Calixarene-based mol-ecular capsule from olefin metathesis.

The reaction of tetra-kis-(all-yloxy)calix[4]arene with the first-generation Grubbs catalyst, followed by catalytic hydrogenation, gave the novel bis-calixarene 15,20,46,51,64,69,74,79-octa-oxatridecacyclo[32.28.8.8(3,28).1(13,53).1(22,44).0(9,14).0(21,26).0(38,70).0(40,45).0(52,57).0(59,63).0(7,80).0(32,73)]octa-conta-1(63),3,5,7(80),9(14),10,12,21,23,25,28(73),29,31,34,36,38(70),40,42,44,52,54,56,59,61-tetra-cosa-ene benzene monosolvate, C72H72O8·C6H6. The structure consists of two calix[4]arene units connected by four-carbon chains at each of the four O atoms on their narrow rims, to form a cage. Each of the calix[4]arene units has a flattened cone conformation in which two of the opposite aryl groups are closer together and nearly parallel [dihedral angle between planes = 7.35 (16)°], and the other two aryl groups are splayed outward [dihedral angle between planes = 72.20 (8)°]. While the cavity contains no solvent or other guest mol-ecule, there is benzene solvent mol-ecule in the lattice. Two of the alkyl linking arms were disordered over two conformations with occupancies of 0.582 (3)/0.418 (3) and 0.33 (4)/0.467 (4). They were constrained to have similar metrical and thermal parameters.

Related literature

For literature related to the use of calixarenes as easily isolable reaction products, see: Asfari et al. (2001 ▶); Gutsche (2008 ▶). For literature related to the preparation of bridged calixarenes, see: Yang & Swager (2007 ▶); Hailu et al. (2012 ▶). For literature related to the conformation of calixarenes, see: Arduini et al. (1995 ▶, 1996 ▶); Drew et al. (1997 ▶). For literature related to starting material and catalyst used, see: Ho et al. (1996 ▶); Vougioukalakis & Grubbs (2010 ▶).

Experimental

Crystal data

C72H72O8·C6H6

M = 1143.40

Monoclinic,

a = 14.8804 (10) Å

b = 17.3004 (11) Å

c = 12.1888 (8) Å

β = 103.929 (7)°

V = 3045.6 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.62 mm−1

T = 123 K

0.87 × 0.35 × 0.03 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2012 ▶; Clark & Reid, 1995 ▶) T min = 0.795, T max = 0.982

9972 measured reflections

9972 independent reflections

5548 reflections with I > 2σ(I)

R int = 0.000

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.249

S = 1.00

9972 reflections

415 parameters

10 restraints

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014438/hg5315sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014438/hg5315Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014438/hg5315Isup3.cml

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

C72H72O8·C6H6	F(000) = 1220
Mr = 1143.40	Dx = 1.247 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1980 reflections
a = 14.8804 (10) Å	θ = 3.1–75.5°
b = 17.3004 (11) Å	µ = 0.62 mm−1
c = 12.1888 (8) Å	T = 123 K
β = 103.929 (7)°	Plate, colorless
V = 3045.6 (3) Å3	0.87 × 0.35 × 0.03 mm
Z = 2

Agilent Xcalibur (Ruby, Gemini) diffractometer	9972 independent reflections
Radiation source: Enhance (Cu) X-ray Source	5548 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.5081 pixels mm-1	θmax = 75.9°, θmin = 3.1°
ω scans	h = −18→18
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012; Clark & Reid, 1995)	k = −21→21
Tmin = 0.795, Tmax = 0.982	l = −15→14
9972 measured reflections

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.249	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1443P)2] where P = (Fo2 + 2Fc2)/3
9972 reflections	(Δ/σ)max < 0.001
415 parameters	Δρmax = 1.03 e Å−3
10 restraints	Δρmin = −0.24 e Å−3

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2012, Clark & Reid, 1995) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid.

