




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107049426/av3115sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270107049426/av3115Isup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270107049426/av3115IIsup3.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270107049426/av3115IIIsup4.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270107049426/av3115IVsup5.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270107049426/av3115Vsup6.hkl |
CCDC references: 265771; 265772; 265773; 265774; 265775
To a thoroughly stirred solution of substituted acetophenone (0.01 mol) and 4-fluoro-3-phenoxybezaldehyde (0.01 mol) in methanol (25 ml), 40% aqueous NaOH solution (100 ml) was added at room temperature; the mixture was heated for 10 min and left overnight. It was then poured into ice–water and the precipitated product was filtered off. The crude product was recrystallized from hexane. The synthesized product was characterized by melting point meaurements, and IR, NMR and mass spectroscopy (Mohan, 2006). This was again taken in 5.0 ml beakers and a series of crystallization experiments were performed in solvents such as acetone, ethylacetate/hexane, dichloromethane and dichloromethane/hexane. In all the cases, the crystals on which the final data were collected were grown from acetone.
In all the five compounds, H atoms were located from difference Fourier maps and refined isotropically. The C—H bond lengths are in the range 0.87 (2)–1.05 (2) Å.
For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
C21H15FO2 | F(000) = 664 |
Mr = 318.33 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 835 reflections |
a = 7.2869 (17) Å | θ = 1.4–25.2° |
b = 5.9407 (14) Å | µ = 0.09 mm−1 |
c = 36.805 (8) Å | T = 290 K |
β = 93.724 (4)° | Block, colorless |
V = 1589.9 (6) Å3 | 0.56 × 0.40 × 0.24 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 3220 independent reflections |
Radiation source: fine-focus sealed tube | 2748 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.929, Tmax = 0.978 | k = −7→7 |
11668 measured reflections | l = −45→45 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | All H-atom parameters refined |
S = 1.21 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.4268P] where P = (Fo2 + 2Fc2)/3 |
3220 reflections | (Δ/σ)max < 0.001 |
277 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C21H15FO2 | V = 1589.9 (6) Å3 |
Mr = 318.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2869 (17) Å | µ = 0.09 mm−1 |
b = 5.9407 (14) Å | T = 290 K |
c = 36.805 (8) Å | 0.56 × 0.40 × 0.24 mm |
β = 93.724 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 3220 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2748 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.978 | Rint = 0.017 |
11668 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.135 | All H-atom parameters refined |
S = 1.21 | Δρmax = 0.18 e Å−3 |
3220 reflections | Δρmin = −0.15 e Å−3 |
277 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.5142 (2) | 0.3032 (2) | 0.17115 (4) | 0.0808 (4) | |
O1 | 0.2403 (2) | 1.1937 (2) | 0.00204 (4) | 0.0726 (5) | |
O2 | 0.37504 (19) | 0.7175 (3) | 0.18472 (4) | 0.0664 (4) | |
C1 | 0.0876 (3) | 0.8622 (4) | −0.11942 (5) | 0.0579 (5) | |
C2 | 0.1639 (3) | 1.0661 (4) | −0.10864 (5) | 0.0550 (5) | |
C3 | 0.2107 (2) | 1.1061 (3) | −0.07233 (5) | 0.0477 (4) | |
C4 | 0.1862 (2) | 0.9405 (3) | −0.04632 (5) | 0.0421 (4) | |
C5 | 0.1111 (2) | 0.7340 (3) | −0.05747 (5) | 0.0487 (4) | |
C6 | 0.0597 (3) | 0.6971 (4) | −0.09407 (6) | 0.0553 (5) | |
C7 | 0.2336 (2) | 0.9963 (3) | −0.00741 (5) | 0.0485 (4) | |
C8 | 0.2748 (3) | 0.8134 (3) | 0.01898 (5) | 0.0506 (4) | |
C9 | 0.2815 (2) | 0.8544 (3) | 0.05447 (5) | 0.0459 (4) | |
C10 | 0.3345 (2) | 0.7006 (3) | 0.08427 (5) | 0.0427 (4) | |
C11 | 0.3215 (2) | 0.7736 (3) | 0.12008 (5) | 0.0469 (4) | |
C12 | 0.3792 (2) | 0.6407 (3) | 0.14930 (5) | 0.0500 (4) | |
C13 | 0.4539 (2) | 0.4327 (3) | 0.14262 (5) | 0.0532 (5) | |
C14 | 0.4684 (3) | 0.3549 (3) | 0.10764 (6) | 0.0541 (5) | |
C15 | 0.4082 (2) | 0.4873 (3) | 0.07860 (5) | 0.0475 (4) | |
C16 | 0.2028 (3) | 0.7760 (3) | 0.19599 (4) | 0.0509 (4) | |
C17 | 0.1899 (3) | 0.9730 (4) | 0.21513 (6) | 0.0633 (5) | |
C18 | 0.0221 (4) | 1.0323 (5) | 0.22768 (6) | 0.0789 (7) | |
C19 | −0.1291 (4) | 0.8977 (6) | 0.22112 (6) | 0.0851 (8) | |
C20 | −0.1133 (4) | 0.7002 (5) | 0.20257 (6) | 0.0788 (7) | |
C21 | 0.0536 (3) | 0.6372 (4) | 0.18984 (6) | 0.0648 (6) | |
H1 | 0.050 (3) | 0.835 (4) | −0.1459 (6) | 0.066 (6)* | |
H2 | 0.184 (3) | 1.181 (4) | −0.1271 (6) | 0.068 (6)* | |
H3 | 0.261 (3) | 1.250 (3) | −0.0643 (5) | 0.048 (5)* | |
H5 | 0.092 (3) | 0.619 (3) | −0.0396 (5) | 0.054 (5)* | |
H6 | 0.008 (3) | 0.553 (4) | −0.1015 (5) | 0.062 (6)* | |
H8 | 0.303 (3) | 0.668 (4) | 0.0102 (6) | 0.065 (6)* | |
H9 | 0.251 (3) | 1.006 (4) | 0.0623 (5) | 0.057 (5)* | |
H11 | 0.268 (3) | 0.920 (4) | 0.1250 (5) | 0.057 (5)* | |
H14 | 0.519 (3) | 0.209 (4) | 0.1053 (6) | 0.070 (6)* | |
H15 | 0.420 (2) | 0.432 (3) | 0.0544 (5) | 0.051 (5)* | |
H17 | 0.297 (3) | 1.060 (4) | 0.2181 (6) | 0.072 (7)* | |
H18 | 0.013 (4) | 1.172 (5) | 0.2407 (8) | 0.100 (9)* | |
H19 | −0.247 (4) | 0.942 (5) | 0.2300 (8) | 0.104 (9)* | |
H20 | −0.214 (4) | 0.600 (5) | 0.1984 (7) | 0.099 (9)* | |
H21 | 0.070 (3) | 0.499 (4) | 0.1772 (6) | 0.077 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0874 (9) | 0.0802 (9) | 0.0730 (8) | 0.0148 (7) | −0.0078 (7) | 0.0232 (7) |
O1 | 0.1163 (13) | 0.0475 (8) | 0.0537 (8) | −0.0015 (8) | 0.0031 (8) | −0.0081 (6) |
O2 | 0.0587 (8) | 0.0946 (11) | 0.0448 (7) | 0.0081 (8) | −0.0050 (6) | −0.0080 (7) |
C1 | 0.0575 (11) | 0.0670 (13) | 0.0481 (11) | 0.0118 (9) | −0.0052 (9) | −0.0062 (9) |
C2 | 0.0599 (11) | 0.0561 (11) | 0.0490 (10) | 0.0092 (9) | 0.0037 (9) | 0.0079 (9) |
C3 | 0.0473 (9) | 0.0427 (10) | 0.0533 (10) | 0.0030 (8) | 0.0046 (8) | 0.0003 (8) |
C4 | 0.0393 (8) | 0.0428 (9) | 0.0446 (9) | 0.0050 (7) | 0.0062 (7) | −0.0013 (7) |
C5 | 0.0490 (10) | 0.0443 (10) | 0.0537 (10) | 0.0009 (8) | 0.0095 (8) | −0.0006 (8) |
C6 | 0.0519 (10) | 0.0527 (11) | 0.0606 (12) | −0.0004 (9) | −0.0014 (8) | −0.0123 (9) |
C7 | 0.0530 (10) | 0.0468 (10) | 0.0463 (10) | 0.0018 (8) | 0.0082 (8) | −0.0047 (8) |
C8 | 0.0572 (11) | 0.0476 (10) | 0.0474 (10) | 0.0059 (8) | 0.0061 (8) | −0.0044 (8) |
C9 | 0.0455 (9) | 0.0449 (10) | 0.0477 (10) | 0.0025 (7) | 0.0050 (7) | −0.0038 (8) |
C10 | 0.0347 (8) | 0.0465 (9) | 0.0472 (9) | 0.0000 (7) | 0.0041 (7) | −0.0032 (7) |
C11 | 0.0444 (9) | 0.0486 (10) | 0.0475 (10) | 0.0059 (8) | 0.0030 (7) | −0.0046 (8) |
C12 | 0.0428 (9) | 0.0615 (11) | 0.0452 (9) | 0.0010 (8) | 0.0005 (7) | −0.0027 (8) |
C13 | 0.0454 (10) | 0.0565 (11) | 0.0570 (11) | 0.0027 (8) | −0.0020 (8) | 0.0107 (9) |
C14 | 0.0473 (10) | 0.0447 (10) | 0.0700 (13) | 0.0057 (8) | 0.0031 (9) | −0.0014 (9) |
C15 | 0.0431 (9) | 0.0489 (10) | 0.0511 (10) | 0.0021 (7) | 0.0067 (7) | −0.0069 (8) |
C16 | 0.0596 (11) | 0.0613 (11) | 0.0315 (8) | −0.0008 (9) | −0.0003 (7) | 0.0027 (8) |
C17 | 0.0725 (14) | 0.0676 (14) | 0.0495 (11) | −0.0092 (11) | 0.0005 (10) | −0.0041 (10) |
C18 | 0.0943 (19) | 0.0838 (17) | 0.0595 (13) | 0.0086 (14) | 0.0126 (12) | −0.0190 (12) |
C19 | 0.0713 (15) | 0.130 (2) | 0.0550 (13) | 0.0028 (16) | 0.0157 (11) | −0.0117 (15) |
C20 | 0.0726 (15) | 0.113 (2) | 0.0520 (12) | −0.0283 (15) | 0.0099 (11) | −0.0017 (13) |
C21 | 0.0798 (14) | 0.0675 (14) | 0.0473 (11) | −0.0151 (11) | 0.0047 (10) | −0.0048 (10) |
C5—C6 | 1.392 (3) | C11—H11 | 0.97 (2) |
C5—C4 | 1.394 (3) | C14—C13 | 1.378 (3) |
C5—H5 | 0.97 (2) | C14—H14 | 0.95 (2) |
C10—C11 | 1.397 (2) | C16—C21 | 1.371 (3) |
C10—C15 | 1.397 (2) | C16—C17 | 1.372 (3) |
C10—C9 | 1.460 (2) | C2—C1 | 1.380 (3) |
F1—C13 | 1.352 (2) | C2—H2 | 0.98 (2) |
C3—C2 | 1.378 (3) | C1—C6 | 1.378 (3) |
C3—C4 | 1.392 (2) | C1—H1 | 1.01 (2) |
