(1S,3aR,4S,6aR)-1-(4-Hydr­oxy-3-methoxy­phen­yl)-4-(4-hydr­oxy-3-methyl­phen­yl)perhydro­furo[3,4-c]furan-3a,6a-diol hexa­hydrate

In the title compound, C₂₀H₂₂O₈·6H₂O, the asymmetric unit contains one half-mol­ecule with the other half generated by a crystallographic twofold axis of symmetry. It was extracted from the leaves of Prinsepia utilis Royle and displays powerful anti-oxidant activity.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 77%
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.129
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact  O8     ..  O9      ..       1.94 Ang.

Author Response: The independent unit contained three H~2~O molecule, in which two H~2~O were disordered in five position[occupancies: 0.64(10), 0.69(7), 0.36(10), 0.18(7) and 0.13(9)].

Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       1.25 Sigma
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O9      ..       2.77 Ang.

Author Response: The independent unit contained three H~2~O molecule, in which two H~2~O were disordered in five position[occupancies: 0.64(10), 0.69(7), 0.36(10), 0.18(7) and 0.13(9)].

PLAT430_ALERT_2_B Short Inter D...A Contact  O8     ..  O9      ..       2.70 Ang.

Author Response: The independent unit contained three H~2~O molecule, in which two H~2~O were disordered in five position[occupancies: 0.64(10), 0.69(7), 0.36(10), 0.18(7) and 0.13(9)].

PLAT728_ALERT_1_B D-H..A  Calc      161.00, Rep      164.00 Dev...       3.00 Deg.
              O5   -H5B  -O5      1.555   1.555   2.665

Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    2
           From the CIF: _chemical_formula_weight           498.47
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   20.00  240.22
           H         1.01   26.00   26.21
           O        16.00   14.00  223.99
           Calculated formula weight              490.41
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     498.47
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      40.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        >O6
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        <O7
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        >O8
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O10
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1     ..  H5C     ..       2.12 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.24 Ratio

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C20 H34 O14
            Atom count from the _atom_site data:  C20 H26 O14
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C20 H34 O14
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         40.00     40.00    0.00
           H         68.00     52.00   16.00
           O         28.00     28.00    0.00
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           27.99
           From the CIF: _reflns_number_total               1692
           Count of symmetry unique reflns         1692
           Completeness (_total/calc)            100.00%
           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

   1 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

(1S,3aR,4S,6aR)-1-(4-Hydroxy-3-methoxyphenyl)-4-(4-hydroxy-3- methylphenyl)perhydrofuro[3,4-c]furan-3a,6a-diol hexahydrate

Crystal data

C20H22O8·6H2O	Dx = 1.385 Mg m^−3
Mr = 498.47	Melting point: 464 K
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 1916 reflections
a = 19.060 (3) Å	θ = 2.4–22.1°
b = 6.6887 (11) Å	µ = 0.12 mm^−1
c = 9.3752 (16) Å	T = 293 K
V = 1195.2 (3) Å^3	Block, colorless
Z = 2	0.26 × 0.20 × 0.16 mm
F(000) = 532

