2,2'-Bi(9,9-di­hexyl­fluorene)

The central part of the title mol­ecule, C₅₀H₆₆, is planar, all the rings being in the same plane; the lateral chains are also planar (excluding H atoms), almost perpendicular to the ring plane and grafted on the same side of the mol­ecule. The mol­ecule has nearly a mirror plane, perpendicular to the central C-C bond, instead of the centre of symmetry expected. The orientation of the plane of the rings is approximately 45° from the unit-cell b axis, so that neighbouring mol­ecules are essentially perpendicular.

S1. Comment

Conducting polymers based on fluorene repeat units are well known to exhibit attractive luminescent properties allowing for instance the synthesis of blue light electroluminescent devices (Kraft et al., 1998; Stéphan & Vial, 1999). The corresponding polyfluorenes exhibit good thermal and chemical stability, high solubility and good solid-state fluorescence quantum yields. Nevertheless, in the solid state, the formation of film aggregates leads to altered spectrocopic properties (Klarner et al.,1998; Stéphan & Vial,1999). As a result, although the luminescence from isolated chain, such as in dilute solution, is blue, in the solid state, a broad and unstructured red-shifted band emission is observed due to the excimer emission. One way to avoid this excimer emission, which is an important problem, may be to investigate the use of oligomeric polyfluorene segments for which a well defined crystallization may occur. We report here the structure of the shortest oligomer which can be derived from fluorene, i.e. the dimer.

The main result concerning the molecular conformation is that the hexyl chains grafted at the 9 positions are on the same side of the rings, which is uncommon if compared to conducting polymers such as polypyrroles or polythiophenes in which the repeat units are head to foot (Handbook of Conducting Polymers, 1998). We note that one of the chains has a high thermal motion (U_eq for C119 = 0.19 Ų), the three others being normal. This can be explained by the environment, C119 having only one neighbour at less than 4.0 Å, while the others have four or five such neighbours. We tried to refine the structure from low-temperature (193 K) data but, although the displacement parameters are of course globally smaller, U(C119) remains much higher than the others and the refinement is not better than the room-temperature one.

The stacking of the molecules is such that ring planes are perpendicular in neighbouring molecules; there is no π-stacking between the planar conjugated fluorene segments. This result is in agreement with the photoluminescence measurements on dimer crystals, for which the shift leading to yellow instead of blue light is not observed.

S2. Experimental

The title compound was obtained via Ni-catalyzed coupling of 2-bromo-9,9-dihexylfluorene monomeric units. The hexyl chains are grafted in order to allow a high solubility in common organic solvents.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Xtal3.2 SORTRF ADDREF (Hall et al., 1992); program(s) used to solve structure: Xtal3.2 GENTAN; program(s) used to refine structure: Xtal3.2 CRYLSQ; molecular graphics: Xtal3.2 ORTEP; software used to prepare material for publication: Xtal3.2 BONDLA CIFIO.

2,2'-(9,9-dihexyl)bifluorene

Crystal data

C50H66	F(000) = 1463.83
Mr = 667.08	Dx = 1.043 Mg m^−3
Monoclinic, P21/n	Melting point: 333 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.975 (2) Å	Cell parameters from 20 reflections
b = 15.773 (2) Å	θ = 10–12°
c = 17.142 (2) Å	µ = 0.06 mm^−1
β = 100.51 (1)°	T = 293 K
V = 4246.9 (7) Å^3	Parallelepiped, translucent white
Z = 4	0.3 × 0.3 × 0.2 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 25.0°, θmin = 2.1°
ω scans	h = −18→18
7842 measured reflections	k = −5→18
7460 independent reflections	l = −4→20
4526 reflections with refl observed if Inet > .540 σ(Inet)	2 standard reflections every 100 reflections
Rint = 0.017	intensity decay: 1%

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.100	w = 1/(0.1 + 1.4σ^2)
wR(F^2) = 0.039	(Δ/σ)max = 0.003
S = 1.27	Δρmax = 0.35 e Å^−3
4526 reflections	Δρmin = −0.41 e Å^−3
452 parameters	Extinction correction: Zachariasen (1967), Eq22, p. 292_"Cryst._Comp."_Munksgaard_1970
0 restraints	Extinction coefficient: 0.72 (3)

