(5R,5aR,8aR,9S)-5-(3,4-di­hydroxy-5-methoxy­phenyl)-9-fluoro-5,8,8a,9-tetra­hydrofuro­[3′,4′:6,7]­naphtho­[2,3-d]-1,3-dioxol-6(5aH)-one acetone solvate

The title compound, C₂₀H₁₇FO₇·C₃H₆O, is a potential antitumour agent. Its absolute configuration was assigned based on that of the synthetic precursor. Intermolecular O—H...O hydrogen bonds link the mol­ecules in the crystal structure into layers parallel to (010). These layers are stabilized by weak interlayer C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.132
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.96
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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           27.48
           From the CIF: _reflns_number_total               2486
           Count of symmetry unique reflns         2555
           Completeness (_total/calc)             97.30%
           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

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

   1 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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku,1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 1998).

(I)

Crystal data

C20H17FO7·C3H6O	F(000) = 936.00
Mr = 446.43	Dx = 1.427 Mg m^−3
Monoclinic, C2	Melting point: 261 K
Hall symbol: C 2y	Mo Kα radiation, λ = 0.7107 Å
a = 19.1786 (9) Å	Cell parameters from 7291 reflections
b = 7.7058 (3) Å	θ = 2.9–27.5°
c = 14.0757 (7) Å	µ = 0.11 mm^−1
β = 92.373 (2)°	T = 296 K
V = 2078.4 (2) Å^3	Platelet, colorless
Z = 4	0.41 × 0.28 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2086 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.023
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Higashi, 1995)	h = −24→24
Tmin = 0.923, Tmax = 0.991	k = −10→8
9048 measured reflections	l = −18→18
2486 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[0.0025Fo^2 + 1σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.132	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.23 e Å^−3
2484 reflections	Δρmin = −0.28 e Å^−3
312 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.2998 (1)	0.1015 (3)	0.4754 (1)	0.0577 (6)
