1-(p-Bi­phenyl)-4'-(2-naphthyl)­cubane

In the title compound, C₃₀H₂₂, the bi­phenyl and naphthyl substituents are each planar to within 0.03 Å. They extend from the cubane like the wings of a butterfly, with a slight dihedral angle of 9.4 (2)° between their planes. In the crystal structure, the naphthyl groups form close-packed stacks, with cubyls and bi­phenyls extending alternately to the right and the left.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.062
• wR factor = 0.168
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda               -0.2133
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   7.3297
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ...       7.33
PLAT320_ALERT_2_C Check Hybridisation of  C1     in Main Residue          ?
PLAT320_ALERT_2_C Check Hybridisation of  C3     in Main Residue          ?
PLAT320_ALERT_2_C Check Hybridisation of  C4     in Main Residue          ?
PLAT320_ALERT_2_C Check Hybridisation of  C5     in Main Residue          ?
PLAT320_ALERT_2_C Check Hybridisation of  C7     in Main Residue          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang..          8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ......         16

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           68.78
           From the CIF: _reflns_number_total               2001
           Count of symmetry unique reflns         2002
           Completeness (_total/calc)             99.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

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

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S1. Comment

The title molecule, (I), was synthesized by Eaton et al. (1999) along with 1-(p-biphenyl)-4'-(2-naphthyl)-p-[2]cubyl, and a series of other polycubyl molecules to study the properties of cubanes that are linked together at the 1 and 4 positions. Because poly-1,4-cubanes are semi-rigid rod-like structures, the distances between two terminal substituents are fixed, even in solution, making them useful for studying the distance dependence of intramolecular electron-transfer reactions. Paulson et al. (1993) studied the electron-transfer reaction of the title compound by irradiating the molecules (in solution) with high-energy electrons and photometrically observing electron transfer in the anionic form of (I). They found that using cubane as a spacer enhanced the electron transfer rate between the biphenyl and naphthyl groups. Compared to the electron transfer between the same substituents on cyclohexane spacers, the rate of transfer was measured to be 10±3 times larger for the cubane compound. Stronger bond-to-bond couplings and a larger number of pathways are offered as explanations for the enhanced coupling through cubane spacers. Increasing the distance by doubling or tripling the number of cubyl or cyclohexyl spacers leads to an exponential decline in transfer rate with distance; the fall-off with distance was similar for both types of spacer.

The biphenyl groups of (I) are nearly planar, with all C atoms fitting a least-squares plane to within a full range of ±0.031 Å (Fig. 1 and Table 1). The average torsion angle of the biphenyl linkage is 2.1°, versus an average of 23.4° for 772 similar biphenyl linkages (all those with four H atoms adjacent to the central linkage bond) found in the Cambridge Structural Database (Version 5.24; Allen, 2002). The naphthyl groups are even more closely planar; their C atoms fit a least-squares plane to within ±0.007 Å.

The title molecule, (I), has a complex supramolecular assembly. Looking down the a axis (Fig. 2), one can see stacks of intercalated biphenyl groups at the ends of the cell, and a close-packed stack of naphthyl substituents in the center of the cell. There is a twofold screw axis along b which goes through the central naphthyl stack. Fig. 3 illustrates an end-on view of a naphthyl stack, showing that is actually a herring-bone stack, not a stack wherein all planes are parallel. Despite the presence of the close-packed naphthyl stacks and slightly looser biphenyl stacks there are no intermolecular contacts that are significantly less than the sum of van der Waals radii.

S2. Experimental

The crystals were provided by Philip Eaton and Todd Emrick of the University of Chicago. Details of the synthesis of the title molecule, (I), from 1,4-diiodocubane, p-biphenyllithium and naphthalene-1,4-oxide were reported by Eaton et al. (1999). Crystals were grown by slow evaporation from an n-octane solution.

