A pseudosymmetric triclinic modification of tri­phenyl­tin iso­propyl­xanthate

All three independent mol­ecules in the triclinic modification of (O-iso­propyl di­thio­carbonato-S)­tri­phenyl­tin, [Sn(C₆H₅)₃(C₄H₇OS₂)], show tetrahedral coordination at their Sn atoms. Bond dimensions involving the Sn atoms are similar to those found in the monoclinic modification of the same compound. Two of the independent mol­ecules are related by a pseudo-translation allowing a stacking fault that reduces the intensities of h + k odd reflections.

S1. Comment

The structure of the title compound, (I), has a 0.8395:0.1605 (3) stacking fault over alternative origins (a + b)/2 apart that causes the h + k = 2n + 1 reflections to be scaled down by a factor of 0.6791 (5). The structure consists of three different layers perpendicular to c*, each containing two molecles per unit cell. The first two layers are related by a crystallographic inversion whereas the third contains inversion-related molecules. The asymmetric unit is one layer at approximately z = 1/3 that contains molecule a and molecule b [related by a pseudo-translation of (a + b)/2] and a third molecule (molecule c) of a different orientation at approximately z = 0. A pseudo-inversion at (1/4,1/4,1/2) relates the layers at z = ±1/3, and if it acts on the total substructure on one side of an interface at z = 1/2, the net result is a translation of the structure by (a + b)/2. The structure factors are changed to [(1 − a) + a(−1)^h+k]F(hkl)_o, where F(hkl)_o is the structure for the idealized non-stacking-faulted structure and a the average fraction of structure that has been stacking faulted. This effect can be modeled by simply using two scale constants.

Bond dimensions involving the Sn atom are not statistically different among the three molecules, and they are similar to those found in the monoclinic modification (Tiekink & Winter, 1986). For both modifications, the tetrahedral geometry at Sn is distorted owing to an intramolecular Sn···O interaction. The interaction is somewhat shorter than those found in the two independent molecules of triclinic (P1) triphenyltin methoxyethylxanthate (Edwards et al., 1988). This structure is ordered with the two molecules related by a pseudo-inversion at (0.127, 0.215, 0.253).

S2. Experimental

Triphenyltin xanthate, (I), synthesized from reaction between triphenyltin chloride and potassium isopropylxanthate in ethanol, was treated with an equimolar quantity of 2,2'-bipyridine N,N'-dioxide in an attempt to synthesize triphenyltin isopropylxanthate^.2,2'-bipyridine N,N'-dioxide in a sequel to the study on the quinoline N-oxide complex (Ng et al., 1995). The reagents were dissolved in a small volume of hot ethanol; slow cooling of the solution returned the xanthate. Elemental analysis: found: C 54.50, H 4.55%; calculated for C₂₂H₂₂OS₂Sn: C 54.46, H 4.57%. The starting triphenyltin isopropylxanthate reactant exists as the monoclinic modification when recrystallized from ethanol.

S3. Refinement

Two scale constants were used in the refinement to allow for a stacking fault over origins (a+b)/2 apart. Difference maps were calculated with the effects of a stacking fault removed by setting F_o = [Y_o/Y_c]^1/2 × F_c, where F_c is the calculated structure factor for the prototype, and Y_o and Y_c are the observed and calculated values of the intensity. Because reflections are weak for h + k odd, constraints and restraints were used in a refinement that only behaved when two scale constants were used. The modeling for the least-squares refinement used refineable local orthonormal coordinates available in RAELS96 (Rae, 1975, 1996) to describe the atoms in the unit cell. All phenyl groups were restrained to have a common set of local coordinates and to maintain local mm2 symmetry. Restraints were used to minimize differences in bond lengths involving molecule a and molecule b. Twelve different 15-parameter TLX parameterizations (Rae, 1984) were used for the ligand thermal motions, one set per ligand, and librations were initially centered on the relevant Sn atoms. Because of the pseudo translation relationship between molecule a and molecule b, the TLX thermal parameterizations were constrained to retain this relationship (Rae, 1984). These constraints were later removed but reimposed when it was found that variations in TLX parameters were relatively large, had little effect on the statistics and were of no apparent physical meaning. Individual anisotropic displacement parameters were used for the Sn atoms. The stacking fault creates a Sn1c atom at (1/2 − x, 1/2 − y, −z) which lies near atoms C20c and C22c, distorting the apparent geometry in an unconstrained ligand. The distances and angles involving C20c were therefore restrained to minimize their differences from the corresponding features of molecules a and b with little apparent consequence for refinement statistics. In the final cycle, 271 independent variables were used, and the shift/error ratio was less than 0.1 for all but the libration parameters of one ligand. The refinement was stable, the shift/error ratio being an artifact of considering variables one at a time. There is a well recognized singularity in the equations for TLS motion for atoms on a conic section, which is retained should a TLX model of 6 phenyl C atoms have its center of action at the center of the ring. Hydrogen atoms were included in geometrically sensible positions which were updated each refinement cycle. The thermal parameters of H atoms were evaluated using the TLX parameters associated with the atoms to which they are attached. Quoted errors are conditional on the appropriateness of the various constraints and restraints. Refinement statistics are presented in Table 2.

