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The title compound, C17H12FO, a derivative of the anti­oxidant, anti­bacterial and anti-inflammatory compound curcumin, crystallizes with three independent mol­ecules (A, B and C) in the asymmetric unit. Mol­ecule C is found to have whole-mol­ecule disorder with an approximate 2:1 ratio of occupancies. The mean planes of the two 4-fluoro­phenyl groups in A, B and C form dihedral angles of 54.8 (2), 54.3 (1) and 52.4 (8)°, respectively. The angles between the mean plane of the penta-1,4-dien-3-one group and those of the two 4-fluoro­phenyl rings are 26.9 (3) and 33.7 (7)° in mol­ecule A, 25.3 (1) and 34.2 (6)° in B, and 28.0 (9) and 30.8 (1)° in C. The crystal structure is stabilized by inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026116/tk2156sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026116/tk2156Isup2.hkl
Contains datablock I

CCDC reference: 654956

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.094
  • wR factor = 0.275
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT113_ALERT_2_A ADDSYM Suggests Possible Pseudo/New Spacegroup . C2/c PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H10D PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H11D PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H13D PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H14D PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H16D PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H2CB PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H17D PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H3CB PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H5CB PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H6CB PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H7CB PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) <H8CB
Alert level B Crystal system given = monoclinic PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 100 PerFi
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.275 STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 1.300 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 1.30 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.33 Ratio PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 24.00 Perc. PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O1CB PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 40 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.60 Deg. O1CA -C9C -O1CB 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.20 Deg. C8CA -C9C -C8CB 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.20 Deg. C10D -C9C -C10C 1.555 1.555 1.555 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 1.30
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:C17 H12 F2 O1 Atom count from the _atom_site data: C17.02345 H12 F2.002933 O1.001 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies. From the CIF: _cell_formula_units_Z 12 From the CIF: _chemical_formula_sum C17 H12 F2 O TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 204.00 204.28 -0.28 H 144.00 144.00 0.00 F 24.00 24.04 -0.04 O 12.00 12.02 -0.02 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 29.06 From the CIF: _reflns_number_total 5194 Count of symmetry unique reflns 5250 Completeness (_total/calc) 98.93% 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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 50
13 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 21 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ...Each of the authors listed made significant contributions to this paper. Thank you for your consideration.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

The title compound, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone derivatives exhibit potent anti-inflammatory, anti-bacterial and anti-oxidant activity. Certain derivatives inhibit glutathione S-transferace (GST) but do not irritate the gastrointestinal tract. Curcumin, 1,5-di(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one, is a major constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, anti-bacterial, anti-oxidant, anti-hepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is non-toxic at high doses and substitution on the aromatic rings with electron-donating and -withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004). Recently, fluorinated organic compounds have attracted attention due to the ability of fluorine to act as a polar-hydrogen or hydroxyl mimic. Therefore, substitution of hydrogen by fluorine has been a strategy in designing molecules for biological activity studies (Filler & Kabayashi, 1992). Most recently, a redetermination of 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one at 120 (2) K (Harrison et al., 2006) and the crystal structure of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one have been reported (Butcher et al., 2006).

Related literature top

For the synthesis of the title compound, see: Furniss et al. (1989). For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004) and Filler & Kabayashi (1992), respectively. For related structures, see: Harrison et al. (2006); Butcher et al. (2006).

Experimental top

The title compound was synthesized according to the method reported in the literature (Furniss et al., 1989). A solution of of NaOH (25 g) in water (250 ml) and ethanol (200 ml) was placed in a 500 ml bolt head flask fitted with a mechanical stirrer. The flask was immersed in a water bath and the temperature of the solution was maintained at 393–398 K. The solution was stirred vigorously and to it was added one half of a previously prepared mixture of 4-fluorobenzaldehyde (31 g, 0.25 mol) and acetone (7.3 g, 0.125 mol). A flocculent precipitate formed within 2–3 minutes. After 15 minutes, the remainder of the aldehyde-acetone mixture was added and the stirring was continued for a further 30 min. The crude product obtained was filtered and washed with cold water to eliminate the alkali as completely as possible. The compound was purified from ethanol (yield:80%). The crystal growth was done in acetone:toluene (1:1) solvent by the slow evaporation technique; m.p. 383–387 K. Analysis for C17H12FO: Found (Calculated): C: 75.44 (75.55); H: 4.42 (4.48).

Refinement top

The H atoms were included in the riding model approximation with C—H = 0.95 Å, and with Uiso(H) = 1.17–1.21Ueq(C).

Structure description top

The title compound, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone derivatives exhibit potent anti-inflammatory, anti-bacterial and anti-oxidant activity. Certain derivatives inhibit glutathione S-transferace (GST) but do not irritate the gastrointestinal tract. Curcumin, 1,5-di(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one, is a major constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, anti-bacterial, anti-oxidant, anti-hepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is non-toxic at high doses and substitution on the aromatic rings with electron-donating and -withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004). Recently, fluorinated organic compounds have attracted attention due to the ability of fluorine to act as a polar-hydrogen or hydroxyl mimic. Therefore, substitution of hydrogen by fluorine has been a strategy in designing molecules for biological activity studies (Filler & Kabayashi, 1992). Most recently, a redetermination of 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one at 120 (2) K (Harrison et al., 2006) and the crystal structure of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one have been reported (Butcher et al., 2006).

For the synthesis of the title compound, see: Furniss et al. (1989). For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004) and Filler & Kabayashi (1992), respectively. For related structures, see: Harrison et al. (2006); Butcher et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of molecule A for C17H12FO, (I), showing atom labeling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of C17H12FO viewed down the a axis.
[Figure 3] Fig. 3. The formation of the title compound.
