organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

5-{(2S,3R,4S,5S,6R)-3,4-Dihydr­­oxy-6-hy­droxy­meth­yl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydr­­oxy-6-methyl­tetra­hydro­pyran-2-yl­oxy]tetra­hydro­pyran-2-yl­oxy}­-7-hydr­­oxy-2-(4-hy­droxy­phen­yl)chromen-4-one monohydrate

aDepartment of Mathematics, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, bSchool of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, and cSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China
*Correspondence e-mail: chen_yuzhen@yahoo.cn

(Received 22 August 2008; accepted 30 August 2008; online 6 September 2008)

In the title compound, C27H30O14·H2O, the hydroxy­phenyl ring makes a dihedral angle of 20.05 (11)° with the chromenone ring system. The crystal structure is stabilized by intra- and inter­molecular O—H⋯O hydrogen bonds. The absolute configuration was assigned on the basis of an analagous structure.

Related literature

For related literature, see: Li et al. (2007[Li, W., Deng, Y. L., Dai, R. J., Yu, Y. H., Saeed, M. K., Li, L., Meng, W. W. & Zhang, X. S. (2007). J. Pharm. Biomed. Anal. 45, 38-46.]).

[Scheme 1]

Experimental

Crystal data
  • C27H30O14·H2O

  • Mr = 596.53

  • Orthorhombic, P 21 21 21

  • a = 7.2392 (14) Å

  • b = 9.832 (2) Å

  • c = 36.782 (7) Å

  • V = 2618.1 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 113 (2) K

  • 0.08 × 0.06 × 0.04 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.990, Tmax = 0.995

  • 20457 measured reflections

  • 3332 independent reflections

  • 2875 reflections with I > 2σ(I)

  • Rint = 0.090

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.110

  • S = 1.05

  • 3332 reflections

  • 410 parameters

  • 10 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O15 0.89 (3) 1.80 (3) 2.684 (3) 177 (5)
O6—H6⋯O10i 0.82 (3) 2.08 (3) 2.881 (3) 166 (3)
O7—H7⋯O11i 0.85 (3) 1.99 (3) 2.817 (3) 164 (4)
O8—H8⋯O14ii 0.82 (4) 2.17 (3) 2.821 (3) 136 (3)
O11—H11⋯O2iii 0.87 (3) 2.19 (3) 3.006 (3) 158 (3)
O13—H13⋯O2 0.87 (3) 1.79 (3) 2.653 (3) 172 (3)
O14—H14⋯O13iv 0.87 (3) 1.76 (3) 2.617 (3) 170 (3)
O15—H15A⋯O8 0.80 (3) 2.06 (4) 2.829 (3) 161 (4)
O15—H15B⋯O2v 0.84 (3) 2.00 (3) 2.820 (4) 168 (4)
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (iii) x+1, y, z; (iv) [x-{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]; (v) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2005[Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

The title compound was prepared from compound (II) by hydrolysis (scheme 2).

The hydroxyphenyl ring makes a dihedral angle of 20.05 (11)° with the benzopyranone ring. The two saturated rings adopt chair configurations. The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds (Table 1), with O···O distances in the range 2.617 (3)–3.006 (3) Å.

Related literature top

For related literature, see: Li et al. (2007).

Experimental top

Compound (II) was mixed with methanol and K2CO3. After stirring for 60 min at 40°C, hydrochloric acid was added to make pH 7.0. The mixture was kept for 24 h at 4°C. The resultant white precipitate was separated by filtration, washed with water and dried for X-ray analysis.

