Redetermination of the trigonal prismatic complex tris­(cis-1,2-diphenyl­ethyl­ene-1,2-dithiol­ato)rhenium

The first trigonal prismatic mol­ecular compound characterized by single-crystal X-ray diffraction, [Re(C₁₄H₁₀S₂)₃], has been redetermined using modern laboratory equipment. The new experiment reaffirms the results of the original. Since then, numerous tris-dithiol­ene complexes have been structurally characterized, having geometries ranging from trigonal prismatic to nearly octa­hedral. An examination of the coordination geometries of these structures is included.

S1. Comment

Forty years ago, the first example of trigonal prismatic coordination in discrete metal complexes was reported (Eisenberg & Ibers, 1966). The particular example was the rhenium–tris-dithiolene complex (I), first reported by Schrauzer et al. (1964). A number of other tris-dithiolene complexes were subsequently studied structurally and found to possess coordination geometries ranging from trigonal prismatic (TP) to nearly octahedral (O), depending on the metal ion, overall complex charge and dithiolene substituent (Brown & Stiefel, 1973; Colmanet & Mackay, 1988; Yang et al., 1991; Matsubayashi et al., 1992, 1993; Goddard & Holm, 1999; Wang et al., 1999; Lewis & Dance, 2000; Lim et al., 2000; Fomitchev et al., 2001).

The specific structure determination of (I), while widely cited as the first example of TP coordination, was based on intensity data collected by methods that would be viewed today as substandard (manually positioned crystal and detector, and fixed stationary counting times) and led to a number of problems in the refinement of the structure. Specifically, because of reflection overlap in the counter window, a significant fraction of the intensity data was eliminated from the refinement, leading to a low ratio of observations to variables, the use of isotropic displacement parameters for all atoms and group refinement procedures for the six phenyl rings. While the final refinement of the structure converged to R values of 0.069 and 0.079, a wide range of C—S distances was noted and standard deviations in all metrical parameters were substantial.

In this paper, we report a redetermination of the structure of (I) using a crystal from the originally prepared sample and performed using state-of-the-art CCD instrumentation. Additionally, we tabulate a simple distortion parameter that allows one to assess the six-coordination geometry from TP to O more accurately for tris-dithiolene-chelated complexes.

The structure redetermination confirms the TP coordination geometry of (I) as originally reported. As expected, in the present determination the equivalent metrical parameters for the complex exhibit much better agreement and much smaller standard deviations than in the original report. For example, Re—S distances cover a range of 2.3274 (9)–2.3348 (10) Å and average 2.3322 (22) Å, while dithiolene S—C distances exhibit a range of 1.715 (4)–1.730 (4) Å and average 1.725 Å (10) Å. The latter numbers compare with 1.62 (4)–1.75 (3) Å and 1.69 (8) Å, respectively, in the initial report.

The crystal structure consists of the packing of neutral molecules with no notably short intermolecular contacts. A feature of the packing is that the molecules stack so that the stacking direction deviates by only 10.2° from the trigonal axis of the complex.

Studies on related dithiolene complexes following the initial report revealed that the tris-chelated complexes with MS₆ coordination environments exhibited a range of coordination geometries from purely TP to distorted O that have been analyzed by Stiefel & Brown (1972). If one calculates the position of the centroid (Cen) of the three S atoms in each trigonal face then it is possible to define a TP distortion as the dihedral angle formed by S_upper—Cen_upper—Cen_lower—S_lower, where upper and lower refer to the two trigonal faces and S_upper and S_lower on the respective trigonal faces belong to the same ligand (Fig. 2). Each structure will therefore yield three distortion angles that can be averaged. For a pure trigonal prism the distortion angle would be 0°, and for an intermediate geometry half-way to O it would be 30° (ligand distance constraints preclude achieving a pure D₃ geometry with O angles). Table 1 contains a tabulation of the tris-dithiolene structures from the Cambridge Structural Database (Version 5.27; Allen, 2002), and their TP distortion angles as defined above. As can be seen, compound (I) has one of the smallest distortion angles for structures in which TP symmetry is not crystallographically imposed. Increasing negative charge on the tris-dithiolene complexes moves the coordination geometry towards O with an increasing distortion angle. A possible explanation for this effect is minimization of interligand repulsions as the donor atoms acquire greater negative charge [see Brown & Stiefel (1973) for a detailed discussion].

