5,11-Bis(4-tert-butylphen­yl)-6,12-diphenyl­naphthacene (form A)

The title compound, C₅₀H₄₄, is a derivative of rubrene where tert-butyl side groups are added to two of the pendant aromatic rings. Two polymorphs of this derivative, the title compound (form A) and form B, have been identified. The mol­ecule of form A displays a strongly twisted naphthacene backbone. The in-plane arrangement differs from the classical herringbone structure, resembling a slip–stack structure type with the backbones separated by a minimum 7.0 Å in the direction of possible π-stacking.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.098
• wR factor = 0.169
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       6.23 Ratio

Author Response: The atom diaplacement parameters of the C atoms in the tert-butyl group is larger than usual, suggesting positional disorder.

PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C36

Author Response: The atom diaplacement parameters of C36 and C46 is small as compared with extremely large atom displacement parameters of the C atoms in the tert-butyl groups.

PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C46

Author Response: The atom diaplacement parameters of C36 and C46 is small as compared with extremely large atom displacement parameters of the C atoms in the tert-butyl groups.

Alert level B
PLAT213_ALERT_2_B Atom C37     has ADP max/min Ratio .............       4.20 prola
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.25 Ratio

Author Response: The atom diaplacement parameters of the H atoms in the tert-butyl group is larger than usual, suggesting positional disorder.

Alert level C
PLAT213_ALERT_2_C Atom C39     has ADP max/min Ratio .............       3.70 prola
PLAT213_ALERT_2_C Atom C47     has ADP max/min Ratio .............       3.20 prola
PLAT245_ALERT_2_C U(iso) H23     Smaller than U(eq) C23     by ...       0.02 AngSq
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

   3 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The electronic properties of rubrene and rubrene derivatives are of great interest owing to fundamental questions on charge transport and associated applications (Sundar et al., 2004; Goldmann et al., 2004). The electric transport properties of the two polymorphs of the title compound are distinctly different: in polymorph B, the in-plane hole is as high as 12 cm²/Vs, on par with rubrene, which is known to be the organic semiconductor with the highest hole mobility. In contrast, the title compound, (I), polymorph A is highly resistive and does not show any field-induced electrical transport (Haas et al., 2007, Strassen et al., 2007).

The crystal structure of (I) is monoclinic, with space group P2₁/c, with four molecules in the unit cell (Fig. 1). The molecules form a layered structure, similar to linear acenes such as pentacene (Mattheus et al., 2001) with the naphthacene backbone standing upright (see Fig. 2). A particular characteristic of polymorph A is the twist of the naphthalene backbone by 43° (defined as the torsion angle between the two terminal C—C bonds [C1—C2 and C17—C18] at the ends of the backbone).

Polymorph B exclusively grows in the form of ultrathin platelets (Haas et al., 2007). From d-spacing measurements on these samples, a structure closely related to the one found for a constitutional isomer, 5,12-bis-(4-tert-butyl-phenyl)-6,11-diphenyl-naphthacene (Schuck et al., 2007) was assumed for polymorph B. A complete structure determination of form B, however, has not been feasible so far due to the crystal morphology.

Related literature

For related literature, see: Goldmann et al. (2004); Haas et al. (2007); Kloc et al. (1997); Kopranenkov & Luk'yanets (1972); Mattheus et al. (2001); Schuck et al. (2007); Sundar et al. (2004).

For related literature, see: Laudize et al. (1998); Strassen (2007).

S2. Experimental

The title compound was synthesized according to the method of Kopranenkov & Luk'yanets (1972). Physical vapour transport (Kloc et al., 1997, Laudize et al., 1998) at 533 K, using high purity argon as the transport gas made single crystals of both polymorphs at the same time. The morphology (plates typically 0.1–0.2 µm thick), orange colour and transparency of both forms are basically the same. The two forms can only be distinguished by measuring their d-spacings perpendicular to the crystal platelets (form A: d₁₀₀ = 23.4 Å and form B d = 35.1 Å) (Haas et al., 2007).

Only at a slightly higher temperature (and with longer growth time), a few thicker crystals of form A could be grown for full structural characterization with XRD.

S3. Refinement

The H atoms in the aromatic units were located in difference maps and their positions were freely refined with U_iso(H) = 1.2U_eq(carrier). The H atoms of the methyl groups were positioned geometrically (C—H = 0.96 Å) and were refined as riding on the parent C atoms with U_iso(H) = 1.5U_eq(carrier).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of (I), showing the atom numbering scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).
	Fig. 2. The crystal packing for (I), viewed (a) down the a axis and (b) viewed down the b axis.

