6,6-Di­methyl-2-(1-methyl­ethenyl)-3,4,5-tris­(1-methylethylidene)-1-(2-methyl­propen-1-yl)cyclo­hexane

The title compound, C₂₄H₃₆, crystallizes with two independent but very similar mol­ecules in the asymmetric unit. The ring torsion angles about the double bonds are ca 13°; the ring sp² bond angles at the three radialene-type junctions are ca 110°.

Key indicators

• Single-crystal X-ray study
• T = 143 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.064
• wR factor = 0.164
• Data-to-parameter ratio = 16.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Permethylbutatriene, (1), generated in situ, is known to cyclooligomerize to dodecamethyl[6]radialene, (2), in the presence of nickel catalyst systems (Iyoda et al., 1984, 1988; Stehling & Wilke, 1985). Although the yield of this process is good (>70%), it is accompanied by the formation of several by-products, most of which have not been fully characterized. Repeating this trimerization (Höpfner, 1996), we have isolated one of the minor (5%) products and have identified it as the title compound, (3), by X-ray methods.

Compound (3) crystallizes with two independent but closely similar molecules (Fig. 1); a least-squares fit of all non-H atoms (Fig. 2) gave an r.m.s. deviation of only 0.04 Å. For this reason, only the dimensions of molecule 1 (unprimed atoms) will be discussed explicitly.

The ring shows a torsion angle of 13.8 (3)° about the C2═C3 double bond. The sp² angles at the radialene-type ring junctions are markedly narrowed, with ring angles of 109.2 (2), 109.9 (2) and 112.9 (2)° at C4, C5 and C6, respectively. Other molecular dimensions may be regarded as normal (e.g. the double-bond lengths in Table 1), but considering the caveat given in the Experimental section.

S2. Experimental

Compound (3) was obtained as described by Höpfner (1996) and recrystallized from methanol.

S3. Refinement

Methyl H atoms were identified in difference syntheses, idealized and then refined using rigid methyl groups (C—H = 0.98 Å and H—C—H = 109.5°) Other H atoms were included using a riding model with fixed C—H bond lengths of 0.95 Å; U_iso(H) values were fixed at 1.2 times the U_eq values of the parent atom. The bond lengths of the methylethenyl substituent, and the fact that the largest difference peaks were at bonding distance to C17 and C17' (the corresponding methyl H atoms were the least well resolved) may indicate some disorder between the methylene and methyl sites C17 and C18 (and C17' and C18').

Computing details

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The two independent molecules of compound (3) in the crystal. Ellipsoids represent 30% probability levels and H-atom radii are arbitrary.
	Fig. 2. Least-squares fit of both independent molecules of compound (3).

6,6-Dimethyl-2-(methylethenyl)-3,4,5-tris(methylidene)-1-(2-methylpropen- 1-yl)-cyclohexane

Crystal data

C24H36	F(000) = 1440
Mr = 324.53	Dx = 1.035 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.382 (2) Å	Cell parameters from 54 reflections
b = 17.062 (2) Å	θ = 10–11°
c = 17.053 (2) Å	µ = 0.06 mm^−1
β = 95.436 (12)°	T = 143 K
V = 4165.6 (9) Å^3	Prism, colourless
Z = 8	0.6 × 0.5 × 0.4 mm

