Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026116/tk2156sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026116/tk2156Isup2.hkl |
CCDC reference: 654956
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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).
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).
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).
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).
C17H12F2O | F(000) = 1680 |
Mr = 270.27 | Dx = 1.365 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 90.019 (14) Å | Cell parameters from 4065 reflections |
b = 5.8228 (9) Å | θ = 2.7–28.1° |
c = 7.5301 (12) Å | µ = 0.10 mm−1 |
β = 90.868 (4)° | T = 173 K |
V = 3946.5 (11) Å3 | Chunk, colorless |
Z = 12 | 0.50 × 0.25 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | Rint = 0.035 |
φ and ω scans | θmax = 29.1°, θmin = 0.9° |
5194 measured reflections | h = −122→122 |
5194 independent reflections | k = 0→7 |
3837 reflections with I > 2σ(I) | l = 0→10 |
Refinement on F2 | H-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) = 0.275 | Δρmax = 0.58 e Å−3 |
S = 1.06 | Δρmin = −0.33 e Å−3 |
5194 reflections | Absolute structure: Flack (1983), 4789 Friedel pairs |
541 parameters | Absolute structure parameter: 0.0 (13) |
50 restraints |
C17H12F2O | V = 3946.5 (11) Å3 |
Mr = 270.27 | Z = 12 |
Monoclinic, Cc | Mo Kα radiation |
a = 90.019 (14) Å | µ = 0.10 mm−1 |
b = 5.8228 (9) Å | T = 173 K |
c = 7.5301 (12) Å | 0.50 × 0.25 × 0.15 mm |
β = 90.868 (4)° |
Bruker SMART CCD area-detector diffractometer | 3837 reflections with I > 2σ(I) |
5194 measured reflections | Rint = 0.035 |
5194 independent reflections |
R[F2 > 2σ(F2)] = 0.094 | H-atom parameters constrained |
wR(F2) = 0.275 | Δρmax = 0.58 e Å−3 |
S = 1.06 | Δρmin = −0.33 e Å−3 |
5194 reflections | Absolute structure: Flack (1983), 4789 Friedel pairs |
541 parameters | Absolute structure parameter: 0.0 (13) |
50 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1A | 0.27702 (2) | 1.0336 (4) | −0.16569 (16) | 0.0621 (6) | |
F2A | 0.12761 (2) | 0.8795 (4) | 0.39939 (18) | 0.0603 (6) | |
O1A | 0.20685 (3) | 0.1533 (4) | 0.0811 (3) | 0.0507 (6) | |
C1A | 0.24120 (3) | 0.6308 (5) | −0.0358 (3) | 0.0296 (6) | |
C2A | 0.25580 (3) | 0.5584 (5) | −0.0047 (4) | 0.0400 (7) | |
H2AA | 0.2574 | 0.4113 | 0.0469 | 0.048* | |
C3A | 0.26790 (3) | 0.6875 (6) | −0.0444 (4) | 0.0417 (8) | |
H3AA | 0.2777 | 0.6350 | −0.0192 | 0.050* | |
C4A | 0.26526 (3) | 0.9004 (6) | −0.1237 (3) | 0.0372 (7) | |
C5A | 0.25130 (3) | 0.9750 (5) | −0.1640 (3) | 0.0315 (6) | |
H5AA | 0.2499 | 1.1163 | −0.2249 | 0.038* | |
C6A | 0.23928 (3) | 0.8451 (5) | −0.1163 (3) | 0.0310 (6) | |
H6AA | 0.2295 | 0.9017 | −0.1384 | 0.037* | |
C7A | 0.22878 (3) | 0.4774 (5) | 0.0134 (4) | 0.0391 (7) | |
H7AA | 0.2310 | 0.3192 | 0.0286 | 0.047* | |
C8A | 0.21516 (3) | 0.5388 (5) | 0.0376 (3) | 0.0342 (7) | |
H8AA | 0.2123 | 0.6951 | 0.0255 | 0.041* | |
C9A | 0.20407 (3) | 0.3606 (5) | 0.0845 (3) | 0.0353 (7) | |
C10A | 0.18896 (3) | 0.4326 (5) | 0.1406 (4) | 0.0385 (7) | |
H10A | 0.1816 | 0.3160 | 0.1452 | 0.046* | |
C11A | 0.18483 (3) | 0.6404 (5) | 0.1841 (3) | 0.0311 (6) | |
H11A | 0.1920 | 0.7596 | 0.1791 | 0.037* | |
C12A | 0.16973 (3) | 0.7010 (5) | 0.2404 (3) | 0.0283 (6) | |
C13A | 0.15755 (3) | 0.5540 (5) | 0.2024 (3) | 0.0300 (6) | |
H13A | 0.1590 | 0.4146 | 0.1395 | 0.036* | |
C14A | 0.14334 (3) | 0.6158 (5) | 0.2582 (4) | 0.0348 (7) | |
H14A | 0.1350 | 0.5184 | 0.2361 | 0.042* | |
C15A | 0.14170 (3) | 0.8213 (5) | 0.3459 (4) | 0.0389 (7) | |
C16A | 0.15295 (3) | 0.9684 (5) | 0.3852 (4) | 0.0364 (7) | |
H16A | 0.1512 | 1.1078 | 0.4473 | 0.044* | |
C17A | 0.16707 (3) | 0.9064 (4) | 0.3308 (3) | 0.0299 (6) | |
H17A | 0.1752 | 1.0067 | 0.3557 | 0.036* | |
F1B | 0.11450 (2) | 0.3744 (4) | 0.4610 (2) | 0.0547 (6) | |