C3—H3 | 0.968 (19) | C12—C13 | 1.378 (3) |
C9—C8 | 1.327 (3) | C6—H6 | 0.97 (2) |
C9—H9 | 0.97 (2) | C17—C18 | 1.381 (3) |
O1—C7 | 1.224 (2) | C17—H17 | 0.94 (2) |
O2—C12 | 1.384 (2) | C21—C20 | 1.383 (3) |
O2—C16 | 1.392 (2) | C21—H21 | 0.96 (3) |
C15—C14 | 1.376 (3) | C20—C19 | 1.366 (4) |
C15—H15 | 0.958 (19) | C20—H20 | 0.95 (3) |
C8—C7 | 1.475 (3) | C18—C19 | 1.370 (4) |
C8—H8 | 0.95 (2) | C18—H18 | 0.96 (3) |
C4—C7 | 1.489 (2) | C19—H19 | 0.98 (3) |
C11—C12 | 1.378 (3) | ||
C6—C5—C4 | 119.93 (18) | C21—C16—O2 | 121.43 (19) |
C6—C5—H5 | 120.5 (12) | C17—C16—O2 | 117.30 (19) |
C4—C5—H5 | 119.5 (12) | C3—C2—C1 | 119.99 (19) |
C11—C10—C15 | 118.22 (17) | C3—C2—H2 | 120.9 (13) |
C11—C10—C9 | 118.92 (16) | C1—C2—H2 | 119.1 (13) |
C15—C10—C9 | 122.75 (16) | C6—C1—C2 | 120.29 (19) |
C2—C3—C4 | 120.66 (18) | C6—C1—H1 | 119.8 (13) |
C2—C3—H3 | 120.9 (11) | C2—C1—H1 | 119.9 (13) |
C4—C3—H3 | 118.5 (11) | C11—C12—C13 | 118.59 (17) |
C8—C9—C10 | 128.00 (18) | C11—C12—O2 | 121.46 (18) |
C8—C9—H9 | 117.8 (12) | C13—C12—O2 | 119.80 (17) |
C10—C9—H9 | 114.2 (12) | F1—C13—C12 | 118.91 (18) |
C12—O2—C16 | 116.03 (14) | F1—C13—C14 | 119.59 (18) |
C14—C15—C10 | 120.59 (18) | C12—C13—C14 | 121.50 (17) |
C14—C15—H15 | 118.7 (11) | C1—C6—C5 | 120.09 (19) |
C10—C15—H15 | 120.7 (11) | C1—C6—H6 | 120.7 (12) |
C9—C8—C7 | 120.39 (18) | C5—C6—H6 | 119.2 (12) |
C9—C8—H8 | 120.5 (13) | C16—C17—C18 | 118.7 (2) |
C7—C8—H8 | 119.1 (13) | C16—C17—H17 | 116.4 (14) |
C3—C4—C5 | 119.00 (17) | C18—C17—H17 | 124.9 (14) |
C3—C4—C7 | 118.17 (16) | C16—C21—C20 | 119.1 (2) |
C5—C4—C7 | 122.76 (16) | C16—C21—H21 | 118.4 (14) |
C12—C11—C10 | 121.49 (17) | C20—C21—H21 | 122.5 (14) |
C12—C11—H11 | 118.2 (12) | C19—C20—C21 | 120.4 (2) |
C10—C11—H11 | 120.2 (12) | C19—C20—H20 | 122.1 (17) |
O1—C7—C8 | 121.10 (17) | C21—C20—H20 | 117.4 (17) |
O1—C7—C4 | 119.27 (17) | C19—C18—C17 | 120.8 (2) |
C8—C7—C4 | 119.62 (16) | C19—C18—H18 | 120.6 (17) |
C15—C14—C13 | 119.58 (18) | C17—C18—H18 | 118.6 (17) |
C15—C14—H14 | 124.0 (14) | C20—C19—C18 | 119.7 (2) |
C13—C14—H14 | 116.5 (14) | C20—C19—H19 | 120.3 (18) |
C21—C16—C17 | 121.2 (2) | C18—C19—H19 | 119.9 (17) |
C11—C10—C9—C8 | −176.10 (18) | C3—C2—C1—C6 | −0.7 (3) |
C15—C10—C9—C8 | 7.7 (3) | C10—C11—C12—C13 | 1.0 (3) |
C11—C10—C15—C14 | −0.9 (3) | C10—C11—C12—O2 | 176.63 (16) |
C9—C10—C15—C14 | 175.26 (16) | C16—O2—C12—C11 | 60.7 (2) |
C10—C9—C8—C7 | −174.49 (17) | C16—O2—C12—C13 | −123.75 (19) |
C2—C3—C4—C5 | −0.9 (3) | C11—C12—C13—F1 | 178.75 (16) |
C2—C3—C4—C7 | −178.07 (16) | O2—C12—C13—F1 | 3.0 (3) |
C6—C5—C4—C3 | −0.9 (3) | C11—C12—C13—C14 | −1.2 (3) |
C6—C5—C4—C7 | 176.23 (16) | O2—C12—C13—C14 | −176.93 (17) |
C15—C10—C11—C12 | 0.1 (3) | C15—C14—C13—F1 | −179.60 (16) |
C9—C10—C11—C12 | −176.28 (16) | C15—C14—C13—C12 | 0.4 (3) |
C9—C8—C7—O1 | 14.4 (3) | C2—C1—C6—C5 | −1.0 (3) |
C9—C8—C7—C4 | −166.65 (16) | C4—C5—C6—C1 | 1.8 (3) |
C3—C4—C7—O1 | 21.1 (3) | C21—C16—C17—C18 | −1.2 (3) |
C5—C4—C7—O1 | −156.02 (19) | O2—C16—C17—C18 | −178.01 (19) |
C3—C4—C7—C8 | −157.94 (16) | C17—C16—C21—C20 | 1.3 (3) |
C5—C4—C7—C8 | 25.0 (2) | O2—C16—C21—C20 | 178.05 (19) |
C10—C15—C14—C13 | 0.7 (3) | C16—C21—C20—C19 | −0.2 (4) |
C12—O2—C16—C21 | 47.6 (3) | C16—C17—C18—C19 | −0.2 (4) |
C12—O2—C16—C17 | −135.57 (19) | C21—C20—C19—C18 | −1.1 (4) |
C4—C3—C2—C1 | 1.6 (3) | C17—C18—C19—C20 | 1.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cg1i | 0.97 (3) | 3.02 (2) | 3.685 (2) | 127 (2) |
C14—H14···Cg2ii | 0.95 (2) | 2.77 (2) | 3.429 (2) | 128 (2) |
Symmetry codes: (i) −x+1/2, y+3/2, −z+1/2; (ii) −x+3/2, y+3/2, −z+1/2. |
C21H14F2O2 | Z = 2 |
Mr = 336.32 | F(000) = 348 |
Triclinic, P1 | Dx = 1.351 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.164 (5) Å | Cell parameters from 775 reflections |
b = 10.036 (6) Å | θ = 1.4–25.2° |
c = 11.136 (7) Å | µ = 0.10 mm−1 |
α = 97.362 (10)° | T = 290 K |
β = 101.898 (9)° | Plate, colorless |
γ = 108.731 (9)° | 0.23 × 0.20 × 0.06 mm |
V = 826.8 (9) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3291 independent reflections |
Radiation source: fine-focus sealed tube | 2205 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.944, Tmax = 0.994 | k = −12→12 |
8638 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0622P)2 + 0.0408P] where P = (Fo2 + 2Fc2)/3 |
3291 reflections | (Δ/σ)max < 0.001 |
282 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C21H14F2O2 | γ = 108.731 (9)° |
Mr = 336.32 | V = 826.8 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.164 (5) Å | Mo Kα radiation |
b = 10.036 (6) Å | µ = 0.10 mm−1 |
c = 11.136 (7) Å | T = 290 K |
α = 97.362 (10)° | 0.23 × 0.20 × 0.06 mm |
β = 101.898 (9)° |
Bruker SMART APEX CCD area-detector diffractometer | 3291 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2205 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.994 | Rint = 0.017 |
8638 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.118 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.12 e Å−3 |
3291 reflections | Δρmin = −0.19 e Å−3 |
282 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.37217 (15) | 0.54948 (11) | 0.68943 (10) | 0.0887 (4) | |
F2 | 0.83443 (16) | −0.04147 (15) | 1.56720 (12) | 0.1073 (4) | |
O1 | 0.21063 (19) | −0.08620 (17) | 1.11312 (13) | 0.1068 (5) | |
O2 | 0.03588 (16) | 0.36217 (12) | 0.67485 (11) | 0.0756 (4) | |
C1 | 0.7219 (3) | −0.0300 (2) | 1.46365 (17) | 0.0717 (5) | |
C2 | 0.5551 (3) | −0.1331 (2) | 1.41942 (18) | 0.0711 (5) | |
C3 | 0.4404 (3) | −0.11863 (18) | 1.31695 (16) | 0.0647 (4) | |
C4 | 0.4925 (2) | −0.00337 (15) | 1.25774 (13) | 0.0537 (4) | |
C5 | 0.6633 (2) | 0.09816 (18) | 1.30612 (16) | 0.0629 (4) | |
C6 | 0.7799 (3) | 0.0859 (2) | 1.41007 (18) | 0.0737 (5) | |
C7 | 0.3617 (2) | 0.00398 (18) | 1.14640 (15) | 0.0631 (4) | |
C8 | 0.4118 (2) | 0.11838 (18) | 1.07501 (15) | 0.0595 (4) | |
C9 | 0.2936 (2) | 0.13165 (18) | 0.98114 (15) | 0.0620 (4) | |
C10 | 0.3201 (2) | 0.23957 (16) | 0.90318 (14) | 0.0557 (4) | |
C11 | 0.1693 (2) | 0.25153 (18) | 0.82563 (15) | 0.0615 (4) | |
C12 | 0.1868 (2) | 0.35544 (17) | 0.75469 (14) | 0.0615 (4) | |
C13 | 0.3558 (2) | 0.44685 (17) | 0.75926 (15) | 0.0634 (4) | |
C14 | 0.5068 (2) | 0.43697 (19) | 0.83293 (16) | 0.0642 (4) | |
C15 | 0.4880 (2) | 0.33308 (17) | 0.90426 (15) | 0.0592 (4) | |
C16 | −0.0158 (2) | 0.47810 (16) | 0.70489 (15) | 0.0606 (4) | |
C17 | 0.0394 (2) | 0.5635 (2) | 0.82288 (19) | 0.0729 (5) | |
C18 | −0.0181 (3) | 0.6791 (2) | 0.8418 (3) | 0.0882 (6) | |
C19 | −0.1305 (3) | 0.7051 (3) | 0.7448 (3) | 0.0926 (7) | |
C20 | −0.1876 (3) | 0.6162 (3) | 0.6296 (2) | 0.0905 (7) | |
C21 | −0.1322 (2) | 0.5024 (2) | 0.6085 (2) | 0.0732 (5) | |
H2 | 0.517 (2) | −0.2113 (19) | 1.4593 (17) | 0.079 (5)* | |
H3 | 0.323 (3) | −0.187 (2) | 1.2838 (17) | 0.081 (6)* | |
H5 | 0.706 (2) | 0.1796 (18) | 1.2666 (15) | 0.070 (5)* | |
H6 | 0.895 (3) | 0.154 (2) | 1.4414 (18) | 0.089 (6)* | |
H8 | 0.531 (3) | 0.1797 (19) | 1.0988 (16) | 0.078 (5)* | |
H9 | 0.175 (3) | 0.0639 (19) | 0.9656 (17) | 0.084 (6)* | |
H11 | 0.053 (2) | 0.1887 (17) | 0.8247 (14) | 0.063 (4)* | |
H14 | 0.621 (3) | 0.4998 (19) | 0.8320 (16) | 0.076 (5)* | |
H15 | 0.592 (2) | 0.3252 (16) | 0.9564 (15) | 0.063 (4)* | |
H17 | 0.112 (2) | 0.5395 (18) | 0.8877 (17) | 0.072 (5)* | |
H18 | 0.022 (3) | 0.731 (2) | 0.921 (2) | 0.093 (7)* | |
H19 | −0.168 (3) | 0.786 (2) | 0.7597 (19) | 0.103 (7)* | |
H20 | −0.273 (3) | 0.634 (2) | 0.558 (2) | 0.114 (7)* | |
H21 | −0.168 (3) | 0.442 (2) | 0.529 (2) | 0.089 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0936 (8) | 0.0794 (7) | 0.0896 (7) | 0.0256 (6) | 0.0132 (6) | 0.0376 (6) |
F2 | 0.0981 (9) | 0.1437 (10) | 0.1014 (9) | 0.0654 (8) | 0.0143 (7) | 0.0608 (8) |
O1 | 0.0707 (9) | 0.1173 (11) | 0.0876 (10) | −0.0166 (8) | −0.0064 (7) | 0.0431 (8) |
O2 | 0.0735 (8) | 0.0682 (7) | 0.0690 (7) | 0.0288 (6) | −0.0133 (6) | 0.0026 (6) |
