The conformation of the title compound is cone-shaped, partially determined by short intramolecular C—H
O contacts. In the crystal, molecules are linked
via C—H
O and C—H
F hydrogen bonds and C—H
π interactions, forming a three-dimensional supramolecular structure.
Supporting information
CCDC reference: 1519443
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.106
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.538 Report
Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.63 mm
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES ......... 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 18 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT2014/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b) and PLATON (Spek, 2009).
(6
E,20
E)-3,24-Difluoro-13,14,28,29-tetrahydro-5
H,22
H-tetrabenzo[
e,
j,
p,
u]
[1,4,12,15]tetraoxacyclodocosine-5,22-dione
top
Crystal data top
C34H26F2O6 | F(000) = 1184 |
Mr = 568.55 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.2618 (7) Å | Cell parameters from 9878 reflections |
b = 11.6708 (5) Å | θ = 2.5–28.2° |
c = 14.7359 (7) Å | µ = 0.10 mm−1 |
β = 96.945 (2)° | T = 200 K |
V = 2776.2 (2) Å3 | Block, yellow |
Z = 4 | 0.63 × 0.29 × 0.15 mm |
Data collection top
Bruker APEXII CCD diffractometer | 6911 independent reflections |
Radiation source: sealed tube | 5302 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
φ and ω scans | h = −21→20 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −15→15 |
Tmin = 0.894, Tmax = 1.000 | l = −19→19 |
38582 measured 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0392P)2 + 1.1029P] where P = (Fo2 + 2Fc2)/3 |
6911 reflections | (Δ/σ)max < 0.001 |
379 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | −0.00518 (7) | −0.16078 (10) | 0.73153 (8) | 0.0712 (3) | |
F2 | 0.30286 (7) | 0.77217 (11) | 0.36051 (9) | 0.0823 (4) | |
O1 | 0.07789 (6) | 0.21042 (8) | 0.53657 (8) | 0.0426 (2) | |
O2 | 0.12188 (7) | 0.44266 (9) | 0.50741 (7) | 0.0479 (3) | |
O3 | 0.13697 (6) | 0.63181 (11) | 0.65378 (8) | 0.0567 (3) | |
O4 | 0.45695 (6) | 0.39443 (9) | 0.59069 (6) | 0.0389 (2) | |
O5 | 0.41025 (6) | 0.24383 (8) | 0.44309 (6) | 0.0365 (2) | |
O6 | 0.23814 (6) | −0.05205 (9) | 0.57921 (8) | 0.0473 (3) | |
C1 | 0.02059 (8) | 0.30158 (12) | 0.51429 (11) | 0.0423 (3) | |
H1A | 0.0096 | 0.3429 | 0.5703 | 0.051* | |
H1B | −0.0325 | 0.2714 | 0.4835 | 0.051* | |
