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The title compound, C
22H
23FO
6, is an unexpected product of the fluorination of podophyllol. The absolute configuration was determined from the known configuration of the synthetic precursor. Non-classical C—H
O hydrogen bonds link the molecules in the crystal structure into sheets parallel to (001).
Supporting information
CCDC reference: 271894
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.143
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.731
Test value = 0.675
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.21
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.73 e/A 3
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 - C5 .. 6.50 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
PLAT432_ALERT_2_C Short Inter X...Y Contact F1 .. C22 .. 2.94 Ang.
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 2519
Count of symmetry unique reflns 2561
Completeness (_total/calc) 98.36%
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
10 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 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: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
Crystal data top
C22H23FO6 | F(000) = 848 |
Mr = 402.4 | Dx = 1.39 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 22120 reflections |
a = 7.2253 (1) Å | θ = 1.2–27.5° |
b = 8.1217 (1) Å | µ = 0.11 mm−1 |
c = 32.7768 (4) Å | T = 293 K |
V = 1923.40 (4) Å3 | Prism, colourless |
Z = 4 | 0.38 × 0.22 × 0.21 mm |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 2296 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.956, Tmax = 0.978 | k = −10→10 |
14274 measured reflections | l = −42→40 |
2519 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.05 | w = 1/[σ2(Fo2) + (0.0946P)2 + 0.3221P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.143 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.73 e Å−3 |
2519 reflections | Δρmin = −0.33 e Å−3 |
265 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.3768 (4) | 0.1661 (4) | 0.43426 (8) | 0.0943 (9) | |
O1 | 0.1314 (3) | 0.5638 (3) | 0.34866 (7) | 0.0489 (5) | |
O2 | 0.5840 (4) | 0.3373 (4) | 0.21736 (7) | 0.0692 (8) | |
O3 | 0.8477 (3) | 0.4349 (4) | 0.24895 (6) | 0.0632 (7) | |
O4 | 0.8202 (4) | 1.0503 (3) | 0.36740 (6) | 0.0521 (6) | |
O5 | 0.9504 (3) | 1.0411 (3) | 0.44375 (7) | 0.0481 (5) | |
O6 | 0.8829 (3) | 0.7823 (3) | 0.49289 (5) | 0.0446 (5) | |
C1 | 0.5417 (3) | 0.4926 (3) | 0.38474 (7) | 0.0298 (5) | |
H1 | 0.602 | 0.3967 | 0.3971 | 0.036* | |
C2 | 0.3417 (4) | 0.4952 (4) | 0.40196 (8) | 0.0393 (6) | |
H2 | 0.3426 | 0.5016 | 0.4318 | 0.047* | |
C3 | 0.2236 (4) | 0.6323 (4) | 0.38366 (10) | 0.0478 (7) | |
H3A | 0.1337 | 0.6709 | 0.4034 | 0.057* | |
H3B | 0.3009 | 0.7243 | 0.3756 | 0.057* | |