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

	x	y	z	Uiso*/Ueq
C101	0.9304 (2)	0.6177 (2)	0.2301 (2)	0.046 (2)
C102	0.9763 (2)	0.6464 (2)	0.3034 (2)	0.043 (2)
C103	0.9554 (2)	0.6098 (3)	0.3718 (2)	0.057 (3)
C104	0.8935 (2)	0.5481 (3)	0.3689 (2)	0.061 (3)
C105	0.7405 (3)	0.4071 (3)	0.3221 (2)	0.065 (3)
C106	0.6770 (3)	0.3530 (3)	0.2844 (3)	0.078 (3)
C107	0.6555 (3)	0.3496 (3)	0.2031 (3)	0.079 (3)
C108	0.6960 (3)	0.4011 (3)	0.1567 (2)	0.071 (3)
C109	0.8112 (2)	0.5196 (2)	0.1541 (2)	0.052 (3)
C110	0.8688 (2)	0.5565 (2)	0.2277 (2)	0.043 (2)
C111	0.8497 (2)	0.5217 (2)	0.2964 (2)	0.048 (3)
C112	0.7817 (2)	0.4587 (2)	0.2754 (2)	0.053 (3)
C113	0.7594 (2)	0.4561 (2)	0.1927 (2)	0.055 (3)
C114	0.8625 (2)	0.4777 (2)	0.0967 (2)	0.060 (3)
C115	0.9264 (2)	0.4103 (3)	0.1320 (2)	0.066 (3)
C116	0.9696 (3)	0.3681 (3)	0.0709 (2)	0.081 (3)
C117	1.0327 (3)	0.3001 (3)	0.1046 (3)	0.085 (4)
C118	1.0777 (3)	0.2595 (4)	0.0442 (4)	0.141 (5)
C119	1.1389 (4)	0.1908 (4)	0.0761 (4)	0.182 (6)
C120	0.7540 (2)	0.5889 (2)	0.1084 (2)	0.056 (3)
C121	0.7009 (2)	0.6403 (2)	0.1559 (2)	0.058 (3)
C122	0.6412 (2)	0.7020 (2)	0.1045 (2)	0.060 (3)
C123	0.5864 (2)	0.7537 (3)	0.1505 (2)	0.064 (3)
C124	0.5255 (3)	0.8126 (3)	0.0971 (2)	0.074 (3)
C125	0.4681 (3)	0.8653 (3)	0.1395 (3)	0.090 (4)
C201	1.0636 (2)	0.7474 (2)	0.2393 (2)	0.043 (2)
C202	1.0427 (2)	0.7119 (2)	0.3077 (2)	0.039 (2)
C203	1.0876 (2)	0.7406 (3)	0.3803 (2)	0.056 (3)
C204	1.1498 (2)	0.8025 (3)	0.3856 (2)	0.059 (3)
C205	1.2869 (3)	0.9496 (3)	0.3571 (2)	0.063 (3)
C206	1.3379 (3)	1.0087 (3)	0.3277 (3)	0.075 (3)
C207	1.3315 (3)	1.0207 (3)	0.2475 (3)	0.078 (3)
C208	1.2740 (3)	0.9735 (3)	0.1938 (2)	0.068 (3)
C209	1.1565 (2)	0.8549 (2)	0.1770 (2)	0.047 (2)
C210	1.1256 (2)	0.8093 (2)	0.2443 (2)	0.041 (2)
C211	1.1697 (2)	0.8371 (2)	0.3179 (2)	0.043 (2)
C212	1.2297 (2)	0.9021 (2)	0.3040 (2)	0.047 (2)
C213	1.2234 (2)	0.9138 (2)	0.2224 (2)	0.049 (3)
C214	1.1952 (2)	0.7932 (2)	0.1232 (2)	0.053 (3)
C215	1.2644 (2)	0.7332 (2)	0.1650 (2)	0.053 (3)
C216	1.3009 (2)	0.6805 (2)	0.1049 (2)	0.060 (3)
C217	1.3702 (2)	0.6192 (2)	0.1420 (2)	0.056 (3)
