A low-temperature polymorph of m-quinquephenyl

A low-temperature polymorph of 1,1′:3′,1′′:3′′,1′′′:3′′′,1′′′′-quinquephenyl (m-quinquephenyl), C₃₀H₂₂, crystallizes in the space group P2₁/c with two mol­ecules in the asymmetric unit. The crystal is a three-component nonmerohedral twin. A previously reported room-temperature polymorph [Rabideau, Sygula, Dhar & Fronczek (1993). Chem. Commun. pp. 1795–1797] also crystallizes with two mol­ecules in the asymmetric unit in the space group P. The unit-cell volume for the low-temperature polymorph is 4120.5 (4) ų, almost twice that of the room-temperature polymorph which is 2102.3 (6) ų. The mol­ecules in both structures adopt a U-shaped conformation with similar geometric parameters. The structural packing is similar in both compounds, with the mol­ecules lying in layers which stack perpendicular to the longest unit-cell axis. The mol­ecules pack alternately in the layers and in the stacked columns. In both polymorphs, the only inter­actions between the mol­ecules which can stabilize the packing are very weak C—H...π inter­actions.

S1. Comment

Polyphenyls are used in technological industries, either directly (e.g. as dyes, thermal printing materials or coolants) or as starting materials for functionalized derivatives that are incorporated, for instance, in nonspreading lubricants, emulsifiers, optical brighteners, crop protection products and plastics. In spite of this, experimental data for thermochemical parameters of these compounds that would permit inferences to be made concerning not only their relative stability, but also structure/molecular energetics relationships or thermophysical properties, are scarce.

In the course of a thermochemical study of polyphenylenes, particularly with regard to the effect of isomerization on the fusion temperatures, heat capacities, enthalpies of formation and enthalpies of vaporization, m-quinquephenyl, (I), has been synthesized, following a similar procedure used for a previously optimized Suzuki–Miyaura cross-coupling reaction (Suzuki, 2011; Miyaura, 2002) for polyphenyl compounds (Lima et al., 2011). A search of the literature revealed that (I) had already been characterized structurally by X-ray diffraction at room temperature (283–303 K; [Reference?]). Nevertheless, it is well known that isomers belonging to the parent series of p-polyphenyl oligomers [n(phenyl) = 3–4] undergo solid-phase transitions (Baker et al., 1990, and references therein). Those transitions are characterized by an order/disorder phase change, from twisted (at lower temperatures) to planar (when heated) (Delugeard et al., 1976; Baudour et al., 1978), so the question of whether a phase transition would occur in the m-quinquephenyl isomer was raised, driving interest in the structural characterization of the compound at low temperatures. Furthermore, the identification and characterization of the polymorphic forms is essential to an accurate interpretation of, for instance, experimental calorimetric results.

The low-temperature (LT) measurement, performed at 150 K, revealed that (I) crystallizes in the space group P2₁/c with a unit-cell volume of 4120.5 (4) ų, and with two molecules (LTA and LTB) in the asymmetric unit (Fig. 1). These data show that the structure at low temperature is a polymorph of the earlier structure of (I) found by Rabideau et al. (1993) in a room-temperature (RT) determination (R = 0.052). At RT, (I) crystallizes in the space group P1 with a unit-cell volume of 2102.3 (6) ų, and with two molecules in the asymmetric unit (RTA and RTB; Fig. 2). The RT unit-cell dimensions are: a = 7.7620 (6), b = 13.618 (2) and c = 21.623 (5) Å, and α = 80.58 (2), β = 85.26 (1) and γ = 89.71 (1)°. As can be seen from the crystal data table for the LT structure, there is a rough relationship between the unit-cell dimensions for each compound: a'(RT) ≈ b(LT), b' ≈ a, c' ≈ c/2, α' ≈ (180 - β)°, and β' and γ' are quite close to 90°, so swapping the a and b axes and doubling c effectively changes the RT cell to the LT cell.

The m-polyphenyls might be expected to adopt a zigzag conformation in order to minimize steric repulsion between the phenyl groups, but in both LT and RT crystal structures of (I) the U-shaped conformation is preferred. Theoretical calculations made earlier using MM2/87 (Rabideau et al., 1993) showed that there is no apparent energetic restraint preventing the zigzag conformation in favour of the U-shaped conformation. The calculations were indicative that both conformers and their intermediate geometries are energetically similar, with torsion barriers of about 5 kJ mol^-1. All molecules have a very similar geometry. The dihedral angles between successive rings along the chain (Table 1) show that they lie within the same angular range and show similar trends. The results of a least-squares fit of the 30 C atoms using PLATON MOLFIT with quaternion transformation (Mackay, 1984; Spek, 2009) for the molecules in pairs are given in Table 2. Columns 3 and 5 provide values for the root mean-square (r.m.s.) distance between equivalent (overlapping/superimposed) atoms in the fitted molecules. These give rise to values for the molecular isometricity index, defined as I_i(n^*) = |[Σ(ΔR_i)²/n]^1/2 - 1| × 100 for n = 30 (Kálmán et al., 1993), given in columns 4 and 6 of Table 2. The r.m.s. bond-length and bond-angle differences between equivalent bonds and angles within each pair of molecules are also given in Table 2. As a consequence of the arbitrary choice of asymmetric unit, molecules A and B are mirror images of one another, as shown by the need to invert one of them to optimize the fit with the other. The MOLFIT parameters and the dihedral angles are indicative that the molecules have very similar conformations, as can be best viewed in the plots of the fitted molecules given in Fig. 3.

The values in Table 3 are consistent with the molecules in each bimolecular asymmetric unit being related to one another by a noncrystallographic glide plane, which ensures the invariance of the z coordinates for each pair of molecules. For the RT structure it is an a-glide parallel to (010), while for the LT structure it is a b-glide parallel to (100). Thus, in both structures, the molecules in the asymmetric unit sit above one another, with a separation of 0.5 along the b or a axis and an offset of 0.25 along the a or b axis for the LT and RT structures, respectively. As shown in Figs. 4 and 5, the unit cell of the RT structure contains two layers of molecules centred on z = 1/4 and 3/4 and related to one another by the operation of crystallographic centres of symmetry, which is the only relationship between neighbouring layers as they are stacked in the direction of c. The situation in the LT structure is more complex. As shown in Figs. 6 and 7, the unit cell of the LT structure encompasses four layers of molecules centred on z = 1/8, 3/8, 5/8 and 7/8. The layers at z = 1/8 and 3/8 are related to one another by the operation of crystallographic twofold screw axes and the same is true for the layers at z = 5/8 and 7/8. The layers at z = 1/8 and 5/8 are related by the operation of crystallographic c-glide planes and the same is true for the layers at z = 3/8 and 7/8. Pairs of layers are now, of course, centred on z = 1/4 and 3/4 and are related to one another, as they are stacked in the direction of c, by the operation of crystallographic centres of inversion, together with the operation of the crystallographic c-glide planes already mentioned.