1,5-Bis(4-fluorophenyl)penta-1,4-dien-3-one top
Crystal data top
C17H12F2OF(000) = 1680
Mr = 270.27Dx = 1.365 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 90.019 (14) ÅCell parameters from 4065 reflections
b = 5.8228 (9) Åθ = 2.7–28.1°
c = 7.5301 (12) ŵ = 0.10 mm1
β = 90.868 (4)°T = 173 K
V = 3946.5 (11) Å3Chunk, colorless
Z = 120.50 × 0.25 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
Rint = 0.035
φ and ω scansθmax = 29.1°, θmin = 0.9°
5194 measured reflectionsh = 122122
5194 independent reflectionsk = 07
3837 reflections with I > 2σ(I)l = 010
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.144P)2 + 6.6257P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.094(Δ/σ)max = 0.035
wR(F2) = 0.275Δρmax = 0.58 e Å3
S = 1.06Δρmin = 0.33 e Å3
5194 reflectionsAbsolute structure: Flack (1983), 4789 Friedel pairs
541 parametersAbsolute structure parameter: 0.0 (13)
50 restraints
Crystal data top
C17H12F2OV = 3946.5 (11) Å3
Mr = 270.27Z = 12
Monoclinic, CcMo Kα radiation
a = 90.019 (14) ŵ = 0.10 mm1
b = 5.8228 (9) ÅT = 173 K
c = 7.5301 (12) Å0.50 × 0.25 × 0.15 mm
β = 90.868 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3837 reflections with I > 2σ(I)
5194 measured reflectionsRint = 0.035
5194 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.094H-atom parameters constrained
wR(F2) = 0.275Δρmax = 0.58 e Å3
S = 1.06Δρmin = 0.33 e Å3
5194 reflectionsAbsolute structure: Flack (1983), 4789 Friedel pairs
541 parametersAbsolute structure parameter: 0.0 (13)
50 restraints
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*/UeqOcc. (<1)
F1A0.27702 (2)1.0336 (4)0.16569 (16)0.0621 (6)
F2A0.12761 (2)0.8795 (4)0.39939 (18)0.0603 (6)
O1A0.20685 (3)0.1533 (4)0.0811 (3)0.0507 (6)
C1A0.24120 (3)0.6308 (5)0.0358 (3)0.0296 (6)
C2A0.25580 (3)0.5584 (5)0.0047 (4)0.0400 (7)
H2AA0.25740.41130.04690.048*
C3A0.26790 (3)0.6875 (6)0.0444 (4)0.0417 (8)
H3AA0.27770.63500.01920.050*
C4A0.26526 (3)0.9004 (6)0.1237 (3)0.0372 (7)
C5A0.25130 (3)0.9750 (5)0.1640 (3)0.0315 (6)
H5AA0.24991.11630.22490.038*
C6A0.23928 (3)0.8451 (5)0.1163 (3)0.0310 (6)
H6AA0.22950.90170.13840.037*
C7A0.22878 (3)0.4774 (5)0.0134 (4)0.0391 (7)
H7AA0.23100.31920.02860.047*
C8A0.21516 (3)0.5388 (5)0.0376 (3)0.0342 (7)
H8AA0.21230.69510.02550.041*
C9A0.20407 (3)0.3606 (5)0.0845 (3)0.0353 (7)
C10A0.18896 (3)0.4326 (5)0.1406 (4)0.0385 (7)
H10A0.18160.31600.14520.046*
C11A0.18483 (3)0.6404 (5)0.1841 (3)0.0311 (6)
H11A0.19200.75960.17910.037*
C12A0.16973 (3)0.7010 (5)0.2404 (3)0.0283 (6)
C13A0.15755 (3)0.5540 (5)0.2024 (3)0.0300 (6)
H13A0.15900.41460.13950.036*
C14A0.14334 (3)0.6158 (5)0.2582 (4)0.0348 (7)
H14A0.13500.51840.23610.042*
C15A0.14170 (3)0.8213 (5)0.3459 (4)0.0389 (7)
C16A0.15295 (3)0.9684 (5)0.3852 (4)0.0364 (7)
H16A0.15121.10780.44730.044*
C17A0.16707 (3)0.9064 (4)0.3308 (3)0.0299 (6)
H17A0.17521.00670.35570.036*
F1B0.11450 (2)0.3744 (4)0.4610 (2)0.0547 (6)
F2B0.03545 (2)0.5312 (4)1.0134 (2)0.0534 (6)
O1B0.03519 (3)0.3460 (4)0.7792 (3)0.0456 (6)
C1B0.07269 (3)0.1959 (5)0.6194 (3)0.0272 (6)
C2B0.08485 (3)0.0555 (4)0.6522 (3)0.0291 (6)
H2BA0.08340.08600.71230.035*
C3B0.09880 (3)0.1140 (5)0.6010 (4)0.0348 (7)
H3BA0.10700.01530.62560.042*
C4B0.10081 (3)0.3173 (6)0.5135 (4)0.0356 (7)
C5B0.08905 (3)0.4645 (5)0.4777 (4)0.0357 (7)
H5BA0.09060.60530.41710.043*
C6B0.07488 (3)0.4028 (5)0.5320 (3)0.0338 (7)
H6BA0.06670.50240.50920.041*
