Ethyl 1,3,10,12-tetra-phenyl-19,20-dioxa-hexa-cyclo-[10.6.1.1.0.0.0]icosa-4(9),5,7,13(18),14,16-hexa-ene-2-carboxyl-ate.

The title compound, C(45)H(34)O(4), is the product of a tandem 'pincer' Diels-Alder reaction consisting of two consecutive [4 + 2] cyclo-additions between two 2-benzofuran units and ethyl propiolate. The mol-ecule comprises a fused hexa-cyclic system containing four five-membered rings, which are in the usual envelope conformation, and two six-membered rings. In addition, four phenyl rings are attached to the hexa-cyclic system. The packing is stabilized by C-H⋯π inter-actions.

Related literature

For the tandem ‘pincer’ Diels–Alder reaction, see: Lautens & Fillion (1997 ▶). For related structures, see: Gurbanov et al. (2009 ▶); Toze et al. (2010 ▶).

Experimental

Crystal data

C45H34O4

M = 638.72

Orthorhombic,

a = 17.2498 (4) Å

b = 12.5137 (3) Å

c = 15.4118 (5) Å

V = 3326.77 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.989

19378 measured reflections

5474 independent reflections

4366 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.00

5474 reflections

443 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045873/rk2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045873/rk2244Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C45H34O4	Dx = 1.275 Mg m−3
Mr = 638.72	Melting point = 451–453 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5474 reflections
a = 17.2498 (4) Å	θ = 1.0–26.9°
b = 12.5137 (3) Å	µ = 0.08 mm−1
c = 15.4118 (5) Å	T = 295 K
V = 3326.77 (15) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 1344