C4 | 0.2338 (4) | 0.3426 (4) | 0.38727 (9) | 0.0440 (7) | |
H4 | 0.1139 | 0.3406 | 0.4012 | 0.053* | |
C5 | 0.3253 (5) | 0.1791 (4) | 0.39322 (10) | 0.0549 (8) | |
H5A | 0.2404 | 0.0911 | 0.3861 | 0.066* | |
H5B | 0.4336 | 0.1705 | 0.3759 | 0.066* | |
C6 | 0.2027 (4) | 0.3987 (4) | 0.34330 (9) | 0.0418 (6) | |
H6 | 0.1115 | 0.3285 | 0.3296 | 0.05* | |
C7 | 0.3806 (4) | 0.4045 (3) | 0.31951 (8) | 0.0364 (6) | |
C8 | 0.3818 (4) | 0.3607 (4) | 0.27804 (9) | 0.0434 (7) | |
H8 | 0.2752 | 0.3239 | 0.265 | 0.052* | |
C9 | 0.5451 (4) | 0.3743 (4) | 0.25763 (8) | 0.0453 (7) | |
C10 | 0.7756 (6) | 0.3642 (8) | 0.21299 (11) | 0.0860 (16) | |
H10A | 0.798 | 0.4371 | 0.1901 | 0.103* | |
H10B | 0.8375 | 0.2605 | 0.2076 | 0.103* | |
C11 | 0.7041 (4) | 0.4324 (4) | 0.27640 (8) | 0.0392 (6) | |
C12 | 0.7075 (3) | 0.4749 (3) | 0.31684 (8) | 0.0342 (5) | |
H12 | 0.8156 | 0.5117 | 0.3292 | 0.041* | |
C13 | 0.5419 (3) | 0.4609 (3) | 0.33877 (7) | 0.0303 (5) | |
C14 | 0.6516 (3) | 0.6412 (3) | 0.39879 (7) | 0.0296 (5) | |
C15 | 0.6782 (4) | 0.7793 (3) | 0.37453 (7) | 0.0340 (5) | |
H15 | 0.6293 | 0.7832 | 0.3483 | 0.041* | |
C16 | 0.7790 (4) | 0.9123 (3) | 0.38980 (8) | 0.0355 (6) | |
C17 | 0.8456 (4) | 0.9117 (3) | 0.42968 (8) | 0.0345 (5) | |
C18 | 0.8149 (3) | 0.7732 (3) | 0.45409 (7) | 0.0325 (5) | |
C19 | 0.7212 (3) | 0.6381 (3) | 0.43852 (7) | 0.0320 (5) | |
H19 | 0.7046 | 0.545 | 0.4546 | 0.038* | |
C20 | 0.7856 (5) | 1.0437 (4) | 0.32491 (9) | 0.0544 (8) | |
H20A | 0.6553 | 1.0554 | 0.32 | 0.082* | |
H20B | 0.8271 | 0.9398 | 0.3143 | 0.082* | |
H20C | 0.851 | 1.1313 | 0.3115 | 0.082* | |
C21 | 0.8560 (7) | 1.1537 (5) | 0.46829 (13) | 0.0727 (11) | |
H21A | 0.7951 | 1.0962 | 0.4901 | 0.109* | |
H21B | 0.7656 | 1.211 | 0.4522 | 0.109* | |
H21C | 0.9423 | 1.2314 | 0.4795 | 0.109* | |
C22 | 0.8616 (4) | 0.6388 (4) | 0.51769 (8) | 0.0458 (7) | |
H22A | 0.9263 | 0.5483 | 0.5054 | 0.069* | |
H22B | 0.7326 | 0.6121 | 0.52 | 0.069* | |
H22C | 0.9116 | 0.6596 | 0.5443 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.109 (2) | 0.0891 (19) | 0.0852 (16) | −0.0146 (18) | −0.0181 (16) | 0.0364 (15) |
O1 | 0.0333 (9) | 0.0561 (14) | 0.0572 (12) | 0.0032 (10) | −0.0040 (9) | −0.0004 (10) |
O2 | 0.0659 (15) | 0.106 (2) | 0.0359 (10) | −0.0031 (17) | −0.0036 (10) | −0.0218 (13) |
O3 | 0.0515 (12) | 0.096 (2) | 0.0420 (10) | −0.0055 (15) | 0.0118 (10) | −0.0196 (12) |
O4 | 0.0759 (14) | 0.0341 (11) | 0.0464 (10) | −0.0171 (11) | −0.0099 (11) | 0.0096 (8) |
O5 | 0.0496 (11) | 0.0394 (12) | 0.0553 (11) | −0.0141 (10) | −0.0065 (10) | −0.0042 (9) |
O6 | 0.0565 (12) | 0.0421 (12) | 0.0353 (9) | −0.0118 (10) | −0.0152 (9) | 0.0011 (8) |
C1 | 0.0324 (11) | 0.0288 (12) | 0.0281 (10) | −0.0018 (10) | −0.0042 (9) | −0.0007 (9) |