S3. Refinement

Although the space group is acentric, with Mo Kα radiation and only carbon and hydrogen elements there is no basis for determining the absolute configuration. Friedel equivalents were merged, and the `handedness' displayed by the structure (if any) is purely arbitrary. The Flack (1983) parameter, before merging, refined to a value of 2(5). All H atoms were found in difference Fourier maps, but during the refinement they were placed at ideal (SHELXTL) tetrahedral or trigonal positions. They were riding on their bonded neighbors during the refinement, with periodic reidealization, and their displacement parameters were set to be isotropic, with a value equal to 1.2U_eq of the neighboring C atom.

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 25% probability level.
	Fig. 2. A packing diagram of (I), looking down the short a axis, illustrating the close-packed naphthyl groups and the intercalated biphenyl groups.
	Fig. 3. A space-filled diagram illustrating an edge-on view of the close-packed stacks of naphthyl groups. The biphenyl rings have been omitted for clarity and the cubanes are represented by large labeled spheres.

1-(p-biphenyl)-4'-(2-napthyl)cubane

Crystal data

C30H22	F(000) = 404
Mr = 382.48	Dx = 1.276 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 22 reflections
a = 5.9788 (4) Å	θ = 6.2–42.2°
b = 7.579 (1) Å	µ = 0.55 mm^−1
c = 22.044 (1) Å	T = 294 K
β = 94.570 (8)°	Thin lath, colorless
V = 995.71 (15) Å^3	0.52 × 0.16 × 0.02 mm
Z = 2

Data collection

Siemens P4 diffractometer	1271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 68.8°, θmin = 4.0°
ω scans	h = −7→7
Absorption correction: integration (Wuensch et al., 1965)	k = −9→1
Tmin = 0.847, Tmax = 0.988	l = 0→26
2001 measured reflections	3 standard reflections every 97 reflections
2001 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.062	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 0.2164P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.168	(Δ/σ)max = 0.002
S = 1.08	Δρmax = 0.17 e Å^−3
2001 reflections	Δρmin = −0.19 e Å^−3
273 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
7 restraints	Extinction coefficient: 0.0034 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: see text
Secondary atom site location: structure-invariant direct methods