Brown & Stiefel (1973) propose a second distortion parameter in analyzing TP coordination. The parameter involves the ratio s/h, where s is the nearest interligand S···S contact and h is the distance between the two parallel trigonal faces. For TP, the s/h ratio is 1.0, meaning that the sides of the prism are squares, whereas for O, the ratio is 1.22 [= (3/2)^1/2; Stiefel & Brown, 1972]. In the case of (I), with S···S contacts averaging 3.054 (31) and 3.055 (23) Å, respectively, for intra-triangular and intra-ligand values, the s/h ratio is 1.0, the sides of the prism are square and the coordination geometry is truly undistorted TP.

Finally, it is reassuring how good the overall agreement is between the original structure determination and the more accurate and precise current determination given the quality of the earlier intensity measurements.

S2. Experimental

The material used was the original sample kindly supplied by Professor Schrauzer in the mid-1960 s.

S3. Refinement

The current standard setting differs from the original cell setting, which was chosen arbitrarily based on preliminary precession photographs (Eisenberg & Ibers, 1966), by the transformation, [0 0 1 / 0 1 1 / 1 0 1]. H atoms were placed geometrically and refined with relative isotropic displacement parameters. The maximum residual peak and hole from the final difference map, located 0.86 and 0.82 Å from the Re atom, respectively, are probably a result of residual absorption or Fourier termination errors.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A displacement ellipsoid (50% probability) drawing of (I), with H atoms omitted. Inset: The view down the trigonal axis.
	Fig. 2. The dihedral (trigonal distortion) angle.

tris(cis-1,2-diphenylethylene-1,2-dithiolato)rhenium

Crystal data

[Re(C14H10S2)3]	Z = 2
Mr = 913.22	F(000) = 906
Triclinic, P1	Dx = 1.621 Mg m^−3
a = 9.7949 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8765 (10) Å	Cell parameters from 3785 reflections
c = 19.4517 (17) Å	θ = 2.5–29.8°
α = 80.190 (1)°	µ = 3.61 mm^−1
β = 76.770 (1)°	T = 100 K
γ = 68.758 (1)°	Plate, red–black
V = 1871.5 (3) Å^3	0.28 × 0.24 × 0.06 mm

Data collection

Bruker SMART APEXII CCD Platform diffractometer	10391 independent reflections
Radiation source: fine-focus sealed tube	8772 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
area detector, ω scans per ϕ	θmax = 29.6°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −13→13
Tmin = 0.376, Tmax = 0.806	k = −15→15
27614 measured reflections	l = −26→26