C7B0.05745 (3)0.1417 (5)0.6736 (3)0.0283 (6)
H7BA0.05050.26390.67760.034*
C8B0.05280 (3)0.0686 (5)0.7175 (3)0.0293 (6)
H8BA0.06010.18600.71450.035*
C9B0.03801 (3)0.1415 (4)0.7694 (3)0.0260 (6)
C10B0.02679 (3)0.0351 (5)0.8148 (4)0.0327 (7)
H10B0.02970.19140.82530.039*
C11B0.01251 (3)0.0249 (4)0.8412 (3)0.0250 (6)
H11B0.01020.18320.82810.030*
C12B0.00010 (3)0.1266 (5)0.8881 (3)0.0287 (6)
C13B0.01418 (3)0.0495 (5)0.8496 (3)0.0271 (6)
H13B0.01570.09570.79470.032*
C14B0.02632 (3)0.1887 (5)0.8927 (4)0.0353 (7)
H14B0.03620.14010.86660.042*
C15B0.02373 (3)0.3929 (5)0.9720 (4)0.0359 (7)
C16B0.00952 (3)0.4799 (5)1.0111 (4)0.0346 (7)
H16B0.00820.62661.06420.041*
C17B0.00251 (3)0.3412 (5)0.9686 (4)0.0312 (6)
H17B0.01230.39170.99400.037*
F1CA0.44648 (3)0.4141 (6)0.3573 (4)0.0623 (9)0.6844 (16)
F2CA0.29806 (3)0.5303 (6)0.2078 (4)0.0578 (8)0.6844 (16)
O1CA0.36780 (3)0.3478 (5)0.0692 (6)0.0507 (8)0.6844 (16)
F1CB0.44252 (7)0.5412 (14)0.3731 (10)0.0623 (9)0.32
F2CB0.29393 (7)0.3939 (13)0.1870 (10)0.0578 (8)0.32
O1CB0.37554 (8)0.3589 (12)0.0905 (12)0.0507 (8)0.32
C1C0.405100 (18)0.1904 (3)0.2208 (2)0.0276 (8)0.6844 (16)
C2C0.41751 (2)0.0561 (3)0.1830 (3)0.0289 (9)0.6844 (16)
H2CA0.41640.08730.12450.035*0.6844 (16)
C3C0.431549 (19)0.1317 (4)0.2306 (4)0.0364 (10)0.6844 (16)
H3CA0.44000.03990.20470.044*0.6844 (16)
C4C0.43317 (2)0.3416 (5)0.3161 (4)0.0306 (9)0.6844 (16)
C5C0.42076 (3)0.4759 (4)0.3539 (4)0.0279 (8)0.6844 (16)
H5CA0.42190.61930.41240.034*0.6844 (16)
C6C0.40672 (2)0.4003 (3)0.3063 (3)0.0253 (8)0.6844 (16)
H6CA0.39820.49210.33220.030*0.6844 (16)
C1CD0.40875 (5)0.1069 (7)0.2267 (6)0.0276 (8)0.32
C2CD0.42367 (5)0.0520 (8)0.2028 (7)0.0289 (9)0.32
H2CB0.42640.09180.15270.035*0.3156 (16)
C3CD0.43457 (4)0.2075 (10)0.2523 (9)0.0364 (10)0.32
H3CB0.44480.17000.23600.044*0.3156 (16)
C4CD0.43054 (6)0.4180 (10)0.3256 (9)0.0306 (9)0.32
C5CD0.41561 (6)0.4729 (8)0.3495 (9)0.0279 (8)0.32
H5CB0.41290.61680.39960.034*0.3156 (16)
C6CD0.40472 (5)0.3174 (7)0.3000 (7)0.0253 (8)0.32
H6CB0.39450.35490.31630.030*0.3156 (16)
C9C0.37021 (4)0.1462 (4)0.0794 (5)0.0342 (5)
C7CA0.38965 (4)0.1354 (7)0.1664 (5)0.0314 (8)0.6844 (16)
H7CA0.38270.25760.16000.038*0.6844 (16)
C8CA0.38508 (4)0.0754 (8)0.1261 (6)0.0346 (10)0.6844 (16)
H8CA0.39240.19280.12830.042*0.6844 (16)
C10C0.35928 (4)0.0388 (6)0.0231 (5)0.0273 (8)0.6844 (16)
H10C0.36230.19350.00670.033*0.6844 (16)
C11C0.34513 (4)0.0255 (6)0.0025 (5)0.0260 (7)0.6844 (16)
H11C0.34260.18270.01330.031*0.6844 (16)
C7CB0.39565 (10)0.0167 (16)0.1759 (11)0.0314 (8)0.32
H7CB0.39810.17370.15690.038*0.3156 (16)
C8CB0.38114 (10)0.0166 (18)0.1467 (13)0.0346 (10)0.32
H8CB0.37750.16590.17320.042*0.3156 (16)
C10D0.35532 (10)0.0780 (15)0.0381 (11)0.0273 (8)0.32
H10D0.34790.19310.03490.033*0.3156 (16)
C11D0.35145 (9)0.1373 (14)0.0040 (11)0.0260 (7)0.32
H11D0.35890.25130.01970.031*0.3156 (16)
C12C0.333494 (17)0.1331 (3)0.0532 (2)0.0227 (8)0.6844 (16)
C13C0.319100 (19)0.0514 (3)0.0286 (3)0.0256 (8)0.6844 (16)
H13C0.31750.09400.02550.031*0.6844 (16)
C14C0.307097 (17)0.1826 (4)0.0830 (4)0.0325 (9)0.6844 (16)
H14C0.29730.12680.06620.039*0.6844 (16)
C15C0.30949 (2)0.3954 (4)0.1621 (4)0.0267 (9)0.6844 (16)
C16C0.32388 (3)0.4770 (4)0.1867 (4)0.0288 (9)0.6844 (16)
H16C0.32550.62250.24070.035*0.6844 (16)
C17C0.33589 (2)0.3459 (3)0.1322 (3)0.0242 (8)0.6844 (16)
H17C0.34570.40170.14910.029*0.6844 (16)
C12D0.33677 (4)0.2175 (7)0.0559 (6)0.0227 (8)0.32
