Crystal structure of (6E,20E)-3,24-di­fluoro-13,14,28,29-tetra­hydro-5H,22H-tetra­benzo[e,j,p,u][1,4,12,15]tetra­oxa­cyclo­docosine-5,22-dione

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.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](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

---

Computing details

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).

(6E,20E)-3,24-Difluoro-13,14,28,29-tetrahydro-5H,22H-tetrabenzo[e,j,p,u] [1,4,12,15]tetraoxacyclodocosine-5,22-dione

Crystal data

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) Å^3	Block, yellow
Z = 4	0.63 × 0.29 × 0.15 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 1.1029P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Cg3 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···F2^i	0.95	2.37	3.1387 (17)	138
C15—H15···O3^ii	0.95	2.51	3.3211 (19)	143
C33—H33···F2^iii	0.95	2.53	3.483 (2)	176
C34—H34···O6^iv	0.95	2.51	3.3649 (17)	150
C36—H36···F2^i	0.95	2.43	3.3380 (19)	161
C44—H44···O1^v	0.95	2.58	3.4986 (18)	163
C46—H46···Cg3^iii	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.