rac-7,7',9,9'-Tetra-phenyl-9a,9a'-bi(7,8,9,9a-tetra-hydro-6aH-penta-leno[1,2,3-ij]naphthalen-8-one).

The racemic title compound, C(54)H(38)O(2), consists of two C-linked penta-leno[1,2,3-ij]naphthalenone moieties, the crowded aryl ring substitution on the cyclo-pentane rings forcing the two segments to assume a conformation which has pseudo-twofold rotational symmetry, with a dihedral angle between the naphthalene substituent groups of 55.30 (8)°. In each segment, the two phenyl rings have different conformational orientations, with inter-ring dihedral angles of 34.7 (2) and 49.63 (16)°. Each cyclo-pentane ring has the same relative configuration in its four chiral centres and together with the fused naphthalene ring assumes an overall chair-like conformation.

Related literature

For photoluminescence properties of naphthalene compounds, see: Cai et al. (2010 ▶); Haneline et al. (2002 ▶); Koning et al. (2003 ▶); Tsubaki et al. (2006 ▶). For a related structure, see: Dyker (1993 ▶).

Experimental

Crystal data

C54H38O2

M = 718.84

Monoclinic,

a = 14.325 (3) Å

b = 13.448 (3) Å

c = 19.914 (4) Å

β = 101.449 (5)°

V = 3759.9 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 275 K

0.23 × 0.22 × 0.19 mm

Data collection

Bruker CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.986

42062 measured reflections

8342 independent reflections

4812 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.161

S = 1.05

8342 reflections

505 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014146/zs2187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014146/zs2187Isup2.hkl

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

C54H38O2	F(000) = 1512
Mr = 718.84	Dx = 1.270 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 42062 reflections
a = 14.325 (3) Å	θ = 2.6–27.7°
b = 13.448 (3) Å	µ = 0.08 mm−1
c = 19.914 (4) Å	T = 275 K
β = 101.449 (5)°	Block, colorless
V = 3759.9 (14) Å3	0.23 × 0.22 × 0.19 mm
Z = 4

Bruker CCD area-detector diffractometer	8342 independent reflections
Radiation source: fine-focus sealed tube	4812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 27.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.983, Tmax = 0.986	k = −15→17
42062 measured reflections	l = −25→22