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 1.2114P] where P = (Fo^2 + 2Fc^2)/3
10391 reflections	(Δ/σ)max = 0.004
442 parameters	Δρmax = 3.47 e Å^−3
0 restraints	Δρmin = −3.08 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
Re1	0.254904 (16)	1.019838 (15)	0.751297 (7)	0.01623 (5)
S1	0.48220 (10)	0.91538 (9)	0.68108 (4)	0.01862 (18)
S2	0.16413 (10)	0.96149 (10)	0.66519 (5)	0.01968 (18)
S3	0.37656 (10)	0.91753 (9)	0.84653 (5)	0.01926 (18)
S4	0.06729 (10)	0.94867 (10)	0.82400 (4)	0.01960 (18)
S5	0.38625 (10)	1.16101 (9)	0.75080 (5)	0.01905 (18)
S6	0.05952 (10)	1.22040 (9)	0.74214 (5)	0.01943 (18)
C1	0.4533 (4)	0.8560 (4)	0.61070 (18)	0.0192 (7)
C2	0.3113 (4)	0.8744 (4)	0.60486 (18)	0.0194 (7)
C3	0.2599 (4)	0.8589 (4)	0.91369 (18)	0.0198 (7)
C4	0.1243 (4)	0.8671 (4)	0.90224 (18)	0.0197 (7)
C5	0.2699 (4)	1.3225 (4)	0.74354 (17)	0.0178 (7)
C6	0.1236 (4)	1.3496 (4)	0.74140 (18)	0.0190 (7)
C7	0.5896 (4)	0.7932 (4)	0.55913 (19)	0.0190 (7)
C8	0.5873 (4)	0.8152 (4)	0.48644 (19)	0.0215 (8)
H8A	0.4981	0.8692	0.4700	0.026*
C9	0.7147 (4)	0.7586 (4)	0.43830 (19)	0.0231 (8)
H9A	0.7116	0.7731	0.3890	0.028*
C10	0.8465 (5)	0.6809 (4)	0.4610 (2)	0.0255 (8)
H10A	0.9336	0.6423	0.4278	0.031*
C11	0.8496 (5)	0.6601 (4)	0.5336 (2)	0.0254 (8)
H11A	0.9394	0.6078	0.5499	0.031*
C12	0.7216 (4)	0.7159 (4)	0.5819 (2)	0.0226 (8)
H12A	0.7244	0.7008	0.6312	0.027*
C13	0.2704 (4)	0.8224 (5)	0.5492 (2)	0.0262 (9)
C14	0.3174 (5)	0.6853 (5)	0.5469 (2)	0.0334 (10)
H14A	0.3712	0.6270	0.5813	0.040*
C15	0.2849 (6)	0.6346 (6)	0.4937 (3)	0.0486 (15)
H15A	0.3158	0.5415	0.4920	0.058*
C16	0.2072 (6)	0.7209 (8)	0.4434 (3)	0.0594 (19)
H16A	0.1849	0.6867	0.4072	0.071*
C17	0.1623 (6)	0.8561 (7)	0.4457 (3)	0.0579 (18)
H17A	0.1109	0.9144	0.4106	0.070*
C18	0.1920 (5)	0.9077 (6)	0.4993 (2)	0.0417 (13)
H18A	0.1585	1.0008	0.5016	0.050*
C19	0.3189 (4)	0.8034 (4)	0.98079 (19)	0.0225 (8)
C20	0.3495 (5)	0.8863 (4)	1.0178 (2)	0.0285 (9)
H20A	0.3391	0.9750	0.9987	0.034*
C21	0.3953 (6)	0.8389 (5)	1.0828 (2)	0.0359 (10)
H21A	0.4132	0.8960	1.1090	0.043*
C22	0.4149 (5)	0.7080 (5)	1.1094 (2)	0.0348 (10)
H22A	0.4469	0.6754	1.1536	0.042*
C23	0.3881 (5)	0.6248 (5)	1.0718 (2)	0.0315 (10)
H23A	0.4022	0.5352	1.0901	0.038*
C24	0.3402 (5)	0.6723 (4)	1.0071 (2)	0.0261 (8)
H24A	0.3222	0.6150	0.9811	0.031*
C25	0.0179 (4)	0.8110 (4)	0.95188 (19)	0.0201 (7)
C26	−0.0146 (4)	0.8250 (4)	1.02446 (19)	0.0226 (8)
H26A	0.0322	0.8715	1.0430	0.027*