5,11-Bis(4-tert-butyl-phenyl)-6,12-diphenylnaphthacene

Crystal data

C50H44	F(000) = 1376
Mr = 644.85	Dx = 1.141 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3136 reflections
a = 23.527 (3) Å	θ = 3.0–25.0°
b = 9.0277 (10) Å	µ = 0.06 mm^−1
c = 17.764 (2) Å	T = 292 K
β = 95.928 (4)°	Plate, translucent orange
V = 3752.8 (8) Å^3	0.36 × 0.16 × 0.04 mm
Z = 4

Data collection

Brucker SMART CCD diffractometer	6626 independent reflections
Radiation source: fine-focus sealed tube	3478 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
φ and ω scans	θmax = 25.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −27→27
Tmin = 0.990, Tmax = 0.997	k = −10→10
31129 measured reflections	l = −21→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F^2 > 2σ(F^2)] = 0.098	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.169	w = 1/[σ^2(Fo^2) + (0.0241P)^2 + 4.9951P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.004
6626 reflections	Δρmax = 0.29 e Å^−3
536 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (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	0.4082 (2)	0.7231 (5)	0.3755 (3)	0.0571 (13)
C2	0.43973 (19)	0.6785 (5)	0.4434 (3)	0.0544 (13)
C3	0.35092 (18)	0.7072 (5)	0.3654 (2)	0.0444 (11)
C4	0.41355 (18)	0.6099 (5)	0.4982 (3)	0.0481 (12)
C5	0.32005 (16)	0.6423 (4)	0.4231 (2)	0.0388 (10)
C6	0.35296 (15)	0.5814 (4)	0.4884 (2)	0.0352 (10)
C7	0.26002 (16)	0.6412 (4)	0.4184 (2)	0.0378 (10)
C8	0.32605 (15)	0.4935 (4)	0.5393 (2)	0.0356 (10)
C9	0.23227 (15)	0.5692 (4)	0.4762 (2)	0.0350 (10)
C10	0.26556 (15)	0.4713 (4)	0.5276 (2)	0.0357 (10)
C11	0.17319 (15)	0.5862 (4)	0.4856 (2)	0.0353 (10)
C12	0.23732 (16)	0.3584 (4)	0.5653 (2)	0.0370 (10)
C13	0.14684 (15)	0.4909 (4)	0.5329 (2)	0.0360 (10)
C14	0.17806 (16)	0.3674 (4)	0.5681 (2)	0.0387 (10)
C15	0.08776 (17)	0.5078 (5)	0.5463 (2)	0.0464 (11)
C16	0.14702 (19)	0.2603 (5)	0.6065 (3)	0.0512 (12)
C17	0.0615 (2)	0.4075 (6)	0.5867 (3)	0.0550 (13)
C18	0.0911 (2)	0.2800 (6)	0.6153 (3)	0.0604 (14)
C20	0.22674 (17)	0.6982 (5)	0.3482 (2)	0.0483 (11)
C21	0.2261 (2)	0.8465 (6)	0.3280 (3)	0.0723 (16)
C22	0.1970 (3)	0.8925 (10)	0.2595 (5)	0.106 (3)
