The asymmetric unit of the title compound, C15H19FO4, contains two independent molecules that hydrogen bond to form dimers.
Supporting information
CCDC reference: 177217
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.113
- Data-to-parameter ratio = 13.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.02
From the CIF: _reflns_number_total 5012
Count of symmetry unique reflns 2630
Completeness (_total/calc) 190.57%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2382
Fraction of Friedel pairs measured 0.906
Are heavy atom types Z>Si present no
ALERT: MoKa measured Friedel data cannot be used to
determine absolute structure in a light-atom
study EXCEPT under VERY special conditions.
It is preferred that Friedel data is merged in such cases.
Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997), COLLECT and
maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).
(2
S)-1-(4-fluorophenyl)-2-hydroxy-2-[(2
S,5
R)-5-(1-hydroxy-1-methylethyl)- tetrahydrofuran-2-yl]ethanone
top
Crystal data top
C15H19FO4 | Dx = 1.292 Mg m−3 |
Mr = 282.30 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 23180 reflections |
a = 10.973 (2) Å | θ = 3.1–25.0° |
b = 12.764 (3) Å | µ = 0.10 mm−1 |
c = 20.721 (4) Å | T = 150 K |
V = 2902.2 (10) Å3 | Block, colourless |
Z = 8 | 0.10 × 0.10 × 0.10 mm |
F(000) = 1200 | |
Data collection top
Nonius Kappa CCD area-detector diffractometer | 2859 reflections with I > 2σ(I) |
Radiation source: Nonius FR591 Rotating anode | Rint = 0.096 |
Graphite monochromator | θmax = 25.0°, θmin = 3.1° |
Detector resolution: 9.091 pixels mm1 pixels mm-1 | h = −11→13 |
φ and ω scans to fill the Ewald sphere | k = −13→15 |
23180 measured reflections | l = −22→24 |
5012 independent reflections | |
Refinement top
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0381P)2] where P = (Fo2 + 2Fc2)/3 |
5012 reflections | (Δ/σ)max = 0.048 |
378 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
H03 | 0.281 (5) | 0.455 (3) | 0.498 (3) | 0.12 (2)* | |
H05 | 0.378 (3) | 0.433 (3) | 0.606 (2) | 0.059 (14)* | |
H07 | 0.170 (4) | 0.317 (3) | 0.524 (3) | 0.12 (2)* | |
H01 | 0.101 (8) | 0.467 (7) | 0.390 (5) | 0.29 (5)* | |
F1 | 0.9054 (2) | 0.6714 (2) | 0.35904 (15) | 0.1113 (10) | |
O1 | 0.0690 (3) | 0.4227 (3) | 0.35724 (17) | 0.0885 (9) | |
O2 | 0.3240 (2) | 0.43508 (15) | 0.37016 (13) | 0.0562 (7) | |
O3 | 0.3327 (2) | 0.4025 (2) | 0.50992 (14) | 0.0688 (8) | |
O4 | 0.3905 (2) | 0.5942 (2) | 0.48140 (15) | 0.0830 (9) | |
