(2E,25E)-11,14,17,33,36,39,42-Hepta-oxa-penta-cyclo-[41.4.0.0.0.0]hepta-tetra-conta-1(43),2,5(10),6,8,18,20,22,25,27,29,31,44,46-tetra-decaene-4,24-dione.

The title compound, C(40)H(40)O(9), is a product of the double crotonic condensation of bis-(2-acetyl-phen-oxy)-3-oxapentane with bis-(2-formyl-phen-oxy)-3,6-dioxaoctane. The title macromolecule includes the 31-crown-7-ether skeletal unit and adopts a saddle-like conformation. The two ethyl-ene fragments have E configurations. The volume of the inter-nal cavity of the macrocycle is approximately 125 Å(3). In the crystal, the mol-ecules are arranged at van der Waals distances.

Related literature

For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supra­molecular chemistry, see: Hiraoka (1978 ▶); Pedersen (1988 ▶); Bradshaw & Izatt (1997) ▶; Gokel & Murillo (1996 ▶). For related compounds, see: Levov et al. (2006 ▶, 2008 ▶); Anh et al. (2008 ▶)

Experimental

Crystal data

C40H40O9

M = 664.72

Monoclinic,

a = 12.3268 (6) Å

b = 11.0271 (6) Å

c = 13.1142 (7) Å

β = 106.933 (1)°

V = 1705.32 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.973, T max = 0.982

19455 measured reflections

5222 independent reflections

4511 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.128

S = 1.01

5222 reflections

442 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013201/rk2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013201/rk2273Isup2.hkl

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

C40H40O9	F(000) = 704
Mr = 664.72	Dx = 1.294 Mg m−3
Monoclinic, P21	Melting point = 400–402 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 12.3268 (6) Å	Cell parameters from 7007 reflections
b = 11.0271 (6) Å	θ = 2.5–29.6°
c = 13.1142 (7) Å	µ = 0.09 mm−1
β = 106.933 (1)°	T = 120 K
V = 1705.32 (15) Å3	Prism, light–yellow
Z = 2	0.30 × 0.30 × 0.20 mm

Bruker SMART 1K CCD diffractometer	5222 independent reflections
Radiation source: fine-focus sealed tube	4511 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −16→17
Tmin = 0.973, Tmax = 0.982	k = −15→15
19455 measured reflections	l = −18→18