Computing details

Data collection: CAD-4-PC (Kretschmar, 1994); cell refinement: CAD-4-PC (Enraf-Nonius, 1988); data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: RAELS96 (Rae, 1996); software used to prepare material for publication: RAELS96 (Rae, 1996).

iso-Propylxanthatotriphenyltin

Crystal data

[Sn(C6H5)3(C4H7OS2)]	Z = 6
Mr = 485.21	F(000) = 1464
Triclinic, P1	Dx = 1.466 Mg m^−3
a = 10.3136 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.124 (1) Å	Cell parameters from 25 reflections
c = 27.139 (3) Å	θ = 14.5–15.0°
α = 100.346 (9)°	µ = 1.36 mm^−1
β = 93.422 (7)°	T = 298 K
γ = 97.605 (7)°	Cube, light yellow
V = 3297.0 (6) Å^3	0.43 × 0.43 × 0.43 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	8184 reflections with I > 3σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ω scans	h = 0→12
Absorption correction: ψ scan [North et al. (1968) in WinGX (Farrugia, 1997)]	k = −14→14
Tmin = 0.515, Tmax = 0.557	l = −32→32
12299 measured reflections	3 standard reflections every 60 min
11586 independent reflections	intensity decay: 2%

Refinement

Refinement on F	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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	Part of TLX rigid body motions
S = 1.45	w = 1/[σ(F)^2 + (0.04F)^2]
11586 reflections	(Δ/σ)max = 0.3
271 parameters	Δρmax = 1.31 e Å^−3
33 restraints	Δρmin = −0.83 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1a	−0.05401 (5)	−0.04852 (4)	0.32132 (2)	0.0508 (2)
S1a	−0.2730 (2)	−0.0788 (2)	0.3507 (1)	0.063 (1)
S2a	−0.3982 (2)	0.0743 (2)	0.4241 (1)	0.072 (1)
O1a	−0.1910 (4)	0.1328 (3)	0.3766 (2)	0.058 (1)
C1a	−0.0483 (5)	−0.2180 (3)	0.2821 (2)	0.050 (2)
C2a	−0.0331 (6)	−0.3039 (4)	0.3080 (2)	0.060 (3)
C3a	−0.0338 (6)	−0.4142 (3)	0.2822 (2)	0.073 (3)
C4a	−0.0497 (7)	−0.4371 (4)	0.2310 (2)	0.082 (3)
C5a	−0.0649 (7)	−0.3532 (5)	0.2047 (2)	0.086 (2)
C6a	−0.0642 (6)	−0.2428 (4)	0.2304 (2)	0.068 (1)
C7a	0.0791 (5)	0.0049 (4)	0.3870 (2)	0.054 (3)
C8a	0.1748 (6)	0.0973 (5)	0.3908 (2)	0.073 (2)
C9a	0.2605 (5)	0.1331 (5)	0.4340 (2)	0.089 (3)
C10a	0.2494 (6)	0.0760 (6)	0.4729 (2)	0.090 (4)
C11a	0.1553 (7)	−0.0157 (6)	0.4699 (2)	0.097 (4)
C12a	0.0695 (6)	−0.0516 (4)	0.4266 (2)	0.076 (4)
C13a	−0.0365 (5)	0.0674 (4)	0.2707 (2)	0.055 (3)
C14a	0.0842 (5)	0.1022 (5)	0.2551 (2)	0.069 (2)
C15a	0.0976 (6)	0.1821 (5)	0.2241 (2)	0.083 (2)
C16a	−0.0098 (7)	0.2260 (5)	0.2090 (2)	0.090 (3)
C17a	−0.1303 (6)	0.1925 (5)	0.2240 (2)	0.098 (4)
C18a	−0.1437 (5)	0.1127 (5)	0.2551 (2)	0.076 (3)