C1 | 0.0735 (12) | 0.0908 (13) | 0.0690 (11) | 0.0482 (11) | 0.0184 (9) | 0.0305 (10) |
C2 | 0.0871 (14) | 0.0675 (11) | 0.0747 (12) | 0.0364 (10) | 0.0322 (10) | 0.0297 (9) |
C3 | 0.0702 (12) | 0.0575 (10) | 0.0648 (10) | 0.0188 (9) | 0.0210 (9) | 0.0123 (8) |
C4 | 0.0568 (9) | 0.0538 (8) | 0.0530 (8) | 0.0206 (7) | 0.0186 (7) | 0.0113 (7) |
C5 | 0.0570 (10) | 0.0652 (10) | 0.0684 (10) | 0.0212 (8) | 0.0160 (8) | 0.0236 (8) |
C6 | 0.0564 (11) | 0.0832 (12) | 0.0794 (12) | 0.0243 (10) | 0.0098 (9) | 0.0251 (10) |
C7 | 0.0569 (10) | 0.0669 (10) | 0.0565 (9) | 0.0115 (8) | 0.0137 (8) | 0.0114 (8) |
C8 | 0.0535 (10) | 0.0631 (9) | 0.0564 (9) | 0.0165 (8) | 0.0103 (8) | 0.0121 (7) |
C9 | 0.0522 (10) | 0.0679 (10) | 0.0599 (10) | 0.0163 (8) | 0.0114 (8) | 0.0120 (8) |
C10 | 0.0543 (9) | 0.0587 (9) | 0.0501 (8) | 0.0200 (7) | 0.0084 (7) | 0.0062 (7) |
C11 | 0.0516 (10) | 0.0629 (10) | 0.0605 (10) | 0.0157 (8) | 0.0051 (8) | 0.0081 (8) |
C12 | 0.0613 (10) | 0.0599 (9) | 0.0545 (9) | 0.0230 (8) | −0.0012 (7) | 0.0050 (7) |
C13 | 0.0711 (11) | 0.0580 (9) | 0.0585 (9) | 0.0225 (8) | 0.0114 (8) | 0.0134 (8) |
C14 | 0.0591 (10) | 0.0632 (10) | 0.0652 (10) | 0.0162 (8) | 0.0151 (8) | 0.0130 (8) |
C15 | 0.0511 (9) | 0.0671 (10) | 0.0559 (9) | 0.0221 (8) | 0.0082 (7) | 0.0077 (8) |
C16 | 0.0529 (9) | 0.0578 (9) | 0.0665 (10) | 0.0144 (7) | 0.0112 (8) | 0.0186 (8) |
C17 | 0.0587 (11) | 0.0733 (11) | 0.0759 (13) | 0.0171 (9) | 0.0095 (9) | 0.0087 (10) |
C18 | 0.0737 (13) | 0.0807 (14) | 0.0995 (17) | 0.0138 (11) | 0.0338 (13) | 0.0002 (13) |
C19 | 0.0917 (16) | 0.0851 (15) | 0.129 (2) | 0.0449 (13) | 0.0563 (16) | 0.0413 (15) |
C20 | 0.0977 (16) | 0.1119 (17) | 0.0970 (16) | 0.0606 (14) | 0.0436 (13) | 0.0528 (15) |
C21 | 0.0716 (12) | 0.0881 (13) | 0.0709 (12) | 0.0356 (10) | 0.0208 (10) | 0.0332 (11) |
C10—C15 | 1.387 (2) | C3—H3 | 0.944 (19) |
C10—C11 | 1.400 (2) | C7—O1 | 1.219 (2) |
C10—C9 | 1.463 (2) | C6—C1 | 1.369 (3) |
F1—C13 | 1.3576 (19) | C6—C5 | 1.385 (2) |
O2—C16 | 1.385 (2) | C6—H6 | 0.93 (2) |
O2—C12 | 1.3895 (19) | C15—H15 | 0.959 (16) |
C11—C12 | 1.376 (2) | C5—H5 | 0.978 (17) |
C11—H11 | 0.953 (17) | C16—C17 | 1.373 (3) |
C14—C13 | 1.373 (2) | C16—C21 | 1.382 (2) |
C14—C15 | 1.379 (2) | C1—C2 | 1.362 (3) |
C14—H14 | 0.947 (19) | C2—H2 | 0.949 (18) |
C9—C8 | 1.321 (2) | C21—C20 | 1.368 (3) |
C9—H9 | 0.955 (19) | C21—H21 | 0.94 (2) |
C12—C13 | 1.376 (2) | C17—C18 | 1.392 (3) |
C4—C5 | 1.382 (2) | C17—H17 | 0.946 (18) |
C4—C3 | 1.396 (2) | C18—C19 | 1.376 (3) |
C4—C7 | 1.487 (2) | C18—H18 | 0.90 (2) |
C8—C7 | 1.478 (2) | C19—C20 | 1.361 (3) |
C8—H8 | 0.932 (19) | C19—H19 | 0.97 (2) |
F2—C1 | 1.361 (2) | C20—H20 | 1.02 (2) |
C3—C2 | 1.375 (3) | ||
C15—C10—C11 | 118.16 (15) | C1—C6—H6 | 121.0 (12) |
C15—C10—C9 | 123.09 (14) | C5—C6—H6 | 120.7 (12) |
C11—C10—C9 | 118.73 (15) | C14—C15—C10 | 121.24 (16) |
C16—O2—C12 | 118.17 (12) | C14—C15—H15 | 119.9 (10) |
C12—C11—C10 | 120.96 (16) | C10—C15—H15 | 118.9 (9) |
C12—C11—H11 | 120.0 (9) | C4—C5—C6 | 121.08 (16) |
C10—C11—H11 | 119.0 (9) | C4—C5—H5 | 120.8 (10) |
C13—C14—C15 | 119.00 (16) | C6—C5—H5 | 118.1 (10) |
C13—C14—H14 | 119.4 (10) | C17—C16—C21 | 120.76 (18) |
C15—C14—H14 | 121.6 (10) | C17—C16—O2 | 123.35 (15) |
C8—C9—C10 | 128.49 (16) | C21—C16—O2 | 115.87 (16) |
C8—C9—H9 | 114.7 (11) | F2—C1—C2 | 118.42 (17) |
C10—C9—H9 | 116.8 (11) | F2—C1—C6 | 118.64 (18) |
C13—C12—C11 | 119.03 (15) | C2—C1—C6 | 122.92 (17) |
C13—C12—O2 | 120.85 (15) | C1—C2—C3 | 118.09 (17) |
C11—C12—O2 | 120.04 (15) | C1—C2—H2 | 121.6 (11) |
C5—C4—C3 | 118.07 (15) | C3—C2—H2 | 120.3 (11) |
C5—C4—C7 | 123.47 (14) | C20—C21—C16 | 119.6 (2) |
C3—C4—C7 | 118.46 (15) | C20—C21—H21 | 121.3 (12) |
C9—C8—C7 | 121.68 (16) | C16—C21—H21 | 119.0 (12) |
C9—C8—H8 | 121.8 (11) | C16—C17—C18 | 118.5 (2) |
C7—C8—H8 | 116.6 (11) | C16—C17—H17 | 118.3 (10) |
C2—C3—C4 | 121.56 (18) | C18—C17—H17 | 123.3 (11) |
C2—C3—H3 | 121.0 (11) | C19—C18—C17 | 120.6 (2) |
C4—C3—H3 | 117.5 (11) | C19—C18—H18 | 124.8 (14) |
O1—C7—C8 | 119.37 (16) | C17—C18—H18 | 114.6 (14) |
O1—C7—C4 | 119.45 (15) | C20—C19—C18 | 119.8 (2) |
C8—C7—C4 | 121.17 (14) | C20—C19—H19 | 120.8 (13) |
F1—C13—C14 | 119.65 (15) | C18—C19—H19 | 119.4 (13) |
F1—C13—C12 | 118.74 (15) | C19—C20—C21 | 120.7 (2) |
C14—C13—C12 | 121.60 (15) | C19—C20—H20 | 119.9 (13) |
C1—C6—C5 | 118.27 (18) | C21—C20—H20 | 119.4 (13) |
C15—C10—C11—C12 | −1.6 (2) | O2—C12—C13—C14 | −176.72 (15) |
C9—C10—C11—C12 | 177.14 (15) | C13—C14—C15—C10 | −0.3 (2) |
C15—C10—C9—C8 | 11.4 (3) | C11—C10—C15—C14 | 1.2 (2) |
C11—C10—C9—C8 | −167.27 (17) | C9—C10—C15—C14 | −177.44 (15) |
C10—C11—C12—C13 | 1.0 (2) | C3—C4—C5—C6 | 0.2 (2) |
C10—C11—C12—O2 | 177.66 (13) | C7—C4—C5—C6 | −179.90 (15) |
C16—O2—C12—C13 | −72.5 (2) | C1—C6—C5—C4 | 0.3 (3) |
C16—O2—C12—C11 | 110.98 (18) | C12—O2—C16—C17 | −18.9 (2) |
C10—C9—C8—C7 | 178.70 (15) | C12—O2—C16—C21 | 162.58 (15) |
C5—C4—C3—C2 | −0.9 (2) | C5—C6—C1—F2 | −178.81 (15) |
C7—C4—C3—C2 | 179.22 (15) | C5—C6—C1—C2 | −0.2 (3) |
C9—C8—C7—O1 | 4.8 (3) | F2—C1—C2—C3 | 178.17 (15) |
C9—C8—C7—C4 | −175.44 (15) | C6—C1—C2—C3 | −0.5 (3) |
C5—C4—C7—O1 | −176.52 (17) | C4—C3—C2—C1 | 1.0 (3) |
C3—C4—C7—O1 | 3.4 (2) | C17—C16—C21—C20 | 2.5 (3) |
C5—C4—C7—C8 | 3.7 (2) | O2—C16—C21—C20 | −178.93 (16) |
C3—C4—C7—C8 | −176.41 (14) | C21—C16—C17—C18 | −2.8 (3) |
C15—C14—C13—F1 | 179.39 (14) | O2—C16—C17—C18 | 178.72 (16) |
C15—C14—C13—C12 | −0.2 (3) | C16—C17—C18—C19 | 1.2 (3) |
C11—C12—C13—F1 | −179.75 (14) | C17—C18—C19—C20 | 0.7 (3) |
O2—C12—C13—F1 | 3.7 (2) | C18—C19—C20—C21 | −1.1 (3) |
C11—C12—C13—C14 | −0.1 (3) | C16—C21—C20—C19 | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.95 (2) | 2.36 (2) | 3.271 (3) | 161 (2) |
C18—H18···O1ii | 0.90 (2) | 2.48 (2) | 3.345 (3) | 162 (2) |
C5—H5···Cg3iii | 0.98 (2) | 3.12 (2) | 3.894 (3) | 137 (1) |
C14—H14···Cg3iv | 0.95 (2) | 2.91 (2) | 3.780 (3) | 153 (1) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z. |
C21H14ClFO2 | Z = 2 |
Mr = 352.77 | F(000) = 364 |
Triclinic, P1 | Dx = 1.357 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.045 (6) Å | Cell parameters from 965 reflections |
b = 9.833 (6) Å | θ = 1.8–25.6° |
c = 11.474 (7) Å | µ = 0.24 mm−1 |
α = 99.109 (7)° | T = 290 K |
β = 104.800 (8)° | Block, colorless |
γ = 113.697 (9)° | 0.14 × 0.14 × 0.13 mm |
V = 863.3 (9) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3395 independent reflections |
Radiation source: fine-focus sealed tube | 2672 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.921, Tmax = 0.969 | k = −12→12 |
8889 measured reflections | l = −14→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0598P)2 + 0.1181P] where P = (Fo2 + 2Fc2)/3 |
3395 reflections | (Δ/σ)max < 0.001 |
282 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C21H14ClFO2 | γ = 113.697 (9)° |
Mr = 352.77 | V = 863.3 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.045 (6) Å | Mo Kα radiation |
b = 9.833 (6) Å | µ = 0.24 mm−1 |
c = 11.474 (7) Å | T = 290 K |
α = 99.109 (7)° | 0.14 × 0.14 × 0.13 mm |
β = 104.800 (8)° |
Bruker SMART APEX CCD area-detector diffractometer | 3395 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2672 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.969 | Rint = 0.025 |
8889 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.134 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.14 e Å−3 |
3395 reflections | Δρmin = −0.17 e Å−3 |
282 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.80478 (8) | −0.08233 (8) | 1.54625 (6) | 0.0844 (2) | |
F1 | 0.3850 (2) | 0.53648 (17) | 0.67286 (14) | 0.0977 (5) | |
O1 | 0.17510 (18) | −0.0423 (2) | 1.12692 (15) | 0.0821 (5) | |
O2 | 0.0572 (2) | 0.35710 (18) | 0.66076 (13) | 0.0764 (5) | |
C1 | 0.6701 (3) | −0.0510 (2) | 1.42744 (18) | 0.0587 (5) | |
C2 | 0.4951 (3) | −0.1411 (3) | 1.3894 (2) | 0.0641 (5) | |
C3 | 0.3879 (3) | −0.1147 (3) | 1.2967 (2) | 0.0625 (5) | |
