7,11,15,28-Tetra-kis[(2-formyl-phen-oxy)methyl]-1,21,23,25-tetra-methyl-resorcin[4]arene cavitand ethyl acetate clathrate at 173 K.

The title compound, C(68)H(56)O(16), was synthesized as a novel synthetic inter-mediate towards deeper and more elaborate resorcin[4]arene cavitands. The structure is the first reported example of a resorcin[4]arene cavitand bearing aromatic aldehyde functional groups at the extra-annular rim of the mol-ecule. The 2-formyl-phen-oxy residues are found to assume two different orientations above the mol-ecular cavity. One half of the resorcin[4]arene cavitand mol-ecule appears in the asymmetric unit; the complete resorcin[4]arene cavitand structure was generated across a mirror plane. In addition, a highly disordered ethyl acetate solvent mol-ecule is present within the mol-ecular cavity.

Related literature

For literature pertaining to the preparation of precursors to the reported compound, see: Middel et al. (2001 ▶); Sorrell & Pigge (1993 ▶). For related literature on synthetic analogues and other precursors which illustrate the host capabilities of resorcin[4]arene cavitand molecules, see: Friedrich et al. (2007 ▶); Mc Kay et al. (2007 ▶, 2008 ▶). For the implemetation of the SQUEEZE function in PLATON, see: Tam et al. (2005 ▶).

Experimental

Crystal data

C68H56O16

M = 1183.17

Monoclinic,

a = 11.9228 (7) Å

b = 23.2806 (15) Å

c = 12.2320 (7) Å

β = 117.005 (3)°

V = 3025.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.37 × 0.34 × 0.26 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: integration (SAINT-NT; Bruker, 2005 ▶) T min = 0.967, T max = 0.977

24858 measured reflections

5470 independent reflections

3556 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.230

S = 1.11

5470 reflections

417 parameters

21 restraints

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809007582/fl2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007582/fl2233Isup2.hkl

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

C68H56O16	Z = 2
Mr = 1183.17	F(000) = 1238
Monoclinic, P21/m	Dx = 1.261 Mg m−3
Hall symbol: -P 2yb	Melting point: 400 K
a = 11.9228 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 23.2806 (15) Å	µ = 0.09 mm−1
c = 12.2320 (7) Å	T = 173 K
β = 117.005 (3)°	Block, colourless
V = 3025.0 (3) Å3	0.37 × 0.34 × 0.26 mm

Bruker APEXII CCD area-detector diffractometer	5470 independent reflections
Radiation source: fine-focus sealed tube	3556 reflections with I > 2σ(I)
graphite	Rint = 0.079
phi and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: integration (SAINT-NT; Bruker, 2005)	h = −14→13
Tmin = 0.967, Tmax = 0.977	k = −27→27
24858 measured reflections	l = −14→14