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 > 2σ(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	1.1372 (9)	0.8394 (10)	0.3325 (2)	0.0527 (15)
C2	1.1800 (12)	0.6999 (11)	0.2828 (3)	0.073 (2)
H2A	1.2573	0.5872	0.2906	0.088*
C3	1.2549 (10)	0.8428 (11)	0.2393 (2)	0.0686 (19)
H3A	1.3888	0.8365	0.2165	0.082*
C4	1.0094 (10)	0.8620 (10)	0.2106 (2)	0.0548 (15)
C5	0.9345 (12)	0.7187 (10)	0.2554 (3)	0.070 (2)
H5A	0.8334	0.6202	0.2442	0.084*
C6	0.8926 (9)	0.8608 (13)	0.3032 (3)	0.068 (2)
H6A	0.7588	0.8669	0.3260	0.081*
C7	0.9657 (11)	1.0056 (10)	0.2597 (3)	0.0657 (19)
H7A	0.8884	1.1182	0.2517	0.079*
C8	1.2112 (12)	0.9841 (10)	0.2875 (3)	0.0658 (19)
H8A	1.3126	1.0823	0.2990	0.079*
C1A	0.7824 (9)	0.8760 (9)	0.0197 (2)	0.0490 (13)
C2A	0.9826 (10)	0.7938 (9)	0.0406 (2)	0.0619 (18)
H2AA	1.0680	0.7374	0.0129	0.074*
C3A	1.0565 (11)	0.7943 (9)	0.1014 (2)	0.0627 (18)
H3AA	1.1919	0.7395	0.1136	0.075*
C4A	0.9363 (10)	0.8737 (10)	0.1450 (2)	0.0553 (16)
C5A	0.7383 (10)	0.9570 (10)	0.1244 (3)	0.0634 (18)
H5AA	0.6544	1.0148	0.1521	0.076*
C6A	0.6633 (10)	0.9557 (10)	0.0635 (3)	0.0608 (18)
H6AA	0.5276	1.0103	0.0516	0.073*
C1B	0.6999 (9)	0.8777 (8)	−0.0457 (2)	0.0478 (13)
C2B	0.8221 (12)	0.8024 (10)	−0.0894 (3)	0.074 (2)
H2BA	0.9591	0.7494	−0.0777	0.089*
C3B	0.7447 (12)	0.8043 (12)	−0.1505 (3)	0.086 (3)
H3BA	0.8292	0.7507	−0.1790	0.103*
C4B	0.5461 (12)	0.8839 (12)	−0.1693 (3)	0.077 (2)
H4BA	0.4964	0.8884	−0.2103	0.092*
C5B	0.4242 (12)	0.9556 (11)	−0.1269 (3)	0.079 (2)
H5BA	0.2870	1.0078	−0.1388	0.095*
C6B	0.4978 (10)	0.9533 (10)	−0.0663 (3)	0.0665 (19)
H6BA	0.4090	1.0042	−0.0383	0.080*
C1C	1.0753 (9)	0.8718 (9)	0.4430 (2)	0.0485 (14)
H1CA	0.9358	0.9219	0.4321	0.058*
C2C	1.2093 (9)	0.8218 (8)	0.3984 (2)	0.0485 (15)
C3C	1.4193 (9)	0.7448 (9)	0.4153 (3)	0.0584 (17)
H3CA	1.5101	0.7089	0.3853	0.070*
C4C	1.4920 (10)	0.7219 (8)	0.4749 (3)	0.0546 (15)
H4CA	1.6328	0.6731	0.4849	0.065*
C5C	1.4256 (10)	0.7481 (8)	0.5842 (2)	0.0585 (17)
H5CA	1.5643	0.6975	0.5955	0.070*
C6C	1.2907 (11)	0.7991 (11)	0.6277 (3)	0.069 (2)
H6CA	1.3382	0.7839	0.6686	0.083*
C7C	1.0822 (10)	0.8738 (10)	0.6116 (2)	0.0637 (17)
H7CA	0.9904	0.9062	0.6419	0.076*