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	0.30199 (13)	0.55520 (14)	0.31841 (19)	0.0602 (6)
O2	0.69820 (13)	0.54928 (11)	0.45949 (17)	0.0472 (5)
O3	0.66583 (12)	0.35803 (11)	0.43693 (17)	0.0492 (5)
O4	0.33639 (13)	0.36946 (12)	0.32522 (19)	0.0568 (6)
C1	0.74710 (18)	0.58325 (17)	0.3899 (3)	0.0485 (7)
C2	0.77581 (19)	0.66002 (18)	0.4122 (3)	0.0573 (8)
C3	0.8277 (2)	0.6930 (2)	0.3425 (3)	0.0691 (11)
H3A	0.8489	0.7447	0.3558	0.083*
C4	0.8488 (2)	0.6516 (3)	0.2543 (3)	0.0747 (11)
H4A	0.8815	0.6757	0.2057	0.090*
C5	0.8222 (2)	0.5757 (3)	0.2378 (3)	0.0691 (10)
H5A	0.8391	0.5472	0.1793	0.083*
C6	0.77098 (19)	0.5396 (2)	0.3047 (3)	0.0557 (8)
C7	0.7496 (2)	0.4546 (2)	0.2948 (3)	0.0567 (8)
H7A	0.7658	0.4337	0.2265	0.068*
H7B	0.6824	0.4466	0.2868	0.068*
C8	0.80383 (19)	0.41190 (17)	0.3989 (3)	0.0493 (7)
C9	0.8995 (2)	0.42163 (18)	0.4304 (3)	0.0531 (7)
H9A	0.9292	0.4513	0.3837	0.064*
C10	0.95165 (19)	0.38909 (18)	0.5278 (3)	0.0564 (8)
H10A	1.0170	0.3956	0.5481	0.068*
C11	0.90806 (19)	0.34675 (18)	0.5961 (3)	0.0555 (8)
H11A	0.9442	0.3245	0.6636	0.067*
C12	0.8129 (2)	0.33586 (16)	0.5687 (3)	0.0516 (7)
C13	0.76157 (18)	0.36740 (16)	0.4673 (3)	0.0459 (6)
C14	0.7682 (2)	0.29599 (19)	0.6526 (3)	0.0672 (10)
H14A	0.7002	0.2949	0.6225	0.081*
H14B	0.7905	0.2420	0.6636	0.081*
C15	0.6360 (3)	0.2828 (3)	0.3918 (5)	0.0497 (11)	0.582 (3)
H15A	0.6652	0.2422	0.4459	0.060*	0.582 (3)
H15B	0.6549	0.2746	0.3201	0.060*	0.582 (3)
C16	0.5311 (4)	0.2779 (3)	0.3707 (4)	0.0532 (10)	0.582 (3)
H16A	0.5128	0.2229	0.3587	0.064*	0.582 (3)
H16B	0.5133	0.2954	0.4398	0.064*	0.582 (3)
C17	0.4767 (4)	0.3238 (3)	0.2723 (5)	0.0580 (11)	0.582 (3)
H17A	0.4944	0.3789	0.2850	0.070*	0.582 (3)
H17D	0.4955	0.3069	0.2035	0.070*	0.582 (3)
C18	0.3738 (4)	0.3183 (4)	0.2498 (6)	0.0591 (14)	0.582 (3)
H18A	0.3462	0.3325	0.1702	0.071*	0.582 (3)
H18B	0.3562	0.2642	0.2609	0.071*	0.582 (3)
C15B	0.6356 (4)	0.3113 (4)	0.3308 (7)	0.0497 (11)	0.418 (3)
H15C	0.6513	0.2562	0.3466	0.060*	0.418 (3)
H15D	0.6675	0.3297	0.2731	0.060*	0.418 (3)
C16B	0.5309 (5)	0.3207 (4)	0.2876 (6)	0.0532 (10)	0.418 (3)
H16C	0.5172	0.3767	0.2784	0.064*	0.418 (3)
H16D	0.5124	0.2970	0.2116	0.064*	0.418 (3)
C17B	0.4721 (5)	0.2880 (5)	0.3568 (7)	0.0580 (11)	0.418 (3)
H17B	0.4868	0.3150	0.4306	0.070*	0.418 (3)
H17C	0.4895	0.2331	0.3715	0.070*	0.418 (3)
C18B	0.3699 (5)	0.2917 (5)	0.3101 (8)	0.0591 (14)	0.418 (3)
H18C	0.3548	0.2785	0.2287	0.071*	0.418 (3)
H18D	0.3389	0.2538	0.3494	0.071*	0.418 (3)