C218	1.4068 (3)	0.5693 (3)	0.0802 (2)	0.072 (3)
C219	1.4774 (3)	0.5078 (3)	0.1138 (2)	0.083 (3)
C220	1.0839 (2)	0.9047 (2)	0.1239 (2)	0.052 (2)
C221	1.0350 (2)	0.9665 (2)	0.1669 (2)	0.057 (3)
C222	0.9635 (2)	1.0094 (2)	0.1100 (2)	0.061 (3)
C223	0.9139 (2)	1.0744 (2)	0.1483 (2)	0.060 (3)
C224	0.8460 (3)	1.1181 (3)	0.0877 (2)	0.082 (3)
C225	0.7951 (3)	1.1856 (3)	0.1210 (2)	0.087 (3)
H101	0.94291	0.64153	0.17980	0.08000*
H103	0.98709	0.62909	0.42494	0.08000*
H104	0.88040	0.52340	0.41924	0.08000*
H105	0.75652	0.40843	0.38127	0.08000*
H106	0.64584	0.31705	0.31797	0.08000*
H107	0.61057	0.30909	0.17800	0.08000*
H108	0.68017	0.39934	0.09712	0.08000*
H114a	0.82110	0.45111	0.05313	0.08000*
H114b	0.89427	0.52394	0.07497	0.08000*
H115a	0.97089	0.43791	0.17246	0.08000*
H115b	0.89584	0.36631	0.15749	0.08000*
H116a	0.92480	0.34151	0.02960	0.08000*
H116b	1.00041	0.41251	0.04528	0.08000*
H117a	1.07717	0.32580	0.14669	0.08000*
H117b	1.00228	0.25428	0.12815	0.08000*
H118a	1.03356	0.23619	−0.00105	0.08000*
H118b	1.11019	0.30565	0.01970	0.08000*
H120a	0.79218	0.62928	0.08651	0.08000*
H120b	0.71455	0.56114	0.06411	0.08000*
H121a	0.66614	0.60017	0.18196	0.08000*
H121b	0.74003	0.67293	0.19720	0.08000*
H122a	0.67663	0.74195	0.07928	0.08000*
H122b	0.60315	0.66882	0.06311	0.08000*
H123a	0.55228	0.71354	0.17730	0.08000*
H123b	0.62444	0.78805	0.19102	0.08000*
H124a	0.56043	0.85266	0.07077	0.08000*
H124b	0.48881	0.77767	0.05593	0.08000*
H119a	1.18318	0.21438	0.11894	0.08000*
H119b	1.10655	0.14493	0.09819	0.08000*
H119c	1.16836	0.16418	0.03476	0.08000*
H125a	0.43324	0.82528	0.16592	0.08000*
H125b	0.50485	0.90027	0.18076	0.08000*
H125c	0.42816	0.90408	0.10476	0.08000*
H201	1.03355	0.72787	0.18600	0.08000*
H203	1.07449	0.71613	0.43065	0.08000*
H204	1.18019	0.82218	0.43901	0.08000*
H205	1.29195	0.94171	0.41565	0.08000*
H206	1.37929	1.04291	0.36581	0.08000*
H207	1.36853	1.06400	0.22757	0.08000*
H208	1.26889	0.98217	0.13495	0.08000*
H214a	1.14728	0.75792	0.09410	0.08000*
H214b	1.21989	0.82803	0.08436	0.08000*
H215a	1.31065	0.76759	0.19712	0.08000*
H215b	1.23887	0.69468	0.20065	0.08000*
H216a	1.25350	0.64728	0.07292	0.08000*
