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
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).