C19a	−0.2847 (5)	0.0554 (4)	0.3861 (2)	0.057 (1)
C20a	−0.1823 (8)	0.2532 (5)	0.4015 (3)	0.072 (1)
C21a	−0.0796 (10)	0.2759 (7)	0.4441 (3)	0.090 (1)
C22a	−0.1551 (9)	0.3209 (6)	0.3603 (3)	0.079 (1)
Sn1b	0.45148 (5)	0.44430 (4)	0.32264 (2)	0.0483 (2)
S1b	0.2352 (2)	0.4106 (2)	0.3539 (1)	0.063 (1)
S2b	0.1034 (2)	0.5718 (2)	0.4211 (1)	0.070 (1)
O1b	0.3103 (4)	0.6236 (3)	0.3722 (2)	0.058 (1)
C1b	0.4689 (5)	0.2732 (3)	0.2888 (2)	0.050 (2)
C2b	0.4556 (6)	0.1868 (4)	0.3157 (2)	0.062 (3)
C3b	0.4609 (6)	0.0757 (3)	0.2922 (2)	0.075 (3)
C4b	0.4793 (7)	0.0525 (3)	0.2423 (2)	0.079 (3)
C5b	0.4926 (7)	0.1368 (5)	0.2151 (2)	0.082 (2)
C6b	0.4874 (6)	0.2480 (4)	0.2385 (2)	0.066 (2)
C7b	0.5851 (5)	0.5101 (4)	0.3874 (2)	0.054 (3)
C8b	0.6803 (6)	0.6023 (5)	0.3898 (2)	0.076 (2)
C9b	0.7656 (5)	0.6419 (5)	0.4330 (3)	0.093 (3)
C10b	0.7544 (6)	0.5889 (6)	0.4731 (2)	0.089 (3)
C11b	0.6607 (7)	0.4974 (6)	0.4714 (2)	0.092 (4)
C12b	0.5754 (6)	0.4577 (4)	0.4283 (2)	0.073 (4)
C13b	0.4463 (5)	0.5457 (4)	0.2661 (2)	0.057 (3)
C14b	0.5548 (5)	0.6150 (5)	0.2564 (2)	0.065 (2)
C15b	0.5457 (6)	0.6798 (5)	0.2192 (2)	0.079 (2)
C16b	0.4284 (7)	0.6745 (6)	0.1923 (2)	0.094 (4)
C17b	0.3198 (6)	0.6064 (6)	0.2014 (2)	0.107 (5)
C18b	0.3287 (5)	0.5415 (5)	0.2386 (2)	0.083 (4)
C19b	0.2183 (5)	0.5481 (4)	0.3843 (2)	0.056 (1)
C20b	0.3153 (8)	0.7452 (5)	0.3943 (3)	0.070 (1)
C21b	0.4131 (9)	0.7734 (7)	0.4385 (3)	0.087 (1)
C22b	0.3480 (9)	0.8076 (6)	0.3517 (3)	0.079 (1)
Sn1c	0.27912 (5)	0.12792 (4)	0.04668 (2)	0.0486 (2)
S1c	0.0956 (2)	0.2174 (2)	0.0800 (1)	0.060 (1)
S2c	0.0248 (2)	0.4436 (2)	0.0801 (1)	0.075 (1)
O1c	0.2013 (5)	0.3498 (4)	0.0256 (2)	0.056 (1)
C1c	0.2293 (5)	−0.0301 (4)	0.0702 (2)	0.053 (3)
C2c	0.2281 (6)	−0.0334 (4)	0.1206 (2)	0.071 (4)
C3c	0.1892 (7)	−0.1350 (6)	0.1363 (2)	0.091 (6)
C4c	0.1521 (6)	−0.2319 (4)	0.1015 (3)	0.087 (5)
C5c	0.1527 (6)	−0.2304 (4)	0.0514 (2)	0.083 (4)
C6c	0.1916 (6)	−0.1288 (4)	0.0356 (2)	0.069 (3)
C7c	0.4572 (4)	0.2256 (4)	0.0836 (2)	0.050 (2)
C8c	0.4591 (5)	0.3324 (4)	0.1117 (2)	0.060 (2)
C9c	0.5771 (6)	0.3959 (4)	0.1342 (2)	0.072 (2)
C10c	0.6913 (5)	0.3518 (5)	0.1283 (2)	0.079 (3)
C11c	0.6914 (4)	0.2462 (6)	0.1006 (2)	0.079 (4)
C12c	0.5735 (5)	0.1826 (4)	0.0781 (2)	0.063 (3)
C13c	0.2829 (5)	0.1067 (4)	−0.0330 (2)	0.053 (3)
C14c	0.1716 (5)	0.0674 (5)	−0.0652 (2)	0.066 (4)
C15c	0.1779 (6)	0.0534 (5)	−0.1170 (2)	0.085 (5)
C16c	0.2954 (7)	0.0790 (6)	−0.1359 (2)	0.088 (5)
C17c	0.4068 (6)	0.1180 (5)	−0.1046 (2)	0.081 (4)