Data collection

Stoe Stadi-4 diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.1°
Graphite monochromator	h = −17→17
ω–θ scans	k = 0→20
7622 measured reflections	l = −20→1
7330 independent reflections	3 standard reflections every 60 min
4782 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 2.454P] where P = (Fo^2 + 2Fc^2)/3
7330 reflections	(Δ/σ)max = 0.036
455 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.20134 (16)	0.64983 (13)	0.24293 (13)	0.0223 (5)
C2	0.25543 (16)	0.60076 (14)	0.30790 (13)	0.0219 (5)
C3	0.23382 (16)	0.52548 (14)	0.32256 (13)	0.0220 (5)
C4	0.16990 (16)	0.48270 (13)	0.26335 (13)	0.0226 (5)
C5	0.18062 (16)	0.51489 (13)	0.18318 (13)	0.0220 (5)
C6	0.14962 (16)	0.59804 (14)	0.17881 (14)	0.0229 (5)
C7	0.13380 (18)	0.70126 (15)	0.28646 (15)	0.0309 (6)
H7A	0.1671	0.7228	0.3345	0.037*
H7B	0.0813	0.6692	0.3004	0.037*
H7C	0.1103	0.7443	0.2520	0.037*
C8	0.27032 (18)	0.70094 (15)	0.20212 (15)	0.0318 (6)
H8A	0.3010	0.7378	0.2403	0.038*
H8B	0.2365	0.7302	0.1589	0.038*
H8C	0.3175	0.6674	0.1811	0.038*
C9	0.32968 (18)	0.64425 (15)	0.35538 (14)	0.0282 (6)
H9	0.3104	0.6896	0.3818	0.034*
C10	0.41966 (19)	0.62747 (16)	0.36537 (16)	0.0352 (6)
C11	0.27873 (17)	0.48101 (15)	0.39150 (14)	0.0286 (6)
C12	0.10868 (17)	0.42621 (14)	0.27783 (15)	0.0275 (6)
C13	0.22378 (18)	0.47683 (15)	0.12826 (14)	0.0293 (6)
C14	0.08328 (17)	0.62306 (15)	0.12419 (14)	0.0274 (6)
C15	0.4866 (2)	0.6785 (2)	0.41532 (19)	0.0556 (9)
H15A	0.4529	0.7234	0.4347	0.067*
H15B	0.5356	0.6973	0.3837	0.067*
H15C	0.5150	0.6482	0.4601	0.067*
C16	0.4632 (2)	0.55855 (17)	0.3292 (2)	0.0494 (8)
H16A	0.4801	0.5192	0.3699	0.059*
H16B	0.5195	0.5754	0.3056	0.059*
H16C	0.4187	0.5358	0.2884	0.059*
C17	0.2757 (2)	0.51297 (18)	0.47073 (15)	0.0481 (8)
H17A	0.3119	0.4792	0.5088	0.058*
H17B	0.2107	0.5153	0.4835	0.058*
H17C	0.3024	0.5658	0.4730	0.058*
C18	0.31915 (19)	0.40983 (16)	0.38042 (16)	0.0369 (7)
H18A	0.3456	0.3806	0.4245	0.044*
H18B	0.3208	0.3896	0.3287	0.044*
C19	0.09067 (19)	0.39797 (16)	0.35839 (15)	0.0346 (6)
H19A	0.1186	0.3460	0.3676	0.042*
H19B	0.0232	0.3948	0.3620	0.042*
H19C	0.1185	0.4347	0.3981	0.042*
C20	0.04864 (19)	0.38616 (16)	0.21281 (17)	0.0370 (7)
H20A	0.0623	0.4077	0.1619	0.044*
H20B	−0.0173	0.3948	0.2201	0.044*
H20C	0.0618	0.3298	0.2141	0.044*
C21	0.2578 (2)	0.39357 (15)	0.13865 (16)	0.0394 (7)
H21A	0.2530	0.3769	0.1931	0.047*
H21B	0.3231	0.3905	0.1269	0.047*
H21C	0.2194	0.3592	0.1027	0.047*
C22	0.2438 (2)	0.51301 (17)	0.05137 (15)	0.0375 (7)
H22A	0.2052	0.4876	0.0082	0.045*
H22B	0.3099	0.5059	0.0438	0.045*
H22C	0.2292	0.5691	0.0520	0.045*
C23	0.03249 (19)	0.56951 (16)	0.06454 (15)	0.0379 (7)
H23A	0.0511	0.5815	0.0121	0.045*
H23B	−0.0350	0.5772	0.0648	0.045*
H23C	0.0483	0.5149	0.0779	0.045*
C24	0.0478 (2)	0.70605 (16)	0.11344 (16)	0.0386 (7)
H24A	−0.0096	0.7121	0.1396	0.046*
H24B	0.0347	0.7173	0.0571	0.046*
H24C	0.0952	0.7426	0.1367	0.046*
C1'	0.30796 (16)	0.88366 (14)	0.77252 (14)	0.0239 (5)
C2'	0.25355 (16)	0.83892 (14)	0.70453 (13)	0.0226 (5)
C3'	0.27110 (16)	0.76316 (14)	0.68756 (13)	0.0226 (5)