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0377P)2 + 2.9173P] where P = (Fo2 + 2Fc2)/3
8342 reflections	(Δ/σ)max < 0.001
505 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.44413 (13)	0.31609 (14)	0.25183 (10)	0.0548 (5)
O1'	0.14712 (15)	0.08762 (17)	−0.05330 (12)	0.0808 (7)
C1	0.36038 (18)	0.30516 (18)	0.22892 (12)	0.0412 (6)
C1'	0.16606 (19)	0.1682 (2)	−0.02781 (15)	0.0553 (7)
C2	0.31861 (17)	0.22012 (18)	0.18147 (12)	0.0424 (6)
H2	0.3620	0.2062	0.1503	0.051*
C2'	0.25646 (18)	0.18987 (19)	0.02529 (13)	0.0458 (6)
H2'	0.2660	0.1355	0.0587	0.055*
C3	0.22333 (16)	0.26340 (18)	0.13837 (12)	0.0388 (6)
C3'	0.23484 (17)	0.28710 (18)	0.06285 (12)	0.0402 (6)
C4	0.20277 (17)	0.36262 (18)	0.17678 (12)	0.0400 (6)
H4	0.2057	0.4205	0.1474	0.048*
C4'	0.13773 (18)	0.32998 (19)	0.01889 (12)	0.0444 (6)
H4'	0.0882	0.3299	0.0465	0.053*
C5	0.28023 (17)	0.37074 (18)	0.24304 (12)	0.0408 (6)
H5	0.2544	0.3381	0.2794	0.049*
C5'	0.10759 (19)	0.2619 (2)	−0.04458 (14)	0.0549 (7)
H5'	0.1307	0.2942	−0.0823	0.066*
C6	0.31185 (18)	0.12745 (18)	0.22407 (13)	0.0423 (6)
C6'	0.34115 (18)	0.1922 (2)	−0.00976 (13)	0.0463 (6)
C7	0.3683 (2)	0.0463 (2)	0.21658 (16)	0.0584 (7)
H7	0.4090	0.0493	0.1856	0.070*
C7'	0.4174 (2)	0.1298 (2)	0.01212 (16)	0.0647 (8)
H7'	0.4168	0.0868	0.0486	0.078*
C8	0.3647 (2)	−0.0398 (2)	0.2549 (2)	0.0776 (10)
H8	0.4020	−0.0944	0.2488	0.093*
C8'	0.4955 (2)	0.1306 (3)	−0.0199 (2)	0.0807 (10)
H8'	0.5467	0.0884	−0.0044	0.097*
C9	0.3061 (2)	−0.0439 (3)	0.30166 (19)	0.0764 (10)
H9	0.3040	−0.1013	0.3274	0.092*
C9'	0.4979 (2)	0.1925 (3)	−0.0738 (2)	0.0768 (10)
H9'	0.5499	0.1921	−0.0953	0.092*
C10	0.2513 (2)	0.0357 (2)	0.31033 (15)	0.0602 (8)
H10	0.2119	0.0328	0.3422	0.072*
C10'	0.4226 (2)	0.2553 (3)	−0.09590 (15)	0.0642 (8)
H10'	0.4237	0.2982	−0.1323	0.077*
C11	0.2539 (2)	0.1205 (2)	0.27215 (13)	0.0510 (7)
H11	0.2160	0.1744	0.2787	0.061*
C11'	0.3453 (2)	0.2549 (2)	−0.06445 (13)	0.0549 (7)
H11'	0.2947	0.2977	−0.0802	0.066*
C12	0.13540 (17)	0.19949 (19)	0.13976 (12)	0.0431 (6)
C12'	0.30568 (18)	0.37184 (19)	0.06057 (12)	0.0428 (6)
C13	0.1127 (2)	0.1028 (2)	0.12165 (15)	0.0569 (7)
H13	0.1555	0.0628	0.1045	0.068*
C13'	0.40160 (19)	0.3802 (2)	0.08404 (13)	0.0501 (7)
H13'	0.4362	0.3274	0.1067	0.060*
C14	0.0239 (2)	0.0648 (3)	0.12933 (17)	0.0703 (9)
H14	0.0086	−0.0004	0.1160	0.084*
C14'	0.4475 (2)	0.4701 (2)	0.07354 (15)	0.0624 (8)
H14'	0.5128	0.4754	0.0896	0.075*
C15	−0.0401 (2)	0.1193 (3)	0.15528 (16)	0.0685 (9)
H15	−0.0984	0.0915	0.1587	0.082*
C15'	0.3997 (2)	0.5494 (2)	0.04072 (16)	0.0661 (9)
H15'	0.4323	0.6077	0.0354	0.079*
C16	−0.0753 (2)	0.2827 (3)	0.20793 (16)	0.0697 (9)
H16	−0.1352	0.2624	0.2138	0.084*
C16'	0.2416 (3)	0.6173 (2)	−0.02160 (16)	0.0712 (9)
H16'	0.2672	0.6786	−0.0299	0.085*
C17	−0.0424 (2)	0.3745 (3)	0.22916 (16)	0.0728 (10)
H17	−0.0803	0.4154	0.2503	0.087*
C17'	0.1474 (3)	0.5996 (2)	−0.04458 (16)	0.0733 (10)
H17'	0.1098	0.6497	−0.0681	0.088*
C18	0.0470 (2)	0.4105 (2)	0.22040 (14)	0.0599 (8)
H18	0.0673	0.4739	0.2351	0.072*
C18'	0.1045 (2)	0.5084 (2)	−0.03424 (14)	0.0624 (8)
H18'	0.0400	0.4979	−0.0512	0.075*
C19	0.10300 (17)	0.3502 (2)	0.18994 (13)	0.0453 (6)
C19'	0.15998 (19)	0.4353 (2)	0.00136 (12)	0.0477 (6)
C20	−0.01890 (19)	0.2181 (2)	0.17719 (14)	0.0567 (8)
C20'	0.3014 (2)	0.5432 (2)	0.01489 (14)	0.0567 (7)
C21	0.07006 (17)	0.2551 (2)	0.16821 (13)	0.0451 (6)
C21'	0.25666 (19)	0.45336 (19)	0.02589 (12)	0.0444 (6)
C22	0.30952 (17)	0.47445 (19)	0.26837 (13)	0.0458 (6)
C22'	0.0013 (2)	0.2486 (3)	−0.06871 (15)	0.0640 (8)
C23	0.3551 (2)	0.5379 (2)	0.23124 (17)	0.0648 (8)
H23	0.3667	0.5175	0.1891	0.078*
C23'	−0.0474 (3)	0.3071 (3)	−0.12167 (17)	0.0907 (12)
H23'	−0.0141	0.3523	−0.1433	0.109*
C24	0.3837 (2)	0.6309 (2)	0.2554 (2)	0.0819 (11)
H24	0.4149	0.6724	0.2296	0.098*
C24'	−0.1452 (3)	0.2986 (5)	−0.1425 (2)	0.1201 (19)
H24'	−0.1773	0.3395	−0.1772	0.144*
C25	0.3669 (3)	0.6630 (3)	0.3166 (3)	0.0902 (13)
H25	0.3866	0.7260	0.3327	0.108*
C25'	−0.1948 (3)	0.2307 (5)	−0.1127 (3)	0.122 (2)
H25'	−0.2602	0.2243	−0.1278	0.147*
C26	0.3203 (3)	0.6012 (3)	0.3549 (2)	0.0913 (12)
H26	0.3081	0.6227	0.3967	0.110*
C26'	−0.1475 (3)	0.1711 (4)	−0.0598 (3)	0.1068 (15)
H26'	−0.1808	0.1246	−0.0392	0.128*
C27	0.2920 (2)	0.5070 (2)	0.33056 (15)	0.0643 (8)
H27	0.2609	0.4654	0.3563	0.077*
C27'	−0.0500 (2)	0.1820 (3)	−0.0381 (2)	0.0796 (10)
H27'	−0.0185	0.1433	−0.0019	0.095*