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.06P)2 + 0.86P] where P = (Fo2 + 2Fc2)/3
5222 reflections	(Δ/σ)max < 0.001
442 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.20 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 > 2σ(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	0.4588 (2)	0.6322 (2)	0.41234 (19)	0.0280 (5)
C2	0.3718 (2)	0.6146 (3)	0.46784 (18)	0.0280 (5)
H2	0.3347	0.5381	0.4603	0.034*
C3	0.3411 (2)	0.6979 (3)	0.5280 (2)	0.0330 (5)
H3	0.3786	0.7742	0.5375	0.040*
C4	0.2520 (2)	0.6771 (3)	0.5802 (2)	0.0325 (5)
O4	0.2392 (2)	0.7497 (3)	0.64613 (19)	0.0559 (7)
C5	0.1818 (2)	0.5638 (3)	0.55711 (19)	0.0290 (5)
C6	0.1917 (2)	0.4805 (3)	0.6388 (2)	0.0359 (6)
H6	0.2416	0.4975	0.7075	0.043*
C7	0.1304 (3)	0.3732 (3)	0.6222 (3)	0.0422 (7)
H7	0.1392	0.3165	0.6786	0.051*
C8	0.0566 (3)	0.3495 (3)	0.5232 (3)	0.0438 (7)
H8	0.0149	0.2759	0.5112	0.053*
C9	0.0426 (3)	0.4326 (3)	0.4402 (2)	0.0371 (6)
H9	−0.0099	0.4163	0.3726	0.044*
C10	0.1056 (2)	0.5392 (2)	0.4565 (2)	0.0295 (5)
O11	0.09816 (16)	0.62631 (18)	0.38125 (13)	0.0306 (4)
C12	0.0157 (2)	0.6097 (3)	0.2789 (2)	0.0321 (5)
H12A	−0.0607	0.5992	0.2879	0.039*
H12B	0.0342	0.5363	0.2438	0.039*
C13	0.0177 (2)	0.7199 (3)	0.2117 (2)	0.0309 (5)
H13A	−0.0582	0.7298	0.1598	0.037*
H13B	0.0322	0.7923	0.2585	0.037*
O14	0.10022 (15)	0.71629 (19)	0.15489 (13)	0.0313 (4)
C15	0.2133 (2)	0.7259 (3)	0.22173 (19)	0.0305 (5)
H15A	0.2341	0.6520	0.2660	0.037*
H15B	0.2204	0.7965	0.2698	0.037*
C16	0.2910 (2)	0.7410 (2)	0.15298 (19)	0.0294 (5)
H16A	0.2647	0.8082	0.1016	0.035*
H16B	0.3692	0.7589	0.1974	0.035*
O17	0.28744 (16)	0.62817 (17)	0.09792 (14)	0.0308 (4)
C18	0.34907 (19)	0.6155 (2)	0.02800 (18)	0.0257 (4)
C19	0.4309 (2)	0.6979 (3)	0.0181 (2)	0.0314 (5)
H19	0.4429	0.7709	0.0583	0.038*
C20	0.4949 (2)	0.6732 (3)	−0.0504 (2)	0.0369 (6)
H20	0.5507	0.7298	−0.0567	0.044*
C21	0.4791 (2)	0.5674 (3)	−0.1099 (2)	0.0368 (6)
H21	0.5234	0.5515	−0.1568	0.044*
C22	0.3976 (2)	0.4848 (3)	−0.1002 (2)	0.0305 (5)
H22	0.3881	0.4110	−0.1392	0.037*