H216b	1.32538	0.72013	0.06950	0.08000*
H217a	1.41720	0.65187	0.17476	0.08000*
H217b	1.34560	0.57822	0.17590	0.08000*
H218a	1.36004	0.53574	0.04757	0.08000*
H218b	1.43067	0.61011	0.04537	0.08000*
H220a	1.10949	0.93761	0.08432	0.08000*
H220b	1.04244	0.86251	0.09582	0.08000*
H221a	1.01037	0.93469	0.20774	0.08000*
H221b	1.07529	1.01066	0.19327	0.08000*
H222a	0.98901	1.03830	0.06797	0.08000*
H222b	0.92318	0.96434	0.08514	0.08000*
H223a	0.88521	1.04527	0.18786	0.08000*
H223b	0.95395	1.11823	0.17502	0.08000*
H224a	0.87488	1.14543	0.04674	0.08000*
H224b	0.80549	1.07384	0.06126	0.08000*
H219a	1.52486	0.54194	0.14708	0.08300*
H219b	1.45446	0.46754	0.15016	0.08300*
H219c	1.49761	0.47845	0.07112	0.08300*
H225a	0.76634	1.15764	0.16095	0.08000*
H225b	0.83573	1.22923	0.14643	0.08000*
H225c	0.75077	1.21370	0.08053	0.08000*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C101	0.046 (2)	0.050 (3)	0.043 (2)	−0.002 (2)	0.009 (2)	0.004 (2)
C102	0.042 (2)	0.039 (2)	0.047 (2)	−0.001 (2)	0.008 (2)	−0.001 (2)
C103	0.066 (3)	0.063 (3)	0.038 (2)	−0.015 (2)	0.002 (2)	−0.003 (2)
C104	0.067 (3)	0.065 (3)	0.052 (3)	−0.021 (2)	0.015 (2)	0.001 (2)
C105	0.063 (3)	0.054 (3)	0.077 (3)	−0.002 (3)	0.016 (3)	0.009 (3)
C106	0.074 (4)	0.054 (3)	0.112 (4)	−0.005 (3)	0.033 (3)	0.014 (3)
C107	0.059 (3)	0.056 (3)	0.124 (4)	−0.025 (3)	0.017 (3)	0.005 (3)
C108	0.062 (3)	0.058 (3)	0.088 (3)	−0.015 (3)	−0.002 (3)	0.000 (3)
C109	0.049 (3)	0.056 (3)	0.050 (3)	−0.015 (2)	0.006 (2)	0.004 (2)
C110	0.047 (3)	0.038 (2)	0.045 (3)	−0.005 (2)	0.012 (2)	0.005 (2)
C111	0.043 (3)	0.043 (3)	0.058 (3)	−0.007 (2)	0.013 (2)	0.002 (2)
C112	0.046 (3)	0.044 (3)	0.070 (3)	−0.003 (2)	0.016 (2)	0.007 (2)
C113	0.048 (3)	0.046 (3)	0.070 (3)	−0.001 (2)	0.010 (2)	0.004 (2)
C114	0.063 (3)	0.061 (3)	0.053 (3)	−0.010 (2)	0.004 (2)	−0.014 (2)
C115	0.062 (3)	0.062 (3)	0.073 (3)	−0.006 (2)	0.012 (2)	−0.007 (3)
C116	0.074 (3)	0.080 (4)	0.087 (4)	−0.014 (3)	0.011 (3)	−0.028 (3)
C117	0.063 (3)	0.070 (4)	0.127 (4)	−0.004 (3)	0.027 (3)	−0.020 (3)
C118	0.093 (5)	0.123 (6)	0.208 (7)	−0.007 (4)	0.027 (4)	−0.084 (5)
