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

Chen, Y.; Wang, A.; Gao, H.; Niu, S.

doi:10.1107/S1600536808027839

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1901

doi:10.1107/S1600536808027839

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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

Yuzhen Chen,^a ^* Airong Wang,^b Haiyan Gao ^c and Shengyang Niu ^c

^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 ).

Experimental

Crystal data

C₂₇H₃₀O₁₄·H₂O
M_r = 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 ) T_min = 0.990, T_max = 0.995
20457 measured reflections
3332 independent reflections
2875 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O13^iv	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⋯O2^v	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027839/bt2776sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027839/bt2776Isup2.hkl

checkCIF report

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.

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

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·H₂O	F(000) = 1256
M_r = 596.53	D_x = 1.513 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5367 reflections
a = 7.2392 (14) Å	θ = 2.1–27.1°
b = 9.832 (2) Å	µ = 0.13 mm⁻¹
c = 36.782 (7) Å	T = 113 K
V = 2618.1 (9) Å³	Block, white
Z = 4	0.08 × 0.06 × 0.04 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3332 independent reflections
Radiation source: rotating anode	2875 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.090
ω scans	θ_max = 27.1°, θ_min = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −9→9
T_min = 0.990, T_max = 0.995	k = −12→12
20457 measured reflections	l = −30→47

