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The title compound, C22H23FO6, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010366/hg6164sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010366/hg61643sup2.hkl
Contains datablock 3

CCDC reference: 271894

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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).

(3) top
Crystal data top
C22H23FO6F(000) = 848
Mr = 402.4Dx = 1.39 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 22120 reflections
a = 7.2253 (1) Åθ = 1.2–27.5°
b = 8.1217 (1) ŵ = 0.11 mm1
c = 32.7768 (4) ÅT = 293 K
V = 1923.40 (4) Å3Prism, colourless
Z = 40.38 × 0.22 × 0.21 mm
Data collection top
Rigaku RAXIS-RAPID
diffractometer
2296 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.025
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.956, Tmax = 0.978k = 1010
14274 measured reflectionsl = 4240
2519 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.73 e Å3
2519 reflectionsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
F10.3768 (4)0.1661 (4)0.43426 (8)0.0943 (9)
O10.1314 (3)0.5638 (3)0.34866 (7)0.0489 (5)
O20.5840 (4)0.3373 (4)0.21736 (7)0.0692 (8)
O30.8477 (3)0.4349 (4)0.24895 (6)0.0632 (7)
O40.8202 (4)1.0503 (3)0.36740 (6)0.0521 (6)
O50.9504 (3)1.0411 (3)0.44375 (7)0.0481 (5)
O60.8829 (3)0.7823 (3)0.49289 (5)0.0446 (5)
C10.5417 (3)0.4926 (3)0.38474 (7)0.0298 (5)
H10.6020.39670.39710.036*
C20.3417 (4)0.4952 (4)0.40196 (8)0.0393 (6)
H20.34260.50160.43180.047*
C30.2236 (4)0.6323 (4)0.38366 (10)0.0478 (7)
H3A0.13370.67090.40340.057*
H3B0.30090.72430.37560.057*
C40.2338 (4)0.3426 (4)0.38727 (9)0.0440 (7)
H40.11390.34060.40120.053*
C50.3253 (5)0.1791 (4)0.39322 (10)0.0549 (8)
H5A0.24040.09110.38610.066*
H5B0.43360.17050.37590.066*
C60.2027 (4)0.3987 (4)0.34330 (9)0.0418 (6)
H60.11150.32850.32960.05*
C70.3806 (4)0.4045 (3)0.31951 (8)0.0364 (6)
C80.3818 (4)0.3607 (4)0.27804 (9)0.0434 (7)
H80.27520.32390.2650.052*
C90.5451 (4)0.3743 (4)0.25763 (8)0.0453 (7)
C100.7756 (6)0.3642 (8)0.21299 (11)0.0860 (16)
H10A0.7980.43710.19010.103*
H10B0.83750.26050.20760.103*
C110.7041 (4)0.4324 (4)0.27640 (8)0.0392 (6)
C120.7075 (3)0.4749 (3)0.31684 (8)0.0342 (5)
H120.81560.51170.32920.041*
C130.5419 (3)0.4609 (3)0.33877 (7)0.0303 (5)
C140.6516 (3)0.6412 (3)0.39879 (7)0.0296 (5)
C150.6782 (4)0.7793 (3)0.37453 (7)0.0340 (5)
H150.62930.78320.34830.041*
C160.7790 (4)0.9123 (3)0.38980 (8)0.0355 (6)
C170.8456 (4)0.9117 (3)0.42968 (8)0.0345 (5)
C180.8149 (3)0.7732 (3)0.45409 (7)0.0325 (5)
C190.7212 (3)0.6381 (3)0.43852 (7)0.0320 (5)
H190.70460.5450.45460.038*