Refinement top

In the absence of anomalous scatterers Friedel pairs were merged. The absolute configuration was set according to the literature (Li et al., 2007). The O-bound H atoms were located in a difference map and refined with the restraint O—H = 0.85 (3) Å. All other H atoms were positioned geometrically and refined as riding atoms, with Uiso(H) = 1.2 Ueq(CH and CH2) and C—H ranging from 0.95–1.0Å or Uiso(H) = 1.5 Ueq(CH3) and Cmethyl—H = 0.99 Å.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme and 50% probability displacement ellipsoids. The dashed lines indicates H-bonds.
5-{(2S,3R,4S,5S,6R)-3,4-Dihydroxy-6- hydroxymethyl-3-[(2S,3R,4R,5R,6S)-3,4,5- trihydroxy-6-methyltetrahydropyran-2-yloxy]tetrahydropyran-2-yloxy}-7-hydroxy- 2-(4-hydroxyphenyl)chromen-4-one monohydrate top
Crystal data top
C27H30O14·H2OF(000) = 1256
Mr = 596.53Dx = 1.513 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5367 reflections
a = 7.2392 (14) Åθ = 2.1–27.1°
b = 9.832 (2) ŵ = 0.13 mm1
c = 36.782 (7) ÅT = 113 K
V = 2618.1 (9) Å3Block, white
Z = 40.08 × 0.06 × 0.04 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3332 independent reflections
Radiation source: rotating anode2875 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.090
ω scansθmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
h = 99
Tmin = 0.990, Tmax = 0.995k = 1212
20457 measured reflectionsl = 3047
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0614P)2 + 0.0488P]
where P = (Fo2 + 2Fc2)/3
3332 reflections(Δ/σ)max = 0.001
410 parametersΔρmax = 0.31 e Å3
10 restraintsΔρmin = 0.29 e Å3
Crystal data top
C27H30O14·H2OV = 2618.1 (9) Å3
Mr = 596.53Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.2392 (14) ŵ = 0.13 mm1
b = 9.832 (2) ÅT = 113 K
c = 36.782 (7) Å0.08 × 0.06 × 0.04 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
3332 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2875 reflections with I > 2σ(I)
Tmin = 0.990, Tmax = 0.995Rint = 0.090
20457 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04510 restraints
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.31 e Å3
3332 reflectionsΔρmin = 0.29 e Å3
410 parameters
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
xyzUiso*/Ueq
O10.4843 (3)0.7580 (2)0.00818 (5)0.0211 (5)
O20.5796 (3)0.9238 (2)0.10827 (5)0.0185 (5)
O30.4249 (3)0.3145 (2)0.05153 (5)0.0241 (5)
H30.407 (5)0.268 (4)0.0720 (8)0.036*
O40.5902 (2)0.6692 (2)0.13500 (5)0.0165 (4)
O50.4557 (2)0.5220 (2)0.17460 (5)0.0170 (4)