C8C	1.0104 (10)	0.9003 (9)	0.5520 (2)	0.0548 (16)
H8CA	0.8717	0.9528	0.5420	0.066*
C9C	1.1454 (8)	0.8485 (8)	0.5053 (2)	0.0417 (12)
C10C	1.3566 (9)	0.7712 (8)	0.5214 (2)	0.0481 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.060 (3)	0.056 (4)	0.043 (3)	−0.007 (4)	0.010 (3)	−0.001 (3)
C2	0.103 (6)	0.067 (4)	0.050 (4)	0.011 (4)	0.011 (4)	−0.001 (3)
C3	0.072 (4)	0.090 (5)	0.047 (3)	−0.006 (4)	0.020 (3)	−0.001 (4)
C4	0.069 (4)	0.057 (4)	0.039 (3)	−0.003 (4)	0.012 (3)	0.003 (3)
C5	0.095 (5)	0.068 (5)	0.047 (4)	−0.025 (4)	−0.001 (3)	0.002 (3)
C6	0.056 (3)	0.102 (6)	0.048 (3)	−0.008 (5)	0.018 (3)	0.006 (4)
C7	0.087 (5)	0.065 (4)	0.046 (3)	0.018 (4)	0.007 (3)	−0.002 (3)
C8	0.088 (5)	0.069 (4)	0.040 (3)	−0.024 (4)	0.003 (3)	0.000 (3)
C1A	0.058 (3)	0.046 (3)	0.044 (3)	0.000 (3)	0.013 (2)	0.004 (3)
C2A	0.071 (4)	0.067 (4)	0.047 (3)	0.024 (4)	0.007 (3)	−0.005 (3)
C3A	0.077 (4)	0.065 (4)	0.047 (3)	0.021 (4)	0.008 (3)	0.000 (3)
C4A	0.067 (4)	0.058 (4)	0.043 (3)	0.002 (4)	0.014 (3)	0.001 (3)
C5A	0.061 (4)	0.084 (5)	0.048 (3)	0.004 (4)	0.021 (3)	−0.007 (4)
C6A	0.054 (3)	0.076 (5)	0.054 (3)	0.017 (4)	0.011 (3)	−0.003 (3)
C1B	0.051 (3)	0.042 (3)	0.051 (3)	−0.003 (3)	0.006 (2)	0.003 (3)
C2B	0.083 (5)	0.086 (6)	0.053 (3)	0.020 (4)	0.001 (3)	−0.009 (4)
C3B	0.099 (5)	0.111 (7)	0.046 (3)	0.020 (5)	0.002 (3)	−0.018 (4)
C4B	0.086 (5)	0.079 (6)	0.063 (4)	−0.006 (5)	−0.017 (4)	0.001 (4)
C5B	0.073 (4)	0.092 (6)	0.072 (4)	0.016 (5)	−0.006 (4)	0.014 (4)
C6B	0.065 (4)	0.082 (5)	0.052 (3)	0.018 (4)	0.007 (3)	0.007 (4)
C1C	0.048 (3)	0.052 (4)	0.046 (3)	0.003 (3)	0.006 (2)	0.001 (3)
C2C	0.050 (3)	0.054 (4)	0.042 (3)	−0.006 (3)	0.008 (2)	0.005 (3)
C3C	0.053 (3)	0.065 (5)	0.060 (4)	0.010 (3)	0.017 (3)	0.007 (3)
C4C	0.050 (3)	0.051 (4)	0.063 (4)	0.002 (3)	0.006 (3)	0.003 (3)
C5C	0.062 (4)	0.057 (4)	0.055 (3)	−0.005 (4)	−0.008 (3)	0.010 (3)
C6C	0.078 (4)	0.084 (6)	0.044 (3)	−0.001 (4)	0.001 (3)	0.015 (4)
C7C	0.071 (4)	0.077 (5)	0.044 (3)	−0.001 (4)	0.010 (3)	0.000 (4)
C8C	0.055 (3)	0.064 (4)	0.046 (3)	0.005 (3)	0.006 (2)	−0.004 (3)
C9C	0.044 (3)	0.041 (3)	0.041 (3)	−0.002 (3)	0.001 (2)	0.001 (3)
C10C	0.046 (3)	0.046 (3)	0.052 (3)	−0.003 (3)	0.000 (2)	0.003 (3)