C23	0.1690 (3)	0.7895 (13)	0.2123 (4)	0.120 (4)
C24	0.1700 (3)	0.6451 (11)	0.2308 (3)	0.105 (3)
C25	0.1988 (2)	0.5961 (7)	0.2987 (3)	0.0669 (15)
C30	0.35873 (15)	0.4391 (4)	0.6107 (2)	0.0375 (10)
C31	0.40131 (16)	0.3323 (5)	0.6126 (2)	0.0444 (11)
C32	0.42905 (18)	0.2851 (5)	0.6807 (3)	0.0487 (12)
C33	0.41595 (18)	0.3416 (5)	0.7495 (2)	0.0488 (11)
C34	0.3746 (2)	0.4500 (5)	0.7468 (2)	0.0519 (12)
C35	0.34595 (19)	0.4986 (5)	0.6788 (2)	0.0486 (12)
C36	0.4456 (2)	0.2853 (6)	0.8254 (3)	0.0669 (14)
C37	0.4903 (4)	0.3883 (8)	0.8554 (4)	0.202 (5)
H37A	0.5054	0.3571	0.9052	0.303*
H37B	0.4745	0.4860	0.8580	0.303*
H37C	0.5204	0.3893	0.8228	0.303*
C38	0.4708 (3)	0.1331 (7)	0.8175 (3)	0.146 (3)
H38A	0.5047	0.1407	0.7920	0.219*
H38B	0.4435	0.0710	0.7886	0.219*
H38C	0.4802	0.0908	0.8667	0.219*
C39	0.4024 (4)	0.2652 (12)	0.8809 (4)	0.218 (6)
H39A	0.4184	0.2046	0.9222	0.327*
H39B	0.3689	0.2180	0.8563	0.327*
H39C	0.3922	0.3601	0.8999	0.327*
C40	0.14101 (16)	0.7183 (4)	0.4525 (2)	0.0371 (10)
C41	0.15368 (19)	0.8579 (5)	0.4817 (2)	0.0491 (12)
C42	0.1243 (2)	0.9821 (5)	0.4531 (3)	0.0579 (13)
C43	0.08086 (18)	0.9718 (5)	0.3945 (2)	0.0446 (11)
C44	0.06779 (18)	0.8326 (5)	0.3667 (2)	0.0490 (12)
C45	0.09662 (17)	0.7067 (5)	0.3952 (2)	0.0437 (11)
C46	0.0491 (2)	1.1098 (5)	0.3632 (3)	0.0653 (14)
C47	0.0073 (3)	1.1571 (8)	0.4184 (4)	0.166 (4)
H47A	0.0282	1.1912	0.4645	0.249*
H47B	−0.0161	1.0743	0.4292	0.249*
H47C	−0.0164	1.2357	0.3965	0.249*
C48	0.0899 (3)	1.2343 (6)	0.3525 (4)	0.147 (3)
H48A	0.1074	1.2666	0.4009	0.220*
H48B	0.0695	1.3154	0.3273	0.220*
H48C	0.1190	1.2005	0.3223	0.220*
C49	0.0140 (3)	1.0800 (6)	0.2874 (3)	0.110 (2)
H49A	−0.0043	1.1698	0.2690	0.165*
H49B	−0.0145	1.0063	0.2941	0.165*
H49C	0.0388	1.0450	0.2515	0.165*
C50	0.26843 (17)	0.2211 (5)	0.5919 (3)	0.0473 (11)
C51	0.2768 (2)	0.1763 (6)	0.6668 (3)	0.0656 (15)
C52	0.3053 (2)	0.0437 (8)	0.6856 (4)	0.089 (2)
C53	0.3249 (3)	−0.0439 (7)	0.6305 (6)	0.103 (3)
C54	0.3169 (3)	−0.0008 (7)	0.5560 (5)	0.092 (2)
C55	0.2890 (2)	0.1303 (5)	0.5368 (3)	0.0639 (14)
H1	0.4291 (19)	0.759 (5)	0.335 (2)	0.077*
H2	0.4827 (19)	0.693 (5)	0.454 (2)	0.077*
H3	0.3284 (18)	0.744 (5)	0.317 (2)	0.077*