C4'	0.33046 (16)	0.71599 (13)	0.74610 (13)	0.0218 (5)
C5'	0.31981 (16)	0.74614 (14)	0.82705 (14)	0.0235 (5)
C6'	0.35559 (16)	0.82765 (14)	0.83554 (13)	0.0227 (5)
C7'	0.37930 (18)	0.93452 (15)	0.73317 (15)	0.0325 (6)
H7'1	0.3484	0.9594	0.6858	0.039*
H7'2	0.4306	0.9014	0.7186	0.039*
H7'3	0.4041	0.9751	0.7701	0.039*
C8'	0.23969 (18)	0.93598 (15)	0.81307 (15)	0.0331 (6)
H8'1	0.2106	0.9737	0.7749	0.040*
H8'2	0.2738	0.9642	0.8568	0.040*
H8'3	0.1912	0.9033	0.8333	0.040*
C9'	0.18299 (18)	0.88555 (15)	0.65556 (14)	0.0289 (6)
H9'	0.2052	0.9305	0.6303	0.035*
C10'	0.09208 (19)	0.87104 (16)	0.64331 (16)	0.0356 (7)
C11'	0.22586 (17)	0.72332 (15)	0.61578 (14)	0.0263 (6)
C12'	0.38889 (17)	0.65805 (14)	0.73057 (14)	0.0258 (6)
C13'	0.27311 (18)	0.70862 (15)	0.87967 (14)	0.0286 (6)
C14'	0.42218 (17)	0.84749 (15)	0.89223 (14)	0.0290 (6)
C15'	0.0288 (2)	0.9219 (2)	0.58928 (19)	0.0567 (9)
H15D	0.0650	0.9651	0.5696	0.068*
H15E	−0.0212	0.9431	0.6183	0.068*
H15F	0.0015	0.8905	0.5448	0.068*
C16'	0.0444 (2)	0.80442 (18)	0.6800 (2)	0.0485 (8)
H16D	0.0880	0.7793	0.7199	0.058*
H16E	0.0235	0.7660	0.6393	0.058*
H16F	−0.0098	0.8242	0.7048	0.058*
C17'	0.2360 (2)	0.75746 (17)	0.53835 (15)	0.0394 (7)
H17D	0.2076	0.7225	0.4972	0.047*
H17E	0.3025	0.7641	0.5317	0.047*
H17F	0.2049	0.8086	0.5343	0.047*
C18'	0.17941 (18)	0.65451 (16)	0.62295 (16)	0.0339 (6)
H18C	0.1530	0.6279	0.5772	0.041*
H18D	0.1734	0.6331	0.6737	0.041*
C19'	0.40771 (18)	0.63178 (15)	0.64908 (15)	0.0309 (6)
H19D	0.3789	0.5804	0.6380	0.037*
H19E	0.4753	0.6279	0.6461	0.037*
H19F	0.3812	0.6699	0.6102	0.037*
C20'	0.4447 (2)	0.61292 (16)	0.79430 (17)	0.0395 (7)
H20D	0.4299	0.6319	0.8459	0.047*
H20E	0.5115	0.6203	0.7893	0.047*
H20F	0.4292	0.5571	0.7893	0.047*
C21'	0.2342 (2)	0.62724 (16)	0.86563 (16)	0.0405 (7)
H21D	0.2401	0.6119	0.8109	0.049*
H21E	0.1682	0.6266	0.8755	0.049*
H21F	0.2691	0.5903	0.9013	0.049*
C22'	0.2546 (2)	0.74269 (18)	0.95819 (15)	0.0400 (7)
H22D	0.2931	0.7156	1.0003	0.048*
H22E	0.1884	0.7360	0.9661	0.048*
H22F	0.2701	0.7986	0.9593	0.048*
C23'	0.46983 (19)	0.78845 (17)	0.94823 (15)	0.0376 (7)
H23D	0.4527	0.7354	0.9302	0.045*
H23E	0.4501	0.7966	1.0011	0.045*
H23F	0.5377	0.7949	0.9498	0.045*
C24'	0.4618 (2)	0.92882 (16)	0.90898 (17)	0.0404 (7)
H24D	0.5205	0.9345	0.8846	0.048*
H24E	0.4735	0.9364	0.9660	0.048*
H24F	0.4169	0.9682	0.8871	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0244 (13)	0.0180 (12)	0.0243 (12)	−0.0009 (10)	0.0017 (10)	−0.0014 (10)
C2	0.0243 (13)	0.0213 (13)	0.0203 (12)	0.0028 (10)	0.0029 (10)	−0.0039 (10)
C3	0.0233 (12)	0.0214 (13)	0.0217 (12)	0.0034 (10)	0.0046 (10)	0.0007 (10)
C4	0.0260 (13)	0.0177 (12)	0.0244 (12)	0.0035 (10)	0.0032 (10)	0.0002 (10)
C5	0.0231 (12)	0.0200 (12)	0.0221 (12)	−0.0019 (10)	−0.0022 (10)	0.0015 (10)
C6	0.0252 (13)	0.0203 (13)	0.0234 (12)	−0.0033 (10)	0.0033 (10)	0.0021 (10)
C7	0.0322 (14)	0.0257 (14)	0.0346 (15)	0.0058 (11)	0.0023 (12)	−0.0043 (11)
C8	0.0320 (14)	0.0270 (14)	0.0363 (15)	−0.0064 (12)	0.0015 (12)	0.0038 (12)
C9	0.0365 (15)	0.0230 (13)	0.0244 (13)	−0.0002 (11)	−0.0007 (11)	−0.0054 (11)
