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In the title compound, C17H24O9·H2O, the syringin [4-(3-hydr­oxy-1-propen­yl)-2,6-dimethoxy­phenyl-β-D-glucopyran­oside] mol­ecule contains a benzene ring, two meth­oxy groups, an allyl group and a D-glucose fragment which adopts a chair conformation. A mol­ecular column running along the a axis is formed via O—H...O and C—H...O hydrogen bonds and C—H...π inter­actions. The columns are assembled into a three-dimensional framework by an O—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048008/is2094sup1.cif
Contains datablocks I, 060905c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048008/is2094Isup2.hkl
Contains datablock I

CCDC reference: 630022

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.057
  • wR factor = 0.168
  • Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.91 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O2 .. 2.63 Ang.
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 1986 Count of symmetry unique reflns 1987 Completeness (_total/calc) 99.95% 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 C12 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 6 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 2 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4-(3-hydroxy-1-propenyl)-2,6-dimethoxyphenyl-β-D-glucopyranoside monohydrate top
Crystal data top
C17H24O9·H2OF(000) = 832
Mr = 390.38Dx = 1.362 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1728 reflections
a = 4.855 (2) Åθ = 2.3–25.3°
b = 19.519 (3) ŵ = 0.11 mm1
c = 20.084 (3) ÅT = 298 K
V = 1903.3 (9) Å3Prism, colourless
Z = 40.49 × 0.15 × 0.10 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1986 independent reflections
Radiation source: fine-focus sealed tube1241 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.085
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 55
Tmin = 0.980, Tmax = 0.989k = 1823
9643 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0605P)2 + 3.1656P]
where P = (Fo2 + 2Fc2)/3
1986 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Experimental. UV λmax (MeOH) (nm): 221,265; IR υmax(cm-1): 3450, 3431, 2890, 1590, 1510, 1463, 1421, 1100, 980, 968.

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*/Ueq
O10.4406 (14)0.2149 (2)0.1672 (2)0.0658 (17)
H10.44560.18770.13600.099*
O20.1102 (10)0.5076 (2)0.37876 (19)0.0432 (12)
O30.3809 (9)0.48704 (19)0.49027 (19)0.0352 (10)