C4 | 0.4542 (2) | 0.0022 (2) | 1.24170 (17) | 0.0531 (4) | |
C5 | 0.6326 (3) | 0.0909 (3) | 1.2821 (2) | 0.0618 (5) | |
C6 | 0.7412 (3) | 0.0657 (3) | 1.3758 (2) | 0.0665 (5) | |
C7 | 0.3295 (2) | 0.0254 (2) | 1.14370 (18) | 0.0584 (5) | |
C8 | 0.3895 (3) | 0.1278 (2) | 1.06718 (19) | 0.0592 (5) | |
C9 | 0.2777 (3) | 0.1439 (3) | 0.97700 (19) | 0.0595 (5) | |
C10 | 0.3106 (2) | 0.2425 (2) | 0.89503 (17) | 0.0552 (5) | |
C11 | 0.1716 (3) | 0.2531 (3) | 0.81658 (19) | 0.0618 (5) | |
C12 | 0.1963 (3) | 0.3517 (2) | 0.74220 (18) | 0.0627 (5) | |
C13 | 0.3606 (3) | 0.4386 (3) | 0.7448 (2) | 0.0682 (6) | |
C14 | 0.4998 (3) | 0.4288 (3) | 0.8190 (2) | 0.0705 (6) | |
C15 | 0.4744 (3) | 0.3311 (2) | 0.89346 (19) | 0.0606 (5) | |
C16 | 0.0107 (3) | 0.4685 (2) | 0.7048 (2) | 0.0607 (5) | |
C17 | 0.0689 (3) | 0.5504 (3) | 0.8294 (2) | 0.0765 (6) | |
C18 | 0.0146 (4) | 0.6599 (4) | 0.8621 (3) | 0.0957 (9) | |
C19 | −0.0963 (4) | 0.6846 (4) | 0.7712 (4) | 0.0970 (10) | |
C20 | −0.1569 (4) | 0.5991 (3) | 0.6481 (3) | 0.0878 (8) | |
C21 | −0.1036 (3) | 0.4910 (3) | 0.6142 (2) | 0.0705 (6) | |
H2 | 0.447 (3) | −0.223 (3) | 1.428 (2) | 0.076 (6)* | |
H3 | 0.265 (3) | −0.180 (3) | 1.266 (2) | 0.091 (8)* | |
H5 | 0.686 (3) | 0.173 (3) | 1.249 (2) | 0.075 (6)* | |
H6 | 0.863 (3) | 0.128 (3) | 1.406 (2) | 0.092 (8)* | |
H8 | 0.509 (3) | 0.181 (3) | 1.079 (2) | 0.076 (6)* | |
H9 | 0.163 (3) | 0.088 (2) | 0.967 (2) | 0.072 (6)* | |
H11 | 0.059 (3) | 0.193 (2) | 0.8184 (17) | 0.056 (5)* | |
H14 | 0.604 (3) | 0.488 (3) | 0.819 (2) | 0.088 (8)* | |
H15 | 0.572 (3) | 0.323 (2) | 0.948 (2) | 0.065 (6)* | |
H17 | 0.135 (3) | 0.531 (3) | 0.888 (2) | 0.077 (7)* | |
H18 | 0.052 (3) | 0.708 (3) | 0.942 (2) | 0.092 (7)* | |
H19 | −0.125 (4) | 0.756 (4) | 0.797 (3) | 0.128 (12)* | |
H20 | −0.236 (3) | 0.623 (3) | 0.584 (3) | 0.103 (8)* | |
H21 | −0.147 (3) | 0.429 (3) | 0.522 (2) | 0.085 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0872 (4) | 0.1072 (5) | 0.0811 (4) | 0.0635 (4) | 0.0221 (3) | 0.0467 (4) |
F1 | 0.1130 (12) | 0.0942 (10) | 0.0880 (9) | 0.0438 (9) | 0.0304 (9) | 0.0518 (8) |
O1 | 0.0515 (8) | 0.1122 (13) | 0.0771 (10) | 0.0305 (9) | 0.0161 (7) | 0.0452 (10) |
O2 | 0.0868 (11) | 0.0832 (10) | 0.0580 (8) | 0.0536 (9) | 0.0029 (8) | 0.0165 (8) |
C1 | 0.0666 (12) | 0.0679 (12) | 0.0554 (10) | 0.0431 (11) | 0.0202 (9) | 0.0225 (10) |
C2 | 0.0680 (13) | 0.0677 (13) | 0.0669 (12) | 0.0346 (11) | 0.0275 (11) | 0.0316 (11) |
C3 | 0.0575 (12) | 0.0692 (13) | 0.0636 (12) | 0.0297 (11) | 0.0217 (10) | 0.0246 (10) |
C4 | 0.0564 (11) | 0.0569 (11) | 0.0519 (10) | 0.0307 (9) | 0.0201 (9) | 0.0172 (9) |
C5 | 0.0557 (11) | 0.0660 (12) | 0.0695 (13) | 0.0305 (10) | 0.0203 (10) | 0.0315 (11) |
C6 | 0.0538 (12) | 0.0752 (14) | 0.0752 (14) | 0.0339 (11) | 0.0182 (11) | 0.0310 (12) |
C7 | 0.0538 (11) | 0.0677 (12) | 0.0538 (11) | 0.0296 (10) | 0.0166 (9) | 0.0178 (9) |
C8 | 0.0546 (11) | 0.0681 (12) | 0.0593 (11) | 0.0320 (10) | 0.0179 (9) | 0.0243 (10) |
C9 | 0.0532 (11) | 0.0677 (12) | 0.0559 (11) | 0.0299 (10) | 0.0141 (9) | 0.0177 (10) |
C10 | 0.0554 (11) | 0.0615 (11) | 0.0479 (10) | 0.0304 (9) | 0.0124 (8) | 0.0145 (9) |
C11 | 0.0565 (12) | 0.0713 (13) | 0.0571 (11) | 0.0332 (11) | 0.0130 (10) | 0.0192 (10) |
C12 | 0.0710 (13) | 0.0662 (12) | 0.0517 (10) | 0.0391 (11) | 0.0110 (10) | 0.0165 (9) |
C13 | 0.0841 (15) | 0.0640 (12) | 0.0573 (11) | 0.0348 (12) | 0.0226 (11) | 0.0224 (10) |
C14 | 0.0643 (13) | 0.0741 (14) | 0.0680 (13) | 0.0268 (12) | 0.0234 (12) | 0.0225 (12) |
C15 | 0.0578 (11) | 0.0710 (13) | 0.0548 (11) | 0.0342 (11) | 0.0159 (9) | 0.0171 (10) |
C16 | 0.0583 (11) | 0.0582 (11) | 0.0666 (12) | 0.0261 (10) | 0.0206 (10) | 0.0256 (10) |
C17 | 0.0677 (14) | 0.0768 (15) | 0.0739 (15) | 0.0318 (13) | 0.0146 (12) | 0.0157 (13) |
C18 | 0.0834 (19) | 0.0863 (19) | 0.100 (2) | 0.0303 (16) | 0.0363 (17) | 0.0018 (17) |
C19 | 0.0878 (19) | 0.0827 (18) | 0.150 (3) | 0.0516 (16) | 0.061 (2) | 0.044 (2) |
C20 | 0.0915 (18) | 0.0954 (19) | 0.115 (2) | 0.0592 (16) | 0.0523 (17) | 0.0593 (18) |
C21 | 0.0739 (14) | 0.0800 (15) | 0.0762 (15) | 0.0424 (12) | 0.0311 (12) | 0.0445 (13) |
Cl1—C1 | 1.739 (2) | C12—C11 | 1.380 (3) |
C4—C5 | 1.392 (3) | C11—H11 | 0.96 (2) |
C4—C3 | 1.395 (3) | C2—H2 | 0.98 (3) |
C4—C7 | 1.493 (3) | C5—H5 | 0.96 (2) |
C8—C9 | 1.328 (3) | C16—C17 | 1.371 (3) |
C8—C7 | 1.471 (3) | C16—C21 | 1.381 (3) |
C8—H8 | 0.95 (2) | C15—C14 | 1.374 (3) |
C10—C15 | 1.391 (3) | C15—H15 | 0.99 (2) |
C10—C11 | 1.399 (3) | C14—C13 | 1.377 (3) |
C10—C9 | 1.454 (3) | C14—H14 | 0.89 (3) |
O2—C12 | 1.389 (2) | C21—C20 | 1.376 (3) |
O2—C16 | 1.391 (2) | C21—H21 | 1.02 (2) |
O1—C7 | 1.227 (2) | C17—C18 | 1.390 (4) |
C1—C2 | 1.371 (3) | C17—H17 | 0.88 (2) |
C1—C6 | 1.377 (3) | C13—F1 | 1.352 (3) |
C6—C5 | 1.387 (3) | C20—C19 | 1.363 (5) |
C6—H6 | 0.95 (3) | C20—H20 | 1.01 (3) |
C3—C2 | 1.379 (3) | C18—C19 | 1.376 (5) |
C3—H3 | 0.96 (3) | C18—H18 | 0.87 (2) |
C9—H9 | 0.92 (2) | C19—H19 | 0.88 (3) |
C12—C13 | 1.374 (3) | ||
C5—C4—C3 | 118.09 (18) | C1—C2—H2 | 120.1 (13) |
C5—C4—C7 | 123.88 (18) | C3—C2—H2 | 120.8 (14) |
C3—C4—C7 | 118.03 (18) | C6—C5—C4 | 120.9 (2) |
C9—C8—C7 | 120.7 (2) | C6—C5—H5 | 116.7 (14) |
C9—C8—H8 | 118.7 (15) | C4—C5—H5 | 122.3 (14) |
C7—C8—H8 | 120.5 (14) | C17—C16—C21 | 120.6 (2) |
C15—C10—C11 | 118.2 (2) | C17—C16—O2 | 123.8 (2) |
C15—C10—C9 | 123.31 (18) | C21—C16—O2 | 115.53 (19) |
C11—C10—C9 | 118.50 (19) | C14—C15—C10 | 121.0 (2) |
C12—O2—C16 | 117.69 (15) | C14—C15—H15 | 120.7 (13) |
O1—C7—C8 | 119.80 (18) | C10—C15—H15 | 118.3 (13) |
O1—C7—C4 | 119.35 (18) | C15—C14—C13 | 119.3 (2) |
C8—C7—C4 | 120.85 (17) | C15—C14—H14 | 121.8 (17) |
C2—C1—C6 | 121.57 (19) | C13—C14—H14 | 118.8 (17) |
C2—C1—Cl1 | 118.99 (17) | C20—C21—C16 | 120.0 (3) |
C6—C1—Cl1 | 119.42 (17) | C20—C21—H21 | 119.9 (14) |
C1—C6—C5 | 119.0 (2) | C16—C21—H21 | 120.1 (14) |
C1—C6—H6 | 119.8 (16) | C16—C17—C18 | 118.6 (3) |
C5—C6—H6 | 121.2 (17) | C16—C17—H17 | 120.8 (15) |
C2—C3—C4 | 121.3 (2) | C18—C17—H17 | 120.6 (15) |
C2—C3—H3 | 120.2 (16) | F1—C13—C12 | 118.8 (2) |
C4—C3—H3 | 118.5 (16) | F1—C13—C14 | 119.7 (2) |
C8—C9—C10 | 129.2 (2) | C12—C13—C14 | 121.6 (2) |
C8—C9—H9 | 115.9 (15) | C19—C20—C21 | 120.0 (3) |
C10—C9—H9 | 114.9 (14) | C19—C20—H20 | 117.3 (15) |
C13—C12—C11 | 118.77 (19) | C21—C20—H20 | 122.6 (15) |
C13—C12—O2 | 120.2 (2) | C19—C18—C17 | 120.6 (3) |
C11—C12—O2 | 120.9 (2) | C19—C18—H18 | 123.4 (16) |
C12—C11—C10 | 121.1 (2) | C17—C18—H18 | 115.9 (16) |
C12—C11—H11 | 120.8 (12) | C20—C19—C18 | 120.1 (3) |
C10—C11—H11 | 118.0 (12) | C20—C19—H19 | 123 (2) |
C1—C2—C3 | 119.1 (2) | C18—C19—H19 | 117 (2) |
C9—C8—C7—O1 | −2.3 (3) | C1—C6—C5—C4 | 1.2 (3) |
C9—C8—C7—C4 | 177.57 (17) | C3—C4—C5—C6 | −1.1 (3) |
C5—C4—C7—O1 | −169.50 (19) | C7—C4—C5—C6 | 178.41 (18) |
C3—C4—C7—O1 | 10.0 (3) | C12—O2—C16—C17 | −14.0 (3) |
C5—C4—C7—C8 | 10.7 (3) | C12—O2—C16—C21 | 167.34 (19) |
C3—C4—C7—C8 | −169.80 (18) | C11—C10—C15—C14 | 1.4 (3) |
C2—C1—C6—C5 | −0.8 (3) | C9—C10—C15—C14 | −176.51 (19) |
Cl1—C1—C6—C5 | −179.30 (15) | C10—C15—C14—C13 | −0.1 (3) |
C5—C4—C3—C2 | 0.7 (3) | C17—C16—C21—C20 | 1.6 (3) |
C7—C4—C3—C2 | −178.81 (18) | O2—C16—C21—C20 | −179.7 (2) |
C7—C8—C9—C10 | 177.47 (18) | C21—C16—C17—C18 | −1.9 (4) |
C15—C10—C9—C8 | 5.3 (3) | O2—C16—C17—C18 | 179.4 (2) |
C11—C10—C9—C8 | −172.6 (2) | C11—C12—C13—F1 | −179.31 (18) |
C16—O2—C12—C13 | −89.9 (2) | O2—C12—C13—F1 | 4.3 (3) |
C16—O2—C12—C11 | 93.7 (2) | C11—C12—C13—C14 | 0.3 (3) |
C13—C12—C11—C10 | 1.0 (3) | O2—C12—C13—C14 | −176.14 (18) |
O2—C12—C11—C10 | 177.40 (16) | C15—C14—C13—F1 | 178.88 (19) |
C15—C10—C11—C12 | −1.8 (3) | C15—C14—C13—C12 | −0.7 (3) |
C9—C10—C11—C12 | 176.17 (18) | C16—C21—C20—C19 | 0.3 (4) |
C6—C1—C2—C3 | 0.5 (3) | C16—C17—C18—C19 | 0.5 (4) |
Cl1—C1—C2—C3 | 178.94 (15) | C21—C20—C19—C18 | −1.7 (4) |