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1125P)2 + 0.9365P] where P = (Fo2 + 2Fc2)/3
5470 reflections	(Δ/σ)max < 0.001
417 parameters	Δρmax = 0.64 e Å−3
21 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.0864 (2)	0.19966 (13)	0.2854 (2)	0.0789 (7)
O2	0.0149 (2)	0.04856 (13)	0.4185 (2)	0.0841 (8)
O3	0.2250 (2)	0.05596 (10)	0.3626 (2)	0.0684 (6)
O4	0.4399 (2)	0.05649 (11)	0.4109 (2)	0.0724 (7)
O5	0.6322 (6)	0.1273 (4)	0.6538 (3)	0.0687 (14)	0.789 (4)
O6	0.7467 (2)	0.19955 (12)	0.4748 (2)	0.0717 (7)
C1	−0.0852 (6)	0.2500	−0.0474 (5)	0.108 (2)
H1A	−0.1344	0.2156	−0.0867	0.162*	0.50
H1B	−0.0074	0.2500	−0.0560	0.162*
H1C	−0.1344	0.2844	−0.0867	0.162*	0.50
C2	−0.0529 (5)	0.2500	0.0879 (4)	0.0759 (15)
H2	−0.1348	0.2500	0.0921	0.091*
C3	0.0185 (3)	0.19689 (17)	0.1568 (3)	0.0638 (9)
C4	0.1057 (3)	0.16939 (15)	0.1293 (3)	0.0612 (9)
H4	0.1182	0.1834	0.0627	0.073*
C5	0.1755 (3)	0.12235 (15)	0.1947 (3)	0.0595 (8)
C6	0.1587 (3)	0.10305 (15)	0.2943 (3)	0.0618 (8)
C7	0.0711 (3)	0.12873 (17)	0.3245 (3)	0.0651 (9)
C8	0.0030 (3)	0.17497 (17)	0.2554 (3)	0.0667 (9)
C10	−0.0484 (5)	0.2500	0.3569 (5)	0.0784 (15)
H10A	−0.0846	0.2500	0.4155	0.094*
H10B	0.0444	0.2500	0.4051	0.094*
C11	0.0564 (3)	0.10681 (18)	0.4335 (3)	0.0758 (10)
H11A	0.1382	0.1099	0.5081	0.091*
H11B	−0.0051	0.1312	0.4456	0.091*
C12	0.3502 (3)	0.06610 (17)	0.4547 (3)	0.0679 (9)
H12A	0.3574	0.1063	0.4837	0.081*
H12B	0.3687	0.0405	0.5254	0.081*
C13	0.4750 (3)	0.10434 (15)	0.3670 (3)	0.0624 (9)
C14	0.4015 (3)	0.12373 (14)	0.2479 (3)	0.0577 (8)
C15	0.2761 (4)	0.09540 (16)	0.1678 (3)	0.0698 (9)
H15	0.2839	0.0545	0.1954	0.084*
C16	0.2419 (5)	0.0937 (2)	0.0314 (4)	0.0927 (13)
H16A	0.3103	0.0754	0.0205	0.139*
H16B	0.2292	0.1329	−0.0010	0.139*
H16C	0.1642	0.0716	−0.0128	0.139*
C17	0.4452 (3)	0.17050 (14)	0.2087 (3)	0.0576 (8)
H17	0.3953	0.1847	0.1281	0.069*
C18	0.5590 (3)	0.19770 (14)	0.2820 (3)	0.0560 (8)
C19	0.6293 (3)	0.17645 (16)	0.3996 (3)	0.0618 (9)
C20	0.5909 (3)	0.12927 (15)	0.4442 (3)	0.0610 (8)
C21	0.6021 (5)	0.2500	0.2383 (4)	0.0624 (12)
H21	0.6962	0.2500	0.2838	0.075*
C22	0.5690 (6)	0.2500	0.1040 (5)	0.0819 (16)
H22A	0.6040	0.2156	0.0847	0.123*	0.50
H22B	0.6040	0.2844	0.0847	0.123*	0.50
H22C	0.4774	0.2500	0.0551	0.123*
C23	0.7479 (5)	0.2500	0.5390 (5)	0.0751 (15)
H23A	0.6736	0.2500	0.5549	0.090*
H23B	0.8242	0.2500	0.6193	0.090*
C24	−0.1063 (3)	0.03514 (18)	0.3420 (3)	0.0698 (10)
C25	−0.1265 (3)	−0.02235 (19)	0.3029 (3)	0.0724 (10)
C26	−0.2490 (4)	−0.04163 (19)	0.2342 (3)	0.0790 (11)
H26	−0.2640	−0.0807	0.2096	0.095*