C27	−0.1149 (5)	0.7713 (4)	1.0697 (2)	0.0270 (9)
H27A	−0.1355	0.7805	1.1190	0.032*
C28	−0.1853 (5)	0.7045 (5)	1.0433 (2)	0.0346 (10)
H28A	−0.2546	0.6688	1.0745	0.042*
C29	−0.1546 (6)	0.6897 (5)	0.9716 (2)	0.0390 (12)
H29A	−0.2015	0.6426	0.9535	0.047*
C30	−0.0546 (5)	0.7440 (5)	0.9260 (2)	0.0291 (9)
H30A	−0.0355	0.7355	0.8766	0.035*
C31	0.3431 (4)	1.4198 (4)	0.74443 (18)	0.0185 (7)
C32	0.2824 (4)	1.5175 (4)	0.7913 (2)	0.0225 (8)
H32A	0.1887	1.5262	0.8213	0.027*
C33	0.3570 (5)	1.6021 (4)	0.7945 (2)	0.0254 (8)
H33A	0.3146	1.6684	0.8266	0.031*
C34	0.4944 (5)	1.5900 (4)	0.7506 (2)	0.0280 (9)
H34A	0.5464	1.6475	0.7529	0.034*
C35	0.5545 (5)	1.4940 (4)	0.7037 (2)	0.0282 (9)
H35A	0.6476	1.4864	0.6733	0.034*
C36	0.4809 (4)	1.4087 (4)	0.7003 (2)	0.0233 (8)
H36A	0.5239	1.3425	0.6681	0.028*
C37	0.0138 (4)	1.4863 (4)	0.73998 (19)	0.0201 (7)
C38	0.0438 (5)	1.5856 (4)	0.6902 (2)	0.0285 (9)
H38A	0.1277	1.5637	0.6529	0.034*
C39	−0.0481 (6)	1.7168 (5)	0.6947 (3)	0.0371 (11)
H39A	−0.0261	1.7842	0.6609	0.045*
C40	−0.1715 (5)	1.7496 (5)	0.7484 (3)	0.0392 (12)
H40A	−0.2331	1.8395	0.7521	0.047*
C41	−0.2047 (5)	1.6504 (5)	0.7966 (3)	0.0352 (10)
H41A	−0.2905	1.6725	0.8328	0.042*
C42	−0.1141 (5)	1.5195 (4)	0.7924 (2)	0.0262 (8)
H42A	−0.1389	1.4521	0.8252	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.02085 (8)	0.02021 (8)	0.00777 (7)	−0.00861 (5)	0.00061 (5)	−0.00232 (5)
S1	0.0210 (4)	0.0238 (5)	0.0109 (4)	−0.0075 (4)	−0.0004 (3)	−0.0046 (3)
S2	0.0212 (4)	0.0270 (5)	0.0114 (4)	−0.0089 (4)	−0.0002 (3)	−0.0053 (3)
S3	0.0232 (4)	0.0242 (5)	0.0112 (4)	−0.0103 (4)	−0.0018 (3)	−0.0005 (3)
S4	0.0231 (5)	0.0265 (5)	0.0106 (4)	−0.0120 (4)	−0.0009 (3)	−0.0001 (3)
S5	0.0209 (4)	0.0205 (4)	0.0161 (4)	−0.0083 (3)	−0.0015 (3)	−0.0026 (3)
S6	0.0221 (4)	0.0222 (4)	0.0143 (4)	−0.0091 (4)	−0.0006 (3)	−0.0024 (3)
C1	0.0228 (18)	0.0224 (18)	0.0097 (15)	−0.0061 (14)	0.0003 (13)	−0.0018 (13)
C2	0.0273 (19)	0.0221 (18)	0.0097 (15)	−0.0103 (15)	−0.0003 (13)	−0.0035 (13)
C3	0.0279 (19)	0.0205 (18)	0.0083 (15)	−0.0081 (15)	0.0024 (13)	−0.0027 (13)
C4	0.030 (2)	0.0194 (18)	0.0102 (15)	−0.0111 (15)	0.0014 (14)	−0.0033 (13)
C5	0.0235 (18)	0.0204 (18)	0.0076 (14)	−0.0065 (14)	−0.0003 (13)	−0.0019 (12)
C6	0.0269 (19)	0.0213 (18)	0.0084 (15)	−0.0104 (15)	0.0015 (13)	−0.0017 (13)
C7	0.0236 (18)	0.0211 (18)	0.0131 (16)	−0.0101 (15)	0.0001 (13)	−0.0030 (13)
C8	0.0243 (19)	0.0256 (19)	0.0121 (16)	−0.0073 (15)	−0.0007 (14)	−0.0014 (14)
C9	0.030 (2)	0.032 (2)	0.0071 (15)	−0.0141 (17)	0.0034 (14)	−0.0028 (14)