C200.7856 (5)1.0437 (4)0.32491 (9)0.0544 (8)
H20A0.65531.05540.320.082*
H20B0.82710.93980.31430.082*
H20C0.8511.13130.31150.082*
C210.8560 (7)1.1537 (5)0.46829 (13)0.0727 (11)
H21A0.79511.09620.49010.109*
H21B0.76561.2110.45220.109*
H21C0.94231.23140.47950.109*
C220.8616 (4)0.6388 (4)0.51769 (8)0.0458 (7)
H22A0.92630.54830.50540.069*
H22B0.73260.61210.520.069*
H22C0.91160.65960.54430.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.109 (2)0.0891 (19)0.0852 (16)0.0146 (18)0.0181 (16)0.0364 (15)
O10.0333 (9)0.0561 (14)0.0572 (12)0.0032 (10)0.0040 (9)0.0004 (10)
O20.0659 (15)0.106 (2)0.0359 (10)0.0031 (17)0.0036 (10)0.0218 (13)
O30.0515 (12)0.096 (2)0.0420 (10)0.0055 (15)0.0118 (10)0.0196 (12)
O40.0759 (14)0.0341 (11)0.0464 (10)0.0171 (11)0.0099 (11)0.0096 (8)
O50.0496 (11)0.0394 (12)0.0553 (11)0.0141 (10)0.0065 (10)0.0042 (9)
O60.0565 (12)0.0421 (12)0.0353 (9)0.0118 (10)0.0152 (9)0.0011 (8)
C10.0324 (11)0.0288 (12)0.0281 (10)0.0018 (10)0.0042 (9)0.0007 (9)
C20.0366 (13)0.0482 (17)0.0331 (11)0.0074 (12)0.0048 (10)0.0022 (11)
C30.0366 (13)0.0504 (18)0.0565 (16)0.0025 (13)0.0018 (13)0.0081 (15)
C40.0356 (13)0.0500 (17)0.0463 (14)0.0141 (13)0.0036 (12)0.0034 (13)
C50.0617 (19)0.0455 (18)0.0575 (17)0.0182 (16)0.0020 (16)0.0094 (14)
C60.0306 (12)0.0481 (17)0.0466 (14)0.0077 (12)0.0045 (11)0.0023 (12)
C70.0341 (12)0.0360 (14)0.0391 (12)0.0038 (11)0.0051 (11)0.0002 (10)
C80.0395 (13)0.0507 (17)0.0401 (13)0.0072 (13)0.0125 (12)0.0047 (13)
C90.0517 (16)0.0509 (18)0.0333 (12)0.0004 (15)0.0070 (11)0.0076 (12)
C100.076 (3)0.135 (5)0.0469 (18)0.018 (3)0.0143 (18)0.035 (2)
C110.0357 (12)0.0445 (16)0.0375 (12)0.0010 (12)0.0006 (11)0.0041 (11)
C120.0305 (11)0.0364 (13)0.0357 (11)0.0010 (11)0.0054 (10)0.0039 (10)
C130.0286 (10)0.0308 (13)0.0315 (10)0.0005 (9)0.0043 (9)0.0020 (10)
C140.0288 (10)0.0289 (12)0.0312 (10)0.0009 (10)0.0014 (9)0.0025 (9)
C150.0372 (12)0.0347 (13)0.0299 (10)0.0014 (11)0.0034 (10)0.0005 (10)
C160.0387 (13)0.0300 (13)0.0377 (12)0.0029 (11)0.0003 (11)0.0044 (10)
C170.0314 (11)0.0309 (13)0.0412 (12)0.0043 (10)0.0016 (10)0.0037 (10)
C180.0309 (11)0.0357 (13)0.0308 (10)0.0022 (10)0.0009 (9)0.0019 (9)
C190.0367 (12)0.0289 (12)0.0305 (10)0.0010 (10)0.0019 (10)0.0013 (9)
C200.070 (2)0.0473 (17)0.0456 (14)0.0078 (17)0.0004 (15)0.0140 (14)
C210.094 (3)0.049 (2)0.075 (2)0.011 (2)0.004 (2)0.0234 (18)
C220.0528 (15)0.0504 (17)0.0342 (12)0.0112 (15)0.0129 (12)0.0072 (12)
Geometric parameters (Å, º) top
F1—C51.400 (4)C6—H60.98
O1—C31.438 (4)C7—C131.403 (3)
O1—C61.447 (4)C7—C81.405 (4)
O2—C91.383 (3)C8—C91.360 (4)
O2—C101.409 (5)C8—H80.93
O3—C111.374 (3)C9—C111.386 (4)