C1 | 0.0825 (4) | 0.3644 (3) | 0.2500 (2) | 0.0832 (14) | |
H1A | 0.0055 | 0.3993 | 0.2395 | 0.125* | |
H1B | 0.0661 | 0.2930 | 0.2650 | 0.125* | |
H1C | 0.1341 | 0.3618 | 0.2114 | 0.125* | |
C2 | 0.1712 (4) | 0.5381 (3) | 0.2822 (3) | 0.0938 (15) | |
H2A | 0.0935 | 0.5717 | 0.2716 | 0.141* | |
H2B | 0.2241 | 0.5383 | 0.2441 | 0.141* | |
H2C | 0.2109 | 0.5767 | 0.3173 | 0.141* | |
C3 | 0.1483 (3) | 0.4259 (3) | 0.3033 (2) | 0.0599 (10) | |
C4 | 0.2670 (3) | 0.3738 (2) | 0.3201 (2) | 0.0574 (10) | |
H4 | 0.3209 | 0.3735 | 0.2812 | 0.069* | |
C5 | 0.2618 (4) | 0.2636 (3) | 0.3481 (3) | 0.0923 (16) | |
H5A | 0.1799 | 0.2491 | 0.3660 | 0.111* | |
H5B | 0.2798 | 0.2110 | 0.3143 | 0.111* | |
C6 | 0.3559 (3) | 0.2594 (3) | 0.4002 (2) | 0.0666 (11) | |
H6A | 0.4189 | 0.2064 | 0.3901 | 0.080* | |
H6B | 0.3181 | 0.2418 | 0.4422 | 0.080* | |
C7 | 0.4108 (3) | 0.3688 (2) | 0.40180 (18) | 0.0525 (10) | |
H7 | 0.4882 | 0.3687 | 0.3763 | 0.063* | |
C8 | 0.4357 (3) | 0.4150 (3) | 0.46785 (19) | 0.0528 (9) | |
H8 | 0.5066 | 0.3773 | 0.4872 | 0.063* | |
C9 | 0.4672 (4) | 0.5305 (3) | 0.4633 (2) | 0.0590 (10) | |
C10 | 0.5834 (3) | 0.5647 (3) | 0.43559 (19) | 0.0531 (9) | |
C11 | 0.6798 (3) | 0.4960 (3) | 0.42333 (19) | 0.0556 (10) | |
H11 | 0.6709 | 0.4237 | 0.4332 | 0.067* | |
C12 | 0.7878 (4) | 0.5316 (3) | 0.3971 (2) | 0.0651 (11) | |
H12 | 0.8528 | 0.4847 | 0.3880 | 0.078* | |
C13 | 0.7984 (4) | 0.6350 (4) | 0.3849 (2) | 0.0742 (12) | |
C14 | 0.7092 (5) | 0.7064 (3) | 0.3978 (2) | 0.0851 (14) | |
H14 | 0.7215 | 0.7789 | 0.3897 | 0.102* | |
C15 | 0.5991 (4) | 0.6701 (3) | 0.4233 (2) | 0.0715 (12) | |
H15 | 0.5350 | 0.7180 | 0.4322 | 0.086* | |
F2 | −0.3763 (2) | 0.69292 (18) | 0.59889 (14) | 0.1072 (10) | |
O5 | 0.4228 (3) | 0.4280 (2) | 0.63817 (17) | 0.0687 (8) | |
O6 | 0.1594 (2) | 0.43280 (16) | 0.64255 (12) | 0.0544 (7) | |
O7 | 0.1263 (3) | 0.2666 (2) | 0.54482 (15) | 0.0730 (9) | |
O8 | 0.0838 (2) | 0.4567 (2) | 0.49763 (14) | 0.0752 (8) | |
C16 | 0.4304 (4) | 0.4763 (3) | 0.7483 (2) | 0.0838 (13) | |
H16A | 0.4471 | 0.4031 | 0.7596 | 0.126* | |
H16B | 0.3865 | 0.5102 | 0.7838 | 0.126* | |
H16C | 0.5075 | 0.5131 | 0.7407 | 0.126* | |
C17 | 0.3274 (4) | 0.5927 (3) | 0.6677 (3) | 0.0864 (14) | |
H17A | 0.2785 | 0.5936 | 0.6282 | 0.130* | |
H17B | 0.4047 | 0.6292 | 0.6601 | 0.130* | |
H17C | 0.2826 | 0.6281 | 0.7024 | 0.130* | |
C18 | 0.3527 (3) | 0.4802 (3) | 0.6872 (2) | 0.0569 (10) | |