C27	−0.3492 (4)	−0.0044 (2)	0.2014 (4)	0.0877 (12)
H27	−0.4331	−0.0175	0.1540	0.105*
C28	−0.3259 (4)	0.0512 (2)	0.2380 (4)	0.0853 (12)
H28	−0.3951	0.0767	0.2145	0.102*
C29	−0.2063 (3)	0.07220 (19)	0.3078 (3)	0.0759 (10)
H29	−0.1932	0.1114	0.3316	0.091*
C30	−0.0200 (4)	−0.0605 (2)	0.3320 (4)	0.0855 (12)
H30	0.0624	−0.0453	0.3772	0.103*
O31	−0.0307 (3)	−0.11081 (18)	0.3016 (3)	0.1079 (10)
C32	0.6930 (10)	0.1091 (4)	0.7722 (4)	0.0610 (12)	0.789 (4)
C33	0.6320 (4)	0.1178 (2)	0.8485 (4)	0.0651 (12)	0.789 (4)
C34	0.6952 (5)	0.1003 (2)	0.9714 (4)	0.0819 (15)	0.789 (4)
H34	0.6588	0.1078	1.0247	0.098*	0.789 (4)
C35	0.8071 (9)	0.0730 (3)	1.0151 (6)	0.086 (3)	0.789 (4)
H35	0.8481	0.0609	1.0984	0.103*	0.789 (4)
C36	0.8608 (5)	0.0627 (3)	0.9406 (6)	0.084 (2)	0.789 (4)
H36	0.9401	0.0438	0.9729	0.101*	0.789 (4)
C37	0.8035 (4)	0.0789 (2)	0.8188 (5)	0.0721 (17)	0.789 (4)
H37	0.8408	0.0691	0.7672	0.086*	0.789 (4)
C38	0.5084 (5)	0.1450 (2)	0.8038 (4)	0.0801 (14)	0.789 (4)
H38	0.4685	0.1578	0.7210	0.096*	0.789 (4)
O39	0.4540 (4)	0.1522 (2)	0.8650 (4)	0.1058 (14)	0.789 (4)
O5A	0.615 (3)	0.1252 (18)	0.6415 (18)	0.076 (2)*	0.211 (4)
C32A	0.687 (5)	0.1056 (19)	0.7573 (19)	0.076 (2)*	0.211 (4)
C33A	0.6917 (17)	0.1491 (7)	0.8415 (13)	0.076 (2)*	0.211 (4)
C34A	0.7500 (17)	0.1340 (8)	0.9670 (14)	0.076 (2)*	0.211 (4)
H34A	0.7415	0.1584	1.0251	0.091*	0.211 (4)
C35A	0.817 (4)	0.0855 (13)	1.005 (2)	0.076 (2)*	0.211 (4)
H35A	0.8562	0.0760	1.0897	0.091*	0.211 (4)
C36A	0.829 (3)	0.0498 (11)	0.924 (2)	0.076 (2)*	0.211 (4)
H36A	0.8768	0.0154	0.9523	0.091*	0.211 (4)
C37A	0.774 (2)	0.0625 (10)	0.800 (2)	0.076 (2)*	0.211 (4)
H37A	0.7967	0.0419	0.7455	0.091*	0.211 (4)
C38A	0.6207 (16)	0.2018 (7)	0.7993 (15)	0.076 (2)*	0.211 (4)
H38A	0.5835	0.2110	0.7145	0.091*	0.211 (4)
O39A	0.6082 (10)	0.2326 (4)	0.8661 (10)	0.076 (2)*	0.211 (4)
C40	0.6725 (3)	0.10524 (18)	0.5674 (3)	0.0732 (10)
H40A	0.6669	0.0628	0.5648	0.088*
H40B	0.7613	0.1162	0.5932	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.0513 (13)	0.109 (2)	0.0848 (17)	−0.0066 (13)	0.0381 (12)	−0.0015 (15)
O2	0.0592 (14)	0.110 (2)	0.0818 (17)	−0.0194 (14)	0.0305 (13)	0.0159 (15)
O3	0.0759 (15)	0.0721 (15)	0.0636 (13)	−0.0104 (12)	0.0372 (12)	0.0058 (12)
O4	0.0813 (15)	0.0676 (15)	0.0778 (15)	0.0124 (12)	0.0445 (13)	0.0155 (12)
O5	0.060 (3)	0.085 (3)	0.0437 (17)	0.024 (3)	0.0084 (17)	0.0045 (18)
O6	0.0500 (12)	0.0983 (19)	0.0715 (14)	0.0077 (12)	0.0317 (11)	0.0066 (14)
C1	0.093 (4)	0.131 (6)	0.064 (3)	0.000	0.004 (3)	0.000
C2	0.051 (3)	0.105 (4)	0.055 (3)	0.000	0.009 (2)	0.000