Geometric parameters (Å, º)

C1—C2C	1.487 (7)	C6A—H6AA	0.9300
C1—C2	1.559 (9)	C1B—C2B	1.378 (8)
C1—C6	1.560 (8)	C1B—C6B	1.381 (7)
C1—C8	1.566 (9)	C2B—C3B	1.390 (7)
C2—C3	1.535 (9)	C2B—H2BA	0.9300
C2—C5	1.549 (10)	C3B—C4B	1.366 (9)
C2—H2A	0.9800	C3B—H3BA	0.9300
C3—C8	1.546 (9)	C4B—C5B	1.345 (9)
C3—C4	1.559 (8)	C4B—H4BA	0.9300
C3—H3A	0.9800	C5B—C6B	1.373 (8)
C4—C4A	1.480 (7)	C5B—H5BA	0.9300
C4—C5	1.558 (9)	C6B—H6BA	0.9300
C4—C7	1.573 (9)	C1C—C2C	1.370 (7)
C5—C6	1.540 (10)	C1C—C9C	1.415 (6)
C5—H5A	0.9800	C1C—H1CA	0.9300
C6—C7	1.542 (10)	C2C—C3C	1.408 (8)
C6—H6A	0.9800	C3C—C4C	1.360 (7)
C7—C8	1.553 (9)	C3C—H3CA	0.9300
C7—H7A	0.9800	C4C—C10C	1.407 (7)
C8—H8A	0.9800	C4C—H4CA	0.9300
C1A—C6A	1.385 (7)	C5C—C6C	1.359 (8)
C1A—C2A	1.395 (8)	C5C—C10C	1.423 (7)
C1A—C1B	1.485 (7)	C5C—H5CA	0.9300
C2A—C3A	1.378 (7)	C6C—C7C	1.389 (8)
C2A—H2AA	0.9300	C6C—H6CA	0.9300
C3A—C4A	1.382 (7)	C7C—C8C	1.365 (7)
C3A—H3AA	0.9300	C7C—H7CA	0.9300
C4A—C5A	1.386 (8)	C8C—C9C	1.414 (7)
C5A—C6A	1.380 (7)	C8C—H8CA	0.9300
C5A—H5AA	0.9300	C9C—C10C	1.411 (7)
C2C—C1—C2	125.1 (6)	C3A—C4A—C5A	116.7 (5)
C2C—C1—C6	127.1 (5)	C3A—C4A—C4	121.6 (6)
C2—C1—C6	88.8 (5)	C5A—C4A—C4	121.7 (5)
C2C—C1—C8	127.3 (6)	C6A—C5A—C4A	121.2 (6)
C2—C1—C8	87.6 (4)	C6A—C5A—H5AA	119.4
C6—C1—C8	88.1 (5)	C4A—C5A—H5AA	119.4
C3—C2—C5	90.4 (5)	C5A—C6A—C1A	122.5 (6)
C3—C2—C1	91.9 (6)	C5A—C6A—H6AA	118.8
C5—C2—C1	90.5 (5)	C1A—C6A—H6AA	118.8
C3—C2—H2A	124.6	C2B—C1B—C6B	116.2 (5)
C5—C2—H2A	124.6	C2B—C1B—C1A	121.4 (5)
C1—C2—H2A	124.6	C6B—C1B—C1A	122.4 (5)
C2—C3—C8	89.2 (4)	C1B—C2B—C3B	121.3 (7)
C2—C3—C4	90.4 (5)	C1B—C2B—H2BA	119.4
C8—C3—C4	90.5 (5)	C3B—C2B—H2BA	119.4
C2—C3—H3A	125.2	C4B—C3B—C2B	120.8 (7)
C8—C3—H3A	125.2	C4B—C3B—H3BA	119.6
C4—C3—H3A	125.2	C2B—C3B—H3BA	119.6
C4A—C4—C5	125.7 (6)	C5B—C4B—C3B	118.3 (7)
C4A—C4—C3	126.8 (5)	C5B—C4B—H4BA	120.8
C5—C4—C3	89.2 (5)	C3B—C4B—H4BA	120.8
C4A—C4—C7	125.4 (6)	C4B—C5B—C6B	121.4 (7)
C5—C4—C7	88.5 (4)	C4B—C5B—H5BA	119.3
C3—C4—C7	89.2 (5)	C6B—C5B—H5BA	119.3