Bruker Kappa APEXII CCD diffractometer	5474 independent reflections
Radiation source: fine–focus sealed tube	4366 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 26.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→20
Tmin = 0.962, Tmax = 0.989	k = −15→15
19378 measured reflections	l = −14→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.1034P] where P = (Fo2 + 2Fc2)/3
5474 reflections	(Δ/σ)max < 0.001
443 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.20543 (10)	0.38628 (15)	0.29734 (15)	0.0333 (4)
C2	0.19096 (11)	0.35324 (15)	0.39052 (15)	0.0349 (4)
C3	0.21738 (13)	0.27151 (17)	0.44218 (17)	0.0440 (5)
H3	0.2527	0.2216	0.4211	0.053*
C4	0.18998 (15)	0.2655 (2)	0.52647 (19)	0.0574 (7)
H4	0.2064	0.2100	0.5621	0.069*
C5	0.13896 (15)	0.3400 (2)	0.55862 (19)	0.0571 (6)
H5	0.1212	0.3338	0.6154	0.069*
C6	0.11365 (12)	0.42444 (18)	0.50730 (17)	0.0442 (5)
H6	0.0805	0.4764	0.5293	0.053*
C7	0.13913 (11)	0.42854 (15)	0.42326 (15)	0.0356 (5)
C8	0.12338 (10)	0.50524 (14)	0.34842 (15)	0.0331 (4)
C9	0.04568 (10)	0.55950 (15)	0.34911 (16)	0.0375 (5)
C10	−0.01251 (11)	0.52952 (19)	0.29307 (18)	0.0487 (6)
H10	−0.0041	0.4746	0.2535	0.058*
C11	−0.08388 (13)	0.5812 (2)	0.2956 (2)	0.0619 (7)
H11	−0.1231	0.5603	0.2578	0.074*
C12	−0.09681 (14)	0.6620 (2)	0.3526 (2)	0.0659 (8)
H12	−0.1442	0.6974	0.3530	0.079*
C13	−0.04019 (15)	0.6907 (2)	0.4090 (3)	0.0740 (10)
H13	−0.0491	0.7454	0.4486	0.089*
C14	0.03077 (13)	0.63902 (19)	0.4079 (2)	0.0594 (7)
H14	0.0688	0.6586	0.4476	0.071*
C15	0.22514 (12)	0.30145 (15)	0.23155 (15)	0.0372 (5)
C16	0.29011 (13)	0.23665 (16)	0.24033 (19)	0.0489 (6)
H16	0.3211	0.2423	0.2895	0.059*
C17	0.30888 (15)	0.16377 (18)	0.1762 (2)	0.0585 (7)
H17	0.3528	0.1214	0.1825	0.070*
C18	0.26396 (16)	0.15304 (19)	0.1038 (2)	0.0595 (7)
H18	0.2780	0.1053	0.0603	0.071*
C19	0.19801 (15)	0.21312 (18)	0.09574 (19)	0.0564 (7)
H19	0.1662	0.2044	0.0476	0.068*
C20	0.17865 (14)	0.28670 (16)	0.15910 (17)	0.0456 (5)
H20	0.1337	0.3270	0.1530	0.055*
C21	0.25748 (10)	0.49143 (14)	0.30407 (15)	0.0319 (4)
C22	0.19772 (10)	0.57437 (14)	0.33934 (15)	0.0313 (4)
H22	0.2141	0.6002	0.3965	0.038*
C23	0.20355 (10)	0.66599 (14)	0.27165 (14)	0.0329 (4)
C24	0.28491 (11)	0.54884 (15)	0.21709 (15)	0.0350 (5)
C25	0.32570 (11)	0.48322 (16)	0.36640 (16)	0.0381 (5)
C26	0.44065 (14)	0.3879 (2)	0.4005 (2)	0.0689 (8)
H26A	0.4268	0.3728	0.4602	0.083*
H26B	0.4708	0.4534	0.3992	0.083*
C27	0.48667 (16)	0.2985 (2)	0.3642 (3)	0.0871 (11)
H27A	0.4561	0.2344	0.3648	0.131*
H27B	0.5324	0.2882	0.3986	0.131*
H27C	0.5013	0.3150	0.3056	0.131*
C28	0.21839 (11)	0.55562 (14)	0.15257 (15)	0.0345 (4)