C3	0.0461 (16)	0.089 (3)	0.0461 (16)	−0.0079 (16)	0.0124 (14)	−0.0023 (16)
C4	0.0585 (18)	0.083 (2)	0.0351 (15)	−0.0130 (17)	0.0152 (13)	−0.0064 (15)
C5	0.0605 (18)	0.075 (2)	0.0435 (16)	−0.0131 (17)	0.0243 (14)	−0.0125 (16)
C6	0.0603 (18)	0.072 (2)	0.0500 (17)	−0.0151 (16)	0.0220 (15)	−0.0022 (16)
C7	0.0482 (16)	0.090 (3)	0.0596 (19)	−0.0192 (17)	0.0264 (15)	−0.0011 (18)
C8	0.0468 (17)	0.090 (3)	0.0603 (19)	−0.0107 (17)	0.0215 (15)	−0.0037 (19)
C10	0.061 (3)	0.110 (5)	0.079 (3)	0.000	0.045 (3)	0.000
C11	0.065 (2)	0.099 (3)	0.069 (2)	−0.019 (2)	0.0360 (18)	0.006 (2)
C12	0.071 (2)	0.078 (2)	0.061 (2)	−0.0017 (18)	0.0345 (17)	0.0129 (18)
C13	0.072 (2)	0.062 (2)	0.070 (2)	0.0124 (17)	0.0477 (18)	0.0089 (17)
C14	0.0650 (18)	0.067 (2)	0.0520 (17)	0.0070 (16)	0.0365 (15)	−0.0007 (15)
C15	0.088 (2)	0.072 (2)	0.0560 (19)	−0.0051 (19)	0.0382 (18)	−0.0074 (17)
C16	0.117 (3)	0.108 (3)	0.061 (2)	−0.013 (3)	0.048 (2)	−0.018 (2)
C17	0.0688 (19)	0.072 (2)	0.0451 (16)	0.0073 (16)	0.0370 (15)	0.0013 (15)
C18	0.0601 (18)	0.067 (2)	0.0564 (17)	0.0081 (15)	0.0404 (15)	0.0012 (15)
C19	0.0542 (17)	0.082 (2)	0.0614 (19)	0.0096 (16)	0.0366 (16)	0.0044 (17)
C20	0.0608 (19)	0.071 (2)	0.0608 (18)	0.0176 (16)	0.0364 (16)	0.0126 (16)
C21	0.067 (3)	0.082 (3)	0.056 (2)	0.000	0.044 (2)	0.000
C22	0.106 (4)	0.091 (4)	0.079 (3)	0.000	0.068 (3)	0.000
C23	0.054 (3)	0.111 (5)	0.062 (3)	0.000	0.028 (2)	0.000
C24	0.066 (2)	0.095 (3)	0.062 (2)	−0.0045 (19)	0.0404 (17)	0.0028 (19)
C25	0.064 (2)	0.108 (3)	0.060 (2)	0.000 (2)	0.0416 (17)	−0.004 (2)
C26	0.076 (2)	0.097 (3)	0.069 (2)	−0.002 (2)	0.0376 (19)	−0.022 (2)
C27	0.057 (2)	0.115 (4)	0.088 (3)	−0.005 (2)	0.0306 (19)	−0.026 (3)
C28	0.065 (2)	0.100 (3)	0.101 (3)	−0.005 (2)	0.046 (2)	−0.027 (2)
C29	0.062 (2)	0.093 (3)	0.083 (2)	−0.0054 (19)	0.0419 (19)	−0.017 (2)
C30	0.082 (3)	0.113 (4)	0.080 (3)	0.017 (3)	0.052 (2)	0.007 (3)
O31	0.112 (2)	0.121 (3)	0.107 (2)	0.028 (2)	0.064 (2)	0.005 (2)
C32	0.054 (2)	0.064 (3)	0.046 (2)	−0.002 (2)	0.006 (2)	−0.011 (2)
C33	0.067 (3)	0.069 (3)	0.051 (2)	−0.005 (2)	0.020 (2)	−0.011 (2)
C34	0.092 (4)	0.092 (4)	0.046 (2)	0.003 (3)	0.018 (2)	−0.003 (2)
C35	0.099 (5)	0.089 (5)	0.042 (3)	−0.005 (4)	0.008 (3)	0.005 (3)
C36	0.066 (4)	0.093 (5)	0.067 (3)	0.008 (3)	0.006 (3)	0.007 (3)
C37	0.054 (3)	0.095 (4)	0.060 (3)	0.009 (3)	0.019 (2)	0.010 (3)
C38	0.073 (3)	0.105 (4)	0.068 (3)	−0.005 (3)	0.037 (2)	−0.011 (3)
O39	0.102 (3)	0.140 (4)	0.095 (3)	0.003 (2)	0.062 (2)	−0.012 (2)
C40	0.0610 (19)	0.094 (3)	0.070 (2)	0.0192 (18)	0.0347 (17)	0.021 (2)