	U11	U22	U33	U12	U13	U23
O1	0.0416 (11)	0.0534 (12)	0.0663 (12)	−0.0047 (9)	0.0033 (9)	0.0017 (10)
O1'	0.0679 (14)	0.0671 (15)	0.1050 (18)	−0.0086 (12)	0.0112 (12)	−0.0422 (14)
C1	0.0422 (15)	0.0393 (14)	0.0415 (13)	−0.0041 (11)	0.0070 (11)	0.0061 (11)
C1'	0.0504 (16)	0.0584 (19)	0.0589 (17)	−0.0060 (14)	0.0153 (13)	−0.0190 (15)
C2	0.0439 (14)	0.0398 (14)	0.0457 (14)	−0.0009 (12)	0.0139 (11)	−0.0013 (12)
C2'	0.0501 (15)	0.0422 (15)	0.0458 (14)	0.0008 (12)	0.0113 (12)	−0.0050 (12)
C3	0.0388 (13)	0.0362 (13)	0.0424 (13)	−0.0013 (11)	0.0103 (10)	−0.0029 (11)
C3'	0.0422 (14)	0.0370 (13)	0.0418 (13)	−0.0014 (11)	0.0093 (11)	−0.0041 (11)
C4	0.0438 (14)	0.0372 (14)	0.0391 (13)	0.0001 (11)	0.0085 (10)	−0.0005 (11)
C4'	0.0438 (14)	0.0475 (15)	0.0417 (13)	0.0018 (12)	0.0077 (11)	−0.0050 (12)
C5	0.0430 (13)	0.0402 (14)	0.0404 (13)	−0.0050 (11)	0.0113 (11)	−0.0011 (11)
C5'	0.0537 (16)	0.0622 (19)	0.0471 (15)	−0.0011 (14)	0.0054 (12)	−0.0112 (14)
C6	0.0451 (14)	0.0334 (13)	0.0458 (14)	−0.0012 (11)	0.0025 (11)	−0.0004 (11)
C6'	0.0472 (15)	0.0460 (15)	0.0459 (14)	0.0026 (12)	0.0100 (12)	−0.0120 (13)
C7	0.0517 (17)	0.0484 (17)	0.075 (2)	0.0056 (14)	0.0110 (14)	0.0065 (15)
C7'	0.0641 (19)	0.0612 (19)	0.071 (2)	0.0147 (16)	0.0173 (16)	−0.0021 (16)
C8	0.070 (2)	0.0497 (19)	0.112 (3)	0.0177 (17)	0.014 (2)	0.018 (2)
C8'	0.062 (2)	0.077 (2)	0.105 (3)	0.0181 (19)	0.023 (2)	−0.007 (2)
C9	0.074 (2)	0.055 (2)	0.097 (3)	−0.0004 (18)	0.009 (2)	0.0269 (19)
C9'	0.061 (2)	0.085 (3)	0.091 (3)	−0.0031 (19)	0.0328 (19)	−0.018 (2)
C10	0.0663 (19)	0.0526 (18)	0.0603 (18)	−0.0105 (16)	0.0094 (15)	0.0125 (15)
C10'	0.0635 (19)	0.077 (2)	0.0558 (17)	−0.0107 (18)	0.0203 (15)	−0.0122 (16)
C11	0.0588 (17)	0.0430 (15)	0.0518 (16)	−0.0023 (13)	0.0121 (13)	0.0050 (13)
C11'	0.0514 (16)	0.0658 (19)	0.0474 (15)	0.0002 (14)	0.0095 (13)	−0.0074 (14)
C12	0.0431 (14)	0.0419 (14)	0.0442 (14)	−0.0050 (12)	0.0083 (11)	0.0044 (12)
C12'	0.0473 (15)	0.0423 (15)	0.0406 (13)	−0.0064 (12)	0.0131 (11)	−0.0057 (12)
C13	0.0577 (17)	0.0462 (17)	0.0664 (18)	−0.0127 (14)	0.0116 (14)	−0.0028 (14)