There are no π–π interactions in the structures. Table 4 lists values of distances and angles for the most relevant close contacts between molecules. These values are indicative that the contacts are too weak and may not be considered as significant C—H···π interactions. Comparison of the values between polymorphs, for corresponding contacts, suggests that they are stronger in the LT polymorph. The packing motifs, molecular conformations and mutual orientations of the molecules are very similar in the two structures. Nevertheless, the LT polymorph appears to have a more efficient packing than the RT one, as suggested by the volume allocated per molecule in the LT structure (approximately 10 ų less). This fact is obviously reflected in macroscopic terms by the slight differences in the values for the densities, of 1.233 (calculated) and 1.209 Mg m^-3 (measured) (Rabideau et al., 1993) in the LT and RT structures, respectively. Roughly speaking, for organic compounds, the linear thermal expansion coefficient is less than 0.0001 K^-1, which would give a density of about 1.19 Mg m^-3 to the LT polymorph at room temperature, considering a temperature difference of 140 K between the measurements. The differences found in the densities may be attributed mainly to the thermal expansion of the compound, drawing attention to the role that entropy may play in the formation of the polymorphs.

This kind of polymorphism contrasts with that shown by the homologous p-quinquephenyl. The phase transitions in p-polyphenyls are well established for the case of p-terphenyl and p-quaterphenyl. Those transitions are accompanied by a change in the crystal structure (space group P1 before the transition and space group P2₁/n after the phase transition) associated with an energy change (heat of transition), and therefore a change in the absolute heat capacity of the compound, at the temperature of transition. The structure of the parent p-quinquephenyl has not been determined at low temperatures but Saito et al. (2000) have suggested, based on the measurement of heat capacity excess with temperature, that the parent p-quinquephenyl would have a twist phase transition at about 264 K, similar to what is observed in the p-polyphenyls (n = 3, 4). In the case of p-quaterphenyl, on the basis of the available structural data [p-quaterphenyl, 283–303 K, R = 0.045; Delugeard et al., 1976) and p-quaterphenyl (110 K, R = 0.104; Baudour et al., 1978)], it appears that the individual molecules have significantly different conformations in the high-temperature phase (virtually planar and centrosymmetric) and low-temperature phase (nonplanar and noncentrosymmetric). Furthermore, they each have entirely different supramolecular structures. In the case of the HT form, there are four potential but very weak C—H···π interactions (H···Cg distances in the range 2.83–2.97 Å, with angles at H of 130–137°) stabilizing the supramolecular structure. In the case of the LT form, there are ten potential C—H···π interactions (H···Cg distances of 2.69–2.97 Å and angles at H of 126–144°, of which eight have angles at H greater than 139°) which stabilize the packing. This is the converse of the situation for the high- and low-temperature forms of m-quinquephenyl presented here, where the impact of C—H···π interactions on the supramolecular structures is minimal compared with the p-isomer. Also, apart from the change in torsion angles for the outer phenyl rings in molecule LTB, the molecular geometry is virtually unaffected. These differences may help to understand the effect of isomerization on some of the physical properties of the polyphenyls, such as melting points, enthalpies of formation or vaporization.

Due to the simplicity of the elemental composition of polyphenyls, the only possible stabilization mechanism of their supramolecular structures is through the contribution of weak C—H···π and/or π–π interactions, thus making them good models for the study of the impact of these interactions on molecular geometry, packing or molecular motion constraints, parameters that will be reflected in their physical properties. As far as the p-polyphenyls are concerned, the phase change from low to high temperature leads to a reduction in the interactions and the molecular motion becomes less constrained. This may explain the high heat capacity of these compounds, which makes them good candidates for use as coolants. The molecular motion, symmetry and higher number of C—H···π interactions which the p-oligomers establish in relation to the m-oligomers may explain the higher melting points of the former. Despite that, a comparative analysis of the m-quinquephenyl polymorphs might highlight the role of weak close contacts on cell volume and densities.

Related literature

For related literature, see: Baker et al. (1990); Baudour et al. (1978); Delugeard et al. (1976); Kálmán et al. (1993); Lima et al. (2011); Liu et al. (2006); Mackay (1984); Miyaura (2002); Miyaura & Suzuki (1995); Rabideau et al. (1993); Saito et al. (2000); Sheldrick (2008); Spek (2009); Suzuki (2011); Wieser & Berglund (2009).

S2. Experimental

m-Quinquephenyl was synthesized using the Suzuki–Miyaura aryl cross-coupling method by adapting the procedure described in the literature (Miyaura & Suzuki, 1995; Liu et al., 2006). The compound was synthesized by the reaction of a mixture of 1,3-dibromobenzene (3 mmol), 3-boronic acid (11 mmol), Pd(OAc)₂ (0.1 mmol) and K₂CO₃ (15 mmol) in distilled water (15 ml), toluene (30 ml) and ethanol (10 ml). The mixture was stirred under a nitrogen atmosphere for approximately 10 h at 350 K. The product was purified by recrystallization from methanol and by sublimation under reduced pressure (<10 Pa). The purity of the compounds was checked by gas chromatography, using an HP 4890 apparatus equipped with an HP-5 column, cross-linked, 5% diphenyl and 95% dimethylpolysiloxane, showing a % (m/m) purity greater than 99.8%. The relative atomic masses used were those recommended by the IUPAC Commission in 2007 (Wieser & Berglund, 2009). Crystals suitable for X-ray diffraction were obtained by recrystallization by evaporation from a solution in methanol–acetone (3:1 v/v).

S3. Refinement

H atoms were treated as riding, with aromatic C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). The positions of the H atoms were calculated and checked on a difference map during the refinement.

The crystal was a three-component nonmerohedral twin and was refined using an HKLF 5 reflection file (Sheldrick, 2008) with BASF values of 0.246 (2) and 0.0491 (3). This was discovered after an initial attempt at refinement gave a high R factor and the TwinRotMat option in PLATON (Spek, 2009) revealed the existence of three twin domains. The TwinRotMat option was used to generate the HKLF 5 reflection file from the original data, which had been integrated initially as a nontwinned data set.