O60.8762 (3)0.5651 (2)0.24894 (5)0.0205 (4)
H60.909 (5)0.502 (3)0.2620 (8)0.031*
O70.6098 (3)0.3398 (2)0.25491 (5)0.0231 (5)
H70.622 (5)0.364 (4)0.2769 (7)0.035*
O80.2114 (3)0.2890 (2)0.17453 (5)0.0252 (5)
H80.140 (5)0.342 (4)0.1646 (9)0.038*
O90.9173 (2)0.6586 (2)0.17330 (5)0.0167 (4)
O100.9519 (2)0.8722 (2)0.20277 (5)0.0163 (4)
O111.3189 (2)0.8698 (2)0.17022 (5)0.0189 (5)
H111.403 (4)0.862 (4)0.1536 (7)0.028*
O121.1740 (3)0.8979 (2)0.09786 (5)0.0224 (5)
H121.155 (5)0.981 (3)0.0934 (9)0.034*
O130.8811 (3)1.0723 (2)0.11859 (5)0.0219 (5)
H130.779 (4)1.029 (4)0.1135 (9)0.033*
O140.4369 (3)1.1650 (2)0.12150 (5)0.0212 (5)
H140.406 (5)1.250 (3)0.1214 (9)0.032*
O150.3844 (4)0.1713 (3)0.11315 (6)0.0375 (6)
H15A0.358 (6)0.199 (5)0.1329 (8)0.056*
H15B0.438 (6)0.096 (3)0.1150 (12)0.056*
C20.5093 (4)0.8935 (3)0.01211 (7)0.0173 (6)
C30.5473 (4)0.9489 (3)0.04519 (7)0.0190 (6)
H3A0.56921.04390.04690.023*
C40.5552 (3)0.8674 (3)0.07760 (7)0.0159 (6)
C50.5377 (3)0.6235 (3)0.10095 (7)0.0149 (6)
C60.4977 (4)0.4896 (3)0.09418 (7)0.0168 (6)
H6A0.49390.42610.11360.020*
C70.4621 (4)0.4463 (3)0.05842 (7)0.0186 (6)
C80.4641 (4)0.5371 (3)0.02980 (7)0.0199 (6)
H8A0.44490.50740.00550.024*
C90.4948 (4)0.6725 (3)0.03761 (7)0.0178 (6)
C130.5313 (4)0.7231 (3)0.07286 (7)0.0146 (6)
C1''0.6285 (4)0.5673 (3)0.16087 (7)0.0150 (5)
H1''0.69350.48990.14880.018*
C2''0.7487 (3)0.6234 (3)0.19134 (7)0.0154 (6)
H2''0.69050.70530.20270.019*
C3''0.7742 (4)0.5101 (3)0.21932 (7)0.0167 (6)
H3''0.84720.43470.20800.020*
C4''0.5868 (4)0.4542 (3)0.23160 (7)0.0167 (6)
H4''0.51650.52700.24460.020*
C5''0.4779 (4)0.4074 (3)0.19843 (7)0.0158 (6)
H5''0.55060.33570.18550.019*
C6''0.2879 (4)0.3529 (3)0.20634 (7)0.0203 (6)
H6''10.29480.28600.22640.024*
H6''20.20640.42830.21420.024*
C1'''1.0404 (3)0.7556 (3)0.18874 (7)0.0146 (5)
H1'''1.11330.71110.20850.018*
C2'''1.1695 (3)0.7886 (3)0.15686 (7)0.0159 (6)
H2'''1.21870.70250.14610.019*
C3'''1.0581 (4)0.8670 (3)0.12806 (7)0.0170 (6)
H3'''0.95440.80800.11950.020*
C4'''0.9774 (4)0.9936 (3)0.14530 (7)0.0162 (6)
H4'''1.08031.04970.15550.019*
C5'''0.8485 (3)0.9518 (3)0.17625 (7)0.0163 (6)
H5'''0.74590.89490.16620.020*
C6'''0.7673 (4)1.0724 (4)0.19609 (8)0.0253 (7)
H6''30.70051.04070.21770.038*
H6''40.68191.12070.18000.038*
H6''50.86681.13390.20350.038*
C1'0.4910 (4)0.9672 (3)0.02252 (7)0.0182 (6)
C2'0.5075 (4)0.8970 (3)0.05549 (7)0.0192 (6)
H2'0.52970.80180.05550.023*
C3'0.4916 (4)0.9662 (3)0.08794 (7)0.0190 (6)