C10	0.0341 (15)	0.0335 (16)	0.0361 (15)	−0.0046 (12)	−0.0064 (12)	−0.0004 (12)
C11	0.0321 (14)	0.0283 (14)	0.0252 (13)	−0.0063 (12)	0.0010 (11)	0.0050 (11)
C12	0.0282 (14)	0.0211 (13)	0.0330 (14)	0.0011 (11)	0.0018 (11)	0.0022 (11)
C13	0.0351 (15)	0.0268 (14)	0.0257 (13)	−0.0031 (11)	0.0020 (11)	−0.0031 (11)
C14	0.0296 (14)	0.0251 (14)	0.0271 (13)	−0.0017 (11)	0.0016 (11)	0.0014 (11)
C15	0.0446 (19)	0.058 (2)	0.060 (2)	−0.0089 (16)	−0.0211 (16)	−0.0037 (17)
C16	0.0311 (16)	0.0401 (18)	0.078 (2)	0.0010 (14)	0.0079 (15)	−0.0018 (16)
C17	0.070 (2)	0.0478 (19)	0.0254 (15)	−0.0008 (17)	0.0008 (14)	0.0055 (14)
C18	0.0439 (17)	0.0316 (15)	0.0339 (15)	0.0058 (13)	−0.0035 (13)	0.0079 (12)
C19	0.0333 (15)	0.0320 (15)	0.0394 (16)	−0.0003 (12)	0.0082 (12)	0.0073 (12)
C20	0.0363 (15)	0.0270 (15)	0.0468 (17)	−0.0058 (12)	−0.0009 (13)	0.0016 (13)
C21	0.0557 (19)	0.0297 (15)	0.0333 (15)	0.0073 (14)	0.0066 (13)	−0.0042 (12)
C22	0.0459 (17)	0.0399 (17)	0.0276 (14)	0.0002 (14)	0.0082 (12)	−0.0015 (12)
C23	0.0422 (16)	0.0389 (17)	0.0303 (15)	0.0013 (13)	−0.0085 (12)	−0.0012 (13)
C24	0.0401 (16)	0.0334 (16)	0.0402 (16)	0.0031 (13)	−0.0071 (13)	0.0080 (13)
C1'	0.0244 (13)	0.0193 (12)	0.0283 (13)	−0.0011 (10)	0.0042 (10)	−0.0019 (10)
C2'	0.0245 (13)	0.0205 (13)	0.0231 (12)	−0.0008 (10)	0.0042 (10)	0.0018 (10)
C3'	0.0229 (12)	0.0249 (13)	0.0205 (12)	−0.0030 (10)	0.0048 (10)	0.0019 (10)
C4'	0.0241 (12)	0.0171 (12)	0.0239 (12)	−0.0031 (10)	0.0004 (10)	0.0009 (10)
C5'	0.0247 (13)	0.0213 (13)	0.0238 (13)	0.0018 (10)	−0.0012 (10)	0.0026 (10)
C6'	0.0250 (13)	0.0206 (13)	0.0234 (12)	0.0011 (10)	0.0070 (10)	−0.0024 (10)
C7'	0.0343 (15)	0.0263 (14)	0.0367 (15)	−0.0066 (12)	0.0019 (12)	0.0036 (12)
C8'	0.0359 (15)	0.0288 (15)	0.0345 (15)	0.0072 (12)	0.0025 (12)	−0.0076 (12)
C9'	0.0380 (15)	0.0213 (13)	0.0266 (13)	0.0020 (11)	−0.0009 (11)	0.0002 (11)
C10'	0.0332 (15)	0.0324 (15)	0.0397 (16)	0.0075 (12)	−0.0051 (12)	−0.0091 (13)
C11'	0.0270 (13)	0.0279 (14)	0.0234 (13)	0.0051 (11)	−0.0010 (10)	−0.0025 (11)
C12'	0.0268 (13)	0.0187 (12)	0.0310 (14)	−0.0035 (11)	−0.0025 (11)	−0.0022 (11)
C13'	0.0329 (14)	0.0266 (14)	0.0252 (13)	−0.0036 (11)	−0.0023 (11)	0.0045 (11)
C14'	0.0299 (14)	0.0317 (15)	0.0255 (13)	−0.0015 (12)	0.0031 (11)	−0.0056 (11)
C15'	0.053 (2)	0.051 (2)	0.060 (2)	0.0199 (16)	−0.0248 (17)	−0.0081 (17)
C16'	0.0267 (15)	0.0463 (19)	0.072 (2)	0.0005 (14)	0.0036 (14)	−0.0132 (17)
C17'	0.0482 (18)	0.0431 (17)	0.0264 (14)	0.0057 (14)	0.0013 (13)	−0.0007 (13)
C18'	0.0344 (15)	0.0333 (15)	0.0332 (15)	−0.0035 (12)	−0.0014 (12)	−0.0113 (12)
C19'	0.0304 (14)	0.0235 (14)	0.0390 (15)	0.0033 (11)	0.0050 (12)	−0.0055 (12)
C20'	0.0401 (16)	0.0318 (16)	0.0444 (17)	0.0104 (13)	−0.0069 (13)	−0.0037 (13)
C21'	0.0534 (19)	0.0351 (16)	0.0328 (15)	−0.0122 (14)	0.0040 (13)	0.0079 (13)
C22'	0.0439 (17)	0.0469 (18)	0.0305 (15)	−0.0029 (14)	0.0105 (13)	0.0044 (13)
C23'	0.0379 (16)	0.0428 (17)	0.0299 (14)	−0.0021 (13)	−0.0085 (12)	−0.0045 (13)
C24'	0.0435 (17)	0.0374 (16)	0.0393 (16)	−0.0076 (14)	−0.0013 (13)	−0.0136 (13)