F2B | −0.03545 (2) | 0.5312 (4) | 1.0134 (2) | 0.0534 (6) | |
O1B | 0.03519 (3) | −0.3460 (4) | 0.7792 (3) | 0.0456 (6) | |
C1B | 0.07269 (3) | 0.1959 (5) | 0.6194 (3) | 0.0272 (6) | |
C2B | 0.08485 (3) | 0.0555 (4) | 0.6522 (3) | 0.0291 (6) | |
H2BA | 0.0834 | −0.0860 | 0.7123 | 0.035* | |
C3B | 0.09880 (3) | 0.1140 (5) | 0.6010 (4) | 0.0348 (7) | |
H3BA | 0.1070 | 0.0153 | 0.6256 | 0.042* | |
C4B | 0.10081 (3) | 0.3173 (6) | 0.5135 (4) | 0.0356 (7) | |
C5B | 0.08905 (3) | 0.4645 (5) | 0.4777 (4) | 0.0357 (7) | |
H5BA | 0.0906 | 0.6053 | 0.4171 | 0.043* | |
C6B | 0.07488 (3) | 0.4028 (5) | 0.5320 (3) | 0.0338 (7) | |
H6BA | 0.0667 | 0.5024 | 0.5092 | 0.041* | |
C7B | 0.05745 (3) | 0.1417 (5) | 0.6736 (3) | 0.0283 (6) | |
H7BA | 0.0505 | 0.2639 | 0.6776 | 0.034* | |
C8B | 0.05280 (3) | −0.0686 (5) | 0.7175 (3) | 0.0293 (6) | |
H8BA | 0.0601 | −0.1860 | 0.7145 | 0.035* | |
C9B | 0.03801 (3) | −0.1415 (4) | 0.7694 (3) | 0.0260 (6) | |
C10B | 0.02679 (3) | 0.0351 (5) | 0.8148 (4) | 0.0327 (7) | |
H10B | 0.0297 | 0.1914 | 0.8253 | 0.039* | |
C11B | 0.01251 (3) | −0.0249 (4) | 0.8412 (3) | 0.0250 (6) | |
H11B | 0.0102 | −0.1832 | 0.8281 | 0.030* | |
C12B | 0.00010 (3) | 0.1266 (5) | 0.8881 (3) | 0.0287 (6) | |
C13B | −0.01418 (3) | 0.0495 (5) | 0.8496 (3) | 0.0271 (6) | |
H13B | −0.0157 | −0.0957 | 0.7947 | 0.032* | |
C14B | −0.02632 (3) | 0.1887 (5) | 0.8927 (4) | 0.0353 (7) | |
H14B | −0.0362 | 0.1401 | 0.8666 | 0.042* | |
C15B | −0.02373 (3) | 0.3929 (5) | 0.9720 (4) | 0.0359 (7) | |
C16B | −0.00952 (3) | 0.4799 (5) | 1.0111 (4) | 0.0346 (7) | |
H16B | −0.0082 | 0.6266 | 1.0642 | 0.041* | |
C17B | 0.00251 (3) | 0.3412 (5) | 0.9686 (4) | 0.0312 (6) | |
H17B | 0.0123 | 0.3917 | 0.9940 | 0.037* | |
F1CA | 0.44648 (3) | 0.4141 (6) | −0.3573 (4) | 0.0623 (9) | 0.6844 (16) |
F2CA | 0.29806 (3) | 0.5303 (6) | 0.2078 (4) | 0.0578 (8) | 0.6844 (16) |
O1CA | 0.36780 (3) | −0.3478 (5) | −0.0692 (6) | 0.0507 (8) | 0.6844 (16) |
F1CB | 0.44252 (7) | 0.5412 (14) | −0.3731 (10) | 0.0623 (9) | 0.32 |
F2CB | 0.29393 (7) | 0.3939 (13) | 0.1870 (10) | 0.0578 (8) | 0.32 |
O1CB | 0.37554 (8) | −0.3589 (12) | −0.0905 (12) | 0.0507 (8) | 0.32 |
C1C | 0.405100 (18) | 0.1904 (3) | −0.2208 (2) | 0.0276 (8) | 0.6844 (16) |
C2C | 0.41751 (2) | 0.0561 (3) | −0.1830 (3) | 0.0289 (9) | 0.6844 (16) |
H2CA | 0.4164 | −0.0873 | −0.1245 | 0.035* | 0.6844 (16) |
C3C | 0.431549 (19) | 0.1317 (4) | −0.2306 (4) | 0.0364 (10) | 0.6844 (16) |
H3CA | 0.4400 | 0.0399 | −0.2047 | 0.044* | 0.6844 (16) |
C4C | 0.43317 (2) | 0.3416 (5) | −0.3161 (4) | 0.0306 (9) | 0.6844 (16) |
C5C | 0.42076 (3) | 0.4759 (4) | −0.3539 (4) | 0.0279 (8) | 0.6844 (16) |
H5CA | 0.4219 | 0.6193 | −0.4124 | 0.034* | 0.6844 (16) |
C6C | 0.40672 (2) | 0.4003 (3) | −0.3063 (3) | 0.0253 (8) | 0.6844 (16) |
H6CA | 0.3982 | 0.4921 | −0.3322 | 0.030* | 0.6844 (16) |
C1CD | 0.40875 (5) | 0.1069 (7) | −0.2267 (6) | 0.0276 (8) | 0.32 |
C2CD | 0.42367 (5) | 0.0520 (8) | −0.2028 (7) | 0.0289 (9) | 0.32 |
H2CB | 0.4264 | −0.0918 | −0.1527 | 0.035* | 0.3156 (16) |
C3CD | 0.43457 (4) | 0.2075 (10) | −0.2523 (9) | 0.0364 (10) | 0.32 |
H3CB | 0.4448 | 0.1700 | −0.2360 | 0.044* | 0.3156 (16) |
C4CD | 0.43054 (6) | 0.4180 (10) | −0.3256 (9) | 0.0306 (9) | 0.32 |
C5CD | 0.41561 (6) | 0.4729 (8) | −0.3495 (9) | 0.0279 (8) | 0.32 |
H5CB | 0.4129 | 0.6168 | −0.3996 | 0.034* | 0.3156 (16) |
C6CD | 0.40472 (5) | 0.3174 (7) | −0.3000 (7) | 0.0253 (8) | 0.32 |
H6CB | 0.3945 | 0.3549 | −0.3163 | 0.030* | 0.3156 (16) |
C9C | 0.37021 (4) | −0.1462 (4) | −0.0794 (5) | 0.0342 (5) | |
C7CA | 0.38965 (4) | 0.1354 (7) | −0.1664 (5) | 0.0314 (8) | 0.6844 (16) |
H7CA | 0.3827 | 0.2576 | −0.1600 | 0.038* | 0.6844 (16) |
C8CA | 0.38508 (4) | −0.0754 (8) | −0.1261 (6) | 0.0346 (10) | 0.6844 (16) |
H8CA | 0.3924 | −0.1928 | −0.1283 | 0.042* | 0.6844 (16) |