C4—C3—C2—C1 | −0.4 (3) | C17—C18—C19—C20 | 1.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.96 (2) | 2.35 (2) | 3.285 (3) | 165 (2) |
C18—H18···O1ii | 0.87 (2) | 2.59 (2) | 3.381 (4) | 151 (2) |
C5—H5···Cg3iii | 0.96 (2) | 3.13 (3) | 3.940 (4) | 144 (2) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
C22H17FO2 | Z = 2 |
Mr = 332.36 | F(000) = 348 |
Triclinic, P1 | Dx = 1.257 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.196 (5) Å | Cell parameters from 795 reflections |
b = 9.726 (5) Å | θ = 1.7–26.4° |
c = 11.554 (7) Å | µ = 0.09 mm−1 |
α = 98.887 (9)° | T = 290 K |
β = 104.304 (9)° | Block, colorless |
γ = 113.754 (8)° | 0.24 × 0.14 × 0.12 mm |
V = 878.2 (9) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3476 independent reflections |
Radiation source: fine-focus sealed tube | 2575 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.940, Tmax = 0.990 | k = −12→12 |
9092 measured reflections | l = −14→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.0991P] where P = (Fo2 + 2Fc2)/3 |
3476 reflections | (Δ/σ)max < 0.001 |
294 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C22H17FO2 | γ = 113.754 (8)° |
Mr = 332.36 | V = 878.2 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.196 (5) Å | Mo Kα radiation |
b = 9.726 (5) Å | µ = 0.09 mm−1 |
c = 11.554 (7) Å | T = 290 K |
α = 98.887 (9)° | 0.24 × 0.14 × 0.12 mm |
β = 104.304 (9)° |
Bruker SMART APEX CCD area-detector diffractometer | 3476 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2575 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.990 | Rint = 0.014 |
9092 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.13 e Å−3 |
3476 reflections | Δρmin = −0.16 e Å−3 |
294 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.17659 (14) | −0.04092 (16) | 1.13449 (11) | 0.0907 (4) | |
O2 | 0.06739 (15) | 0.36096 (14) | 0.66600 (10) | 0.0844 (4) | |
F1 | 0.38959 (15) | 0.53565 (13) | 0.67279 (10) | 0.1047 (4) | |
C1 | 0.6681 (2) | −0.05428 (18) | 1.42690 (14) | 0.0668 (4) | |
C2 | 0.4938 (2) | −0.1431 (2) | 1.38939 (16) | 0.0728 (4) | |
C3 | 0.3865 (2) | −0.11751 (19) | 1.29901 (15) | 0.0685 (4) | |
C4 | 0.45019 (17) | −0.00169 (16) | 1.24141 (13) | 0.0590 (4) | |
C5 | 0.6250 (2) | 0.08632 (19) | 1.27797 (16) | 0.0695 (4) | |
C6 | 0.7315 (2) | 0.0602 (2) | 1.36934 (16) | 0.0740 (4) | |
C7 | 0.32788 (19) | 0.02334 (18) | 1.14699 (14) | 0.0640 (4) | |
C8 | 0.3861 (2) | 0.12508 (18) | 1.06832 (14) | 0.0649 (4) | |
C9 | 0.2770 (2) | 0.14442 (19) | 0.98197 (14) | 0.0648 (4) | |
C10 | 0.31118 (18) | 0.24397 (16) | 0.89912 (13) | 0.0602 (4) | |
C11 | 0.1763 (2) | 0.25677 (19) | 0.82261 (14) | 0.0661 (4) | |
C12 | 0.2026 (2) | 0.35441 (19) | 0.74715 (14) | 0.0676 (4) | |
C13 | 0.3648 (2) | 0.43956 (19) | 0.74719 (15) | 0.0730 (4) | |
C14 | 0.4997 (2) | 0.4273 (2) | 0.81945 (16) | 0.0739 (4) | |
C15 | 0.4725 (2) | 0.32965 (18) | 0.89480 (14) | 0.0655 (4) | |
C16 | 0.01872 (19) | 0.47103 (18) | 0.70882 (15) | 0.0667 (4) | |
C17 | 0.0755 (2) | 0.5551 (2) | 0.83148 (18) | 0.0822 (5) | |
C18 | 0.0179 (3) | 0.6631 (3) | 0.8624 (3) | 0.1039 (7) | |
C19 | −0.0937 (3) | 0.6838 (3) | 0.7718 (3) | 0.1062 (7) | |
C20 | −0.1520 (3) | 0.5954 (3) | 0.6516 (3) | 0.0987 (6) | |
C21 | −0.0965 (2) | 0.4896 (2) | 0.61837 (19) | 0.0798 (5) | |
C22 | 0.7837 (3) | −0.0820 (3) | 1.5274 (2) | 0.0892 (6) | |
H2 | 0.446 (2) | −0.224 (2) | 1.4274 (15) | 0.080 (5)* | |
H3 | 0.267 (2) | −0.176 (2) | 1.2749 (16) | 0.088 (5)* | |
H5 | 0.673 (2) | 0.164 (2) | 1.2396 (15) | 0.077 (5)* | |
H6 | 0.850 (2) | 0.121 (2) | 1.3957 (16) | 0.085 (5)* | |
H8 | 0.505 (2) | 0.177 (2) | 1.0836 (15) | 0.081 (5)* | |
H9 | 0.160 (2) | 0.0865 (19) | 0.9748 (15) | 0.077 (5)* | |
H11 | 0.066 (2) | 0.1988 (19) | 0.8246 (15) | 0.075 (5)* | |
H14 | 0.606 (2) | 0.486 (2) | 0.8163 (15) | 0.085 (5)* | |
H15 | 0.570 (2) | 0.3187 (17) | 0.9463 (14) | 0.072 (4)* | |
H17 | 0.152 (2) | 0.536 (2) | 0.8917 (17) | 0.087 (5)* | |
H18 | 0.057 (3) | 0.708 (3) | 0.945 (2) | 0.106 (7)* | |
H19 | −0.128 (3) | 0.761 (3) | 0.798 (2) | 0.131 (8)* | |
H20 | −0.243 (3) | 0.606 (3) | 0.583 (2) | 0.132 (8)* | |
H21 | −0.132 (3) | 0.427 (2) | 0.529 (2) | 0.111 (7)* | |
H22B | 0.825 (3) | −0.147 (3) | 1.492 (2) | 0.126 (8)* | |
H22C | 0.732 (4) | −0.121 (4) | 1.584 (3) | 0.163 (11)* | |
H22A | 0.892 (4) | 0.017 (4) | 1.578 (3) | 0.168 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1226 (9) | 0.0997 (8) | 0.0924 (7) | 0.0449 (7) | 0.0355 (6) | 0.0487 (6) |
O1 | 0.0575 (7) | 0.1212 (10) | 0.0891 (8) | 0.0324 (7) | 0.0223 (6) | 0.0475 (7) |
O2 | 0.0951 (8) | 0.0934 (8) | 0.0635 (7) | 0.0574 (7) | 0.0064 (6) | 0.0140 (6) |
C1 | 0.0781 (10) | 0.0719 (9) | 0.0616 (8) | 0.0452 (8) | 0.0234 (7) | 0.0190 (7) |
C2 | 0.0841 (11) | 0.0712 (10) | 0.0738 (10) | 0.0378 (9) | 0.0347 (9) | 0.0311 (8) |
C3 | 0.0634 (9) | 0.0693 (9) | 0.0703 (9) | 0.0271 (8) | 0.0247 (8) | 0.0204 (8) |
C4 | 0.0607 (8) | 0.0585 (8) | 0.0588 (8) | 0.0280 (7) | 0.0223 (7) | 0.0147 (6) |
C5 | 0.0619 (9) | 0.0702 (9) | 0.0776 (10) | 0.0288 (8) | 0.0225 (8) | 0.0309 (8) |
C6 | 0.0584 (9) | 0.0788 (10) | 0.0828 (11) | 0.0319 (8) | 0.0180 (8) | 0.0270 (9) |
C7 | 0.0578 (8) | 0.0696 (9) | 0.0613 (8) | 0.0282 (7) | 0.0186 (7) | 0.0157 (7) |
C8 | 0.0578 (9) | 0.0709 (9) | 0.0656 (9) | 0.0293 (7) | 0.0200 (7) | 0.0211 (7) |
C9 | 0.0573 (8) | 0.0700 (9) | 0.0617 (9) | 0.0277 (7) | 0.0164 (7) | 0.0156 (7) |
C10 | 0.0601 (8) | 0.0636 (8) | 0.0538 (8) | 0.0303 (7) | 0.0149 (6) | 0.0108 (6) |
C11 | 0.0591 (9) | 0.0718 (9) | 0.0609 (9) | 0.0298 (8) | 0.0145 (7) | 0.0131 (7) |
C12 | 0.0741 (10) | 0.0703 (9) | 0.0551 (8) | 0.0384 (8) | 0.0117 (7) | 0.0118 (7) |
C13 | 0.0891 (12) | 0.0676 (9) | 0.0607 (9) | 0.0353 (9) | 0.0237 (8) | 0.0197 (7) |
C14 | 0.0684 (10) | 0.0747 (10) | 0.0717 (10) | 0.0258 (8) | 0.0262 (8) | 0.0193 (8) |
C15 | 0.0597 (9) | 0.0725 (9) | 0.0612 (8) | 0.0319 (7) | 0.0167 (7) | 0.0133 (7) |
C16 | 0.0649 (9) | 0.0627 (8) | 0.0750 (10) | 0.0274 (7) | 0.0264 (8) | 0.0280 (8) |
C17 | 0.0717 (11) | 0.0789 (11) | 0.0830 (12) | 0.0313 (9) | 0.0186 (9) | 0.0110 (9) |
C18 | 0.0907 (14) | 0.0889 (14) | 0.1131 (18) | 0.0313 (12) | 0.0391 (14) | 0.0006 (13) |
C19 | 0.0940 (15) | 0.0881 (14) | 0.163 (3) | 0.0530 (12) | 0.0619 (17) | 0.0446 (16) |
C20 | 0.1047 (15) | 0.1044 (15) | 0.1260 (19) | 0.0640 (13) | 0.0566 (14) | 0.0633 (15) |
C21 | 0.0844 (11) | 0.0912 (12) | 0.0853 (12) | 0.0470 (10) | 0.0377 (10) | 0.0494 (10) |
C22 | 0.1021 (15) | 0.1061 (15) | 0.0815 (13) | 0.0665 (14) | 0.0288 (12) | 0.0366 (12) |
C10—C15 | 1.397 (2) | C1—C2 | 1.389 (2) |
C10—C11 | 1.397 (2) | C1—C22 | 1.507 (2) |
C10—C9 | 1.464 (2) | C5—C6 | 1.383 (2) |
C4—C5 | 1.392 (2) | C5—H5 | 0.945 (17) |
C4—C3 | 1.395 (2) | F1—C13 | 1.356 (2) |
C4—C7 | 1.487 (2) | C16—C17 | 1.372 (2) |
O2—C16 | 1.387 (2) | C16—C21 | 1.383 (2) |
O2—C12 | 1.3911 (19) | C6—H6 | 0.946 (19) |
C11—C12 | 1.377 (2) | C2—H2 | 0.962 (18) |
C11—H11 | 0.951 (18) | C15—H15 | 1.001 (16) |
C8—C9 | 1.324 (2) | C21—C20 | 1.366 (3) |
C8—C7 | 1.478 (2) | C21—H21 | 1.01 (2) |
C8—H8 | 0.954 (18) | C22—H22B | 0.95 (3) |
C9—H9 | 0.964 (18) | C22—H22C | 0.94 (3) |
C7—O1 | 1.2326 (19) | C22—H22A | 1.01 (3) |
C3—C2 | 1.376 (2) | C17—C18 | 1.392 (3) |
C3—H3 | 0.949 (19) | C17—H17 | 0.954 (18) |
C12—C13 | 1.384 (3) | C18—C19 | 1.375 (4) |
C14—C13 | 1.374 (3) | C18—H18 | 0.89 (2) |
C14—C15 | 1.376 (2) | C20—C19 | 1.359 (4) |
C14—H14 | 0.925 (18) | C20—H20 | 1.05 (2) |
C1—C6 | 1.385 (2) | C19—H19 | 0.96 (3) |
C15—C10—C11 | 118.34 (15) | C17—C16—O2 | 123.88 (15) |
C15—C10—C9 | 123.30 (13) | C21—C16—O2 | 115.07 (15) |
C11—C10—C9 | 118.34 (14) | C5—C6—C1 | 121.19 (16) |
C5—C4—C3 | 117.94 (14) | C5—C6—H6 | 121.2 (11) |
C5—C4—C7 | 123.77 (14) | C1—C6—H6 | 117.6 (11) |
C3—C4—C7 | 118.27 (14) | C3—C2—C1 | 121.35 (16) |
C16—O2—C12 | 118.04 (12) | C3—C2—H2 | 118.7 (10) |
C12—C11—C10 | 120.77 (16) | C1—C2—H2 | 120.0 (10) |
C12—C11—H11 | 120.1 (10) | C14—C15—C10 | 121.20 (15) |