C18c	0.4006 (5)	0.1320 (5)	−0.0528 (2)	0.065 (3)
C19c	0.1150 (7)	0.3474 (6)	0.0599 (3)	0.054 (1)
C20c	0.2287 (8)	0.4487 (6)	0.0007 (3)	0.080 (1)
C21c	0.3368 (9)	0.5290 (7)	0.0322 (4)	0.104 (2)
C22c	0.2552 (13)	0.3978 (9)	−0.0526 (3)	0.111 (1)
H1C2a	−0.0215	−0.2869	0.3455	0.072
H1C3a	−0.0227	−0.4763	0.3011	0.091
H1C4a	−0.0501	−0.5163	0.2125	0.100
H1C5a	−0.0764	−0.3708	0.1671	0.117
H1C6a	−0.0754	−0.1812	0.2112	0.082
H1C8a	0.1828	0.1391	0.3622	0.097
H1C9a	0.3298	0.2004	0.4366	0.123
H1C10a	0.3109	0.1018	0.5039	0.111
H1C11a	0.1479	−0.0571	0.4985	0.138
H1C12a	0.0004	−0.1189	0.4243	0.100
H1C14a	0.1629	0.0699	0.2662	0.089
H1C15a	0.1855	0.2071	0.2129	0.107
H1C16a	−0.0002	0.2833	0.1867	0.113
H1C17a	−0.2085	0.2252	0.2127	0.139
H1C18a	−0.2320	0.0881	0.2661	0.096
H1C20a	−0.2686	0.2668	0.4146	0.077
H1C21a	−0.1059	0.2278	0.4692	0.096
H2C21a	0.0055	0.2575	0.4313	0.090
H3C21a	−0.0691	0.3577	0.4604	0.110
H1C22a	−0.2292	0.3000	0.3333	0.076
H2C22a	−0.1463	0.4037	0.3747	0.096
H3C22a	−0.0717	0.3034	0.3457	0.082
H1C2b	0.4421	0.2040	0.3523	0.075
H1C3b	0.4512	0.0132	0.3119	0.097
H1C4b	0.4831	−0.0274	0.2255	0.096
H1C5b	0.5061	0.1190	0.1785	0.109
H1C6b	0.4972	0.3100	0.2186	0.081
H1C8b	0.6884	0.6411	0.3603	0.102
H1C9b	0.8346	0.7090	0.4345	0.129
H1C10b	0.8157	0.6174	0.5041	0.110
H1C11b	0.6533	0.4591	0.5010	0.129
H1C12b	0.5067	0.3906	0.4270	0.095
H1C14b	0.6408	0.6187	0.2762	0.081
H1C15b	0.6248	0.7300	0.2123	0.098
H1C16b	0.4219	0.7211	0.1656	0.118
H1C17b	0.2341	0.6031	0.1815	0.154
H1C18b	0.2492	0.4915	0.2453	0.106
H1C20b	0.2271	0.7594	0.4051	0.075
H1C21b	0.3837	0.7287	0.4644	0.092
H2C21b	0.5000	0.7543	0.4279	0.087
H3C21b	0.4217	0.8562	0.4529	0.106
H1C22b	0.2770	0.7834	0.3236	0.077
H2C22b	0.3551	0.8911	0.3643	0.096
H3C22b	0.4335	0.7891	0.3393	0.082
H1C2c	0.2553	0.0377	0.1461	0.095
H1C3c	0.1884	−0.1370	0.1730	0.132
H1C4c	0.1242	−0.3048	0.1128	0.114
H1C5c	0.1253	−0.3018	0.0261	0.116
H1C6c	0.1921	−0.1275	−0.0011	0.094
H1C8c	0.3752	0.3646	0.1160	0.078
H1C9c	0.5780	0.4734	0.1546	0.097
H1C10c	0.7760	0.3974	0.1444	0.104
H1C11c	0.7757	0.2145	0.0965	0.112
H1C12c	0.5734	0.1051	0.0578	0.081
H1C14c	0.0855	0.0487	−0.0512	0.077
H1C15c	0.0968	0.0248	−0.1402	0.111
H1C16c	0.2999	0.0690	−0.1731	0.113
H1C17c	0.4925	0.1365	−0.1189	0.103
H1C18c	0.4822	0.1606	−0.0298	0.076
H1C20c	0.1484	0.4866	−0.0006	0.084
H1C21c	0.3070	0.5561	0.0660	0.101
H2C21c	0.4151	0.4896	0.0360	0.113
H3C21c	0.3609	0.5952	0.0155	0.134
H1C22c	0.1754	0.3458	−0.0696	0.111
H2C22c	0.2767	0.4599	−0.0718	0.147
H3C22c	0.3308	0.3543	−0.0514	0.115