C13'	0.0538 (16)	0.0534 (17)	0.0460 (15)	−0.0045 (14)	0.0167 (12)	−0.0005 (13)
C14	0.065 (2)	0.061 (2)	0.081 (2)	−0.0229 (17)	0.0041 (17)	0.0055 (18)
C14'	0.0587 (18)	0.069 (2)	0.0630 (18)	−0.0216 (16)	0.0197 (15)	−0.0025 (17)
C15	0.0510 (18)	0.077 (2)	0.075 (2)	−0.0225 (17)	0.0071 (16)	0.0205 (19)
C15'	0.089 (2)	0.0524 (19)	0.0639 (19)	−0.0241 (18)	0.0311 (17)	−0.0038 (16)
C16	0.0465 (17)	0.103 (3)	0.0613 (19)	−0.0004 (19)	0.0151 (15)	0.013 (2)
C16'	0.115 (3)	0.0438 (18)	0.0616 (19)	−0.0006 (19)	0.033 (2)	0.0073 (16)
C17	0.0518 (18)	0.107 (3)	0.063 (2)	0.019 (2)	0.0195 (15)	−0.002 (2)
C17'	0.109 (3)	0.054 (2)	0.0602 (19)	0.021 (2)	0.0232 (19)	0.0123 (16)
C18	0.0530 (17)	0.070 (2)	0.0572 (17)	0.0113 (15)	0.0114 (14)	−0.0083 (15)
C18'	0.076 (2)	0.063 (2)	0.0487 (16)	0.0175 (17)	0.0138 (15)	0.0059 (15)
C19	0.0390 (14)	0.0543 (17)	0.0427 (14)	0.0057 (12)	0.0086 (11)	0.0020 (12)
C19'	0.0604 (17)	0.0467 (16)	0.0372 (13)	0.0046 (13)	0.0131 (12)	−0.0011 (12)
C20	0.0436 (15)	0.074 (2)	0.0522 (16)	−0.0029 (15)	0.0086 (13)	0.0191 (15)
C20'	0.084 (2)	0.0453 (17)	0.0466 (15)	−0.0068 (16)	0.0260 (15)	−0.0025 (13)
C21	0.0368 (13)	0.0523 (16)	0.0457 (14)	−0.0018 (12)	0.0068 (11)	0.0094 (13)
C21'	0.0596 (17)	0.0410 (15)	0.0359 (13)	−0.0038 (13)	0.0173 (12)	−0.0022 (11)
C22	0.0409 (14)	0.0418 (15)	0.0520 (15)	0.0010 (12)	0.0028 (11)	−0.0026 (13)
C22'	0.0517 (17)	0.080 (2)	0.0557 (18)	0.0043 (17)	−0.0005 (14)	−0.0268 (17)
C23	0.069 (2)	0.0473 (17)	0.080 (2)	−0.0124 (15)	0.0178 (17)	−0.0042 (16)
C23'	0.075 (2)	0.133 (4)	0.057 (2)	0.021 (2)	−0.0047 (18)	−0.013 (2)
C24	0.069 (2)	0.0457 (19)	0.126 (3)	−0.0097 (17)	0.006 (2)	0.000 (2)
C24'	0.071 (3)	0.192 (6)	0.082 (3)	0.038 (3)	−0.021 (2)	−0.039 (3)
C25	0.078 (3)	0.044 (2)	0.132 (4)	0.0008 (18)	−0.019 (2)	−0.028 (2)
C25'	0.053 (3)	0.178 (6)	0.128 (4)	0.009 (3)	−0.002 (3)	−0.079 (4)
C26	0.106 (3)	0.074 (3)	0.083 (3)	0.015 (2)	−0.007 (2)	−0.040 (2)
C26'	0.059 (2)	0.115 (4)	0.148 (4)	−0.011 (2)	0.022 (3)	−0.057 (3)
C27	0.073 (2)	0.061 (2)	0.0580 (18)	0.0023 (16)	0.0109 (15)	−0.0106 (16)
C27'	0.055 (2)	0.087 (3)	0.095 (3)	−0.0116 (19)	0.0107 (18)	−0.028 (2)