C23	0.32910 (19)	0.5088 (2)	−0.03355 (18)	0.0248 (4)
C24	0.2399 (2)	0.4172 (2)	−0.03145 (19)	0.0266 (5)
O24	0.25237 (16)	0.31193 (18)	−0.05580 (17)	0.0365 (4)
C25	0.1368 (2)	0.4551 (2)	−0.00417 (19)	0.0258 (4)
H25	0.1164	0.5384	−0.0079	0.031*
C26	0.07174 (19)	0.3731 (2)	0.02578 (18)	0.0246 (4)
H26	0.0963	0.2910	0.0314	0.030*
C27	−0.03407 (19)	0.4002 (2)	0.05046 (18)	0.0238 (4)
C28	−0.0994 (2)	0.5025 (2)	0.0089 (2)	0.0275 (5)
H28	−0.0736	0.5571	−0.0351	0.033*
C29	−0.2012 (2)	0.5259 (2)	0.0307 (2)	0.0310 (5)
H29	−0.2447	0.5955	0.0016	0.037*
C30	−0.2387 (2)	0.4466 (3)	0.0954 (2)	0.0328 (5)
H30	−0.3085	0.4620	0.1100	0.039*
C31	−0.1751 (2)	0.3444 (3)	0.13935 (19)	0.0298 (5)
H31	−0.2012	0.2909	0.1839	0.036*
C32	−0.0731 (2)	0.3219 (2)	0.11732 (18)	0.0263 (5)
O33	−0.00317 (15)	0.22654 (18)	0.15923 (14)	0.0312 (4)
C34	−0.0337 (2)	0.1520 (2)	0.2361 (2)	0.0304 (5)
H34A	−0.1030	0.1049	0.2013	0.036*
H34B	−0.0489	0.2031	0.2925	0.036*
C35	0.0637 (2)	0.0675 (3)	0.2836 (2)	0.0346 (5)
H35A	0.0397	0.0026	0.3246	0.042*
H35B	0.0897	0.0294	0.2265	0.042*
O36	0.15233 (17)	0.1363 (2)	0.35162 (16)	0.0397 (5)
C37	0.2517 (2)	0.0645 (3)	0.3974 (2)	0.0430 (7)
H37A	0.2280	−0.0189	0.4091	0.052*
H37B	0.2929	0.0987	0.4679	0.052*
C38	0.3315 (3)	0.0587 (3)	0.3289 (3)	0.0433 (7)
H38A	0.3875	−0.0066	0.3561	0.052*
H38B	0.2873	0.0370	0.2552	0.052*
O39	0.39042 (17)	0.1687 (2)	0.32615 (17)	0.0398 (5)
C40	0.3283 (2)	0.2565 (3)	0.2534 (2)	0.0355 (6)
H40A	0.2639	0.2867	0.2770	0.043*
H40B	0.2978	0.2202	0.1817	0.043*
C41	0.4075 (2)	0.3590 (3)	0.2498 (2)	0.0335 (5)
H41A	0.4825	0.3265	0.2503	0.040*
H41B	0.3769	0.4066	0.1836	0.040*
O42	0.41902 (17)	0.43507 (18)	0.34075 (15)	0.0338 (4)
C43	0.4779 (2)	0.5409 (2)	0.3452 (2)	0.0291 (5)
C44	0.5554 (2)	0.5598 (3)	0.2867 (2)	0.0375 (6)
H44	0.5687	0.4978	0.2416	0.045*
C45	0.6126 (2)	0.6697 (3)	0.2950 (2)	0.0399 (6)
H45	0.6640	0.6831	0.2544	0.048*
C46	0.5952 (2)	0.7595 (3)	0.3620 (2)	0.0402 (6)
H46	0.6354	0.8340	0.3681	0.048*
C47	0.5192 (2)	0.7412 (3)	0.4201 (2)	0.0339 (5)
H47	0.5077	0.8035	0.4659	0.041*