O1—C8	1.399 (4)	C22—H22B	0.9800
O1—C10	1.409 (4)	C22—H22C	0.9800
O2—C24	1.354 (4)	C23—O6i	1.410 (4)
O2—C11	1.426 (5)	C23—H23A	0.9900
O3—C6	1.387 (4)	C23—H23B	0.9900
O3—C12	1.424 (4)	C24—C29	1.374 (5)
O4—C13	1.382 (4)	C24—C25	1.405 (6)
O4—C12	1.414 (4)	C25—C26	1.388 (5)
O6—C19	1.387 (4)	C25—C30	1.455 (6)
O6—C23	1.410 (4)	C26—C27	1.379 (6)
C1—C2	1.519 (8)	C26—H26	0.9500
C1—H1A	0.9800	C27—C28	1.357 (6)
C1—H1B	0.9800	C27—H27	0.9500
C1—H1C	0.9800	C28—C29	1.377 (5)
C2—C3i	1.521 (4)	C28—H28	0.9500
C2—C3	1.521 (4)	C29—H29	0.9500
C2—H2	1.0000	C30—O31	1.218 (5)
C3—C4	1.387 (5)	C30—H30	0.9500
C3—C8	1.397 (5)	O5—C32	1.360 (6)
C4—C5	1.388 (5)	O5—C40	1.439 (4)
C4—H4	0.9500	C32—C37	1.369 (7)
C5—C6	1.396 (4)	C32—C33	1.434 (11)
C5—C15	1.516 (5)	C33—C34	1.402 (6)
C6—C7	1.392 (5)	C33—C38	1.461 (7)
C7—C8	1.382 (5)	C34—C35	1.349 (9)
C7—C11	1.510 (5)	C34—H34	0.9500
C10—O1i	1.409 (4)	C35—C36	1.353 (8)
C10—H10A	0.9900	C35—H35	0.9500
C10—H10B	0.9900	C36—C37	1.380 (7)
C11—H11A	0.9900	C36—H36	0.9500
C11—H11B	0.9900	C37—H37	0.9500
C12—H12A	0.9900	C38—O39	1.205 (5)
C12—H12B	0.9900	C38—H38	0.9500
C13—C14	1.391 (5)	O5A—C32A	1.359 (16)
C13—C20	1.397 (5)	O5A—C40	1.439 (6)
C14—C17	1.383 (5)	C32A—C37A	1.367 (16)
C14—C15	1.516 (5)	C32A—C33A	1.43 (2)
C15—C16	1.528 (5)	C33A—C34A	1.413 (15)
C15—H15	1.0000	C33A—C38A	1.445 (16)
C16—H16A	0.9800	C34A—C35A	1.338 (17)
C16—H16B	0.9800	C34A—H34A	0.9500
C16—H16C	0.9800	C35A—C36A	1.354 (18)
C17—C18	1.393 (5)	C35A—H35A	0.9500
C17—H17	0.9500	C36A—C37A	1.383 (17)
C18—C19	1.386 (4)	C36A—H36A	0.9500
C18—C21	1.511 (4)	C37A—H37A	0.9500
C19—C20	1.393 (5)	C38A—O39A	1.147 (14)
C20—C40	1.483 (5)	C38A—H38A	0.9500
C21—C22	1.505 (7)	O39A—O39Ai	0.81 (2)
C21—C18i	1.511 (4)	O39A—C38Ai	1.769 (18)
C21—H21	1.0000	C40—H40A	0.9900
C22—H22A	0.9800	C40—H40B	0.9900
C8—O1—C10	115.9 (3)	C21—C22—H22A	109.5
C24—O2—C11	120.5 (3)	C21—C22—H22B	109.5
C6—O3—C12	116.8 (3)	H22A—C22—H22B	109.5
C13—O4—C12	115.8 (3)	C21—C22—H22C	109.5
C19—O6—C23	116.4 (3)	H22A—C22—H22C	109.5
C2—C1—H1A	109.5	H22B—C22—H22C	109.5
C2—C1—H1B	109.5	O6i—C23—O6	112.9 (4)
H1A—C1—H1B	109.5	O6i—C23—H23A	109.0
C2—C1—H1C	109.5	O6—C23—H23A	109.0