O1—C1	1.205 (3)	C13—C14	1.407 (4)
O1'—C1'	1.204 (3)	C13—H13	0.9300
C1—C5	1.518 (3)	C13'—C14'	1.412 (4)
C1—C2	1.528 (3)	C13'—H13'	0.9300
C1'—C5'	1.514 (4)	C14—C15	1.354 (4)
C1'—C2'	1.529 (4)	C14—H14	0.9300
C2—C6	1.521 (3)	C14'—C15'	1.362 (4)
C2—C3	1.573 (3)	C14'—H14'	0.9300
C2—H2	0.9800	C15—C20	1.413 (4)
C2'—C6'	1.515 (3)	C15—H15	0.9300
C2'—C3'	1.567 (3)	C15'—C20'	1.402 (4)
C2'—H2'	0.9800	C15'—H15'	0.9300
C3—C12	1.530 (3)	C16—C17	1.360 (5)
C3—C3'	1.578 (3)	C16—C20	1.405 (4)
C3—C4	1.594 (3)	C16—H16	0.9300
C3'—C12'	1.533 (3)	C16'—C17'	1.358 (5)
C3'—C4'	1.597 (3)	C16'—C20'	1.416 (4)
C4—C19	1.512 (3)	C16'—H16'	0.9300
C4—C5	1.550 (3)	C17—C18	1.412 (4)
C4—H4	0.9800	C17—H17	0.9300
C4'—C19'	1.508 (4)	C17'—C18'	1.405 (5)
C4'—C5'	1.551 (3)	C17'—H17'	0.9300
C4'—H4'	0.9800	C18—C19	1.364 (4)
C5—C22	1.514 (3)	C18—H18	0.9300
C5—H5	0.9800	C18'—C19'	1.370 (4)
C5'—C22'	1.514 (4)	C18'—H18'	0.9300
C5'—H5'	0.9800	C19—C21	1.402 (4)
C6—C7	1.383 (4)	C19'—C21'	1.395 (4)
C6—C11	1.389 (4)	C20—C21	1.412 (4)
C6'—C7'	1.378 (4)	C20'—C21'	1.406 (4)
C6'—C11'	1.388 (4)	C22—C23	1.376 (4)
C7—C8	1.394 (4)	C22—C27	1.383 (4)
C7—H7	0.9300	C22'—C27'	1.375 (5)
C7'—C8'	1.394 (4)	C22'—C23'	1.388 (5)
C7'—H7'	0.9300	C23—C24	1.373 (4)
C8—C9	1.373 (5)	C23—H23	0.9300
C8—H8	0.9300	C23'—C24'	1.385 (5)
C8'—C9'	1.363 (5)	C23'—H23'	0.9300
C8'—H8'	0.9300	C24—C25	1.358 (5)
C9—C10	1.359 (4)	C24—H24	0.9300
C9—H9	0.9300	C24'—C25'	1.363 (7)
C9'—C10'	1.372 (5)	C24'—H24'	0.9300
C9'—H9'	0.9300	C25—C26	1.387 (5)
C10—C11	1.375 (4)	C25—H25	0.9300
C10—H10	0.9300	C25'—C26'	1.388 (7)
C10'—C11'	1.375 (4)	C25'—H25'	0.9300
C10'—H10'	0.9300	C26—C27	1.388 (5)
C11—H11	0.9300	C26—H26	0.9300
C11'—H11'	0.9300	C26'—C27'	1.385 (5)
C12—C13	1.371 (4)	C26'—H26'	0.9300
C12—C21	1.402 (3)	C27—H27	0.9300
C12'—C13'	1.365 (3)	C27'—H27'	0.9300
C12'—C21'	1.407 (3)
O1—C1—C5	126.3 (2)	C13'—C12'—C21'	118.3 (2)
O1—C1—C2	124.3 (2)	C13'—C12'—C3'	132.7 (2)
C5—C1—C2	109.4 (2)	C21'—C12'—C3'	109.0 (2)
O1'—C1'—C5'	126.0 (3)	C12—C13—C14	119.2 (3)
O1'—C1'—C2'	123.5 (3)	C12—C13—H13	120.4
C5'—C1'—C2'	110.4 (2)	C14—C13—H13	120.4
C6—C2—C1	109.19 (19)	C12'—C13'—C14'	119.1 (3)
C6—C2—C3	117.6 (2)	C12'—C13'—H13'	120.4
C1—C2—C3	104.56 (19)	C14'—C13'—H13'	120.4
C6—C2—H2	108.4	C15—C14—C13	122.8 (3)
C1—C2—H2	108.4	C15—C14—H14	118.6
C3—C2—H2	108.4	C13—C14—H14	118.6
C6'—C2'—C1'	109.3 (2)	C15'—C14'—C13'	122.5 (3)
C6'—C2'—C3'	117.0 (2)	C15'—C14'—H14'	118.8
C1'—C2'—C3'	105.6 (2)	C13'—C14'—H14'	118.8
C6'—C2'—H2'	108.2	C14—C15—C20	120.4 (3)
C1'—C2'—H2'	108.2	C14—C15—H15	119.8
C3'—C2'—H2'	108.2	C20—C15—H15	119.8