C2 | 0.0366 (13) | 0.0482 (17) | 0.0331 (11) | −0.0074 (12) | 0.0048 (10) | −0.0022 (11) |
C3 | 0.0366 (13) | 0.0504 (18) | 0.0565 (16) | 0.0025 (13) | 0.0018 (13) | −0.0081 (15) |
C4 | 0.0356 (13) | 0.0500 (17) | 0.0463 (14) | −0.0141 (13) | 0.0036 (12) | 0.0034 (13) |
C5 | 0.0617 (19) | 0.0455 (18) | 0.0575 (17) | −0.0182 (16) | −0.0020 (16) | 0.0094 (14) |
C6 | 0.0306 (12) | 0.0481 (17) | 0.0466 (14) | −0.0077 (12) | −0.0045 (11) | −0.0023 (12) |
C7 | 0.0341 (12) | 0.0360 (14) | 0.0391 (12) | −0.0038 (11) | −0.0051 (11) | −0.0002 (10) |
C8 | 0.0395 (13) | 0.0507 (17) | 0.0401 (13) | −0.0072 (13) | −0.0125 (12) | −0.0047 (13) |
C9 | 0.0517 (16) | 0.0509 (18) | 0.0333 (12) | 0.0004 (15) | −0.0070 (11) | −0.0076 (12) |
C10 | 0.076 (3) | 0.135 (5) | 0.0469 (18) | −0.018 (3) | 0.0143 (18) | −0.035 (2) |
C11 | 0.0357 (12) | 0.0445 (16) | 0.0375 (12) | 0.0010 (12) | 0.0006 (11) | −0.0041 (11) |
C12 | 0.0305 (11) | 0.0364 (13) | 0.0357 (11) | −0.0010 (11) | −0.0054 (10) | −0.0039 (10) |
C13 | 0.0286 (10) | 0.0308 (13) | 0.0315 (10) | −0.0005 (9) | −0.0043 (9) | −0.0020 (10) |
C14 | 0.0288 (10) | 0.0289 (12) | 0.0312 (10) | −0.0009 (10) | −0.0014 (9) | −0.0025 (9) |
C15 | 0.0372 (12) | 0.0347 (13) | 0.0299 (10) | −0.0014 (11) | −0.0034 (10) | 0.0005 (10) |
C16 | 0.0387 (13) | 0.0300 (13) | 0.0377 (12) | −0.0029 (11) | −0.0003 (11) | 0.0044 (10) |
C17 | 0.0314 (11) | 0.0309 (13) | 0.0412 (12) | −0.0043 (10) | −0.0016 (10) | −0.0037 (10) |
C18 | 0.0309 (11) | 0.0357 (13) | 0.0308 (10) | −0.0022 (10) | −0.0009 (9) | −0.0019 (9) |
C19 | 0.0367 (12) | 0.0289 (12) | 0.0305 (10) | −0.0010 (10) | −0.0019 (10) | 0.0013 (9) |
C20 | 0.070 (2) | 0.0473 (17) | 0.0456 (14) | −0.0078 (17) | −0.0004 (15) | 0.0140 (14) |
C21 | 0.094 (3) | 0.049 (2) | 0.075 (2) | −0.011 (2) | −0.004 (2) | −0.0234 (18) |
C22 | 0.0528 (15) | 0.0504 (17) | 0.0342 (12) | −0.0112 (15) | −0.0129 (12) | 0.0072 (12) |
Geometric parameters (Å, º) top
F1—C5 | 1.400 (4) | C6—H6 | 0.98 |
O1—C3 | 1.438 (4) | C7—C13 | 1.403 (3) |
O1—C6 | 1.447 (4) | C7—C8 | 1.405 (4) |
O2—C9 | 1.383 (3) | C8—C9 | 1.360 (4) |
O2—C10 | 1.409 (5) | C8—H8 | 0.93 |
O3—C11 | 1.374 (3) | C9—C11 | 1.386 (4) |
O3—C10 | 1.411 (4) | C10—H10A | 0.97 |
O4—C16 | 1.373 (3) | C10—H10B | 0.97 |
O4—C20 | 1.416 (3) | C11—C12 | 1.370 (3) |
O5—C17 | 1.375 (3) | C12—C13 | 1.401 (3) |
O5—C21 | 1.396 (5) | C12—H12 | 0.93 |
O6—C18 | 1.365 (3) | C14—C15 | 1.388 (4) |
O6—C22 | 1.430 (4) | C14—C19 | 1.396 (3) |
C1—C14 | 1.516 (3) | C15—C16 | 1.396 (4) |
C1—C13 | 1.529 (3) | C15—H15 | 0.93 |
C1—C2 | 1.552 (3) | C16—C17 | 1.393 (4) |
C1—H1 | 0.98 | C17—C18 | 1.398 (4) |
C2—C3 | 1.526 (4) | C18—C19 | 1.386 (4) |
C2—C4 | 1.541 (4) | C19—H19 | 0.93 |
C2—H2 | 0.98 | C20—H20A | 0.96 |
C3—H3A | 0.97 | C20—H20B | 0.96 |
C3—H3B | 0.97 | C20—H20C | 0.96 |