C2 | 0.05993 (9) | 0.37973 (13) | 0.45186 (11) | 0.0433 (3) | |
H2A | 0.0851 | 0.3349 | 0.4053 | 0.052* | |
H2B | 0.0181 | 0.4324 | 0.4202 | 0.052* | |
C3 | 0.20104 (8) | 0.60305 (12) | 0.62506 (10) | 0.0376 (3) | |
C4 | 0.27425 (8) | 0.57029 (12) | 0.68694 (10) | 0.0388 (3) | |
H4 | 0.2730 | 0.5805 | 0.7507 | 0.047* | |
C5 | 0.34280 (8) | 0.52688 (11) | 0.65906 (9) | 0.0335 (3) | |
H5 | 0.3429 | 0.5177 | 0.5950 | 0.040* | |
C6 | 0.51460 (8) | 0.32791 (12) | 0.54755 (10) | 0.0368 (3) | |
H6A | 0.5213 | 0.2511 | 0.5760 | 0.044* | |
H6B | 0.5693 | 0.3661 | 0.5535 | 0.044* | |
C7 | 0.48031 (8) | 0.31774 (12) | 0.44922 (9) | 0.0372 (3) | |
H7A | 0.4638 | 0.3942 | 0.4242 | 0.045* | |
H7B | 0.5228 | 0.2859 | 0.4135 | 0.045* | |
C8 | 0.26989 (8) | 0.11337 (11) | 0.44357 (9) | 0.0337 (3) | |
H8 | 0.3169 | 0.0888 | 0.4834 | 0.040* | |
C9 | 0.19546 (8) | 0.08387 (12) | 0.46483 (9) | 0.0352 (3) | |
H9 | 0.1477 | 0.1089 | 0.4264 | 0.042* | |
C10 | 0.18427 (8) | 0.01401 (11) | 0.54551 (9) | 0.0336 (3) | |
C11 | 0.05441 (8) | 0.11931 (11) | 0.58468 (9) | 0.0341 (3) | |
C12 | 0.10509 (8) | 0.02187 (11) | 0.58816 (9) | 0.0321 (3) | |
C13 | 0.08374 (9) | −0.07270 (12) | 0.63846 (10) | 0.0387 (3) | |
H13 | 0.1166 | −0.1402 | 0.6413 | 0.046* | |
C14 | 0.01517 (10) | −0.06726 (14) | 0.68353 (10) | 0.0454 (4) | |
C15 | −0.03344 (9) | 0.02861 (14) | 0.68325 (11) | 0.0468 (4) | |
H15 | −0.0795 | 0.0305 | 0.7173 | 0.056* | |
C16 | −0.01442 (9) | 0.12229 (13) | 0.63273 (10) | 0.0421 (3) | |
H16 | −0.0482 | 0.1889 | 0.6306 | 0.050* | |
C21 | 0.16576 (9) | 0.52274 (13) | 0.46597 (10) | 0.0399 (3) | |
C22 | 0.20682 (8) | 0.60381 (12) | 0.52387 (10) | 0.0352 (3) | |
C23 | 0.25285 (8) | 0.68864 (13) | 0.48752 (12) | 0.0452 (4) | |
H23 | 0.2808 | 0.7455 | 0.5257 | 0.054* | |
C24 | 0.25707 (9) | 0.68851 (16) | 0.39503 (13) | 0.0559 (5) | |
C25 | 0.21969 (11) | 0.6085 (2) | 0.33750 (12) | 0.0684 (6) | |
H25 | 0.2256 | 0.6099 | 0.2742 | 0.082* | |
C26 | 0.17280 (11) | 0.52466 (18) | 0.37308 (11) | 0.0607 (5) | |
H26 | 0.1454 | 0.4683 | 0.3339 | 0.073* | |
C31 | 0.41776 (8) | 0.49208 (11) | 0.71727 (9) | 0.0329 (3) | |
C32 | 0.47646 (8) | 0.42363 (11) | 0.68041 (9) | 0.0332 (3) | |
C33 | 0.54911 (8) | 0.39044 (13) | 0.73364 (10) | 0.0393 (3) | |
H33 | 0.5881 | 0.3429 | 0.7085 | 0.047* | |
C34 | 0.56427 (9) | 0.42722 (14) | 0.82355 (10) | 0.0442 (3) | |
