4···O5i0.842.292.951 (5)136
O5—H5···O4ii0.842.662.951 (5)102
O5—H5···O7i0.842.052.855 (4)160
C3—H3···O71.002.292.725 (5)105
C9A—H9A1···O5iii0.982.473.41 (2)160
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x+1/2, y+3/2, z+2; (iii) x+1, y+1/2, z+3/2.
 

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