C10	0.027 (2)	0.032 (2)	0.0140 (17)	−0.0090 (17)	0.0075 (14)	−0.0079 (15)
C11	0.026 (2)	0.033 (2)	0.0146 (17)	−0.0073 (17)	−0.0016 (15)	−0.0033 (15)
C12	0.0258 (19)	0.029 (2)	0.0136 (16)	−0.0101 (16)	−0.0014 (14)	−0.0034 (14)
C13	0.0223 (19)	0.043 (2)	0.0152 (17)	−0.0139 (18)	0.0028 (14)	−0.0105 (16)
C14	0.040 (3)	0.043 (3)	0.024 (2)	−0.026 (2)	0.0075 (18)	−0.0140 (19)
C15	0.048 (3)	0.075 (4)	0.037 (3)	−0.042 (3)	0.021 (2)	−0.038 (3)
C16	0.030 (3)	0.118 (6)	0.044 (3)	−0.029 (3)	0.009 (2)	−0.056 (4)
C17	0.029 (3)	0.111 (5)	0.030 (3)	−0.006 (3)	−0.007 (2)	−0.033 (3)
C18	0.025 (2)	0.068 (3)	0.025 (2)	0.002 (2)	−0.0054 (17)	−0.023 (2)
C19	0.0233 (19)	0.028 (2)	0.0130 (16)	−0.0074 (16)	−0.0011 (14)	−0.0005 (14)
C20	0.035 (2)	0.033 (2)	0.0170 (18)	−0.0109 (18)	−0.0065 (16)	−0.0011 (16)
C21	0.046 (3)	0.047 (3)	0.021 (2)	−0.018 (2)	−0.0117 (19)	−0.0039 (19)
C22	0.032 (2)	0.048 (3)	0.0190 (19)	−0.010 (2)	−0.0069 (17)	0.0047 (18)
C23	0.029 (2)	0.037 (2)	0.0199 (19)	−0.0076 (18)	0.0000 (16)	0.0072 (17)
C24	0.030 (2)	0.028 (2)	0.0167 (18)	−0.0087 (17)	−0.0003 (15)	0.0000 (15)
C25	0.0242 (19)	0.0218 (18)	0.0138 (16)	−0.0097 (15)	0.0001 (14)	−0.0010 (13)
C26	0.027 (2)	0.026 (2)	0.0126 (16)	−0.0086 (16)	0.0004 (14)	−0.0017 (14)
C27	0.030 (2)	0.033 (2)	0.0121 (16)	−0.0072 (17)	0.0022 (15)	−0.0007 (15)
C28	0.034 (2)	0.046 (3)	0.023 (2)	−0.020 (2)	0.0004 (18)	0.0059 (19)
C29	0.052 (3)	0.060 (3)	0.018 (2)	−0.041 (3)	−0.0016 (19)	0.002 (2)
C30	0.036 (2)	0.042 (2)	0.0154 (18)	−0.022 (2)	−0.0004 (16)	−0.0034 (16)
C31	0.0248 (19)	0.0203 (18)	0.0117 (15)	−0.0091 (15)	−0.0039 (13)	−0.0004 (13)
C32	0.0215 (19)	0.0243 (19)	0.0195 (18)	−0.0048 (15)	−0.0030 (14)	−0.0038 (15)
C33	0.033 (2)	0.0220 (19)	0.0206 (18)	−0.0063 (16)	−0.0071 (16)	−0.0053 (15)
C34	0.033 (2)	0.025 (2)	0.031 (2)	−0.0148 (18)	−0.0103 (18)	0.0008 (17)
C35	0.030 (2)	0.031 (2)	0.025 (2)	−0.0166 (18)	0.0000 (17)	−0.0004 (17)
C36	0.029 (2)	0.025 (2)	0.0156 (17)	−0.0123 (16)	0.0017 (15)	−0.0032 (14)
C37	0.0224 (18)	0.0227 (19)	0.0158 (16)	−0.0069 (15)	−0.0045 (14)	−0.0038 (14)
C38	0.034 (2)	0.030 (2)	0.026 (2)	−0.0147 (18)	−0.0116 (17)	0.0034 (17)
C39	0.043 (3)	0.029 (2)	0.047 (3)	−0.016 (2)	−0.024 (2)	0.007 (2)
C40	0.039 (3)	0.026 (2)	0.058 (3)	0.0012 (19)	−0.030 (2)	−0.016 (2)
C41	0.029 (2)	0.040 (3)	0.035 (2)	−0.0010 (19)	−0.0093 (19)	−0.019 (2)
C42	0.025 (2)	0.031 (2)	0.0237 (19)	−0.0082 (17)	−0.0045 (16)	−0.0074 (16)