C10C | 0.35928 (4) | 0.0388 (6) | −0.0231 (5) | 0.0273 (8) | 0.6844 (16) |
H10C | 0.3623 | 0.1935 | −0.0067 | 0.033* | 0.6844 (16) |
C11C | 0.34513 (4) | −0.0255 (6) | 0.0025 (5) | 0.0260 (7) | 0.6844 (16) |
H11C | 0.3426 | −0.1827 | −0.0133 | 0.031* | 0.6844 (16) |
C7CB | 0.39565 (10) | −0.0167 (16) | −0.1759 (11) | 0.0314 (8) | 0.32 |
H7CB | 0.3981 | −0.1737 | −0.1569 | 0.038* | 0.3156 (16) |
C8CB | 0.38114 (10) | 0.0166 (18) | −0.1467 (13) | 0.0346 (10) | 0.32 |
H8CB | 0.3775 | 0.1659 | −0.1732 | 0.042* | 0.3156 (16) |
C10D | 0.35532 (10) | −0.0780 (15) | −0.0381 (11) | 0.0273 (8) | 0.32 |
H10D | 0.3479 | −0.1931 | −0.0349 | 0.033* | 0.3156 (16) |
C11D | 0.35145 (9) | 0.1373 (14) | −0.0040 (11) | 0.0260 (7) | 0.32 |
H11D | 0.3589 | 0.2513 | −0.0197 | 0.031* | 0.3156 (16) |
C12C | 0.333494 (17) | 0.1331 (3) | 0.0532 (2) | 0.0227 (8) | 0.6844 (16) |
C13C | 0.319100 (19) | 0.0514 (3) | 0.0286 (3) | 0.0256 (8) | 0.6844 (16) |
H13C | 0.3175 | −0.0940 | −0.0255 | 0.031* | 0.6844 (16) |
C14C | 0.307097 (17) | 0.1826 (4) | 0.0830 (4) | 0.0325 (9) | 0.6844 (16) |
H14C | 0.2973 | 0.1268 | 0.0662 | 0.039* | 0.6844 (16) |
C15C | 0.30949 (2) | 0.3954 (4) | 0.1621 (4) | 0.0267 (9) | 0.6844 (16) |
C16C | 0.32388 (3) | 0.4770 (4) | 0.1867 (4) | 0.0288 (9) | 0.6844 (16) |
H16C | 0.3255 | 0.6225 | 0.2407 | 0.035* | 0.6844 (16) |
C17C | 0.33589 (2) | 0.3459 (3) | 0.1322 (3) | 0.0242 (8) | 0.6844 (16) |
H17C | 0.3457 | 0.4017 | 0.1491 | 0.029* | 0.6844 (16) |
C12D | 0.33677 (4) | 0.2175 (7) | 0.0559 (6) | 0.0227 (8) | 0.32 |
C13D | 0.32559 (5) | 0.0627 (8) | 0.0101 (7) | 0.0256 (8) | 0.32 |
H13D | 0.3280 | −0.0762 | −0.0491 | 0.031* | 0.3156 (16) |
C14D | 0.31092 (4) | 0.1112 (10) | 0.0510 (8) | 0.0325 (9) | 0.32 |
H14D | 0.3033 | 0.0055 | 0.0198 | 0.039* | 0.3156 (16) |
C15D | 0.30742 (4) | 0.3145 (11) | 0.1377 (8) | 0.0267 (9) | 0.32 |
C16D | 0.31859 (6) | 0.4692 (10) | 0.1834 (9) | 0.0288 (9) | 0.32 |
H16D | 0.3162 | 0.6082 | 0.2427 | 0.035* | 0.3156 (16) |
C17D | 0.33327 (5) | 0.4207 (8) | 0.1425 (8) | 0.0242 (8) | 0.32 |
H17D | 0.3409 | 0.5265 | 0.1738 | 0.029* | 0.3156 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1A | 0.0356 (9) | 0.0683 (13) | 0.0826 (15) | −0.0186 (9) | 0.0055 (9) | 0.0110 (12) |
F2A | 0.0407 (9) | 0.0771 (14) | 0.0639 (12) | 0.0103 (10) | 0.0235 (8) | −0.0040 (11) |
O1A | 0.0467 (11) | 0.0380 (12) | 0.0679 (15) | 0.0046 (10) | 0.0145 (10) | 0.0030 (11) |
C1A | 0.0286 (11) | 0.0370 (13) | 0.0233 (11) | 0.0004 (10) | 0.0032 (9) | −0.0070 (10) |
C2A | 0.0576 (17) | 0.0244 (12) | 0.0377 (15) | 0.0124 (12) | −0.0068 (13) | −0.0056 (11) |
C3A | 0.0292 (12) | 0.0463 (16) | 0.0497 (17) | 0.0055 (12) | 0.0006 (12) | 0.0048 (14) |
C4A | 0.0349 (12) | 0.0496 (16) | 0.0273 (13) | −0.0104 (12) | 0.0049 (10) | −0.0032 (12) |
C5A | 0.0392 (13) | 0.0261 (12) | 0.0294 (13) | −0.0065 (10) | 0.0025 (10) | −0.0001 (10) |
C6A | 0.0278 (11) | 0.0394 (14) | 0.0257 (12) | 0.0039 (11) | −0.0009 (9) | −0.0016 (11) |
C7A | 0.0507 (16) | 0.0369 (14) | 0.0297 (14) | −0.0046 (12) | 0.0004 (12) | 0.0024 (11) |
C8A | 0.0312 (12) | 0.0361 (13) | 0.0352 (14) | 0.0015 (11) | 0.0002 (10) | −0.0067 (11) |
C9A | 0.0418 (14) | 0.0324 (14) | 0.0314 (14) | 0.0032 (11) | −0.0072 (11) | −0.0051 (11) |
C10A | 0.0445 (15) | 0.0317 (13) | 0.0392 (14) | −0.0131 (11) | −0.0057 (12) | 0.0144 (11) |
C11A | 0.0233 (10) | 0.0400 (14) | 0.0301 (12) | −0.0008 (10) | 0.0012 (9) | −0.0071 (11) |
C12A | 0.0280 (11) | 0.0304 (12) | 0.0265 (12) | −0.0001 (10) | −0.0017 (9) | 0.0055 (10) |
C13A | 0.0275 (11) | 0.0338 (13) | 0.0288 (12) | −0.0002 (10) | 0.0014 (9) | −0.0027 (11) |
C14A | 0.0247 (11) | 0.0396 (14) | 0.0400 (14) | −0.0037 (11) | −0.0002 (10) | 0.0097 (12) |
C15A | 0.0416 (14) | 0.0482 (16) | 0.0271 (13) | 0.0147 (12) | 0.0092 (11) | 0.0026 (12) |
C16A | 0.0495 (15) | 0.0321 (13) | 0.0280 (13) | 0.0050 (12) | 0.0061 (11) | 0.0027 (11) |