H3'0.50520.91850.11020.023*
C4'0.4559 (4)1.1048 (3)0.08840 (7)0.0179 (6)
C5'0.4378 (4)1.1761 (3)0.05556 (7)0.0202 (6)
H5'0.41341.27100.05560.024*
C6'0.4557 (4)1.1065 (3)0.02315 (7)0.0223 (6)
H6'0.44391.15450.00090.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0317 (11)0.0152 (12)0.0164 (9)0.0001 (9)0.0024 (8)0.0025 (9)
O20.0233 (10)0.0176 (13)0.0144 (9)0.0028 (8)0.0018 (7)0.0026 (8)
O30.0339 (12)0.0184 (14)0.0201 (10)0.0024 (9)0.0012 (8)0.0014 (9)
O40.0217 (9)0.0151 (12)0.0126 (8)0.0015 (8)0.0021 (7)0.0012 (8)
O50.0143 (8)0.0181 (12)0.0187 (9)0.0011 (8)0.0007 (7)0.0047 (9)
O60.0237 (10)0.0176 (12)0.0203 (10)0.0044 (9)0.0101 (8)0.0030 (9)
O70.0326 (11)0.0202 (12)0.0164 (9)0.0053 (10)0.0043 (8)0.0068 (9)
O80.0251 (11)0.0260 (14)0.0246 (10)0.0073 (9)0.0074 (8)0.0007 (10)
O90.0157 (9)0.0172 (12)0.0173 (9)0.0046 (8)0.0012 (7)0.0033 (8)
O100.0179 (9)0.0153 (12)0.0157 (8)0.0015 (8)0.0008 (7)0.0011 (8)
O110.0153 (9)0.0239 (13)0.0175 (9)0.0033 (8)0.0003 (7)0.0034 (9)
O120.0237 (10)0.0250 (14)0.0184 (10)0.0009 (9)0.0081 (7)0.0021 (10)
O130.0227 (10)0.0177 (13)0.0253 (10)0.0020 (9)0.0050 (8)0.0049 (9)
O140.0330 (11)0.0170 (13)0.0137 (9)0.0016 (10)0.0006 (7)0.0029 (9)
O150.0558 (16)0.0267 (17)0.0299 (12)0.0115 (13)0.0134 (11)0.0070 (12)
C20.0202 (13)0.0136 (16)0.0182 (12)0.0012 (11)0.0004 (9)0.0007 (12)
C30.0242 (13)0.0166 (17)0.0162 (12)0.0025 (12)0.0006 (10)0.0015 (11)
C40.0138 (11)0.0179 (17)0.0160 (12)0.0024 (11)0.0004 (9)0.0009 (11)
C50.0151 (11)0.0162 (16)0.0134 (11)0.0001 (11)0.0011 (9)0.0008 (11)
C60.0195 (13)0.0152 (17)0.0158 (13)0.0021 (11)0.0011 (9)0.0017 (12)
C70.0182 (12)0.0164 (17)0.0213 (13)0.0012 (11)0.0003 (10)0.0029 (12)
C80.0267 (14)0.0188 (18)0.0144 (12)0.0005 (12)0.0027 (10)0.0027 (11)
C90.0185 (13)0.0200 (18)0.0149 (12)0.0014 (11)0.0014 (9)0.0024 (12)
C130.0171 (12)0.0136 (16)0.0132 (12)0.0003 (11)0.0008 (9)0.0007 (11)
C1''0.0172 (12)0.0134 (15)0.0143 (11)0.0002 (11)0.0005 (9)0.0013 (11)
C2''0.0155 (12)0.0155 (17)0.0153 (12)0.0021 (11)0.0009 (9)0.0001 (11)
C3''0.0189 (13)0.0154 (17)0.0160 (12)0.0011 (11)0.0039 (9)0.0017 (11)
C4''0.0195 (12)0.0155 (16)0.0152 (12)0.0018 (11)0.0010 (9)0.0017 (11)
C5''0.0210 (13)0.0121 (16)0.0143 (12)0.0006 (11)0.0006 (9)0.0025 (11)
C6''0.0195 (12)0.0228 (18)0.0186 (13)0.0053 (13)0.0021 (9)0.0022 (13)
C1'''0.0147 (11)0.0114 (15)0.0178 (12)0.0007 (11)0.0007 (9)0.0048 (11)
C2'''0.0144 (12)0.0152 (16)0.0180 (12)0.0025 (10)0.0013 (9)0.0028 (11)
C3'''0.0166 (12)0.0195 (17)0.0150 (12)0.0038 (11)0.0007 (9)0.0019 (11)