C10—C11—H11 | 119.1 (10) | C14—C15—H15 | 119.2 (9) |
C9—C8—C7 | 120.75 (15) | C10—C15—H15 | 119.6 (9) |
C9—C8—H8 | 122.1 (10) | F1—C13—C14 | 119.67 (16) |
C7—C8—H8 | 117.1 (10) | F1—C13—C12 | 118.79 (16) |
C8—C9—C10 | 128.49 (15) | C14—C13—C12 | 121.54 (16) |
C8—C9—H9 | 114.8 (10) | C20—C21—C16 | 119.4 (2) |
C10—C9—H9 | 116.7 (10) | C20—C21—H21 | 122.7 (12) |
O1—C7—C8 | 119.68 (14) | C16—C21—H21 | 117.9 (12) |
O1—C7—C4 | 119.71 (14) | C1—C22—H22B | 110.5 (14) |
C8—C7—C4 | 120.61 (13) | C1—C22—H22C | 111.6 (18) |
C2—C3—C4 | 120.79 (16) | H22B—C22—H22C | 113 (2) |
C2—C3—H3 | 121.3 (11) | C1—C22—H22A | 112.6 (17) |
C4—C3—H3 | 117.9 (11) | H22B—C22—H22A | 102 (2) |
C11—C12—C13 | 119.15 (15) | H22C—C22—H22A | 107 (2) |
C11—C12—O2 | 120.83 (15) | C16—C17—C18 | 118.3 (2) |
C13—C12—O2 | 119.90 (15) | C16—C17—H17 | 118.6 (11) |
C13—C14—C15 | 118.97 (17) | C18—C17—H17 | 123.0 (11) |
C13—C14—H14 | 118.9 (11) | C19—C18—C17 | 120.5 (2) |
C15—C14—H14 | 122.2 (11) | C19—C18—H18 | 127.2 (14) |
C6—C1—C2 | 117.94 (15) | C17—C18—H18 | 112.2 (14) |
C6—C1—C22 | 121.38 (18) | C19—C20—C21 | 120.8 (2) |
C2—C1—C22 | 120.69 (17) | C19—C20—H20 | 120.4 (13) |
C6—C5—C4 | 120.79 (16) | C21—C20—H20 | 118.8 (13) |
C6—C5—H5 | 118.8 (10) | C20—C19—C18 | 120.0 (2) |
C4—C5—H5 | 120.4 (10) | C20—C19—H19 | 122.8 (15) |
C17—C16—C21 | 121.04 (17) | C18—C19—H19 | 117.2 (15) |
C15—C10—C11—C12 | −1.6 (2) | C2—C1—C6—C5 | 0.5 (2) |
C9—C10—C11—C12 | 176.97 (13) | C22—C1—C6—C5 | −179.35 (17) |
C7—C8—C9—C10 | 177.56 (13) | C4—C3—C2—C1 | 0.5 (2) |
C15—C10—C9—C8 | 4.3 (2) | C6—C1—C2—C3 | −0.8 (2) |
C11—C10—C9—C8 | −174.20 (15) | C22—C1—C2—C3 | 179.02 (17) |
C9—C8—C7—O1 | −2.0 (2) | C13—C14—C15—C10 | −0.2 (2) |
C9—C8—C7—C4 | 178.26 (13) | C11—C10—C15—C14 | 1.5 (2) |
C5—C4—C7—O1 | −168.08 (15) | C9—C10—C15—C14 | −176.99 (14) |
C3—C4—C7—O1 | 10.4 (2) | C15—C14—C13—F1 | 179.79 (14) |
C5—C4—C7—C8 | 11.7 (2) | C15—C14—C13—C12 | −1.0 (2) |
C3—C4—C7—C8 | −169.90 (13) | C11—C12—C13—F1 | −179.89 (13) |
C5—C4—C3—C2 | 0.2 (2) | O2—C12—C13—F1 | 4.0 (2) |
C7—C4—C3—C2 | −178.31 (14) | C11—C12—C13—C14 | 0.9 (2) |
C10—C11—C12—C13 | 0.4 (2) | O2—C12—C13—C14 | −175.24 (14) |
C10—C11—C12—O2 | 176.52 (12) | C17—C16—C21—C20 | 1.2 (3) |
C16—O2—C12—C11 | 91.19 (18) | O2—C16—C21—C20 | 180.00 (16) |
C16—O2—C12—C13 | −92.74 (18) | C21—C16—C17—C18 | −1.8 (3) |
C3—C4—C5—C6 | −0.5 (2) | O2—C16—C17—C18 | 179.55 (16) |
C7—C4—C5—C6 | 177.89 (14) | C16—C17—C18—C19 | 0.3 (3) |
C12—O2—C16—C17 | −11.6 (2) | C16—C21—C20—C19 | 0.9 (3) |
C12—O2—C16—C21 | 169.66 (14) | C21—C20—C19—C18 | −2.4 (3) |
C4—C5—C6—C1 | 0.2 (3) | C17—C18—C19—C20 | 1.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.95 (2) | 2.35 (2) | 3.288 (3) | 167 (2) |
C18—H18···O1ii | 0.89 (2) | 2.64 (2) | 3.443 (3) | 150 (2) |
C5—H5···Cg3iii | 0.95 (2) | 3.21 (2) | 3.980 (3) | 140 (1) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
C22H17FO3 | Z = 2 |
Mr = 348.36 | F(000) = 364 |
Triclinic, P1 | Dx = 1.349 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.645 (4) Å | Cell parameters from 856 reflections |
b = 10.111 (5) Å | θ = 1.4–25.6° |
c = 10.537 (6) Å | µ = 0.10 mm−1 |
α = 66.706 (7)° | T = 290 K |
β = 65.347 (8)° | Block, colorless |
γ = 80.949 (9)° | 0.12 × 0.08 × 0.04 mm |
V = 857.8 (7) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3419 independent reflections |
Radiation source: fine-focus sealed tube | 2219 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.946, Tmax = 0.996 | k = −12→12 |
8983 measured reflections | l = −12→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.1909P] where P = (Fo2 + 2Fc2)/3 |
3419 reflections | (Δ/σ)max < 0.001 |
303 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C22H17FO3 | γ = 80.949 (9)° |
Mr = 348.36 | V = 857.8 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.645 (4) Å | Mo Kα radiation |
b = 10.111 (5) Å | µ = 0.10 mm−1 |
c = 10.537 (6) Å | T = 290 K |
α = 66.706 (7)° | 0.12 × 0.08 × 0.04 mm |
β = 65.347 (8)° |
Bruker SMART APEX CCD area-detector diffractometer | 3419 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2219 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.996 | Rint = 0.028 |
8983 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.111 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.14 e Å−3 |
3419 reflections | Δρmin = −0.17 e Å−3 |
303 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.55831 (16) | 0.45569 (13) | 0.61429 (15) | 0.0661 (4) | |
O1 | 0.88328 (18) | −0.31997 (16) | 0.49310 (17) | 0.0648 (5) | |
O2 | 0.35389 (16) | 0.24070 (16) | 0.71921 (16) | 0.0522 (4) | |
O3 | 1.35658 (17) | −0.23643 (16) | −0.17089 (16) | 0.0572 (4) | |
C1 | 1.2618 (2) | −0.2390 (2) | −0.0307 (2) | 0.0434 (5) | |
C2 | 1.2244 (3) | −0.3601 (2) | 0.1001 (3) | 0.0465 (6) | |
C3 | 1.1244 (2) | −0.3490 (2) | 0.2347 (3) | 0.0453 (5) | |
C4 | 1.0616 (2) | −0.2182 (2) | 0.2431 (2) | 0.0409 (5) | |
C5 | 1.1055 (3) | −0.0975 (2) | 0.1111 (2) | 0.0475 (6) | |
C6 | 1.2031 (3) | −0.1078 (2) | −0.0237 (3) | 0.0503 (6) | |
C7 | 0.9440 (2) | −0.2112 (2) | 0.3868 (2) | 0.0456 (5) | |
C8 | 0.9002 (3) | −0.0681 (2) | 0.3980 (2) | 0.0476 (6) | |
C9 | 0.7648 (3) | −0.0433 (2) | 0.4905 (2) | 0.0449 (5) | |
C10 | 0.7117 (2) | 0.0919 (2) | 0.5157 (2) | 0.0402 (5) | |
C11 | 0.5588 (2) | 0.1042 (2) | 0.6053 (2) | 0.0429 (5) | |
C12 | 0.5074 (2) | 0.2269 (2) | 0.6367 (2) | 0.0431 (5) | |
C13 | 0.6086 (3) | 0.3375 (2) | 0.5792 (2) | 0.0465 (5) | |
C14 | 0.7590 (3) | 0.3300 (3) | 0.4895 (2) | 0.0502 (6) | |
C15 | 0.8094 (3) | 0.2067 (2) | 0.4584 (2) | 0.0473 (6) | |
C16 | 0.3127 (2) | 0.2483 (2) | 0.8594 (2) | 0.0408 (5) | |
C17 | 0.4031 (3) | 0.1986 (3) | 0.9399 (3) | 0.0516 (6) | |
C18 | 0.3492 (3) | 0.2045 (3) | 1.0820 (3) | 0.0570 (6) | |
C19 | 0.2081 (3) | 0.2603 (3) | 1.1407 (3) | 0.0558 (6) | |
C20 | 0.1193 (3) | 0.3092 (3) | 1.0585 (3) | 0.0531 (6) | |
C21 | 0.1705 (2) | 0.3037 (2) | 0.9175 (2) | 0.0468 (5) | |
C22 | 1.4148 (4) | −0.3683 (3) | −0.1905 (4) | 0.0729 (9) | |
H2 | 1.263 (2) | −0.448 (2) | 0.098 (2) | 0.057 (7)* | |
H3 | 1.101 (2) | −0.430 (2) | 0.324 (2) | 0.041 (6)* | |
H5 | 1.066 (2) | −0.005 (2) | 0.112 (2) | 0.048 (6)* | |
H6 | 1.231 (2) | −0.028 (2) | −0.116 (2) | 0.048 (6)* | |
H8 | 0.976 (2) | 0.009 (2) | 0.335 (2) | 0.056 (6)* | |
H9 | 0.690 (2) | −0.124 (2) | 0.550 (2) | 0.051 (6)* | |
H11 | 0.491 (2) | 0.029 (2) | 0.644 (2) | 0.042 (6)* | |
H13 | 0.828 (2) | 0.410 (2) | 0.452 (2) | 0.059 (7)* | |
H15 | 0.915 (2) | 0.197 (2) | 0.402 (2) | 0.047 (6)* | |
H17 | 0.500 (3) | 0.161 (2) | 0.900 (2) | 0.060 (7)* | |
H18 | 0.415 (3) | 0.170 (2) | 1.138 (2) | 0.064 (7)* | |
H19 | 0.174 (2) | 0.266 (2) | 1.239 (2) | 0.058 (6)* | |
H20 | 0.020 (3) | 0.348 (2) | 1.101 (2) | 0.062 (7)* | |
H21 | 0.111 (2) | 0.338 (2) | 0.855 (2) | 0.057 (6)* | |
H22B | 1.477 (3) | −0.417 (3) | −0.126 (3) | 0.094 (10)* | |
H22A | 1.483 (3) | −0.342 (3) | −0.297 (3) | 0.088 (9)* | |
H22C | 1.334 (3) | −0.435 (3) | −0.152 (3) | 0.095 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0788 (10) | 0.0545 (8) | 0.0730 (9) | 0.0132 (7) | −0.0261 (8) | −0.0399 (7) |
O1 | 0.0685 (11) | 0.0447 (9) | 0.0529 (10) | 0.0022 (8) | −0.0064 (8) | −0.0094 (8) |
O2 | 0.0407 (9) | 0.0750 (11) | 0.0526 (9) | 0.0137 (7) | −0.0192 (7) | −0.0390 (8) |
O3 | 0.0643 (11) | 0.0535 (10) | 0.0523 (9) | 0.0050 (8) | −0.0116 (8) | −0.0317 (8) |
C1 | 0.0411 (12) | 0.0469 (13) | 0.0498 (13) | 0.0021 (10) | −0.0165 (10) | −0.0272 (11) |
C2 | 0.0492 (14) | 0.0366 (13) | 0.0584 (15) | 0.0099 (10) | −0.0220 (11) | −0.0246 (11) |
C3 | 0.0496 (13) | 0.0365 (12) | 0.0474 (13) | 0.0031 (10) | −0.0193 (11) | −0.0138 (11) |
C4 | 0.0418 (12) | 0.0381 (12) | 0.0447 (12) | 0.0064 (9) | −0.0169 (10) | −0.0194 (10) |
C5 | 0.0556 (14) | 0.0334 (12) | 0.0520 (14) | 0.0102 (10) | −0.0173 (11) | −0.0218 (11) |
C6 | 0.0597 (15) | 0.0381 (13) | 0.0440 (13) | 0.0011 (11) | −0.0123 (11) | −0.0150 (11) |