C6—C5—C2	89.9 (5)	C5B—C6B—C1B	122.0 (6)
C6—C5—C4	91.0 (6)	C5B—C6B—H6BA	119.0
C2—C5—C4	90.0 (5)	C1B—C6B—H6BA	119.0
C6—C5—H5A	125.1	C2C—C1C—C9C	121.1 (5)
C2—C5—H5A	125.1	C2C—C1C—H1CA	119.4
C4—C5—H5A	125.1	C9C—C1C—H1CA	119.4
C5—C6—C7	90.2 (4)	C1C—C2C—C3C	119.0 (5)
C5—C6—C1	90.7 (5)	C1C—C2C—C1	122.3 (5)
C7—C6—C1	91.7 (5)	C3C—C2C—C1	118.7 (5)
C5—C6—H6A	124.6	C4C—C3C—C2C	121.3 (6)
C7—C6—H6A	124.6	C4C—C3C—H3CA	119.4
C1—C6—H6A	124.6	C2C—C3C—H3CA	119.4
C6—C7—C8	89.2 (5)	C3C—C4C—C10C	120.8 (6)
C6—C7—C4	90.3 (5)	C3C—C4C—H4CA	119.6
C8—C7—C4	89.8 (5)	C10C—C4C—H4CA	119.6
C6—C7—H7A	125.4	C6C—C5C—C10C	120.7 (6)
C8—C7—H7A	125.4	C6C—C5C—H5CA	119.7
C4—C7—H7A	125.4	C10C—C5C—H5CA	119.7
C3—C8—C7	90.5 (5)	C5C—C6C—C7C	120.4 (6)
C3—C8—C1	91.2 (5)	C5C—C6C—H6CA	119.8
C7—C8—C1	91.0 (5)	C7C—C6C—H6CA	119.8
C3—C8—H8A	124.6	C8C—C7C—C6C	120.9 (6)
C7—C8—H8A	124.6	C8C—C7C—H7CA	119.6
C1—C8—H8A	124.6	C6C—C7C—H7CA	119.6
C6A—C1A—C2A	116.1 (5)	C7C—C8C—C9C	120.4 (6)
C6A—C1A—C1B	121.6 (5)	C7C—C8C—H8CA	119.8
C2A—C1A—C1B	122.3 (5)	C9C—C8C—H8CA	119.8
C3A—C2A—C1A	121.4 (6)	C10C—C9C—C8C	118.9 (5)
C3A—C2A—H2AA	119.3	C10C—C9C—C1C	119.1 (5)
C1A—C2A—H2AA	119.3	C8C—C9C—C1C	122.0 (5)
C2A—C3A—C4A	122.2 (6)	C4C—C10C—C9C	118.8 (5)
C2A—C3A—H3AA	118.9	C4C—C10C—C5C	122.5 (6)
C4A—C3A—H3AA	118.9	C9C—C10C—C5C	118.7 (5)
C2C—C1—C2—C3	−134.8 (6)	C2C—C1—C8—C7	−136.3 (6)
C6—C1—C2—C3	88.8 (5)	C2—C1—C8—C7	89.8 (5)
C8—C1—C2—C3	0.7 (5)	C6—C1—C8—C7	0.9 (5)
C2C—C1—C2—C5	134.8 (6)	C6A—C1A—C2A—C3A	−0.6 (9)
C6—C1—C2—C5	−1.6 (5)	C1B—C1A—C2A—C3A	179.8 (7)
C8—C1—C2—C5	−89.8 (5)	C1A—C2A—C3A—C4A	0.9 (11)
C5—C2—C3—C8	89.8 (5)	C2A—C3A—C4A—C5A	−1.4 (11)
C1—C2—C3—C8	−0.7 (5)	C2A—C3A—C4A—C4	175.5 (6)
C5—C2—C3—C4	−0.7 (6)	C5—C4—C4A—C3A	−91.9 (9)
C1—C2—C3—C4	−91.2 (5)	C3—C4—C4A—C3A	29.1 (12)
C2—C3—C4—C4A	−135.2 (7)	C7—C4—C4A—C3A	149.9 (7)
C8—C3—C4—C4A	135.5 (7)	C5—C4—C4A—C5A	84.8 (9)
C2—C3—C4—C5	0.7 (6)	C3—C4—C4A—C5A	−154.2 (7)
C8—C3—C4—C5	−88.5 (5)	C7—C4—C4A—C5A	−33.4 (10)
C2—C3—C4—C7	89.2 (5)	C3A—C4A—C5A—C6A	1.8 (11)