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0614P)² + 0.0488P] where P = (F_o² + 2F_c²)/3
3332 reflections	(Δ/σ)_max = 0.001
410 parameters	Δρ_max = 0.31 e Å⁻³
10 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₇H₃₀O₁₄·H₂O	V = 2618.1 (9) Å³
M_r = 596.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.2392 (14) Å	µ = 0.13 mm⁻¹
b = 9.832 (2) Å	T = 113 K
c = 36.782 (7) Å	0.08 × 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)
T_min = 0.990, T_max = 0.995	R_int = 0.090
20457 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	10 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
3332 reflections	Δρ_min = −0.29 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.4843 (3)	0.7580 (2)	0.00818 (5)	0.0211 (5)
O2	0.5796 (3)	0.9238 (2)	0.10827 (5)	0.0185 (5)
O3	0.4249 (3)	0.3145 (2)	0.05153 (5)	0.0241 (5)
H3	0.407 (5)	0.268 (4)	0.0720 (8)	0.036*
O4	0.5902 (2)	0.6692 (2)	0.13500 (5)	0.0165 (4)
O5	0.4557 (2)	0.5220 (2)	0.17460 (5)	0.0170 (4)
O6	0.8762 (3)	0.5651 (2)	0.24894 (5)	0.0205 (4)
H6	0.909 (5)	0.502 (3)	0.2620 (8)	0.031*
O7	0.6098 (3)	0.3398 (2)	0.25491 (5)	0.0231 (5)
H7	0.622 (5)	0.364 (4)	0.2769 (7)	0.035*
O8	0.2114 (3)	0.2890 (2)	0.17453 (5)	0.0252 (5)
H8	0.140 (5)	0.342 (4)	0.1646 (9)	0.038*
O9	0.9173 (2)	0.6586 (2)	0.17330 (5)	0.0167 (4)
O10	0.9519 (2)	0.8722 (2)	0.20277 (5)	0.0163 (4)
O11	1.3189 (2)	0.8698 (2)	0.17022 (5)	0.0189 (5)
H11	1.403 (4)	0.862 (4)	0.1536 (7)	0.028*
O12	1.1740 (3)	0.8979 (2)	0.09786 (5)	0.0224 (5)
H12	1.155 (5)	0.981 (3)	0.0934 (9)	0.034*
O13	0.8811 (3)	1.0723 (2)	0.11859 (5)	0.0219 (5)
H13	0.779 (4)	1.029 (4)	0.1135 (9)	0.033*
O14	0.4369 (3)	1.1650 (2)	−0.12150 (5)	0.0212 (5)
H14	0.406 (5)	1.250 (3)	−0.1214 (9)	0.032*
O15	0.3844 (4)	0.1713 (3)	0.11315 (6)	0.0375 (6)
H15A	0.358 (6)	0.199 (5)	0.1329 (8)	0.056*
H15B	0.438 (6)	0.096 (3)	0.1150 (12)	0.056*
C2	0.5093 (4)	0.8935 (3)	0.01211 (7)	0.0173 (6)
C3	0.5473 (4)	0.9489 (3)	0.04519 (7)	0.0190 (6)
H3A	0.5692	1.0439	0.0469	0.023*
C4	0.5552 (3)	0.8674 (3)	0.07760 (7)	0.0159 (6)
C5	0.5377 (3)	0.6235 (3)	0.10095 (7)	0.0149 (6)
C6	0.4977 (4)	0.4896 (3)	0.09418 (7)	0.0168 (6)
H6A	0.4939	0.4261	0.1136	0.020*
C7	0.4621 (4)	0.4463 (3)	0.05842 (7)	0.0186 (6)
C8	0.4641 (4)	0.5371 (3)	0.02980 (7)	0.0199 (6)
H8A	0.4449	0.5074	0.0055	0.024*
C9	0.4948 (4)	0.6725 (3)	0.03761 (7)	0.0178 (6)
C13	0.5313 (4)	0.7231 (3)	0.07286 (7)	0.0146 (6)
C1''	0.6285 (4)	0.5673 (3)	0.16087 (7)	0.0150 (5)
H1''	0.6935	0.4899	0.1488	0.018*
C2''	0.7487 (3)	0.6234 (3)	0.19134 (7)	0.0154 (6)
H2''	0.6905	0.7053	0.2027	0.019*
C3''	0.7742 (4)	0.5101 (3)	0.21932 (7)	0.0167 (6)
H3''	0.8472	0.4347	0.2080	0.020*
C4''	0.5868 (4)	0.4542 (3)	0.23160 (7)	0.0167 (6)
H4''	0.5165	0.5270	0.2446	0.020*
C5''	0.4779 (4)	0.4074 (3)	0.19843 (7)	0.0158 (6)
H5''	0.5506	0.3357	0.1855	0.019*
C6''	0.2879 (4)	0.3529 (3)	0.20634 (7)	0.0203 (6)
H6''1	0.2948	0.2860	0.2264	0.024*
H6''2	0.2064	0.4283	0.2142	0.024*
C1'''	1.0404 (3)	0.7556 (3)	0.18874 (7)	0.0146 (5)
H1'''	1.1133	0.7111	0.2085	0.018*
C2'''	1.1695 (3)	0.7886 (3)	0.15686 (7)	0.0159 (6)
H2'''	1.2187	0.7025	0.1461	0.019*
C3'''	1.0581 (4)	0.8670 (3)	0.12806 (7)	0.0170 (6)
H3'''	0.9544	0.8080	0.1195	0.020*
C4'''	0.9774 (4)	0.9936 (3)	0.14530 (7)	0.0162 (6)
H4'''	1.0803	1.0497	0.1555	0.019*
C5'''	0.8485 (3)	0.9518 (3)	0.17625 (7)	0.0163 (6)
H5'''	0.7459	0.8949	0.1662	0.020*
C6'''	0.7673 (4)	1.0724 (4)	0.19609 (8)	0.0253 (7)