Geometric parameters (Å, º)

Re1—S1	2.3274 (9)	C19—C20	1.392 (6)
Re1—S5	2.3310 (9)	C20—C21	1.392 (6)
Re1—S3	2.3317 (9)	C20—H20A	0.9500
Re1—S4	2.3333 (9)	C21—C22	1.389 (7)
Re1—S6	2.3348 (10)	C21—H21A	0.9500
Re1—S2	2.3348 (9)	C22—C23	1.381 (7)
S1—C1	1.727 (4)	C22—H22A	0.9500
S2—C2	1.723 (4)	C23—C24	1.395 (6)
S3—C3	1.726 (4)	C23—H23A	0.9500
S4—C4	1.728 (4)	C24—H24A	0.9500
S5—C5	1.715 (4)	C25—C26	1.396 (5)
S6—C6	1.730 (4)	C25—C30	1.397 (6)
C1—C2	1.361 (5)	C26—C27	1.387 (5)
C1—C7	1.488 (5)	C26—H26A	0.9500
C2—C13	1.490 (5)	C27—C28	1.384 (7)
C3—C4	1.365 (5)	C27—H27A	0.9500
C3—C19	1.492 (5)	C28—C29	1.383 (6)
C4—C25	1.480 (5)	C28—H28A	0.9500
C5—C6	1.364 (5)	C29—C30	1.392 (6)
C5—C31	1.482 (5)	C29—H29A	0.9500
C6—C37	1.486 (5)	C30—H30A	0.9500
C7—C12	1.386 (5)	C31—C32	1.392 (5)
C7—C8	1.397 (5)	C31—C36	1.400 (5)
C8—C9	1.385 (5)	C32—C33	1.383 (6)
C8—H8A	0.9500	C32—H32A	0.9500
C9—C10	1.386 (6)	C33—C34	1.394 (6)
C9—H9A	0.9500	C33—H33A	0.9500
C10—C11	1.395 (5)	C34—C35	1.379 (6)
C10—H10A	0.9500	C34—H34A	0.9500
C11—C12	1.389 (5)	C35—C36	1.382 (6)
C11—H11A	0.9500	C35—H35A	0.9500
C12—H12A	0.9500	C36—H36A	0.9500
C13—C18	1.382 (6)	C37—C38	1.391 (6)
C13—C14	1.398 (7)	C37—C42	1.397 (5)
C14—C15	1.395 (6)	C38—C39	1.389 (6)
C14—H14A	0.9500	C38—H38A	0.9500
C15—C16	1.389 (9)	C39—C40	1.383 (7)
C15—H15A	0.9500	C39—H39A	0.9500
C16—C17	1.379 (10)	C40—C41	1.385 (7)
C16—H16A	0.9500	C40—H40A	0.9500
C17—C18	1.394 (7)	C41—C42	1.382 (6)
C17—H17A	0.9500	C41—H41A	0.9500
C18—H18A	0.9500	C42—H42A	0.9500
C19—C24	1.386 (6)
S1—Re1—S5	78.53 (3)	C17—C18—H18A	120.2
S1—Re1—S3	85.02 (3)	C24—C19—C20	120.1 (4)
S5—Re1—S3	79.61 (3)	C24—C19—C3	121.0 (4)
S1—Re1—S4	134.55 (4)	C20—C19—C3	118.8 (4)
S5—Re1—S4	139.85 (3)	C19—C20—C21	119.8 (4)
S3—Re1—S4	81.63 (3)	C19—C20—H20A	120.1
S1—Re1—S6	136.08 (3)	C21—C20—H20A	120.1
S5—Re1—S6	82.15 (3)	C22—C21—C20	119.8 (4)
S3—Re1—S6	129.49 (3)	C22—C21—H21A	120.1
S4—Re1—S6	82.99 (3)	C20—C21—H21A	120.1
S1—Re1—S2	81.75 (3)	C23—C22—C21	120.4 (4)
S5—Re1—S2	134.59 (3)	C23—C22—H22A	119.8
S3—Re1—S2	138.67 (3)	C21—C22—H22A	119.8
S4—Re1—S2	80.36 (3)	C22—C23—C24	120.0 (4)
S6—Re1—S2	84.53 (3)	C22—C23—H23A	120.0
C1—S1—Re1	110.02 (13)	C24—C23—H23A	120.0
C2—S2—Re1	109.51 (13)	C19—C24—C23	119.8 (4)
C3—S3—Re1	109.99 (14)	C19—C24—H24A	120.1
C4—S4—Re1	109.92 (14)	C23—C24—H24A	120.1
C5—S5—Re1	109.53 (13)	C26—C25—C30	118.5 (3)
C6—S6—Re1	109.09 (14)	C26—C25—C4	121.7 (3)
C2—C1—C7	125.5 (3)	C30—C25—C4	119.8 (3)
C2—C1—S1	118.8 (3)	C27—C26—C25	120.4 (4)
C7—C1—S1	115.6 (3)	C27—C26—H26A	119.8