	U11	U22	U33	U12	U13	U23
C1	0.0239 (10)	0.0335 (13)	0.0271 (10)	−0.0007 (10)	0.0083 (8)	0.0022 (10)
C2	0.0250 (10)	0.0333 (12)	0.0254 (10)	−0.0011 (9)	0.0068 (8)	0.0013 (10)
C3	0.0306 (12)	0.0400 (15)	0.0298 (11)	−0.0059 (11)	0.0110 (9)	−0.0065 (11)
C4	0.0299 (11)	0.0424 (15)	0.0266 (11)	−0.0012 (11)	0.0106 (9)	−0.0046 (11)
O4	0.0670 (15)	0.0603 (16)	0.0529 (13)	−0.0158 (13)	0.0372 (12)	−0.0260 (12)
C5	0.0264 (10)	0.0362 (13)	0.0286 (11)	0.0054 (10)	0.0148 (9)	−0.0008 (10)
C6	0.0312 (12)	0.0477 (16)	0.0329 (12)	0.0137 (12)	0.0156 (10)	0.0084 (12)
C7	0.0428 (15)	0.0457 (17)	0.0458 (16)	0.0144 (13)	0.0252 (13)	0.0179 (13)
C8	0.0499 (17)	0.0360 (15)	0.0527 (17)	−0.0003 (13)	0.0264 (14)	0.0066 (13)
C9	0.0418 (14)	0.0332 (14)	0.0385 (14)	−0.0047 (12)	0.0154 (11)	−0.0005 (11)
C10	0.0324 (11)	0.0319 (12)	0.0275 (11)	0.0007 (10)	0.0137 (9)	0.0015 (10)
O11	0.0372 (9)	0.0307 (9)	0.0228 (7)	−0.0078 (8)	0.0071 (7)	−0.0014 (7)
C12	0.0358 (12)	0.0325 (13)	0.0257 (11)	−0.0056 (10)	0.0051 (9)	−0.0024 (10)
C13	0.0315 (12)	0.0341 (13)	0.0291 (11)	0.0037 (10)	0.0118 (9)	0.0036 (10)
O14	0.0298 (8)	0.0393 (10)	0.0261 (8)	0.0015 (8)	0.0101 (6)	0.0012 (8)
C15	0.0306 (12)	0.0336 (12)	0.0275 (11)	−0.0016 (10)	0.0087 (9)	−0.0029 (10)
C16	0.0322 (12)	0.0271 (12)	0.0291 (11)	−0.0037 (10)	0.0095 (9)	−0.0045 (9)
O17	0.0362 (9)	0.0279 (9)	0.0334 (9)	−0.0060 (8)	0.0184 (7)	−0.0049 (7)
C18	0.0238 (10)	0.0283 (11)	0.0254 (10)	−0.0002 (9)	0.0076 (8)	0.0027 (9)
C19	0.0294 (11)	0.0316 (13)	0.0334 (12)	−0.0070 (10)	0.0096 (9)	0.0020 (10)
C20	0.0267 (11)	0.0442 (15)	0.0403 (13)	−0.0087 (11)	0.0108 (10)	0.0056 (12)
C21	0.0284 (12)	0.0488 (17)	0.0373 (13)	−0.0010 (12)	0.0158 (10)	0.0035 (13)
C22	0.0254 (11)	0.0375 (13)	0.0301 (11)	0.0028 (10)	0.0103 (9)	0.0036 (10)
C23	0.0205 (9)	0.0283 (11)	0.0260 (10)	0.0010 (9)	0.0076 (8)	0.0027 (9)
C24	0.0239 (10)	0.0280 (11)	0.0286 (11)	−0.0001 (9)	0.0087 (8)	0.0029 (9)
O24	0.0329 (9)	0.0272 (9)	0.0522 (12)	−0.0004 (8)	0.0169 (8)	−0.0042 (8)
C25	0.0266 (10)	0.0236 (11)	0.0281 (11)	−0.0014 (9)	0.0093 (8)	−0.0020 (9)
C26	0.0254 (10)	0.0237 (11)	0.0261 (10)	−0.0018 (9)	0.0098 (8)	−0.0005 (8)
C27	0.0244 (10)	0.0241 (11)	0.0240 (10)	−0.0031 (9)	0.0089 (8)	−0.0016 (8)
C28	0.0287 (11)	0.0249 (11)	0.0302 (11)	−0.0022 (9)	0.0105 (9)	−0.0012 (9)
C29	0.0293 (11)	0.0277 (12)	0.0364 (13)	0.0014 (10)	0.0105 (9)	−0.0012 (10)
C30	0.0288 (11)	0.0361 (14)	0.0363 (13)	0.0003 (10)	0.0140 (10)	−0.0044 (11)
C31	0.0295 (11)	0.0331 (13)	0.0300 (11)	−0.0038 (10)	0.0137 (9)	−0.0012 (10)
C32	0.0293 (11)	0.0255 (11)	0.0261 (10)	−0.0036 (9)	0.0111 (9)	−0.0015 (9)
O33	0.0317 (9)	0.0336 (9)	0.0317 (9)	0.0023 (8)	0.0145 (7)	0.0088 (8)
C34	0.0329 (12)	0.0295 (12)	0.0316 (12)	−0.0031 (10)	0.0139 (9)	0.0046 (10)
C35	0.0382 (13)	0.0329 (13)	0.0336 (12)	−0.0050 (11)	0.0118 (10)	0.0026 (11)
O36	0.0379 (10)	0.0381 (11)	0.0405 (10)	−0.0052 (9)	0.0074 (8)	−0.0026 (9)
C37	0.0390 (14)	0.0422 (16)	0.0427 (15)	−0.0061 (13)	0.0042 (12)	0.0122 (13)
C38	0.0405 (15)	0.0318 (14)	0.0543 (17)	−0.0010 (12)	0.0088 (13)	0.0054 (13)
O39	0.0334 (9)	0.0371 (11)	0.0448 (11)	−0.0034 (8)	0.0051 (8)	0.0071 (9)
C40	0.0351 (13)	0.0358 (14)	0.0324 (12)	−0.0018 (11)	0.0048 (10)	0.0008 (11)
C41	0.0403 (13)	0.0349 (13)	0.0270 (11)	−0.0023 (11)	0.0126 (10)	−0.0025 (10)
O42	0.0402 (10)	0.0333 (10)	0.0333 (9)	−0.0066 (8)	0.0190 (8)	−0.0048 (8)
C43	0.0260 (11)	0.0337 (13)	0.0305 (11)	−0.0014 (10)	0.0126 (9)	0.0002 (10)
C44	0.0354 (13)	0.0450 (16)	0.0385 (13)	−0.0044 (12)	0.0208 (11)	−0.0052 (12)
C45	0.0312 (12)	0.0495 (17)	0.0437 (14)	−0.0076 (12)	0.0182 (11)	0.0005 (13)
C46	0.0343 (13)	0.0412 (16)	0.0471 (15)	−0.0120 (12)	0.0149 (12)	−0.0015 (13)
C47	0.0313 (12)	0.0373 (14)	0.0333 (12)	−0.0032 (11)	0.0097 (10)	−0.0012 (11)