C19	0.23955 (18)	0.37101 (16)	0.3028 (3)	0.0508 (7)
C20	0.1945 (2)	0.33526 (16)	0.3766 (3)	0.0513 (7)
C21	0.0987 (2)	0.33485 (18)	0.3495 (3)	0.0564 (8)
H21A	0.0670	0.3099	0.3985	0.068*
C22	0.0481 (2)	0.3706 (2)	0.2514 (3)	0.0613 (9)
H22A	−0.0177	0.3685	0.2324	0.074*
C23	0.0938 (2)	0.4086 (2)	0.1829 (3)	0.0617 (9)
H23A	0.0589	0.4341	0.1174	0.074*
C24	0.1900 (2)	0.4110 (2)	0.2062 (3)	0.0555 (8)
C25	0.2460 (2)	0.29988 (17)	0.4875 (3)	0.0621 (9)
H25A	0.2293	0.2446	0.4886	0.075*
H25B	0.3135	0.3031	0.4933	0.075*
C26	0.2364 (2)	0.4584 (2)	0.1310 (3)	0.0735 (11)
H26A	0.3044	0.4535	0.1581	0.088*
H26B	0.2185	0.4378	0.0529	0.088*
C27	0.2098 (2)	0.5424 (2)	0.1301 (3)	0.0646 (9)
C28	0.1481 (2)	0.5766 (3)	0.0381 (3)	0.0770 (12)
H28A	0.1263	0.5476	−0.0293	0.092*
C29	0.1186 (2)	0.6510 (3)	0.0433 (3)	0.0811 (13)
H29A	0.0780	0.6736	−0.0209	0.097*
C30	0.1469 (2)	0.6929 (2)	0.1395 (3)	0.0738 (12)
H30A	0.1245	0.7441	0.1422	0.089*
C31	0.2087 (2)	0.6620 (2)	0.2352 (3)	0.0618 (9)
C32	0.24148 (19)	0.5878 (2)	0.2264 (3)	0.0616 (9)
C33	0.3978 (4)	0.5395 (3)	0.2990 (5)	0.0500 (9)	0.533 (4)
H33A	0.4286	0.4970	0.3485	0.060*	0.533 (4)
H33B	0.3931	0.5248	0.2193	0.060*	0.533 (4)
C34	0.4508 (4)	0.6121 (3)	0.3265 (5)	0.0540 (10)	0.533 (4)
H34A	0.4408	0.6322	0.3986	0.065*	0.533 (4)
H34D	0.4251	0.6506	0.2670	0.065*	0.533 (4)
C35	0.5543 (6)	0.6059 (6)	0.3371 (13)	0.055 (2)	0.533 (4)
H35A	0.5834	0.6561	0.3638	0.066*	0.533 (4)
H35B	0.5650	0.5960	0.2613	0.066*	0.533 (4)
C36	0.6019 (19)	0.5425 (19)	0.418 (2)	0.061 (3)	0.533 (4)
H36A	0.5731	0.5410	0.4830	0.073*	0.533 (4)
H36B	0.5890	0.4923	0.3782	0.073*	0.533 (4)
C33B	0.3947 (4)	0.5932 (4)	0.3494 (5)	0.0500 (9)	0.467 (4)
H33C	0.3877	0.6499	0.3401	0.060*	0.467 (4)
H33D	0.4254	0.5821	0.4293	0.060*	0.467 (4)
C34B	0.4506 (4)	0.5629 (4)	0.2750 (6)	0.0540 (10)	0.467 (4)
H34B	0.4271	0.5849	0.1984	0.065*	0.467 (4)
H34C	0.4423	0.5061	0.2690	0.065*	0.467 (4)
C35B	0.5533 (7)	0.5807 (8)	0.3147 (15)	0.055 (2)	0.467 (4)
H35C	0.5616	0.6375	0.3171	0.066*	0.467 (4)
H35D	0.5852	0.5600	0.2584	0.066*	0.467 (4)
C36B	0.600 (2)	0.547 (2)	0.431 (3)	0.061 (3)	0.467 (4)
H36C	0.5775	0.5766	0.4890	0.073*	0.467 (4)
H36D	0.5796	0.4931	0.4338	0.073*	0.467 (4)
C2B	0.5952 (3)	0.5016 (3)	0.0310 (3)	0.0789 (11)
H2BA	0.6609	0.5034	0.0528	0.095*
C3B	0.5466 (3)	0.5696 (3)	0.0090 (3)	0.0832 (12)
H3BA	0.5787	0.6174	0.0148	0.100*
C1B	0.5521 (3)	0.4318 (3)	0.0225 (3)	0.0842 (12)
H1BA	0.5868	0.3852	0.0371	0.101*