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1a	0.0499 (3)	0.0448 (3)	0.0560 (3)	0.0070 (2)	0.0018 (3)	0.0059 (2)
S1a	0.055 (1)	0.044 (1)	0.088 (1)	0.000 (1)	0.014 (1)	0.009 (1)
S2a	0.068 (1)	0.075 (1)	0.071 (1)	0.002 (1)	0.026 (1)	0.010 (1)
O1a	0.053 (1)	0.046 (1)	0.073 (1)	−0.003 (1)	0.013 (1)	0.006 (1)
C1a	0.045 (3)	0.052 (2)	0.051 (3)	0.004 (2)	−0.002 (2)	0.009 (1)
C2a	0.063 (4)	0.054 (2)	0.063 (4)	0.010 (2)	−0.002 (3)	0.014 (2)
C3a	0.079 (5)	0.054 (2)	0.085 (4)	0.013 (2)	−0.001 (4)	0.010 (2)
C4a	0.089 (4)	0.062 (2)	0.086 (3)	0.018 (2)	−0.010 (3)	−0.006 (2)
C5a	0.113 (5)	0.076 (2)	0.064 (2)	0.032 (3)	−0.009 (2)	−0.007 (2)
C6a	0.085 (3)	0.067 (2)	0.051 (2)	0.020 (2)	−0.001 (2)	0.005 (1)
C7a	0.052 (3)	0.050 (4)	0.059 (3)	0.012 (3)	0.005 (2)	0.008 (2)
C8a	0.063 (3)	0.071 (4)	0.077 (2)	−0.007 (3)	−0.002 (2)	0.008 (3)
C9a	0.071 (3)	0.094 (5)	0.089 (3)	−0.004 (3)	−0.012 (2)	−0.003 (3)
C10a	0.082 (4)	0.102 (5)	0.078 (3)	0.020 (4)	−0.019 (3)	−0.004 (3)
C11a	0.110 (6)	0.104 (6)	0.073 (3)	0.012 (5)	−0.023 (3)	0.020 (4)
C12a	0.088 (4)	0.075 (5)	0.065 (2)	0.006 (3)	−0.009 (2)	0.022 (3)
C13a	0.055 (5)	0.054 (4)	0.059 (3)	0.012 (2)	0.005 (2)	0.011 (3)
C14a	0.063 (4)	0.077 (3)	0.072 (2)	0.009 (2)	0.013 (2)	0.022 (2)
C15a	0.092 (4)	0.081 (3)	0.077 (3)	0.000 (3)	0.017 (3)	0.026 (2)
C16a	0.123 (5)	0.078 (6)	0.081 (4)	0.022 (3)	0.021 (3)	0.034 (4)
C17a	0.109 (4)	0.112 (9)	0.097 (5)	0.048 (4)	0.020 (3)	0.056 (6)
C18a	0.069 (5)	0.092 (7)	0.079 (4)	0.029 (2)	0.008 (2)	0.037 (4)
C19a	0.054 (1)	0.049 (1)	0.067 (1)	−0.002 (1)	0.016 (1)	0.008 (1)
C20a	0.066 (1)	0.048 (1)	0.091 (1)	−0.004 (1)	0.006 (1)	−0.002 (1)
C21a	0.086 (2)	0.066 (2)	0.102 (2)	−0.010 (2)	−0.010 (1)	−0.007 (2)
C22a	0.063 (1)	0.048 (1)	0.122 (2)	−0.008 (1)	0.005 (1)	0.018 (1)
Sn1b	0.0470 (3)	0.0443 (3)	0.0544 (3)	0.0058 (2)	0.0040 (2)	0.0115 (2)
S1b	0.055 (1)	0.044 (1)	0.088 (1)	0.000 (1)	0.014 (1)	0.009 (1)
S2b	0.066 (1)	0.071 (1)	0.072 (1)	0.003 (1)	0.026 (1)	0.008 (1)
O1b	0.052 (1)	0.045 (1)	0.073 (1)	−0.003 (1)	0.014 (1)	0.007 (1)
C1b	0.045 (3)	0.052 (2)	0.052 (3)	0.004 (2)	−0.002 (2)	0.010 (1)
C2b	0.068 (4)	0.054 (2)	0.065 (4)	0.010 (2)	0.001 (4)	0.016 (2)
C3b	0.084 (6)	0.054 (2)	0.088 (5)	0.013 (2)	0.002 (5)	0.014 (2)
C4b	0.085 (4)	0.060 (2)	0.086 (4)	0.018 (2)	−0.006 (3)	−0.002 (2)
C5b	0.103 (4)	0.074 (2)	0.067 (2)	0.029 (2)	0.003 (2)	−0.001 (2)
C6b	0.078 (3)	0.066 (2)	0.056 (2)	0.018 (2)	0.008 (2)	0.008 (1)
C7b	0.051 (3)	0.050 (4)	0.060 (3)	0.011 (3)	0.005 (2)	0.007 (2)
C8b	0.068 (3)	0.071 (3)	0.080 (2)	−0.011 (3)	−0.004 (2)	0.010 (3)
C9b	0.077 (3)	0.093 (5)	0.092 (3)	−0.010 (3)	−0.014 (2)	−0.001 (3)
C10b	0.079 (3)	0.100 (5)	0.079 (3)	0.017 (3)	−0.017 (2)	−0.006 (3)