Geometric parameters (Å, º)

C1—C8	1.536 (3)	C1'—C2'	1.539 (3)
C1—C2	1.540 (3)	C1'—C8'	1.539 (3)
C1—C6	1.541 (3)	C1'—C7'	1.545 (3)
C1—C7	1.550 (3)	C1'—C6'	1.548 (3)
C2—C3	1.350 (3)	C2'—C3'	1.354 (3)
C2—C9	1.477 (3)	C2'—C9'	1.483 (3)
C3—C4	1.490 (3)	C3'—C4'	1.487 (3)
C3—C11	1.494 (3)	C3'—C11'	1.494 (3)
C4—C12	1.344 (3)	C4'—C12'	1.340 (3)
C4—C5	1.495 (3)	C4'—C5'	1.495 (3)
C5—C13	1.340 (3)	C5'—C13'	1.334 (3)
C5—C6	1.487 (3)	C5'—C6'	1.485 (3)
C6—C14	1.339 (3)	C6'—C14'	1.338 (3)
C7—H7A	0.9800	C7'—H7'1	0.9800
C7—H7B	0.9800	C7'—H7'2	0.9800
C7—H7C	0.9800	C7'—H7'3	0.9800
C8—H8A	0.9800	C8'—H8'1	0.9800
C8—H8B	0.9800	C8'—H8'2	0.9800
C8—H8C	0.9800	C8'—H8'3	0.9800
C9—C10	1.321 (4)	C9'—C10'	1.328 (4)
C9—H9	0.9500	C9'—H9'	0.9500
C10—C16	1.493 (4)	C10'—C16'	1.495 (4)
C10—C15	1.502 (4)	C10'—C15'	1.507 (4)
C11—C18	1.367 (4)	C11'—C18'	1.362 (4)
C11—C17	1.461 (4)	C11'—C17'	1.463 (3)
C12—C19	1.501 (3)	C12'—C20'	1.501 (3)
C12—C20	1.504 (3)	C12'—C19'	1.509 (3)
C13—C22	1.501 (3)	C13'—C22'	1.507 (4)
C13—C21	1.507 (4)	C13'—C21'	1.507 (4)
C14—C23	1.504 (3)	C14'—C23'	1.507 (4)
C14—C24	1.511 (3)	C14'—C24'	1.517 (4)
C15—H15A	0.9800	C15'—H15D	0.9800
C15—H15B	0.9800	C15'—H15E	0.9800
C15—H15C	0.9800	C15'—H15F	0.9800
C16—H16A	0.9800	C16'—H16D	0.9800
C16—H16B	0.9800	C16'—H16E	0.9800
C16—H16C	0.9800	C16'—H16F	0.9800
C17—H17A	0.9800	C17'—H17D	0.9800
C17—H17B	0.9800	C17'—H17E	0.9800
C17—H17C	0.9800	C17'—H17F	0.9800
C18—H18A	0.9500	C18'—H18C	0.9500
C18—H18B	0.9500	C18'—H18D	0.9500
C19—H19A	0.9800	C19'—H19D	0.9800
C19—H19B	0.9800	C19'—H19E	0.9800
C19—H19C	0.9800	C19'—H19F	0.9800
C20—H20A	0.9800	C20'—H20D	0.9800
C20—H20B	0.9800	C20'—H20E	0.9800
C20—H20C	0.9800	C20'—H20F	0.9800
C21—H21A	0.9800	C21'—H21D	0.9800
C21—H21B	0.9800	C21'—H21E	0.9800
C21—H21C	0.9800	C21'—H21F	0.9800
C22—H22A	0.9800	C22'—H22D	0.9800
C22—H22B	0.9800	C22'—H22E	0.9800
C22—H22C	0.9800	C22'—H22F	0.9800
C23—H23A	0.9800	C23'—H23D	0.9800
C23—H23B	0.9800	C23'—H23E	0.9800
C23—H23C	0.9800	C23'—H23F	0.9800
C24—H24A	0.9800	C24'—H24D	0.9800
C24—H24B	0.9800	C24'—H24E	0.9800
C24—H24C	0.9800	C24'—H24F	0.9800
C8—C1—C2	109.31 (19)	C2'—C1'—C8'	109.0 (2)
C8—C1—C6	107.04 (19)	C2'—C1'—C7'	105.22 (19)
C2—C1—C6	112.08 (19)	C8'—C1'—C7'	110.3 (2)