C17A | 0.0405 (13) | 0.0239 (11) | 0.0253 (11) | −0.0048 (10) | −0.0006 (10) | −0.0052 (10) |
F1B | 0.0345 (9) | 0.0549 (11) | 0.0748 (14) | −0.0174 (9) | 0.0101 (9) | 0.0090 (10) |
F2B | 0.0378 (9) | 0.0656 (12) | 0.0569 (12) | 0.0209 (9) | 0.0065 (8) | −0.0092 (10) |
O1B | 0.0501 (12) | 0.0207 (9) | 0.0663 (15) | 0.0024 (9) | 0.0086 (11) | 0.0016 (10) |
C1B | 0.0268 (11) | 0.0370 (13) | 0.0178 (11) | −0.0028 (10) | 0.0050 (9) | −0.0005 (10) |
C2B | 0.0401 (13) | 0.0184 (11) | 0.0289 (13) | 0.0015 (10) | −0.0021 (10) | −0.0008 (10) |
C3B | 0.0330 (13) | 0.0378 (15) | 0.0338 (14) | 0.0066 (12) | 0.0064 (11) | 0.0021 (12) |
C4B | 0.0225 (11) | 0.0398 (15) | 0.0447 (16) | −0.0039 (11) | 0.0065 (11) | −0.0066 (13) |
C5B | 0.0517 (16) | 0.0265 (13) | 0.0290 (13) | −0.0072 (12) | 0.0035 (12) | 0.0037 (11) |
C6B | 0.0354 (13) | 0.0369 (14) | 0.0289 (13) | 0.0106 (11) | −0.0032 (10) | −0.0119 (11) |
C7B | 0.0323 (12) | 0.0256 (12) | 0.0269 (12) | 0.0093 (10) | 0.0024 (10) | −0.0069 (10) |
C8B | 0.0199 (10) | 0.0421 (14) | 0.0262 (11) | −0.0023 (10) | 0.0113 (9) | 0.0048 (11) |
C9B | 0.0204 (9) | 0.0256 (11) | 0.0323 (12) | 0.0037 (9) | 0.0096 (9) | −0.0056 (10) |
C10B | 0.0308 (12) | 0.0289 (13) | 0.0386 (14) | 0.0013 (10) | 0.0086 (11) | −0.0116 (11) |
C11B | 0.0218 (10) | 0.0242 (11) | 0.0291 (12) | −0.0032 (9) | 0.0061 (9) | 0.0013 (10) |
C12B | 0.0273 (11) | 0.0279 (12) | 0.0311 (13) | 0.0072 (10) | 0.0033 (10) | −0.0021 (10) |
C13B | 0.0245 (11) | 0.0293 (12) | 0.0276 (12) | −0.0002 (10) | 0.0059 (9) | −0.0040 (10) |
C14B | 0.0251 (11) | 0.0477 (16) | 0.0331 (14) | −0.0032 (12) | 0.0006 (10) | 0.0069 (13) |
C15B | 0.0270 (12) | 0.0405 (15) | 0.0406 (15) | 0.0102 (11) | 0.0079 (11) | −0.0010 (13) |
C16B | 0.0427 (15) | 0.0309 (14) | 0.0301 (14) | −0.0022 (12) | 0.0014 (11) | −0.0019 (11) |
C17B | 0.0279 (12) | 0.0348 (14) | 0.0309 (13) | −0.0037 (11) | 0.0033 (10) | 0.0031 (11) |
F1CA | 0.0393 (12) | 0.083 (2) | 0.0649 (14) | −0.0235 (13) | 0.0191 (11) | −0.0180 (17) |
F2CA | 0.0422 (13) | 0.0632 (18) | 0.0680 (16) | 0.0179 (13) | 0.0017 (12) | −0.0168 (15) |
O1CA | 0.0414 (17) | 0.0303 (10) | 0.0809 (17) | −0.0108 (16) | 0.0130 (17) | −0.0017 (18) |
F1CB | 0.0393 (12) | 0.083 (2) | 0.0649 (14) | −0.0235 (13) | 0.0191 (11) | −0.0180 (17) |
F2CB | 0.0422 (13) | 0.0632 (18) | 0.0680 (16) | 0.0179 (13) | 0.0017 (12) | −0.0168 (15) |
O1CB | 0.0414 (17) | 0.0303 (10) | 0.0809 (17) | −0.0108 (16) | 0.0130 (17) | −0.0017 (18) |
C1C | 0.0400 (17) | 0.0231 (19) | 0.0196 (13) | −0.0020 (14) | −0.0004 (12) | −0.0015 (13) |
C2C | 0.028 (2) | 0.0340 (15) | 0.0244 (14) | 0.0012 (16) | −0.0020 (14) | 0.0006 (12) |
C3C | 0.0444 (19) | 0.030 (2) | 0.0345 (17) | 0.0000 (17) | 0.0019 (15) | −0.0008 (16) |
C4C | 0.0306 (15) | 0.025 (2) | 0.0364 (16) | −0.0028 (14) | 0.0039 (12) | −0.0045 (15) |
C5C | 0.027 (2) | 0.0336 (14) | 0.0235 (13) | −0.0114 (15) | 0.0017 (13) | 0.0035 (11) |
C6C | 0.0295 (14) | 0.0172 (19) | 0.0290 (14) | −0.0061 (14) | −0.0007 (11) | −0.0018 (14) |
C1CD | 0.0400 (17) | 0.0231 (19) | 0.0196 (13) | −0.0020 (14) | −0.0004 (12) | −0.0015 (13) |
C2CD | 0.028 (2) | 0.0340 (15) | 0.0244 (14) | 0.0012 (16) | −0.0020 (14) | 0.0006 (12) |
C3CD | 0.0444 (19) | 0.030 (2) | 0.0345 (17) | 0.0000 (17) | 0.0019 (15) | −0.0008 (16) |
C4CD | 0.0306 (15) | 0.025 (2) | 0.0364 (16) | −0.0028 (14) | 0.0039 (12) | −0.0045 (15) |
C5CD | 0.027 (2) | 0.0336 (14) | 0.0235 (13) | −0.0114 (15) | 0.0017 (13) | 0.0035 (11) |
C6CD | 0.0295 (14) | 0.0172 (19) | 0.0290 (14) | −0.0061 (14) | −0.0007 (11) | −0.0018 (14) |
C9C | 0.0316 (10) | 0.0308 (10) | 0.0403 (12) | −0.0035 (15) | −0.0008 (9) | 0.0014 (16) |
C7CA | 0.0360 (17) | 0.0346 (16) | 0.0236 (15) | 0.0085 (13) | −0.0015 (13) | −0.0059 (14) |
C8CA | 0.0253 (16) | 0.040 (2) | 0.0391 (17) | 0.0028 (15) | 0.0026 (14) | −0.0049 (18) |