H34 | 0.6142 | 0.4056 | 0.8597 | 0.053* | |
C35 | 0.50782 (10) | 0.49464 (14) | 0.86091 (10) | 0.0455 (4) | |
H35 | 0.5188 | 0.5196 | 0.9225 | 0.055* | |
C36 | 0.43489 (9) | 0.52605 (13) | 0.80844 (10) | 0.0409 (3) | |
H36 | 0.3957 | 0.5716 | 0.8350 | 0.049* | |
C41 | 0.35808 (8) | 0.24427 (11) | 0.36284 (9) | 0.0333 (3) | |
C42 | 0.28472 (8) | 0.18095 (11) | 0.36335 (9) | 0.0337 (3) | |
C43 | 0.22821 (9) | 0.18261 (13) | 0.28370 (10) | 0.0429 (3) | |
H43 | 0.1776 | 0.1418 | 0.2828 | 0.051* | |
C44 | 0.24391 (10) | 0.24171 (15) | 0.20655 (11) | 0.0503 (4) | |
H44 | 0.2045 | 0.2416 | 0.1534 | 0.060* | |
C45 | 0.31735 (11) | 0.30101 (14) | 0.20740 (11) | 0.0501 (4) | |
H45 | 0.3289 | 0.3408 | 0.1542 | 0.060* | |
C46 | 0.37440 (9) | 0.30306 (13) | 0.28523 (10) | 0.0419 (3) | |
H46 | 0.4246 | 0.3447 | 0.2854 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0696 (7) | 0.0713 (7) | 0.0754 (7) | −0.0146 (6) | 0.0193 (6) | 0.0290 (6) |
F2 | 0.0549 (6) | 0.0891 (8) | 0.1024 (9) | −0.0128 (6) | 0.0076 (6) | 0.0586 (7) |
O1 | 0.0308 (5) | 0.0332 (5) | 0.0649 (7) | 0.0023 (4) | 0.0108 (4) | 0.0063 (5) |
O2 | 0.0516 (6) | 0.0491 (6) | 0.0411 (6) | −0.0208 (5) | −0.0019 (5) | 0.0028 (5) |
O3 | 0.0340 (5) | 0.0756 (8) | 0.0623 (7) | 0.0065 (5) | 0.0129 (5) | −0.0085 (6) |
O4 | 0.0311 (5) | 0.0489 (6) | 0.0351 (5) | 0.0073 (4) | −0.0020 (4) | −0.0084 (4) |
O5 | 0.0345 (5) | 0.0411 (5) | 0.0330 (5) | −0.0087 (4) | 0.0010 (4) | −0.0006 (4) |
O6 | 0.0344 (5) | 0.0437 (6) | 0.0630 (7) | 0.0062 (4) | 0.0029 (5) | 0.0083 (5) |
C1 | 0.0292 (6) | 0.0323 (7) | 0.0637 (10) | 0.0012 (5) | −0.0018 (6) | −0.0020 (6) |
C2 | 0.0398 (7) | 0.0360 (7) | 0.0506 (8) | −0.0017 (6) | −0.0087 (6) | −0.0006 (6) |
C3 | 0.0306 (6) | 0.0341 (7) | 0.0485 (8) | −0.0021 (5) | 0.0063 (6) | −0.0064 (6) |
C4 | 0.0370 (7) | 0.0429 (8) | 0.0363 (7) | −0.0010 (6) | 0.0031 (5) | −0.0087 (6) |
C5 | 0.0341 (6) | 0.0335 (7) | 0.0324 (6) | −0.0010 (5) | 0.0019 (5) | −0.0022 (5) |
C6 | 0.0268 (6) | 0.0379 (7) | 0.0453 (8) | 0.0013 (5) | 0.0021 (5) | −0.0061 (6) |
C7 | 0.0329 (6) | 0.0390 (7) | 0.0408 (7) | −0.0060 (6) | 0.0087 (5) | −0.0057 (6) |
C8 | 0.0298 (6) | 0.0342 (7) | 0.0361 (7) | −0.0005 (5) | 0.0003 (5) | −0.0046 (5) |
C9 | 0.0303 (6) | 0.0383 (7) | 0.0364 (7) | 0.0015 (5) | 0.0009 (5) | −0.0041 (6) |
C10 | 0.0275 (6) | 0.0322 (6) | 0.0401 (7) | −0.0028 (5) | −0.0008 (5) | −0.0046 (5) |