H6''3	0.7005	1.0407	0.2177	0.038*
H6''4	0.6819	1.1207	0.1800	0.038*
H6''5	0.8668	1.1339	0.2035	0.038*
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'	0.5297	0.8018	−0.0555	0.023*
C3'	0.4916 (4)	0.9662 (3)	−0.08794 (7)	0.0190 (6)
H3'	0.5052	0.9185	−0.1102	0.023*
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'	0.4134	1.2710	−0.0556	0.024*
C6'	0.4557 (4)	1.1065 (3)	−0.02315 (7)	0.0223 (6)
H6'	0.4439	1.1545	−0.0009	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0317 (11)	0.0152 (12)	0.0164 (9)	−0.0001 (9)	−0.0024 (8)	0.0025 (9)
O2	0.0233 (10)	0.0176 (13)	0.0144 (9)	−0.0028 (8)	−0.0018 (7)	−0.0026 (8)
O3	0.0339 (12)	0.0184 (14)	0.0201 (10)	−0.0024 (9)	−0.0012 (8)	−0.0014 (9)
O4	0.0217 (9)	0.0151 (12)	0.0126 (8)	−0.0015 (8)	−0.0021 (7)	0.0012 (8)
O5	0.0143 (8)	0.0181 (12)	0.0187 (9)	−0.0011 (8)	−0.0007 (7)	0.0047 (9)
O6	0.0237 (10)	0.0176 (12)	0.0203 (10)	−0.0044 (9)	−0.0101 (8)	0.0030 (9)
O7	0.0326 (11)	0.0202 (12)	0.0164 (9)	−0.0053 (10)	−0.0043 (8)	0.0068 (9)
O8	0.0251 (11)	0.0260 (14)	0.0246 (10)	−0.0073 (9)	−0.0074 (8)	0.0007 (10)
O9	0.0157 (9)	0.0172 (12)	0.0173 (9)	−0.0046 (8)	0.0012 (7)	−0.0033 (8)
O10	0.0179 (9)	0.0153 (12)	0.0157 (8)	0.0015 (8)	−0.0008 (7)	−0.0011 (8)
O11	0.0153 (9)	0.0239 (13)	0.0175 (9)	−0.0033 (8)	0.0003 (7)	−0.0034 (9)
O12	0.0237 (10)	0.0250 (14)	0.0184 (10)	−0.0009 (9)	0.0081 (7)	0.0021 (10)
O13	0.0227 (10)	0.0177 (13)	0.0253 (10)	−0.0020 (9)	−0.0050 (8)	0.0049 (9)
O14	0.0330 (11)	0.0170 (13)	0.0137 (9)	0.0016 (10)	−0.0006 (7)	0.0029 (9)
O15	0.0558 (16)	0.0267 (17)	0.0299 (12)	0.0115 (13)	0.0134 (11)	0.0070 (12)
C2	0.0202 (13)	0.0136 (16)	0.0182 (12)	−0.0012 (11)	0.0004 (9)	0.0007 (12)
C3	0.0242 (13)	0.0166 (17)	0.0162 (12)	−0.0025 (12)	−0.0006 (10)	0.0015 (11)
C4	0.0138 (11)	0.0179 (17)	0.0160 (12)	−0.0024 (11)	−0.0004 (9)	−0.0009 (11)
C5	0.0151 (11)	0.0162 (16)	0.0134 (11)	−0.0001 (11)	−0.0011 (9)	−0.0008 (11)
C6	0.0195 (13)	0.0152 (17)	0.0158 (13)	0.0021 (11)	−0.0011 (9)	0.0017 (12)
C7	0.0182 (12)	0.0164 (17)	0.0213 (13)	−0.0012 (11)	0.0003 (10)	−0.0029 (12)
C8	0.0267 (14)	0.0188 (18)	0.0144 (12)	0.0005 (12)	−0.0027 (10)	−0.0027 (11)
C9	0.0185 (13)	0.0200 (18)	0.0149 (12)	−0.0014 (11)	−0.0014 (9)	0.0024 (12)
C13	0.0171 (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—C2	1.352 (4)	C8—C9	1.379 (5)
O1—C9	1.373 (3)	C8—H8A	0.9500
O2—C4	1.269 (3)	C9—C13	1.414 (4)
O3—C7	1.347 (4)	C1''—C2''	1.522 (4)
O3—H3	0.89 (2)	C1''—H1''	1.0000
O4—C5	1.384 (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—H6	0.82 (2)	C4''—H4''	1.0000
O7—C4''	1.424 (4)	C5''—C6''	1.505 (4)
O7—H7	0.85 (2)	C5''—H5''	1.0000
O8—C6''	1.439 (3)	C6''—H6''1	0.9900
O8—H8	0.82 (2)	C6''—H6''2	0.9900
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—H11	0.86 (2)	C3'''—H3'''	1.0000
O12—C3'''	1.425 (3)	C4'''—C5'''	1.529 (4)
O12—H12	0.85 (3)	C4'''—H4'''	1.0000
O13—C4'''	1.432 (3)	C5'''—C6'''	1.511 (4)
O13—H13	0.87 (2)	C5'''—H5'''	1.0000
O14—C4'	1.360 (3)	C6'''—H6''3	0.9800
O14—H14	0.87 (3)	C6'''—H6''4	0.9800
O15—H15A	0.80 (3)	C6'''—H6''5	0.9800
O15—H15B	0.84 (3)	C1'—C6'	1.393 (5)
C2—C3	1.361 (4)	C1'—C2'	1.400 (4)
C2—C1'	1.472 (4)	C2'—C3'	1.379 (4)
C3—C4	1.437 (4)	C2'—H2'	0.9500
C3—H3A	0.9500	C3'—C4'	1.386 (4)
C4—C13	1.440 (4)	C3'—H3'	0.9500
C5—C6	1.371 (4)	C4'—C5'	1.403 (4)
C5—C13	1.424 (4)	C5'—C6'	1.381 (4)
C6—C7	1.406 (4)	C5'—H5'	0.9500
C6—H6A	0.9500	C6'—H6'	0.9500
C7—C8	1.381 (4)