O1	0.1576 (1)	0.3530 (4)	0.1858 (1)	0.0469 (6)
O2	0.2110 (1)	0.1012 (4)	0.2132 (2)	0.0625 (8)
O3	0.4706 (1)	0.5744 (4)	0.6327 (2)	0.0647 (9)
O4	0.4178 (1)	0.8223 (4)	0.5715 (2)	0.0633 (8)
O5	0.2705 (1)	0.7632 (4)	−0.0044 (1)	0.0487 (6)
O6	0.4101 (1)	0.7420 (4)	−0.0135 (1)	0.0440 (6)
O7	0.4886 (1)	0.6073 (5)	0.1372 (2)	0.0607 (7)
O8	0.4836 (2)	0.1407 (8)	0.2990 (4)	0.125 (2)
C1	0.2795 (1)	0.5079 (4)	0.3196 (2)	0.0306 (6)
C2	0.2484 (1)	0.3267 (4)	0.3136 (2)	0.0351 (7)
C3	0.2009 (2)	0.2706 (5)	0.2304 (2)	0.0432 (8)
C4	0.2637 (2)	0.0299 (6)	0.2798 (3)	0.063 (1)
C5	0.3051 (2)	0.1880 (5)	0.3136 (2)	0.0405 (7)
C6	0.3435 (1)	0.1811 (5)	0.4098 (2)	0.0400 (8)
C7	0.3611 (1)	0.3606 (5)	0.4449 (2)	0.0355 (7)
C8	0.4100 (2)	0.3704 (5)	0.5228 (2)	0.0435 (8)
C9	0.4248 (2)	0.5314 (5)	0.5581 (2)	0.0436 (8)
C10	0.4670 (2)	0.7558 (6)	0.6417 (3)	0.057 (1)
C11	0.3942 (1)	0.6789 (5)	0.5217 (2)	0.0410 (7)
C12	0.3481 (1)	0.6738 (5)	0.4460 (2)	0.0380 (7)
C13	0.3308 (1)	0.5106 (4)	0.4068 (2)	0.0316 (6)
C14	0.3150 (1)	0.5671 (4)	0.2298 (2)	0.0296 (6)
C15	0.2744 (1)	0.6350 (4)	0.1545 (2)	0.0325 (6)
C16	0.3051 (1)	0.6942 (4)	0.0731 (2)	0.0328 (6)
C17	0.1968 (1)	0.7513 (6)	−0.0091 (3)	0.057 (1)
C18	0.3776 (1)	0.6847 (4)	0.0655 (2)	0.0341 (6)
C19	0.4183 (1)	0.6179 (5)	0.1405 (2)	0.0373 (7)
C20	0.3873 (1)	0.5592 (4)	0.2221 (2)	0.0356 (7)
C21	0.5094 (2)	0.1615 (7)	0.2224 (4)	0.081 (2)
C22	0.5783 (3)	0.247 (1)	0.2198 (4)	0.099 (2)
C23	0.4742 (4)	0.112 (1)	0.1340 (7)	0.157 (4)
H1	0.2417	0.5897	0.3314	0.036*
H2	0.2225	0.3095	0.3714	0.042*
H41	0.2427	−0.0291	0.3324	0.075*
H42	0.2937	−0.0502	0.2475	0.075*
H8	0.4324	0.2662	0.5499	0.052*
H12	0.3270	0.7805	0.4200	0.045*
H15	0.2236	0.6404	0.1590	0.039*
H171	0.1788	0.7906	−0.0700	0.068*
H172	0.1828	0.6331	0.0005	0.068*
H173	0.1788	0.8230	0.0399	0.068*
H20	0.4164	0.5121	0.2748	0.042*
H221	0.5718	0.3703	0.2139	0.120*
H223	0.6029	0.2049	0.1664	0.120*
H222	0.6041	0.2220	0.2781	0.120*
H5	0.3384	0.2189	0.2654	0.048*
H6	0.3864	0.1131	0.4049	0.048*
H102	0.4520	0.7854	0.7046	0.069*
H101	0.5126	0.8057	0.6324	0.069*
H601	0.3784	0.7622	−0.0633	0.053*
H701	0.5097	0.6658	0.0875	0.073*
H231	0.4861	−0.0049	0.1186	0.186*
H232	0.4885	0.1886	0.0844	0.186*