C12—C3—C2	114.3 (2)	C14'—C15'—C20'	120.1 (3)
C12—C3—C3'	111.90 (19)	C14'—C15'—H15'	119.9
C2—C3—C3'	110.57 (18)	C20'—C15'—H15'	119.9
C12—C3—C4	103.32 (18)	C17—C16—C20	120.2 (3)
C2—C3—C4	105.72 (18)	C17—C16—H16	119.9
C3'—C3—C4	110.64 (19)	C20—C16—H16	119.9
C12'—C3'—C2'	114.3 (2)	C17'—C16'—C20'	120.6 (3)
C12'—C3'—C3	111.93 (19)	C17'—C16'—H16'	119.7
C2'—C3'—C3	110.7 (2)	C20'—C16'—H16'	119.7
C12'—C3'—C4'	103.0 (2)	C16—C17—C18	122.6 (3)
C2'—C3'—C4'	105.83 (19)	C16—C17—H17	118.7
C3—C3'—C4'	110.55 (19)	C18—C17—H17	118.7
C19—C4—C5	113.7 (2)	C16'—C17'—C18'	122.6 (3)
C19—C4—C3	105.17 (19)	C16'—C17'—H17'	118.7
C5—C4—C3	107.35 (19)	C18'—C17'—H17'	118.7
C19—C4—H4	110.2	C19—C18—C17	118.7 (3)
C5—C4—H4	110.2	C19—C18—H18	120.7
C3—C4—H4	110.2	C17—C18—H18	120.7
C19'—C4'—C5'	113.8 (2)	C19'—C18'—C17'	118.5 (3)
C19'—C4'—C3'	105.4 (2)	C19'—C18'—H18'	120.8
C5'—C4'—C3'	107.8 (2)	C17'—C18'—H18'	120.8
C19'—C4'—H4'	109.9	C18—C19—C21	119.2 (2)
C5'—C4'—H4'	109.9	C18—C19—C4	132.1 (3)
C3'—C4'—H4'	109.9	C21—C19—C4	108.6 (2)
C22—C5—C1	115.3 (2)	C18'—C19'—C21'	119.3 (3)
C22—C5—C4	116.9 (2)	C18'—C19'—C4'	131.8 (3)
C1—C5—C4	103.97 (19)	C21'—C19'—C4'	108.9 (2)
C22—C5—H5	106.7	C16—C20—C21	116.7 (3)
C1—C5—H5	106.7	C16—C20—C15	127.5 (3)
C4—C5—H5	106.7	C21—C20—C15	115.9 (3)
C1'—C5'—C22'	116.7 (3)	C15'—C20'—C21'	116.7 (3)
C1'—C5'—C4'	105.0 (2)	C15'—C20'—C16'	127.4 (3)
C22'—C5'—C4'	115.4 (2)	C21'—C20'—C16'	115.9 (3)
C1'—C5'—H5'	106.3	C19—C21—C12	113.6 (2)
C22'—C5'—H5'	106.3	C19—C21—C20	122.6 (3)
C4'—C5'—H5'	106.3	C12—C21—C20	123.7 (3)
C7—C6—C11	117.6 (2)	C19'—C21'—C20'	123.2 (3)
C7—C6—C2	118.8 (2)	C19'—C21'—C12'	113.6 (2)
C11—C6—C2	123.5 (2)	C20'—C21'—C12'	123.2 (3)
C7'—C6'—C11'	117.6 (3)	C23—C22—C27	118.4 (3)
C7'—C6'—C2'	119.9 (3)	C23—C22—C5	121.5 (2)
C11'—C6'—C2'	122.5 (2)	C27—C22—C5	120.2 (2)
C6—C7—C8	120.7 (3)	C27'—C22'—C23'	118.3 (3)
C6—C7—H7	119.7	C27'—C22'—C5'	121.9 (3)
C8—C7—H7	119.7	C23'—C22'—C5'	119.7 (3)
C6'—C7'—C8'	120.6 (3)	C24—C23—C22	121.2 (3)
C6'—C7'—H7'	119.7	C24—C23—H23	119.4
C8'—C7'—H7'	119.7	C22—C23—H23	119.4
C9—C8—C7	119.9 (3)	C24'—C23'—C22'	120.5 (4)
C9—C8—H8	120.0	C24'—C23'—H23'	119.8
C7—C8—H8	120.0	C22'—C23'—H23'	119.8
C9'—C8'—C7'	120.9 (3)	C25—C24—C23	120.6 (4)
C9'—C8'—H8'	119.6	C25—C24—H24	119.7
C7'—C8'—H8'	119.6	C23—C24—H24	119.7
C10—C9—C8	120.1 (3)	C25'—C24'—C23'	120.5 (5)
C10—C9—H9	120.0	C25'—C24'—H24'	119.7
C8—C9—H9	120.0	C23'—C24'—H24'	119.7
C8'—C9'—C10'	119.1 (3)	C24—C25—C26	119.6 (3)
C8'—C9'—H9'	120.4	C24—C25—H25	120.2
C10'—C9'—H9'	120.4	C26—C25—H25	120.2