C10C | 0.0328 (16) | 0.0210 (16) | 0.0282 (15) | −0.0005 (13) | 0.0042 (13) | 0.0019 (14) |
C11C | 0.0266 (15) | 0.0231 (14) | 0.0283 (16) | 0.0018 (12) | −0.0021 (12) | −0.0070 (13) |
C7CB | 0.0360 (17) | 0.0346 (16) | 0.0236 (15) | 0.0085 (13) | −0.0015 (13) | −0.0059 (14) |
C8CB | 0.0253 (16) | 0.040 (2) | 0.0391 (17) | 0.0028 (15) | 0.0026 (14) | −0.0049 (18) |
C10D | 0.0328 (16) | 0.0210 (16) | 0.0282 (15) | −0.0005 (13) | 0.0042 (13) | 0.0019 (14) |
C11D | 0.0266 (15) | 0.0231 (14) | 0.0283 (16) | 0.0018 (12) | −0.0021 (12) | −0.0070 (13) |
C12C | 0.0214 (14) | 0.0251 (19) | 0.0214 (12) | −0.0034 (13) | −0.0077 (10) | 0.0012 (14) |
C13C | 0.0082 (14) | 0.0335 (16) | 0.0351 (16) | 0.0028 (14) | −0.0035 (14) | 0.0026 (13) |
C14C | 0.0238 (16) | 0.042 (2) | 0.0316 (16) | −0.0044 (15) | −0.0074 (13) | 0.0026 (16) |
C15C | 0.0240 (14) | 0.026 (2) | 0.0296 (15) | −0.0017 (14) | −0.0015 (12) | −0.0079 (15) |
C16C | 0.018 (2) | 0.0306 (15) | 0.0371 (16) | −0.0057 (15) | −0.0082 (15) | 0.0037 (12) |
C17C | 0.0299 (15) | 0.0127 (17) | 0.0299 (14) | 0.0041 (13) | −0.0044 (12) | 0.0005 (14) |
C12D | 0.0214 (14) | 0.0251 (19) | 0.0214 (12) | −0.0034 (13) | −0.0077 (10) | 0.0012 (14) |
C13D | 0.0082 (14) | 0.0335 (16) | 0.0351 (16) | 0.0028 (14) | −0.0035 (14) | 0.0026 (13) |
C14D | 0.0238 (16) | 0.042 (2) | 0.0316 (16) | −0.0044 (15) | −0.0074 (13) | 0.0026 (16) |
C15D | 0.0240 (14) | 0.026 (2) | 0.0296 (15) | −0.0017 (14) | −0.0015 (12) | −0.0079 (15) |
C16D | 0.018 (2) | 0.0306 (15) | 0.0371 (16) | −0.0057 (15) | −0.0082 (15) | 0.0037 (12) |
C17D | 0.0299 (15) | 0.0127 (17) | 0.0299 (14) | 0.0041 (13) | −0.0044 (12) | 0.0005 (14) |
F1A—C4A | 1.354 (3) | F1CA—C4C | 1.313 (3) |
F2A—C15A | 1.379 (3) | F2CA—C15C | 1.343 (3) |
O1A—C9A | 1.233 (4) | O1CA—C9C | 1.197 (4) |
C1A—C2A | 1.397 (4) | F1CB—C4CD | 1.348 (8) |
C1A—C6A | 1.397 (4) | F2CB—C15D | 1.356 (7) |
C1A—C7A | 1.482 (4) | O1CB—C9C | 1.331 (8) |
C2A—C3A | 1.360 (4) | C1C—C2C | 1.3900 |
C2A—H2AA | 0.9500 | C1C—C6C | 1.3900 |
C3A—C4A | 1.395 (4) | C1C—C7CA | 1.491 (4) |
C3A—H3AA | 0.9500 | C2C—C3C | 1.3900 |
C4A—C5A | 1.360 (4) | C2C—H2CA | 0.9500 |
C5A—C6A | 1.372 (4) | C3C—C4C | 1.3900 |
C5A—H5AA | 0.9500 | C3C—H3CA | 0.9500 |
C6A—H6AA | 0.9500 | C4C—C5C | 1.3900 |
C7A—C8A | 1.293 (4) | C5C—C6C | 1.3900 |
C7A—H7AA | 0.9500 | C5C—H5CA | 0.9500 |
C8A—C9A | 1.486 (4) | C6C—H6CA | 0.9500 |
C8A—H8AA | 0.9500 | C1CD—C2CD | 1.3900 |
C9A—C10A | 1.491 (4) | C1CD—C6CD | 1.3900 |
C10A—C11A | 1.309 (4) | C1CD—C7CB | 1.438 (10) |
C10A—H10A | 0.9500 | C2CD—C3CD | 1.3900 |
C11A—C12A | 1.473 (4) | C2CD—H2CB | 0.9500 |
C11A—H11A | 0.9500 | C3CD—C4CD | 1.3900 |
C12A—C17A | 1.399 (4) | C3CD—H3CB | 0.9500 |
C12A—C13A | 1.417 (4) | C4CD—C5CD | 1.3900 |
C13A—C14A | 1.399 (4) | C5CD—C6CD | 1.3900 |
C13A—H13A | 0.9500 | C5CD—H5CB | 0.9500 |
C14A—C15A | 1.376 (4) | C6CD—H6CB | 0.9500 |
C14A—H14A | 0.9500 | C9C—C10D | 1.437 (9) |
C15A—C16A | 1.356 (4) | C9C—C8CA | 1.449 (5) |
C16A—C17A | 1.389 (4) | C9C—C8CB | 1.462 (10) |
C16A—H16A | 0.9500 | C9C—C10C | 1.523 (5) |
C17A—H17A | 0.9500 | C7CA—C8CA | 1.331 (6) |
F1B—C4B | 1.342 (3) | C7CA—H7CA | 0.9500 |
F2B—C15B | 1.367 (3) | C8CA—H8CA | 0.9500 |
O1B—C9B | 1.220 (3) | C10C—C11C | 1.344 (5) |
C1B—C2B | 1.385 (4) | C10C—H10C | 0.9500 |
C1B—C6B | 1.389 (4) | C11C—C12C | 1.452 (4) |
C1B—C7B | 1.471 (4) | C11C—H11C | 0.9500 |
C2B—C3B | 1.363 (4) | C7CB—C8CB | 1.342 (12) |
C2B—H2BA | 0.9500 | C7CB—H7CB | 0.9500 |
C3B—C4B | 1.368 (4) | C8CB—H8CB | 0.9500 |
C3B—H3BA | 0.9500 | C10D—C11D | 1.327 (12) |
C4B—C5B | 1.385 (4) | C10D—H10D | 0.9500 |
C5B—C6B | 1.392 (4) | C11D—C12D | 1.479 (9) |
C5B—H5BA | 0.9500 | C11D—H11D | 0.9500 |
C6B—H6BA | 0.9500 | C12C—C13C | 1.3900 |
C7B—C8B | 1.338 (4) | C12C—C17C | 1.3900 |
C7B—H7BA | 0.9500 | C13C—C14C | 1.3900 |