C4'''0.0177 (12)0.0156 (17)0.0152 (12)0.0002 (11)0.0028 (9)0.0046 (11)
C5'''0.0149 (12)0.0163 (16)0.0178 (12)0.0005 (11)0.0001 (9)0.0009 (12)
C6'''0.0255 (14)0.025 (2)0.0250 (14)0.0081 (13)0.0017 (11)0.0009 (13)
C1'0.0202 (13)0.0202 (18)0.0142 (12)0.0015 (12)0.0005 (9)0.0013 (12)
C2'0.0243 (14)0.0163 (17)0.0172 (13)0.0023 (12)0.0004 (10)0.0006 (12)
C3'0.0264 (14)0.0153 (17)0.0153 (12)0.0019 (12)0.0007 (10)0.0023 (11)
C4'0.0192 (12)0.0196 (17)0.0149 (12)0.0013 (12)0.0005 (9)0.0018 (12)
C5'0.0306 (15)0.0114 (17)0.0186 (13)0.0010 (12)0.0000 (11)0.0017 (12)
C6'0.0328 (15)0.0180 (18)0.0159 (13)0.0025 (13)0.0010 (11)0.0031 (12)
Geometric parameters (Å, º) top
O1—C21.352 (4)C8—C91.379 (5)
O1—C91.373 (3)C8—H8A0.9500
O2—C41.269 (3)C9—C131.414 (4)
O3—C71.347 (4)C1''—C2''1.522 (4)
O3—H30.89 (2)C1''—H1''1.0000
O4—C51.384 (3)C2''—C3''1.528 (4)
O4—C1''1.409 (3)C2''—H2''1.0000
O5—C1''1.420 (3)C3''—C4''1.532 (4)
O5—C5''1.436 (3)C3''—H3''1.0000
O6—C3''1.423 (3)C4''—C5''1.524 (3)
O6—H60.82 (2)C4''—H4''1.0000
O7—C4''1.424 (4)C5''—C6''1.505 (4)
O7—H70.85 (2)C5''—H5''1.0000
O8—C6''1.439 (3)C6''—H6''10.9900
O8—H80.82 (2)C6''—H6''20.9900
O9—C1'''1.423 (3)C1'''—C2'''1.534 (4)
O9—C2''1.432 (3)C1'''—H1'''1.0000
O10—C1'''1.412 (3)C2'''—C3'''1.539 (4)
O10—C5'''1.457 (3)C2'''—H2'''1.0000
O11—C2'''1.431 (3)C3'''—C4'''1.514 (4)
O11—H110.86 (2)C3'''—H3'''1.0000
O12—C3'''1.425 (3)C4'''—C5'''1.529 (4)
O12—H120.85 (3)C4'''—H4'''1.0000
O13—C4'''1.432 (3)C5'''—C6'''1.511 (4)
O13—H130.87 (2)C5'''—H5'''1.0000
O14—C4'1.360 (3)C6'''—H6''30.9800
O14—H140.87 (3)C6'''—H6''40.9800
O15—H15A0.80 (3)C6'''—H6''50.9800
O15—H15B0.84 (3)C1'—C6'1.393 (5)
C2—C31.361 (4)C1'—C2'1.400 (4)
C2—C1'1.472 (4)C2'—C3'1.379 (4)
C3—C41.437 (4)C2'—H2'0.9500
C3—H3A0.9500C3'—C4'1.386 (4)
C4—C131.440 (4)C3'—H3'0.9500
C5—C61.371 (4)C4'—C5'1.403 (4)
C5—C131.424 (4)C5'—C6'1.381 (4)
C6—C71.406 (4)C5'—H5'0.9500
C6—H6A0.9500C6'—H6'0.9500
C7—C81.381 (4)
C2—O1—C9120.8 (2)O5—C5''—C4''108.0 (2)
C7—O3—H3111 (2)C6''—C5''—C4''115.2 (2)
C5—O4—C1''115.7 (2)O5—C5''—H5''108.8
C1''—O5—C5''111.37 (19)C6''—C5''—H5''108.8
C3''—O6—H6108 (3)C4''—C5''—H5''108.8
C4''—O7—H7112 (3)O8—C6''—C5''110.5 (2)
C6''—O8—H8109 (3)O8—C6''—H6''1109.6
C1'''—O9—C2''120.72 (19)C5''—C6''—H6''1109.6
C1'''—O10—C5'''115.13 (19)O8—C6''—H6''2109.6
C2'''—O11—H11104 (2)C5''—C6''—H6''2109.6
C3'''—O12—H12105 (3)H6''1—C6''—H6''2108.1
C4'''—O13—H13107 (2)O10—C1'''—O9113.9 (2)
C4'—O14—H14116 (2)O10—C1'''—C2'''112.6 (2)