C11b	0.100 (5)	0.103 (5)	0.069 (3)	0.013 (4)	−0.017 (3)	0.015 (3)
C12b	0.080 (4)	0.074 (5)	0.062 (2)	0.007 (3)	−0.005 (2)	0.018 (3)
C13b	0.056 (5)	0.056 (4)	0.059 (3)	0.011 (2)	0.004 (2)	0.011 (3)
C14b	0.066 (4)	0.065 (3)	0.066 (2)	0.007 (2)	0.010 (2)	0.016 (2)
C15b	0.098 (4)	0.071 (4)	0.072 (3)	0.008 (2)	0.016 (2)	0.023 (2)
C16b	0.111 (6)	0.103 (8)	0.083 (4)	0.027 (4)	0.011 (3)	0.045 (5)
C17b	0.090 (7)	0.153 (12)	0.094 (5)	0.021 (4)	−0.006 (3)	0.065 (7)
C18b	0.066 (7)	0.112 (8)	0.076 (4)	0.006 (3)	−0.008 (3)	0.038 (4)
C19b	0.053 (1)	0.047 (1)	0.067 (1)	−0.002 (1)	0.016 (1)	0.007 (1)
C20b	0.064 (1)	0.046 (1)	0.093 (1)	−0.004 (1)	0.007 (1)	0.001 (1)
C21b	0.082 (2)	0.061 (1)	0.103 (2)	−0.009 (1)	−0.007 (1)	−0.006 (1)
C22b	0.061 (1)	0.050 (1)	0.123 (2)	−0.008 (1)	0.006 (1)	0.023 (1)
Sn1c	0.0511 (3)	0.0454 (3)	0.0499 (3)	0.0052 (2)	0.0090 (2)	0.0106 (2)
S1c	0.061 (2)	0.062 (1)	0.065 (2)	0.015 (1)	0.025 (1)	0.023 (1)
S2c	0.071 (2)	0.064 (1)	0.095 (2)	0.025 (1)	0.026 (1)	0.013 (1)
O1c	0.051 (2)	0.054 (1)	0.069 (2)	0.010 (1)	0.017 (1)	0.021 (1)
C1c	0.046 (5)	0.044 (3)	0.070 (5)	0.008 (2)	−0.001 (4)	0.010 (3)
C2c	0.085 (6)	0.057 (3)	0.071 (7)	0.010 (3)	0.000 (4)	0.015 (3)
C3c	0.112 (11)	0.075 (4)	0.093 (8)	0.011 (5)	0.009 (6)	0.037 (4)
C4c	0.080 (8)	0.060 (2)	0.126 (8)	0.002 (3)	−0.002 (5)	0.040 (4)
C5c	0.085 (6)	0.044 (2)	0.115 (6)	0.002 (2)	−0.017 (5)	0.014 (3)
C6c	0.077 (5)	0.046 (2)	0.079 (4)	0.009 (2)	−0.006 (4)	0.005 (3)
C7c	0.056 (4)	0.051 (3)	0.046 (3)	0.004 (2)	0.004 (2)	0.016 (2)
C8c	0.074 (3)	0.057 (3)	0.050 (3)	0.011 (2)	0.001 (2)	0.011 (2)
C9c	0.097 (4)	0.058 (3)	0.057 (3)	−0.006 (3)	−0.013 (3)	0.015 (2)
C10c	0.072 (3)	0.093 (6)	0.065 (4)	−0.018 (3)	−0.012 (3)	0.029 (3)
C11c	0.058 (3)	0.112 (7)	0.070 (5)	0.013 (4)	−0.002 (2)	0.022 (4)
C12c	0.065 (3)	0.070 (4)	0.057 (3)	0.018 (4)	0.000 (2)	0.014 (2)
C13c	0.059 (5)	0.047 (4)	0.057 (3)	0.011 (3)	0.012 (2)	0.013 (2)
C14c	0.068 (5)	0.065 (6)	0.062 (3)	0.009 (3)	0.005 (2)	0.007 (3)
C15c	0.099 (6)	0.092 (9)	0.060 (3)	0.019 (4)	0.000 (3)	0.004 (3)
C16c	0.120 (7)	0.091 (7)	0.058 (3)	0.027 (5)	0.021 (3)	0.013 (2)
C17c	0.097 (6)	0.081 (5)	0.071 (3)	0.019 (4)	0.035 (3)	0.017 (3)
C18c	0.066 (5)	0.063 (4)	0.068 (3)	0.013 (2)	0.021 (2)	0.014 (2)
C19c	0.050 (2)	0.053 (1)	0.063 (2)	0.012 (1)	0.014 (1)	0.014 (1)
C20c	0.081 (2)	0.067 (1)	0.109 (3)	0.016 (1)	0.035 (2)	0.044 (2)
C21c	0.075 (3)	0.062 (1)	0.183 (6)	0.002 (1)	0.033 (3)	0.044 (2)
C22c	0.145 (5)	0.108 (3)	0.110 (3)	0.043 (3)	0.067 (3)	0.068 (3)
H1C2a	0.096	0.063	0.063	0.024	−0.001	0.020
H1C3a	0.115	0.058	0.106	0.024	0.006	0.020
H1C4a	0.115	0.067	0.107	0.026	−0.015	−0.015
H1C5a	0.182	0.102	0.065	0.062	−0.014	−0.016
H1C6a	0.125	0.081	0.047	0.036	0.007	0.011