C8—C1—C7	110.9 (2)	C2'—C1'—C6'	112.14 (19)
C2—C1—C7	105.07 (19)	C8'—C1'—C6'	107.78 (19)
C6—C1—C7	112.5 (2)	C7'—C1'—C6'	112.3 (2)
C3—C2—C9	122.9 (2)	C3'—C2'—C9'	121.6 (2)
C3—C2—C1	122.7 (2)	C3'—C2'—C1'	122.9 (2)
C9—C2—C1	114.3 (2)	C9'—C2'—C1'	115.5 (2)
C2—C3—C4	118.6 (2)	C2'—C3'—C4'	118.7 (2)
C2—C3—C11	122.6 (2)	C2'—C3'—C11'	122.3 (2)
C4—C3—C11	118.5 (2)	C4'—C3'—C11'	118.8 (2)
C12—C4—C3	126.8 (2)	C12'—C4'—C3'	126.7 (2)
C12—C4—C5	123.9 (2)	C12'—C4'—C5'	123.9 (2)
C3—C4—C5	109.21 (19)	C3'—C4'—C5'	109.3 (2)
C13—C5—C6	125.7 (2)	C13'—C5'—C6'	125.1 (2)
C13—C5—C4	123.8 (2)	C13'—C5'—C4'	123.9 (2)
C6—C5—C4	109.9 (2)	C6'—C5'—C4'	110.3 (2)
C14—C6—C5	122.0 (2)	C14'—C6'—C5'	121.7 (2)
C14—C6—C1	125.1 (2)	C14'—C6'—C1'	125.8 (2)
C5—C6—C1	112.90 (19)	C5'—C6'—C1'	112.57 (19)
C1—C7—H7A	109.5	C1'—C7'—H7'1	109.5
C1—C7—H7B	109.5	C1'—C7'—H7'2	109.5
H7A—C7—H7B	109.5	H7'1—C7'—H7'2	109.5
C1—C7—H7C	109.5	C1'—C7'—H7'3	109.5
H7A—C7—H7C	109.5	H7'1—C7'—H7'3	109.5
H7B—C7—H7C	109.5	H7'2—C7'—H7'3	109.5
C1—C8—H8A	109.5	C1'—C8'—H8'1	109.5
C1—C8—H8B	109.5	C1'—C8'—H8'2	109.5
H8A—C8—H8B	109.5	H8'1—C8'—H8'2	109.5
C1—C8—H8C	109.5	C1'—C8'—H8'3	109.5
H8A—C8—H8C	109.5	H8'1—C8'—H8'3	109.5
H8B—C8—H8C	109.5	H8'2—C8'—H8'3	109.5
C10—C9—C2	127.6 (2)	C10'—C9'—C2'	126.8 (2)
C10—C9—H9	116.2	C10'—C9'—H9'	116.6
C2—C9—H9	116.2	C2'—C9'—H9'	116.6
C9—C10—C16	124.2 (2)	C9'—C10'—C16'	124.1 (3)
C9—C10—C15	121.0 (3)	C9'—C10'—C15'	121.2 (3)
C16—C10—C15	114.8 (3)	C16'—C10'—C15'	114.8 (3)
C18—C11—C17	120.6 (2)	C18'—C11'—C17'	121.1 (2)
C18—C11—C3	120.0 (2)	C18'—C11'—C3'	119.9 (2)
C17—C11—C3	119.3 (2)	C17'—C11'—C3'	119.0 (2)
C4—C12—C19	124.8 (2)	C4'—C12'—C20'	122.5 (2)
C4—C12—C20	122.1 (2)	C4'—C12'—C19'	124.9 (2)
C19—C12—C20	113.1 (2)	C20'—C12'—C19'	112.6 (2)
C5—C13—C22	123.4 (2)	C5'—C13'—C22'	123.7 (2)
C5—C13—C21	122.8 (2)	C5'—C13'—C21'	122.5 (2)
C22—C13—C21	113.8 (2)	C22'—C13'—C21'	113.7 (2)
C6—C14—C23	123.1 (2)	C6'—C14'—C23'	122.7 (2)
C6—C14—C24	126.4 (2)	C6'—C14'—C24'	126.7 (2)
C23—C14—C24	110.5 (2)	C23'—C14'—C24'	110.6 (2)
C10—C15—H15A	109.5	C10'—C15'—H15D	109.5
C10—C15—H15B	109.5	C10'—C15'—H15E	109.5
H15A—C15—H15B	109.5	H15D—C15'—H15E	109.5
C10—C15—H15C	109.5	C10'—C15'—H15F	109.5
H15A—C15—H15C	109.5	H15D—C15'—H15F	109.5
H15B—C15—H15C	109.5	H15E—C15'—H15F	109.5