H1A—C1—H1C	109.5	O6i—C23—H23B	109.0
H1B—C1—H1C	109.5	O6—C23—H23B	109.0
C1—C2—C3i	113.9 (3)	H23A—C23—H23B	107.8
C1—C2—C3	113.9 (3)	O2—C24—C29	124.9 (4)
C3i—C2—C3	108.8 (4)	O2—C24—C25	114.8 (3)
C1—C2—H2	106.6	C29—C24—C25	120.2 (3)
C3i—C2—H2	106.6	C26—C25—C24	119.0 (4)
C3—C2—H2	106.6	C26—C25—C30	120.8 (4)
C4—C3—C8	116.7 (3)	C24—C25—C30	120.2 (4)
C4—C3—C2	122.2 (3)	C27—C26—C25	120.5 (4)
C8—C3—C2	121.0 (4)	C27—C26—H26	119.7
C3—C4—C5	123.0 (3)	C25—C26—H26	119.7
C3—C4—H4	118.5	C28—C27—C26	118.8 (4)
C5—C4—H4	118.5	C28—C27—H27	120.6
C4—C5—C6	118.1 (3)	C26—C27—H27	120.6
C4—C5—C15	121.9 (3)	C27—C28—C29	122.9 (4)
C6—C5—C15	119.8 (3)	C27—C28—H28	118.6
O3—C6—C7	118.1 (3)	C29—C28—H28	118.6
O3—C6—C5	120.8 (3)	C24—C29—C28	118.5 (4)
C7—C6—C5	121.1 (3)	C24—C29—H29	120.8
C8—C7—C6	118.4 (3)	C28—C29—H29	120.8
C8—C7—C11	122.2 (3)	O31—C30—C25	123.6 (4)
C6—C7—C11	119.4 (3)	O31—C30—H30	118.2
C7—C8—C3	122.8 (3)	C25—C30—H30	118.2
C7—C8—O1	117.7 (3)	C32—O5—C40	118.5 (5)
C3—C8—O1	119.4 (3)	O5—C32—C37	123.3 (8)
O1i—C10—O1	112.6 (4)	O5—C32—C33	117.8 (6)
O1i—C10—H10A	109.1	C37—C32—C33	118.6 (6)
O1—C10—H10A	109.1	C34—C33—C32	118.1 (4)
O1i—C10—H10B	109.1	C34—C33—C38	119.2 (4)
O1—C10—H10B	109.1	C32—C33—C38	122.7 (4)
H10A—C10—H10B	107.8	C35—C34—C33	121.1 (5)
O2—C11—C7	112.3 (3)	C35—C34—H34	119.4
O2—C11—H11A	109.1	C33—C34—H34	119.4
C7—C11—H11A	109.1	C34—C35—C36	120.1 (5)
O2—C11—H11B	109.1	C34—C35—H35	120.0
C7—C11—H11B	109.1	C36—C35—H35	120.0
H11A—C11—H11B	107.9	C35—C36—C37	121.7 (5)
O4—C12—O3	112.1 (3)	C35—C36—H36	119.1
O4—C12—H12A	109.2	C37—C36—H36	119.1
O3—C12—H12A	109.2	C32—C37—C36	120.0 (6)
O4—C12—H12B	109.2	C32—C37—H37	120.0
O3—C12—H12B	109.2	C36—C37—H37	120.0
H12A—C12—H12B	107.9	O39—C38—C33	124.3 (5)
O4—C13—C14	120.7 (3)	O39—C38—H38	117.9
O4—C13—C20	117.0 (3)	C33—C38—H38	117.9
C14—C13—C20	122.2 (3)	C32A—O5A—C40	107 (2)
C17—C14—C13	117.4 (3)	O5A—C32A—C37A	130.8 (19)
C17—C14—C15	122.3 (3)	O5A—C32A—C33A	108.2 (19)
C13—C14—C15	120.2 (3)	C37A—C32A—C33A	118 (2)
C5—C15—C14	108.9 (3)	C34A—C33A—C32A	116.4 (15)
C5—C15—C16	113.8 (3)	C34A—C33A—C38A	121.3 (14)
C14—C15—C16	114.4 (3)	C32A—C33A—C38A	121.3 (14)