C11 | 0.0288 (6) | 0.0327 (6) | 0.0401 (7) | −0.0067 (5) | 0.0013 (5) | −0.0045 (5) |
C12 | 0.0274 (6) | 0.0345 (7) | 0.0331 (6) | −0.0046 (5) | −0.0013 (5) | −0.0036 (5) |
C13 | 0.0373 (7) | 0.0374 (7) | 0.0393 (7) | −0.0058 (6) | −0.0032 (6) | 0.0012 (6) |
C14 | 0.0448 (8) | 0.0500 (9) | 0.0410 (8) | −0.0150 (7) | 0.0034 (6) | 0.0065 (7) |
C15 | 0.0398 (8) | 0.0572 (9) | 0.0453 (8) | −0.0138 (7) | 0.0129 (6) | −0.0087 (7) |
C16 | 0.0338 (7) | 0.0408 (8) | 0.0524 (9) | −0.0051 (6) | 0.0086 (6) | −0.0122 (6) |
C21 | 0.0343 (7) | 0.0443 (8) | 0.0395 (7) | −0.0034 (6) | −0.0021 (6) | 0.0082 (6) |
C22 | 0.0248 (6) | 0.0350 (7) | 0.0451 (7) | 0.0041 (5) | 0.0016 (5) | 0.0059 (6) |
C23 | 0.0299 (7) | 0.0387 (8) | 0.0661 (10) | 0.0003 (6) | 0.0020 (6) | 0.0107 (7) |
C24 | 0.0336 (7) | 0.0656 (11) | 0.0672 (11) | −0.0028 (7) | 0.0011 (7) | 0.0377 (9) |
C25 | 0.0500 (10) | 0.1086 (16) | 0.0438 (9) | −0.0169 (10) | −0.0062 (7) | 0.0300 (10) |
C26 | 0.0565 (10) | 0.0842 (13) | 0.0384 (8) | −0.0195 (9) | −0.0065 (7) | 0.0085 (8) |
C31 | 0.0329 (6) | 0.0339 (6) | 0.0314 (6) | −0.0037 (5) | 0.0021 (5) | 0.0016 (5) |
C32 | 0.0317 (6) | 0.0343 (7) | 0.0326 (6) | −0.0045 (5) | −0.0002 (5) | 0.0012 (5) |
C33 | 0.0315 (6) | 0.0422 (8) | 0.0426 (8) | −0.0012 (6) | −0.0016 (5) | 0.0035 (6) |
C34 | 0.0383 (7) | 0.0506 (9) | 0.0405 (8) | −0.0078 (6) | −0.0084 (6) | 0.0112 (7) |
C35 | 0.0506 (8) | 0.0539 (9) | 0.0304 (7) | −0.0085 (7) | −0.0025 (6) | 0.0022 (6) |
C36 | 0.0441 (8) | 0.0448 (8) | 0.0337 (7) | −0.0022 (6) | 0.0038 (6) | −0.0022 (6) |
C41 | 0.0344 (6) | 0.0337 (6) | 0.0315 (6) | 0.0026 (5) | 0.0029 (5) | −0.0031 (5) |
C42 | 0.0332 (6) | 0.0338 (7) | 0.0340 (7) | 0.0021 (5) | 0.0033 (5) | −0.0037 (5) |
C43 | 0.0355 (7) | 0.0469 (8) | 0.0442 (8) | −0.0007 (6) | −0.0036 (6) | −0.0021 (6) |
C44 | 0.0521 (9) | 0.0539 (9) | 0.0411 (8) | 0.0043 (8) | −0.0105 (7) | 0.0036 (7) |
C45 | 0.0602 (10) | 0.0506 (9) | 0.0383 (8) | 0.0006 (8) | 0.0010 (7) | 0.0085 (7) |
C46 | 0.0438 (8) | 0.0429 (8) | 0.0392 (7) | −0.0038 (6) | 0.0055 (6) | 0.0021 (6) |
Geometric parameters (Å, º) top
F1—C14 | 1.3628 (18) | C12—C13 | 1.3966 (19) |
F2—C24 | 1.3632 (18) | C13—C14 | 1.367 (2) |
O1—C11 | 1.3581 (16) | C13—H13 | 0.9500 |
O1—C1 | 1.4262 (16) | C14—C15 | 1.370 (2) |
O2—C21 | 1.3643 (17) | C15—C16 | 1.379 (2) |
O2—C2 | 1.4230 (17) | C15—H15 | 0.9500 |