C1—C47	1.401 (4)	C24—C25	1.477 (3)
C1—C43	1.402 (4)	C25—C26	1.341 (3)
C1—C2	1.474 (3)	C25—H25	0.9500
C2—C3	1.335 (4)	C26—C27	1.463 (3)
C2—H2	0.9500	C26—H26	0.9500
C3—C4	1.472 (3)	C27—C28	1.402 (3)
C3—H3	0.9500	C27—C32	1.411 (3)
C4—O4	1.222 (3)	C28—C29	1.389 (3)
C4—C5	1.500 (4)	C28—H28	0.9500
C5—C6	1.389 (4)	C29—C30	1.389 (4)
C5—C10	1.405 (3)	C29—H29	0.9500
C6—C7	1.387 (5)	C30—C31	1.397 (4)
C6—H6	0.9500	C30—H30	0.9500
C7—C8	1.376 (5)	C31—C32	1.392 (3)
C7—H7	0.9500	C31—H31	0.9500
C8—C9	1.394 (4)	C32—O33	1.369 (3)
C8—H8	0.9500	O33—C34	1.433 (3)
C9—C10	1.391 (4)	C34—C35	1.504 (4)
C9—H9	0.9500	C34—H34A	0.9900
C10—O11	1.361 (3)	C34—H34B	0.9900
O11—C12	1.440 (3)	C35—O36	1.413 (3)
C12—C13	1.505 (4)	C35—H35A	0.9900
C12—H12A	0.9900	C35—H35B	0.9900
C12—H12B	0.9900	O36—C37	1.435 (4)
C13—O14	1.426 (3)	C37—C38	1.515 (5)
C13—H13A	0.9900	C37—H37A	0.9900
C13—H13B	0.9900	C37—H37B	0.9900
O14—C15	1.418 (3)	C38—O39	1.420 (4)
C15—C16	1.504 (3)	C38—H38A	0.9900
C15—H15A	0.9900	C38—H38B	0.9900
C15—H15B	0.9900	O39—C40	1.417 (3)
C16—O17	1.433 (3)	C40—C41	1.504 (4)
C16—H16A	0.9900	C40—H40A	0.9900
C16—H16B	0.9900	C40—H40B	0.9900
O17—C18	1.358 (3)	C41—O42	1.431 (3)
C18—C19	1.391 (3)	C41—H41A	0.9900
C18—C23	1.407 (3)	C41—H41B	0.9900
C19—C20	1.384 (4)	O42—C43	1.366 (3)
C19—H19	0.9500	C43—C44	1.405 (3)
C20—C21	1.386 (4)	C44—C45	1.390 (4)
C20—H20	0.9500	C44—H44	0.9500
C21—C22	1.388 (4)	C45—C46	1.382 (4)
C21—H21	0.9500	C45—H45	0.9500
C22—C23	1.407 (3)	C46—C47	1.384 (4)
C22—H22	0.9500	C46—H46	0.9500
C23—C24	1.499 (3)	C47—H47	0.9500
C24—O24	1.226 (3)
C47—C1—C43	118.6 (2)	C26—C25—H25	119.7
C47—C1—C2	121.7 (2)	C24—C25—H25	119.7
C43—C1—C2	119.6 (2)	C25—C26—C27	125.1 (2)
C3—C2—C1	124.9 (2)	C25—C26—H26	117.5
C3—C2—H2	117.5	C27—C26—H26	117.5
C1—C2—H2	117.5	C28—C27—C32	118.2 (2)
C2—C3—C4	123.1 (3)	C28—C27—C26	121.8 (2)
C2—C3—H3	118.5	C32—C27—C26	120.0 (2)
C4—C3—H3	118.5	C29—C28—C27	121.3 (2)
O4—C4—C3	119.7 (3)	C29—C28—H28	119.3
O4—C4—C5	120.2 (2)	C27—C28—H28	119.3
C3—C4—C5	120.0 (2)	C30—C29—C28	119.4 (2)
C6—C5—C10	118.7 (3)	C30—C29—H29	120.3
C6—C5—C4	118.6 (2)	C28—C29—H29	120.3
C10—C5—C4	122.6 (2)	C29—C30—C31	120.8 (2)
C7—C6—C5	121.5 (3)	C29—C30—H30	119.6
C7—C6—H6	119.3	C31—C30—H30	119.6
C5—C6—H6	119.3	C32—C31—C30	119.4 (2)
C8—C7—C6	119.3 (3)	C32—C31—H31	120.3