C29	0.20378 (13)	0.51152 (17)	0.07231 (17)	0.0451 (5)
H29	0.2372	0.4611	0.0486	0.054*
C30	0.13833 (16)	0.54386 (19)	0.02773 (18)	0.0552 (6)
H30	0.1285	0.5164	−0.0273	0.066*
C31	0.08712 (14)	0.61661 (19)	0.06384 (19)	0.0543 (7)
H31	0.0430	0.6367	0.0332	0.065*
C32	0.10079 (12)	0.65951 (16)	0.14468 (17)	0.0431 (5)
H32	0.0659	0.7071	0.1697	0.052*
C33	0.16744 (11)	0.63003 (14)	0.18725 (15)	0.0343 (5)
C34	0.36412 (12)	0.52056 (16)	0.18220 (16)	0.0406 (5)
C35	0.37622 (13)	0.42842 (18)	0.13515 (18)	0.0508 (6)
H35	0.3347	0.3831	0.1236	0.061*
C36	0.44885 (15)	0.4026 (2)	0.1051 (2)	0.0671 (8)
H36	0.4563	0.3394	0.0744	0.080*
C37	0.51000 (16)	0.4690 (2)	0.1199 (3)	0.0912 (13)
H37	0.5589	0.4525	0.0983	0.109*
C38	0.49869 (14)	0.5601 (2)	0.1669 (3)	0.0967 (15)
H38	0.5405	0.6051	0.1777	0.116*
C39	0.42635 (13)	0.58658 (18)	0.1986 (2)	0.0661 (9)
H39	0.4196	0.6487	0.2308	0.079*
C40	0.18919 (10)	0.78078 (15)	0.29744 (16)	0.0359 (5)
C41	0.17398 (14)	0.81397 (17)	0.38066 (18)	0.0511 (6)
H41	0.1721	0.7642	0.4254	0.061*
C42	0.16133 (16)	0.92160 (19)	0.3985 (2)	0.0619 (7)
H42	0.1492	0.9428	0.4547	0.074*
C43	0.16647 (15)	0.99565 (18)	0.3347 (2)	0.0625 (8)
H43	0.1578	1.0674	0.3469	0.075*
C44	0.18442 (15)	0.96424 (18)	0.2525 (2)	0.0646 (8)
H44	0.1895	1.0151	0.2089	0.078*
C45	0.19522 (13)	0.85747 (16)	0.23348 (19)	0.0513 (6)
H45	0.2067	0.8370	0.1769	0.062*
O1	0.13122 (7)	0.43327 (10)	0.27592 (10)	0.0339 (3)
O2	0.28543 (7)	0.65724 (9)	0.24881 (10)	0.0350 (3)
O3	0.33920 (10)	0.54448 (14)	0.42352 (14)	0.0626 (5)
O4	0.37114 (8)	0.40007 (11)	0.34821 (12)	0.0474 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0294 (10)	0.0329 (9)	0.0376 (12)	−0.0013 (7)	−0.0052 (9)	0.0027 (9)
C2	0.0337 (10)	0.0327 (9)	0.0381 (12)	−0.0041 (8)	−0.0040 (9)	0.0019 (9)
C3	0.0464 (12)	0.0394 (11)	0.0460 (15)	0.0039 (9)	−0.0069 (11)	0.0074 (11)
C4	0.0713 (17)	0.0524 (13)	0.0486 (16)	0.0041 (12)	−0.0116 (14)	0.0182 (13)
C5	0.0709 (16)	0.0634 (15)	0.0371 (14)	−0.0021 (13)	0.0034 (12)	0.0091 (13)
C6	0.0453 (13)	0.0455 (12)	0.0418 (14)	−0.0011 (9)	0.0029 (10)	0.0020 (11)
C7	0.0307 (10)	0.0356 (10)	0.0405 (13)	−0.0029 (8)	−0.0040 (9)	0.0040 (10)
C8	0.0299 (9)	0.0324 (9)	0.0371 (12)	−0.0023 (7)	−0.0034 (9)	0.0002 (10)
C9	0.0303 (9)	0.0372 (9)	0.0450 (13)	−0.0005 (7)	0.0022 (10)	0.0097 (10)
C10	0.0358 (12)	0.0577 (13)	0.0527 (16)	−0.0003 (9)	−0.0044 (11)	0.0093 (12)
C11	0.0353 (12)	0.0826 (18)	0.068 (2)	0.0032 (11)	−0.0080 (12)	0.0181 (17)
C12	0.0339 (13)	0.0700 (16)	0.094 (2)	0.0146 (11)	0.0082 (15)	0.0281 (18)
C13	0.0465 (15)	0.0631 (15)	0.112 (3)	0.0139 (11)	0.0137 (16)	−0.0142 (18)
C14	0.0324 (12)	0.0625 (14)	0.083 (2)	0.0039 (10)	−0.0013 (12)	−0.0182 (15)