H4	0.4347 (18)	0.574 (5)	0.547 (2)	0.077*
H15	0.0685 (18)	0.600 (5)	0.524 (2)	0.077*
H16	0.1680 (18)	0.174 (5)	0.630 (2)	0.077*
H17	0.0193 (19)	0.428 (5)	0.596 (2)	0.077*
H18	0.0713 (19)	0.218 (5)	0.644 (2)	0.077*
H21	0.245 (2)	0.918 (6)	0.366 (3)	0.096*
H22	0.197 (2)	0.993 (6)	0.249 (3)	0.096*
H23	0.148 (2)	0.818 (6)	0.163 (3)	0.096*
H24	0.152 (2)	0.564 (6)	0.199 (3)	0.096*
H25	0.201 (2)	0.488 (6)	0.316 (3)	0.096*
H31	0.4121 (18)	0.287 (5)	0.565 (2)	0.077*
H32	0.4602 (19)	0.215 (5)	0.678 (2)	0.077*
H34	0.3639 (18)	0.496 (5)	0.793 (2)	0.077*
H35	0.3160 (18)	0.572 (5)	0.681 (2)	0.077*
H41	0.1844 (18)	0.866 (5)	0.523 (2)	0.077*
H42	0.1385 (18)	1.075 (5)	0.476 (2)	0.077*
H44	0.0400 (18)	0.817 (5)	0.325 (2)	0.077*
H45	0.0856 (18)	0.607 (5)	0.373 (2)	0.077*
H51	0.263 (2)	0.241 (6)	0.706 (3)	0.096*
H52	0.310 (2)	0.018 (6)	0.736 (3)	0.096*
H53	0.346 (2)	−0.140 (6)	0.646 (3)	0.096*
H54	0.329 (2)	−0.069 (6)	0.514 (3)	0.096*
H55	0.281 (2)	0.163 (5)	0.480 (3)	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.047 (3)	0.065 (3)	0.061 (3)	−0.008 (3)	0.018 (2)	0.010 (3)
C2	0.034 (3)	0.070 (3)	0.058 (3)	−0.011 (3)	0.000 (2)	0.009 (3)
C3	0.043 (3)	0.045 (3)	0.046 (3)	−0.002 (2)	0.009 (2)	0.008 (2)
C4	0.039 (3)	0.056 (3)	0.048 (3)	−0.004 (2)	−0.003 (2)	0.004 (2)
C5	0.039 (2)	0.034 (2)	0.043 (2)	−0.002 (2)	0.0004 (19)	0.0016 (19)
C6	0.028 (2)	0.035 (2)	0.042 (2)	−0.0030 (19)	0.0011 (18)	0.0019 (19)
C7	0.038 (2)	0.038 (2)	0.037 (2)	0.003 (2)	−0.0016 (18)	0.0045 (19)
C8	0.033 (2)	0.034 (2)	0.039 (2)	0.0025 (19)	0.0022 (18)	−0.0026 (19)
C9	0.032 (2)	0.036 (2)	0.036 (2)	0.0012 (19)	−0.0014 (18)	0.0010 (19)
C10	0.031 (2)	0.040 (2)	0.036 (2)	0.0034 (19)	0.0023 (17)	0.0007 (19)
C11	0.031 (2)	0.038 (2)	0.035 (2)	0.0015 (19)	−0.0029 (18)	0.0006 (19)
C12	0.035 (2)	0.040 (3)	0.037 (2)	0.004 (2)	0.0057 (18)	0.0036 (19)
C13	0.030 (2)	0.045 (3)	0.032 (2)	−0.001 (2)	0.0005 (17)	−0.005 (2)
C14	0.039 (2)	0.039 (3)	0.039 (2)	−0.004 (2)	0.0082 (19)	0.002 (2)
C15	0.038 (3)	0.057 (3)	0.045 (3)	−0.001 (2)	0.006 (2)	−0.001 (2)
C16	0.043 (3)	0.056 (3)	0.055 (3)	−0.005 (2)	0.004 (2)	0.008 (2)
C17	0.039 (3)	0.068 (3)	0.059 (3)	0.000 (3)	0.013 (2)	0.004 (3)