C8—C3—C4—C7	0.0 (6)	C4—C4A—C5A—C6A	−175.1 (7)
C3—C2—C5—C6	−90.3 (6)	C4A—C5A—C6A—C1A	−1.7 (11)
C1—C2—C5—C6	1.6 (5)	C2A—C1A—C6A—C5A	1.0 (10)
C3—C2—C5—C4	0.7 (6)	C1B—C1A—C6A—C5A	−179.4 (7)
C1—C2—C5—C4	92.6 (6)	C6A—C1A—C1B—C2B	178.2 (7)
C4A—C4—C5—C6	−134.1 (6)	C2A—C1A—C1B—C2B	−2.2 (10)
C3—C4—C5—C6	89.2 (5)	C6A—C1A—C1B—C6B	−2.0 (10)
C7—C4—C5—C6	0.0 (5)	C2A—C1A—C1B—C6B	177.6 (7)
C4A—C4—C5—C2	136.0 (6)	C6B—C1B—C2B—C3B	0.3 (11)
C3—C4—C5—C2	−0.7 (6)	C1A—C1B—C2B—C3B	−179.9 (7)
C7—C4—C5—C2	−90.0 (5)	C1B—C2B—C3B—C4B	1.2 (12)
C2—C5—C6—C7	90.0 (5)	C2B—C3B—C4B—C5B	−2.0 (12)
C4—C5—C6—C7	0.0 (5)	C3B—C4B—C5B—C6B	1.5 (12)
C2—C5—C6—C1	−1.6 (5)	C4B—C5B—C6B—C1B	0.0 (12)
C4—C5—C6—C1	−91.6 (5)	C2B—C1B—C6B—C5B	−0.8 (10)
C2C—C1—C6—C5	−133.3 (7)	C1A—C1B—C6B—C5B	179.4 (7)
C2—C1—C6—C5	1.6 (5)	C9C—C1C—C2C—C3C	0.5 (10)
C8—C1—C6—C5	89.3 (5)	C9C—C1C—C2C—C1	178.0 (6)
C2C—C1—C6—C7	136.4 (7)	C2—C1—C2C—C1C	−139.1 (7)
C2—C1—C6—C7	−88.6 (5)	C6—C1—C2C—C1C	−19.0 (11)
C8—C1—C6—C7	−0.9 (5)	C8—C1—C2C—C1C	102.6 (8)
C5—C6—C7—C8	−89.8 (5)	C2—C1—C2C—C3C	38.4 (9)
C1—C6—C7—C8	0.9 (5)	C6—C1—C2C—C3C	158.4 (7)
C5—C6—C7—C4	0.0 (5)	C8—C1—C2C—C3C	−79.9 (8)
C1—C6—C7—C4	90.7 (5)	C1C—C2C—C3C—C4C	−1.0 (10)
C4A—C4—C7—C6	134.3 (6)	C1—C2C—C3C—C4C	−178.6 (6)
C5—C4—C7—C6	0.0 (5)	C2C—C3C—C4C—C10C	1.4 (10)
C3—C4—C7—C6	−89.2 (5)	C10C—C5C—C6C—C7C	0.4 (11)
C4A—C4—C7—C8	−136.5 (6)	C5C—C6C—C7C—C8C	−1.2 (12)
C5—C4—C7—C8	89.3 (5)	C6C—C7C—C8C—C9C	1.4 (11)
C3—C4—C7—C8	0.0 (6)	C7C—C8C—C9C—C10C	−0.8 (9)
C2—C3—C8—C7	−90.4 (5)	C7C—C8C—C9C—C1C	179.2 (7)
C4—C3—C8—C7	0.0 (6)	C2C—C1C—C9C—C10C	−0.5 (9)
C2—C3—C8—C1	0.7 (5)	C2C—C1C—C9C—C8C	179.6 (6)
C4—C3—C8—C1	91.1 (5)	C3C—C4C—C10C—C9C	−1.3 (9)
C6—C7—C8—C3	90.3 (6)	C3C—C4C—C10C—C5C	179.4 (6)
C4—C7—C8—C3	0.0 (6)	C8C—C9C—C10C—C4C	−179.2 (6)
C6—C7—C8—C1	−0.9 (5)	C1C—C9C—C10C—C4C	0.8 (8)
C4—C7—C8—C1	−91.3 (5)	C8C—C9C—C10C—C5C	0.1 (8)
C2C—C1—C8—C3	133.2 (6)	C1C—C9C—C10C—C5C	−179.9 (6)
C2—C1—C8—C3	−0.6 (5)	C6C—C5C—C10C—C4C	179.3 (6)
C6—C1—C8—C3	−89.5 (5)	C6C—C5C—C10C—C9C	0.1 (9)