C15	0.0400 (11)	0.0315 (9)	0.0400 (13)	−0.0053 (8)	0.0004 (9)	0.0015 (9)
C16	0.0499 (12)	0.0406 (11)	0.0561 (16)	0.0033 (9)	−0.0044 (12)	−0.0026 (12)
C17	0.0645 (16)	0.0429 (12)	0.068 (2)	0.0084 (11)	0.0081 (14)	−0.0046 (13)
C18	0.0860 (19)	0.0405 (12)	0.0519 (17)	0.0016 (12)	0.0135 (15)	−0.0092 (12)
C19	0.0799 (18)	0.0442 (12)	0.0452 (16)	−0.0080 (12)	−0.0051 (13)	−0.0051 (12)
C20	0.0567 (14)	0.0352 (10)	0.0447 (14)	−0.0033 (9)	−0.0053 (11)	−0.0012 (11)
C21	0.0290 (10)	0.0312 (9)	0.0355 (12)	0.0008 (7)	−0.0040 (8)	−0.0013 (9)
C22	0.0300 (9)	0.0306 (9)	0.0334 (11)	−0.0006 (7)	−0.0035 (9)	0.0004 (9)
C23	0.0238 (9)	0.0336 (9)	0.0411 (12)	0.0001 (7)	−0.0011 (8)	0.0036 (9)
C24	0.0316 (10)	0.0328 (9)	0.0405 (13)	−0.0010 (7)	0.0000 (9)	0.0017 (9)
C25	0.0314 (10)	0.0399 (10)	0.0431 (14)	0.0018 (8)	−0.0049 (9)	−0.0003 (10)
C26	0.0469 (14)	0.0709 (16)	0.089 (2)	0.0162 (12)	−0.0281 (15)	−0.0003 (17)
C27	0.0543 (16)	0.0868 (19)	0.120 (3)	0.0309 (14)	−0.0158 (18)	0.004 (2)
C28	0.0354 (10)	0.0343 (9)	0.0339 (12)	−0.0073 (8)	0.0003 (9)	0.0066 (10)
C29	0.0539 (14)	0.0430 (11)	0.0385 (13)	−0.0052 (9)	−0.0007 (11)	0.0014 (11)
C30	0.0707 (17)	0.0522 (13)	0.0427 (15)	−0.0120 (12)	−0.0160 (13)	0.0031 (12)
C31	0.0523 (14)	0.0559 (14)	0.0548 (17)	−0.0090 (11)	−0.0204 (12)	0.0107 (13)
C32	0.0385 (11)	0.0414 (10)	0.0496 (15)	−0.0031 (9)	−0.0088 (11)	0.0099 (11)
C33	0.0321 (10)	0.0317 (9)	0.0390 (12)	−0.0050 (7)	−0.0013 (9)	0.0088 (9)
C34	0.0346 (11)	0.0398 (10)	0.0475 (14)	0.0021 (8)	0.0060 (10)	0.0099 (11)
C35	0.0484 (13)	0.0518 (13)	0.0520 (17)	0.0032 (10)	0.0081 (11)	−0.0020 (12)
C36	0.0620 (17)	0.0616 (15)	0.078 (2)	0.0172 (13)	0.0226 (15)	0.0008 (15)
C37	0.0488 (16)	0.0731 (19)	0.152 (4)	0.0151 (14)	0.041 (2)	0.015 (2)
C38	0.0384 (14)	0.0567 (16)	0.195 (5)	−0.0017 (11)	0.027 (2)	0.005 (2)
C39	0.0354 (12)	0.0439 (12)	0.119 (3)	−0.0022 (10)	0.0095 (14)	−0.0018 (15)
C40	0.0273 (9)	0.0345 (9)	0.0459 (14)	−0.0023 (7)	−0.0055 (9)	0.0026 (10)
C41	0.0608 (15)	0.0427 (12)	0.0500 (16)	0.0003 (10)	−0.0029 (12)	−0.0011 (12)
C42	0.0714 (17)	0.0532 (14)	0.0612 (19)	0.0038 (12)	−0.0058 (14)	−0.0173 (14)
C43	0.0637 (15)	0.0354 (12)	0.088 (2)	0.0008 (10)	−0.0147 (16)	−0.0093 (15)
C44	0.0728 (18)	0.0367 (12)	0.084 (2)	−0.0056 (11)	−0.0084 (17)	0.0140 (15)
C45	0.0575 (14)	0.0410 (11)	0.0555 (16)	−0.0058 (9)	0.0024 (12)	0.0048 (12)
O1	0.0302 (7)	0.0346 (7)	0.0368 (9)	−0.0016 (5)	−0.0061 (6)	0.0017 (6)
O2	0.0280 (6)	0.0325 (6)	0.0445 (9)	−0.0022 (5)	−0.0013 (6)	−0.0001 (7)
O3	0.0529 (10)	0.0678 (10)	0.0670 (13)	0.0154 (8)	−0.0274 (9)	−0.0264 (10)
O4	0.0386 (8)	0.0463 (7)	0.0574 (11)	0.0109 (6)	−0.0137 (8)	−0.0016 (8)