H1C8a	0.093	0.091	0.093	−0.039	−0.011	0.025
H1C9a	0.097	0.127	0.116	−0.037	−0.025	0.002
H1C10a	0.099	0.131	0.089	0.025	−0.032	−0.011
H1C11a	0.174	0.148	0.086	−0.007	−0.045	0.046
H1C12a	0.126	0.094	0.077	−0.020	−0.020	0.044
H1C14a	0.059	0.126	0.097	0.021	0.023	0.049
H1C15a	0.102	0.124	0.098	−0.013	0.023	0.046
H1C16a	0.168	0.091	0.096	0.030	0.031	0.048
H1C17a	0.138	0.187	0.141	0.089	0.036	0.107
H1C18a	0.063	0.144	0.103	0.038	0.009	0.065
H1C20a	0.075	0.053	0.092	0.002	0.012	−0.011
H1C21a	0.098	0.085	0.086	−0.009	−0.009	−0.007
H2C21a	0.075	0.065	0.117	−0.014	−0.014	0.008
H3C21a	0.107	0.071	0.126	−0.011	−0.018	−0.020
H1C22a	0.060	0.051	0.116	−0.006	0.009	0.025
H2C22a	0.076	0.046	0.159	−0.010	−0.004	0.015
H3C22a	0.059	0.058	0.128	−0.011	0.008	0.031
H1C2b	0.104	0.063	0.067	0.023	0.010	0.026
H1C3b	0.126	0.057	0.114	0.023	0.016	0.026
H1C4b	0.109	0.065	0.107	0.025	−0.010	−0.009
H1C5b	0.164	0.097	0.069	0.055	0.014	−0.004
H1C6b	0.115	0.078	0.058	0.031	0.027	0.017
H1C8b	0.101	0.094	0.097	−0.045	−0.014	0.029
H1C9b	0.108	0.128	0.123	−0.046	−0.030	0.006
H1C10b	0.095	0.128	0.089	0.021	−0.029	−0.014
H1C11b	0.156	0.148	0.078	−0.004	−0.036	0.038
H1C12b	0.115	0.095	0.071	−0.017	−0.014	0.039
H1C14b	0.061	0.101	0.082	−0.003	0.008	0.033
H1C15b	0.121	0.089	0.085	−0.009	0.021	0.032
H1C16b	0.146	0.131	0.098	0.038	0.017	0.066
H1C17b	0.102	0.254	0.130	0.021	−0.020	0.117
H1C18b	0.066	0.161	0.092	−0.012	−0.020	0.058
H1C20b	0.071	0.049	0.095	0.002	0.013	−0.007
H1C21b	0.094	0.078	0.087	−0.007	−0.006	−0.009
H2C21b	0.072	0.061	0.116	−0.014	−0.011	0.008
H3C21b	0.102	0.064	0.130	−0.010	−0.015	−0.019
H1C22b	0.061	0.056	0.116	−0.006	0.010	0.030
H2C22b	0.073	0.048	0.161	−0.010	−0.002	0.024
H3C22b	0.059	0.062	0.128	−0.011	0.011	0.035
H1C2c	0.144	0.068	0.070	0.013	−0.007	0.008
H1C3c	0.200	0.110	0.099	0.018	0.021	0.054
H1C4c	0.107	0.073	0.171	−0.003	−0.003	0.063
H1C5c	0.143	0.046	0.145	−0.001	−0.037	0.005
H1C6c	0.140	0.059	0.076	0.015	−0.006	−0.001
H1C8c	0.092	0.083	0.061	0.034	0.001	0.002
H1C9c	0.150	0.059	0.071	−0.002	−0.029	0.008
H1C10c	0.087	0.131	0.083	−0.039	−0.025	0.041
H1C11c	0.065	0.178	0.096	0.037	−0.003	0.022
H1C12c	0.096	0.080	0.070	0.040	−0.006	0.006
H1C14c	0.064	0.082	0.077	0.001	0.003	0.002
H1C15c	0.116	0.134	0.070	0.020	−0.015	−0.006
H1C16c	0.163	0.122	0.059	0.038	0.027	0.015
H1C17c	0.114	0.110	0.092	0.017	0.057	0.021
H1C18c	0.060	0.086	0.084	0.010	0.021	0.012
H1C20c	0.089	0.068	0.109	0.022	0.025	0.045
H1C21c	0.075	0.053	0.171	0.000	0.006	0.018
H2C21c	0.065	0.068	0.211	−0.002	0.034	0.044
H3C21c	0.101	0.073	0.246	0.004	0.057	0.071
H1C22c	0.166	0.117	0.076	0.052	0.041	0.053
H2C22c	0.199	0.137	0.152	0.059	0.098	0.102
H3C22c	0.138	0.112	0.128	0.042	0.087	0.069