C13D0.32559 (5)0.0627 (8)0.0101 (7)0.0256 (8)0.32
H13D0.32800.07620.04910.031*0.3156 (16)
C14D0.31092 (4)0.1112 (10)0.0510 (8)0.0325 (9)0.32
H14D0.30330.00550.01980.039*0.3156 (16)
C15D0.30742 (4)0.3145 (11)0.1377 (8)0.0267 (9)0.32
C16D0.31859 (6)0.4692 (10)0.1834 (9)0.0288 (9)0.32
H16D0.31620.60820.24270.035*0.3156 (16)
C17D0.33327 (5)0.4207 (8)0.1425 (8)0.0242 (8)0.32
H17D0.34090.52650.17380.029*0.3156 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0356 (9)0.0683 (13)0.0826 (15)0.0186 (9)0.0055 (9)0.0110 (12)
F2A0.0407 (9)0.0771 (14)0.0639 (12)0.0103 (10)0.0235 (8)0.0040 (11)
O1A0.0467 (11)0.0380 (12)0.0679 (15)0.0046 (10)0.0145 (10)0.0030 (11)
C1A0.0286 (11)0.0370 (13)0.0233 (11)0.0004 (10)0.0032 (9)0.0070 (10)
C2A0.0576 (17)0.0244 (12)0.0377 (15)0.0124 (12)0.0068 (13)0.0056 (11)
C3A0.0292 (12)0.0463 (16)0.0497 (17)0.0055 (12)0.0006 (12)0.0048 (14)
C4A0.0349 (12)0.0496 (16)0.0273 (13)0.0104 (12)0.0049 (10)0.0032 (12)
C5A0.0392 (13)0.0261 (12)0.0294 (13)0.0065 (10)0.0025 (10)0.0001 (10)
C6A0.0278 (11)0.0394 (14)0.0257 (12)0.0039 (11)0.0009 (9)0.0016 (11)
C7A0.0507 (16)0.0369 (14)0.0297 (14)0.0046 (12)0.0004 (12)0.0024 (11)
C8A0.0312 (12)0.0361 (13)0.0352 (14)0.0015 (11)0.0002 (10)0.0067 (11)
C9A0.0418 (14)0.0324 (14)0.0314 (14)0.0032 (11)0.0072 (11)0.0051 (11)
C10A0.0445 (15)0.0317 (13)0.0392 (14)0.0131 (11)0.0057 (12)0.0144 (11)
C11A0.0233 (10)0.0400 (14)0.0301 (12)0.0008 (10)0.0012 (9)0.0071 (11)
C12A0.0280 (11)0.0304 (12)0.0265 (12)0.0001 (10)0.0017 (9)0.0055 (10)
C13A0.0275 (11)0.0338 (13)0.0288 (12)0.0002 (10)0.0014 (9)0.0027 (11)
C14A0.0247 (11)0.0396 (14)0.0400 (14)0.0037 (11)0.0002 (10)0.0097 (12)
C15A0.0416 (14)0.0482 (16)0.0271 (13)0.0147 (12)0.0092 (11)0.0026 (12)
C16A0.0495 (15)0.0321 (13)0.0280 (13)0.0050 (12)0.0061 (11)0.0027 (11)
C17A0.0405 (13)0.0239 (11)0.0253 (11)0.0048 (10)0.0006 (10)0.0052 (10)
F1B0.0345 (9)0.0549 (11)0.0748 (14)0.0174 (9)0.0101 (9)0.0090 (10)
F2B0.0378 (9)0.0656 (12)0.0569 (12)0.0209 (9)0.0065 (8)0.0092 (10)
O1B0.0501 (12)0.0207 (9)0.0663 (15)0.0024 (9)0.0086 (11)0.0016 (10)
C1B0.0268 (11)0.0370 (13)0.0178 (11)0.0028 (10)0.0050 (9)0.0005 (10)
C2B0.0401 (13)0.0184 (11)0.0289 (13)0.0015 (10)0.0021 (10)0.0008 (10)
C3B0.0330 (13)0.0378 (15)0.0338 (14)0.0066 (12)0.0064 (11)0.0021 (12)
C4B0.0225 (11)0.0398 (15)0.0447 (16)0.0039 (11)0.0065 (11)0.0066 (13)
C5B0.0517 (16)0.0265 (13)0.0290 (13)0.0072 (12)0.0035 (12)0.0037 (11)
C6B0.0354 (13)0.0369 (14)0.0289 (13)0.0106 (11)0.0032 (10)0.0119 (11)
C7B0.0323 (12)0.0256 (12)0.0269 (12)0.0093 (10)0.0024 (10)0.0069 (10)
C8B0.0199 (10)0.0421 (14)0.0262 (11)0.0023 (10)0.0113 (9)0.0048 (11)
C9B0.0204 (9)0.0256 (11)0.0323 (12)0.0037 (9)0.0096 (9)0.0056 (10)
C10B0.0308 (12)0.0289 (13)0.0386 (14)0.0013 (10)0.0086 (11)0.0116 (11)
C11B0.0218 (10)0.0242 (11)0.0291 (12)0.0032 (9)0.0061 (9)0.0013 (10)
C12B0.0273 (11)0.0279 (12)0.0311 (13)0.0072 (10)0.0033 (10)0.0021 (10)
C13B0.0245 (11)0.0293 (12)0.0276 (12)0.0002 (10)0.0059 (9)0.0040 (10)
C14B0.0251 (11)0.0477 (16)0.0331 (14)0.0032 (12)0.0006 (10)0.0069 (13)
C15B0.0270 (12)0.0405 (15)0.0406 (15)0.0102 (11)0.0079 (11)0.0010 (13)
C16B0.0427 (15)0.0309 (14)0.0301 (14)0.0022 (12)0.0014 (11)0.0019 (11)
C17B0.0279 (12)0.0348 (14)0.0309 (13)0.0037 (11)0.0033 (10)0.0031 (11)
F1CA0.0393 (12)0.083 (2)0.0649 (14)0.0235 (13)0.0191 (11)0.0180 (17)