C7 | 0.0458 (13) | 0.0438 (13) | 0.0466 (13) | 0.0061 (10) | −0.0179 (11) | −0.0182 (11) |
C8 | 0.0486 (14) | 0.0457 (14) | 0.0414 (12) | 0.0037 (11) | −0.0079 (11) | −0.0205 (11) |
C9 | 0.0486 (14) | 0.0429 (13) | 0.0403 (12) | 0.0029 (11) | −0.0151 (11) | −0.0157 (10) |
C10 | 0.0424 (12) | 0.0426 (12) | 0.0339 (11) | 0.0056 (10) | −0.0127 (9) | −0.0166 (9) |
C11 | 0.0429 (13) | 0.0483 (13) | 0.0378 (11) | 0.0001 (11) | −0.0138 (10) | −0.0181 (10) |
C12 | 0.0398 (12) | 0.0556 (14) | 0.0390 (11) | 0.0104 (11) | −0.0164 (10) | −0.0250 (11) |
C13 | 0.0572 (15) | 0.0440 (13) | 0.0460 (12) | 0.0109 (11) | −0.0228 (11) | −0.0253 (10) |
C14 | 0.0538 (15) | 0.0492 (14) | 0.0462 (13) | −0.0035 (12) | −0.0141 (11) | −0.0206 (11) |
C15 | 0.0391 (13) | 0.0552 (14) | 0.0421 (12) | 0.0019 (11) | −0.0067 (10) | −0.0229 (11) |
C16 | 0.0401 (12) | 0.0432 (12) | 0.0407 (11) | 0.0034 (10) | −0.0131 (10) | −0.0210 (10) |
C17 | 0.0407 (13) | 0.0623 (15) | 0.0517 (14) | 0.0092 (11) | −0.0168 (11) | −0.0253 (12) |
C18 | 0.0520 (15) | 0.0731 (17) | 0.0453 (14) | −0.0053 (13) | −0.0193 (12) | −0.0185 (12) |
C19 | 0.0537 (16) | 0.0668 (16) | 0.0401 (13) | −0.0136 (12) | −0.0054 (12) | −0.0216 (12) |
C20 | 0.0422 (14) | 0.0568 (15) | 0.0522 (14) | 0.0029 (11) | −0.0051 (12) | −0.0272 (12) |
C21 | 0.0390 (13) | 0.0517 (14) | 0.0515 (14) | 0.0048 (10) | −0.0166 (11) | −0.0235 (11) |
C22 | 0.085 (2) | 0.0600 (18) | 0.069 (2) | 0.0038 (17) | −0.0081 (18) | −0.0444 (17) |
F1—C13 | 1.348 (2) | C9—C8 | 1.321 (3) |
C3—C2 | 1.381 (3) | C9—H9 | 0.99 (2) |
C3—C4 | 1.385 (3) | C15—H15 | 0.96 (2) |
C3—H3 | 0.937 (19) | C2—H2 | 0.92 (2) |
O2—C12 | 1.387 (2) | C8—H8 | 0.97 (2) |
O2—C16 | 1.392 (2) | C5—C6 | 1.373 (3) |
O3—C1 | 1.367 (2) | C5—H5 | 0.95 (2) |
O3—C22 | 1.422 (3) | C6—H6 | 0.95 (2) |
C10—C15 | 1.383 (3) | C16—C17 | 1.370 (3) |
C10—C11 | 1.399 (3) | C16—C21 | 1.377 (3) |
C10—C9 | 1.468 (3) | C21—C20 | 1.379 (3) |
C11—C12 | 1.374 (3) | C21—H21 | 0.97 (2) |
C11—H11 | 0.93 (2) | C17—C18 | 1.388 (3) |
O1—C7 | 1.220 (2) | C17—H17 | 0.94 (2) |
C4—C5 | 1.390 (3) | C18—C19 | 1.373 (3) |
C4—C7 | 1.487 (3) | C18—H18 | 0.97 (2) |
C12—C13 | 1.373 (3) | C20—C19 | 1.369 (3) |
C14—C13 | 1.372 (3) | C20—H20 | 0.97 (2) |
C14—C15 | 1.378 (3) | C22—H22B | 1.02 (3) |
C14—H13 | 0.98 (2) | C22—H22A | 0.99 (3) |
C1—C6 | 1.376 (3) | C22—H22C | 0.95 (3) |
C1—C2 | 1.385 (3) | C19—H19 | 0.97 (2) |
C7—C8 | 1.479 (3) | ||
C2—C3—C4 | 121.5 (2) | C3—C2—H2 | 119.7 (13) |
C2—C3—H3 | 120.3 (11) | C1—C2—H2 | 120.5 (13) |
C4—C3—H3 | 118.2 (11) | C9—C8—C7 | 122.4 (2) |
C12—O2—C16 | 118.08 (15) | C9—C8—H8 | 120.4 (12) |
C1—O3—C22 | 119.1 (2) | C7—C8—H8 | 117.2 (12) |
C15—C10—C11 | 118.4 (2) | C6—C5—C4 | 121.4 (2) |
C15—C10—C9 | 122.2 (2) | C6—C5—H5 | 118.2 (12) |
C11—C10—C9 | 119.4 (2) | C4—C5—H5 | 120.4 (12) |
C12—C11—C10 | 120.7 (2) | C5—C6—C1 | 120.3 (2) |
C12—C11—H11 | 119.4 (12) | C5—C6—H6 | 123.1 (12) |
C10—C11—H11 | 119.9 (12) | C1—C6—H6 | 116.6 (12) |
C3—C4—C5 | 117.5 (2) | C17—C16—C21 | 121.0 (2) |
C3—C4—C7 | 120.35 (19) | C17—C16—O2 | 123.03 (18) |
C5—C4—C7 | 121.99 (18) | C21—C16—O2 | 115.96 (18) |
C13—C12—C11 | 119.1 (2) | C16—C21—C20 | 119.3 (2) |
C13—C12—O2 | 120.80 (19) | C16—C21—H21 | 117.5 (12) |
C11—C12—O2 | 120.1 (2) | C20—C21—H21 | 123.2 (12) |
C13—C14—C15 | 118.6 (2) | C16—C17—C18 | 118.9 (2) |
C13—C14—H13 | 119.5 (12) | C16—C17—H17 | 120.7 (13) |
C15—C14—H13 | 121.9 (13) | C18—C17—H17 | 120.4 (13) |
F1—C13—C14 | 119.4 (2) | C19—C18—C17 | 120.7 (2) |
F1—C13—C12 | 118.68 (19) | C19—C18—H18 | 120.8 (13) |
C14—C13—C12 | 121.9 (2) | C17—C18—H18 | 118.4 (13) |
O3—C1—C6 | 115.17 (19) | C19—C20—C21 | 120.7 (2) |
O3—C1—C2 | 125.42 (19) | C19—C20—H20 | 119.0 (13) |
C6—C1—C2 | 119.4 (2) | C21—C20—H20 | 120.3 (13) |
O1—C7—C8 | 120.24 (19) | O3—C22—H22B | 109.1 (16) |
O1—C7—C4 | 121.39 (19) | O3—C22—H22A | 105.7 (16) |
C8—C7—C4 | 118.36 (19) | H22B—C22—H22A | 109 (2) |
C8—C9—C10 | 127.0 (2) | O3—C22—H22C | 111.0 (17) |
C8—C9—H9 | 117.4 (12) | H22B—C22—H22C | 104 (2) |
C10—C9—H9 | 115.5 (12) | H22A—C22—H22C | 118 (2) |
C14—C15—C10 | 121.3 (2) | C20—C19—C18 | 119.5 (2) |
C14—C15—H15 | 119.5 (12) | C20—C19—H19 | 120.9 (13) |
C10—C15—H15 | 119.0 (12) | C18—C19—H19 | 119.6 (13) |
C3—C2—C1 | 119.8 (2) | ||
C15—C10—C11—C12 | −0.6 (3) | C11—C10—C15—C14 | 0.8 (3) |
C9—C10—C11—C12 | 176.89 (19) | C9—C10—C15—C14 | −176.7 (2) |
C2—C3—C4—C5 | −1.4 (3) | C4—C3—C2—C1 | −1.0 (3) |
C2—C3—C4—C7 | 174.7 (2) | O3—C1—C2—C3 | −178.6 (2) |
C10—C11—C12—C13 | −0.2 (3) | C6—C1—C2—C3 | 2.4 (3) |
C10—C11—C12—O2 | 176.68 (17) | C10—C9—C8—C7 | 177.1 (2) |
C16—O2—C12—C13 | −68.0 (2) | O1—C7—C8—C9 | −25.9 (3) |
C16—O2—C12—C11 | 115.2 (2) | C4—C7—C8—C9 | 153.5 (2) |
C15—C14—C13—F1 | 178.12 (19) | C3—C4—C5—C6 | 2.4 (3) |
C15—C14—C13—C12 | −0.8 (3) | C7—C4—C5—C6 | −173.6 (2) |
C11—C12—C13—F1 | −178.00 (18) | C4—C5—C6—C1 | −1.0 (4) |
O2—C12—C13—F1 | 5.1 (3) | O3—C1—C6—C5 | 179.5 (2) |
C11—C12—C13—C14 | 1.0 (3) | C2—C1—C6—C5 | −1.4 (3) |
O2—C12—C13—C14 | −175.89 (19) | C12—O2—C16—C17 | −21.4 (3) |
C22—O3—C1—C6 | −175.9 (3) | C12—O2—C16—C21 | 161.43 (19) |
C22—O3—C1—C2 | 5.0 (3) | C17—C16—C21—C20 | 0.2 (3) |
C3—C4—C7—O1 | −11.3 (3) | O2—C16—C21—C20 | 177.45 (19) |
C5—C4—C7—O1 | 164.5 (2) | C21—C16—C17—C18 | 0.1 (3) |
C3—C4—C7—C8 | 169.3 (2) | O2—C16—C17—C18 | −176.9 (2) |
C5—C4—C7—C8 | −14.8 (3) | C16—C17—C18—C19 | −0.6 (4) |
C15—C10—C9—C8 | −9.8 (3) | C16—C21—C20—C19 | −0.1 (3) |
C11—C10—C9—C8 | 172.8 (2) | C21—C20—C19—C18 | −0.4 (4) |
C13—C14—C15—C10 | 0.0 (3) | C17—C18—C19—C20 | 0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.94 (2) | 2.53 (2) | 3.427 (3) | 160 (2) |
C18—H18···O3ii | 0.97 (3) | 2.59 (3) | 3.432 (4) | 145 (2) |
C21—H21···Cg2iii | 0.97 (3) | 2.84 (2) | 3.548 (4) | 130 (1) |
Symmetry codes: (i) −x+2, −y−1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C21H15FO2 | C21H14F2O2 | C21H14ClFO2 | C22H17FO2 |
Mr | 318.33 | 336.32 | 352.77 | 332.36 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 290 | 290 | 290 | 290 |
a, b, c (Å) | 7.2869 (17), 5.9407 (14), 36.805 (8) | 8.164 (5), 10.036 (6), 11.136 (7) | 9.045 (6), 9.833 (6), 11.474 (7) | 9.196 (5), 9.726 (5), 11.554 (7) |
α, β, γ (°) | 90, 93.724 (4), 90 | 97.362 (10), 101.898 (9), 108.731 (9) | 99.109 (7), 104.800 (8), 113.697 (9) | 98.887 (9), 104.304 (9), 113.754 (8) |
V (Å3) | 1589.9 (6) | 826.8 (9) | 863.3 (9) | 878.2 (9) |
Z | 4 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.10 | 0.24 | 0.09 |
Crystal size (mm) | 0.56 × 0.40 × 0.24 | 0.23 × 0.20 × 0.06 | 0.14 × 0.14 × 0.13 | 0.24 × 0.14 × 0.12 |
Data collection | ||||
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.929, 0.978 | 0.944, 0.994 | 0.921, 0.969 | 0.940, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11668, 3220, 2748 | 8638, 3291, 2205 | 8889, 3395, 2672 | 9092, 3476, 2575 |
Rint | 0.017 | 0.017 | 0.025 | 0.014 |
(sin θ/λ)max (Å−1) | 0.625 | 0.625 | 0.625 | 0.625 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.135, 1.21 | 0.042, 0.118, 1.03 | 0.045, 0.134, 1.06 | 0.045, 0.124, 1.03 |
No. of reflections | 3220 | 3291 | 3395 | 3476 |
No. of parameters | 277 | 282 | 282 | 294 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.18, −0.15 | 0.12, −0.19 | 0.14, −0.17 | 0.13, −0.16 |
(V) | |
Crystal data | |
Chemical formula | C22H17FO3 |
Mr | 348.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 290 |
a, b, c (Å) | 9.645 (4), 10.111 (5), 10.537 (6) |
α, β, γ (°) | 66.706 (7), 65.347 (8), 80.949 (9) |
V (Å3) | 857.8 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.12 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.946, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8983, 3419, 2219 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.111, 1.02 |
No. of reflections | 3419 |
No. of parameters | 303 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.14, −0.17 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).