	U11	U22	U33	U12	U13	U23
O1	0.0406 (10)	0.0834 (16)	0.0504 (12)	0.0035 (10)	−0.0015 (9)	0.0210 (11)
O2	0.0453 (10)	0.0508 (11)	0.0466 (11)	0.0008 (8)	0.0132 (8)	0.0061 (9)
O3	0.0388 (9)	0.0511 (11)	0.0523 (12)	−0.0009 (8)	0.0003 (8)	−0.0101 (9)
O4	0.0406 (10)	0.0584 (12)	0.0637 (14)	0.0027 (9)	−0.0025 (9)	−0.0163 (10)
C1	0.0362 (13)	0.0587 (17)	0.0468 (16)	0.0026 (11)	0.0023 (11)	0.0181 (13)
C2	0.0413 (14)	0.0564 (18)	0.066 (2)	0.0024 (12)	−0.0041 (13)	0.0259 (15)
C3	0.0461 (16)	0.069 (2)	0.082 (3)	−0.0011 (15)	−0.0058 (16)	0.042 (2)
C4	0.0524 (18)	0.108 (3)	0.060 (2)	0.0006 (19)	0.0060 (16)	0.046 (2)
C5	0.0526 (17)	0.110 (3)	0.0413 (17)	0.0066 (18)	0.0043 (14)	0.0273 (18)
C6	0.0400 (14)	0.085 (2)	0.0373 (15)	0.0043 (14)	0.0010 (11)	0.0198 (15)
C7	0.0507 (16)	0.079 (2)	0.0385 (15)	−0.0010 (15)	0.0070 (12)	−0.0100 (15)
C8	0.0463 (14)	0.0545 (16)	0.0438 (16)	0.0046 (12)	0.0046 (12)	−0.0125 (13)
C9	0.0446 (14)	0.0636 (18)	0.0504 (17)	0.0008 (13)	0.0102 (13)	−0.0051 (14)
C10	0.0358 (14)	0.0645 (19)	0.064 (2)	0.0009 (13)	0.0032 (13)	−0.0028 (16)
C11	0.0440 (14)	0.0493 (16)	0.065 (2)	0.0010 (13)	−0.0035 (14)	0.0053 (14)
C12	0.0454 (14)	0.0413 (14)	0.0619 (19)	−0.0020 (11)	0.0009 (13)	0.0011 (13)
C13	0.0386 (13)	0.0436 (14)	0.0505 (16)	−0.0002 (11)	0.0008 (11)	−0.0098 (12)
C14	0.0467 (16)	0.0586 (19)	0.085 (3)	−0.0114 (14)	−0.0074 (16)	0.0227 (18)
C15	0.0473 (19)	0.036 (2)	0.058 (3)	−0.0012 (18)	−0.002 (2)	−0.0046 (18)
C16	0.054 (2)	0.050 (2)	0.048 (2)	−0.006 (2)	−0.001 (2)	−0.0067 (17)
C17	0.049 (2)	0.061 (3)	0.059 (3)	0.004 (2)	0.003 (2)	−0.003 (2)
C18	0.048 (2)	0.059 (4)	0.067 (4)	0.011 (2)	0.009 (3)	−0.014 (3)
C15B	0.0473 (19)	0.036 (2)	0.058 (3)	−0.0012 (18)	−0.002 (2)	−0.0046 (18)
C16B	0.054 (2)	0.050 (2)	0.048 (2)	−0.006 (2)	−0.001 (2)	−0.0067 (17)
C17B	0.049 (2)	0.061 (3)	0.059 (3)	0.004 (2)	0.003 (2)	−0.003 (2)
C18B	0.048 (2)	0.059 (4)	0.067 (4)	0.011 (2)	0.009 (3)	−0.014 (3)
C19	0.0403 (14)	0.0467 (15)	0.0576 (18)	0.0043 (11)	−0.0032 (13)	−0.0185 (13)
C20	0.0488 (15)	0.0410 (15)	0.0584 (18)	0.0012 (12)	0.0018 (13)	−0.0105 (13)
C21	0.0490 (15)	0.0551 (18)	0.0598 (19)	0.0039 (13)	0.0030 (14)	−0.0102 (15)
C22	0.0389 (14)	0.085 (2)	0.0549 (19)	0.0049 (14)	0.0009 (13)	−0.0135 (17)
C23	0.0460 (16)	0.086 (2)	0.0461 (17)	0.0164 (15)	−0.0026 (14)	−0.0141 (16)
C24	0.0485 (16)	0.070 (2)	0.0447 (17)	0.0037 (14)	0.0043 (13)	−0.0140 (14)
C25	0.0463 (15)	0.0436 (16)	0.088 (3)	0.0006 (12)	−0.0001 (16)	0.0109 (16)
C26	0.0520 (18)	0.126 (3)	0.0403 (17)	0.0173 (19)	0.0073 (14)	−0.0030 (19)
C27	0.0454 (16)	0.104 (3)	0.0426 (17)	0.0038 (16)	0.0069 (13)	0.0215 (18)
C28	0.0524 (18)	0.130 (4)	0.0441 (18)	0.002 (2)	0.0025 (15)	0.026 (2)
C29	0.0578 (19)	0.111 (3)	0.062 (2)	−0.010 (2)	−0.0089 (17)	0.047 (2)
C30	0.0516 (17)	0.083 (2)	0.078 (3)	−0.0124 (16)	−0.0023 (17)	0.048 (2)
C31	0.0421 (14)	0.071 (2)	0.064 (2)	−0.0143 (14)	−0.0024 (13)	0.0342 (17)
C32	0.0358 (14)	0.092 (3)	0.0531 (19)	−0.0039 (14)	0.0035 (13)	0.0313 (18)
C33	0.049 (2)	0.053 (2)	0.045 (2)	0.003 (2)	0.0049 (19)	−0.0055 (17)
C34	0.052 (2)	0.061 (3)	0.050 (3)	−0.003 (2)	0.013 (2)	0.0011 (19)
C35	0.0464 (17)	0.060 (7)	0.055 (6)	0.000 (3)	0.007 (2)	0.010 (5)
C36	0.0468 (18)	0.076 (4)	0.060 (5)	−0.0029 (19)	0.013 (3)	0.014 (4)
C33B	0.049 (2)	0.053 (2)	0.045 (2)	0.003 (2)	0.0049 (19)	−0.0055 (17)
C34B	0.052 (2)	0.061 (3)	0.050 (3)	−0.003 (2)	0.013 (2)	0.0011 (19)
C35B	0.0464 (17)	0.060 (7)	0.055 (6)	0.000 (3)	0.007 (2)	0.010 (5)
C36B	0.0468 (18)	0.076 (4)	0.060 (5)	−0.0029 (19)	0.013 (3)	0.014 (4)
C2B	0.064 (2)	0.123 (3)	0.0475 (19)	−0.002 (2)	0.0073 (17)	0.005 (2)
C3B	0.082 (3)	0.124 (4)	0.0413 (18)	−0.001 (2)	0.0098 (17)	−0.001 (2)
C1B	0.083 (3)	0.117 (4)	0.048 (2)	−0.001 (2)	0.0080 (19)	−0.004 (2)