C1—C2—C13	124.6 (3)	C25—C26—H26A	119.8
C1—C2—S2	119.8 (3)	C28—C27—C26	120.5 (4)
C13—C2—S2	115.6 (3)	C28—C27—H27A	119.8
C4—C3—C19	125.6 (3)	C26—C27—H27A	119.8
C4—C3—S3	119.1 (3)	C29—C28—C27	120.0 (4)
C19—C3—S3	115.3 (3)	C29—C28—H28A	120.0
C3—C4—C25	125.5 (3)	C27—C28—H28A	120.0
C3—C4—S4	119.1 (3)	C28—C29—C30	119.7 (4)
C25—C4—S4	115.4 (3)	C28—C29—H29A	120.1
C6—C5—C31	126.7 (3)	C30—C29—H29A	120.1
C6—C5—S5	119.8 (3)	C29—C30—C25	120.9 (4)
C31—C5—S5	113.4 (3)	C29—C30—H30A	119.5
C5—C6—C37	122.9 (3)	C25—C30—H30A	119.5
C5—C6—S6	119.4 (3)	C32—C31—C36	118.9 (4)
C37—C6—S6	117.7 (3)	C32—C31—C5	121.5 (3)
C12—C7—C8	118.9 (3)	C36—C31—C5	119.5 (3)
C12—C7—C1	120.9 (3)	C33—C32—C31	120.6 (4)
C8—C7—C1	120.1 (3)	C33—C32—H32A	119.7
C9—C8—C7	120.2 (4)	C31—C32—H32A	119.7
C9—C8—H8A	119.9	C32—C33—C34	120.0 (4)
C7—C8—H8A	119.9	C32—C33—H33A	120.0
C8—C9—C10	120.9 (3)	C34—C33—H33A	120.0
C8—C9—H9A	119.6	C35—C34—C33	119.5 (4)
C10—C9—H9A	119.6	C35—C34—H34A	120.2
C9—C10—C11	119.0 (4)	C33—C34—H34A	120.2
C9—C10—H10A	120.5	C34—C35—C36	120.8 (4)
C11—C10—H10A	120.5	C34—C35—H35A	119.6
C12—C11—C10	120.1 (4)	C36—C35—H35A	119.6
C12—C11—H11A	119.9	C35—C36—C31	120.1 (4)
C10—C11—H11A	119.9	C35—C36—H36A	120.0
C7—C12—C11	120.8 (3)	C31—C36—H36A	120.0
C7—C12—H12A	119.6	C38—C37—C42	119.0 (4)
C11—C12—H12A	119.6	C38—C37—C6	120.2 (4)
C18—C13—C14	120.4 (4)	C42—C37—C6	120.5 (3)
C18—C13—C2	120.9 (4)	C39—C38—C37	120.4 (4)
C14—C13—C2	118.7 (4)	C39—C38—H38A	119.8
C15—C14—C13	119.7 (5)	C37—C38—H38A	119.8
C15—C14—H14A	120.2	C40—C39—C38	120.2 (4)
C13—C14—H14A	120.2	C40—C39—H39A	119.9
C16—C15—C14	119.6 (6)	C38—C39—H39A	119.9
C16—C15—H15A	120.2	C39—C40—C41	119.5 (4)
C14—C15—H15A	120.2	C39—C40—H40A	120.2
C17—C16—C15	120.4 (5)	C41—C40—H40A	120.2
C17—C16—H16A	119.8	C42—C41—C40	120.7 (4)
C15—C16—H16A	119.8	C42—C41—H41A	119.7
C16—C17—C18	120.4 (6)	C40—C41—H41A	119.7
C16—C17—H17A	119.8	C41—C42—C37	120.1 (4)
C18—C17—H17A	119.8	C41—C42—H42A	120.0
C13—C18—C17	119.5 (5)	C37—C42—H42A	120.0
C13—C18—H18A	120.2
S5—Re1—S1—C1	−139.88 (14)	C8—C7—C12—C11	−0.4 (6)
S3—Re1—S1—C1	139.74 (14)	C1—C7—C12—C11	−178.4 (4)
S4—Re1—S1—C1	66.65 (14)	C10—C11—C12—C7	−0.4 (6)
S6—Re1—S1—C1	−74.18 (14)	C1—C2—C13—C18	−115.5 (5)
S2—Re1—S1—C1	−1.00 (14)	S2—C2—C13—C18	65.3 (5)
S1—Re1—S2—C2	2.06 (14)	C1—C2—C13—C14	62.4 (5)
S5—Re1—S2—C2	66.90 (14)	S2—C2—C13—C14	−116.9 (4)
S3—Re1—S2—C2	−70.63 (14)	C18—C13—C14—C15	0.1 (6)
S4—Re1—S2—C2	−135.99 (14)	C2—C13—C14—C15	−177.8 (4)
S6—Re1—S2—C2	140.22 (14)	C13—C14—C15—C16	0.5 (7)
S1—Re1—S3—C3	−139.23 (14)	C14—C15—C16—C17	0.0 (8)