C10—C16—H16A	109.5	C10'—C16'—H16D	109.5
C10—C16—H16B	109.5	C10'—C16'—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16'—H16E	109.5
C10—C16—H16C	109.5	C10'—C16'—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16'—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16'—H16F	109.5
C11—C17—H17A	109.5	C11'—C17'—H17D	109.5
C11—C17—H17B	109.5	C11'—C17'—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17'—H17E	109.5
C11—C17—H17C	109.5	C11'—C17'—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17'—H17F	109.5
C11—C18—H18A	120.0	C11'—C18'—H18C	120.0
C11—C18—H18B	120.0	C11'—C18'—H18D	120.0
H18A—C18—H18B	120.0	H18C—C18'—H18D	120.0
C12—C19—H19A	109.5	C12'—C19'—H19D	109.5
C12—C19—H19B	109.5	C12'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C12—C19—H19C	109.5	C12'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
C12—C20—H20A	109.5	C12'—C20'—H20D	109.5
C12—C20—H20B	109.5	C12'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C12—C20—H20C	109.5	C12'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
C13—C21—H21A	109.5	C13'—C21'—H21D	109.5
C13—C21—H21B	109.5	C13'—C21'—H21E	109.5
H21A—C21—H21B	109.5	H21D—C21'—H21E	109.5
C13—C21—H21C	109.5	C13'—C21'—H21F	109.5
H21A—C21—H21C	109.5	H21D—C21'—H21F	109.5
H21B—C21—H21C	109.5	H21E—C21'—H21F	109.5
C13—C22—H22A	109.5	C13'—C22'—H22D	109.5
C13—C22—H22B	109.5	C13'—C22'—H22E	109.5
H22A—C22—H22B	109.5	H22D—C22'—H22E	109.5
C13—C22—H22C	109.5	C13'—C22'—H22F	109.5
H22A—C22—H22C	109.5	H22D—C22'—H22F	109.5
H22B—C22—H22C	109.5	H22E—C22'—H22F	109.5
C14—C23—H23A	109.5	C14'—C23'—H23D	109.5
C14—C23—H23B	109.5	C14'—C23'—H23E	109.5
H23A—C23—H23B	109.5	H23D—C23'—H23E	109.5
C14—C23—H23C	109.5	C14'—C23'—H23F	109.5
H23A—C23—H23C	109.5	H23D—C23'—H23F	109.5
H23B—C23—H23C	109.5	H23E—C23'—H23F	109.5
C14—C24—H24A	109.5	C14'—C24'—H24D	109.5
C14—C24—H24B	109.5	C14'—C24'—H24E	109.5
H24A—C24—H24B	109.5	H24D—C24'—H24E	109.5
C14—C24—H24C	109.5	C14'—C24'—H24F	109.5
H24A—C24—H24C	109.5	H24D—C24'—H24F	109.5
H24B—C24—H24C	109.5	H24E—C24'—H24F	109.5
C8—C1—C2—C3	−140.8 (2)	C8'—C1'—C2'—C3'	−140.6 (2)
C6—C1—C2—C3	−22.3 (3)	C7'—C1'—C2'—C3'	101.1 (3)
C7—C1—C2—C3	100.2 (3)	C6'—C1'—C2'—C3'	−21.3 (3)
C8—C1—C2—C9	42.2 (3)	C8'—C1'—C2'—C9'	42.4 (3)