C18	0.049 (3)	0.072 (4)	0.063 (3)	−0.011 (3)	0.019 (2)	0.011 (3)
C20	0.041 (3)	0.065 (3)	0.041 (3)	0.010 (2)	0.010 (2)	0.012 (2)
C21	0.059 (3)	0.081 (4)	0.078 (4)	0.012 (3)	0.010 (3)	0.041 (3)
C22	0.079 (5)	0.127 (7)	0.115 (6)	0.033 (5)	0.028 (4)	0.076 (6)
C23	0.094 (6)	0.208 (11)	0.059 (5)	0.061 (7)	0.009 (4)	0.045 (6)
C24	0.088 (5)	0.168 (8)	0.053 (4)	0.050 (5)	−0.019 (3)	−0.023 (4)
C25	0.056 (3)	0.097 (4)	0.046 (3)	0.023 (3)	−0.003 (2)	−0.010 (3)
C30	0.027 (2)	0.043 (3)	0.043 (3)	−0.001 (2)	0.0014 (18)	0.004 (2)
C31	0.031 (2)	0.059 (3)	0.043 (3)	0.009 (2)	0.002 (2)	0.004 (2)
C32	0.037 (3)	0.056 (3)	0.053 (3)	0.010 (2)	0.004 (2)	0.011 (2)
C33	0.051 (3)	0.048 (3)	0.047 (3)	0.001 (2)	0.000 (2)	0.013 (2)
C34	0.065 (3)	0.050 (3)	0.040 (3)	0.008 (3)	0.006 (2)	−0.002 (2)
C35	0.053 (3)	0.046 (3)	0.046 (3)	0.010 (2)	0.002 (2)	0.001 (2)
C36	0.085 (4)	0.061 (3)	0.051 (3)	0.013 (3)	−0.010 (3)	0.016 (3)
C37	0.268 (10)	0.137 (7)	0.160 (7)	−0.100 (7)	−0.174 (8)	0.081 (6)
C38	0.226 (9)	0.095 (5)	0.100 (5)	0.050 (6)	−0.066 (5)	0.025 (4)
C39	0.200 (9)	0.369 (15)	0.095 (6)	0.109 (10)	0.062 (6)	0.141 (8)
C40	0.032 (2)	0.042 (3)	0.037 (2)	0.003 (2)	0.0034 (18)	−0.005 (2)
C41	0.051 (3)	0.050 (3)	0.043 (3)	0.005 (2)	−0.012 (2)	−0.005 (2)
C42	0.077 (3)	0.038 (3)	0.055 (3)	0.002 (3)	−0.015 (3)	−0.010 (2)
C43	0.050 (3)	0.044 (3)	0.040 (2)	0.013 (2)	0.003 (2)	0.001 (2)
C44	0.043 (3)	0.050 (3)	0.051 (3)	0.005 (2)	−0.009 (2)	−0.004 (2)
C45	0.037 (2)	0.040 (3)	0.053 (3)	0.005 (2)	−0.003 (2)	−0.003 (2)
C46	0.086 (4)	0.047 (3)	0.060 (3)	0.024 (3)	−0.005 (3)	0.005 (2)
C47	0.227 (9)	0.165 (8)	0.112 (6)	0.157 (7)	0.044 (6)	0.026 (5)
C48	0.164 (7)	0.055 (4)	0.205 (8)	−0.021 (5)	−0.060 (6)	0.053 (5)
C49	0.152 (6)	0.084 (4)	0.085 (4)	0.042 (4)	−0.029 (4)	0.026 (4)
C50	0.034 (2)	0.041 (3)	0.067 (3)	−0.002 (2)	0.003 (2)	0.011 (2)
C51	0.047 (3)	0.067 (4)	0.082 (4)	0.001 (3)	0.005 (3)	0.035 (3)
C52	0.057 (4)	0.088 (5)	0.118 (6)	0.002 (3)	−0.001 (4)	0.062 (5)
C53	0.075 (5)	0.049 (4)	0.184 (9)	0.016 (3)	0.005 (5)	0.035 (5)
C54	0.081 (4)	0.046 (4)	0.149 (7)	0.012 (3)	0.003 (4)	−0.014 (4)
C55	0.056 (3)	0.044 (3)	0.091 (4)	0.005 (3)	0.003 (3)	−0.008 (3)