C119	0.107 (5)	0.122 (6)	0.332 (9)	−0.028 (4)	0.080 (5)	−0.111 (6)
C120	0.059 (3)	0.060 (3)	0.046 (2)	−0.012 (2)	0.000 (2)	−0.001 (2)
C121	0.053 (3)	0.061 (3)	0.058 (3)	−0.006 (2)	0.006 (2)	0.009 (2)
C122	0.061 (3)	0.061 (3)	0.056 (3)	0.000 (2)	0.003 (2)	0.001 (2)
C123	0.061 (3)	0.072 (3)	0.058 (3)	−0.007 (3)	0.009 (2)	0.007 (2)
C124	0.067 (3)	0.083 (4)	0.070 (3)	0.007 (3)	0.007 (2)	0.003 (3)
C125	0.077 (4)	0.081 (4)	0.116 (4)	0.005 (3)	0.026 (3)	0.001 (3)
C201	0.043 (2)	0.046 (3)	0.038 (2)	−0.006 (2)	0.003 (2)	−0.003 (2)
C202	0.041 (2)	0.035 (2)	0.041 (2)	0.001 (2)	0.004 (2)	−0.000 (2)
C203	0.065 (3)	0.062 (3)	0.040 (3)	−0.013 (2)	0.007 (2)	0.002 (2)
C204	0.062 (3)	0.073 (3)	0.037 (2)	−0.017 (2)	−0.000 (2)	−0.004 (2)
C205	0.060 (3)	0.055 (3)	0.072 (3)	−0.008 (2)	0.005 (2)	−0.007 (2)
C206	0.054 (3)	0.058 (3)	0.106 (4)	−0.004 (3)	−0.005 (3)	−0.024 (3)
C207	0.062 (3)	0.049 (3)	0.125 (4)	−0.016 (3)	0.023 (3)	−0.008 (3)
C208	0.074 (3)	0.064 (3)	0.070 (3)	−0.016 (3)	0.020 (3)	−0.001 (3)
C209	0.053 (3)	0.048 (3)	0.042 (2)	−0.007 (2)	0.010 (2)	−0.003 (2)
C210	0.041 (2)	0.041 (3)	0.041 (2)	0.003 (2)	0.007 (2)	−0.002 (2)
C211	0.037 (2)	0.045 (3)	0.047 (3)	0.003 (2)	0.004 (2)	−0.004 (2)
C212	0.038 (2)	0.043 (3)	0.059 (3)	−0.001 (2)	0.007 (2)	−0.007 (2)
C213	0.044 (3)	0.046 (3)	0.059 (3)	0.001 (2)	0.011 (2)	−0.001 (2)
C214	0.053 (3)	0.050 (3)	0.054 (3)	−0.003 (2)	0.009 (2)	0.001 (2)
C215	0.057 (3)	0.055 (3)	0.050 (3)	0.001 (2)	0.014 (2)	0.001 (2)
C216	0.056 (3)	0.058 (3)	0.064 (3)	−0.000 (2)	0.008 (2)	−0.004 (2)
C217	0.053 (3)	0.057 (3)	0.059 (3)	−0.006 (2)	0.008 (2)	−0.007 (2)
C218	0.073 (3)	0.075 (4)	0.069 (3)	0.010 (3)	0.014 (2)	−0.008 (3)
C219	0.087 (4)	0.085 (4)	0.078 (3)	0.015 (3)	0.019 (3)	−0.000 (3)
C220	0.058 (3)	0.049 (3)	0.048 (2)	0.003 (2)	0.007 (2)	0.005 (2)
C221	0.060 (3)	0.055 (3)	0.054 (3)	0.008 (2)	0.008 (2)	0.003 (2)
C222	0.066 (3)	0.065 (3)	0.053 (3)	0.006 (2)	0.008 (2)	0.004 (2)
C223	0.068 (3)	0.061 (3)	0.053 (3)	0.006 (2)	0.015 (2)	0.005 (2)
C224	0.098 (4)	0.079 (4)	0.069 (3)	0.029 (3)	0.015 (3)	0.006 (3)
C225	0.092 (4)	0.081 (4)	0.090 (4)	0.018 (3)	0.021 (3)	0.020 (3)