C19 | 0.2337 (3) | 0.4215 (2) | 0.6987 (2) | 0.0542 (9) | |
H19 | 0.1907 | 0.4527 | 0.7367 | 0.065* | |
C20 | 0.2415 (3) | 0.3037 (2) | 0.7072 (2) | 0.0645 (11) | |
H20A | 0.3063 | 0.2735 | 0.6796 | 0.077* | |
H20B | 0.2579 | 0.2850 | 0.7527 | 0.077* | |
C21 | 0.1168 (3) | 0.2657 (3) | 0.6863 (2) | 0.0633 (11) | |
H21A | 0.0640 | 0.2528 | 0.7242 | 0.076* | |
H21B | 0.1234 | 0.2003 | 0.6609 | 0.076* | |
C22 | 0.0659 (3) | 0.3547 (2) | 0.64493 (19) | 0.0538 (9) | |
H22 | −0.0079 | 0.3846 | 0.6665 | 0.065* | |
C23 | 0.0346 (3) | 0.3272 (3) | 0.57498 (19) | 0.0567 (10) | |
H23 | −0.0425 | 0.2855 | 0.5750 | 0.068* | |
C24 | 0.0111 (3) | 0.4291 (3) | 0.5388 (2) | 0.0541 (10) | |
C25 | −0.0923 (3) | 0.4969 (3) | 0.55743 (19) | 0.0502 (9) | |
C26 | −0.2003 (3) | 0.4575 (3) | 0.58240 (19) | 0.0580 (10) | |
H26 | −0.2079 | 0.3844 | 0.5901 | 0.070* | |
C27 | −0.2960 (3) | 0.5227 (3) | 0.5961 (2) | 0.0622 (11) | |
H27 | −0.3703 | 0.4957 | 0.6127 | 0.075* | |
C28 | −0.2819 (4) | 0.6274 (3) | 0.5853 (2) | 0.0682 (12) | |
C29 | −0.1778 (4) | 0.6701 (3) | 0.5614 (2) | 0.0692 (11) | |
H29 | −0.1707 | 0.7436 | 0.5551 | 0.083* | |
C30 | −0.0824 (3) | 0.6037 (3) | 0.5466 (2) | 0.0630 (11) | |
H30 | −0.0094 | 0.6315 | 0.5288 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.102 (2) | 0.120 (2) | 0.112 (2) | −0.0515 (16) | 0.0059 (18) | 0.0066 (18) |
O1 | 0.0553 (17) | 0.139 (3) | 0.072 (2) | −0.0022 (17) | 0.0102 (18) | −0.010 (2) |
O2 | 0.0600 (16) | 0.0481 (12) | 0.0605 (18) | −0.0021 (12) | −0.0084 (13) | 0.0050 (12) |
O3 | 0.0618 (18) | 0.0861 (19) | 0.0585 (19) | 0.0050 (15) | 0.0154 (16) | 0.0016 (15) |
O4 | 0.0786 (19) | 0.0768 (17) | 0.094 (3) | 0.0223 (15) | 0.0129 (18) | −0.0191 (16) |
C1 | 0.077 (3) | 0.100 (3) | 0.073 (4) | −0.010 (2) | −0.012 (3) | −0.021 (3) |
C2 | 0.120 (4) | 0.069 (3) | 0.093 (4) | 0.001 (2) | −0.032 (3) | 0.015 (2) |
C3 | 0.056 (2) | 0.077 (3) | 0.047 (3) | −0.0027 (19) | −0.001 (2) | −0.003 (2) |
C4 | 0.057 (2) | 0.060 (2) | 0.055 (3) | −0.0079 (18) | −0.002 (2) | −0.0071 (19) |
C5 | 0.103 (4) | 0.057 (2) | 0.117 (4) | −0.009 (2) | −0.036 (3) | 0.003 (2) |
C6 | 0.068 (3) | 0.051 (2) | 0.081 (3) | 0.0061 (17) | 0.007 (3) | 0.002 (2) |
C7 | 0.046 (2) | 0.059 (2) | 0.053 (3) | 0.0054 (17) | 0.007 (2) | −0.0034 (18) |
C8 | 0.043 (2) | 0.065 (2) | 0.050 (3) | 0.0081 (17) | 0.008 (2) | 0.0024 (19) |
C9 | 0.058 (3) | 0.062 (2) | 0.057 (3) | 0.009 (2) | −0.005 (2) | −0.0032 (19) |