C6—C1—C2—C9	160.7 (2)	C7'—C1'—C2'—C9'	−75.9 (3)
C7—C1—C2—C9	−76.8 (2)	C6'—C1'—C2'—C9'	161.7 (2)
C9—C2—C3—C4	−169.4 (2)	C9'—C2'—C3'—C4'	−169.8 (2)
C1—C2—C3—C4	13.8 (3)	C1'—C2'—C3'—C4'	13.3 (3)
C9—C2—C3—C11	4.2 (4)	C9'—C2'—C3'—C11'	4.4 (4)
C1—C2—C3—C11	−172.5 (2)	C1'—C2'—C3'—C11'	−172.5 (2)
C2—C3—C4—C12	−147.9 (2)	C2'—C3'—C4'—C12'	−147.5 (2)
C11—C3—C4—C12	38.1 (3)	C11'—C3'—C4'—C12'	38.2 (3)
C2—C3—C4—C5	29.5 (3)	C2'—C3'—C4'—C5'	29.2 (3)
C11—C3—C4—C5	−144.4 (2)	C11'—C3'—C4'—C5'	−145.2 (2)
C12—C4—C5—C13	−75.4 (3)	C12'—C4'—C5'—C13'	−76.0 (3)
C3—C4—C5—C13	107.1 (3)	C3'—C4'—C5'—C13'	107.3 (3)
C12—C4—C5—C6	113.0 (3)	C12'—C4'—C5'—C6'	112.5 (3)
C3—C4—C5—C6	−64.5 (2)	C3'—C4'—C5'—C6'	−64.2 (2)
C13—C5—C6—C14	64.7 (3)	C13'—C5'—C6'—C14'	64.9 (3)
C4—C5—C6—C14	−123.9 (2)	C4'—C5'—C6'—C14'	−123.7 (2)
C13—C5—C6—C1	−115.5 (3)	C13'—C5'—C6'—C1'	−115.4 (3)
C4—C5—C6—C1	55.9 (3)	C4'—C5'—C6'—C1'	56.0 (3)
C8—C1—C6—C14	−73.9 (3)	C2'—C1'—C6'—C14'	165.5 (2)
C2—C1—C6—C14	166.2 (2)	C8'—C1'—C6'—C14'	−74.5 (3)
C7—C1—C6—C14	48.1 (3)	C7'—C1'—C6'—C14'	47.2 (3)
C8—C1—C6—C5	106.3 (2)	C2'—C1'—C6'—C5'	−14.2 (3)
C2—C1—C6—C5	−13.6 (3)	C8'—C1'—C6'—C5'	105.8 (2)
C7—C1—C6—C5	−131.7 (2)	C7'—C1'—C6'—C5'	−132.4 (2)
C3—C2—C9—C10	61.1 (4)	C3'—C2'—C9'—C10'	61.6 (4)
C1—C2—C9—C10	−121.9 (3)	C1'—C2'—C9'—C10'	−121.4 (3)
C2—C9—C10—C16	−0.4 (5)	C2'—C9'—C10'—C16'	1.9 (4)
C2—C9—C10—C15	179.4 (3)	C2'—C9'—C10'—C15'	−177.5 (3)
C2—C3—C11—C18	−127.2 (3)	C2'—C3'—C11'—C18'	−126.4 (3)
C4—C3—C11—C18	46.4 (3)	C4'—C3'—C11'—C18'	47.7 (3)
C2—C3—C11—C17	55.1 (3)	C2'—C3'—C11'—C17'	56.3 (3)
C4—C3—C11—C17	−131.2 (3)	C4'—C3'—C11'—C17'	−129.5 (2)
C3—C4—C12—C19	2.8 (4)	C3'—C4'—C12'—C20'	−178.9 (2)
C5—C4—C12—C19	−174.3 (2)	C5'—C4'—C12'—C20'	4.9 (4)
C3—C4—C12—C20	−179.0 (2)	C3'—C4'—C12'—C19'	2.3 (4)
C5—C4—C12—C20	4.0 (4)	C5'—C4'—C12'—C19'	−173.9 (2)
C6—C5—C13—C22	−2.6 (4)	C6'—C5'—C13'—C22'	−3.6 (4)
C4—C5—C13—C22	−172.9 (2)	C4'—C5'—C13'—C22'	−173.8 (2)
C6—C5—C13—C21	176.7 (2)	C6'—C5'—C13'—C21'	176.7 (2)
C4—C5—C13—C21	6.4 (4)	C4'—C5'—C13'—C21'	6.5 (4)
C5—C6—C14—C23	2.0 (4)	C5'—C6'—C14'—C23'	3.8 (4)
C1—C6—C14—C23	−177.8 (2)	C1'—C6'—C14'—C23'	−175.8 (2)
C5—C6—C14—C24	−178.8 (2)	C5'—C6'—C14'—C24'	−177.5 (2)
C1—C6—C14—C24	1.4 (4)	C1'—C6'—C14'—C24'	2.9 (4)