Data collection

Bruker SMART CCD area-detector diffractometer	1692 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→25
Tmin = 0.972, Tmax = 0.981	k = −6→8
7991 measured reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0873P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1692 reflections	Δρmax = 0.29 e Å^−3
180 parameters	Δρmin = −0.17 e Å^−3
26 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.005 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.57200 (9)	−0.0150 (3)	0.54951 (18)	0.0413 (4)
H1	0.5647	0.0973	0.5813	0.062*
O2	0.53417 (9)	0.2899 (3)	0.3207 (3)	0.0538 (6)
O3	0.80982 (10)	−0.1064 (3)	0.1754 (2)	0.0585 (6)
O4	0.86476 (10)	0.1889 (3)	0.3122 (2)	0.0560 (6)
H4	0.8778	0.2825	0.3621	0.084*
C1	0.53866 (11)	−0.0350 (3)	0.4157 (3)	0.0333 (5)
C2	0.56984 (12)	0.1033 (4)	0.3014 (3)	0.0377 (5)
H2	0.5579	0.0501	0.2071	0.045*
C3	0.46530 (12)	0.2548 (3)	0.3725 (3)	0.0411 (6)
H3A	0.4310	0.2835	0.2989	0.049*
H3B	0.4557	0.3398	0.4541	0.049*
C4	0.64807 (12)	0.1340 (4)	0.3086 (3)	0.0365 (6)
C5	0.69101 (12)	−0.0014 (4)	0.2366 (2)	0.0378 (5)
H5	0.6710	−0.1052	0.1846	0.045*
C6	0.76321 (12)	0.0182 (4)	0.2422 (3)	0.0387 (6)
C7	0.79302 (12)	0.1769 (4)	0.3159 (3)	0.0399 (6)
C8	0.75083 (14)	0.3090 (4)	0.3883 (3)	0.0453 (6)
H8	0.7708	0.4133	0.4399	0.054*
C9	0.67844 (14)	0.2873 (4)	0.3848 (3)	0.0432 (6)
H9	0.6502	0.3770	0.4343	0.052*
C10	0.7839 (2)	−0.2778 (5)	0.1071 (5)	0.0812 (12)
H10A	0.7575	−0.3563	0.1740	0.122*
H10B	0.8223	−0.3555	0.0711	0.122*
H10C	0.7540	−0.2388	0.0295	0.122*
O5	0.54786 (11)	0.3290 (4)	0.6988 (3)	0.0674 (7)
H5A	0.5867	0.3902	0.7085	0.101*
H5B	0.5144	0.4113	0.6861	0.101*	0.50
H5C	0.5395	0.2555	0.7708	0.101*	0.50
O6	0.4024 (3)	0.4278 (11)	0.0544 (6)	0.119 (3)	0.638 (10)
O7	0.4125 (7)	0.228 (3)	−0.0280 (16)	0.161 (6)*	0.362 (10)
O8	0.4870 (5)	0.8078 (12)	0.9560 (6)	0.159 (3)	0.692 (7)
O9	0.4686 (11)	0.553 (3)	0.048 (2)	0.117 (8)	0.183 (7)
O10	0.5000	1.0000	0.900 (3)	0.148 (9)	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0329 (8)	0.0415 (9)	0.0496 (10)	0.0059 (8)	−0.0074 (8)	0.0017 (8)
O2	0.0320 (9)	0.0332 (9)	0.0962 (16)	0.0041 (7)	0.0069 (9)	0.0187 (10)
O3	0.0347 (10)	0.0622 (12)	0.0787 (14)	0.0002 (9)	0.0040 (10)	−0.0301 (11)
O4	0.0291 (9)	0.0608 (12)	0.0781 (15)	−0.0083 (8)	−0.0033 (9)	−0.0216 (12)
C1	0.0234 (11)	0.0276 (11)	0.0488 (14)	0.0014 (9)	−0.0015 (9)	−0.0010 (9)
C2	0.0280 (11)	0.0385 (12)	0.0465 (13)	0.0015 (10)	−0.0003 (10)	0.0029 (11)
C3	0.0302 (13)	0.0297 (11)	0.0633 (17)	0.0031 (9)	0.0008 (11)	0.0015 (11)
C4	0.0276 (11)	0.0368 (12)	0.0451 (14)	−0.0028 (10)	0.0002 (10)	0.0032 (11)
C5	0.0320 (11)	0.0414 (12)	0.0401 (12)	−0.0066 (10)	−0.0017 (10)	−0.0043 (11)
C6	0.0337 (11)	0.0407 (12)	0.0417 (13)	−0.0010 (10)	0.0027 (10)	−0.0044 (11)
C7	0.0281 (12)	0.0443 (13)	0.0474 (14)	−0.0057 (10)	−0.0027 (10)	−0.0021 (13)
C8	0.0406 (14)	0.0386 (12)	0.0568 (17)	−0.0078 (11)	−0.0015 (12)	−0.0088 (12)
C9	0.0353 (13)	0.0373 (13)	0.0569 (16)	0.0000 (11)	0.0046 (12)	−0.0067 (12)
C10	0.061 (2)	0.072 (2)	0.110 (3)	0.0042 (18)	0.006 (2)	−0.047 (2)
O5	0.0514 (12)	0.0721 (15)	0.0788 (15)	−0.0088 (11)	−0.0032 (11)	−0.0153 (13)
O6	0.104 (4)	0.137 (5)	0.118 (4)	−0.001 (3)	0.001 (3)	0.042 (4)
O8	0.188 (6)	0.175 (6)	0.115 (4)	0.028 (5)	−0.007 (5)	−0.022 (5)
O9	0.134 (11)	0.123 (11)	0.095 (9)	0.001 (8)	0.015 (7)	−0.004 (8)
O10	0.158 (12)	0.139 (12)	0.147 (12)	−0.026 (9)	0.000	0.000

Geometric parameters (Å, º)