C10 | 0.061 (2) | 0.046 (2) | 0.052 (3) | 0.0007 (17) | −0.010 (2) | 0.0000 (17) |
C11 | 0.054 (2) | 0.053 (2) | 0.060 (3) | −0.0028 (18) | −0.010 (2) | −0.0045 (18) |
C12 | 0.059 (3) | 0.068 (2) | 0.068 (3) | −0.0102 (19) | −0.002 (2) | −0.004 (2) |
C13 | 0.066 (3) | 0.089 (3) | 0.068 (3) | −0.028 (3) | −0.006 (2) | 0.003 (2) |
C14 | 0.110 (4) | 0.059 (3) | 0.086 (4) | −0.015 (3) | −0.015 (3) | 0.009 (2) |
C15 | 0.081 (3) | 0.066 (3) | 0.067 (3) | 0.007 (2) | −0.011 (3) | 0.002 (2) |
F2 | 0.0923 (17) | 0.0889 (16) | 0.140 (3) | 0.0324 (14) | 0.0103 (19) | −0.0046 (16) |
O5 | 0.0529 (17) | 0.095 (2) | 0.058 (2) | 0.0003 (14) | 0.0054 (18) | −0.0081 (17) |
O6 | 0.0567 (15) | 0.0523 (13) | 0.0542 (18) | −0.0049 (11) | −0.0057 (14) | 0.0066 (11) |
O7 | 0.0700 (19) | 0.0668 (17) | 0.082 (2) | 0.0047 (15) | 0.0121 (18) | −0.0201 (17) |
O8 | 0.0657 (19) | 0.103 (2) | 0.057 (2) | 0.0025 (15) | 0.0132 (16) | 0.0101 (16) |
C16 | 0.066 (3) | 0.120 (3) | 0.065 (3) | −0.019 (2) | −0.012 (3) | −0.022 (3) |
C17 | 0.094 (3) | 0.063 (3) | 0.102 (4) | −0.021 (2) | 0.001 (3) | −0.007 (2) |
C18 | 0.053 (2) | 0.066 (2) | 0.052 (3) | −0.0069 (18) | 0.000 (2) | −0.015 (2) |
C19 | 0.055 (2) | 0.057 (2) | 0.051 (3) | −0.0015 (17) | −0.003 (2) | −0.0017 (18) |
C20 | 0.068 (3) | 0.067 (2) | 0.058 (3) | 0.0040 (19) | −0.009 (2) | 0.010 (2) |
C21 | 0.060 (3) | 0.055 (2) | 0.075 (3) | −0.0068 (17) | −0.003 (2) | 0.007 (2) |
C22 | 0.049 (2) | 0.052 (2) | 0.060 (3) | −0.0081 (17) | 0.004 (2) | −0.0005 (19) |
C23 | 0.046 (2) | 0.064 (2) | 0.059 (3) | −0.0068 (17) | 0.002 (2) | −0.013 (2) |
C24 | 0.048 (2) | 0.068 (2) | 0.046 (3) | −0.0114 (18) | −0.002 (2) | −0.0056 (19) |
C25 | 0.046 (2) | 0.055 (2) | 0.050 (2) | −0.0055 (16) | −0.002 (2) | 0.0001 (17) |
C26 | 0.052 (2) | 0.064 (2) | 0.058 (3) | −0.0017 (18) | 0.003 (2) | 0.0060 (19) |
C27 | 0.049 (2) | 0.074 (3) | 0.064 (3) | 0.0006 (19) | 0.003 (2) | 0.007 (2) |
C28 | 0.061 (3) | 0.073 (3) | 0.071 (3) | 0.010 (2) | 0.000 (2) | −0.003 (2) |
C29 | 0.077 (3) | 0.061 (2) | 0.070 (3) | −0.002 (2) | −0.002 (3) | 0.007 (2) |
C30 | 0.057 (2) | 0.071 (3) | 0.061 (3) | −0.009 (2) | 0.001 (2) | 0.004 (2) |
Geometric parameters (Å, º) top
F1—C13 | 1.372 (5) | F2—C28 | 1.360 (4) |
O1—C3 | 1.417 (5) | O5—C18 | 1.437 (4) |
O1—H01 | 0.95 (10) | O5—H05 | 0.83 (4) |
O2—C7 | 1.433 (4) | O6—C19 | 1.429 (4) |
O2—C4 | 1.441 (4) | O6—C22 | 1.431 (3) |
O3—C8 | 1.436 (4) | O7—C23 | 1.414 (4) |
O3—H03 | 0.91 (4) | O7—H07 | 0.91 (5) |
O4—C9 | 1.229 (4) | O8—C24 | 1.219 (4) |