O3—C3 | 1.2183 (16) | C16—H16 | 0.9500 |
O4—C32 | 1.3651 (16) | C21—C26 | 1.388 (2) |
O4—C6 | 1.4247 (16) | C21—C22 | 1.390 (2) |
O5—C41 | 1.3695 (15) | C22—C23 | 1.387 (2) |
O5—C7 | 1.4231 (15) | C23—C24 | 1.373 (2) |
O6—C10 | 1.2261 (16) | C23—H23 | 0.9500 |
C1—C2 | 1.493 (2) | C24—C25 | 1.355 (3) |
C1—H1A | 0.9900 | C25—C26 | 1.382 (3) |
C1—H1B | 0.9900 | C25—H25 | 0.9500 |
C2—H2A | 0.9900 | C26—H26 | 0.9500 |
C2—H2B | 0.9900 | C31—C36 | 1.3962 (19) |
C3—C4 | 1.460 (2) | C31—C32 | 1.4035 (19) |
C3—C22 | 1.505 (2) | C32—C33 | 1.3918 (18) |
C4—C5 | 1.3338 (19) | C33—C34 | 1.386 (2) |
C4—H4 | 0.9500 | C33—H33 | 0.9500 |
C5—C31 | 1.4608 (18) | C34—C35 | 1.374 (2) |
C5—H5 | 0.9500 | C34—H34 | 0.9500 |
C6—C7 | 1.4931 (19) | C35—C36 | 1.385 (2) |
C6—H6A | 0.9900 | C35—H35 | 0.9500 |
C6—H6B | 0.9900 | C36—H36 | 0.9500 |
C7—H7A | 0.9900 | C41—C46 | 1.3867 (19) |
C7—H7B | 0.9900 | C41—C42 | 1.4041 (18) |
C8—C9 | 1.3317 (18) | C42—C43 | 1.4006 (19) |
C8—C42 | 1.4652 (19) | C43—C44 | 1.380 (2) |
C8—H8 | 0.9500 | C43—H43 | 0.9500 |
C9—C10 | 1.471 (2) | C44—C45 | 1.379 (2) |
C9—H9 | 0.9500 | C44—H44 | 0.9500 |
C10—C12 | 1.5022 (18) | C45—C46 | 1.385 (2) |
C11—C16 | 1.3955 (19) | C45—H45 | 0.9500 |
C11—C12 | 1.4017 (19) | C46—H46 | 0.9500 |
| | | |
C11—O1—C1 | 119.15 (11) | C14—C15—H15 | 120.6 |
C21—O2—C2 | 117.92 (11) | C16—C15—H15 | 120.6 |
C32—O4—C6 | 118.67 (10) | C15—C16—C11 | 120.02 (14) |
C41—O5—C7 | 117.40 (10) | C15—C16—H16 | 120.0 |
O1—C1—C2 | 106.30 (11) | C11—C16—H16 | 120.0 |
O1—C1—H1A | 110.5 | O2—C21—C26 | 124.24 (14) |
C2—C1—H1A | 110.5 | O2—C21—C22 | 115.48 (12) |
O1—C1—H1B | 110.5 | C26—C21—C22 | 120.25 (14) |
C2—C1—H1B | 110.5 | C23—C22—C21 | 119.38 (14) |
H1A—C1—H1B | 108.7 | C23—C22—C3 | 119.20 (13) |
O2—C2—C1 | 106.68 (12) | C21—C22—C3 | 121.41 (12) |
O2—C2—H2A | 110.4 | C24—C23—C22 | 118.46 (15) |
C1—C2—H2A | 110.4 | C24—C23—H23 | 120.8 |
O2—C2—H2B | 110.4 | C22—C23—H23 | 120.8 |
C1—C2—H2B | 110.4 | C25—C24—F2 | 118.96 (17) |
H2A—C2—H2B | 108.6 | C25—C24—C23 | 123.32 (15) |
O3—C3—C4 | 121.47 (14) | F2—C24—C23 | 117.70 (17) |
O3—C3—C22 | 120.06 (13) | C24—C25—C26 | 118.48 (17) |
C4—C3—C22 | 118.44 (12) | C24—C25—H25 | 120.8 |
C5—C4—C3 | 123.76 (13) | C26—C25—H25 | 120.8 |
C5—C4—H4 | 118.1 | C25—C26—C21 | 120.06 (17) |
C3—C4—H4 | 118.1 | C25—C26—H26 | 120.0 |
C4—C5—C31 | 126.44 (13) | C21—C26—H26 | 120.0 |
C4—C5—H5 | 116.8 | C36—C31—C32 | 117.91 (12) |