O1—C1	1.413 (3)	C5—C6	1.383 (3)
O1—H1	0.8200	C5—H5	0.9300
O2—C3	1.419 (3)	C6—C7	1.388 (3)
O2—C2	1.433 (3)	C7—C8	1.374 (4)
O3—C6	1.369 (3)	C8—C9	1.388 (4)
O3—C10	1.403 (4)	C8—H8	0.9300
O4—C7	1.370 (3)	C9—H9	0.9300
O4—H4	0.8200	C10—H10A	0.9600
C1—C3^i	1.527 (3)	C10—H10B	0.9600
C1—C2	1.535 (3)	C10—H10C	0.9600
C1—C1^i	1.546 (4)	O5—H5A	0.8500
C2—C4	1.507 (3)	O5—H5B	0.8501
C2—H2	0.9800	O5—H5C	0.8501
C3—C1^i	1.526 (3)	O6—O7	1.556 (17)
C3—H3A	0.9700	O8—O10	1.410 (14)
C3—H3B	0.9700	O9—O9^ii	1.39 (4)
C4—C9	1.377 (3)	O10—O8^iii	1.410 (13)
C4—C5	1.395 (3)
C1—O1—H1	109.5	C6—C5—C4	120.3 (2)
C3—O2—C2	109.75 (18)	C6—C5—H5	119.9
C6—O3—C10	118.5 (2)	C4—C5—H5	119.9
C7—O4—H4	109.5	O3—C6—C5	124.8 (2)
O1—C1—C3^i	110.4 (2)	O3—C6—C7	115.3 (2)
O1—C1—C2	112.87 (18)	C5—C6—C7	119.9 (2)
C3^i—C1—C2	114.5 (2)	O4—C7—C8	124.0 (2)
O1—C1—C1^i	113.58 (12)	O4—C7—C6	116.1 (2)
C3^i—C1—C1^i	104.1 (2)	C8—C7—C6	119.9 (2)
C2—C1—C1^i	100.75 (17)	C7—C8—C9	120.2 (2)
O2—C2—C4	110.2 (2)	C7—C8—H8	119.9
O2—C2—C1	104.65 (19)	C9—C8—H8	119.9
C4—C2—C1	115.7 (2)	C4—C9—C8	120.6 (2)
O2—C2—H2	108.7	C4—C9—H9	119.7
C4—C2—H2	108.7	C8—C9—H9	119.7
C1—C2—H2	108.7	O3—C10—H10A	109.5
O2—C3—C1^i	107.21 (19)	O3—C10—H10B	109.5
O2—C3—H3A	110.3	H10A—C10—H10B	109.5
C1^i—C3—H3A	110.3	O3—C10—H10C	109.5
O2—C3—H3B	110.3	H10A—C10—H10C	109.5
C1^i—C3—H3B	110.3	H10B—C10—H10C	109.5
H3A—C3—H3B	108.5	H5A—O5—H5B	110.8
C9—C4—C5	119.2 (2)	H5A—O5—H5C	110.9
C9—C4—C2	122.7 (2)	H5B—O5—H5C	110.2
C5—C4—C2	118.1 (2)	O8^iii—O10—O8	137 (2)
C3—O2—C2—C4	−155.8 (2)	C2—C4—C5—C6	−178.8 (2)
C3—O2—C2—C1	−30.8 (3)	C10—O3—C6—C5	−6.3 (4)
O1—C1—C2—O2	−84.9 (2)	C10—O3—C6—C7	175.7 (3)
C3^i—C1—C2—O2	147.7 (2)	C4—C5—C6—O3	180.0 (2)
C1^i—C1—C2—O2	36.6 (2)	C4—C5—C6—C7	−2.1 (4)
O1—C1—C2—C4	36.6 (3)	O3—C6—C7—O4	0.2 (3)
C3^i—C1—C2—C4	−90.8 (3)	C5—C6—C7—O4	−178.0 (2)
C1^i—C1—C2—C4	158.1 (2)	O3—C6—C7—C8	−179.0 (2)
C2—O2—C3—C1^i	11.2 (3)	C5—C6—C7—C8	2.9 (4)
O2—C2—C4—C9	27.3 (3)	O4—C7—C8—C9	179.1 (3)
C1—C2—C4—C9	−91.1 (3)	C6—C7—C8—C9	−1.7 (4)
O2—C2—C4—C5	−153.7 (2)	C5—C4—C9—C8	1.0 (4)
C1—C2—C4—C5	87.8 (3)	C2—C4—C9—C8	179.9 (3)
C9—C4—C5—C6	0.2 (4)	C7—C8—C9—C4	−0.2 (4)

Symmetry codes: (i) −x+1, −y, z; (ii) −x+1, −y+1, z; (iii) −x+1, −y+2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5C···O10^iv	0.85	2.23	3.041 (19)	160
O5—H5C···O8^ii	0.85	1.86	2.663 (7)	158
O5—H5B···O5^ii	0.85	2.11	2.925 (5)	164
O5—H5A···O3^v	0.85	2.25	2.989 (3)	145
O5—H5A···O4^v	0.85	2.21	2.929 (3)	142
O4—H4···O1^v	0.82	1.85	2.656 (2)	166
O1—H1···O5	0.82	1.93	2.732 (3)	167

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