C1—O1	1.447 (2)	C23—C40	1.511 (3)
C1—C15	1.507 (3)	C23—C33	1.511 (3)
C1—C2	1.515 (3)	C24—O2	1.442 (2)
C1—C21	1.596 (2)	C24—C34	1.510 (3)
C2—C3	1.374 (3)	C24—C28	1.521 (3)
C2—C7	1.394 (3)	C25—O3	1.190 (3)
C3—C4	1.385 (4)	C25—O4	1.333 (2)
C3—H3	0.9300	C26—O4	1.453 (3)
C4—C5	1.374 (4)	C26—C27	1.482 (4)
C4—H4	0.9300	C26—H26A	0.9700
C5—C6	1.391 (3)	C26—H26B	0.9700
C5—H5	0.9300	C27—H27A	0.9600
C6—C7	1.369 (3)	C27—H27B	0.9600
C6—H6	0.9300	C27—H27C	0.9600
C7—C8	1.525 (3)	C28—C29	1.378 (3)
C8—O1	1.441 (3)	C28—C33	1.387 (3)
C8—C9	1.503 (3)	C29—C30	1.382 (3)
C8—C22	1.553 (2)	C29—H29	0.9300
C9—C14	1.370 (3)	C30—C31	1.385 (4)
C9—C10	1.376 (3)	C30—H30	0.9300
C10—C11	1.391 (3)	C31—C32	1.377 (4)
C10—H10	0.9300	C31—H31	0.9300
C11—C12	1.357 (4)	C32—C33	1.374 (3)
C11—H11	0.9300	C32—H32	0.9300
C12—C13	1.356 (5)	C34—C39	1.378 (3)
C12—H12	0.9300	C34—C35	1.378 (3)
C13—C14	1.384 (3)	C35—C36	1.374 (3)
C13—H13	0.9300	C35—H35	0.9300
C14—H14	0.9300	C36—C37	1.362 (4)
C15—C20	1.387 (3)	C36—H36	0.9300
C15—C16	1.390 (3)	C37—C38	1.363 (5)
C16—C17	1.383 (4)	C37—H37	0.9300
C16—H16	0.9300	C38—C39	1.381 (4)
C17—C18	1.365 (4)	C38—H38	0.9300
C17—H17	0.9300	C39—H39	0.9300
C18—C19	1.369 (4)	C40—C41	1.373 (3)
C18—H18	0.9300	C40—C45	1.380 (3)
C19—C20	1.383 (4)	C41—C42	1.392 (3)
C19—H19	0.9300	C41—H41	0.9300
C20—H20	0.9300	C42—C43	1.354 (4)
C21—C25	1.523 (3)	C42—H42	0.9300
C21—C22	1.561 (3)	C43—C44	1.361 (4)
C21—C24	1.593 (3)	C43—H43	0.9300
C22—C23	1.553 (3)	C44—C45	1.381 (3)
C22—H22	0.9800	C44—H44	0.9300
C23—O2	1.460 (2)	C45—H45	0.9300
O1—C1—C15	109.42 (16)	O2—C23—C22	99.75 (13)
O1—C1—C2	100.46 (15)	C40—C23—C22	120.96 (18)
C15—C1—C2	118.86 (16)	C33—C23—C22	109.37 (14)
O1—C1—C21	100.22 (13)	O2—C24—C34	109.60 (15)
C15—C1—C21	119.83 (17)	O2—C24—C28	100.02 (14)
C2—C1—C21	104.83 (17)	C34—C24—C28	117.57 (19)
C3—C2—C7	120.4 (2)	O2—C24—C21	98.09 (15)
C3—C2—C1	134.3 (2)	C34—C24—C21	117.56 (16)
C7—C2—C1	105.33 (17)	C28—C24—C21	110.57 (15)
C2—C3—C4	118.1 (2)	O3—C25—O4	122.92 (19)
C2—C3—H3	121.0	O3—C25—C21	125.05 (18)
C4—C3—H3	121.0	O4—C25—C21	112.00 (18)
C5—C4—C3	121.4 (2)	O4—C26—C27	108.2 (3)
C5—C4—H4	119.3	O4—C26—H26A	110.1
C3—C4—H4	119.3	C27—C26—H26A	110.1
C4—C5—C6	120.8 (3)	O4—C26—H26B	110.1
C4—C5—H5	119.6	C27—C26—H26B	110.1
C6—C5—H5	119.6	H26A—C26—H26B	108.4
C7—C6—C5	117.8 (2)	C26—C27—H27A	109.5
C7—C6—H6	121.1	C26—C27—H27B	109.5