Geometric parameters (Å, º)

C101—C102	1.409 (5)	C201—C202	1.394 (5)
C101—C110	1.374 (5)	C201—C210	1.383 (5)
C101—H101	0.993 (4)	C201—H201	1.000 (3)
C102—C103	1.402 (5)	C202—C203	1.393 (5)
C102—C202	1.472 (5)	C203—C204	1.385 (6)
C103—C104	1.382 (6)	C203—H203	1.002 (4)
C103—H103	1.005 (3)	C204—C211	1.371 (5)
C104—C111	1.375 (5)	C204—H204	1.004 (3)
C104—H104	1.003 (4)	C205—C206	1.391 (6)
C105—C106	1.392 (6)	C205—C212	1.386 (5)
C105—C112	1.388 (6)	C205—H205	1.000 (4)
C105—H105	1.000 (4)	C206—C207	1.373 (7)
C106—C107	1.374 (7)	C206—H206	0.999 (4)
C106—H106	1.002 (5)	C207—C208	1.391 (6)
C107—C108	1.379 (7)	C207—H207	1.003 (5)
C107—H107	0.998 (4)	C208—C213	1.387 (6)
C108—C113	1.389 (5)	C208—H208	1.007 (4)
C108—H108	1.006 (4)	C209—C210	1.515 (5)
C109—C110	1.534 (5)	C209—C213	1.520 (5)
C109—C113	1.525 (6)	C209—C214	1.546 (5)
C109—C114	1.539 (6)	C209—C220	1.551 (5)
C109—C120	1.544 (5)	C210—C211	1.399 (5)
C110—C111	1.383 (5)	C211—C212	1.453 (5)
C111—C112	1.468 (5)	C212—C213	1.395 (5)
C112—C113	1.398 (6)	C214—C215	1.530 (5)
C114—C115	1.522 (5)	C214—H214a	1.003 (3)
C114—H114a	0.996 (3)	C214—H214b	0.998 (4)
C114—H114b	0.999 (4)	C215—C216	1.521 (5)
C115—C116	1.510 (6)	C215—H215a	0.997 (3)
C115—H115a	0.998 (4)	C215—H215b	1.000 (4)
C115—H115b	0.994 (4)	C216—C217	1.518 (5)
C116—C117	1.513 (6)	C216—H216a	0.999 (4)
C116—H116a	1.002 (4)	C216—H216b	1.000 (4)
C116—H116b	1.002 (5)	C217—C218	1.519 (6)
C117—C118	1.508 (8)	C217—H217a	0.996 (3)
C117—H117a	1.001 (4)	C217—H217b	0.996 (4)
C117—H117b	0.996 (5)	C218—C219	1.520 (6)
C118—C119	1.495 (8)	C218—H218a	0.999 (4)
C118—H118a	1.016 (6)	C218—H218b	1.000 (4)
C118—H118b	1.027 (6)	C219—H219a	1.016 (4)
C119—H119a	0.994 (6)	C219—H219b	1.005 (4)
C119—H119b	1.002 (7)	C219—H219c	0.969 (4)
C119—H119c	1.011 (7)	C220—C221	1.520 (5)
C120—C121	1.513 (6)	C220—H220a	1.000 (4)
C120—H120a	1.002 (4)	C220—H220b	0.998 (3)
C120—H120b	0.995 (3)	C221—C222	1.520 (5)
C121—C122	1.526 (5)	C221—H221a	0.999 (4)
C121—H121a	1.000 (4)	C221—H221b	0.999 (4)
C121—H121b	0.998 (3)	C222—C223	1.517 (6)
C122—C123	1.518 (6)	C222—H222a	1.000 (4)
C122—H122a	0.997 (4)	C222—H222b	1.000 (4)
C122—H122b	0.994 (3)	C223—C224	1.523 (5)
C123—C124	1.524 (5)	C223—H223a	0.998 (4)
C123—H123a	1.001 (4)	C223—H223b	0.995 (4)
C123—H123b	0.996 (4)	C224—C225	1.512 (6)
C124—C125	1.517 (6)	C224—H224a	1.005 (4)
C124—H124a	1.002 (4)	C224—H224b	1.003 (4)
C124—H124b	0.997 (4)	C225—H225a	0.995 (4)
C125—H125a	1.004 (4)	C225—H225b	0.991 (4)
C125—H125b	0.999 (4)	C225—H225c	1.000 (4)
C125—H125c	0.999 (4)
C102—C101—C110	120.4 (3)	C202—C201—C210	120.7 (3)
C102—C101—H101	119.8 (3)	C202—C201—H201	119.8 (3)
C110—C101—H101	119.8 (3)	C210—C201—H201	119.5 (3)
C101—C102—C103	116.7 (3)	C102—C202—C201	121.3 (3)
C101—C102—C202	121.6 (3)	C102—C202—C203	121.5 (3)
C103—C102—C202	121.7 (3)	C201—C202—C203	117.2 (3)