Geometric parameters (Å, º)

C1—C3	1.348 (6)	C33—C36	1.539 (6)
C1—C2	1.408 (6)	C34—C35	1.392 (6)
C1—H1	0.97 (4)	C34—H34	0.98 (4)
C2—C4	1.355 (6)	C35—H35	0.97 (4)
C2—H2	1.02 (4)	C36—C37	1.464 (7)
C3—C5	1.439 (5)	C36—C39	1.498 (8)
C3—H3	1.02 (4)	C36—C38	1.508 (7)
C4—C6	1.441 (5)	C37—H37A	0.9600
C4—H4	1.01 (4)	C37—H37B	0.9600
C5—C7	1.406 (5)	C37—H37C	0.9600
C5—C6	1.437 (5)	C38—H38A	0.9600
C6—C8	1.402 (5)	C38—H38B	0.9600
C7—C9	1.428 (5)	C38—H38C	0.9600
C7—C20	1.495 (5)	C39—H39A	0.9600
C8—C10	1.431 (5)	C39—H39B	0.9600
C8—C30	1.498 (5)	C39—H39C	0.9600
C9—C11	1.425 (5)	C40—C45	1.384 (5)
C9—C10	1.443 (5)	C40—C41	1.384 (5)
C10—C12	1.422 (5)	C41—C42	1.386 (6)
C11—C13	1.392 (5)	C41—H41	0.98 (4)
C11—C40	1.499 (5)	C42—C43	1.385 (6)
C12—C14	1.402 (5)	C42—H42	0.98 (4)
C12—C50	1.491 (5)	C43—C44	1.373 (6)
C13—C14	1.442 (5)	C43—C46	1.528 (6)
C13—C15	1.442 (5)	C44—C45	1.392 (6)
C14—C16	1.427 (6)	C44—H44	0.95 (4)
C15—C17	1.346 (6)	C45—H45	1.00 (4)
C15—H15	1.01 (4)	C46—C48	1.504 (7)
C16—C18	1.353 (6)	C46—C47	1.519 (7)
C16—H16	0.99 (4)	C46—C49	1.528 (7)
C17—C18	1.412 (7)	C47—H47A	0.9600
C17—H17	1.04 (4)	C47—H47B	0.9600
C18—H18	0.92 (4)	C47—H47C	0.9600
C20—C21	1.385 (6)	C48—H48A	0.9600
C20—C25	1.391 (6)	C48—H48B	0.9600
C21—C22	1.397 (8)	C48—H48C	0.9600
C21—H21	1.00 (5)	C49—H49A	0.9600
C22—C23	1.373 (11)	C49—H49B	0.9600
C22—H22	0.93 (5)	C49—H49C	0.9600
C23—C24	1.344 (11)	C50—C51	1.386 (6)
C23—H23	1.00 (5)	C50—C55	1.401 (6)
C24—C25	1.392 (8)	C51—C52	1.395 (8)
C24—H24	1.00 (5)	C51—H51	1.00 (5)
C25—H25	1.03 (5)	C52—C53	1.374 (9)
C30—C35	1.384 (5)	C52—H52	0.92 (5)
C30—C31	1.388 (5)	C53—C54	1.373 (9)
C31—C32	1.381 (5)	C53—H53	1.02 (5)
C31—H31	0.99 (4)	C54—C55	1.379 (7)
C32—C33	1.387 (6)	C54—H54	1.04 (5)
C32—H32	0.97 (4)	C55—H55	1.06 (5)
C33—C34	1.378 (6)
C3—C1—C2	121.0 (4)	C30—C35—C34	120.5 (4)
C3—C1—H1	121 (3)	C30—C35—H35	121 (3)
C2—C1—H1	118 (3)	C34—C35—H35	118 (3)
C4—C2—C1	120.5 (4)	C37—C36—C39	110.3 (7)
C4—C2—H2	117 (2)	C37—C36—C38	109.7 (6)
C1—C2—H2	123 (2)	C39—C36—C38	104.5 (6)
C1—C3—C5	121.3 (4)	C37—C36—C33	110.7 (4)
C1—C3—H3	120 (2)	C39—C36—C33	109.9 (5)
C5—C3—H3	118 (2)	C38—C36—C33	111.5 (4)
C2—C4—C6	120.8 (4)	C36—C37—H37A	109.5
C2—C4—H4	123 (2)	C36—C37—H37B	109.5
C6—C4—H4	116 (2)	H37A—C37—H37B	109.5
C7—C5—C6	119.9 (4)	C36—C37—H37C	109.5
C7—C5—C3	122.6 (4)	H37A—C37—H37C	109.5
C6—C5—C3	117.5 (4)	H37B—C37—H37C	109.5
C8—C6—C5	119.7 (3)	C36—C38—H38A	109.5
C8—C6—C4	122.0 (4)	C36—C38—H38B	109.5
C5—C6—C4	118.2 (4)	H38A—C38—H38B	109.5
C5—C7—C9	119.5 (3)	C36—C38—H38C	109.5
C5—C7—C20	118.8 (4)	H38A—C38—H38C	109.5
C9—C7—C20	121.2 (3)	H38B—C38—H38C	109.5
C6—C8—C10	119.6 (3)	C36—C39—H39A	109.5
C6—C8—C30	120.4 (3)	C36—C39—H39B	109.5