F2CA0.0422 (13)0.0632 (18)0.0680 (16)0.0179 (13)0.0017 (12)0.0168 (15)
O1CA0.0414 (17)0.0303 (10)0.0809 (17)0.0108 (16)0.0130 (17)0.0017 (18)
F1CB0.0393 (12)0.083 (2)0.0649 (14)0.0235 (13)0.0191 (11)0.0180 (17)
F2CB0.0422 (13)0.0632 (18)0.0680 (16)0.0179 (13)0.0017 (12)0.0168 (15)
O1CB0.0414 (17)0.0303 (10)0.0809 (17)0.0108 (16)0.0130 (17)0.0017 (18)
C1C0.0400 (17)0.0231 (19)0.0196 (13)0.0020 (14)0.0004 (12)0.0015 (13)
C2C0.028 (2)0.0340 (15)0.0244 (14)0.0012 (16)0.0020 (14)0.0006 (12)
C3C0.0444 (19)0.030 (2)0.0345 (17)0.0000 (17)0.0019 (15)0.0008 (16)
C4C0.0306 (15)0.025 (2)0.0364 (16)0.0028 (14)0.0039 (12)0.0045 (15)
C5C0.027 (2)0.0336 (14)0.0235 (13)0.0114 (15)0.0017 (13)0.0035 (11)
C6C0.0295 (14)0.0172 (19)0.0290 (14)0.0061 (14)0.0007 (11)0.0018 (14)
C1CD0.0400 (17)0.0231 (19)0.0196 (13)0.0020 (14)0.0004 (12)0.0015 (13)
C2CD0.028 (2)0.0340 (15)0.0244 (14)0.0012 (16)0.0020 (14)0.0006 (12)
C3CD0.0444 (19)0.030 (2)0.0345 (17)0.0000 (17)0.0019 (15)0.0008 (16)
C4CD0.0306 (15)0.025 (2)0.0364 (16)0.0028 (14)0.0039 (12)0.0045 (15)
C5CD0.027 (2)0.0336 (14)0.0235 (13)0.0114 (15)0.0017 (13)0.0035 (11)
C6CD0.0295 (14)0.0172 (19)0.0290 (14)0.0061 (14)0.0007 (11)0.0018 (14)
C9C0.0316 (10)0.0308 (10)0.0403 (12)0.0035 (15)0.0008 (9)0.0014 (16)
C7CA0.0360 (17)0.0346 (16)0.0236 (15)0.0085 (13)0.0015 (13)0.0059 (14)
C8CA0.0253 (16)0.040 (2)0.0391 (17)0.0028 (15)0.0026 (14)0.0049 (18)
C10C0.0328 (16)0.0210 (16)0.0282 (15)0.0005 (13)0.0042 (13)0.0019 (14)
C11C0.0266 (15)0.0231 (14)0.0283 (16)0.0018 (12)0.0021 (12)0.0070 (13)
C7CB0.0360 (17)0.0346 (16)0.0236 (15)0.0085 (13)0.0015 (13)0.0059 (14)
C8CB0.0253 (16)0.040 (2)0.0391 (17)0.0028 (15)0.0026 (14)0.0049 (18)
C10D0.0328 (16)0.0210 (16)0.0282 (15)0.0005 (13)0.0042 (13)0.0019 (14)
C11D0.0266 (15)0.0231 (14)0.0283 (16)0.0018 (12)0.0021 (12)0.0070 (13)
C12C0.0214 (14)0.0251 (19)0.0214 (12)0.0034 (13)0.0077 (10)0.0012 (14)
C13C0.0082 (14)0.0335 (16)0.0351 (16)0.0028 (14)0.0035 (14)0.0026 (13)
C14C0.0238 (16)0.042 (2)0.0316 (16)0.0044 (15)0.0074 (13)0.0026 (16)
C15C0.0240 (14)0.026 (2)0.0296 (15)0.0017 (14)0.0015 (12)0.0079 (15)
C16C0.018 (2)0.0306 (15)0.0371 (16)0.0057 (15)0.0082 (15)0.0037 (12)
C17C0.0299 (15)0.0127 (17)0.0299 (14)0.0041 (13)0.0044 (12)0.0005 (14)
C12D0.0214 (14)0.0251 (19)0.0214 (12)0.0034 (13)0.0077 (10)0.0012 (14)
C13D0.0082 (14)0.0335 (16)0.0351 (16)0.0028 (14)0.0035 (14)0.0026 (13)
C14D0.0238 (16)0.042 (2)0.0316 (16)0.0044 (15)0.0074 (13)0.0026 (16)
C15D0.0240 (14)0.026 (2)0.0296 (15)0.0017 (14)0.0015 (12)0.0079 (15)
C16D0.018 (2)0.0306 (15)0.0371 (16)0.0057 (15)0.0082 (15)0.0037 (12)
C17D0.0299 (15)0.0127 (17)0.0299 (14)0.0041 (13)0.0044 (12)0.0005 (14)
Geometric parameters (Å, º) top
F1A—C4A1.354 (3)F1CA—C4C1.313 (3)
F2A—C15A1.379 (3)F2CA—C15C1.343 (3)
O1A—C9A1.233 (4)O1CA—C9C1.197 (4)
C1A—C2A1.397 (4)F1CB—C4CD1.348 (8)
C1A—C6A1.397 (4)F2CB—C15D1.356 (7)
C1A—C7A1.482 (4)O1CB—C9C1.331 (8)
C2A—C3A1.360 (4)C1C—C2C1.3900
C2A—H2AA0.9500C1C—C6C1.3900
C3A—C4A1.395 (4)C1C—C7CA1.491 (4)
C3A—H3AA0.9500C2C—C3C1.3900
C4A—C5A1.360 (4)C2C—H2CA0.9500
C5A—C6A1.372 (4)C3C—C4C1.3900
C5A—H5AA0.9500C3C—H3CA0.9500
C6A—H6AA0.9500C4C—C5C1.3900
C7A—C8A1.293 (4)C5C—C6C1.3900
C7A—H7AA0.9500C5C—H5CA0.9500
C8A—C9A1.486 (4)C6C—H6CA0.9500
C8A—H8AA0.9500C1CD—C2CD1.3900
C9A—C10A1.491 (4)C1CD—C6CD1.3900
C10A—C11A1.309 (4)C1CD—C7CB1.438 (10)
C10A—H10A0.9500C2CD—C3CD1.3900
C11A—C12A1.473 (4)C2CD—H2CB0.9500