H15A—O15—H15B110 (4)O9—C1'''—C2'''102.6 (2)
O1—C2—C3121.1 (3)O10—C1'''—H1'''109.2
O1—C2—C1'112.4 (2)O9—C1'''—H1'''109.2
C3—C2—C1'126.5 (3)C2'''—C1'''—H1'''109.2
C2—C3—C4121.8 (3)O11—C2'''—C1'''108.4 (2)
C2—C3—H3A119.1O11—C2'''—C3'''110.7 (2)
C4—C3—H3A119.1C1'''—C2'''—C3'''108.2 (2)
O2—C4—C3120.0 (3)O11—C2'''—H2'''109.8
O2—C4—C13123.7 (2)C1'''—C2'''—H2'''109.8
C3—C4—C13116.4 (2)C3'''—C2'''—H2'''109.8
C6—C5—O4122.3 (2)O12—C3'''—C4'''112.2 (2)
C6—C5—C13121.4 (2)O12—C3'''—C2'''109.6 (2)
O4—C5—C13116.3 (2)C4'''—C3'''—C2'''109.0 (2)
C5—C6—C7120.0 (3)O12—C3'''—H3'''108.7
C5—C6—H6A120.0C4'''—C3'''—H3'''108.7
C7—C6—H6A120.0C2'''—C3'''—H3'''108.7
O3—C7—C8118.7 (2)O13—C4'''—C3'''110.2 (2)
O3—C7—C6120.3 (3)O13—C4'''—C5'''111.0 (2)
C8—C7—C6121.0 (3)C3'''—C4'''—C5'''109.0 (2)
C9—C8—C7117.8 (3)O13—C4'''—H4'''108.9
C9—C8—H8A121.1C3'''—C4'''—H4'''108.9
C7—C8—H8A121.1C5'''—C4'''—H4'''108.9
O1—C9—C8114.7 (2)O10—C5'''—C6'''107.3 (2)
O1—C9—C13121.2 (3)O10—C5'''—C4'''109.2 (2)
C8—C9—C13124.1 (3)C6'''—C5'''—C4'''112.7 (3)
C9—C13—C5115.4 (3)O10—C5'''—H5'''109.2
C9—C13—C4118.7 (2)C6'''—C5'''—H5'''109.2
C5—C13—C4125.8 (2)C4'''—C5'''—H5'''109.2
O4—C1''—O5106.9 (2)C5'''—C6'''—H6''3109.5
O4—C1''—C2''110.6 (2)C5'''—C6'''—H6''4109.5
O5—C1''—C2''110.8 (2)H6''3—C6'''—H6''4109.5
O4—C1''—H1''109.5C5'''—C6'''—H6''5109.5
O5—C1''—H1''109.5H6''3—C6'''—H6''5109.5
C2''—C1''—H1''109.5H6''4—C6'''—H6''5109.5
O9—C2''—C1''103.53 (19)C6'—C1'—C2'119.1 (3)
O9—C2''—C3''112.7 (2)C6'—C1'—C2121.0 (2)
C1''—C2''—C3''107.5 (2)C2'—C1'—C2119.9 (3)
O9—C2''—H2''110.9C3'—C2'—C1'119.9 (3)
C1''—C2''—H2''110.9C3'—C2'—H2'120.0
C3''—C2''—H2''110.9C1'—C2'—H2'120.0
O6—C3''—C2''107.5 (2)C2'—C3'—C4'120.7 (3)
O6—C3''—C4''111.7 (2)C2'—C3'—H3'119.6
C2''—C3''—C4''110.7 (2)C4'—C3'—H3'119.6
O6—C3''—H3''109.0O14—C4'—C3'117.2 (2)
C2''—C3''—H3''109.0O14—C4'—C5'122.9 (3)
C4''—C3''—H3''109.0C3'—C4'—C5'119.9 (3)
O7—C4''—C5''107.7 (2)C6'—C5'—C4'119.2 (3)
O7—C4''—C3''110.9 (2)C6'—C5'—H5'120.4
C5''—C4''—C3''109.3 (2)C4'—C5'—H5'120.4
O7—C4''—H4''109.6C5'—C6'—C1'121.2 (3)
C5''—C4''—H4''109.6C5'—C6'—H6'119.4
C3''—C4''—H4''109.6C1'—C6'—H6'119.4
O5—C5''—C6''107.1 (2)
C9—O1—C2—C30.7 (4)O6—C3''—C4''—C5''175.5 (2)
C9—O1—C2—C1'179.5 (2)C2''—C3''—C4''—C5''55.7 (3)
O1—C2—C3—C42.6 (4)C1''—O5—C5''—C6''170.6 (2)
C1'—C2—C3—C4177.6 (2)C1''—O5—C5''—C4''64.7 (3)
C2—C3—C4—O2175.6 (3)O7—C4''—C5''—O5179.4 (2)
C2—C3—C4—C133.5 (4)C3''—C4''—C5''—O558.9 (3)
C1''—O4—C5—C69.7 (3)O7—C4''—C5''—C6''60.8 (3)