O3—C101.411 (4)C10—H10A0.97
O4—C161.373 (3)C10—H10B0.97
O4—C201.416 (3)C11—C121.370 (3)
O5—C171.375 (3)C12—C131.401 (3)
O5—C211.396 (5)C12—H120.93
O6—C181.365 (3)C14—C151.388 (4)
O6—C221.430 (4)C14—C191.396 (3)
C1—C141.516 (3)C15—C161.396 (4)
C1—C131.529 (3)C15—H150.93
C1—C21.552 (3)C16—C171.393 (4)
C1—H10.98C17—C181.398 (4)
C2—C31.526 (4)C18—C191.386 (4)
C2—C41.541 (4)C19—H190.93
C2—H20.98C20—H20A0.96
C3—H3A0.97C20—H20B0.96
C3—H3B0.97C20—H20C0.96
C4—C51.496 (5)C21—H21A0.96
C4—C61.528 (4)C21—H21B0.96
C4—H40.98C21—H21C0.96
C5—H5A0.97C22—H22A0.96
C5—H5B0.97C22—H22B0.96
C6—C71.504 (4)C22—H22C0.96
C3—O1—C6106.9 (2)O2—C10—O3109.9 (3)
C9—O2—C10105.3 (3)O2—C10—H10A109.7
C11—O3—C10105.2 (3)O3—C10—H10A109.7
C16—O4—C20117.2 (2)O2—C10—H10B109.7
C17—O5—C21115.1 (3)O3—C10—H10B109.7
C18—O6—C22116.5 (2)H10A—C10—H10B108.2
C14—C1—C13115.7 (2)C12—C11—O3128.0 (2)
C14—C1—C2111.5 (2)C12—C11—C9122.0 (2)
C13—C1—C2111.20 (18)O3—C11—C9109.9 (2)
C14—C1—H1105.9C11—C12—C13117.4 (2)
C13—C1—H1105.9C11—C12—H12121.3
C2—C1—H1105.9C13—C12—H12121.3
C3—C2—C4100.4 (2)C12—C13—C7120.4 (2)
C3—C2—C1112.8 (2)C12—C13—C1119.5 (2)
C4—C2—C1110.3 (2)C7—C13—C1119.9 (2)
C3—C2—H2111C15—C14—C19119.9 (2)
C4—C2—H2111C15—C14—C1122.8 (2)
C1—C2—H2111C19—C14—C1117.2 (2)
O1—C3—C2106.9 (2)C14—C15—C16119.5 (2)
O1—C3—H3A110.3C14—C15—H15120.3
C2—C3—H3A110.3C16—C15—H15120.3
O1—C3—H3B110.3O4—C16—C17115.5 (2)
C2—C3—H3B110.3O4—C16—C15123.6 (2)
H3A—C3—H3B108.6C17—C16—C15121.0 (2)
C5—C4—C6116.9 (3)O5—C17—C16120.2 (2)
C5—C4—C2116.7 (3)O5—C17—C18120.7 (2)
C6—C4—C297.4 (2)C16—C17—C18119.0 (2)
C5—C4—H4108.4O6—C18—C19124.2 (2)
C6—C4—H4108.4O6—C18—C17115.6 (2)
C2—C4—H4108.4C19—C18—C17120.2 (2)
F1—C5—C4108.0 (3)C18—C19—C14120.3 (2)
F1—C5—H5A110.1C18—C19—H19119.8
C4—C5—H5A110.1C14—C19—H19119.8
F1—C5—H5B110.1O4—C20—H20A109.5
C4—C5—H5B110.1O4—C20—H20B109.5
H5A—C5—H5B108.4H20A—C20—H20B109.5
O1—C6—C7109.8 (2)O4—C20—H20C109.5
O1—C6—C4102.4 (2)H20A—C20—H20C109.5
C7—C6—C4111.9 (2)H20B—C20—H20C109.5
O1—C6—H6110.8O5—C21—H21A109.5
C7—C6—H6110.8O5—C21—H21B109.5
C4—C6—H6110.8H21A—C21—H21B109.5
C13—C7—C8120.9 (2)O5—C21—H21C109.5
C13—C7—C6119.1 (2)H21A—C21—H21C109.5
C8—C7—C6120.0 (2)H21B—C21—H21C109.5
C9—C8—C7117.4 (2)O6—C22—H22A109.5
C9—C8—H8121.3O6—C22—H22B109.5
C7—C8—H8121.3H22A—C22—H22B109.5
C8—C9—O2128.9 (3)O6—C22—H22C109.5
C8—C9—C11121.9 (2)H22A—C22—H22C109.5
O2—C9—C11109.2 (3)H22B—C22—H22C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O1i0.972.453.238 (6)138
C12—H12···O1ii0.932.413.315 (3)166
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y, z.
 

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