The title compound, C
20H
17FO
7·C
3H
6O, 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.
Supporting information
CCDC reference: 271891
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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).
Crystal data top
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) Å3 | Platelet, colorless |
Z = 4 | 0.41 × 0.28 × 0.08 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2086 reflections with F2 > 2.0σ(F2) |
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 top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[0.0025Fo2 + 1σ(Fo2)]/(4Fo2) |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.92 | 1.96 | 2.835 (2) | 158 |
O7—H701···O6ii | 0.94 | 1.98 | 2.857 (3) | 154 |
C20—H20···O3iii | 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. |