C1''—O4—C5—C13169.0 (2)C3''—C4''—C5''—C6''178.6 (3)
O4—C5—C6—C7174.0 (2)O5—C5''—C6''—O870.4 (3)
C13—C5—C6—C74.6 (4)C4''—C5''—C6''—O8169.4 (2)
C5—C6—C7—O3179.2 (3)C5'''—O10—C1'''—O961.0 (3)
C5—C6—C7—C81.0 (4)C5'''—O10—C1'''—C2'''55.4 (3)
O3—C7—C8—C9177.3 (3)C2''—O9—C1'''—O1043.8 (3)
C6—C7—C8—C92.5 (4)C2''—O9—C1'''—C2'''165.8 (2)
C2—O1—C9—C8179.2 (2)O10—C1'''—C2'''—O1166.0 (3)
C2—O1—C9—C130.2 (4)O9—C1'''—C2'''—O11171.1 (2)
C7—C8—C9—O1176.4 (2)O10—C1'''—C2'''—C3'''54.2 (3)
C7—C8—C9—C132.5 (4)O9—C1'''—C2'''—C3'''68.7 (3)
O1—C9—C13—C5179.7 (2)O11—C2'''—C3'''—O1262.0 (3)
C8—C9—C13—C50.9 (4)C1'''—C2'''—C3'''—O12179.3 (2)
O1—C9—C13—C40.8 (4)O11—C2'''—C3'''—C4'''61.2 (3)
C8—C9—C13—C4178.1 (3)C1'''—C2'''—C3'''—C4'''57.5 (3)
C6—C5—C13—C94.5 (4)O12—C3'''—C4'''—O1355.4 (3)
O4—C5—C13—C9174.2 (2)C2'''—C3'''—C4'''—O13176.9 (2)
C6—C5—C13—C4174.4 (3)O12—C3'''—C4'''—C5'''177.5 (2)
O4—C5—C13—C46.9 (4)C2'''—C3'''—C4'''—C5'''61.0 (3)
O2—C4—C13—C9176.5 (2)C1'''—O10—C5'''—C6'''179.1 (2)
C3—C4—C13—C92.5 (4)C1'''—O10—C5'''—C4'''56.6 (3)
O2—C4—C13—C52.3 (4)O13—C4'''—C5'''—O10179.9 (2)
C3—C4—C13—C5178.7 (2)C3'''—C4'''—C5'''—O1058.5 (3)
C5—O4—C1''—O580.2 (3)O13—C4'''—C5'''—C6'''60.8 (3)
C5—O4—C1''—C2''159.1 (2)C3'''—C4'''—C5'''—C6'''177.7 (2)
C5''—O5—C1''—O4173.8 (2)O1—C2—C1'—C6'160.3 (3)
C5''—O5—C1''—C2''65.7 (3)C3—C2—C1'—C6'19.9 (4)
C1'''—O9—C2''—C1''158.0 (2)O1—C2—C1'—C2'19.2 (3)
C1'''—O9—C2''—C3''86.2 (3)C3—C2—C1'—C2'160.6 (3)
O4—C1''—C2''—O964.0 (3)C6'—C1'—C2'—C3'0.9 (4)
O5—C1''—C2''—O9177.7 (2)C2—C1'—C2'—C3'179.6 (3)
O4—C1''—C2''—C3''176.6 (2)C1'—C2'—C3'—C4'1.1 (4)
O5—C1''—C2''—C3''58.3 (3)C2'—C3'—C4'—O14178.2 (2)
O9—C2''—C3''—O670.4 (3)C2'—C3'—C4'—C5'0.7 (4)
C1''—C2''—C3''—O6176.2 (2)O14—C4'—C5'—C6'178.8 (3)
O9—C2''—C3''—C4''167.4 (2)C3'—C4'—C5'—C6'0.0 (4)
C1''—C2''—C3''—C4''53.9 (3)C4'—C5'—C6'—C1'0.2 (4)
O6—C3''—C4''—O766.0 (3)C2'—C1'—C6'—C5'0.3 (4)
C2''—C3''—C4''—O7174.2 (2)C2—C1'—C6'—C5'179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O150.89 (3)1.80 (3)2.684 (3)177 (5)
O6—H6···O10i0.82 (3)2.08 (3)2.881 (3)166 (3)
O7—H7···O11i0.85 (3)1.99 (3)2.817 (3)164 (4)
O8—H8···O14ii0.82 (4)2.17 (3)2.821 (3)136 (3)
O11—H11···O2iii0.87 (3)2.19 (3)3.006 (3)158 (3)
O13—H13···O20.87 (3)1.79 (3)2.653 (3)172 (3)
O14—H14···O13iv0.87 (3)1.76 (3)2.617 (3)170 (3)
O15—H15A···O80.80 (3)2.06 (4)2.829 (3)161 (4)
O15—H15B···O2v0.84 (3)2.00 (3)2.820 (4)168 (4)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x1/2, y+3/2, z; (iii) x+1, y, z; (iv) x1/2, y+5/2, z; (v) x, y1, z.