C8—C7—H7	120.3	C30—C31—H31	120.3
C6—C7—H7	120.3	O33—C32—C31	123.7 (2)
C7—C8—C9	120.7 (3)	O33—C32—C27	115.5 (2)
C7—C8—H8	119.7	C31—C32—C27	120.8 (2)
C9—C8—H8	119.7	C32—O33—C34	117.32 (19)
C10—C9—C8	119.9 (3)	O33—C34—C35	107.8 (2)
C10—C9—H9	120.1	O33—C34—H34A	110.2
C8—C9—H9	120.1	C35—C34—H34A	110.2
O11—C10—C9	124.6 (2)	O33—C34—H34B	110.2
O11—C10—C5	115.5 (2)	C35—C34—H34B	110.2
C9—C10—C5	119.9 (2)	H34A—C34—H34B	108.5
C10—O11—C12	117.8 (2)	O36—C35—C34	107.8 (2)
O11—C12—C13	108.4 (2)	O36—C35—H35A	110.1
O11—C12—H12A	110.0	C34—C35—H35A	110.1
C13—C12—H12A	110.0	O36—C35—H35B	110.1
O11—C12—H12B	110.0	C34—C35—H35B	110.1
C13—C12—H12B	110.0	H35A—C35—H35B	108.5
H12A—C12—H12B	108.4	C35—O36—C37	112.1 (2)
O14—C13—C12	114.8 (2)	O36—C37—C38	113.4 (2)
O14—C13—H13A	108.6	O36—C37—H37A	108.9
C12—C13—H13A	108.6	C38—C37—H37A	108.9
O14—C13—H13B	108.6	O36—C37—H37B	108.9
C12—C13—H13B	108.6	C38—C37—H37B	108.9
H13A—C13—H13B	107.6	H37A—C37—H37B	107.7
C15—O14—C13	113.40 (18)	O39—C38—C37	113.9 (3)
O14—C15—C16	108.72 (19)	O39—C38—H38A	108.8
O14—C15—H15A	109.9	C37—C38—H38A	108.8
C16—C15—H15A	109.9	O39—C38—H38B	108.8
O14—C15—H15B	109.9	C37—C38—H38B	108.8
C16—C15—H15B	109.9	H38A—C38—H38B	107.7
H15A—C15—H15B	108.3	C40—O39—C38	114.8 (2)
O17—C16—C15	105.9 (2)	O39—C40—C41	107.8 (2)
O17—C16—H16A	110.6	O39—C40—H40A	110.1
C15—C16—H16A	110.6	C41—C40—H40A	110.1
O17—C16—H16B	110.6	O39—C40—H40B	110.1
C15—C16—H16B	110.6	C41—C40—H40B	110.1
H16A—C16—H16B	108.7	H40A—C40—H40B	108.5
C18—O17—C16	119.23 (19)	O42—C41—C40	108.8 (2)
O17—C18—C19	124.0 (2)	O42—C41—H41A	109.9
O17—C18—C23	115.7 (2)	C40—C41—H41A	109.9
C19—C18—C23	120.2 (2)	O42—C41—H41B	109.9
C20—C19—C18	119.8 (3)	C40—C41—H41B	109.9
C20—C19—H19	120.1	H41A—C41—H41B	108.3
C18—C19—H19	120.1	C43—O42—C41	117.28 (19)
C19—C20—C21	121.2 (3)	O42—C43—C1	117.1 (2)
C19—C20—H20	119.4	O42—C43—C44	122.8 (2)
C21—C20—H20	119.4	C1—C43—C44	120.1 (2)
C20—C21—C22	119.1 (2)	C45—C44—C43	119.8 (3)
C20—C21—H21	120.4	C45—C44—H44	120.1
C22—C21—H21	120.4	C43—C44—H44	120.1
C21—C22—C23	121.0 (3)	C46—C45—C44	120.3 (3)
C21—C22—H22	119.5	C46—C45—H45	119.8
C23—C22—H22	119.5	C44—C45—H45	119.8
C22—C23—C18	118.5 (2)	C45—C46—C47	120.1 (3)
C22—C23—C24	117.5 (2)	C45—C46—H46	120.0
C18—C23—C24	124.0 (2)	C47—C46—H46	120.0