C102—C103—C104	122.6 (3)	C202—C203—C204	122.3 (3)
C102—C103—H103	118.4 (4)	C202—C203—H203	119.3 (4)
C104—C103—H103	119.0 (4)	C204—C203—H203	118.4 (3)
C103—C104—C111	119.2 (4)	C203—C204—C211	120.0 (3)
C103—C104—H104	120.2 (3)	C203—C204—H204	119.9 (4)
C111—C104—H104	120.6 (4)	C211—C204—H204	120.1 (4)
C106—C105—C112	118.3 (4)	C206—C205—C212	118.9 (4)
C106—C105—H105	120.8 (4)	C206—C205—H205	120.1 (4)
C112—C105—H105	120.8 (4)	C212—C205—H205	121.0 (4)
C105—C106—C107	121.4 (4)	C205—C206—C207	120.9 (4)
C105—C106—H106	118.5 (5)	C205—C206—H206	119.1 (5)
C107—C106—H106	120.1 (4)	C207—C206—H206	119.9 (4)
C106—C107—C108	120.4 (4)	C206—C207—C208	120.5 (4)
C106—C107—H107	119.3 (5)	C206—C207—H207	119.6 (4)
C108—C107—H107	120.3 (5)	C208—C207—H207	119.9 (5)
C107—C108—C113	119.4 (4)	C207—C208—C213	119.1 (4)
C107—C108—H108	120.8 (4)	C207—C208—H208	120.9 (4)
C113—C108—H108	119.8 (4)	C213—C208—H208	120.0 (4)
C110—C109—C113	100.6 (3)	C210—C209—C213	101.4 (3)
C110—C109—C114	112.3 (3)	C210—C209—C214	112.1 (3)
C110—C109—C120	111.0 (3)	C210—C209—C220	112.0 (3)
C113—C109—C114	112.9 (3)	C213—C209—C214	111.7 (3)
C113—C109—C120	111.6 (3)	C213—C209—C220	111.8 (3)
C114—C109—C120	108.3 (3)	C214—C209—C220	107.8 (3)
C101—C110—C109	127.6 (3)	C201—C210—C209	128.1 (3)
C101—C110—C111	121.4 (3)	C201—C210—C211	121.0 (3)
C109—C110—C111	110.9 (3)	C209—C210—C211	110.9 (3)
C104—C111—C110	119.7 (3)	C204—C211—C210	118.8 (3)
C104—C111—C112	131.1 (4)	C204—C211—C212	133.0 (3)
C110—C111—C112	109.2 (3)	C210—C211—C212	108.2 (3)
C105—C112—C111	131.6 (4)	C205—C212—C211	130.5 (4)
C105—C112—C113	120.5 (3)	C205—C212—C213	120.4 (4)
C111—C112—C113	108.0 (4)	C211—C212—C213	109.2 (3)
C108—C113—C109	128.7 (4)	C208—C213—C209	129.5 (3)
C108—C113—C112	120.0 (4)	C208—C213—C212	120.2 (3)
C109—C113—C112	111.3 (3)	C209—C213—C212	110.3 (3)
C109—C114—C115	116.3 (3)	C209—C214—C215	116.3 (3)
C109—C114—H114a	107.6 (3)	C209—C214—H214a	107.1 (3)
C109—C114—H114b	107.0 (3)	C209—C214—H214b	107.6 (3)
C115—C114—H114a	108.0 (3)	C215—C214—H214a	108.1 (3)
C115—C114—H114b	108.0 (3)	C215—C214—H214b	108.3 (3)
H114a—C114—H114b	109.9 (3)	H214a—C214—H214b	109.4 (3)
C114—C115—C116	113.0 (3)	C214—C215—C216	110.8 (3)
C114—C115—H115a	108.2 (4)	C214—C215—H215a	108.8 (3)
C114—C115—H115b	108.3 (3)	C214—C215—H215b	108.8 (3)
C116—C115—H115a	108.5 (4)	C216—C215—H215a	109.5 (3)
C116—C115—H115b	108.7 (4)	C216—C215—H215b	109.3 (3)
H115a—C115—H115b	110.2 (4)	H215a—C215—H215b	109.7 (3)
C115—C116—C117	113.8 (3)	C215—C216—C217	113.9 (3)
C115—C116—H116a	108.5 (4)	C215—C216—H216a	108.2 (3)
C115—C116—H116b	108.7 (4)	C215—C216—H216b	108.0 (3)
C117—C116—H116a	108.2 (4)	C217—C216—H216a	108.6 (3)
C117—C116—H116b	108.5 (4)	C217—C216—H216b	108.5 (3)
H116a—C116—H116b	109.2 (4)	H216a—C216—H216b	109.6 (3)
C116—C117—C118	114.0 (4)	C216—C217—C218	112.4 (3)