C5—C6—H6	121.1	H27A—C27—H27B	109.5
C6—C7—C2	121.56 (19)	C26—C27—H27C	109.5
C6—C7—C8	133.01 (19)	H27A—C27—H27C	109.5
C2—C7—C8	105.43 (19)	H27B—C27—H27C	109.5
O1—C8—C9	111.80 (17)	C29—C28—C33	119.9 (2)
O1—C8—C7	100.16 (13)	C29—C28—C24	134.64 (19)
C9—C8—C7	115.98 (18)	C33—C28—C24	105.28 (18)
O1—C8—C22	101.58 (16)	C28—C29—C30	118.6 (2)
C9—C8—C22	119.04 (14)	C28—C29—H29	120.7
C7—C8—C22	105.76 (16)	C30—C29—H29	120.7
C14—C9—C10	118.42 (19)	C29—C30—C31	120.9 (2)
C14—C9—C8	120.0 (2)	C29—C30—H30	119.5
C10—C9—C8	121.5 (2)	C31—C30—H30	119.5
C9—C10—C11	120.1 (3)	C32—C31—C30	120.7 (2)
C9—C10—H10	120.0	C32—C31—H31	119.6
C11—C10—H10	120.0	C30—C31—H31	119.6
C12—C11—C10	120.6 (3)	C33—C32—C31	118.1 (2)
C12—C11—H11	119.7	C33—C32—H32	121.0
C10—C11—H11	119.7	C31—C32—H32	121.0
C13—C12—C11	119.6 (2)	C32—C33—C28	121.8 (2)
C13—C12—H12	120.2	C32—C33—C23	132.54 (19)
C11—C12—H12	120.2	C28—C33—C23	105.68 (16)
C12—C13—C14	120.4 (3)	C39—C34—C35	118.7 (2)
C12—C13—H13	119.8	C39—C34—C24	119.9 (2)
C14—C13—H13	119.8	C35—C34—C24	121.36 (19)
C9—C14—C13	120.9 (3)	C36—C35—C34	120.8 (2)
C9—C14—H14	119.6	C36—C35—H35	119.6
C13—C14—H14	119.6	C34—C35—H35	119.6
C20—C15—C16	117.8 (2)	C37—C36—C35	120.4 (3)
C20—C15—C1	120.32 (19)	C37—C36—H36	119.8
C16—C15—C1	121.8 (2)	C35—C36—H36	119.8
C17—C16—C15	120.3 (2)	C36—C37—C38	119.2 (2)
C17—C16—H16	119.9	C36—C37—H37	120.4
C15—C16—H16	119.9	C38—C37—H37	120.4
C18—C17—C16	121.1 (2)	C37—C38—C39	121.2 (3)
C18—C17—H17	119.5	C37—C38—H38	119.4
C16—C17—H17	119.5	C39—C38—H38	119.4
C17—C18—C19	119.5 (2)	C34—C39—C38	119.7 (3)
C17—C18—H18	120.3	C34—C39—H39	120.2
C19—C18—H18	120.3	C38—C39—H39	120.2
C18—C19—C20	120.1 (2)	C41—C40—C45	118.1 (2)
C18—C19—H19	119.9	C41—C40—C23	124.4 (2)
C20—C19—H19	119.9	C45—C40—C23	117.5 (2)
C19—C20—C15	121.2 (2)	C40—C41—C42	120.4 (2)
C19—C20—H20	119.4	C40—C41—H41	119.8
C15—C20—H20	119.4	C42—C41—H41	119.8
C25—C21—C22	109.61 (17)	C43—C42—C41	120.6 (3)
C25—C21—C24	109.38 (15)	C43—C42—H42	119.7
C22—C21—C24	100.92 (14)	C41—C42—H42	119.7
C25—C21—C1	114.84 (16)	C42—C43—C44	119.5 (2)
C22—C21—C1	101.49 (14)	C42—C43—H43	120.2
C24—C21—C1	118.96 (17)	C44—C43—H43	120.2
C8—C22—C23	121.68 (16)	C43—C44—C45	120.5 (3)
C8—C22—C21	101.91 (14)	C43—C44—H44	119.7
C23—C22—C21	102.37 (16)	C45—C44—H44	119.7
C8—C22—H22	110.0	C40—C45—C44	120.7 (3)
C23—C22—H22	110.0	C40—C45—H45	119.6