The 202, 202, 200, 200, 204 and 102 reflections were omitted as they were obscured by the beam stop.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and OSCAIL (McArdle et al., 2004); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. Molecules (a) LTA and (b) LTB of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecules (a) RTA and (b) RTB of (I), taken from Rabideau et al. (1993), showing the atom-numbering scheme. The spheres are of arbitrary size.
	Fig. 3. Molecular overlay diagrams for all six possible combinations of the molecules of the two structures.
	Fig. 4. A view of the packing of the molecules in the unit cell of the RT form of (I), viewed along the a axis. H atoms have been omitted for clarity. Molecules labelled with an asterisk (*) are at the symmetry position (-x + 1, -y + 1, -z + 1).
	Fig. 5. A view of the packing of the molecules in the unit cell of the RT form of (I), viewed along the b axis. H atoms have been omitted for clarity. Molecules labelled with an asterisk (*) are at the symmetry position (-x + 1, -y + 1, -z + 1).
	Fig. 6. A view of the packing of the molecules in the unit cell of the LT form of (I), viewed along the b axis. H atoms have been omitted for clarity. Molecules labelled with an asterisk (*), hash (#), ampersand (&), plus sign (+) or dollar sign ($) are at the symmetry positions (-x + 1, -y + 1, -z + 1), (-x + 1, y + 1/2, -z + 1/2), (x, -y + 3/2, z + 1/2), (-x + 1, y - 1/2, -z + 1/2) or (x, -y + 1/2, z + 1/2), respectively.
	Fig. 7. A view of the packing of the molecules in the unit cell of the LT form of (I), viewed along the a axis. H atoms have been omitted for clarity. Molecules labelled with an asterisk (*), hash (#), ampersand (&), plus sign (+) or dollar sign ($) are at the symmetry positions (-x + 1, -y + 1, -z + 1), (-x + 1, y + 1/2, -z + 1/2), (x, -y + 3/2, z + 1/2), (-x + 1, y - 1/2, -z + 1/2) or (x, -y + 1/2, z + 1/2), respectively. [Please check axes labels; not clear in original]