C11A—H11A0.9500C3CD—C4CD1.3900
C12A—C17A1.399 (4)C3CD—H3CB0.9500
C12A—C13A1.417 (4)C4CD—C5CD1.3900
C13A—C14A1.399 (4)C5CD—C6CD1.3900
C13A—H13A0.9500C5CD—H5CB0.9500
C14A—C15A1.376 (4)C6CD—H6CB0.9500
C14A—H14A0.9500C9C—C10D1.437 (9)
C15A—C16A1.356 (4)C9C—C8CA1.449 (5)
C16A—C17A1.389 (4)C9C—C8CB1.462 (10)
C16A—H16A0.9500C9C—C10C1.523 (5)
C17A—H17A0.9500C7CA—C8CA1.331 (6)
F1B—C4B1.342 (3)C7CA—H7CA0.9500
F2B—C15B1.367 (3)C8CA—H8CA0.9500
O1B—C9B1.220 (3)C10C—C11C1.344 (5)
C1B—C2B1.385 (4)C10C—H10C0.9500
C1B—C6B1.389 (4)C11C—C12C1.452 (4)
C1B—C7B1.471 (4)C11C—H11C0.9500
C2B—C3B1.363 (4)C7CB—C8CB1.342 (12)
C2B—H2BA0.9500C7CB—H7CB0.9500
C3B—C4B1.368 (4)C8CB—H8CB0.9500
C3B—H3BA0.9500C10D—C11D1.327 (12)
C4B—C5B1.385 (4)C10D—H10D0.9500
C5B—C6B1.392 (4)C11D—C12D1.479 (9)
C5B—H5BA0.9500C11D—H11D0.9500
C6B—H6BA0.9500C12C—C13C1.3900
C7B—C8B1.338 (4)C12C—C17C1.3900
C7B—H7BA0.9500C13C—C14C1.3900
C8B—C9B1.457 (3)C13C—H13C0.9500
C8B—H8BA0.9500C14C—C15C1.3900
C9B—C10B1.485 (4)C14C—H14C0.9500
C10B—C11B1.349 (4)C15C—C16C1.3900
C10B—H10B0.9500C16C—C17C1.3900
C11B—C12B1.470 (4)C16C—H16C0.9500
C11B—H11B0.9500C17C—H17C0.9500
C12B—C13B1.389 (4)C12D—C13D1.3900
C12B—C17B1.404 (4)C12D—C17D1.3900
C13B—C14B1.403 (4)C13D—C14D1.3900
C13B—H13B0.9500C13D—H13D0.9500
C14B—C15B1.349 (4)C14D—C15D1.3900
C14B—H14B0.9500C14D—H14D0.9500
C15B—C16B1.403 (4)C15D—C16D1.3900
C16B—C17B1.392 (4)C16D—C17D1.3900
C16B—H16B0.9500C16D—H16D0.9500
C17B—H17B0.9500C17D—H17D0.9500
C2A—C1A—C6A116.9 (2)C1C—C2C—H2CA120.0
C2A—C1A—C7A119.2 (3)C2C—C3C—C4C120.0
C6A—C1A—C7A123.9 (2)C2C—C3C—H3CA120.0
C3A—C2A—C1A123.4 (3)C4C—C3C—H3CA120.0
C3A—C2A—H2AA118.3F1CA—C4C—C3C119.7 (2)
C1A—C2A—H2AA118.3F1CA—C4C—C5C120.3 (2)
C2A—C3A—C4A117.0 (3)C3C—C4C—C5C120.0
C2A—C3A—H3AA121.5C6C—C5C—C4C120.0
C4A—C3A—H3AA121.5C6C—C5C—H5CA120.0
F1A—C4A—C5A119.2 (3)C4C—C5C—H5CA120.0
F1A—C4A—C3A118.7 (3)C5C—C6C—C1C120.0
C5A—C4A—C3A122.0 (3)C5C—C6C—H6CA120.0
C4A—C5A—C6A119.7 (3)C1C—C6C—H6CA120.0
C4A—C5A—H5AA120.2C2CD—C1CD—C6CD120.0
C6A—C5A—H5AA120.2C2CD—C1CD—C7CB130.2 (4)
C5A—C6A—C1A120.9 (2)C6CD—C1CD—C7CB109.7 (4)
C5A—C6A—H6AA119.6C3CD—C2CD—C1CD120.0
C1A—C6A—H6AA119.6C3CD—C2CD—H2CB120.0
C8A—C7A—C1A126.1 (3)C1CD—C2CD—H2CB120.0
C8A—C7A—H7AA116.9C4CD—C3CD—C2CD120.0
C1A—C7A—H7AA116.9C4CD—C3CD—H3CB120.0
C7A—C8A—C9A118.9 (3)C2CD—C3CD—H3CB120.0
C7A—C8A—H8AA120.6F1CB—C4CD—C3CD111.7 (5)
C9A—C8A—H8AA120.6F1CB—C4CD—C5CD128.2 (5)
O1A—C9A—C8A122.8 (3)C3CD—C4CD—C5CD120.0
O1A—C9A—C10A117.8 (3)C6CD—C5CD—C4CD120.0
C8A—C9A—C10A119.4 (2)C6CD—C5CD—H5CB120.0
C11A—C10A—C9A126.5 (3)C4CD—C5CD—H5CB120.0
C11A—C10A—H10A116.8C5CD—C6CD—C1CD120.0
C9A—C10A—H10A116.8C5CD—C6CD—H6CB120.0
C10A—C11A—C12A124.1 (3)C1CD—C6CD—H6CB120.0
C10A—C11A—H11A118.0O1CA—C9C—O1CB32.6 (3)
C12A—C11A—H11A118.0O1CA—C9C—C10D95.0 (4)
C17A—C12A—C13A118.5 (2)O1CB—C9C—C10D127.5 (5)
C17A—C12A—C11A120.7 (2)O1CA—C9C—C8CA117.7 (3)
C13A—C12A—C11A120.8 (2)O1CB—C9C—C8CA85.1 (4)
C14A—C13A—C12A119.5 (2)C10D—C9C—C8CA147.4 (4)
C14A—C13A—H13A120.3O1CA—C9C—C8CB141.4 (5)
C12A—C13A—H13A120.2O1CB—C9C—C8CB109.6 (6)
C15A—C14A—C13A118.2 (3)C10D—C9C—C8CB122.1 (6)
C15A—C14A—H14A120.9C8CA—C9C—C8CB26.2 (4)
C13A—C14A—H14A120.9O1CA—C9C—C10C123.9 (4)
C16A—C15A—C14A124.7 (3)O1CB—C9C—C10C155.5 (5)
C16A—C15A—F2A117.9 (3)C10D—C9C—C10C30.2 (4)
C14A—C15A—F2A117.4 (3)C8CA—C9C—C10C118.0 (3)
C15A—C16A—C17A117.1 (3)C8CB—C9C—C10C94.5 (4)
C15A—C16A—H16A121.5C8CA—C7CA—C1C123.6 (3)
C17A—C16A—H16A121.5C8CA—C7CA—H7CA118.2
