Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033387/fl2143sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033387/fl2143Isup2.hkl |
CCDC reference: 657881
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.006 Å
- R factor = 0.051
- wR factor = 0.138
- Data-to-parameter ratio = 6.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.74 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.10 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
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 25.00 From the CIF: _reflns_number_total 829 Count of symmetry unique reflns 869 Completeness (_total/calc) 95.40% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
1,4:3,6-dianhydro-D-fructose, having three known chiral centers, was dissolved in MeOH. Catalytic amount of H2SO4 was added and the mixture was stirred at room temperature for 4 h,and evaporated under reduced pressure to dryness. The residue was recrystallization from MeOH,to give title compound as a colorless crystal.
The absolute configuration could not be determined from the experimental data, therefore, the Friedel equivalents were merged before refinement. The absolute configuration was set from the starting material of known configurataion.
Sugar derivatives are an important class of compounds having a broad spectrum of applications in the chemical, biochemical, medicinal(Chang et al., 2001), and pharmaceutical fields (Stutz, 1999), Here we report the structure of a novel Sugar derivative.
The molecular structure of title compound is shown in Fig.1. Torsion angle C(2)—C(3)—C(4)—C(5) is -129.9°.Intermolecular O3–H···O4 hydrogen bonds links the molecules into chains along the a axis.
Bioactivity of sugar derivatives: Stutz (1999); Chang et al. (2001).
Data collection: R-AXIS (Molecular Structure Corporation, 1993); cell refinement: R-AXIS; data reduction: R-AXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1993); software used to prepare material for publication: TEXSAN.
C8H14O5 | F(000) = 204 |
Mr = 190.19 | Dx = 1.398 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4996 (13) Å | Cell parameters from 389 reflections |
b = 6.3375 (13) Å | θ = 2–25.1° |
c = 10.983 (2) Å | µ = 0.12 mm−1 |
β = 93.07 (3)° | T = 291 K |
V = 451.77 (16) Å3 | Prism, colorless |
Z = 2 | 0.20 × 0.18 × 0.17 mm |
Rigaku R-AXIS-IV diffractometer | 772 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
Detector resolution: 0 pixels mm-1 | h = 0→7 |
Oscillation frames scans | k = −7→7 |
1418 measured reflections | l = −13→13 |
829 independent reflections |
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) = 0.138 | w = 1/[σ2(Fo2) + (0.0956P)2 + 0.0821P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
829 reflections | Δρmax = 0.20 e Å−3 |
123 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.32 (5) |
C8H14O5 | V = 451.77 (16) Å3 |
Mr = 190.19 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.4996 (13) Å | µ = 0.12 mm−1 |
b = 6.3375 (13) Å | T = 291 K |
c = 10.983 (2) Å | 0.20 × 0.18 × 0.17 mm |
β = 93.07 (3)° |
Rigaku R-AXIS-IV diffractometer | 772 reflections with I > 2σ(I) |
1418 measured reflections | Rint = 0.045 |
829 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 1 restraint |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.20 e Å−3 |
829 reflections | Δρmin = −0.23 e Å−3 |
123 parameters |