O1—C32	1.379 (3)	C18B—H18C	0.9900
O1—C33B	1.492 (7)	C18B—H18D	0.9900
O1—C33	1.525 (6)	C19—C20	1.390 (5)
O2—C1	1.375 (3)	C19—C24	1.411 (4)
O2—C36	1.41 (3)	C20—C21	1.383 (4)
O2—C36B	1.42 (3)	C20—C25	1.513 (4)
O3—C13	1.393 (3)	C21—C22	1.395 (5)
O3—C15	1.440 (5)	C21—H21A	0.9500
O3—C15B	1.500 (7)	C22—C23	1.366 (5)
O4—C19	1.401 (3)	C22—H22A	0.9500
O4—C18B	1.461 (8)	C23—C24	1.391 (4)
O4—C18	1.478 (6)	C23—H23A	0.9500
C1—C6	1.398 (5)	C24—C26	1.516 (5)
C1—C2	1.402 (4)	C25—C2i	1.508 (5)
C2—C3	1.400 (5)	C25—H25A	0.9900
C2—C25i	1.508 (5)	C25—H25B	0.9900
C3—C4	1.389 (6)	C26—C27	1.505 (5)
C3—H3A	0.9500	C26—H26A	0.9900
C4—C5	1.372 (6)	C26—H26B	0.9900
C4—H4A	0.9500	C27—C32	1.397 (5)
C5—C6	1.391 (5)	C27—C28	1.399 (4)
C5—H5A	0.9500	C28—C29	1.366 (6)
C6—C7	1.502 (5)	C28—H28A	0.9500
C7—C8	1.522 (4)	C29—C30	1.356 (6)
C7—H7A	0.9900	C29—H29A	0.9500
C7—H7B	0.9900	C30—C31	1.406 (4)
C8—C13	1.392 (4)	C30—H30A	0.9500
C8—C9	1.392 (4)	C31—C32	1.386 (5)
C9—C10	1.374 (5)	C31—C14i	1.513 (5)
C9—H9A	0.9500	C33—C34	1.478 (7)
C10—C11	1.382 (5)	C33—H33A	0.9900
C10—H10A	0.9500	C33—H33B	0.9900
C11—C12	1.387 (4)	C34—C35	1.518 (10)
C11—H11A	0.9500	C34—H34A	0.9900
C12—C13	1.398 (4)	C34—H34D	0.9900
C12—C14	1.514 (5)	C35—C36	1.528 (13)
C14—C31i	1.513 (5)	C35—H35A	0.9900
C14—H14A	0.9900	C35—H35B	0.9900
C14—H14B	0.9900	C36—H36A	0.9900
C15—C16	1.521 (7)	C36—H36B	0.9900
C15—H15A	0.9900	C33B—C34B	1.467 (8)
C15—H15B	0.9900	C33B—H33C	0.9900
C16—C17	1.503 (7)	C33B—H33D	0.9900
C16—H16A	0.9900	C34B—C35B	1.519 (11)
C16—H16B	0.9900	C34B—H34B	0.9900
C17—C18	1.492 (7)	C34B—H34C	0.9900
C17—H17A	0.9900	C35B—C36B	1.531 (15)
C17—H17D	0.9900	C35B—H35C	0.9900
C18—H18A	0.9900	C35B—H35D	0.9900
C18—H18B	0.9900	C36B—H36C	0.9900
C15B—C16B	1.529 (9)	C36B—H36D	0.9900
C15B—H15C	0.9900	C2B—C1B	1.361 (6)
C15B—H15D	0.9900	C2B—C3B	1.372 (6)
C16B—C17B	1.466 (10)	C2B—H2BA	0.9500
C16B—H16C	0.9900	C3B—C1Bii	1.426 (6)
C16B—H16D	0.9900	C3B—H3BA	0.9500
C17B—C18B	1.492 (9)	C1B—C3Bii	1.426 (6)
C17B—H17B	0.9900	C1B—H1BA	0.9500
C17B—H17C	0.9900
C32—O1—C33B	114.1 (3)	C20—C19—C24	121.4 (3)
C32—O1—C33	113.5 (3)	O4—C19—C24	118.6 (3)
C1—O2—C36	117.2 (12)	C21—C20—C19	118.5 (3)
C1—O2—C36B	121.7 (12)	C21—C20—C25	118.9 (3)
C13—O3—C15	114.1 (3)	C19—C20—C25	122.6 (3)
C13—O3—C15B	111.6 (3)	C20—C21—C22	121.0 (3)