C9—C10—C11	120.2 (3)	C24'—C25'—C26'	120.0 (4)
C9—C10—H10	119.9	C24'—C25'—H25'	120.0
C11—C10—H10	119.9	C26'—C25'—H25'	120.0
C9'—C10'—C11'	120.3 (3)	C25—C26—C27	119.6 (4)
C9'—C10'—H10'	119.9	C25—C26—H26	120.2
C11'—C10'—H10'	119.9	C27—C26—H26	120.2
C10—C11—C6	121.5 (3)	C27'—C26'—C25'	119.1 (5)
C10—C11—H11	119.3	C27'—C26'—H26'	120.5
C6—C11—H11	119.3	C25'—C26'—H26'	120.5
C10'—C11'—C6'	121.6 (3)	C22—C27—C26	120.6 (3)
C10'—C11'—H11'	119.2	C22—C27—H27	119.7
C6'—C11'—H11'	119.2	C26—C27—H27	119.7
C13—C12—C21	118.0 (2)	C22'—C27'—C26'	121.6 (4)
C13—C12—C3	132.9 (2)	C22'—C27'—H27'	119.2
C21—C12—C3	109.0 (2)	C26'—C27'—H27'	119.2
O1—C1—C2—C6	80.6 (3)	C2'—C3'—C12'—C13'	−60.7 (4)
C5—C1—C2—C6	−98.4 (2)	C3—C3'—C12'—C13'	66.2 (3)
O1—C1—C2—C3	−152.8 (2)	C4'—C3'—C12'—C13'	−175.0 (3)
C5—C1—C2—C3	28.3 (2)	C2'—C3'—C12'—C21'	118.3 (2)
O1'—C1'—C2'—C6'	73.5 (4)	C3—C3'—C12'—C21'	−114.8 (2)
C5'—C1'—C2'—C6'	−104.6 (3)	C4'—C3'—C12'—C21'	4.0 (2)
O1'—C1'—C2'—C3'	−159.8 (3)	C21—C12—C13—C14	2.8 (4)
C5'—C1'—C2'—C3'	22.1 (3)	C3—C12—C13—C14	179.9 (3)
C6—C2—C3—C12	−5.6 (3)	C21'—C12'—C13'—C14'	0.8 (4)
C1—C2—C3—C12	−126.8 (2)	C3'—C12'—C13'—C14'	179.8 (2)
C6—C2—C3—C3'	−132.9 (2)	C12—C13—C14—C15	−1.3 (5)
C1—C2—C3—C3'	105.9 (2)	C12'—C13'—C14'—C15'	0.0 (4)
C6—C2—C3—C4	107.3 (2)	C13—C14—C15—C20	−1.1 (5)
C1—C2—C3—C4	−13.9 (2)	C13'—C14'—C15'—C20'	−1.0 (5)
C6'—C2'—C3'—C12'	−1.7 (3)	C20—C16—C17—C18	1.4 (5)
C1'—C2'—C3'—C12'	−123.6 (2)	C20'—C16'—C17'—C18'	−0.5 (5)
C6'—C2'—C3'—C3	−129.3 (2)	C16—C17—C18—C19	−0.6 (5)
C1'—C2'—C3'—C3	108.9 (2)	C16'—C17'—C18'—C19'	1.0 (5)
C6'—C2'—C3'—C4'	110.9 (2)	C17—C18—C19—C21	0.2 (4)
C1'—C2'—C3'—C4'	−11.0 (3)	C17—C18—C19—C4	−175.8 (3)
C12—C3—C3'—C12'	165.0 (2)	C5—C4—C19—C18	63.3 (4)
C2—C3—C3'—C12'	−66.4 (2)	C3—C4—C19—C18	−179.5 (3)
C4—C3—C3'—C12'	50.4 (3)	C5—C4—C19—C21	−113.0 (2)
C12—C3—C3'—C2'	−66.2 (2)	C3—C4—C19—C21	4.2 (3)
C2—C3—C3'—C2'	62.4 (2)	C17'—C18'—C19'—C21'	−0.2 (4)
C4—C3—C3'—C2'	179.22 (19)	C17'—C18'—C19'—C4'	−177.5 (3)
C12—C3—C3'—C4'	50.8 (3)	C5'—C4'—C19'—C18'	63.4 (4)
C2—C3—C3'—C4'	179.41 (19)	C3'—C4'—C19'—C18'	−178.8 (3)
C4—C3—C3'—C4'	−63.8 (2)	C5'—C4'—C19'—C21'	−114.1 (2)
C12—C3—C4—C19	−5.3 (2)	C3'—C4'—C19'—C21'	3.7 (3)
C2—C3—C4—C19	−125.6 (2)	C17—C16—C20—C21	−1.8 (4)
C3'—C3—C4—C19	114.6 (2)	C17—C16—C20—C15	176.8 (3)
C12—C3—C4—C5	116.1 (2)	C14—C15—C20—C16	−176.9 (3)
C2—C3—C4—C5	−4.3 (2)	C14—C15—C20—C21	1.8 (4)
C3'—C3—C4—C5	−124.0 (2)	C14'—C15'—C20'—C21'	1.1 (4)
C12'—C3'—C4'—C19'	−4.5 (2)	C14'—C15'—C20'—C16'	−178.5 (3)
C2'—C3'—C4'—C19'	−124.8 (2)	C17'—C16'—C20'—C15'	178.8 (3)