C8B—C9B | 1.457 (3) | C13C—H13C | 0.9500 |
C8B—H8BA | 0.9500 | C14C—C15C | 1.3900 |
C9B—C10B | 1.485 (4) | C14C—H14C | 0.9500 |
C10B—C11B | 1.349 (4) | C15C—C16C | 1.3900 |
C10B—H10B | 0.9500 | C16C—C17C | 1.3900 |
C11B—C12B | 1.470 (4) | C16C—H16C | 0.9500 |
C11B—H11B | 0.9500 | C17C—H17C | 0.9500 |
C12B—C13B | 1.389 (4) | C12D—C13D | 1.3900 |
C12B—C17B | 1.404 (4) | C12D—C17D | 1.3900 |
C13B—C14B | 1.403 (4) | C13D—C14D | 1.3900 |
C13B—H13B | 0.9500 | C13D—H13D | 0.9500 |
C14B—C15B | 1.349 (4) | C14D—C15D | 1.3900 |
C14B—H14B | 0.9500 | C14D—H14D | 0.9500 |
C15B—C16B | 1.403 (4) | C15D—C16D | 1.3900 |
C16B—C17B | 1.392 (4) | C16D—C17D | 1.3900 |
C16B—H16B | 0.9500 | C16D—H16D | 0.9500 |
C17B—H17B | 0.9500 | C17D—H17D | 0.9500 |
C2A—C1A—C6A | 116.9 (2) | C1C—C2C—H2CA | 120.0 |
C2A—C1A—C7A | 119.2 (3) | C2C—C3C—C4C | 120.0 |
C6A—C1A—C7A | 123.9 (2) | C2C—C3C—H3CA | 120.0 |
C3A—C2A—C1A | 123.4 (3) | C4C—C3C—H3CA | 120.0 |
C3A—C2A—H2AA | 118.3 | F1CA—C4C—C3C | 119.7 (2) |
C1A—C2A—H2AA | 118.3 | F1CA—C4C—C5C | 120.3 (2) |
C2A—C3A—C4A | 117.0 (3) | C3C—C4C—C5C | 120.0 |
C2A—C3A—H3AA | 121.5 | C6C—C5C—C4C | 120.0 |
C4A—C3A—H3AA | 121.5 | C6C—C5C—H5CA | 120.0 |
F1A—C4A—C5A | 119.2 (3) | C4C—C5C—H5CA | 120.0 |
F1A—C4A—C3A | 118.7 (3) | C5C—C6C—C1C | 120.0 |
C5A—C4A—C3A | 122.0 (3) | C5C—C6C—H6CA | 120.0 |
C4A—C5A—C6A | 119.7 (3) | C1C—C6C—H6CA | 120.0 |
C4A—C5A—H5AA | 120.2 | C2CD—C1CD—C6CD | 120.0 |
C6A—C5A—H5AA | 120.2 | C2CD—C1CD—C7CB | 130.2 (4) |
C5A—C6A—C1A | 120.9 (2) | C6CD—C1CD—C7CB | 109.7 (4) |
C5A—C6A—H6AA | 119.6 | C3CD—C2CD—C1CD | 120.0 |
C1A—C6A—H6AA | 119.6 | C3CD—C2CD—H2CB | 120.0 |
C8A—C7A—C1A | 126.1 (3) | C1CD—C2CD—H2CB | 120.0 |
C8A—C7A—H7AA | 116.9 | C4CD—C3CD—C2CD | 120.0 |
C1A—C7A—H7AA | 116.9 | C4CD—C3CD—H3CB | 120.0 |
C7A—C8A—C9A | 118.9 (3) | C2CD—C3CD—H3CB | 120.0 |
C7A—C8A—H8AA | 120.6 | F1CB—C4CD—C3CD | 111.7 (5) |
C9A—C8A—H8AA | 120.6 | F1CB—C4CD—C5CD | 128.2 (5) |
O1A—C9A—C8A | 122.8 (3) | C3CD—C4CD—C5CD | 120.0 |
O1A—C9A—C10A | 117.8 (3) | C6CD—C5CD—C4CD | 120.0 |
C8A—C9A—C10A | 119.4 (2) | C6CD—C5CD—H5CB | 120.0 |
C11A—C10A—C9A | 126.5 (3) | C4CD—C5CD—H5CB | 120.0 |
C11A—C10A—H10A | 116.8 | C5CD—C6CD—C1CD | 120.0 |
C9A—C10A—H10A | 116.8 | C5CD—C6CD—H6CB | 120.0 |
C10A—C11A—C12A | 124.1 (3) | C1CD—C6CD—H6CB | 120.0 |
C10A—C11A—H11A | 118.0 | O1CA—C9C—O1CB | 32.6 (3) |
C12A—C11A—H11A | 118.0 | O1CA—C9C—C10D | 95.0 (4) |
C17A—C12A—C13A | 118.5 (2) | O1CB—C9C—C10D | 127.5 (5) |
C17A—C12A—C11A | 120.7 (2) | O1CA—C9C—C8CA | 117.7 (3) |
C13A—C12A—C11A | 120.8 (2) | O1CB—C9C—C8CA | 85.1 (4) |
C14A—C13A—C12A | 119.5 (2) | C10D—C9C—C8CA | 147.4 (4) |
C14A—C13A—H13A | 120.3 | O1CA—C9C—C8CB | 141.4 (5) |
C12A—C13A—H13A | 120.2 | O1CB—C9C—C8CB | 109.6 (6) |
C15A—C14A—C13A | 118.2 (3) | C10D—C9C—C8CB | 122.1 (6) |
C15A—C14A—H14A | 120.9 | C8CA—C9C—C8CB | 26.2 (4) |
C13A—C14A—H14A | 120.9 | O1CA—C9C—C10C | 123.9 (4) |
C16A—C15A—C14A | 124.7 (3) | O1CB—C9C—C10C | 155.5 (5) |
C16A—C15A—F2A | 117.9 (3) | C10D—C9C—C10C | 30.2 (4) |
C14A—C15A—F2A | 117.4 (3) | C8CA—C9C—C10C | 118.0 (3) |
C15A—C16A—C17A | 117.1 (3) | C8CB—C9C—C10C | 94.5 (4) |
C15A—C16A—H16A | 121.5 | C8CA—C7CA—C1C | 123.6 (3) |
C17A—C16A—H16A | 121.5 | C8CA—C7CA—H7CA | 118.2 |
C16A—C17A—C12A | 122.0 (2) | C1C—C7CA—H7CA | 118.2 |
C16A—C17A—H17A | 119.0 | C7CA—C8CA—C9C | 127.4 (4) |
C12A—C17A—H17A | 119.0 | C7CA—C8CA—H8CA | 116.3 |
C2B—C1B—C6B | 118.6 (2) | C9C—C8CA—H8CA | 116.3 |
C2B—C1B—C7B | 124.2 (2) | C11C—C10C—C9C | 117.4 (3) |
C6B—C1B—C7B | 117.2 (2) | C11C—C10C—H10C | 121.3 |
C3B—C2B—C1B | 122.1 (3) | C9C—C10C—H10C | 121.3 |
C3B—C2B—H2BA | 118.9 | C10C—C11C—C12C | 123.3 (3) |
C1B—C2B—H2BA | 119.0 | C10C—C11C—H11C | 118.3 |
C2B—C3B—C4B | 118.8 (3) | C12C—C11C—H11C | 118.3 |
C2B—C3B—H3BA | 120.6 | C8CB—C7CB—C1CD | 140.8 (9) |
C4B—C3B—H3BA | 120.6 | C8CB—C7CB—H7CB | 109.6 |