C19—O4—C18B	111.0 (4)	C20—C21—H21A	119.5
C19—O4—C18	114.5 (3)	C22—C21—H21A	119.5
O2—C1—C6	119.6 (3)	C23—C22—C21	119.4 (3)
O2—C1—C2	117.9 (3)	C23—C22—H22A	120.3
C6—C1—C2	122.4 (3)	C21—C22—H22A	120.3
C3—C2—C1	117.1 (4)	C22—C23—C24	121.9 (3)
C3—C2—C25i	124.2 (3)	C22—C23—H23A	119.0
C1—C2—C25i	118.5 (3)	C24—C23—H23A	119.0
C4—C3—C2	121.3 (4)	C23—C24—C19	117.5 (3)
C4—C3—H3A	119.3	C23—C24—C26	119.3 (3)
C2—C3—H3A	119.3	C19—C24—C26	123.2 (3)
C5—C4—C3	119.7 (3)	C2i—C25—C20	112.1 (2)
C5—C4—H4A	120.1	C2i—C25—H25A	109.2
C3—C4—H4A	120.1	C20—C25—H25A	109.2
C4—C5—C6	121.6 (4)	C2i—C25—H25B	109.2
C4—C5—H5A	119.2	C20—C25—H25B	109.2
C6—C5—H5A	119.2	H25A—C25—H25B	107.9
C5—C6—C1	117.7 (3)	C27—C26—C24	111.6 (3)
C5—C6—C7	121.9 (3)	C27—C26—H26A	109.3
C1—C6—C7	120.1 (3)	C24—C26—H26A	109.3
C6—C7—C8	110.4 (2)	C27—C26—H26B	109.3
C6—C7—H7A	109.6	C24—C26—H26B	109.3
C8—C7—H7A	109.6	H26A—C26—H26B	108.0
C6—C7—H7B	109.6	C32—C27—C28	117.3 (4)
C8—C7—H7B	109.6	C32—C27—C26	120.2 (3)
H7A—C7—H7B	108.1	C28—C27—C26	122.4 (4)
C13—C8—C9	118.8 (3)	C29—C28—C27	121.2 (4)
C13—C8—C7	122.9 (3)	C29—C28—H28A	119.4
C9—C8—C7	118.2 (3)	C27—C28—H28A	119.4
C10—C9—C8	121.1 (3)	C30—C29—C28	120.5 (3)
C10—C9—H9A	119.5	C30—C29—H29A	119.8
C8—C9—H9A	119.5	C28—C29—H29A	119.8
C9—C10—C11	119.3 (3)	C29—C30—C31	121.3 (4)
C9—C10—H10A	120.4	C29—C30—H30A	119.3
C11—C10—H10A	120.4	C31—C30—H30A	119.3
C10—C11—C12	121.8 (3)	C32—C31—C30	117.3 (4)
C10—C11—H11A	119.1	C32—C31—C14i	120.5 (3)
C12—C11—H11A	119.1	C30—C31—C14i	122.0 (4)
C11—C12—C13	118.0 (3)	O1—C32—C31	119.3 (3)
C11—C12—C14	119.2 (3)	O1—C32—C27	118.3 (3)
C13—C12—C14	122.6 (3)	C31—C32—C27	122.2 (3)
C8—C13—O3	119.1 (2)	C34—C33—O1	106.3 (4)
C8—C13—C12	121.1 (2)	C34—C33—H33A	110.5
O3—C13—C12	119.8 (3)	O1—C33—H33A	110.5
C31i—C14—C12	110.5 (2)	C34—C33—H33B	110.5
C31i—C14—H14A	109.6	O1—C33—H33B	110.5
C12—C14—H14A	109.6	H33A—C33—H33B	108.7
C31i—C14—H14B	109.6	C33—C34—C35	115.7 (6)
C12—C14—H14B	109.6	C33—C34—H34A	108.3
H14A—C14—H14B	108.1	C35—C34—H34A	108.3
O3—C15—C16	109.0 (4)	C33—C34—H34D	108.3
O3—C15—H15A	109.9	C35—C34—H34D	108.3
C16—C15—H15A	109.9	H34A—C34—H34D	107.4
O3—C15—H15B	109.9	C34—C35—C36	114.2 (13)
C16—C15—H15B	109.9	C34—C35—H35A	108.7
H15A—C15—H15B	108.3	C36—C35—H35A	108.7
C17—C16—C15	116.0 (5)	C34—C35—H35B	108.7