C16A—C17A—C12A122.0 (2)C1C—C7CA—H7CA118.2
C16A—C17A—H17A119.0C7CA—C8CA—C9C127.4 (4)
C12A—C17A—H17A119.0C7CA—C8CA—H8CA116.3
C2B—C1B—C6B118.6 (2)C9C—C8CA—H8CA116.3
C2B—C1B—C7B124.2 (2)C11C—C10C—C9C117.4 (3)
C6B—C1B—C7B117.2 (2)C11C—C10C—H10C121.3
C3B—C2B—C1B122.1 (3)C9C—C10C—H10C121.3
C3B—C2B—H2BA118.9C10C—C11C—C12C123.3 (3)
C1B—C2B—H2BA119.0C10C—C11C—H11C118.3
C2B—C3B—C4B118.8 (3)C12C—C11C—H11C118.3
C2B—C3B—H3BA120.6C8CB—C7CB—C1CD140.8 (9)
C4B—C3B—H3BA120.6C8CB—C7CB—H7CB109.6
F1B—C4B—C3B119.0 (3)C1CD—C7CB—H7CB109.6
F1B—C4B—C5B119.4 (3)C7CB—C8CB—C9C128.7 (9)
C3B—C4B—C5B121.5 (3)C7CB—C8CB—H8CB115.7
C4B—C5B—C6B118.9 (3)C9C—C8CB—H8CB115.7
C4B—C5B—H5BA120.5C11D—C10D—C9C123.5 (7)
C6B—C5B—H5BA120.5C11D—C10D—H10D118.3
C1B—C6B—C5B120.0 (3)C9C—C10D—H10D118.3
C1B—C6B—H6BA120.0C10D—C11D—C12D126.6 (7)
C5B—C6B—H6BA120.0C10D—C11D—H11D116.7
C8B—C7B—C1B124.2 (2)C12D—C11D—H11D116.7
C8B—C7B—H7BA117.9C13C—C12C—C17C120.0
C1B—C7B—H7BA117.9C13C—C12C—C11C114.99 (17)
C7B—C8B—C9B128.6 (3)C17C—C12C—C11C124.87 (17)
C7B—C8B—H8BA115.7C12C—C13C—C14C120.0
C9B—C8B—H8BA115.7C12C—C13C—H13C120.0
O1B—C9B—C8B119.5 (2)C14C—C13C—H13C120.0
O1B—C9B—C10B121.3 (2)C15C—C14C—C13C120.0
C8B—C9B—C10B119.2 (2)C15C—C14C—H14C120.0
C11B—C10B—C9B120.5 (2)C13C—C14C—H14C120.0
C11B—C10B—H10B119.7F2CA—C15C—C16C118.8 (2)
C9B—C10B—H10B119.7F2CA—C15C—C14C121.1 (2)
C10B—C11B—C12B127.5 (2)C16C—C15C—C14C120.0
C10B—C11B—H11B116.2C15C—C16C—C17C120.0
C12B—C11B—H11B116.2C15C—C16C—H16C120.0
C13B—C12B—C17B120.9 (2)C17C—C16C—H16C120.0
C13B—C12B—C11B117.4 (2)C16C—C17C—C12C120.0
C17B—C12B—C11B121.6 (2)C16C—C17C—H17C120.0
C12B—C13B—C14B119.2 (3)C12C—C17C—H17C120.0
C12B—C13B—H13B120.4C13D—C12D—C17D120.0
C14B—C13B—H13B120.4C13D—C12D—C11D111.5 (4)
C15B—C14B—C13B118.8 (3)C17D—C12D—C11D128.5 (4)
C15B—C14B—H14B120.6C14D—C13D—C12D120.0
C13B—C14B—H14B120.6C14D—C13D—H13D120.0
C14B—C15B—F2B119.4 (3)C12D—C13D—H13D120.0
C14B—C15B—C16B124.2 (3)C13D—C14D—C15D120.0
F2B—C15B—C16B116.3 (3)C13D—C14D—H14D120.0
C17B—C16B—C15B116.9 (3)C15D—C14D—H14D120.0
C17B—C16B—H16B121.6F2CB—C15D—C14D129.0 (5)
C15B—C16B—H16B121.6F2CB—C15D—C16D111.0 (5)
C16B—C17B—C12B120.0 (2)C14D—C15D—C16D120.0
C16B—C17B—H17B120.0C17D—C16D—C15D120.0
C12B—C17B—H17B120.0C17D—C16D—H16D120.0
C2C—C1C—C6C120.0C15D—C16D—H16D120.0
C2C—C1C—C7CA124.98 (18)C16D—C17D—C12D120.0
C6C—C1C—C7CA114.90 (18)C16D—C17D—H17D120.0
C3C—C2C—C1C120.0C12D—C17D—H17D120.0
C3C—C2C—H2CA120.0
C6A—C1A—C2A—C3A1.8 (4)C3C—C4C—C5C—C6C0.0
C7A—C1A—C2A—C3A179.6 (3)C4C—C5C—C6C—C1C0.0
C1A—C2A—C3A—C4A1.4 (4)C2C—C1C—C6C—C5C0.0
C2A—C3A—C4A—F1A179.8 (2)C7CA—C1C—C6C—C5C176.26 (19)
C2A—C3A—C4A—C5A1.5 (4)C6CD—C1CD—C2CD—C3CD0.0
F1A—C4A—C5A—C6A177.7 (2)C7CB—C1CD—C2CD—C3CD175.4 (6)
C3A—C4A—C5A—C6A4.0 (4)C1CD—C2CD—C3CD—C4CD0.0
C4A—C5A—C6A—C1A3.7 (4)C2CD—C3CD—C4CD—F1CB177.0 (6)
C2A—C1A—C6A—C5A0.8 (4)C2CD—C3CD—C4CD—C5CD0.0
C7A—C1A—C6A—C5A177.7 (2)F1CB—C4CD—C5CD—C6CD176.5 (7)
C2A—C1A—C7A—C8A160.4 (3)C3CD—C4CD—C5CD—C6CD0.0
C6A—C1A—C7A—C8A21.0 (4)C4CD—C5CD—C6CD—C1CD0.0
C1A—C7A—C8A—C9A179.3 (2)C2CD—C1CD—C6CD—C5CD0.0
C7A—C8A—C9A—O1A8.8 (4)C7CB—C1CD—C6CD—C5CD176.2 (5)
C7A—C8A—C9A—C10A170.4 (3)C2C—C1C—C7CA—C8CA22.0 (5)
O1A—C9A—C10A—C11A166.4 (3)C6C—C1C—C7CA—C8CA161.9 (3)
C8A—C9A—C10A—C11A12.9 (4)C1C—C7CA—C8CA—C9C177.2 (3)
C9A—C10A—C11A—C12A179.3 (2)O1CA—C9C—C8CA—C7CA170.8 (4)
C10A—C11A—C12A—C17A162.1 (3)O1CB—C9C—C8CA—C7CA171.6 (6)
C10A—C11A—C12A—C13A18.7 (4)C10D—C9C—C8CA—C7CA7.3 (12)