O24—C24—C25	120.9 (2)	C46—C47—C1	121.1 (3)
O24—C24—C23	119.0 (2)	C46—C47—H47	119.5
C25—C24—C23	120.1 (2)	C1—C47—H47	119.5
C26—C25—C24	120.7 (2)
C47—C1—C2—C3	1.0 (4)	C22—C23—C24—C25	−153.5 (2)
C43—C1—C2—C3	−175.4 (3)	C18—C23—C24—C25	27.4 (3)
C1—C2—C3—C4	178.7 (2)	O24—C24—C25—C26	20.1 (4)
C2—C3—C4—O4	169.5 (3)	C23—C24—C25—C26	−162.1 (2)
C2—C3—C4—C5	−7.0 (4)	C24—C25—C26—C27	−177.5 (2)
O4—C4—C5—C6	−62.2 (4)	C25—C26—C27—C28	24.2 (4)
C3—C4—C5—C6	114.2 (3)	C25—C26—C27—C32	−156.2 (2)
O4—C4—C5—C10	117.0 (3)	C32—C27—C28—C29	−1.2 (4)
C3—C4—C5—C10	−66.5 (3)	C26—C27—C28—C29	178.4 (2)
C10—C5—C6—C7	1.7 (4)	C27—C28—C29—C30	0.3 (4)
C4—C5—C6—C7	−179.1 (2)	C28—C29—C30—C31	0.5 (4)
C5—C6—C7—C8	−1.1 (4)	C29—C30—C31—C32	−0.3 (4)
C6—C7—C8—C9	−0.5 (4)	C30—C31—C32—O33	177.9 (2)
C7—C8—C9—C10	1.6 (5)	C30—C31—C32—C27	−0.6 (4)
C8—C9—C10—O11	−179.8 (3)	C28—C27—C32—O33	−177.2 (2)
C8—C9—C10—C5	−1.0 (4)	C26—C27—C32—O33	3.1 (3)
C6—C5—C10—O11	178.3 (2)	C28—C27—C32—C31	1.4 (3)
C4—C5—C10—O11	−0.9 (3)	C26—C27—C32—C31	−178.3 (2)
C6—C5—C10—C9	−0.6 (4)	C31—C32—O33—C34	−4.8 (3)
C4—C5—C10—C9	−179.8 (2)	C27—C32—O33—C34	173.7 (2)
C9—C10—O11—C12	3.0 (4)	C32—O33—C34—C35	−170.8 (2)
C5—C10—O11—C12	−175.9 (2)	O33—C34—C35—O36	72.6 (3)
C10—O11—C12—C13	176.5 (2)	C34—C35—O36—C37	−177.4 (2)
O11—C12—C13—O14	86.1 (3)	C35—O36—C37—C38	88.0 (3)
C12—C13—O14—C15	−69.8 (3)	O36—C37—C38—O39	71.8 (3)
C13—O14—C15—C16	−171.1 (2)	C37—C38—O39—C40	−81.9 (3)
O14—C15—C16—O17	−67.8 (3)	C38—O39—C40—C41	−172.4 (2)
C15—C16—O17—C18	179.1 (2)	O39—C40—C41—O42	−79.6 (3)
C16—O17—C18—C19	11.0 (3)	C40—C41—O42—C43	−172.9 (2)
C16—O17—C18—C23	−171.5 (2)	C41—O42—C43—C1	159.6 (2)
O17—C18—C19—C20	175.6 (2)	C41—O42—C43—C44	−20.9 (4)
C23—C18—C19—C20	−1.7 (4)	C47—C1—C43—O42	179.0 (2)
C18—C19—C20—C21	0.0 (4)	C2—C1—C43—O42	−4.5 (3)
C19—C20—C21—C22	−0.2 (4)	C47—C1—C43—C44	−0.6 (4)
C20—C21—C22—C23	1.9 (4)	C2—C1—C43—C44	175.9 (2)
C21—C22—C23—C18	−3.5 (4)	O42—C43—C44—C45	−179.9 (3)
C21—C22—C23—C24	177.4 (2)	C1—C43—C44—C45	−0.4 (4)
O17—C18—C23—C22	−174.1 (2)	C43—C44—C45—C46	1.2 (5)
C19—C18—C23—C22	3.4 (3)	C44—C45—C46—C47	−1.0 (5)
O17—C18—C23—C24	4.9 (3)	C45—C46—C47—C1	0.0 (4)
C19—C18—C23—C24	−177.6 (2)	C43—C1—C47—C46	0.8 (4)
C22—C23—C24—O24	24.2 (3)	C2—C1—C47—C46	−175.7 (3)
C18—C23—C24—O24	−154.8 (2)