F1B—C4B—C3B | 119.0 (3) | C1CD—C7CB—H7CB | 109.6 |
F1B—C4B—C5B | 119.4 (3) | C7CB—C8CB—C9C | 128.7 (9) |
C3B—C4B—C5B | 121.5 (3) | C7CB—C8CB—H8CB | 115.7 |
C4B—C5B—C6B | 118.9 (3) | C9C—C8CB—H8CB | 115.7 |
C4B—C5B—H5BA | 120.5 | C11D—C10D—C9C | 123.5 (7) |
C6B—C5B—H5BA | 120.5 | C11D—C10D—H10D | 118.3 |
C1B—C6B—C5B | 120.0 (3) | C9C—C10D—H10D | 118.3 |
C1B—C6B—H6BA | 120.0 | C10D—C11D—C12D | 126.6 (7) |
C5B—C6B—H6BA | 120.0 | C10D—C11D—H11D | 116.7 |
C8B—C7B—C1B | 124.2 (2) | C12D—C11D—H11D | 116.7 |
C8B—C7B—H7BA | 117.9 | C13C—C12C—C17C | 120.0 |
C1B—C7B—H7BA | 117.9 | C13C—C12C—C11C | 114.99 (17) |
C7B—C8B—C9B | 128.6 (3) | C17C—C12C—C11C | 124.87 (17) |
C7B—C8B—H8BA | 115.7 | C12C—C13C—C14C | 120.0 |
C9B—C8B—H8BA | 115.7 | C12C—C13C—H13C | 120.0 |
O1B—C9B—C8B | 119.5 (2) | C14C—C13C—H13C | 120.0 |
O1B—C9B—C10B | 121.3 (2) | C15C—C14C—C13C | 120.0 |
C8B—C9B—C10B | 119.2 (2) | C15C—C14C—H14C | 120.0 |
C11B—C10B—C9B | 120.5 (2) | C13C—C14C—H14C | 120.0 |
C11B—C10B—H10B | 119.7 | F2CA—C15C—C16C | 118.8 (2) |
C9B—C10B—H10B | 119.7 | F2CA—C15C—C14C | 121.1 (2) |
C10B—C11B—C12B | 127.5 (2) | C16C—C15C—C14C | 120.0 |
C10B—C11B—H11B | 116.2 | C15C—C16C—C17C | 120.0 |
C12B—C11B—H11B | 116.2 | C15C—C16C—H16C | 120.0 |
C13B—C12B—C17B | 120.9 (2) | C17C—C16C—H16C | 120.0 |
C13B—C12B—C11B | 117.4 (2) | C16C—C17C—C12C | 120.0 |
C17B—C12B—C11B | 121.6 (2) | C16C—C17C—H17C | 120.0 |
C12B—C13B—C14B | 119.2 (3) | C12C—C17C—H17C | 120.0 |
C12B—C13B—H13B | 120.4 | C13D—C12D—C17D | 120.0 |
C14B—C13B—H13B | 120.4 | C13D—C12D—C11D | 111.5 (4) |
C15B—C14B—C13B | 118.8 (3) | C17D—C12D—C11D | 128.5 (4) |
C15B—C14B—H14B | 120.6 | C14D—C13D—C12D | 120.0 |
C13B—C14B—H14B | 120.6 | C14D—C13D—H13D | 120.0 |
C14B—C15B—F2B | 119.4 (3) | C12D—C13D—H13D | 120.0 |
C14B—C15B—C16B | 124.2 (3) | C13D—C14D—C15D | 120.0 |
F2B—C15B—C16B | 116.3 (3) | C13D—C14D—H14D | 120.0 |
C17B—C16B—C15B | 116.9 (3) | C15D—C14D—H14D | 120.0 |
C17B—C16B—H16B | 121.6 | F2CB—C15D—C14D | 129.0 (5) |
C15B—C16B—H16B | 121.6 | F2CB—C15D—C16D | 111.0 (5) |
C16B—C17B—C12B | 120.0 (2) | C14D—C15D—C16D | 120.0 |
C16B—C17B—H17B | 120.0 | C17D—C16D—C15D | 120.0 |
C12B—C17B—H17B | 120.0 | C17D—C16D—H16D | 120.0 |
C2C—C1C—C6C | 120.0 | C15D—C16D—H16D | 120.0 |
C2C—C1C—C7CA | 124.98 (18) | C16D—C17D—C12D | 120.0 |
C6C—C1C—C7CA | 114.90 (18) | C16D—C17D—H17D | 120.0 |
C3C—C2C—C1C | 120.0 | C12D—C17D—H17D | 120.0 |
C3C—C2C—H2CA | 120.0 | ||
C6A—C1A—C2A—C3A | 1.8 (4) | C3C—C4C—C5C—C6C | 0.0 |
C7A—C1A—C2A—C3A | −179.6 (3) | C4C—C5C—C6C—C1C | 0.0 |
C1A—C2A—C3A—C4A | −1.4 (4) | C2C—C1C—C6C—C5C | 0.0 |
C2A—C3A—C4A—F1A | −179.8 (2) | C7CA—C1C—C6C—C5C | 176.26 (19) |
C2A—C3A—C4A—C5A | −1.5 (4) | C6CD—C1CD—C2CD—C3CD | 0.0 |
F1A—C4A—C5A—C6A | −177.7 (2) | C7CB—C1CD—C2CD—C3CD | −175.4 (6) |
C3A—C4A—C5A—C6A | 4.0 (4) | C1CD—C2CD—C3CD—C4CD | 0.0 |
C4A—C5A—C6A—C1A | −3.7 (4) | C2CD—C3CD—C4CD—F1CB | −177.0 (6) |
C2A—C1A—C6A—C5A | 0.8 (4) | C2CD—C3CD—C4CD—C5CD | 0.0 |
C7A—C1A—C6A—C5A | −177.7 (2) | F1CB—C4CD—C5CD—C6CD | 176.5 (7) |
C2A—C1A—C7A—C8A | 160.4 (3) | C3CD—C4CD—C5CD—C6CD | 0.0 |
C6A—C1A—C7A—C8A | −21.0 (4) | C4CD—C5CD—C6CD—C1CD | 0.0 |
C1A—C7A—C8A—C9A | 179.3 (2) | C2CD—C1CD—C6CD—C5CD | 0.0 |
C7A—C8A—C9A—O1A | −8.8 (4) | C7CB—C1CD—C6CD—C5CD | 176.2 (5) |
C7A—C8A—C9A—C10A | 170.4 (3) | C2C—C1C—C7CA—C8CA | −22.0 (5) |
O1A—C9A—C10A—C11A | 166.4 (3) | C6C—C1C—C7CA—C8CA | 161.9 (3) |
C8A—C9A—C10A—C11A | −12.9 (4) | C1C—C7CA—C8CA—C9C | −177.2 (3) |
C9A—C10A—C11A—C12A | −179.3 (2) | O1CA—C9C—C8CA—C7CA | 170.8 (4) |
C10A—C11A—C12A—C17A | 162.1 (3) | O1CB—C9C—C8CA—C7CA | 171.6 (6) |
C10A—C11A—C12A—C13A | −18.7 (4) | C10D—C9C—C8CA—C7CA | −7.3 (12) |
C17A—C12A—C13A—C14A | −1.0 (4) | C8CB—C9C—C8CA—C7CA | 11.5 (9) |
C11A—C12A—C13A—C14A | 179.8 (2) | C10C—C9C—C8CA—C7CA | −17.0 (6) |
C12A—C13A—C14A—C15A | 1.2 (4) | O1CA—C9C—C10C—C11C | −14.9 (6) |