H233	0.4246	0.1217	0.1394	0.186*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.064 (1)	0.056 (1)	0.052 (1)	−0.008 (1)	0.0014 (9)	0.017 (1)
O1	0.039 (1)	0.063 (1)	0.038 (1)	−0.006 (1)	−0.0079 (8)	−0.000 (1)
O2	0.076 (2)	0.046 (1)	0.064 (2)	−0.010 (1)	−0.028 (1)	−0.004 (1)
O3	0.069 (2)	0.071 (2)	0.051 (1)	0.003 (1)	−0.033 (1)	−0.009 (1)
O4	0.073 (2)	0.060 (2)	0.055 (2)	−0.001 (1)	−0.026 (1)	−0.018 (1)
O5	0.034 (1)	0.076 (2)	0.036 (1)	0.002 (1)	−0.0038 (9)	0.019 (1)
O6	0.0314 (9)	0.071 (2)	0.029 (1)	−0.001 (1)	−0.0004 (7)	0.013 (1)
O7	0.0267 (9)	0.115 (2)	0.041 (1)	0.003 (1)	−0.0007 (8)	0.027 (1)
O8	0.124 (3)	0.120 (4)	0.136 (4)	0.007 (3)	0.054 (3)	0.010 (3)
C1	0.029 (1)	0.039 (1)	0.024 (1)	0.002 (1)	−0.0015 (9)	0.000 (1)
C2	0.035 (1)	0.043 (2)	0.027 (1)	−0.006 (1)	0.000 (1)	0.003 (1)
C3	0.040 (2)	0.053 (2)	0.035 (2)	−0.014 (2)	−0.002 (1)	0.001 (1)
C4	0.079 (3)	0.045 (2)	0.063 (2)	−0.009 (2)	−0.025 (2)	−0.001 (2)
C5	0.045 (1)	0.037 (1)	0.040 (2)	−0.003 (1)	−0.000 (1)	−0.001 (1)
C6	0.041 (1)	0.040 (2)	0.039 (2)	0.001 (2)	0.000 (1)	0.006 (1)
C7	0.036 (1)	0.043 (2)	0.028 (1)	0.001 (1)	0.000 (1)	0.002 (1)
C8	0.042 (1)	0.053 (2)	0.034 (1)	0.007 (2)	−0.009 (1)	0.004 (1)
C9	0.040 (1)	0.059 (2)	0.030 (1)	0.001 (2)	−0.008 (1)	−0.002 (1)
C10	0.051 (2)	0.074 (3)	0.046 (2)	−0.003 (2)	−0.012 (1)	−0.017 (2)
C11	0.041 (1)	0.049 (2)	0.033 (1)	0.000 (2)	−0.002 (1)	−0.009 (1)
C12	0.042 (1)	0.043 (2)	0.029 (1)	0.004 (1)	−0.005 (1)	−0.003 (1)
C13	0.030 (1)	0.040 (1)	0.024 (1)	0.000 (1)	0.000 (1)	−0.001 (1)
C14	0.033 (1)	0.031 (1)	0.025 (1)	−0.001 (1)	−0.0018 (9)	−0.000 (1)
C15	0.026 (1)	0.041 (2)	0.030 (1)	0.001 (1)	−0.0017 (9)	0.000 (1)
C16	0.030 (1)	0.039 (1)	0.029 (1)	0.003 (1)	−0.0042 (9)	0.003 (1)
C17	0.035 (1)	0.085 (3)	0.050 (2)	0.004 (2)	−0.012 (1)	0.027 (2)
C18	0.032 (1)	0.045 (2)	0.026 (1)	−0.001 (1)	−0.0002 (9)	0.002 (1)
C19	0.028 (1)	0.051 (2)	0.033 (1)	0.000 (1)	−0.004 (1)	0.006 (1)
C20	0.032 (1)	0.048 (2)	0.026 (1)	0.000 (1)	−0.004 (1)	0.005 (1)
C21	0.076 (3)	0.068 (3)	0.102 (4)	0.026 (3)	0.029 (3)	0.009 (3)
C22	0.080 (3)	0.102 (4)	0.118 (5)	0.021 (3)	0.031 (3)	−0.004 (4)
C23	0.129 (6)	0.140 (8)	0.197 (9)	0.031 (6)	−0.059 (7)	−0.060 (7)