C21—C22—H22	110.0	C44—C45—H45	119.6
O2—C23—C40	107.06 (14)	C8—O1—C1	99.21 (14)
O2—C23—C33	99.73 (16)	C24—O2—C23	98.41 (13)
C40—C23—C33	116.23 (16)	C25—O4—C26	116.77 (19)
O1—C1—C2—C3	148.7 (2)	C1—C21—C24—O2	147.77 (15)
C15—C1—C2—C3	29.5 (3)	C25—C21—C24—C34	39.6 (2)
C21—C1—C2—C3	−107.7 (2)	C22—C21—C24—C34	155.13 (17)
O1—C1—C2—C7	−31.59 (18)	C1—C21—C24—C34	−95.1 (2)
C15—C1—C2—C7	−150.79 (17)	C25—C21—C24—C28	178.55 (16)
C21—C1—C2—C7	72.03 (17)	C22—C21—C24—C28	−65.97 (18)
C7—C2—C3—C4	1.1 (3)	C1—C21—C24—C28	43.8 (2)
C1—C2—C3—C4	−179.2 (2)	C22—C21—C25—O3	−13.6 (3)
C2—C3—C4—C5	−1.2 (4)	C24—C21—C25—O3	96.2 (3)
C3—C4—C5—C6	−0.5 (4)	C1—C21—C25—O3	−127.1 (2)
C4—C5—C6—C7	2.2 (4)	C22—C21—C25—O4	168.36 (16)
C5—C6—C7—C2	−2.3 (3)	C24—C21—C25—O4	−81.9 (2)
C5—C6—C7—C8	178.6 (2)	C1—C21—C25—O4	54.9 (2)
C3—C2—C7—C6	0.7 (3)	O2—C24—C28—C29	143.1 (2)
C1—C2—C7—C6	−179.10 (18)	C34—C24—C28—C29	24.6 (3)
C3—C2—C7—C8	179.99 (18)	C21—C24—C28—C29	−114.3 (3)
C1—C2—C7—C8	0.20 (19)	O2—C24—C28—C33	−32.20 (18)
C6—C7—C8—O1	−149.5 (2)	C34—C24—C28—C33	−150.66 (17)
C2—C7—C8—O1	31.36 (17)	C21—C24—C28—C33	70.45 (18)
C6—C7—C8—C9	−29.0 (3)	C33—C28—C29—C30	0.6 (3)
C2—C7—C8—C9	151.83 (17)	C24—C28—C29—C30	−174.1 (2)
C6—C7—C8—C22	105.3 (3)	C28—C29—C30—C31	−1.9 (3)
C2—C7—C8—C22	−73.85 (19)	C29—C30—C31—C32	0.9 (4)
O1—C8—C9—C14	−173.1 (2)	C30—C31—C32—C33	1.5 (3)
C7—C8—C9—C14	72.9 (3)	C31—C32—C33—C28	−2.9 (3)
C22—C8—C9—C14	−55.1 (3)	C31—C32—C33—C23	174.9 (2)
O1—C8—C9—C10	8.5 (3)	C29—C28—C33—C32	1.8 (3)
C7—C8—C9—C10	−105.4 (2)	C24—C28—C33—C32	177.97 (18)
C22—C8—C9—C10	126.5 (2)	C29—C28—C33—C23	−176.49 (18)
C14—C9—C10—C11	1.4 (4)	C24—C28—C33—C23	−0.36 (19)
C8—C9—C10—C11	179.8 (2)	O2—C23—C33—C32	−145.7 (2)
C9—C10—C11—C12	0.4 (4)	C40—C23—C33—C32	−31.1 (3)
C10—C11—C12—C13	−1.6 (4)	C22—C23—C33—C32	110.2 (2)
C11—C12—C13—C14	0.8 (5)	O2—C23—C33—C28	32.33 (17)
C10—C9—C14—C13	−2.2 (4)	C40—C23—C33—C28	146.94 (16)
C8—C9—C14—C13	179.4 (2)	C22—C23—C33—C28	−71.69 (18)
C12—C13—C14—C9	1.2 (5)	O2—C24—C34—C39	12.0 (3)
O1—C1—C15—C20	6.4 (3)	C28—C24—C34—C39	125.2 (2)
C2—C1—C15—C20	120.9 (2)	C21—C24—C34—C39	−98.7 (3)
C21—C1—C15—C20	−108.4 (2)	O2—C24—C34—C35	−169.2 (2)
O1—C1—C15—C16	−174.34 (18)	C28—C24—C34—C35	−55.9 (3)
C2—C1—C15—C16	−59.9 (3)	C21—C24—C34—C35	80.1 (3)
C21—C1—C15—C16	70.9 (3)	C39—C34—C35—C36	0.0 (4)
C20—C15—C16—C17	3.0 (3)	C24—C34—C35—C36	−178.8 (2)