1,1':3',1'':3'',1''':3''',1''''-quinquephenyl

Crystal data

C30H22	F(000) = 1616
Mr = 382.48	Dx = 1.233 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 28626 reflections
a = 13.5740 (7) Å	θ = 2.9–26.5°
b = 7.1809 (4) Å	µ = 0.07 mm^−1
c = 42.833 (2) Å	T = 150 K
β = 99.274 (4)°	Needle, colourless
V = 4120.5 (4) Å^3	0.30 × 0.08 × 0.02 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer	8455 independent reflections
Radiation source: fine-focus sealed tube	6424 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 8.33 pixels mm^-1	θmax = 26.5°, θmin = 2.9°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −9→9
Tmin = 0.979, Tmax = 0.999	l = −53→15
28626 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0988P)^2] where P = (Fo^2 + 2Fc^2)/3
8453 reflections	(Δ/σ)max = 0.001
543 parameters	Δρmax = 0.22 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
C11A	0.42665 (17)	0.7263 (3)	0.15232 (5)	0.0275 (5)
C12A	0.51917 (18)	0.7150 (4)	0.17196 (5)	0.0339 (6)
H12A	0.5753	0.6695	0.1636	0.041*
C13A	0.5304 (2)	0.7688 (4)	0.20333 (6)	0.0409 (6)
H13A	0.5937	0.7587	0.2164	0.049*
C14A	0.4496 (2)	0.8374 (4)	0.21572 (6)	0.0419 (7)
H14A	0.4576	0.8785	0.2371	0.050*
C15A	0.3572 (2)	0.8456 (4)	0.19677 (5)	0.0396 (6)
H15A	0.3011	0.8894	0.2053	0.048*
C16A	0.34562 (18)	0.7908 (3)	0.16549 (5)	0.0324 (5)
H16A	0.2815	0.7970	0.1528	0.039*
C21A	0.41579 (16)	0.6744 (3)	0.11825 (5)	0.0253 (5)
C22A	0.49255 (16)	0.7142 (3)	0.10122 (5)	0.0261 (5)
H22A	0.5506	0.7761	0.1116	0.031*
C23A	0.48663 (16)	0.6657 (3)	0.06951 (5)	0.0259 (5)
C24A	0.39996 (17)	0.5785 (3)	0.05429 (5)	0.0306 (5)
H24A	0.3941	0.5452	0.0326	0.037*
C25A	0.32251 (17)	0.5406 (3)	0.07084 (5)	0.0325 (5)
H25A	0.2636	0.4818	0.0604	0.039*
C26A	0.33005 (17)	0.5873 (3)	0.10237 (5)	0.0291 (5)
H26A	0.2764	0.5600	0.1134	0.035*
C31A	0.57269 (17)	0.7040 (3)	0.05304 (5)	0.0271 (5)
C32A	0.66903 (16)	0.6970 (3)	0.06998 (5)	0.0243 (5)
H32A	0.6777	0.6626	0.0917	0.029*
C33A	0.75358 (17)	0.7381 (3)	0.05658 (5)	0.0261 (5)
C34A	0.73898 (19)	0.7850 (3)	0.02437 (5)	0.0309 (5)
H34A	0.7948	0.8152	0.0145	0.037*
C35A	0.6439 (2)	0.7877 (4)	0.00687 (5)	0.0363 (6)
H35A	0.6352	0.8170	−0.0150	0.044*
C36A	0.56147 (18)	0.7482 (4)	0.02089 (5)	0.0325 (6)
H36A	0.4967	0.7512	0.0086	0.039*
C41A	0.85465 (17)	0.7337 (3)	0.07602 (5)	0.0248 (5)
C42A	0.86803 (17)	0.7796 (3)	0.10822 (5)	0.0254 (5)
H42A	0.8116	0.8152	0.1174	0.030*
C43A	0.96152 (17)	0.7749 (3)	0.12728 (5)	0.0265 (5)
C44A	1.04363 (17)	0.7258 (3)	0.11342 (5)	0.0309 (5)
H44A	1.1082	0.7238	0.1259	0.037*
C45A	1.03228 (18)	0.6799 (4)	0.08169 (5)	0.0336 (6)
H45A	1.0890	0.6464	0.0725	0.040*
C46A	0.93914 (18)	0.6825 (3)	0.06326 (5)	0.0309 (5)
H46A	0.9323	0.6489	0.0416	0.037*
C51A	0.97332 (17)	0.8216 (3)	0.16150 (5)	0.0285 (5)
C52A	0.91403 (18)	0.9567 (4)	0.17280 (5)	0.0329 (5)
H52A	0.8646	1.0196	0.1584	0.039*
C53A	0.9262 (2)	1.0006 (4)	0.20470 (5)	0.0421 (7)
H53A	0.8852	1.0930	0.2120	0.051*
C54A	0.9979 (2)	0.9097 (4)	0.22598 (6)	0.0436 (7)
H54A	1.0062	0.9393	0.2479	0.052*
C55A	1.0573 (2)	0.7761 (4)	0.21525 (5)	0.0398 (6)
H55A	1.1070	0.7143	0.2298	0.048*
C56A	1.04489 (18)	0.7315 (4)	0.18329 (5)	0.0337 (6)
H56A	1.0858	0.6382	0.1762	0.040*
C11B	1.23715 (18)	0.2329 (3)	0.15439 (5)	0.0304 (5)
C12B	1.16226 (19)	0.2218 (3)	0.17298 (5)	0.0337 (6)
H12B	1.0981	0.1773	0.1639	0.040*
C13B	1.1797 (2)	0.2747 (4)	0.20446 (5)	0.0418 (7)
H13B	1.1277	0.2659	0.2168	0.050*
C14B	1.2732 (2)	0.3407 (4)	0.21809 (6)	0.0465 (7)
H14B	1.2849	0.3792	0.2396	0.056*
C15B	1.3488 (2)	0.3497 (4)	0.20014 (6)	0.0464 (7)
H15B	1.4130	0.3928	0.2094	0.056*
C16B	1.33127 (19)	0.2963 (4)	0.16878 (6)	0.0385 (6)
H16B	1.3841	0.3027	0.1567	0.046*
C21B	1.21749 (17)	0.1790 (3)	0.12044 (5)	0.0278 (5)
C22B	1.12411 (17)	0.2146 (3)	0.10239 (5)	0.0272 (5)
H22B	1.0748	0.2758	0.1121	0.033*
C23B	1.10068 (17)	0.1635 (3)	0.07061 (5)	0.0276 (5)
C24B	1.17384 (19)	0.0753 (3)	0.05660 (5)	0.0335 (6)
H24B	1.1597	0.0389	0.0350	0.040*
C25B	1.26747 (19)	0.0403 (4)	0.07411 (6)	0.0351 (6)
H25B	1.3169	−0.0201	0.0643	0.042*
C26B	1.28958 (18)	0.0923 (3)	0.10552 (5)	0.0329 (5)
H26B	1.3542	0.0689	0.1171	0.039*
C31B	0.99907 (18)	0.2009 (3)	0.05315 (5)	0.0286 (5)
C32B	0.91739 (17)	0.1939 (3)	0.06889 (5)	0.0259 (5)
H32B	0.9279	0.1582	0.0905	0.031*
C33B	0.82084 (18)	0.2366 (3)	0.05441 (5)	0.0285 (5)
C34B	0.8064 (2)	0.2864 (3)	0.02240 (5)	0.0356 (6)
H34B	0.7415	0.3178	0.0118	0.043*
C35B	0.8863 (2)	0.2897 (4)	0.00617 (5)	0.0404 (7)
H35B	0.8754	0.3206	−0.0157	0.048*
C36B	0.9814 (2)	0.2493 (4)	0.02097 (5)	0.0365 (6)
H36B	1.0354	0.2542	0.0094	0.044*
C41B	0.73715 (17)	0.2329 (3)	0.07294 (5)	0.0283 (5)
C42B	0.75414 (17)	0.2748 (3)	0.10511 (5)	0.0273 (5)
H42B	0.8198	0.3068	0.1149	0.033*
C43B	0.67802 (17)	0.2713 (3)	0.12340 (5)	0.0300 (5)
C44B	0.58204 (19)	0.2254 (4)	0.10854 (6)	0.0375 (6)
H44B	0.5288	0.2225	0.1205	0.045*
C45B	0.56377 (19)	0.1843 (4)	0.07672 (6)	0.0396 (6)
H45B	0.4979	0.1538	0.0669	0.048*
C46B	0.63964 (18)	0.1867 (4)	0.05895 (5)	0.0342 (6)
H46B	0.6259	0.1569	0.0371	0.041*
C51B	0.69879 (17)	0.3198 (4)	0.15763 (5)	0.0311 (5)
C52B	0.76721 (18)	0.4578 (4)	0.16903 (5)	0.0331 (6)