O40.7253 (12)0.3803 (2)0.5063 (2)0.0551 (14)
O50.6507 (9)0.51822 (19)0.57673 (18)0.0344 (11)
O60.5074 (11)0.6101 (2)0.42269 (19)0.0457 (13)
H60.38290.58430.41130.069*
O70.7343 (10)0.71510 (19)0.5040 (3)0.0488 (13)
H70.87660.73730.49960.073*
O81.1187 (10)0.6610 (2)0.6061 (2)0.0438 (12)
H81.09100.70010.61930.066*
O90.9502 (12)0.4670 (2)0.6876 (3)0.0575 (14)
H90.80600.44640.68050.086*
O100.4528 (13)0.3975 (2)0.6482 (3)0.0747 (18)
H180.30130.41800.65550.112*
H190.49710.40820.60860.112*
C10.642 (2)0.1964 (4)0.2152 (3)0.077 (3)
H1A0.82340.19790.19490.093*
H1B0.60890.14990.23000.093*
C20.636 (2)0.2436 (4)0.2740 (4)0.065 (3)
H20.76670.23690.30730.078*
C30.4587 (17)0.2938 (3)0.2816 (3)0.0479 (19)
H30.32710.29910.24840.057*
C40.4474 (16)0.3429 (3)0.3382 (3)0.0414 (17)
C50.2749 (16)0.3989 (3)0.3317 (3)0.0418 (17)
H50.16650.40350.29380.050*
C60.2623 (15)0.4485 (3)0.3816 (3)0.0342 (15)
C70.4160 (15)0.4398 (3)0.4392 (3)0.0353 (15)
C80.5837 (16)0.3833 (3)0.4462 (3)0.0387 (16)
C90.6067 (17)0.3348 (3)0.3955 (3)0.0439 (17)
H9A0.72570.29770.39980.053*
C100.0512 (16)0.5191 (4)0.3190 (3)0.053 (2)
H10A0.06930.52160.28120.080*
H10B0.15110.56130.32320.080*
H10C0.17870.48200.31310.080*
C110.9154 (19)0.3266 (3)0.5171 (4)0.064 (2)
H11A0.81970.28360.51720.096*
H11B1.00500.33310.55920.096*
H11C1.05060.32670.48220.096*
C120.6166 (15)0.5272 (3)0.5070 (3)0.0334 (14)
H120.77970.51140.48270.040*
C130.5606 (14)0.6017 (3)0.4929 (3)0.0317 (14)
H130.39710.61590.51790.038*
C140.8008 (14)0.6446 (3)0.5145 (3)0.0326 (15)
H140.96190.63260.48750.039*
C150.8645 (15)0.6304 (3)0.5878 (3)0.0340 (15)
H150.71650.64890.61560.041*
C160.8925 (15)0.5538 (3)0.6002 (3)0.0358 (15)
H161.05600.53630.57720.043*
C170.9124 (19)0.5378 (3)0.6738 (3)0.052 (2)
H17A1.06530.56320.69260.063*
H17B0.74540.55330.69560.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.114 (5)0.040 (3)0.044 (3)0.003 (3)0.006 (3)0.011 (2)
O20.046 (3)0.046 (3)0.038 (2)0.010 (3)0.008 (2)0.006 (2)
O30.034 (2)0.033 (2)0.038 (2)0.005 (2)0.003 (2)0.0095 (18)
O40.072 (4)0.040 (3)0.053 (3)0.015 (3)0.023 (3)0.003 (2)
O50.041 (3)0.030 (2)0.033 (2)0.005 (2)0.004 (2)0.0037 (17)
O60.056 (4)0.043 (3)0.038 (2)0.002 (3)0.013 (2)0.010 (2)
O70.036 (3)0.024 (2)0.086 (3)0.000 (2)0.002 (3)0.012 (2)
O80.036 (3)0.038 (2)0.057 (3)0.003 (2)0.004 (2)0.010 (2)
O90.065 (4)0.053 (3)0.054 (3)0.003 (3)0.007 (3)0.018 (3)
O100.075 (4)0.069 (4)0.080 (4)0.010 (4)0.013 (4)0.022 (3)
C10.128 (10)0.057 (5)0.048 (4)0.019 (6)0.016 (6)0.019 (4)