C5—C15—H15	106.4	C35A—C34A—C33A	120.6 (16)
C14—C15—H15	106.4	C35A—C34A—H34A	119.7
C16—C15—H15	106.4	C33A—C34A—H34A	119.7
C15—C16—H16A	109.5	C34A—C35A—C36A	120.7 (19)
C15—C16—H16B	109.5	C34A—C35A—H35A	119.7
H16A—C16—H16B	109.5	C36A—C35A—H35A	119.7
C15—C16—H16C	109.5	C35A—C36A—C37A	121.2 (19)
H16A—C16—H16C	109.5	C35A—C36A—H36A	119.4
H16B—C16—H16C	109.5	C37A—C36A—H36A	119.4
C14—C17—C18	123.0 (3)	C32A—C37A—C36A	118.3 (19)
C14—C17—H17	118.5	C32A—C37A—H37A	120.9
C18—C17—H17	118.5	C36A—C37A—H37A	120.9
C19—C18—C17	117.4 (3)	O39A—C38A—C33A	121.4 (15)
C19—C18—C21	120.8 (3)	O39A—C38A—H38A	119.3
C17—C18—C21	121.8 (3)	C33A—C38A—H38A	119.3
C18—C19—O6	120.1 (3)	O39Ai—O39A—C38A	128.8 (10)
C18—C19—C20	122.4 (3)	C38A—O39A—C38Ai	98.4 (15)
O6—C19—C20	117.3 (3)	O5A—C40—C20	103.8 (10)
C19—C20—C13	117.6 (3)	O5—C40—C20	109.1 (3)
C19—C20—C40	121.0 (3)	O5A—C40—H40A	107.3
C13—C20—C40	121.4 (3)	O5—C40—H40A	109.9
C22—C21—C18i	115.1 (3)	C20—C40—H40A	109.9
C22—C21—C18	115.1 (3)	O5A—C40—H40B	117.5
C18i—C21—C18	107.4 (3)	O5—C40—H40B	109.9
C22—C21—H21	106.2	C20—C40—H40B	109.9
C18i—C21—H21	106.2	H40A—C40—H40B	108.3
C18—C21—H21	106.2
C1—C2—C3—C4	35.0 (5)	C14—C13—C20—C19	2.5 (5)
C3i—C2—C3—C4	−93.2 (4)	O4—C13—C20—C40	0.3 (4)
C1—C2—C3—C8	−148.0 (4)	C14—C13—C20—C40	−175.3 (3)
C3i—C2—C3—C8	83.8 (5)	C19—C18—C21—C22	146.8 (4)
C8—C3—C4—C5	0.0 (5)	C17—C18—C21—C22	−36.1 (5)
C2—C3—C4—C5	177.2 (3)	C19—C18—C21—C18i	−83.7 (4)
C3—C4—C5—C6	−1.6 (5)	C17—C18—C21—C18i	93.4 (4)
C3—C4—C5—C15	−176.1 (3)	C19—O6—C23—O6i	−92.0 (4)
C12—O3—C6—C7	−101.0 (3)	C11—O2—C24—C29	−24.0 (5)
C12—O3—C6—C5	81.8 (4)	C11—O2—C24—C25	159.5 (3)
C4—C5—C6—O3	179.5 (3)	O2—C24—C25—C26	173.7 (3)
C15—C5—C6—O3	−5.9 (5)	C29—C24—C25—C26	−3.0 (5)
C4—C5—C6—C7	2.4 (5)	O2—C24—C25—C30	−7.6 (5)
C15—C5—C6—C7	177.0 (3)	C29—C24—C25—C30	175.6 (3)
O3—C6—C7—C8	−178.8 (3)	C24—C25—C26—C27	2.1 (5)
C5—C6—C7—C8	−1.7 (5)	C30—C25—C26—C27	−176.5 (4)
O3—C6—C7—C11	3.3 (5)	C25—C26—C27—C28	−0.4 (6)
C5—C6—C7—C11	−179.6 (3)	C26—C27—C28—C29	−0.6 (7)
C6—C7—C8—C3	0.0 (5)	O2—C24—C29—C28	−174.3 (3)
C11—C7—C8—C3	177.9 (3)	C25—C24—C29—C28	2.1 (5)
C6—C7—C8—O1	178.8 (3)	C27—C28—C29—C24	−0.2 (6)