C2—O1—C9	120.8 (2)	O5—C5''—C4''	108.0 (2)
C7—O3—H3	111 (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—H6	108 (3)	C4''—C5''—H5''	108.8
C4''—O7—H7	112 (3)	O8—C6''—C5''	110.5 (2)
C6''—O8—H8	109 (3)	O8—C6''—H6''1	109.6
C1'''—O9—C2''	120.72 (19)	C5''—C6''—H6''1	109.6
C1'''—O10—C5'''	115.13 (19)	O8—C6''—H6''2	109.6
C2'''—O11—H11	104 (2)	C5''—C6''—H6''2	109.6
C3'''—O12—H12	105 (3)	H6''1—C6''—H6''2	108.1
C4'''—O13—H13	107 (2)	O10—C1'''—O9	113.9 (2)
C4'—O14—H14	116 (2)	O10—C1'''—C2'''	112.6 (2)
H15A—O15—H15B	110 (4)	O9—C1'''—C2'''	102.6 (2)
O1—C2—C3	121.1 (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—C4	121.8 (3)	O11—C2'''—C1'''	108.4 (2)
C2—C3—H3A	119.1	O11—C2'''—C3'''	110.7 (2)
C4—C3—H3A	119.1	C1'''—C2'''—C3'''	108.2 (2)
O2—C4—C3	120.0 (3)	O11—C2'''—H2'''	109.8
O2—C4—C13	123.7 (2)	C1'''—C2'''—H2'''	109.8
C3—C4—C13	116.4 (2)	C3'''—C2'''—H2'''	109.8
C6—C5—O4	122.3 (2)	O12—C3'''—C4'''	112.2 (2)
C6—C5—C13	121.4 (2)	O12—C3'''—C2'''	109.6 (2)
O4—C5—C13	116.3 (2)	C4'''—C3'''—C2'''	109.0 (2)
C5—C6—C7	120.0 (3)	O12—C3'''—H3'''	108.7
C5—C6—H6A	120.0	C4'''—C3'''—H3'''	108.7
C7—C6—H6A	120.0	C2'''—C3'''—H3'''	108.7
O3—C7—C8	118.7 (2)	O13—C4'''—C3'''	110.2 (2)
O3—C7—C6	120.3 (3)	O13—C4'''—C5'''	111.0 (2)
C8—C7—C6	121.0 (3)	C3'''—C4'''—C5'''	109.0 (2)
C9—C8—C7	117.8 (3)	O13—C4'''—H4'''	108.9
C9—C8—H8A	121.1	C3'''—C4'''—H4'''	108.9
C7—C8—H8A	121.1	C5'''—C4'''—H4'''	108.9
O1—C9—C8	114.7 (2)	O10—C5'''—C6'''	107.3 (2)
O1—C9—C13	121.2 (3)	O10—C5'''—C4'''	109.2 (2)
C8—C9—C13	124.1 (3)	C6'''—C5'''—C4'''	112.7 (3)
C9—C13—C5	115.4 (3)	O10—C5'''—H5'''	109.2
C9—C13—C4	118.7 (2)	C6'''—C5'''—H5'''	109.2
C5—C13—C4	125.8 (2)	C4'''—C5'''—H5'''	109.2
O4—C1''—O5	106.9 (2)	C5'''—C6'''—H6''3	109.5
O4—C1''—C2''	110.6 (2)	C5'''—C6'''—H6''4	109.5
O5—C1''—C2''	110.8 (2)	H6''3—C6'''—H6''4	109.5
O4—C1''—H1''	109.5	C5'''—C6'''—H6''5	109.5
O5—C1''—H1''	109.5	H6''3—C6'''—H6''5	109.5
C2''—C1''—H1''	109.5	H6''4—C6'''—H6''5	109.5
O9—C2''—C1''	103.53 (19)	C6'—C1'—C2'	119.1 (3)
O9—C2''—C3''	112.7 (2)	C6'—C1'—C2	121.0 (2)
C1''—C2''—C3''	107.5 (2)	C2'—C1'—C2	119.9 (3)
O9—C2''—H2''	110.9	C3'—C2'—C1'	119.9 (3)
C1''—C2''—H2''	110.9	C3'—C2'—H2'	120.0
C3''—C2''—H2''	110.9	C1'—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''	109.0	O14—C4'—C3'	117.2 (2)
C2''—C3''—H3''	109.0	O14—C4'—C5'	122.9 (3)
C4''—C3''—H3''	109.0	C3'—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''	109.6	C5'—C6'—C1'	121.2 (3)
C5''—C4''—H4''	109.6	C5'—C6'—H6'	119.4
C3''—C4''—H4''	109.6	C1'—C6'—H6'	119.4
O5—C5''—C6''	107.1 (2)