H52B	0.8021	0.5211	0.1547	0.040*
C53B	0.7855 (2)	0.5049 (4)	0.20080 (5)	0.0415 (6)
H53B	0.8321	0.6003	0.2080	0.050*
C54B	0.7358 (2)	0.4127 (4)	0.22196 (6)	0.0470 (7)
H54B	0.7477	0.4449	0.2438	0.056*
C55B	0.6686 (2)	0.2728 (4)	0.21110 (6)	0.0477 (7)
H55B	0.6347	0.2085	0.2256	0.057*
C56B	0.6506 (2)	0.2261 (4)	0.17936 (6)	0.0405 (6)
H56B	0.6048	0.1291	0.1723	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11A	0.0309 (12)	0.0237 (13)	0.0284 (11)	−0.0015 (10)	0.0065 (9)	0.0036 (9)
C12A	0.0314 (13)	0.0375 (15)	0.0325 (12)	−0.0010 (11)	0.0042 (10)	0.0000 (11)
C13A	0.0428 (15)	0.0443 (17)	0.0331 (13)	−0.0040 (13)	−0.0011 (11)	−0.0004 (11)
C14A	0.0567 (17)	0.0425 (17)	0.0272 (12)	−0.0016 (14)	0.0094 (12)	−0.0011 (11)
C15A	0.0484 (15)	0.0392 (16)	0.0348 (13)	0.0080 (13)	0.0177 (11)	0.0064 (11)
C16A	0.0335 (13)	0.0297 (14)	0.0342 (12)	0.0018 (11)	0.0064 (10)	0.0067 (10)
C21A	0.0249 (11)	0.0191 (12)	0.0305 (11)	0.0018 (9)	0.0004 (9)	0.0034 (9)
C22A	0.0239 (11)	0.0240 (13)	0.0290 (11)	0.0006 (10)	−0.0002 (9)	−0.0001 (9)
C23A	0.0277 (12)	0.0209 (12)	0.0270 (11)	0.0035 (10)	−0.0014 (9)	0.0013 (9)
C24A	0.0336 (13)	0.0265 (13)	0.0286 (11)	0.0009 (10)	−0.0041 (9)	−0.0014 (10)
C25A	0.0268 (12)	0.0269 (13)	0.0405 (13)	−0.0013 (10)	−0.0048 (10)	0.0000 (10)
C26A	0.0262 (11)	0.0248 (13)	0.0353 (12)	0.0006 (10)	0.0021 (9)	0.0050 (10)
C31A	0.0345 (12)	0.0223 (12)	0.0233 (10)	0.0005 (10)	0.0014 (9)	−0.0034 (9)
C32A	0.0340 (12)	0.0220 (12)	0.0168 (9)	0.0017 (10)	0.0037 (8)	0.0003 (8)
C33A	0.0373 (13)	0.0199 (12)	0.0221 (10)	0.0022 (10)	0.0080 (9)	0.0005 (8)
C34A	0.0445 (14)	0.0295 (14)	0.0206 (10)	0.0008 (11)	0.0107 (10)	−0.0007 (9)
C35A	0.0534 (15)	0.0365 (16)	0.0185 (11)	0.0011 (13)	0.0043 (10)	0.0009 (10)
C36A	0.0382 (13)	0.0340 (14)	0.0222 (11)	0.0008 (11)	−0.0046 (9)	0.0005 (9)
C41A	0.0329 (12)	0.0191 (12)	0.0240 (10)	0.0005 (10)	0.0094 (9)	0.0032 (8)
C42A	0.0302 (11)	0.0224 (12)	0.0249 (10)	0.0006 (10)	0.0088 (9)	0.0031 (9)
C43A	0.0310 (12)	0.0218 (12)	0.0269 (11)	−0.0013 (10)	0.0052 (9)	0.0032 (9)
C44A	0.0254 (11)	0.0325 (14)	0.0346 (12)	−0.0008 (11)	0.0041 (9)	0.0019 (10)
C45A	0.0322 (13)	0.0345 (14)	0.0376 (13)	0.0029 (11)	0.0161 (10)	0.0011 (11)
C46A	0.0405 (14)	0.0277 (13)	0.0278 (11)	−0.0008 (11)	0.0154 (10)	−0.0001 (10)
C51A	0.0268 (11)	0.0282 (13)	0.0300 (11)	−0.0040 (10)	0.0035 (9)	0.0015 (10)
C52A	0.0326 (13)	0.0360 (15)	0.0291 (12)	0.0054 (11)	0.0020 (9)	−0.0015 (10)
C53A	0.0434 (15)	0.0498 (18)	0.0330 (13)	0.0016 (13)	0.0055 (11)	−0.0103 (12)
C54A	0.0519 (16)	0.0514 (18)	0.0258 (12)	−0.0068 (14)	0.0010 (11)	−0.0051 (11)
C55A	0.0390 (14)	0.0443 (17)	0.0323 (12)	−0.0024 (13)	−0.0056 (11)	0.0062 (11)
C56A	0.0333 (13)	0.0313 (14)	0.0354 (12)	−0.0008 (11)	0.0022 (10)	0.0021 (10)
C11B	0.0323 (12)	0.0234 (13)	0.0348 (12)	−0.0012 (10)	0.0030 (10)	0.0081 (10)
C12B	0.0356 (13)	0.0303 (14)	0.0343 (12)	0.0030 (11)	0.0033 (10)	0.0018 (10)
C13B	0.0531 (16)	0.0390 (17)	0.0328 (13)	0.0066 (13)	0.0049 (12)	0.0049 (11)
C14B	0.069 (2)	0.0340 (16)	0.0307 (13)	0.0040 (14)	−0.0096 (13)	0.0015 (11)
C15B	0.0513 (17)	0.0342 (16)	0.0470 (15)	−0.0056 (14)	−0.0120 (12)	0.0093 (12)
C16B	0.0375 (14)	0.0322 (15)	0.0433 (14)	−0.0026 (12)	−0.0014 (11)	0.0108 (11)
C21B	0.0308 (12)	0.0206 (12)	0.0336 (12)	−0.0035 (10)	0.0097 (9)	0.0065 (9)
C22B	0.0323 (12)	0.0224 (13)	0.0288 (11)	−0.0011 (10)	0.0106 (9)	0.0020 (9)
C23B	0.0353 (13)	0.0213 (12)	0.0283 (11)	−0.0022 (10)	0.0112 (9)	0.0011 (9)
C24B	0.0460 (14)	0.0239 (13)	0.0343 (12)	−0.0038 (11)	0.0176 (11)	0.0008 (10)
C25B	0.0393 (14)	0.0256 (14)	0.0454 (14)	0.0043 (11)	0.0215 (11)	0.0066 (11)
C26B	0.0302 (12)	0.0256 (14)	0.0449 (14)	0.0016 (11)	0.0121 (10)	0.0072 (10)
C31B	0.0416 (13)	0.0201 (12)	0.0249 (11)	−0.0017 (10)	0.0083 (9)	−0.0007 (9)
C32B	0.0359 (12)	0.0207 (12)	0.0197 (10)	−0.0023 (10)	0.0003 (9)	0.0018 (8)
C33B	0.0368 (13)	0.0199 (12)	0.0269 (11)	−0.0018 (10)	−0.0004 (9)	−0.0022 (9)
C34B	0.0478 (15)	0.0308 (15)	0.0246 (11)	−0.0001 (12)	−0.0050 (10)	−0.0012 (10)
C35B	0.0599 (17)	0.0397 (17)	0.0201 (11)	−0.0001 (13)	0.0023 (11)	−0.0003 (10)
C36B	0.0523 (16)	0.0337 (15)	0.0251 (11)	−0.0008 (12)	0.0113 (11)	−0.0014 (10)
C41B	0.0321 (12)	0.0186 (12)	0.0312 (11)	0.0019 (10)	−0.0042 (9)	0.0035 (9)
C42B	0.0267 (11)	0.0226 (13)	0.0313 (11)	0.0012 (10)	0.0006 (9)	0.0024 (9)
C43B	0.0293 (12)	0.0219 (13)	0.0380 (12)	0.0010 (10)	0.0031 (10)	0.0033 (10)
C44B	0.0276 (12)	0.0273 (14)	0.0579 (16)	0.0022 (11)	0.0074 (11)	0.0018 (11)
C45B	0.0261 (13)	0.0309 (15)	0.0566 (16)	−0.0004 (11)	−0.0094 (11)	−0.0031 (12)
C46B	0.0330 (13)	0.0285 (14)	0.0370 (13)	0.0028 (11)	−0.0069 (10)	−0.0018 (10)
C51B	0.0282 (12)	0.0288 (14)	0.0381 (12)	0.0048 (11)	0.0109 (10)	0.0047 (10)
C52B	0.0326 (13)	0.0359 (15)	0.0318 (12)	0.0023 (11)	0.0087 (10)	0.0035 (10)
C53B	0.0414 (15)	0.0477 (17)	0.0358 (13)	0.0022 (13)	0.0074 (11)	−0.0030 (11)
C54B	0.0562 (17)	0.0526 (19)	0.0347 (13)	0.0138 (15)	0.0149 (12)	0.0055 (13)
C55B	0.0569 (18)	0.0451 (18)	0.0478 (15)	0.0113 (15)	0.0284 (14)	0.0117 (13)
C56B	0.0411 (15)	0.0351 (16)	0.0501 (15)	0.0030 (12)	0.0216 (12)	0.0061 (12)