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. Because the absolute configuration was established by the structure determination of a compound containing a chiral reference molecule of known absolute configuration, we have merged the Friedels in the refinement. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0086 (5) | 0.4646 (6) | 0.1232 (3) | 0.0643 (9) | |
O2 | 0.1615 (4) | 0.4646 (6) | 0.4086 (2) | 0.0658 (9) | |
O3 | −0.2707 (5) | 0.2344 (7) | 0.2434 (4) | 0.0799 (11) | |
O4 | 0.4505 (4) | 0.6120 (5) | 0.1554 (2) | 0.0534 (8) | |
O5 | 0.3034 (4) | 0.8296 (5) | 0.2983 (3) | 0.0526 (8) | |
C1 | 0.0757 (7) | 0.6726 (7) | 0.1524 (4) | 0.0559 (11) | |
H1A | −0.0253 | 0.7449 | 0.1992 | 0.067* | |
H1B | 0.0954 | 0.7526 | 0.0786 | 0.067* | |
C2 | 0.2786 (6) | 0.6500 (6) | 0.2271 (3) | 0.0453 (9) | |
C3 | 0.2496 (6) | 0.4386 (7) | 0.2940 (4) | 0.0481 (10) | |
H3A | 0.3798 | 0.3607 | 0.3029 | 0.058* | |
C4 | 0.0928 (6) | 0.3198 (7) | 0.2124 (3) | 0.0543 (10) | |
H4A | 0.1568 | 0.1992 | 0.1733 | 0.065* | |
C5 | −0.0701 (6) | 0.2466 (7) | 0.2976 (4) | 0.0543 (10) | |
H5A | −0.0308 | 0.1077 | 0.3304 | 0.065* | |
C6 | −0.0468 (6) | 0.4083 (9) | 0.3988 (4) | 0.0647 (13) | |
H6A | −0.1315 | 0.5311 | 0.3794 | 0.078* | |
H6B | −0.0887 | 0.3488 | 0.4750 | 0.078* | |
C7 | 0.5017 (8) | 0.7814 (8) | 0.0763 (4) | 0.0684 (13) | |
H7A | 0.6192 | 0.7426 | 0.0319 | 0.103* | |
H7B | 0.5333 | 0.9054 | 0.1239 | 0.103* | |
H7C | 0.3868 | 0.8098 | 0.0201 | 0.103* | |
C8 | 0.4823 (6) | 0.8327 (9) | 0.3786 (4) | 0.0630 (12) | |
H8A | 0.4872 | 0.9629 | 0.4233 | 0.095* | |
H8B | 0.6028 | 0.8208 | 0.3322 | 0.095* | |
H8C | 0.4777 | 0.7166 | 0.4344 | 0.095* | |
H3E | −0.298 (15) | 0.36 (2) | 0.204 (8) | 0.18 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0798 (19) | 0.0572 (19) | 0.0542 (15) | −0.0192 (16) | −0.0124 (13) | 0.0022 (16) |
O2 | 0.0693 (17) | 0.078 (2) | 0.0499 (14) | −0.0169 (18) | 0.0038 (12) | 0.0008 (17) |
O3 | 0.0611 (18) | 0.074 (2) | 0.103 (3) | −0.0198 (18) | −0.0077 (16) | 0.016 (2) |
O4 | 0.0644 (17) | 0.0408 (15) | 0.0562 (14) | −0.0050 (13) | 0.0141 (12) | 0.0020 (14) |
O5 | 0.0541 (15) | 0.0410 (15) | 0.0622 (16) | 0.0028 (14) | −0.0034 (12) | −0.0060 (15) |
C1 | 0.061 (2) | 0.045 (3) | 0.060 (2) | −0.0047 (19) | −0.0137 (18) | 0.010 (2) |
C2 | 0.049 (2) | 0.042 (2) | 0.0446 (18) | 0.0019 (16) | −0.0024 (15) | 0.0011 (18) |
C3 | 0.0427 (17) | 0.044 (2) | 0.057 (2) | 0.0065 (17) | 0.0017 (15) | 0.011 (2) |
C4 | 0.068 (2) | 0.036 (2) | 0.060 (2) | −0.0005 (19) | 0.0112 (19) | −0.006 (2) |
C5 | 0.057 (2) | 0.042 (2) | 0.064 (2) | −0.0064 (18) | 0.0012 (17) | 0.008 (2) |
C6 | 0.064 (3) | 0.065 (3) | 0.067 (3) | −0.001 (2) | 0.018 (2) | 0.005 (2) |
C7 | 0.091 (3) | 0.052 (3) | 0.063 (2) | −0.015 (2) | 0.014 (2) | 0.009 (2) |
C8 | 0.062 (2) | 0.062 (3) | 0.064 (2) | −0.012 (2) | −0.0107 (18) | −0.007 (3) |
O1—C1 | 1.420 (6) | C3—C4 | 1.521 (6) |
O1—C4 | 1.429 (5) | C3—H3A | 0.9800 |
O2—C6 | 1.399 (5) | C4—C5 | 1.522 (6) |
O2—C3 | 1.419 (5) | C4—H4A | 0.9800 |
O3—C5 | 1.406 (5) | C5—C6 | 1.514 (7) |
O3—H3E | 0.91 (14) | C5—H5A | 0.9800 |
O4—C2 | 1.422 (5) | C6—H6A | 0.9700 |
O4—C7 | 1.431 (5) | C6—H6B | 0.9700 |
O5—C2 | 1.385 (5) | C7—H7A | 0.9600 |
O5—C8 | 1.421 (4) | C7—H7B | 0.9600 |
C1—C2 | 1.523 (5) | C7—H7C | 0.9600 |
C1—H1A | 0.9700 | C8—H8A | 0.9600 |
C1—H1B | 0.9700 | C8—H8B | 0.9600 |
C2—C3 | 1.545 (6) | C8—H8C | 0.9600 |
C1—O1—C4 | 109.9 (3) | C3—C4—H4A | 110.9 |