Experimental details

Crystal data
Chemical formulaC27H30O14·H2O
Mr596.53
Crystal system, space groupOrthorhombic, P212121
Temperature (K)113
a, b, c (Å)7.2392 (14), 9.832 (2), 36.782 (7)
V3)2618.1 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.08 × 0.06 × 0.04
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.990, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
20457, 3332, 2875
Rint0.090
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.110, 1.06
No. of reflections3332
No. of parameters410
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.29

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O150.89 (3)1.80 (3)2.684 (3)177 (5)
O6—H6···O10i0.82 (3)2.08 (3)2.881 (3)166 (3)
O7—H7···O11i0.85 (3)1.99 (3)2.817 (3)164 (4)
O8—H8···O14ii0.82 (4)2.17 (3)2.821 (3)136 (3)
O11—H11···O2iii0.87 (3)2.19 (3)3.006 (3)158 (3)
O13—H13···O20.87 (3)1.79 (3)2.653 (3)172 (3)
O14—H14···O13iv0.87 (3)1.76 (3)2.617 (3)170 (3)
O15—H15A···O80.80 (3)2.06 (4)2.829 (3)161 (4)
O15—H15B···O2v0.84 (3)2.00 (3)2.820 (4)168 (4)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x1/2, y+3/2, z; (iii) x+1, y, z; (iv) x1/2, y+5/2, z; (v) x, y1, z.
 

References

First citationLi, W., Deng, Y. L., Dai, R. J., Yu, Y. H., Saeed, M. K., Li, L., Meng, W. W. & Zhang, X. S. (2007). J. Pharm. Biomed. Anal. 45, 38–46.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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