C1—C3 | 1.536 (5) | C16—C18 | 1.528 (5) |
C1—H1A | 0.9800 | C16—H16A | 0.9800 |
C1—H1B | 0.9800 | C16—H16B | 0.9800 |
C1—H1C | 0.9800 | C16—H16C | 0.9800 |
C2—C3 | 1.518 (5) | C17—C18 | 1.518 (5) |
C2—H2A | 0.9800 | C17—H17A | 0.9800 |
C2—H2B | 0.9800 | C17—H17B | 0.9800 |
C2—H2C | 0.9800 | C17—H17C | 0.9800 |
C3—C4 | 1.503 (5) | C18—C19 | 1.524 (5) |
C4—C5 | 1.522 (4) | C19—C20 | 1.516 (4) |
C4—H4 | 1.0000 | C19—H19 | 1.0000 |
C5—C6 | 1.495 (5) | C20—C21 | 1.515 (5) |
C5—H5A | 0.9900 | C20—H20A | 0.9900 |
C5—H5B | 0.9900 | C20—H20B | 0.9900 |
C6—C7 | 1.521 (4) | C21—C22 | 1.528 (5) |
C6—H6A | 0.9900 | C21—H21A | 0.9900 |
C6—H6B | 0.9900 | C21—H21B | 0.9900 |
C7—C8 | 1.515 (5) | C22—C23 | 1.530 (5) |
C7—H7 | 1.0000 | C22—H22 | 1.0000 |
C8—C9 | 1.517 (5) | C23—C24 | 1.524 (5) |
C8—H8 | 1.0000 | C23—H23 | 1.0000 |
C9—C10 | 1.465 (5) | C24—C25 | 1.478 (5) |
C10—C15 | 1.380 (5) | C25—C30 | 1.386 (4) |
C10—C11 | 1.396 (5) | C25—C26 | 1.388 (4) |
C11—C12 | 1.381 (5) | C26—C27 | 1.370 (5) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C12—C13 | 1.349 (5) | C27—C28 | 1.364 (5) |
C12—H12 | 0.9500 | C27—H27 | 0.9500 |
C13—C14 | 1.364 (6) | C28—C29 | 1.359 (5) |
C14—C15 | 1.397 (6) | C29—C30 | 1.381 (5) |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C15—H15 | 0.9500 | C30—H30 | 0.9500 |
| | | |
C3—O1—H01 | 108 (6) | C18—O5—H05 | 102 (3) |
C7—O2—C4 | 107.3 (2) | C19—O6—C22 | 108.1 (3) |
C8—O3—H03 | 105 (4) | C23—O7—H07 | 102 (3) |
C3—C1—H1A | 109.5 | C18—C16—H16A | 109.5 |
C3—C1—H1B | 109.5 | C18—C16—H16B | 109.5 |
H1A—C1—H1B | 109.5 | H16A—C16—H16B | 109.5 |
C3—C1—H1C | 109.5 | C18—C16—H16C | 109.5 |
H1A—C1—H1C | 109.5 | H16A—C16—H16C | 109.5 |
H1B—C1—H1C | 109.5 | H16B—C16—H16C | 109.5 |
C3—C2—H2A | 109.5 | C18—C17—H17A | 109.5 |
C3—C2—H2B | 109.5 | C18—C17—H17B | 109.5 |
H2A—C2—H2B | 109.5 | H17A—C17—H17B | 109.5 |
C3—C2—H2C | 109.5 | C18—C17—H17C | 109.5 |
H2A—C2—H2C | 109.5 | H17A—C17—H17C | 109.5 |
H2B—C2—H2C | 109.5 | H17B—C17—H17C | 109.5 |
O1—C3—C4 | 109.7 (3) | O5—C18—C17 | 110.4 (4) |
O1—C3—C2 | 110.9 (4) | O5—C18—C19 | 110.0 (3) |
C4—C3—C2 | 109.9 (3) | C17—C18—C19 | 110.5 (3) |
O1—C3—C1 | 105.3 (3) | O5—C18—C16 | 105.8 (3) |
C4—C3—C1 | 110.3 (3) | C17—C18—C16 | 110.7 (3) |
C2—C3—C1 | 110.6 (4) | C19—C18—C16 | 109.4 (3) |
O2—C4—C3 | 107.6 (3) | O6—C19—C20 | 103.1 (3) |
O2—C4—C5 | 104.1 (3) | O6—C19—C18 | 108.1 (3) |
C3—C4—C5 | 117.7 (3) | C20—C19—C18 | 117.2 (3) |
O2—C4—H4 | 109.1 | O6—C19—H19 | 109.4 |