Geometric parameters (Å, º)

C11A—C16A	1.394 (3)	C11B—C12B	1.391 (3)
C11A—C12A	1.397 (3)	C11B—C16B	1.402 (3)
C11A—C21A	1.490 (3)	C11B—C21B	1.487 (3)
C12A—C13A	1.383 (3)	C12B—C13B	1.384 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.384 (4)	C13B—C14B	1.393 (4)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.381 (4)	C14B—C15B	1.379 (4)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.381 (3)	C15B—C16B	1.380 (4)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9500	C16B—H16B	0.9500
C21A—C22A	1.394 (3)	C21B—C22B	1.398 (3)
C21A—C26A	1.398 (3)	C21B—C26B	1.398 (3)
C22A—C23A	1.392 (3)	C22B—C23B	1.396 (3)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—C24A	1.398 (3)	C23B—C24B	1.393 (3)
C23A—C31A	1.484 (3)	C23B—C31B	1.484 (3)
C24A—C25A	1.386 (3)	C24B—C25B	1.390 (3)
C24A—H24A	0.9500	C24B—H24B	0.9500
C25A—C26A	1.379 (3)	C25B—C26B	1.382 (3)
C25A—H25A	0.9500	C25B—H25B	0.9500
C26A—H26A	0.9500	C26B—H26B	0.9500
C31A—C32A	1.391 (3)	C31B—C32B	1.388 (3)
C31A—C36A	1.397 (3)	C31B—C36B	1.404 (3)
C32A—C33A	1.395 (3)	C32B—C33B	1.391 (3)
C32A—H32A	0.9500	C32B—H32B	0.9500
C33A—C34A	1.403 (3)	C33B—C34B	1.400 (3)
C33A—C41A	1.486 (3)	C33B—C41B	1.487 (3)
C34A—C35A	1.384 (3)	C34B—C35B	1.380 (4)
C34A—H34A	0.9500	C34B—H34B	0.9500
C35A—C36A	1.382 (3)	C35B—C36B	1.374 (4)
C35A—H35A	0.9500	C35B—H35B	0.9500
C36A—H36A	0.9500	C36B—H36B	0.9500
C41A—C46A	1.397 (3)	C41B—C42B	1.393 (3)
C41A—C42A	1.401 (3)	C41B—C46B	1.402 (3)
C42A—C43A	1.395 (3)	C42B—C43B	1.394 (3)
C42A—H42A	0.9500	C42B—H42B	0.9500
C43A—C44A	1.390 (3)	C43B—C44B	1.394 (3)
C43A—C51A	1.487 (3)	C43B—C51B	1.489 (3)
C44A—C45A	1.383 (3)	C44B—C45B	1.377 (3)
C44A—H44A	0.9500	C44B—H44B	0.9500
C45A—C46A	1.379 (3)	C45B—C46B	1.376 (4)
C45A—H45A	0.9500	C45B—H45B	0.9500
C46A—H46A	0.9500	C46B—H46B	0.9500
C51A—C56A	1.393 (3)	C51B—C52B	1.392 (3)
C51A—C52A	1.396 (3)	C51B—C56B	1.394 (3)
C52A—C53A	1.386 (3)	C52B—C53B	1.385 (3)
C52A—H52A	0.9500	C52B—H52B	0.9500
C53A—C54A	1.385 (4)	C53B—C54B	1.383 (4)
C53A—H53A	0.9500	C53B—H53B	0.9500
C54A—C55A	1.379 (4)	C54B—C55B	1.386 (4)
C54A—H54A	0.9500	C54B—H54B	0.9500
C55A—C56A	1.389 (3)	C55B—C56B	1.383 (4)
C55A—H55A	0.9500	C55B—H55B	0.9500
C56A—H56A	0.9500	C56B—H56B	0.9500
C16A—C11A—C12A	117.9 (2)	C12B—C11B—C16B	117.7 (2)
C16A—C11A—C21A	121.3 (2)	C12B—C11B—C21B	120.8 (2)
C12A—C11A—C21A	120.8 (2)	C16B—C11B—C21B	121.4 (2)
C13A—C12A—C11A	121.1 (2)	C13B—C12B—C11B	121.1 (2)
C13A—C12A—H12A	119.5	C13B—C12B—H12B	119.5
C11A—C12A—H12A	119.5	C11B—C12B—H12B	119.5
C12A—C13A—C14A	120.1 (2)	C12B—C13B—C14B	120.2 (3)
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.9
C14A—C13A—H13A	119.9	C14B—C13B—H13B	119.9
C15A—C14A—C13A	119.4 (2)	C15B—C14B—C13B	119.5 (2)
C15A—C14A—H14A	120.3	C15B—C14B—H14B	120.3
C13A—C14A—H14A	120.3	C13B—C14B—H14B	120.3
C16A—C15A—C14A	120.6 (2)	C14B—C15B—C16B	120.2 (3)
C16A—C15A—H15A	119.7	C14B—C15B—H15B	119.9
C14A—C15A—H15A	119.7	C16B—C15B—H15B	119.9
C15A—C16A—C11A	120.9 (2)	C15B—C16B—C11B	121.3 (2)
C15A—C16A—H16A	119.5	C15B—C16B—H16B	119.3
C11A—C16A—H16A	119.5	C11B—C16B—H16B	119.3
C22A—C21A—C26A	118.09 (19)	C22B—C21B—C26B	117.9 (2)
C22A—C21A—C11A	119.79 (19)	C22B—C21B—C11B	119.8 (2)
C26A—C21A—C11A	122.12 (19)	C26B—C21B—C11B	122.3 (2)
C23A—C22A—C21A	121.9 (2)	C23B—C22B—C21B	122.3 (2)
C23A—C22A—H22A	119.0	C23B—C22B—H22B	118.8
C21A—C22A—H22A	119.0	C21B—C22B—H22B	118.8
C22A—C23A—C24A	118.6 (2)	C24B—C23B—C22B	118.3 (2)