C17—C16—H16A	108.3	C36—C35—H35B	108.7
C15—C16—H16A	108.3	H35A—C35—H35B	107.6
C17—C16—H16B	108.3	O2—C36—C35	117 (2)
C15—C16—H16B	108.3	O2—C36—H36A	108.1
H16A—C16—H16B	107.4	C35—C36—H36A	108.1
C18—C17—C16	116.4 (5)	O2—C36—H36B	108.1
C18—C17—H17A	108.2	C35—C36—H36B	108.1
C16—C17—H17A	108.2	H36A—C36—H36B	107.3
C18—C17—H17D	108.2	C34B—C33B—O1	108.2 (5)
C16—C17—H17D	108.2	C34B—C33B—H33C	110.1
H17A—C17—H17D	107.3	O1—C33B—H33C	110.1
O4—C18—C17	111.8 (5)	C34B—C33B—H33D	110.1
O4—C18—H18A	109.3	O1—C33B—H33D	110.1
C17—C18—H18A	109.3	H33C—C33B—H33D	108.4
O4—C18—H18B	109.3	C33B—C34B—C35B	114.0 (7)
C17—C18—H18B	109.3	C33B—C34B—H34B	108.7
H18A—C18—H18B	107.9	C35B—C34B—H34B	108.7
O3—C15B—C16B	108.0 (5)	C33B—C34B—H34C	108.7
O3—C15B—H15C	110.1	C35B—C34B—H34C	108.7
C16B—C15B—H15C	110.1	H34B—C34B—H34C	107.6
O3—C15B—H15D	110.1	C34B—C35B—C36B	114.5 (15)
C16B—C15B—H15D	110.1	C34B—C35B—H35C	108.6
H15C—C15B—H15D	108.4	C36B—C35B—H35C	108.6
C17B—C16B—C15B	117.4 (7)	C34B—C35B—H35D	108.6
C17B—C16B—H16C	108.0	C36B—C35B—H35D	108.6
C15B—C16B—H16C	108.0	H35C—C35B—H35D	107.6
C17B—C16B—H16D	108.0	O2—C36B—C35B	115 (2)
C15B—C16B—H16D	108.0	O2—C36B—H36C	108.4
H16C—C16B—H16D	107.2	C35B—C36B—H36C	108.4
C16B—C17B—C18B	117.3 (7)	O2—C36B—H36D	108.4
C16B—C17B—H17B	108.0	C35B—C36B—H36D	108.4
C18B—C17B—H17B	108.0	H36C—C36B—H36D	107.5
C16B—C17B—H17C	108.0	C1B—C2B—C3B	122.0 (4)
C18B—C17B—H17C	108.0	C1B—C2B—H2BA	119.0
H17B—C17B—H17C	107.2	C3B—C2B—H2BA	119.0
O4—C18B—C17B	109.8 (6)	C2B—C3B—C1Bii	119.9 (5)
O4—C18B—H18C	109.7	C2B—C3B—H3BA	120.0
C17B—C18B—H18C	109.7	C1Bii—C3B—H3BA	120.0
O4—C18B—H18D	109.7	C2B—C1B—C3Bii	118.1 (5)
C17B—C18B—H18D	109.7	C2B—C1B—H1BA	121.0
H18C—C18B—H18D	108.2	C3Bii—C1B—H1BA	121.0
C20—C19—O4	119.9 (3)
C36—O2—C1—C6	−81.0 (18)	C18—O4—C19—C20	107.8 (4)
C36B—O2—C1—C6	−88 (2)	C18B—O4—C19—C24	−111.5 (5)
C36—O2—C1—C2	102.7 (17)	C18—O4—C19—C24	−73.8 (4)
C36B—O2—C1—C2	95 (2)	O4—C19—C20—C21	−177.2 (2)
O2—C1—C2—C3	178.3 (2)	C24—C19—C20—C21	4.5 (4)
C6—C1—C2—C3	2.0 (4)	O4—C19—C20—C25	5.5 (4)
O2—C1—C2—C25i	1.7 (4)	C24—C19—C20—C25	−172.8 (3)
C6—C1—C2—C25i	−174.6 (2)	C19—C20—C21—C22	−1.1 (5)
C1—C2—C3—C4	0.7 (4)	C25—C20—C21—C22	176.3 (3)
C25i—C2—C3—C4	177.1 (3)	C20—C21—C22—C23	−2.0 (5)
C2—C3—C4—C5	−3.0 (5)	C21—C22—C23—C24	1.9 (5)
C3—C4—C5—C6	2.6 (5)	C22—C23—C24—C19	1.4 (5)