C3—C3'—C4'—C19'	115.2 (2)	C17'—C16'—C20'—C21'	−0.8 (4)
C12'—C3'—C4'—C5'	117.2 (2)	C18—C19—C21—C12	−178.1 (2)
C2'—C3'—C4'—C5'	−3.0 (3)	C4—C19—C21—C12	−1.2 (3)
C3—C3'—C4'—C5'	−123.0 (2)	C18—C19—C21—C20	−0.7 (4)
O1—C1—C5—C22	20.9 (4)	C4—C19—C21—C20	176.2 (2)
C2—C1—C5—C22	−160.2 (2)	C13—C12—C21—C19	175.2 (2)
O1—C1—C5—C4	150.2 (2)	C3—C12—C21—C19	−2.5 (3)
C2—C1—C5—C4	−30.9 (2)	C13—C12—C21—C20	−2.1 (4)
C19—C4—C5—C22	−95.0 (3)	C3—C12—C21—C20	−179.8 (2)
C3—C4—C5—C22	149.1 (2)	C16—C20—C21—C19	1.5 (4)
C19—C4—C5—C1	136.7 (2)	C15—C20—C21—C19	−177.3 (2)
C3—C4—C5—C1	20.8 (2)	C16—C20—C21—C12	178.6 (2)
O1'—C1'—C5'—C22'	29.0 (4)	C15—C20—C21—C12	−0.2 (4)
C2'—C1'—C5'—C22'	−153.0 (2)	C18'—C19'—C21'—C20'	−1.2 (4)
O1'—C1'—C5'—C4'	158.1 (3)	C4'—C19'—C21'—C20'	176.7 (2)
C2'—C1'—C5'—C4'	−23.9 (3)	C18'—C19'—C21'—C12'	−179.1 (2)
C19'—C4'—C5'—C1'	132.4 (2)	C4'—C19'—C21'—C12'	−1.2 (3)
C3'—C4'—C5'—C1'	16.0 (3)	C15'—C20'—C21'—C19'	−178.0 (2)
C19'—C4'—C5'—C22'	−97.7 (3)	C16'—C20'—C21'—C19'	1.7 (4)
C3'—C4'—C5'—C22'	145.9 (3)	C15'—C20'—C21'—C12'	−0.3 (4)
C1—C2—C6—C7	−113.7 (3)	C16'—C20'—C21'—C12'	179.4 (2)
C3—C2—C6—C7	127.4 (3)	C13'—C12'—C21'—C19'	177.2 (2)
C1—C2—C6—C11	64.2 (3)	C3'—C12'—C21'—C19'	−2.0 (3)
C3—C2—C6—C11	−54.7 (3)	C13'—C12'—C21'—C20'	−0.7 (4)
C1'—C2'—C6'—C7'	−123.1 (3)	C3'—C12'—C21'—C20'	−179.8 (2)
C3'—C2'—C6'—C7'	117.0 (3)	C1—C5—C22—C23	57.1 (3)
C1'—C2'—C6'—C11'	56.2 (3)	C4—C5—C22—C23	−65.6 (3)
C3'—C2'—C6'—C11'	−63.7 (3)	C1—C5—C22—C27	−122.0 (3)
C11—C6—C7—C8	1.6 (4)	C4—C5—C22—C27	115.4 (3)
C2—C6—C7—C8	179.6 (3)	C1'—C5'—C22'—C27'	42.8 (4)
C11'—C6'—C7'—C8'	0.1 (4)	C4'—C5'—C22'—C27'	−81.2 (4)
C2'—C6'—C7'—C8'	179.5 (3)	C1'—C5'—C22'—C23'	−139.5 (3)
C6—C7—C8—C9	−1.3 (5)	C4'—C5'—C22'—C23'	96.5 (3)
C6'—C7'—C8'—C9'	−0.5 (5)	C27—C22—C23—C24	0.8 (4)
C7—C8—C9—C10	0.3 (5)	C5—C22—C23—C24	−178.3 (3)
C7'—C8'—C9'—C10'	0.7 (5)	C27'—C22'—C23'—C24'	0.4 (5)
C8—C9—C10—C11	0.3 (5)	C5'—C22'—C23'—C24'	−177.4 (3)
C8'—C9'—C10'—C11'	−0.7 (5)	C22—C23—C24—C25	−0.6 (5)
C9—C10—C11—C6	0.1 (4)	C22'—C23'—C24'—C25'	−1.9 (6)
C7—C6—C11—C10	−1.0 (4)	C23—C24—C25—C26	−0.1 (6)
C2—C6—C11—C10	−178.9 (2)	C23'—C24'—C25'—C26'	1.6 (7)
C9'—C10'—C11'—C6'	0.3 (4)	C24—C25—C26—C27	0.5 (6)
C7'—C6'—C11'—C10'	−0.1 (4)	C24'—C25'—C26'—C27'	0.1 (7)
C2'—C6'—C11'—C10'	−179.4 (2)	C23—C22—C27—C26	−0.4 (4)
C2—C3—C12—C13	−58.1 (4)	C5—C22—C27—C26	178.7 (3)
C3'—C3—C12—C13	68.5 (4)	C25—C26—C27—C22	−0.2 (5)
C4—C3—C12—C13	−172.4 (3)	C23'—C22'—C27'—C26'	1.3 (5)
C2—C3—C12—C21	119.1 (2)	C5'—C22'—C27'—C26'	179.1 (3)
C3'—C3—C12—C21	−114.2 (2)	C25'—C26'—C27'—C22'	−1.6 (6)
C4—C3—C12—C21	4.8 (3)