C1—C15—C16—C17	−176.3 (2)	C34—C35—C36—C37	−1.3 (5)
C15—C16—C17—C18	−0.7 (4)	C35—C36—C37—C38	1.6 (6)
C16—C17—C18—C19	−2.0 (4)	C36—C37—C38—C39	−0.8 (6)
C17—C18—C19—C20	2.2 (4)	C35—C34—C39—C38	0.8 (4)
C18—C19—C20—C15	0.1 (4)	C24—C34—C39—C38	179.7 (3)
C16—C15—C20—C19	−2.7 (3)	C37—C38—C39—C34	−0.5 (6)
C1—C15—C20—C19	176.6 (2)	O2—C23—C40—C41	−109.8 (2)
O1—C1—C21—C25	150.94 (17)	C33—C23—C40—C41	139.8 (2)
C15—C1—C21—C25	−89.5 (2)	C22—C23—C40—C41	3.2 (3)
C2—C1—C21—C25	47.1 (2)	O2—C23—C40—C45	67.2 (2)
O1—C1—C21—C22	32.8 (2)	C33—C23—C40—C45	−43.2 (2)
C15—C1—C21—C22	152.33 (18)	C22—C23—C40—C45	−179.77 (17)
C2—C1—C21—C22	−71.00 (18)	C45—C40—C41—C42	3.1 (3)
O1—C1—C21—C24	−76.68 (19)	C23—C40—C41—C42	−179.9 (2)
C15—C1—C21—C24	42.9 (2)	C40—C41—C42—C43	−2.3 (4)
C2—C1—C21—C24	179.53 (15)	C41—C42—C43—C44	−0.2 (4)
O1—C8—C22—C23	78.17 (19)	C42—C43—C44—C45	1.8 (4)
C9—C8—C22—C23	−45.0 (3)	C41—C40—C45—C44	−1.5 (3)
C7—C8—C22—C23	−177.65 (17)	C23—C40—C45—C44	−178.7 (2)
O1—C8—C22—C21	−34.62 (19)	C43—C44—C45—C40	−1.0 (4)
C9—C8—C22—C21	−157.8 (2)	C9—C8—O1—C1	−174.22 (15)
C7—C8—C22—C21	69.6 (2)	C7—C8—O1—C1	−50.79 (15)
C25—C21—C22—C8	−120.98 (18)	C22—C8—O1—C1	57.78 (16)
C24—C21—C22—C8	123.71 (16)	C15—C1—O1—C8	177.00 (15)
C1—C21—C22—C8	0.9 (2)	C2—C1—O1—C8	51.16 (15)
C25—C21—C22—C23	112.46 (18)	C21—C1—O1—C8	−56.16 (17)
C24—C21—C22—C23	−2.85 (17)	C34—C24—O2—C23	176.01 (18)
C1—C21—C22—C23	−125.70 (16)	C28—C24—O2—C23	51.83 (17)
C8—C22—C23—O2	−145.34 (18)	C21—C24—O2—C23	−60.84 (15)
C21—C22—C23—O2	−32.79 (17)	C40—C23—O2—C24	−173.51 (17)
C8—C22—C23—C40	97.9 (2)	C33—C23—O2—C24	−52.06 (16)
C21—C22—C23—C40	−149.55 (16)	C22—C23—O2—C24	59.70 (17)
C8—C22—C23—C33	−41.3 (2)	O3—C25—O4—C26	−1.5 (3)
C21—C22—C23—C33	71.22 (17)	C21—C25—O4—C26	176.5 (2)
C25—C21—C24—O2	−77.51 (17)	C27—C26—O4—C25	−174.2 (2)
C22—C21—C24—O2	37.98 (16)

Cg8 and Cg10 are the centroids of the C15–C20 and C28–C33 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg10i	0.93	2.97	3.740 (3)	141
C35—H35···Cg8	0.93	2.60	3.446 (2)	151
C44—H44···Cg8ii	0.93	2.87	3.671 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg8 and Cg10 are the centroids of the C15–C20 and C28–C33 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg10i	0.93	2.97	3.740 (3)	141
C35—H35⋯Cg8	0.93	2.60	3.446 (2)	151
C44—H44⋯Cg8ii	0.93	2.87	3.671 (3)	145

Symmetry codes: (i) ; (ii) .