C11—C7—C8—O1	−3.3 (5)	C26—C25—C30—O31	−1.8 (6)
C4—C3—C8—C7	0.8 (5)	C24—C25—C30—O31	179.6 (4)
C2—C3—C8—C7	−176.4 (3)	C40—O5—C32—C37	11.7 (17)
C4—C3—C8—O1	−178.0 (3)	C40—O5—C32—C33	−162.8 (8)
C2—C3—C8—O1	4.8 (5)	O5—C32—C33—C34	−178.7 (8)
C10—O1—C8—C7	99.5 (4)	C37—C32—C33—C34	6.6 (12)
C10—O1—C8—C3	−81.7 (4)	O5—C32—C33—C38	0.3 (13)
C8—O1—C10—O1i	95.5 (4)	C37—C32—C33—C38	−174.4 (7)
C24—O2—C11—C7	−74.8 (4)	C32—C33—C34—C35	−3.8 (10)
C8—C7—C11—O2	119.6 (4)	C38—C33—C34—C35	177.3 (6)
C6—C7—C11—O2	−62.6 (4)	C33—C34—C35—C36	0.9 (11)
C13—O4—C12—O3	93.9 (4)	C34—C35—C36—C37	−0.8 (11)
C6—O3—C12—O4	−93.4 (3)	O5—C32—C37—C36	178.9 (9)
C12—O4—C13—C14	−82.4 (4)	C33—C32—C37—C36	−6.7 (13)
C12—O4—C13—C20	101.9 (3)	C35—C36—C37—C32	3.9 (11)
O4—C13—C14—C17	−177.5 (3)	C34—C33—C38—O39	−2.2 (8)
C20—C13—C14—C17	−2.1 (4)	C32—C33—C38—O39	178.9 (7)
O4—C13—C14—C15	4.9 (4)	C40—O5A—C32A—C37A	−18 (8)
C20—C13—C14—C15	−179.7 (3)	C40—O5A—C32A—C33A	142 (4)
C4—C5—C15—C14	91.1 (3)	O5A—C32A—C33A—C34A	173 (3)
C6—C5—C15—C14	−83.3 (4)	C37A—C32A—C33A—C34A	−24 (6)
C4—C5—C15—C16	−37.8 (5)	O5A—C32A—C33A—C38A	4(6)
C6—C5—C15—C16	147.7 (3)	C37A—C32A—C33A—C38A	167 (3)
C17—C14—C15—C5	−92.5 (3)	C32A—C33A—C34A—C35A	12 (5)
C13—C14—C15—C5	85.0 (4)	C38A—C33A—C34A—C35A	−179 (3)
C17—C14—C15—C16	36.0 (5)	C33A—C34A—C35A—C36A	−1(5)
C13—C14—C15—C16	−146.5 (3)	C34A—C35A—C36A—C37A	0(6)
C13—C14—C17—C18	1.1 (4)	O5A—C32A—C37A—C36A	−177 (6)
C15—C14—C17—C18	178.7 (3)	C33A—C32A—C37A—C36A	24 (7)
C14—C17—C18—C19	−0.6 (4)	C35A—C36A—C37A—C32A	−13 (5)
C14—C17—C18—C21	−177.8 (3)	C34A—C33A—C38A—O39A	−1(3)
C17—C18—C19—O6	176.4 (3)	C32A—C33A—C38A—O39A	168 (4)
C21—C18—C19—O6	−6.4 (4)	C33A—C38A—O39A—O39Ai	141.6 (14)
C17—C18—C19—C20	1.0 (4)	C33A—C38A—O39A—C38Ai	141.6 (14)
C21—C18—C19—C20	178.3 (3)	C32A—O5A—C40—O5	−45 (13)
C23—O6—C19—C18	83.0 (4)	C32A—O5A—C40—C20	−179 (4)
C23—O6—C19—C20	−101.4 (4)	C32—O5—C40—O5A	130 (15)
C18—C19—C20—C13	−1.9 (5)	C32—O5—C40—C20	178.1 (9)
O6—C19—C20—C13	−177.4 (3)	C19—C20—C40—O5A	104.3 (19)
C18—C19—C20—C40	175.8 (3)	C13—C20—C40—O5A	−78.1 (19)
O6—C19—C20—C40	0.3 (4)	C19—C20—C40—O5	98.3 (6)
O4—C13—C20—C19	178.0 (3)	C13—C20—C40—O5	−84.1 (6)