C3—C4—H4 | 109.1 | C20—C19—H19 | 109.4 |
C5—C4—H4 | 109.1 | C18—C19—H19 | 109.4 |
C6—C5—C4 | 106.4 (3) | C21—C20—C19 | 103.4 (3) |
C6—C5—H5A | 110.4 | C21—C20—H20A | 111.1 |
C4—C5—H5A | 110.4 | C19—C20—H20A | 111.1 |
C6—C5—H5B | 110.4 | C21—C20—H20B | 111.1 |
C4—C5—H5B | 110.4 | C19—C20—H20B | 111.1 |
H5A—C5—H5B | 108.6 | H20A—C20—H20B | 109.0 |
C5—C6—C7 | 104.8 (3) | C20—C21—C22 | 104.7 (3) |
C5—C6—H6A | 110.8 | C20—C21—H21A | 110.8 |
C7—C6—H6A | 110.8 | C22—C21—H21A | 110.8 |
C5—C6—H6B | 110.8 | C20—C21—H21B | 110.8 |
C7—C6—H6B | 110.8 | C22—C21—H21B | 110.8 |
H6A—C6—H6B | 108.9 | H21A—C21—H21B | 108.9 |
O2—C7—C8 | 107.6 (3) | O6—C22—C21 | 106.0 (3) |
O2—C7—C6 | 105.6 (3) | O6—C22—C23 | 106.7 (3) |
C8—C7—C6 | 116.6 (3) | C21—C22—C23 | 116.3 (3) |
O2—C7—H7 | 108.9 | O6—C22—H22 | 109.2 |
C8—C7—H7 | 108.9 | C21—C22—H22 | 109.2 |
C6—C7—H7 | 108.9 | C23—C22—H22 | 109.2 |
O3—C8—C7 | 111.3 (3) | O7—C23—C24 | 111.7 (3) |
O3—C8—C9 | 109.0 (3) | O7—C23—C22 | 112.6 (3) |
C7—C8—C9 | 111.3 (3) | C24—C23—C22 | 108.0 (3) |
O3—C8—H8 | 108.4 | O7—C23—H23 | 108.1 |
C7—C8—H8 | 108.4 | C24—C23—H23 | 108.1 |
C9—C8—H8 | 108.4 | C22—C23—H23 | 108.1 |
O4—C9—C10 | 121.3 (3) | O8—C24—C25 | 121.1 (3) |
O4—C9—C8 | 117.9 (3) | O8—C24—C23 | 118.7 (3) |
C10—C9—C8 | 120.8 (3) | C25—C24—C23 | 120.1 (3) |
C15—C10—C11 | 118.9 (4) | C30—C25—C26 | 119.0 (3) |
C15—C10—C9 | 118.1 (3) | C30—C25—C24 | 118.2 (3) |
C11—C10—C9 | 123.0 (3) | C26—C25—C24 | 122.7 (3) |
C12—C11—C10 | 121.0 (3) | C27—C26—C25 | 120.7 (3) |
C12—C11—H11 | 119.5 | C27—C26—H26 | 119.6 |
C10—C11—H11 | 119.5 | C25—C26—H26 | 119.6 |
C13—C12—C11 | 118.0 (4) | C28—C27—C26 | 118.3 (3) |
C13—C12—H12 | 121.0 | C28—C27—H27 | 120.8 |
C11—C12—H12 | 121.0 | C26—C27—H27 | 120.8 |
C12—C13—C14 | 123.7 (4) | C29—C28—F2 | 118.0 (4) |
C12—C13—F1 | 118.5 (4) | C29—C28—C27 | 123.2 (4) |
C14—C13—F1 | 117.7 (4) | F2—C28—C27 | 118.8 (4) |
C13—C14—C15 | 118.3 (4) | C28—C29—C30 | 118.2 (4) |
C13—C14—H14 | 120.9 | C28—C29—H29 | 120.9 |
C15—C14—H14 | 120.9 | C30—C29—H29 | 120.9 |
C10—C15—C14 | 120.0 (4) | C29—C30—C25 | 120.5 (3) |
C10—C15—H15 | 120.0 | C29—C30—H30 | 119.7 |
C14—C15—H15 | 120.0 | C25—C30—H30 | 119.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H05···O3 | 0.83 (4) | 2.09 (4) | 2.854 (5) | 153 (3) |
O7—H07···O3 | 0.91 (5) | 2.11 (4) | 2.943 (4) | 150 (4) |
O1—H01···O8 | 0.95 (10) | 2.25 (11) | 2.946 (5) | 130 (7) |
O3—H03···O8 | 0.93 (8) | 2.17 (9) | 2.831 (5) | 127 (6) |