C22A—C23A—C31A	119.44 (19)	C24B—C23B—C31B	122.3 (2)
C24A—C23A—C31A	121.94 (19)	C22B—C23B—C31B	119.40 (19)
C25A—C24A—C23A	120.0 (2)	C25B—C24B—C23B	120.2 (2)
C25A—C24A—H24A	120.0	C25B—C24B—H24B	119.9
C23A—C24A—H24A	120.0	C23B—C24B—H24B	119.9
C26A—C25A—C24A	120.7 (2)	C26B—C25B—C24B	120.8 (2)
C26A—C25A—H25A	119.7	C26B—C25B—H25B	119.6
C24A—C25A—H25A	119.7	C24B—C25B—H25B	119.6
C25A—C26A—C21A	120.7 (2)	C25B—C26B—C21B	120.5 (2)
C25A—C26A—H26A	119.7	C25B—C26B—H26B	119.8
C21A—C26A—H26A	119.7	C21B—C26B—H26B	119.8
C32A—C31A—C36A	117.8 (2)	C32B—C31B—C36B	117.5 (2)
C32A—C31A—C23A	119.41 (17)	C32B—C31B—C23B	119.94 (18)
C36A—C31A—C23A	122.8 (2)	C36B—C31B—C23B	122.5 (2)
C31A—C32A—C33A	122.98 (18)	C31B—C32B—C33B	122.97 (19)
C31A—C32A—H32A	118.5	C31B—C32B—H32B	118.5
C33A—C32A—H32A	118.5	C33B—C32B—H32B	118.5
C32A—C33A—C34A	117.4 (2)	C32B—C33B—C34B	117.8 (2)
C32A—C33A—C41A	120.76 (17)	C32B—C33B—C41B	120.25 (18)
C34A—C33A—C41A	121.83 (19)	C34B—C33B—C41B	121.9 (2)
C35A—C34A—C33A	120.5 (2)	C35B—C34B—C33B	120.0 (2)
C35A—C34A—H34A	119.8	C35B—C34B—H34B	120.0
C33A—C34A—H34A	119.8	C33B—C34B—H34B	120.0
C36A—C35A—C34A	120.77 (19)	C36B—C35B—C34B	121.3 (2)
C36A—C35A—H35A	119.6	C36B—C35B—H35B	119.3
C34A—C35A—H35A	119.6	C34B—C35B—H35B	119.3
C35A—C36A—C31A	120.5 (2)	C35B—C36B—C31B	120.3 (2)
C35A—C36A—H36A	119.8	C35B—C36B—H36B	119.9
C31A—C36A—H36A	119.8	C31B—C36B—H36B	119.9
C46A—C41A—C42A	117.6 (2)	C42B—C41B—C46B	117.9 (2)
C46A—C41A—C33A	121.90 (18)	C42B—C41B—C33B	120.3 (2)
C42A—C41A—C33A	120.53 (18)	C46B—C41B—C33B	121.73 (19)
C43A—C42A—C41A	122.1 (2)	C41B—C42B—C43B	122.2 (2)
C43A—C42A—H42A	118.9	C41B—C42B—H42B	118.9
C41A—C42A—H42A	118.9	C43B—C42B—H42B	118.9
C44A—C43A—C42A	118.21 (19)	C42B—C43B—C44B	118.0 (2)
C44A—C43A—C51A	120.8 (2)	C42B—C43B—C51B	120.6 (2)
C42A—C43A—C51A	121.01 (19)	C44B—C43B—C51B	121.3 (2)
C45A—C44A—C43A	120.7 (2)	C45B—C44B—C43B	120.6 (2)
C45A—C44A—H44A	119.7	C45B—C44B—H44B	119.7
C43A—C44A—H44A	119.7	C43B—C44B—H44B	119.7
C46A—C45A—C44A	120.4 (2)	C46B—C45B—C44B	120.9 (2)
C46A—C45A—H45A	119.8	C46B—C45B—H45B	119.6
C44A—C45A—H45A	119.8	C44B—C45B—H45B	119.6
C45A—C46A—C41A	121.0 (2)	C45B—C46B—C41B	120.4 (2)
C45A—C46A—H46A	119.5	C45B—C46B—H46B	119.8
C41A—C46A—H46A	119.5	C41B—C46B—H46B	119.8
C56A—C51A—C52A	118.0 (2)	C52B—C51B—C56B	117.9 (2)
C56A—C51A—C43A	120.5 (2)	C52B—C51B—C43B	121.5 (2)
C52A—C51A—C43A	121.5 (2)	C56B—C51B—C43B	120.7 (2)
C53A—C52A—C51A	121.1 (2)	C53B—C52B—C51B	121.5 (2)
C53A—C52A—H52A	119.5	C53B—C52B—H52B	119.2
C51A—C52A—H52A	119.5	C51B—C52B—H52B	119.2
C54A—C53A—C52A	120.0 (2)	C54B—C53B—C52B	119.8 (3)
C54A—C53A—H53A	120.0	C54B—C53B—H53B	120.1
C52A—C53A—H53A	120.0	C52B—C53B—H53B	120.1
C55A—C54A—C53A	119.7 (2)	C53B—C54B—C55B	119.4 (2)
C55A—C54A—H54A	120.1	C53B—C54B—H54B	120.3
C53A—C54A—H54A	120.1	C55B—C54B—H54B	120.3
C54A—C55A—C56A	120.3 (2)	C56B—C55B—C54B	120.6 (2)
C54A—C55A—H55A	119.9	C56B—C55B—H55B	119.7
C56A—C55A—H55A	119.9	C54B—C55B—H55B	119.7
C55A—C56A—C51A	120.9 (2)	C55B—C56B—C51B	120.7 (3)
C55A—C56A—H56A	119.5	C55B—C56B—H56B	119.6
C51A—C56A—H56A	119.5	C51B—C56B—H56B	119.6
C16A—C11A—C12A—C13A	−1.0 (4)	C16B—C11B—C12B—C13B	1.1 (4)
C21A—C11A—C12A—C13A	177.8 (2)	C21B—C11B—C12B—C13B	−178.9 (2)
C11A—C12A—C13A—C14A	−0.8 (4)	C11B—C12B—C13B—C14B	0.2 (4)
C12A—C13A—C14A—C15A	2.2 (4)	C12B—C13B—C14B—C15B	−1.2 (4)
C13A—C14A—C15A—C16A	−1.7 (4)	C13B—C14B—C15B—C16B	1.0 (4)