C10—C9 | 1.460 (2) | O2—C16 | 1.392 (2) |
C9—C8 | 1.327 (3) | C8—C7 | 1.475 (3) |
O1—C7 | 1.224 (2) | C4—C7 | 1.489 (2) |
O2—C12 | 1.384 (2) | ||
C8—C9—C10 | 128.00 (18) | C5—C4—C7 | 122.76 (16) |
C11—C10—C9—C8 | −176.10 (18) | C3—C4—C7—C8 | −157.94 (16) |
C10—C9—C8—C7 | −174.49 (17) | C12—O2—C16—C17 | −135.57 (19) |
C9—C8—C7—C4 | −166.65 (16) | C16—O2—C12—C11 | 60.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cg1i | 0.97 (3) | 3.02 (2) | 3.685 (2) | 127 (2) |
C14—H14···Cg2ii | 0.95 (2) | 2.77 (2) | 3.429 (2) | 128 (2) |
Symmetry codes: (i) −x+1/2, y+3/2, −z+1/2; (ii) −x+3/2, y+3/2, −z+1/2. |
C10—C9 | 1.463 (2) | C4—C7 | 1.487 (2) |
O2—C16 | 1.385 (2) | C8—C7 | 1.478 (2) |
O2—C12 | 1.3895 (19) | C7—O1 | 1.219 (2) |
C9—C8 | 1.321 (2) | ||
C8—C9—C10 | 128.49 (16) | C5—C4—C7 | 123.47 (14) |
C11—C10—C9—C8 | −167.27 (17) | C9—C8—C7—C4 | −175.44 (15) |
C16—O2—C12—C11 | 110.98 (18) | C3—C4—C7—C8 | −176.41 (14) |
C10—C9—C8—C7 | 178.70 (15) | C12—O2—C16—C17 | −18.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.95 (2) | 2.36 (2) | 3.271 (3) | 161 (2) |
C18—H18···O1ii | 0.90 (2) | 2.48 (2) | 3.345 (3) | 162 (2) |
C5—H5···Cg3iii | 0.98 (2) | 3.12 (2) | 3.894 (3) | 137 (1) |
C14—H14···Cg3iv | 0.95 (2) | 2.91 (2) | 3.780 (3) | 153 (1) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z. |
C4—C7 | 1.493 (3) | O2—C12 | 1.389 (2) |
C8—C9 | 1.328 (3) | O2—C16 | 1.391 (2) |
C8—C7 | 1.471 (3) | O1—C7 | 1.227 (2) |
C10—C9 | 1.454 (3) | ||
C5—C4—C7 | 123.88 (18) | C8—C9—C10 | 129.2 (2) |
C9—C8—C7—C4 | 177.57 (17) | C11—C10—C9—C8 | −172.6 (2) |
C3—C4—C7—C8 | −169.80 (18) | C16—O2—C12—C11 | 93.7 (2) |
C7—C8—C9—C10 | 177.47 (18) | C12—O2—C16—C17 | −14.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.96 (2) | 2.35 (2) | 3.285 (3) | 165 (2) |
C18—H18···O1ii | 0.87 (2) | 2.59 (2) | 3.381 (4) | 151 (2) |
C5—H5···Cg3iii | 0.96 (2) | 3.13 (3) | 3.940 (4) | 144 (2) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
C10—C9 | 1.464 (2) | C8—C9 | 1.324 (2) |
C4—C7 | 1.487 (2) | C8—C7 | 1.478 (2) |
O2—C16 | 1.387 (2) | C7—O1 | 1.2326 (19) |
O2—C12 | 1.3911 (19) | ||
C5—C4—C7 | 123.77 (14) | C8—C9—C10 | 128.49 (15) |
C7—C8—C9—C10 | 177.56 (13) | C3—C4—C7—C8 | −169.90 (13) |
C11—C10—C9—C8 | −174.20 (15) | C16—O2—C12—C11 | 91.19 (18) |
C9—C8—C7—C4 | 178.26 (13) | C12—O2—C16—C17 | −11.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.95 (2) | 2.35 (2) | 3.288 (3) | 167 (2) |
C18—H18···O1ii | 0.89 (2) | 2.64 (2) | 3.443 (3) | 150 (2) |
C5—H5···Cg3iii | 0.95 (2) | 3.21 (2) | 3.980 (3) | 140 (1) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
O2—C12 | 1.387 (2) | C4—C7 | 1.487 (3) |
O2—C16 | 1.392 (2) | C7—C8 | 1.479 (3) |
C10—C9 | 1.468 (3) | C9—C8 | 1.321 (3) |
O1—C7 | 1.220 (2) | ||
C5—C4—C7 | 121.99 (18) | C8—C9—C10 | 127.0 (2) |
C16—O2—C12—C11 | 115.2 (2) | C10—C9—C8—C7 | 177.1 (2) |
C3—C4—C7—C8 | 169.3 (2) | C4—C7—C8—C9 | 153.5 (2) |
C11—C10—C9—C8 | 172.8 (2) | C12—O2—C16—C17 | −21.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.94 (2) | 2.53 (2) | 3.427 (3) | 160 (2) |
C18—H18···O3ii | 0.97 (3) | 2.59 (3) | 3.432 (4) | 145 (2) |
C21—H21···Cg2iii | 0.97 (3) | 2.84 (2) | 3.548 (4) | 130 (1) |
Symmetry codes: (i) −x+2, −y−1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1. |
Compound | 1 & 2 | 2 & 3 | 1 & 3 |
I | 25.2 (1) | 20.2 (1) | 45.4 (1) |
II | 4.3 (1) | 14.2 (1) | 18.1 (1) |
III | 10.5 (1) | 6.6 (1) | 10.4 (2) |
IV | 11.1 (1) | 15.5 (3) | 10.5 (3) |
V | 23.0 (1) | 27.5 (1) | 49.1 (2) |
Notes: 1: C1–C6 2: O1/C7/C8/C9 3: C10–C15/F1. |
Compound | C8 | C9 |
I | 0.078 (2) | 0.077 (2) |
II | 0.005 (2) | -0.012 (2) |
III | 0.003 (2) | 0.024 (2) |
IV | 0.003 (2) | 0.020 (2) |
V | -0.120 (3) | 0.139 (3) |
Chalcones are an important class of organic compounds, belonging to the biogenetic precursors of the flavonoids in higher plants, and these find potential applications in widespread biological activities, viz. antibacterial, antifungal and anti-inflammatory drugs (Ahluwalia et al., 1986; Achenbach et al., 1988; Bhat et al., 1972; Masaoud et al. 1995; Mathew et al., 1984; Oganesyan et al., 1986; Sinz et al., 1999; Thuy et al., 1998). The essential feature of chalcone derivatives is the carbonyl functional group, which has a pivotal role in the observed antibacterial activity of such compounds. In addition, antimicrobial, antiviral, antitumoral, antimutagenic, antimitotic, anti-inflammatory, anti-ulcerative and hepatoprotective activities and applications of therapeutic effects have been also reported (Arty et al., 2000; Batt et al., 1993; Hu et al., 1994; Iwata et al., 1995; Lorimer & Perry, 1994; Mahmood et al.,1997; Markham et al., 1987; Min et al., 1996; Pappano et al., 1985, 1990, 1994; Sogawa et al., 1994; Williams et al., 1995). Since some chalcones are found to inhibit various enzymes, involving the reaction of reactive oxygen species (5-lipoxygenase, 12-lipoxygenase, cyclooxygenase etc.), the majority of their pharmacological properties are supposed to be related to their antioxidative effect (Forejtnikova et al., 2005; Sogawa et al., 1994). In the literature, there are reports on structure–activity correlations carried out on such classes of compounds (Debattista et al., 1986; Dhar, 1961). These compounds have also been used as starting (precursor) materials in many synthetic reactions (Awad et al., 1960; Carrie & Rochard, 1963; Coudert et al., 1988; Nel et al., 1998). Substituted chalcones have been synthesized and used as fluorescent probes (Jiang et al., 1994). In particular, chalcone derivatives with typical D-p-A mode have been reported to possess intense fluorescence properties. For example, dimethylaminochalcone (DMAC) has been reported to be a potential chemosensor (Di Cesare & Lakowicz, 2002). These have also been found to exhibit potential nonlinear optical properties (Wang & Wu, 1994; Fichou et al., 1988). Differently substituted chalcones have been investigated in detail in the solid state to understand the structural feautures associated with these compounds (Lokaj et al., 2001; Low et al., 2002; Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005), and references therein; Moorthi et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005; Ravishankar, Chinnakali, Nanjundan, Selvam & Yu, 2005; Schmalle et al., 1990; Wang et al., 2004). The phenomenon of polymorphism has also been explored in such compounds, a very important case being bavachalcone (Ravikumar et al., 2005), a bioactive compound extracted from the seed of Psoralea corylifolia, which has been widely applied for the cure of bleeding, vitiligo and psoriasis, leucoderma, bone fracture and osteoporosis (Kondo et al., 1990; Miura et al., 1996; Yin et al., 2004).
In order to understand the geometrical features and the underlying intermolecular interactions, which hold the assembly of molecules in the crystalline lattice, we have studied a series of substituted chalcones and analyzed the conformational and packing features. Weak intermolecular C—H···O, C—H···π and π–π interactions generate different packing motifs in the crystalline lattice.
Figs. 1–5 depict the structures of all the molecules. Compound (I) (Fig. 1) crystallizes in the monoclinic space group with Z = 4. Compounds (II)–(V) (Figs. 2–5) crystallize in the triclinic centrosymmetric space group. The H atom of the central propenone group is trans with respect to the C8═C9 double bond. The dihedral angles between the C10–C15/F1 and C1–C6 phenyl rings (A and B) and the dihedral angles between these rings and the O1═C7—C8═C9 group are given in Table 11. An analysis of the weighted least-squares plane through the central C4/C7/O1/C8/C9/C10 chain shows that atoms C8 and C9 are displaced by the distances given in Table 12.
The C8═C9 double-bond lengths in all of the compounds are in agreement with the expected values reported in the literature (Allen et al., 1987; Allen, 2002; Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005), and references therein; Moorthi et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005; Tables 1, 3, 5, 7 and 9). However, the C8—C9—C10 bond angle deviates from an ideal value of 120° as a result of the steric interaction between atoms H15 on ring A and H8, attached to the C8═C9 double bond (Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005), and references therein; Moorthi et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005). This is a common feature observed in all the compounds.
In (I), the intermolecular interactions that characterize the packing of molecules are C—H···π interactions involving atoms H6 and H14, forming alternate dimers in the crystalline lattice with rings A (center of gravity is denoted as Cg1) and B (center of gravity is denoted as Cg2) respectively (Fig. 6 and Table 2).
On replacement of the H atom at the para position (C1) by an F atom in (II), the electron-donating mesomeric effect of the lone pairs on the F atom on ring A leads to extended conjugation, the dihedral angle being 4.29 (8)°. The packing of molecules (Fig. 7 and Table 4) in the crystal structure is via two different types of C—H···O interaction, one forming chains along the crystallographic b axis (involving atom H18) [graph-set symbol C(12)] and the other forming dimers (involving atom H11) [graph-set symbol R22(14)]. C—H···π interactions, involving atom H14 and the C16–C21 ring (C), forming molecular chains along the a axis, further hold such molecules, leading to the formation of a sheet-like structure.
On replacement of the F atom by a Cl atom in (III), the crystal packing is unchanged. The same H atoms (H11 and H18) are involved in the formation of identical packing motifs (Fig. 8 and Table 6). Such C—H···O interactions generate tetrameric motifs, consisting of R24(32) and R24(22) units. Furthermore, C—H···π dimers, involving atom H5 and ring C, link consecutive terameric units together in the crystal structure.
Similar packing characteristics are observed in the case of the methyl derivative, (IV). Identical C—H···O and C—H···π intermolecular contacts steer the packing of molecules in the crystal structure (Fig. 9 and Table 5). In addition to these interactions, the crystal structure is further stabilized by aromatic π–π stacking interactions involving rings A and B; the distances are in the range 3.862 (3)–3.880 (3) Å in the fluoro, chloro and methyl derivatives, respectively.
In the case of (V), the presence of a methoxy group generates different packing motifs, wherein the crystal structure is stabilized by two different C—H···O dimers involving atoms H18 and H3 with atoms O3 and O1 [graph-set symbols R22(32) and R22(12)], forming dimeric motifs. Furthermore, C—H···π dimers, involving atom H21 and ring B, reinforce the existing C—H···O dimers, providing additional stability (Fig. 10 and Table 6).
It is of interest to note that the packing of molecules in all the crystal structures is dictated by weak intermolecular interactions of the C—H···O and C—H···π types.