C13A—C14A—C15A—C16A | −1.1 (4) | O1CB—C9C—C10C—C11C | −27.6 (14) |
C13A—C14A—C15A—F2A | 179.8 (2) | C10D—C9C—C10C—C11C | 3.9 (7) |
C14A—C15A—C16A—C17A | 0.7 (4) | C8CA—C9C—C10C—C11C | 173.4 (4) |
F2A—C15A—C16A—C17A | 179.8 (2) | C8CB—C9C—C10C—C11C | 161.2 (5) |
C15A—C16A—C17A—C12A | −0.5 (4) | C9C—C10C—C11C—C12C | −178.9 (3) |
C13A—C12A—C17A—C16A | 0.7 (4) | C2CD—C1CD—C7CB—C8CB | 159.8 (10) |
C11A—C12A—C17A—C16A | 179.9 (2) | C6CD—C1CD—C7CB—C8CB | −15.9 (13) |
C6B—C1B—C2B—C3B | −0.2 (4) | C1CD—C7CB—C8CB—C9C | −174.4 (8) |
C7B—C1B—C2B—C3B | −179.3 (2) | O1CA—C9C—C8CB—C7CB | −24.8 (16) |
C1B—C2B—C3B—C4B | −0.4 (4) | O1CB—C9C—C8CB—C7CB | −15.8 (12) |
C2B—C3B—C4B—F1B | −179.2 (3) | C10D—C9C—C8CB—C7CB | 173.5 (9) |
C2B—C3B—C4B—C5B | 0.6 (4) | C8CA—C9C—C8CB—C7CB | 5.4 (6) |
F1B—C4B—C5B—C6B | 179.6 (3) | C10C—C9C—C8CB—C7CB | 160.3 (10) |
C3B—C4B—C5B—C6B | −0.2 (4) | O1CA—C9C—C10D—C11D | 169.9 (8) |
C2B—C1B—C6B—C5B | 0.6 (4) | O1CB—C9C—C10D—C11D | 169.7 (8) |
C7B—C1B—C6B—C5B | 179.8 (2) | C8CA—C9C—C10D—C11D | −11.8 (15) |
C4B—C5B—C6B—C1B | −0.5 (4) | C8CB—C9C—C10D—C11D | −21.4 (11) |
C2B—C1B—C7B—C8B | −18.2 (4) | C10C—C9C—C10D—C11D | 5.5 (5) |
C6B—C1B—C7B—C8B | 162.7 (3) | C9C—C10D—C11D—C12D | −173.8 (6) |
C1B—C7B—C8B—C9B | −178.7 (2) | C10C—C11C—C12C—C13C | 163.8 (3) |
C7B—C8B—C9B—O1B | 169.0 (3) | C10C—C11C—C12C—C17C | −20.5 (4) |
C7B—C8B—C9B—C10B | −12.9 (4) | C17C—C12C—C13C—C14C | 0.0 |
O1B—C9B—C10B—C11B | −10.4 (4) | C11C—C12C—C13C—C14C | 175.9 (2) |
C8B—C9B—C10B—C11B | 171.5 (2) | C12C—C13C—C14C—C15C | 0.0 |
C9B—C10B—C11B—C12B | 179.5 (2) | C13C—C14C—C15C—F2CA | 176.7 (3) |
C10B—C11B—C12B—C13B | 158.1 (3) | C13C—C14C—C15C—C16C | 0.0 |
C10B—C11B—C12B—C17B | −21.8 (4) | F2CA—C15C—C16C—C17C | −176.7 (3) |
C17B—C12B—C13B—C14B | −0.3 (4) | C14C—C15C—C16C—C17C | 0.0 |
C11B—C12B—C13B—C14B | 179.8 (2) | C15C—C16C—C17C—C12C | 0.0 |
C12B—C13B—C14B—C15B | −0.6 (4) | C13C—C12C—C17C—C16C | 0.0 |
C13B—C14B—C15B—F2B | 179.4 (2) | C11C—C12C—C17C—C16C | −175.4 (2) |
C13B—C14B—C15B—C16B | 1.6 (5) | C10D—C11D—C12D—C13D | −23.1 (10) |
C14B—C15B—C16B—C17B | −1.7 (5) | C10D—C11D—C12D—C17D | 158.8 (7) |
F2B—C15B—C16B—C17B | −179.6 (2) | C17D—C12D—C13D—C14D | 0.0 |
C15B—C16B—C17B—C12B | 0.8 (4) | C11D—C12D—C13D—C14D | −178.3 (4) |
C13B—C12B—C17B—C16B | 0.1 (4) | C12D—C13D—C14D—C15D | 0.0 |
C11B—C12B—C17B—C16B | −180.0 (3) | C13D—C14D—C15D—F2CB | 179.2 (7) |
C6C—C1C—C2C—C3C | 0.0 | C13D—C14D—C15D—C16D | 0.0 |
C7CA—C1C—C2C—C3C | −175.9 (2) | F2CB—C15D—C16D—C17D | −179.3 (5) |
C1C—C2C—C3C—C4C | 0.0 | C14D—C15D—C16D—C17D | 0.0 |
C2C—C3C—C4C—F1CA | 178.6 (3) | C15D—C16D—C17D—C12D | 0.0 |
C2C—C3C—C4C—C5C | 0.0 | C13D—C12D—C17D—C16D | 0.0 |
F1CA—C4C—C5C—C6C | −178.6 (3) | C11D—C12D—C17D—C16D | 178.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7CA—H7CA···O1CBi | 0.95 | 2.38 | 3.260 (8) | 153 |
C11D—H11D···O1CAi | 0.95 | 2.50 | 3.379 (9) | 154 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H12F2O |
Mr | 270.27 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 173 |
a, b, c (Å) | 90.019 (14), 5.8228 (9), 7.5301 (12) |
β (°) | 90.868 (4) |
V (Å3) | 3946.5 (11) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5194, 5194, 3837 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.683 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.094, 0.275, 1.06 |
No. of reflections | 5194 |
No. of parameters | 541 |
No. of restraints | 50 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.33 |
Absolute structure | Flack (1983), 4789 Friedel pairs |
Absolute structure parameter | 0.0 (13) |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2006), SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C7CA—H7CA···O1CBi | 0.95 | 2.38 | 3.260 (8) | 153.2 |
C11D—H11D···O1CAi | 0.95 | 2.50 | 3.379 (9) | 154.2 |
Symmetry code: (i) x, y+1, z. |
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).