C4—C5 | 1.496 (5) | C21—H21A | 0.96 |
C4—C6 | 1.528 (4) | C21—H21B | 0.96 |
C4—H4 | 0.98 | C21—H21C | 0.96 |
C5—H5A | 0.97 | C22—H22A | 0.96 |
C5—H5B | 0.97 | C22—H22B | 0.96 |
C6—C7 | 1.504 (4) | C22—H22C | 0.96 |
| | | |
C3—O1—C6 | 106.9 (2) | O2—C10—O3 | 109.9 (3) |
C9—O2—C10 | 105.3 (3) | O2—C10—H10A | 109.7 |
C11—O3—C10 | 105.2 (3) | O3—C10—H10A | 109.7 |
C16—O4—C20 | 117.2 (2) | O2—C10—H10B | 109.7 |
C17—O5—C21 | 115.1 (3) | O3—C10—H10B | 109.7 |
C18—O6—C22 | 116.5 (2) | H10A—C10—H10B | 108.2 |
C14—C1—C13 | 115.7 (2) | C12—C11—O3 | 128.0 (2) |
C14—C1—C2 | 111.5 (2) | C12—C11—C9 | 122.0 (2) |
C13—C1—C2 | 111.20 (18) | O3—C11—C9 | 109.9 (2) |
C14—C1—H1 | 105.9 | C11—C12—C13 | 117.4 (2) |
C13—C1—H1 | 105.9 | C11—C12—H12 | 121.3 |
C2—C1—H1 | 105.9 | C13—C12—H12 | 121.3 |
C3—C2—C4 | 100.4 (2) | C12—C13—C7 | 120.4 (2) |
C3—C2—C1 | 112.8 (2) | C12—C13—C1 | 119.5 (2) |
C4—C2—C1 | 110.3 (2) | C7—C13—C1 | 119.9 (2) |
C3—C2—H2 | 111 | C15—C14—C19 | 119.9 (2) |
C4—C2—H2 | 111 | C15—C14—C1 | 122.8 (2) |
C1—C2—H2 | 111 | C19—C14—C1 | 117.2 (2) |
O1—C3—C2 | 106.9 (2) | C14—C15—C16 | 119.5 (2) |
O1—C3—H3A | 110.3 | C14—C15—H15 | 120.3 |
C2—C3—H3A | 110.3 | C16—C15—H15 | 120.3 |
O1—C3—H3B | 110.3 | O4—C16—C17 | 115.5 (2) |
C2—C3—H3B | 110.3 | O4—C16—C15 | 123.6 (2) |
H3A—C3—H3B | 108.6 | C17—C16—C15 | 121.0 (2) |
C5—C4—C6 | 116.9 (3) | O5—C17—C16 | 120.2 (2) |
C5—C4—C2 | 116.7 (3) | O5—C17—C18 | 120.7 (2) |
C6—C4—C2 | 97.4 (2) | C16—C17—C18 | 119.0 (2) |
C5—C4—H4 | 108.4 | O6—C18—C19 | 124.2 (2) |
C6—C4—H4 | 108.4 | O6—C18—C17 | 115.6 (2) |
C2—C4—H4 | 108.4 | C19—C18—C17 | 120.2 (2) |
F1—C5—C4 | 108.0 (3) | C18—C19—C14 | 120.3 (2) |
F1—C5—H5A | 110.1 | C18—C19—H19 | 119.8 |
C4—C5—H5A | 110.1 | C14—C19—H19 | 119.8 |
F1—C5—H5B | 110.1 | O4—C20—H20A | 109.5 |
C4—C5—H5B | 110.1 | O4—C20—H20B | 109.5 |
H5A—C5—H5B | 108.4 | H20A—C20—H20B | 109.5 |
O1—C6—C7 | 109.8 (2) | O4—C20—H20C | 109.5 |
O1—C6—C4 | 102.4 (2) | H20A—C20—H20C | 109.5 |
C7—C6—C4 | 111.9 (2) | H20B—C20—H20C | 109.5 |
O1—C6—H6 | 110.8 | O5—C21—H21A | 109.5 |
C7—C6—H6 | 110.8 | O5—C21—H21B | 109.5 |
C4—C6—H6 | 110.8 | H21A—C21—H21B | 109.5 |
C13—C7—C8 | 120.9 (2) | O5—C21—H21C | 109.5 |
C13—C7—C6 | 119.1 (2) | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 120.0 (2) | H21B—C21—H21C | 109.5 |
C9—C8—C7 | 117.4 (2) | O6—C22—H22A | 109.5 |
C9—C8—H8 | 121.3 | O6—C22—H22B | 109.5 |
C7—C8—H8 | 121.3 | H22A—C22—H22B | 109.5 |
C8—C9—O2 | 128.9 (3) | O6—C22—H22C | 109.5 |
C8—C9—C11 | 121.9 (2) | H22A—C22—H22C | 109.5 |
O2—C9—C11 | 109.2 (3) | H22B—C22—H22C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O1i | 0.97 | 2.45 | 3.238 (6) | 138 |
C12—H12···O1ii | 0.93 | 2.41 | 3.315 (3) | 166 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z. |
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