C116—C117—H117a	108.9 (4)	C216—C217—H217a	108.9 (3)
C116—C117—H117b	109.2 (4)	C216—C217—H217b	108.8 (3)
C118—C117—H117a	107.6 (4)	C218—C217—H217a	108.3 (3)
C118—C117—H117b	107.4 (4)	C218—C217—H217b	108.3 (3)
H117a—C117—H117b	109.7 (4)	H217a—C217—H217b	110.1 (3)
C117—C118—C119	114.7 (5)	C217—C218—C219	114.8 (3)
C117—C118—H118a	109.1 (5)	C217—C218—H218a	108.8 (4)
C117—C118—H118b	108.6 (5)	C217—C218—H218b	108.7 (4)
C119—C118—H118a	109.5 (5)	C219—C218—H218a	107.5 (4)
C119—C118—H118b	108.5 (5)	C219—C218—H218b	107.4 (4)
H118a—C118—H118b	106.1 (6)	H218a—C218—H218b	109.5 (3)
C118—C119—H119a	109.2 (5)	C218—C219—H219a	107.5 (4)
C118—C119—H119b	108.3 (5)	C218—C219—H219b	108.0 (4)
C118—C119—H119c	113.6 (6)	C218—C219—H219c	110.2 (3)
H119a—C119—H119b	109.7 (7)	H219a—C219—H219b	107.8 (3)
H119a—C119—H119c	108.3 (6)	H219a—C219—H219c	111.1 (4)
H119b—C119—H119c	107.6 (6)	H219b—C219—H219c	112.1 (4)
C109—C120—C121	116.4 (3)	C209—C220—C221	115.8 (3)
C109—C120—H120a	107.2 (3)	C209—C220—H220a	107.9 (3)
C109—C120—H120b	108.0 (3)	C209—C220—H220b	107.8 (3)
C121—C120—H120a	107.5 (3)	C221—C220—H220a	107.8 (3)
C121—C120—H120b	107.9 (3)	C221—C220—H220b	107.9 (3)
H120a—C120—H120b	109.8 (3)	H220a—C220—H220b	109.7 (3)
C120—C121—C122	112.6 (3)	C220—C221—C222	111.5 (3)
C120—C121—H121a	108.3 (3)	C220—C221—H221a	108.7 (3)
C120—C121—H121b	108.6 (3)	C220—C221—H221b	108.8 (3)
C122—C121—H121a	108.7 (3)	C222—C221—H221a	109.1 (3)
C122—C121—H121b	109.0 (3)	C222—C221—H221b	109.0 (3)
H121a—C121—H121b	109.7 (3)	H221a—C221—H221b	109.7 (3)
C121—C122—C123	113.7 (3)	C221—C222—C223	114.4 (3)
C121—C122—H122a	108.0 (3)	C221—C222—H222a	107.9 (3)
C121—C122—H122b	108.2 (3)	C221—C222—H222b	107.9 (3)
C123—C122—H122a	108.2 (3)	C223—C222—H222a	108.5 (3)
C123—C122—H122b	108.6 (3)	C223—C222—H222b	108.6 (3)
H122a—C122—H122b	110.1 (3)	H222a—C222—H222b	109.5 (3)
C122—C123—C124	112.4 (3)	C222—C223—C224	112.0 (3)
C122—C123—H123a	108.2 (4)	C222—C223—H223a	108.9 (3)
C122—C123—H123b	108.6 (3)	C222—C223—H223b	109.1 (3)
C124—C123—H123a	108.7 (3)	C224—C223—H223a	108.2 (3)
C124—C123—H123b	109.2 (4)	C224—C223—H223b	108.5 (3)
H123a—C123—H123b	109.8 (4)	H223a—C223—H223b	110.1 (3)
C123—C124—C125	114.9 (3)	C223—C224—C225	115.3 (3)
C123—C124—H124a	107.9 (3)	C223—C224—H224a	108.0 (4)
C123—C124—H124b	108.4 (4)	C223—C224—H224b	108.3 (4)
C125—C124—H124a	107.7 (4)	C225—C224—H224a	108.0 (4)
C125—C124—H124b	108.2 (4)	C225—C224—H224b	108.3 (4)
H124a—C124—H124b	109.5 (4)	H224a—C224—H224b	108.8 (4)
C124—C125—H125a	107.8 (4)	C224—C225—H225a	107.2 (4)
C124—C125—H125b	108.3 (4)	C224—C225—H225b	107.5 (4)
C124—C125—H125c	115.3 (4)	C224—C225—H225c	114.4 (4)
H125a—C125—H125b	109.2 (4)	H225a—C225—H225b	110.6 (4)
H125a—C125—H125c	107.9 (4)	H225a—C225—H225c	108.5 (4)
H125b—C125—H125c	108.2 (4)	H225b—C225—H225c	108.7 (4)