C31—C5—H5 | 116.8 | C36—C31—C5 | 122.77 (13) |
O4—C6—C7 | 106.72 (10) | C32—C31—C5 | 119.30 (12) |
O4—C6—H6A | 110.4 | O4—C32—C33 | 123.95 (12) |
C7—C6—H6A | 110.4 | O4—C32—C31 | 115.31 (11) |
O4—C6—H6B | 110.4 | C33—C32—C31 | 120.74 (12) |
C7—C6—H6B | 110.4 | C34—C33—C32 | 119.55 (14) |
H6A—C6—H6B | 108.6 | C34—C33—H33 | 120.2 |
O5—C7—C6 | 108.18 (11) | C32—C33—H33 | 120.2 |
O5—C7—H7A | 110.1 | C35—C34—C33 | 120.69 (13) |
C6—C7—H7A | 110.1 | C35—C34—H34 | 119.7 |
O5—C7—H7B | 110.1 | C33—C34—H34 | 119.7 |
C6—C7—H7B | 110.1 | C34—C35—C36 | 119.78 (14) |
H7A—C7—H7B | 108.4 | C34—C35—H35 | 120.1 |
C9—C8—C42 | 124.89 (12) | C36—C35—H35 | 120.1 |
C9—C8—H8 | 117.6 | C35—C36—C31 | 121.33 (14) |
C42—C8—H8 | 117.6 | C35—C36—H36 | 119.3 |
C8—C9—C10 | 122.56 (12) | C31—C36—H36 | 119.3 |
C8—C9—H9 | 118.7 | O5—C41—C46 | 123.62 (12) |
C10—C9—H9 | 118.7 | O5—C41—C42 | 115.56 (11) |
O6—C10—C9 | 121.58 (12) | C46—C41—C42 | 120.82 (12) |
O6—C10—C12 | 118.40 (12) | C43—C42—C41 | 117.39 (13) |
C9—C10—C12 | 120.02 (11) | C43—C42—C8 | 121.89 (12) |
O1—C11—C16 | 122.60 (13) | C41—C42—C8 | 120.70 (12) |
O1—C11—C12 | 116.94 (11) | C44—C43—C42 | 121.96 (14) |
C16—C11—C12 | 120.39 (13) | C44—C43—H43 | 119.0 |
C13—C12—C11 | 118.54 (12) | C42—C43—H43 | 119.0 |
C13—C12—C10 | 117.03 (12) | C45—C44—C43 | 119.33 (14) |
C11—C12—C10 | 124.34 (12) | C45—C44—H44 | 120.3 |
C14—C13—C12 | 119.41 (14) | C43—C44—H44 | 120.3 |
C14—C13—H13 | 120.3 | C44—C45—C46 | 120.58 (15) |
C12—C13—H13 | 120.3 | C44—C45—H45 | 119.7 |
F1—C14—C13 | 118.59 (15) | C46—C45—H45 | 119.7 |
F1—C14—C15 | 118.66 (14) | C45—C46—C41 | 119.89 (14) |
C13—C14—C15 | 122.75 (14) | C45—C46—H46 | 120.1 |
C14—C15—C16 | 118.84 (14) | C41—C46—H46 | 120.1 |
| | | |
C11—O1—C1—C2 | −172.73 (12) | C4—C3—C22—C21 | 109.61 (15) |
C21—O2—C2—C1 | −178.45 (12) | C21—C22—C23—C24 | −0.8 (2) |
O1—C1—C2—O2 | −75.81 (14) | C3—C22—C23—C24 | −179.61 (13) |
O3—C3—C4—C5 | 172.72 (15) | C22—C23—C24—C25 | −1.2 (2) |
C22—C3—C4—C5 | −8.9 (2) | C22—C23—C24—F2 | −179.71 (13) |
C3—C4—C5—C31 | −179.75 (13) | F2—C24—C25—C26 | −179.42 (17) |
C32—O4—C6—C7 | −175.40 (11) | C23—C24—C25—C26 | 2.1 (3) |
C41—O5—C7—C6 | 164.74 (11) | C24—C25—C26—C21 | −0.9 (3) |
O4—C6—C7—O5 | −71.01 (14) | O2—C21—C26—C25 | −179.07 (16) |
C42—C8—C9—C10 | 178.86 (12) | C22—C21—C26—C25 | −1.0 (3) |
C8—C9—C10—O6 | −25.3 (2) | C4—C5—C31—C36 | −16.4 (2) |