C6—O2—C3 | 109.7 (3) | C5—C4—H4A | 110.9 |
C5—O3—H3E | 108 (7) | O3—C5—C6 | 113.7 (4) |
C2—O4—C7 | 115.1 (3) | O3—C5—C4 | 114.6 (3) |
C2—O5—C8 | 115.4 (3) | C6—C5—C4 | 101.5 (3) |
O1—C1—C2 | 106.3 (3) | O3—C5—H5A | 108.9 |
O1—C1—H1A | 110.5 | C6—C5—H5A | 108.9 |
C2—C1—H1A | 110.5 | C4—C5—H5A | 108.9 |
O1—C1—H1B | 110.5 | O2—C6—C5 | 106.7 (4) |
C2—C1—H1B | 110.5 | O2—C6—H6A | 110.4 |
H1A—C1—H1B | 108.7 | C5—C6—H6A | 110.4 |
O5—C2—O4 | 112.4 (3) | O2—C6—H6B | 110.4 |
O5—C2—C1 | 107.4 (3) | C5—C6—H6B | 110.4 |
O4—C2—C1 | 113.7 (3) | H6A—C6—H6B | 108.6 |
O5—C2—C3 | 117.2 (3) | O4—C7—H7A | 109.5 |
O4—C2—C3 | 103.6 (3) | O4—C7—H7B | 109.5 |
C1—C2—C3 | 102.3 (3) | H7A—C7—H7B | 109.5 |
O2—C3—C4 | 106.9 (3) | O4—C7—H7C | 109.5 |
O2—C3—C2 | 112.7 (3) | H7A—C7—H7C | 109.5 |
C4—C3—C2 | 104.1 (3) | H7B—C7—H7C | 109.5 |
O2—C3—H3A | 110.9 | O5—C8—H8A | 109.5 |
C4—C3—H3A | 110.9 | O5—C8—H8B | 109.5 |
C2—C3—H3A | 110.9 | H8A—C8—H8B | 109.5 |
O1—C4—C3 | 107.8 (3) | O5—C8—H8C | 109.5 |
O1—C4—C5 | 111.3 (3) | H8A—C8—H8C | 109.5 |
C3—C4—C5 | 104.7 (3) | H8B—C8—H8C | 109.5 |
O1—C4—H4A | 110.9 | ||
C4—O1—C1—C2 | 25.6 (4) | O4—C2—C3—C4 | −93.3 (3) |
C8—O5—C2—O4 | −56.7 (4) | C1—C2—C3—C4 | 25.1 (4) |
C8—O5—C2—C1 | 177.6 (3) | C1—O1—C4—C3 | −8.7 (4) |
C8—O5—C2—C3 | 63.2 (4) | C1—O1—C4—C5 | 105.6 (4) |
C7—O4—C2—O5 | −56.8 (4) | O2—C3—C4—O1 | 108.3 (4) |
C7—O4—C2—C1 | 65.4 (4) | C2—C3—C4—O1 | −11.2 (4) |
C7—O4—C2—C3 | 175.7 (3) | O2—C3—C4—C5 | −10.4 (4) |
O1—C1—C2—O5 | −155.2 (3) | C2—C3—C4—C5 | −129.9 (3) |
O1—C1—C2—O4 | 79.9 (4) | O1—C4—C5—O3 | 32.0 (5) |
O1—C1—C2—C3 | −31.2 (4) | C3—C4—C5—O3 | 148.3 (4) |
C6—O2—C3—C4 | −10.7 (5) | O1—C4—C5—C6 | −91.0 (4) |
C6—O2—C3—C2 | 103.1 (4) | C3—C4—C5—C6 | 25.3 (4) |
O5—C2—C3—O2 | 26.8 (4) | C3—O2—C6—C5 | 27.8 (5) |
O4—C2—C3—O2 | 151.2 (3) | O3—C5—C6—O2 | −156.3 (4) |
C1—C2—C3—O2 | −90.3 (4) | C4—C5—C6—O2 | −32.7 (5) |
O5—C2—C3—C4 | 142.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3E···O4i | 0.91 (14) | 2.33 (13) | 3.123 (6) | 145 (9) |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H14O5 |
Mr | 190.19 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 291 |
a, b, c (Å) | 6.4996 (13), 6.3375 (13), 10.983 (2) |
β (°) | 93.07 (3) |
V (Å3) | 451.77 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.20 × 0.18 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS-IV |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1418, 829, 772 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.138, 1.04 |
No. of reflections | 829 |
No. of parameters | 123 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.23 |
Computer programs: R-AXIS (Molecular Structure Corporation, 1993), R-AXIS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), TEXSAN (Molecular Structure Corporation, 1993), TEXSAN.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3E···O4i | 0.91 (14) | 2.33 (13) | 3.123 (6) | 145 (9) |
Symmetry code: (i) x−1, y, z. |
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Sugar derivatives are an important class of compounds having a broad spectrum of applications in the chemical, biochemical, medicinal(Chang et al., 2001), and pharmaceutical fields (Stutz, 1999), Here we report the structure of a novel Sugar derivative.
The molecular structure of title compound is shown in Fig.1. Torsion angle C(2)—C(3)—C(4)—C(5) is -129.9°.Intermolecular O3–H···O4 hydrogen bonds links the molecules into chains along the a axis.