C14A—C15A—C16A—C11A	−0.1 (4)	C14B—C15B—C16B—C11B	0.3 (4)
C12A—C11A—C16A—C15A	1.5 (4)	C12B—C11B—C16B—C15B	−1.3 (4)
C21A—C11A—C16A—C15A	−177.4 (2)	C21B—C11B—C16B—C15B	178.7 (2)
C16A—C11A—C21A—C22A	142.8 (2)	C12B—C11B—C21B—C22B	35.2 (3)
C12A—C11A—C21A—C22A	−36.0 (3)	C16B—C11B—C21B—C22B	−144.8 (2)
C16A—C11A—C21A—C26A	−36.7 (3)	C12B—C11B—C21B—C26B	−144.7 (2)
C12A—C11A—C21A—C26A	144.5 (2)	C16B—C11B—C21B—C26B	35.3 (3)
C26A—C21A—C22A—C23A	−1.5 (3)	C26B—C21B—C22B—C23B	1.3 (3)
C11A—C21A—C22A—C23A	178.9 (2)	C11B—C21B—C22B—C23B	−178.6 (2)
C21A—C22A—C23A—C24A	1.5 (3)	C21B—C22B—C23B—C24B	−0.5 (3)
C21A—C22A—C23A—C31A	−177.2 (2)	C21B—C22B—C23B—C31B	178.3 (2)
C22A—C23A—C24A—C25A	−0.5 (3)	C22B—C23B—C24B—C25B	−0.1 (3)
C31A—C23A—C24A—C25A	178.1 (2)	C31B—C23B—C24B—C25B	−178.8 (2)
C23A—C24A—C25A—C26A	−0.3 (4)	C23B—C24B—C25B—C26B	−0.1 (4)
C24A—C25A—C26A—C21A	0.2 (4)	C24B—C25B—C26B—C21B	0.9 (4)
C22A—C21A—C26A—C25A	0.7 (3)	C22B—C21B—C26B—C25B	−1.4 (3)
C11A—C21A—C26A—C25A	−179.8 (2)	C11B—C21B—C26B—C25B	178.4 (2)
C22A—C23A—C31A—C32A	32.0 (3)	C24B—C23B—C31B—C32B	145.9 (2)
C24A—C23A—C31A—C32A	−146.6 (2)	C22B—C23B—C31B—C32B	−32.8 (3)
C22A—C23A—C31A—C36A	−147.7 (2)	C24B—C23B—C31B—C36B	−36.0 (4)
C24A—C23A—C31A—C36A	33.7 (4)	C22B—C23B—C31B—C36B	145.3 (2)
C36A—C31A—C32A—C33A	2.2 (3)	C36B—C31B—C32B—C33B	−1.6 (3)
C23A—C31A—C32A—C33A	−177.5 (2)	C23B—C31B—C32B—C33B	176.6 (2)
C31A—C32A—C33A—C34A	−1.2 (3)	C31B—C32B—C33B—C34B	0.9 (3)
C31A—C32A—C33A—C41A	178.2 (2)	C31B—C32B—C33B—C41B	−177.8 (2)
C32A—C33A—C34A—C35A	−0.7 (3)	C32B—C33B—C34B—C35B	0.7 (4)
C41A—C33A—C34A—C35A	179.9 (2)	C41B—C33B—C34B—C35B	179.4 (2)
C33A—C34A—C35A—C36A	1.4 (4)	C33B—C34B—C35B—C36B	−1.6 (4)
C34A—C35A—C36A—C31A	−0.3 (4)	C34B—C35B—C36B—C31B	0.9 (4)
C32A—C31A—C36A—C35A	−1.5 (4)	C32B—C31B—C36B—C35B	0.7 (3)
C23A—C31A—C36A—C35A	178.2 (2)	C23B—C31B—C36B—C35B	−177.4 (2)
C32A—C33A—C41A—C46A	147.7 (2)	C32B—C33B—C41B—C42B	30.6 (3)
C34A—C33A—C41A—C46A	−32.9 (3)	C34B—C33B—C41B—C42B	−148.1 (2)
C32A—C33A—C41A—C42A	−31.6 (3)	C32B—C33B—C41B—C46B	−149.1 (2)
C34A—C33A—C41A—C42A	147.7 (2)	C34B—C33B—C41B—C46B	32.3 (3)
C46A—C41A—C42A—C43A	−0.2 (3)	C46B—C41B—C42B—C43B	0.2 (3)
C33A—C41A—C42A—C43A	179.2 (2)	C33B—C41B—C42B—C43B	−179.4 (2)
C41A—C42A—C43A—C44A	1.1 (3)	C41B—C42B—C43B—C44B	−0.5 (4)
C41A—C42A—C43A—C51A	−179.1 (2)	C41B—C42B—C43B—C51B	−179.1 (2)
C42A—C43A—C44A—C45A	−1.1 (3)	C42B—C43B—C44B—C45B	0.3 (4)
C51A—C43A—C44A—C45A	179.1 (2)	C51B—C43B—C44B—C45B	178.8 (2)
C43A—C44A—C45A—C46A	0.1 (4)	C43B—C44B—C45B—C46B	0.3 (4)
C44A—C45A—C46A—C41A	0.9 (4)	C44B—C45B—C46B—C41B	−0.6 (4)
C42A—C41A—C46A—C45A	−0.8 (4)	C42B—C41B—C46B—C45B	0.3 (4)
C33A—C41A—C46A—C45A	179.8 (2)	C33B—C41B—C46B—C45B	179.9 (2)
C44A—C43A—C51A—C56A	−34.2 (3)	C42B—C43B—C51B—C52B	35.9 (3)
C42A—C43A—C51A—C56A	146.1 (2)	C44B—C43B—C51B—C52B	−142.6 (3)
C44A—C43A—C51A—C52A	145.5 (2)	C42B—C43B—C51B—C56B	−143.4 (2)
C42A—C43A—C51A—C52A	−34.3 (3)	C44B—C43B—C51B—C56B	38.1 (3)
C56A—C51A—C52A—C53A	0.3 (4)	C56B—C51B—C52B—C53B	−1.6 (4)
C43A—C51A—C52A—C53A	−179.4 (2)	C43B—C51B—C52B—C53B	179.1 (2)
C51A—C52A—C53A—C54A	−0.1 (4)	C51B—C52B—C53B—C54B	0.6 (4)
C52A—C53A—C54A—C55A	0.2 (4)	C52B—C53B—C54B—C55B	0.5 (4)
C53A—C54A—C55A—C56A	−0.5 (4)	C53B—C54B—C55B—C56B	−0.4 (4)
C54A—C55A—C56A—C51A	0.7 (4)	C54B—C55B—C56B—C51B	−0.6 (4)
C52A—C51A—C56A—C55A	−0.5 (4)	C52B—C51B—C56B—C55B	1.6 (4)
C43A—C51A—C56A—C55A	179.1 (2)	C43B—C51B—C56B—C55B	−179.0 (2)