C8—C9—C10—C12 | 155.24 (13) | C4—C5—C31—C32 | 165.00 (14) |
C1—O1—C11—C16 | −16.33 (19) | C6—O4—C32—C33 | −1.32 (19) |
C1—O1—C11—C12 | 166.75 (12) | C6—O4—C32—C31 | 178.13 (12) |
O1—C11—C12—C13 | 178.80 (11) | C36—C31—C32—O4 | −179.10 (12) |
C16—C11—C12—C13 | 1.80 (19) | C5—C31—C32—O4 | −0.44 (18) |
O1—C11—C12—C10 | 2.40 (19) | C36—C31—C32—C33 | 0.4 (2) |
C16—C11—C12—C10 | −174.60 (12) | C5—C31—C32—C33 | 179.02 (12) |
O6—C10—C12—C13 | −23.85 (18) | O4—C32—C33—C34 | 178.22 (13) |
C9—C10—C12—C13 | 155.65 (12) | C31—C32—C33—C34 | −1.2 (2) |
O6—C10—C12—C11 | 152.60 (13) | C32—C33—C34—C35 | 0.9 (2) |
C9—C10—C12—C11 | −27.90 (18) | C33—C34—C35—C36 | 0.2 (2) |
C11—C12—C13—C14 | −0.82 (19) | C34—C35—C36—C31 | −1.0 (2) |
C10—C12—C13—C14 | 175.85 (12) | C32—C31—C36—C35 | 0.8 (2) |
C12—C13—C14—F1 | 179.36 (13) | C5—C31—C36—C35 | −177.86 (14) |
C12—C13—C14—C15 | −1.3 (2) | C7—O5—C41—C46 | 6.93 (19) |
F1—C14—C15—C16 | −178.23 (13) | C7—O5—C41—C42 | −172.61 (11) |
C13—C14—C15—C16 | 2.5 (2) | O5—C41—C42—C43 | 177.69 (12) |
C14—C15—C16—C11 | −1.4 (2) | C46—C41—C42—C43 | −1.9 (2) |
O1—C11—C16—C15 | −177.51 (13) | O5—C41—C42—C8 | −4.12 (18) |
C12—C11—C16—C15 | −0.7 (2) | C46—C41—C42—C8 | 176.32 (13) |
C2—O2—C21—C26 | −20.2 (2) | C9—C8—C42—C43 | −26.3 (2) |
C2—O2—C21—C22 | 161.70 (13) | C9—C8—C42—C41 | 155.60 (13) |
O2—C21—C22—C23 | −179.87 (12) | C41—C42—C43—C44 | 1.4 (2) |
C26—C21—C22—C23 | 1.9 (2) | C8—C42—C43—C44 | −176.79 (14) |
O2—C21—C22—C3 | −1.14 (19) | C42—C43—C44—C45 | 0.1 (2) |
C26—C21—C22—C3 | −179.34 (15) | C43—C44—C45—C46 | −1.0 (3) |
O3—C3—C22—C23 | 106.71 (16) | C44—C45—C46—C41 | 0.6 (2) |
C4—C3—C22—C23 | −71.66 (17) | O5—C41—C46—C45 | −178.58 (14) |
O3—C3—C22—C21 | −72.03 (19) | C42—C41—C46—C45 | 0.9 (2) |
Hydrogen-bond geometry (Å, º) topCg3 is the centroid of the C31–C36 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O4 | 0.95 | 2.35 | 2.7023 (16) | 101 |
C9—H9···O1 | 0.95 | 2.40 | 2.7281 (16) | 100 |
C4—H4···F2i | 0.95 | 2.37 | 3.1387 (17) | 138 |
C15—H15···O3ii | 0.95 | 2.51 | 3.3211 (19) | 143 |
C33—H33···F2iii | 0.95 | 2.53 | 3.483 (2) | 176 |
C34—H34···O6iv | 0.95 | 2.51 | 3.3649 (17) | 150 |
C36—H36···F2i | 0.95 | 2.43 | 3.3380 (19) | 161 |
C44—H44···O1v | 0.95 | 2.58 | 3.4986 (18) | 163 |
C46—H46···Cg3iii | 0.95 | 2.84 | 3.6829 (16) | 149 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y+1/2, −z+3/2; (v) x, −y+1/2, z−1/2. |