C9—O1—C2—C3	0.7 (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—C4	−2.6 (4)	C1''—O5—C5''—C6''	−170.6 (2)
C1'—C2—C3—C4	177.6 (2)	C1''—O5—C5''—C4''	64.7 (3)
C2—C3—C4—O2	−175.6 (3)	O7—C4''—C5''—O5	−179.4 (2)
C2—C3—C4—C13	3.5 (4)	C3''—C4''—C5''—O5	−58.9 (3)
C1''—O4—C5—C6	9.7 (3)	O7—C4''—C5''—C6''	60.8 (3)
C1''—O4—C5—C13	−169.0 (2)	C3''—C4''—C5''—C6''	−178.6 (3)
O4—C5—C6—C7	−174.0 (2)	O5—C5''—C6''—O8	70.4 (3)
C13—C5—C6—C7	4.6 (4)	C4''—C5''—C6''—O8	−169.4 (2)
C5—C6—C7—O3	179.2 (3)	C5'''—O10—C1'''—O9	−61.0 (3)
C5—C6—C7—C8	−1.0 (4)	C5'''—O10—C1'''—C2'''	55.4 (3)
O3—C7—C8—C9	177.3 (3)	C2''—O9—C1'''—O10	−43.8 (3)
C6—C7—C8—C9	−2.5 (4)	C2''—O9—C1'''—C2'''	−165.8 (2)
C2—O1—C9—C8	179.2 (2)	O10—C1'''—C2'''—O11	66.0 (3)
C2—O1—C9—C13	0.2 (4)	O9—C1'''—C2'''—O11	−171.1 (2)
C7—C8—C9—O1	−176.4 (2)	O10—C1'''—C2'''—C3'''	−54.2 (3)
C7—C8—C9—C13	2.5 (4)	O9—C1'''—C2'''—C3'''	68.7 (3)
O1—C9—C13—C5	179.7 (2)	O11—C2'''—C3'''—O12	62.0 (3)
C8—C9—C13—C5	0.9 (4)	C1'''—C2'''—C3'''—O12	−179.3 (2)
O1—C9—C13—C4	0.8 (4)	O11—C2'''—C3'''—C4'''	−61.2 (3)
C8—C9—C13—C4	−178.1 (3)	C1'''—C2'''—C3'''—C4'''	57.5 (3)
C6—C5—C13—C9	−4.5 (4)	O12—C3'''—C4'''—O13	55.4 (3)
O4—C5—C13—C9	174.2 (2)	C2'''—C3'''—C4'''—O13	176.9 (2)
C6—C5—C13—C4	174.4 (3)	O12—C3'''—C4'''—C5'''	177.5 (2)
O4—C5—C13—C4	−6.9 (4)	C2'''—C3'''—C4'''—C5'''	−61.0 (3)
O2—C4—C13—C9	176.5 (2)	C1'''—O10—C5'''—C6'''	−179.1 (2)
C3—C4—C13—C9	−2.5 (4)	C1'''—O10—C5'''—C4'''	−56.6 (3)
O2—C4—C13—C5	−2.3 (4)	O13—C4'''—C5'''—O10	−179.9 (2)
C3—C4—C13—C5	178.7 (2)	C3'''—C4'''—C5'''—O10	58.5 (3)
C5—O4—C1''—O5	−80.2 (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''—O4	173.8 (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''—O9	−64.0 (3)	C6'—C1'—C2'—C3'	0.9 (4)
O5—C1''—C2''—O9	177.7 (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'—O14	−178.2 (2)
O9—C2''—C3''—O6	70.4 (3)	C2'—C3'—C4'—C5'	0.7 (4)
C1''—C2''—C3''—O6	−176.2 (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''—O7	−66.0 (3)	C2'—C1'—C6'—C5'	−0.3 (4)
C2''—C3''—C4''—O7	174.2 (2)	C2—C1'—C6'—C5'	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O13^iv	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···O2^v	0.84 (3)	2.00 (3)	2.820 (4)	168 (4)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) x+1, y, z; (iv) x−1/2, −y+5/2, −z; (v) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₀O₁₄·H₂O
M_r	596.53
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	7.2392 (14), 9.832 (2), 36.782 (7)
V (Å³)	2618.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.08 × 0.06 × 0.04

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.990, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	20457, 3332, 2875
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.110, 1.06
No. of reflections	3332
No. of parameters	410
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···O13^iv	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···O2^v	0.84 (3)	2.00 (3)	2.820 (4)	168 (4)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) x+1, y, z; (iv) x−1/2, −y+5/2, −z; (v) x, y−1, z.

References

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. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o1901

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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