C4—C5—C6—C1	0.1 (4)	C22—C23—C24—C26	−176.2 (3)
C4—C5—C6—C7	−173.9 (3)	C20—C19—C24—C23	−4.6 (4)
O2—C1—C6—C5	−178.6 (2)	O4—C19—C24—C23	177.0 (3)
C2—C1—C6—C5	−2.5 (4)	C20—C19—C24—C26	172.8 (3)
O2—C1—C6—C7	−4.6 (4)	O4—C19—C24—C26	−5.5 (4)
C2—C1—C6—C7	171.6 (3)	C21—C20—C25—C2i	−60.7 (4)
C5—C6—C7—C8	109.6 (3)	C19—C20—C25—C2i	116.6 (3)
C1—C6—C7—C8	−64.2 (3)	C23—C24—C26—C27	59.7 (4)
C6—C7—C8—C13	122.4 (3)	C19—C24—C26—C27	−117.7 (3)
C6—C7—C8—C9	−53.7 (4)	C24—C26—C27—C32	69.7 (4)
C13—C8—C9—C10	−0.9 (5)	C24—C26—C27—C28	−105.5 (4)
C7—C8—C9—C10	175.3 (3)	C32—C27—C28—C29	−1.4 (5)
C8—C9—C10—C11	−0.7 (5)	C26—C27—C28—C29	174.0 (3)
C9—C10—C11—C12	0.3 (5)	C27—C28—C29—C30	−1.7 (6)
C10—C11—C12—C13	1.7 (5)	C28—C29—C30—C31	1.5 (6)
C10—C11—C12—C14	−173.8 (3)	C29—C30—C31—C32	1.8 (5)
C9—C8—C13—O3	179.4 (3)	C29—C30—C31—C14i	−172.4 (3)
C7—C8—C13—O3	3.3 (4)	C33B—O1—C32—C31	−67.4 (4)
C9—C8—C13—C12	3.0 (4)	C33—O1—C32—C31	−115.3 (4)
C7—C8—C13—C12	−173.1 (3)	C33B—O1—C32—C27	117.5 (4)
C15—O3—C13—C8	105.6 (4)	C33—O1—C32—C27	69.6 (4)
C15B—O3—C13—C8	67.4 (4)	C30—C31—C32—O1	−179.8 (3)
C15—O3—C13—C12	−78.0 (4)	C14i—C31—C32—O1	−5.6 (4)
C15B—O3—C13—C12	−116.2 (4)	C30—C31—C32—C27	−5.0 (5)
C11—C12—C13—C8	−3.4 (4)	C14i—C31—C32—C27	169.3 (3)
C14—C12—C13—C8	171.9 (3)	C28—C27—C32—O1	179.7 (3)
C11—C12—C13—O3	−179.7 (3)	C26—C27—C32—O1	4.2 (5)
C14—C12—C13—O3	−4.4 (4)	C28—C27—C32—C31	4.8 (5)
C11—C12—C14—C31i	56.5 (4)	C26—C27—C32—C31	−170.7 (3)
C13—C12—C14—C31i	−118.8 (3)	C32—O1—C33—C34	85.6 (5)
C13—O3—C15—C16	175.6 (4)	C33B—O1—C33—C34	−15.3 (5)
C15B—O3—C15—C16	−90.7 (7)	O1—C33—C34—C35	167.7 (8)
O3—C15—C16—C17	72.4 (6)	C33—C34—C35—C36	−52.3 (18)
C15—C16—C17—C18	179.0 (5)	C1—O2—C36—C35	−32 (3)
C19—O4—C18—C17	175.6 (4)	C36B—O2—C36—C35	95 (19)
C18B—O4—C18—C17	−92.3 (8)	C34—C35—C36—O2	−160 (2)
C16—C17—C18—O4	80.8 (6)	C32—O1—C33B—C34B	−81.5 (6)
C13—O3—C15B—C16B	−166.0 (5)	C33—O1—C33B—C34B	17.9 (5)
C15—O3—C15B—C16B	92.3 (8)	O1—C33B—C34B—C35B	−165.5 (8)
O3—C15B—C16B—C17B	−66.8 (8)	C33B—C34B—C35B—C36B	60 (2)
C15B—C16B—C17B—C18B	−175.3 (7)	C1—O2—C36B—C35B	4 (4)
C19—O4—C18B—C17B	−168.4 (6)	C36—O2—C36B—C35B	−53 (16)
C18—O4—C18B—C17B	88.7 (9)	C34B—C35B—C36B—O2	168 (2)
C16B—C17B—C18B—O4	−78.3 (9)	C1B—C2B—C3B—C1Bii	0.8 (7)
C18B—O4—C19—C20	70.1 (5)	C3B—C2B—C1B—C3Bii	−0.7 (7)