C10—C8—C30	119.5 (3)	H39A—C39—H39B	109.5
C11—C9—C7	124.0 (3)	C36—C39—H39C	109.5
C11—C9—C10	117.7 (3)	H39A—C39—H39C	109.5
C7—C9—C10	118.4 (3)	H39B—C39—H39C	109.5
C12—C10—C8	122.6 (3)	C45—C40—C41	117.5 (4)
C12—C10—C9	119.2 (3)	C45—C40—C11	122.7 (4)
C8—C10—C9	118.2 (3)	C41—C40—C11	119.8 (3)
C13—C11—C9	120.3 (3)	C40—C41—C42	121.3 (4)
C13—C11—C40	119.3 (3)	C40—C41—H41	118 (3)
C9—C11—C40	119.9 (3)	C42—C41—H41	121 (3)
C14—C12—C10	119.3 (3)	C43—C42—C41	121.5 (4)
C14—C12—C50	119.6 (4)	C43—C42—H42	124 (3)
C10—C12—C50	120.5 (3)	C41—C42—H42	114 (3)
C11—C13—C14	120.1 (3)	C44—C43—C42	116.9 (4)
C11—C13—C15	122.1 (4)	C44—C43—C46	122.1 (4)
C14—C13—C15	117.8 (4)	C42—C43—C46	121.0 (4)
C12—C14—C16	122.5 (4)	C43—C44—C45	122.3 (4)
C12—C14—C13	119.6 (4)	C43—C44—H44	122 (3)
C16—C14—C13	117.9 (4)	C45—C44—H44	116 (3)
C17—C15—C13	121.4 (4)	C40—C45—C44	120.5 (4)
C17—C15—H15	123 (3)	C40—C45—H45	120 (3)
C13—C15—H15	115 (3)	C44—C45—H45	120 (3)
C18—C16—C14	121.2 (4)	C48—C46—C47	109.6 (6)
C18—C16—H16	120 (3)	C48—C46—C49	108.3 (5)
C14—C16—H16	119 (3)	C47—C46—C49	107.0 (5)
C15—C17—C18	120.2 (4)	C48—C46—C43	111.1 (4)
C15—C17—H17	118 (2)	C47—C46—C43	108.6 (4)
C18—C17—H17	122 (2)	C49—C46—C43	112.1 (4)
C16—C18—C17	121.0 (5)	C46—C47—H47A	109.5
C16—C18—H18	123 (3)	C46—C47—H47B	109.5
C17—C18—H18	116 (3)	H47A—C47—H47B	109.5
C21—C20—C25	119.0 (5)	C46—C47—H47C	109.5
C21—C20—C7	122.6 (4)	H47A—C47—H47C	109.5
C25—C20—C7	118.2 (4)	H47B—C47—H47C	109.5
C20—C21—C22	120.2 (6)	C46—C48—H48A	109.5
C20—C21—H21	117 (3)	C46—C48—H48B	109.5
C22—C21—H21	123 (3)	H48A—C48—H48B	109.5
C23—C22—C21	119.4 (7)	C46—C48—H48C	109.5
C23—C22—H22	123 (4)	H48A—C48—H48C	109.5
C21—C22—H22	118 (4)	H48B—C48—H48C	109.5
C24—C23—C22	120.8 (7)	C46—C49—H49A	109.5
C24—C23—H23	118 (3)	C46—C49—H49B	109.5
C22—C23—H23	122 (3)	H49A—C49—H49B	109.5
C23—C24—C25	120.9 (7)	C46—C49—H49C	109.5
C23—C24—H24	126 (3)	H49A—C49—H49C	109.5
C25—C24—H24	113 (3)	H49B—C49—H49C	109.5
C20—C25—C24	119.5 (6)	C51—C50—C55	118.4 (5)
C20—C25—H25	116 (3)	C51—C50—C12	124.2 (4)
C24—C25—H25	124 (3)	C55—C50—C12	117.3 (4)
C35—C30—C31	118.0 (4)	C50—C51—C52	119.8 (6)
C35—C30—C8	118.3 (3)	C50—C51—H51	119 (3)
C31—C30—C8	123.6 (4)	C52—C51—H51	121 (3)
C32—C31—C30	120.7 (4)	C53—C52—C51	120.8 (6)
C32—C31—H31	118 (3)	C53—C52—H52	123 (3)
C30—C31—H31	121 (3)	C51—C52—H52	117 (4)
C31—C32—C33	122.0 (4)	C52—C53—C54	120.0 (6)
C31—C32—H32	117 (3)	C52—C53—H53	119 (3)
C33—C32—H32	121 (3)	C54—C53—H53	121 (3)
C34—C33—C32	116.9 (4)	C53—C54—C55	119.8 (6)
C34—C33—C36	121.2 (4)	C53—C54—H54	121 (3)
C32—C33—C36	121.9 (4)	C55—C54—H54	119 (3)
C33—C34—C35	122.0 (4)	C54—C55—C50	121.2 (6)
C33—C34—H34	121 (3)	C54—C55—H55	120 (3)
C35—C34—H34	117 (3)	C50—C55—H55	118 (3)