C20.094 (7)0.047 (4)0.055 (4)0.013 (5)0.010 (5)0.023 (4)
C30.062 (6)0.040 (4)0.041 (4)0.001 (4)0.001 (4)0.009 (3)
C40.047 (5)0.037 (4)0.040 (4)0.007 (4)0.000 (4)0.007 (3)
C50.045 (4)0.040 (4)0.040 (4)0.000 (4)0.002 (3)0.006 (3)
C60.035 (4)0.033 (3)0.035 (3)0.002 (3)0.001 (3)0.008 (3)
C70.041 (4)0.028 (3)0.037 (3)0.002 (3)0.002 (3)0.009 (3)
C80.048 (5)0.034 (3)0.035 (3)0.005 (4)0.009 (3)0.004 (3)
C90.051 (5)0.033 (3)0.048 (4)0.003 (4)0.002 (4)0.006 (3)
C100.052 (5)0.065 (5)0.042 (4)0.008 (5)0.019 (4)0.003 (3)
C110.061 (6)0.045 (4)0.087 (6)0.014 (5)0.009 (5)0.004 (4)
C120.036 (4)0.032 (3)0.032 (3)0.001 (3)0.002 (3)0.004 (3)
C130.031 (4)0.032 (3)0.032 (3)0.001 (3)0.003 (3)0.004 (3)
C140.030 (4)0.028 (3)0.040 (3)0.007 (3)0.005 (3)0.001 (3)
C150.030 (4)0.034 (3)0.038 (3)0.005 (3)0.004 (3)0.002 (3)
C160.038 (4)0.033 (3)0.036 (3)0.003 (3)0.000 (3)0.000 (3)
C170.073 (6)0.046 (4)0.038 (3)0.001 (4)0.013 (4)0.008 (3)
Geometric parameters (Å, º) top
O1—C11.421 (10)C4—C51.383 (9)
O1—H10.8200C4—C91.396 (9)
O2—C61.370 (7)C5—C61.395 (8)
O2—C101.450 (7)C5—H50.9300
O3—C71.389 (6)C6—C71.387 (8)
O3—C121.427 (7)C7—C81.378 (8)
O4—C81.389 (7)C8—C91.396 (8)
O4—C111.413 (8)C9—H9A0.9300
O5—C121.421 (6)C10—H10A0.9600
O5—C161.443 (8)C10—H10B0.9600
O6—C131.444 (7)C10—H10C0.9600
O6—H60.8200C11—H11A0.9600
O7—C141.430 (6)C11—H11B0.9600
O7—H70.8200C11—H11C0.9600
O8—C151.419 (8)C12—C131.505 (7)
O8—H80.8200C12—H120.9800
O9—C171.420 (7)C13—C141.499 (8)
O9—H90.8200C13—H130.9800
O10—H180.8500C14—C151.529 (8)
O10—H190.8500C14—H140.9800
C1—C21.498 (9)C15—C161.523 (8)
C1—H1A0.9700C15—H150.9800
C1—H1B0.9700C16—C171.512 (8)
C2—C31.313 (10)C16—H160.9800
C2—H20.9300C17—H17A0.9700
C3—C41.488 (8)C17—H17B0.9700
C3—H30.9300
C1—O1—H1109.5H10A—C10—H10C109.5
C6—O2—C10117.1 (5)H10B—C10—H10C109.5
C7—O3—C12116.1 (5)O4—C11—H11A109.5
C8—O4—C11119.2 (5)O4—C11—H11B109.5
C12—O5—C16111.0 (5)H11A—C11—H11B109.5
C13—O6—H6109.5O4—C11—H11C109.5
C14—O7—H7109.5H11A—C11—H11C109.5
C15—O8—H8109.5H11B—C11—H11C109.5
C17—O9—H9109.5O5—C12—O3104.9 (5)
H18—O10—H19105.4O5—C12—C13109.0 (5)
O1—C1—C2111.5 (7)O3—C12—C13110.0 (5)
O1—C1—H1A109.3O5—C12—H12110.9
C2—C1—H1A109.3O3—C12—H12110.9
O1—C1—H1B109.3C13—C12—H12110.9
C2—C1—H1B109.3O6—C13—C14111.0 (5)
H1A—C1—H1B108.0O6—C13—C12109.0 (5)
C3—C2—C1124.2 (8)C14—C13—C12110.2 (5)
C3—C2—H2117.9O6—C13—H13108.9
C1—C2—H2117.9C14—C13—H13108.9
C2—C3—C4126.4 (7)C12—C13—H13108.9
C2—C3—H3116.8O7—C14—C13108.6 (5)
C4—C3—H3116.8O7—C14—C15111.2 (5)