C17A—C12A—C13A—C14A1.0 (4)C8CB—C9C—C8CA—C7CA11.5 (9)
C11A—C12A—C13A—C14A179.8 (2)C10C—C9C—C8CA—C7CA17.0 (6)
C12A—C13A—C14A—C15A1.2 (4)O1CA—C9C—C10C—C11C14.9 (6)
C13A—C14A—C15A—C16A1.1 (4)O1CB—C9C—C10C—C11C27.6 (14)
C13A—C14A—C15A—F2A179.8 (2)C10D—C9C—C10C—C11C3.9 (7)
C14A—C15A—C16A—C17A0.7 (4)C8CA—C9C—C10C—C11C173.4 (4)
F2A—C15A—C16A—C17A179.8 (2)C8CB—C9C—C10C—C11C161.2 (5)
C15A—C16A—C17A—C12A0.5 (4)C9C—C10C—C11C—C12C178.9 (3)
C13A—C12A—C17A—C16A0.7 (4)C2CD—C1CD—C7CB—C8CB159.8 (10)
C11A—C12A—C17A—C16A179.9 (2)C6CD—C1CD—C7CB—C8CB15.9 (13)
C6B—C1B—C2B—C3B0.2 (4)C1CD—C7CB—C8CB—C9C174.4 (8)
C7B—C1B—C2B—C3B179.3 (2)O1CA—C9C—C8CB—C7CB24.8 (16)
C1B—C2B—C3B—C4B0.4 (4)O1CB—C9C—C8CB—C7CB15.8 (12)
C2B—C3B—C4B—F1B179.2 (3)C10D—C9C—C8CB—C7CB173.5 (9)
C2B—C3B—C4B—C5B0.6 (4)C8CA—C9C—C8CB—C7CB5.4 (6)
F1B—C4B—C5B—C6B179.6 (3)C10C—C9C—C8CB—C7CB160.3 (10)
C3B—C4B—C5B—C6B0.2 (4)O1CA—C9C—C10D—C11D169.9 (8)
C2B—C1B—C6B—C5B0.6 (4)O1CB—C9C—C10D—C11D169.7 (8)
C7B—C1B—C6B—C5B179.8 (2)C8CA—C9C—C10D—C11D11.8 (15)
C4B—C5B—C6B—C1B0.5 (4)C8CB—C9C—C10D—C11D21.4 (11)
C2B—C1B—C7B—C8B18.2 (4)C10C—C9C—C10D—C11D5.5 (5)
C6B—C1B—C7B—C8B162.7 (3)C9C—C10D—C11D—C12D173.8 (6)
C1B—C7B—C8B—C9B178.7 (2)C10C—C11C—C12C—C13C163.8 (3)
C7B—C8B—C9B—O1B169.0 (3)C10C—C11C—C12C—C17C20.5 (4)
C7B—C8B—C9B—C10B12.9 (4)C17C—C12C—C13C—C14C0.0
O1B—C9B—C10B—C11B10.4 (4)C11C—C12C—C13C—C14C175.9 (2)
C8B—C9B—C10B—C11B171.5 (2)C12C—C13C—C14C—C15C0.0
C9B—C10B—C11B—C12B179.5 (2)C13C—C14C—C15C—F2CA176.7 (3)
C10B—C11B—C12B—C13B158.1 (3)C13C—C14C—C15C—C16C0.0
C10B—C11B—C12B—C17B21.8 (4)F2CA—C15C—C16C—C17C176.7 (3)
C17B—C12B—C13B—C14B0.3 (4)C14C—C15C—C16C—C17C0.0
C11B—C12B—C13B—C14B179.8 (2)C15C—C16C—C17C—C12C0.0
C12B—C13B—C14B—C15B0.6 (4)C13C—C12C—C17C—C16C0.0
C13B—C14B—C15B—F2B179.4 (2)C11C—C12C—C17C—C16C175.4 (2)
C13B—C14B—C15B—C16B1.6 (5)C10D—C11D—C12D—C13D23.1 (10)
C14B—C15B—C16B—C17B1.7 (5)C10D—C11D—C12D—C17D158.8 (7)
F2B—C15B—C16B—C17B179.6 (2)C17D—C12D—C13D—C14D0.0
C15B—C16B—C17B—C12B0.8 (4)C11D—C12D—C13D—C14D178.3 (4)
C13B—C12B—C17B—C16B0.1 (4)C12D—C13D—C14D—C15D0.0
C11B—C12B—C17B—C16B180.0 (3)C13D—C14D—C15D—F2CB179.2 (7)
C6C—C1C—C2C—C3C0.0C13D—C14D—C15D—C16D0.0
C7CA—C1C—C2C—C3C175.9 (2)F2CB—C15D—C16D—C17D179.3 (5)
C1C—C2C—C3C—C4C0.0C14D—C15D—C16D—C17D0.0
C2C—C3C—C4C—F1CA178.6 (3)C15D—C16D—C17D—C12D0.0
C2C—C3C—C4C—C5C0.0C13D—C12D—C17D—C16D0.0
F1CA—C4C—C5C—C6C178.6 (3)C11D—C12D—C17D—C16D178.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7CA—H7CA···O1CBi0.952.383.260 (8)153
C11D—H11D···O1CAi0.952.503.379 (9)154
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H12F2O
Mr270.27
Crystal system, space groupMonoclinic, Cc
Temperature (K)173
a, b, c (Å)90.019 (14), 5.8228 (9), 7.5301 (12)
β (°) 90.868 (4)
V3)3946.5 (11)
Z12
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5194, 5194, 3837
Rint0.035
(sin θ/λ)max1)0.683
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.094, 0.275, 1.06
No. of reflections5194
No. of parameters541
No. of restraints50
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.33
Absolute structureFlack (1983), 4789 Friedel pairs
Absolute structure parameter0.0 (13)

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2006), SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7CA—H7CA···O1CBi0.952.383.260 (8)153.2
C11D—H11D···O1CAi0.952.503.379 (9)154.2
Symmetry code: (i) x, y+1, z.
 

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