Geometric parameters (Å, º)

F1—C6	1.413 (4)	C15—C16	1.387 (4)
O1—C3	1.201 (4)	C16—C18	1.401 (4)
O2—C3	1.342 (5)	C18—C19	1.386 (4)
O2—C4	1.458 (5)	C19—C20	1.389 (4)
O3—C9	1.381 (4)	C21—C22	1.480 (7)
O3—C10	1.405 (6)	C21—C23	1.44 (1)
O4—C10	1.432 (5)	O6—H601	0.9217
O4—C11	1.375 (5)	O7—H701	0.9376
O5—C16	1.362 (3)	C1—H1	0.9800
O5—C17	1.414 (3)	C2—H2	0.9800
O6—C18	1.371 (3)	C4—H41	0.9702
O7—C19	1.355 (3)	C4—H42	0.9700
O8—C21	1.216 (8)	C5—H5	0.9800
C1—C2	1.519 (4)	C6—H6	0.9800
C1—C13	1.541 (3)	C8—H8	0.9800
C1—C14	1.530 (4)	C10—H102	0.9700
C2—C3	1.517 (4)	C10—H101	0.9700
C2—C5	1.524 (4)	C12—H12	0.9800
C4—C5	1.520 (5)	C15—H15	0.9800
C5—C6	1.515 (4)	C17—H171	0.9600
C6—C7	1.503 (5)	C17—H172	0.9600
C7—C8	1.415 (4)	C17—H173	0.9600
C7—C13	1.392 (4)	C20—H20	0.9800
C8—C9	1.362 (5)	C22—H221	0.9600
C9—C11	1.369 (5)	C22—H223	0.9600
C11—C12	1.356 (4)	C22—H222	0.9600
C12—C13	1.408 (5)	C23—H231	0.9600
C14—C15	1.391 (4)	C23—H232	0.9600
C14—C20	1.398 (4)	C23—H233	0.9600
F1—C6—C5	108.7 (2)	C23—C21—C22	118.8 (6)
F1—C6—C7	108.4 (2)	F1—C6—H6	109.6290
O1—C3—C2	129.2 (3)	O2—C4—H41	111.5940
O1—C3—O2	121.4 (3)	O2—C4—H42	110.3423
O2—C3—C2	109.3 (3)	O3—C10—H102	109.4662
C4—O2—C3	110.6 (3)	O3—C10—H101	109.5342
O2—C4—C5	103.8 (3)	O4—C10—H102	109.5152
O3—C9—C8	127.8 (3)	O4—C10—H101	109.7665
C10—O3—C9	106.0 (3)	O5—C17—H172	109.8438
O3—C9—C11	109.5 (3)	O5—C17—H171	110.0341
O3—C10—O4	109.1 (3)	O5—C17—H173	108.5339
C11—O4—C10	104.9 (3)	H601—O6—C18	111.3053
O4—C11—C9	110.5 (3)	H701—O7—C19	117.1556
O4—C11—C12	127.8 (3)	C1—C2—H2	106.8310
O5—C16—C15	125.5 (2)	H1—C1—C2	107.9851
C17—O5—C16	117.7 (3)	H1—C1—C13	108.0070
O5—C16—C18	114.3 (2)	H1—C1—C14	107.8118
O6—C18—C16	122.1 (2)	H2—C2—C3	107.1086
O6—C18—C19	118.5 (2)	H2—C2—C5	106.8714
O7—C19—C18	121.8 (3)	C2—C5—H5	108.3270
O7—C19—C20	118.0 (3)	H41—C4—C5	111.3607
O8—C21—C22	118.6 (5)	H42—C4—C5	110.1790
O8—C21—C23	122.6 (6)	C4—C5—H5	108.8916
C1—C2—C5	111.5 (2)	H42—C4—H41	109.4707
C13—C1—C2	107.0 (2)	H5—C5—C6	108.7050
C1—C2—C3	121.8 (3)	C5—C6—H6	109.5825
C14—C1—C2	114.5 (2)	H6—C6—C7	109.7002
C1—C13—C7	122.6 (3)	C7—C8—H8	121.5832
C14—C1—C13	111.3 (2)	H8—C8—C9	121.5121
C1—C13—C12	117.2 (3)	H101—C10—H102	109.4620
C1—C14—C15	119.2 (2)	C11—C12—H12	120.9800
C1—C14—C20	121.9 (2)	H12—C12—C13	121.0437
C5—C2—C3	101.9 (2)	C14—C15—H15	119.5862
C2—C5—C4	101.5 (3)	C14—C20—H20	119.5357
C2—C5—C6	110.2 (3)	H15—C15—C16	119.8039
C4—C5—C6	118.7 (3)	H172—C17—H171	109.4699
C5—C6—C7	110.8 (3)	H173—C17—H171	109.4746
C6—C7—C8	115.9 (3)	H173—C17—H172	109.4669
C6—C7—C13	123.6 (2)	C19—C20—H20	119.8245
C13—C7—C8	120.5 (3)	C21—C22—H221	109.2256
C7—C8—C9	116.9 (3)	C21—C22—H223	109.6996
C7—C13—C12	120.2 (2)	C21—C22—H222	108.4995
C8—C9—C11	122.7 (3)	C21—C23—H232	109.3051
C9—C11—C12	121.7 (3)	C21—C23—H231	109.6168
C11—C12—C13	118.0 (3)	C21—C23—H233	110.0137
C14—C15—C16	120.6 (2)	H223—C22—H221	109.5354
C20—C14—C15	118.9 (2)	H222—C22—H221	109.4725
C14—C20—C19	120.6 (2)	H222—C22—H223	110.3854
C15—C16—C18	120.2 (2)	H232—C23—H231	109.4421
C16—C18—C19	119.4 (3)	H233—C23—H231	109.4709
C18—C19—C20	120.3 (2)	H233—C23—H232	108.9759

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H601···O5	0.92	2.26	2.691 (3)	108
O7—H701···O6	0.94	2.41	2.753 (3)	102
C4—H41···F1	0.97	2.47	2.865 (4)	104
O6—H601···O1^i	0.92	1.96	2.835 (2)	158
O7—H701···O6^ii	0.94	1.98	2.857 (3)	154
C20—H20···O3^iii	0.98	2.53	3.340 (3)	140

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