C5—C4—C9120.2 (6)C13—C14—C15109.5 (5)
C5—C4—C3117.4 (6)O7—C14—H14109.1
C9—C4—C3122.4 (6)C13—C14—H14109.1
C4—C5—C6120.5 (6)C15—C14—H14109.1
C4—C5—H5119.7O8—C15—C16107.0 (5)
C6—C5—H5119.7O8—C15—C14110.5 (5)
O2—C6—C7115.3 (5)C16—C15—C14110.8 (5)
O2—C6—C5125.3 (6)O8—C15—H15109.5
C7—C6—C5119.4 (6)C16—C15—H15109.5
C8—C7—C6120.1 (5)C14—C15—H15109.5
C8—C7—O3121.9 (5)O5—C16—C17105.8 (6)
C6—C7—O3117.9 (5)O5—C16—C15110.2 (5)
C7—C8—O4114.5 (5)C17—C16—C15111.7 (5)
C7—C8—C9121.0 (6)O5—C16—H16109.7
O4—C8—C9124.5 (6)C17—C16—H16109.7
C8—C9—C4118.7 (6)C15—C16—H16109.7
C8—C9—H9A120.6O9—C17—C16113.6 (5)
C4—C9—H9A120.6O9—C17—H17A108.8
O2—C10—H10A109.5C16—C17—H17A108.8
O2—C10—H10B109.5O9—C17—H17B108.8
H10A—C10—H10B109.5C16—C17—H17B108.8
O2—C10—H10C109.5H17A—C17—H17B107.7
O1—C1—C2—C32.9 (14)C3—C4—C9—C8179.9 (7)
C1—C2—C3—C4178.6 (8)C16—O5—C12—O3177.2 (4)
C2—C3—C4—C5169.5 (8)C16—O5—C12—C1365.1 (6)
C2—C3—C4—C99.3 (12)C7—O3—C12—O5126.7 (5)
C9—C4—C5—C61.4 (10)C7—O3—C12—C13116.3 (5)
C3—C4—C5—C6177.4 (7)O5—C12—C13—O6176.1 (5)
C10—O2—C6—C7179.3 (6)O3—C12—C13—O661.6 (7)
C10—O2—C6—C50.2 (10)O5—C12—C13—C1461.9 (7)
C4—C5—C6—O2176.4 (6)O3—C12—C13—C14176.4 (5)
C4—C5—C6—C72.7 (10)O6—C13—C14—O762.5 (6)
O2—C6—C7—C8177.8 (6)C12—C13—C14—O7176.7 (5)
C5—C6—C7—C81.4 (10)O6—C13—C14—C15175.9 (5)
O2—C6—C7—O36.3 (9)C12—C13—C14—C1555.0 (6)
C5—C6—C7—O3174.6 (6)O7—C14—C15—O870.1 (7)
C12—O3—C7—C867.6 (8)C13—C14—C15—O8169.8 (5)
C12—O3—C7—C6116.5 (6)O7—C14—C15—C16171.5 (6)
C6—C7—C8—O4179.7 (6)C13—C14—C15—C1651.4 (7)
O3—C7—C8—O43.9 (10)C12—O5—C16—C17177.6 (5)
C6—C7—C8—C91.3 (11)C12—O5—C16—C1561.5 (6)
O3—C7—C8—C9177.0 (6)O8—C15—C16—O5174.5 (5)
C11—O4—C8—C7176.3 (6)C14—C15—C16—O554.0 (7)
C11—O4—C8—C92.7 (11)O8—C15—C16—C1768.1 (8)
C7—C8—C9—C42.6 (11)C14—C15—C16—C17171.3 (7)
O4—C8—C9—C4178.4 (7)O5—C16—C17—O962.5 (9)
C5—C4—C9—C81.2 (10)C15—C16—C17—O9177.5 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O20.822.102.916 (7)172
O6—H6···O30.822.472.827 (5)107
O9—H9···O100.822.072.881 (8)172
O10—H18···O9i0.852.062.902 (9)172
O10—H19···O50.852.362.921 (6)124
C3—H3···O10.932.382.768 (7)105
C13—H13···O8i0.982.403.334 (8)160
C12—H12···O2ii0.982.633.538 (8)154
C16—H16···O3ii0.982.543.493 (8)163
C17—H17A···O80.972.592.938 (8)101
O8—H8···O1iii0.821.922.730 (6)168
C10—H10C···Cgi0.963.003.805 (6)142
C11—H11C···Cgii0.962.923.812 (9)155
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+3/2, y+1, z+1/2.
 

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