S5—Re1—S3—C3	141.56 (14)	C15—C16—C17—C18	−1.2 (8)
S4—Re1—S3—C3	−2.79 (14)	C14—C13—C18—C17	−1.2 (7)
S6—Re1—S3—C3	70.88 (14)	C2—C13—C18—C17	176.6 (4)
S2—Re1—S3—C3	−67.71 (14)	C16—C17—C18—C13	1.8 (8)
S1—Re1—S4—C4	74.92 (14)	C4—C3—C19—C24	61.1 (6)
S5—Re1—S4—C4	−62.33 (15)	S3—C3—C19—C24	−119.4 (4)
S3—Re1—S4—C4	0.46 (14)	C4—C3—C19—C20	−117.5 (5)
S6—Re1—S4—C4	−131.28 (14)	S3—C3—C19—C20	62.0 (4)
S2—Re1—S4—C4	143.11 (14)	C24—C19—C20—C21	−2.8 (6)
S1—Re1—S5—C5	139.82 (13)	C3—C19—C20—C21	175.8 (4)
S3—Re1—S5—C5	−133.21 (13)	C19—C20—C21—C22	2.1 (7)
S4—Re1—S5—C5	−69.76 (13)	C20—C21—C22—C23	−0.5 (7)
S6—Re1—S5—C5	−0.53 (12)	C21—C22—C23—C24	−0.4 (7)
S2—Re1—S5—C5	73.75 (13)	C20—C19—C24—C23	1.9 (6)
S1—Re1—S6—C6	−65.00 (13)	C3—C19—C24—C23	−176.7 (4)
S5—Re1—S6—C6	−0.63 (12)	C22—C23—C24—C19	−0.3 (6)
S3—Re1—S6—C6	68.92 (13)	C3—C4—C25—C26	44.7 (6)
S4—Re1—S6—C6	141.97 (13)	S4—C4—C25—C26	−135.4 (3)
S2—Re1—S6—C6	−137.11 (13)	C3—C4—C25—C30	−136.5 (4)
Re1—S1—C1—C2	−0.6 (3)	S4—C4—C25—C30	43.4 (5)
Re1—S1—C1—C7	176.7 (2)	C30—C25—C26—C27	1.1 (6)
C7—C1—C2—C13	6.3 (6)	C4—C25—C26—C27	180.0 (4)
S1—C1—C2—C13	−176.6 (3)	C25—C26—C27—C28	−0.7 (6)
C7—C1—C2—S2	−174.5 (3)	C26—C27—C28—C29	0.7 (7)
S1—C1—C2—S2	2.6 (4)	C27—C28—C29—C30	−1.0 (8)
Re1—S2—C2—C1	−3.3 (3)	C28—C29—C30—C25	1.5 (8)
Re1—S2—C2—C13	176.0 (3)	C26—C25—C30—C29	−1.5 (7)
Re1—S3—C3—C4	5.6 (3)	C4—C25—C30—C29	179.6 (4)
Re1—S3—C3—C19	−174.0 (2)	C6—C5—C31—C32	49.1 (5)
C19—C3—C4—C25	−6.1 (6)	S5—C5—C31—C32	−127.3 (3)
S3—C3—C4—C25	174.3 (3)	C6—C5—C31—C36	−134.9 (4)
C19—C3—C4—S4	174.0 (3)	S5—C5—C31—C36	48.8 (4)
S3—C3—C4—S4	−5.6 (4)	C36—C31—C32—C33	−0.2 (6)
Re1—S4—C4—C3	2.8 (3)	C5—C31—C32—C33	175.8 (3)
Re1—S4—C4—C25	−177.2 (2)	C31—C32—C33—C34	0.0 (6)
Re1—S5—C5—C6	2.0 (3)	C32—C33—C34—C35	0.5 (6)
Re1—S5—C5—C31	178.7 (2)	C33—C34—C35—C36	−0.8 (6)
C31—C5—C6—C37	−0.3 (6)	C34—C35—C36—C31	0.5 (6)
S5—C5—C6—C37	175.8 (3)	C32—C31—C36—C35	0.0 (6)
C31—C5—C6—S6	−179.0 (3)	C5—C31—C36—C35	−176.2 (4)
S5—C5—C6—S6	−2.8 (4)	C5—C6—C37—C38	51.7 (5)
Re1—S6—C6—C5	2.1 (3)	S6—C6—C37—C38	−129.6 (3)
Re1—S6—C6—C37	−176.6 (2)	C5—C6—C37—C42	−122.4 (4)
C2—C1—C7—C12	−145.0 (4)	S6—C6—C37—C42	56.3 (4)
S1—C1—C7—C12	37.9 (5)	C42—C37—C38—C39	3.1 (6)
C2—C1—C7—C8	37.0 (6)	C6—C37—C38—C39	−171.0 (4)
S1—C1—C7—C8	−140.1 (3)	C37—C38—C39—C40	−0.8 (7)
C12—C7—C8—C9	1.0 (6)	C38—C39—C40—C41	−1.5 (7)
C1—C7—C8—C9	179.0 (4)	C39—C40—C41—C42	1.3 (7)
C7—C8—C9—C10	−0.8 (6)	C40—C41—C42—C37	1.1 (6)
C8—C9—C10—C11	0.0 (6)	C38—C37—C42—C41	−3.3 (6)
C9—C10—C11—C12	0.6 (6)	C6—C37—C42—C41	170.9 (4)