Geometric parameters (Å, º)

Sn1a—S1a	2.443 (1)	C8b—C9b	1.393 (3)
Sn1a—C1a	2.148 (3)	C9b—C10b	1.363 (3)
Sn1a—C7a	2.131 (3)	C10b—C11b	1.363 (3)
Sn1a—C13a	2.134 (3)	C11b—C12b	1.393 (3)
S1a—C19a	1.758 (5)	C13b—C14b	1.376 (2)
S2a—C19a	1.617 (5)	C13b—C18b	1.376 (2)
O1a—C19a	1.326 (6)	C14b—C15b	1.393 (3)
O1a—C20a	1.484 (6)	C15b—C16b	1.363 (3)
C1a—C2a	1.376 (2)	C16b—C17b	1.363 (3)
C1a—C6a	1.376 (2)	C17b—C18b	1.393 (3)
C2a—C3a	1.393 (3)	C20b—C21b	1.480 (9)
C3a—C4a	1.363 (3)	C20b—C22b	1.520 (9)
C4a—C5a	1.363 (3)	Sn1c—S1c	2.444 (2)
C5a—C6a	1.393 (3)	Sn1c—C1c	2.136 (4)
C7a—C8a	1.376 (2)	Sn1c—C7c	2.135 (4)
C7a—C12a	1.376 (2)	Sn1c—C13c	2.135 (4)
C8a—C9a	1.393 (3)	S1c—C19c	1.750 (7)
C9a—C10a	1.363 (3)	S2c—C19c	1.626 (7)
C10a—C11a	1.363 (3)	O1c—C19c	1.326 (7)
C11a—C12a	1.393 (3)	O1c—C20c	1.483 (6)
C13a—C14a	1.376 (2)	C1c—C2c	1.376 (2)
C13a—C18a	1.376 (2)	C1c—C6c	1.376 (2)
C14a—C15a	1.393 (3)	C2c—C3c	1.393 (3)
C15a—C16a	1.363 (3)	C3c—C4c	1.363 (3)
C16a—C17a	1.363 (3)	C4c—C5c	1.363 (3)
C17a—C18a	1.393 (3)	C5c—C6c	1.393 (3)
C20a—C21a	1.481 (9)	C7c—C8c	1.376 (2)
C20a—C22a	1.520 (9)	C7c—C12c	1.376 (2)
Sn1b—S1b	2.444 (1)	C8c—C9c	1.393 (3)
Sn1b—C1b	2.148 (3)	C9c—C10c	1.363 (3)
Sn1b—C7b	2.131 (3)	C10c—C11c	1.363 (3)
Sn1b—C13b	2.133 (3)	C11c—C12c	1.393 (3)
S1b—C19b	1.757 (5)	C13c—C14c	1.376 (2)
S2b—C19b	1.616 (5)	C13c—C18c	1.376 (2)
O1b—C19b	1.328 (6)	C14c—C15c	1.393 (3)
O1b—C20b	1.482 (6)	C15c—C16c	1.363 (3)
C1b—C2b	1.376 (2)	C16c—C17c	1.363 (3)
C1b—C6b	1.376 (2)	C17c—C18c	1.393 (3)
C2b—C3b	1.393 (3)	C20c—C21c	1.490 (9)
C3b—C4b	1.363 (3)	C20c—C22c	1.523 (9)
C4b—C5b	1.363 (3)	Sn1a—O1a	2.995 (4)
C5b—C6b	1.393 (3)	Sn1b—O1b	2.945 (4)
C7b—C8b	1.376 (2)	Sn1c—O1c	3.045 (4)
C7b—C12b	1.376 (2)
S1a—Sn1a—C1a	98.3 (2)	C7b—C8b—C9b	120.5 (2)
S1a—Sn1a—C7a	106.3 (2)	C8b—C9b—C10b	119.6 (2)
S1a—Sn1a—C13a	113.5 (2)	C9b—C10b—C11b	120.8 (3)
C1a—Sn1a—C7a	114.8 (2)	C10b—C11b—C12b	119.6 (2)
C1a—Sn1a—C13a	110.4 (2)	C7b—C12b—C11b	120.5 (2)
C7a—Sn1a—C13a	112.8 (2)	Sn1b—C13b—C14b	122.9 (3)
Sn1a—S1a—C19a	101.9 (2)	Sn1b—C13b—C18b	118.1 (3)
C19a—O1a—C20a	120.5 (5)	C14b—C13b—C18b	119.0 (2)
Sn1a—C1a—C2a	120.9 (3)	C13b—C14b—C15b	120.5 (2)
Sn1a—C1a—C6a	120.0 (3)	C14b—C15b—C16b	119.6 (2)
C2a—C1a—C6a	119.0 (2)	C15b—C16b—C17b	120.8 (3)
C1a—C2a—C3a	120.5 (2)	C16b—C17b—C18b	119.6 (2)
C2a—C3a—C4a	119.6 (2)	C13b—C18b—C17b	120.5 (2)
C3a—C4a—C5a	120.8 (3)	S1b—C19b—S2b	122.0 (3)
C4a—C5a—C6a	119.6 (2)	S1b—C19b—O1b	110.4 (4)
C1a—C6a—C5a	120.5 (2)	S2b—C19b—O1b	127.6 (4)
Sn1a—C7a—C8a	120.5 (3)	O1b—C20b—C21b	108.1 (6)
Sn1a—C7a—C12a	120.5 (3)	O1b—C20b—C22b	105.0 (5)
C8a—C7a—C12a	119.0 (2)	C21b—C20b—C22b	115.0 (6)
C7a—C8a—C9a	120.5 (2)	S1c—Sn1c—C1c	97.2 (2)
C8a—C9a—C10a	119.6 (2)	S1c—Sn1c—C7c	108.1 (1)
C9a—C10a—C11a	120.8 (3)	S1c—Sn1c—C13c	114.5 (1)
C10a—C11a—C12a	119.6 (2)	C1c—Sn1c—C7c	114.0 (2)
C7a—C12a—C11a	120.5 (2)	C1c—Sn1c—C13c	111.9 (2)
Sn1a—C13a—C14a	120.1 (3)	C7c—Sn1c—C13c	110.6 (2)
Sn1a—C13a—C18a	120.8 (3)	Sn1c—S1c—C19c	103.3 (2)
C14a—C13a—C18a	119.0 (2)	C19c—O1c—C20c	121.5 (5)
C13a—C14a—C15a	120.5 (2)	Sn1c—C1c—C2c	120.0 (3)
C14a—C15a—C16a	119.6 (2)	Sn1c—C1c—C6c	121.0 (3)
C15a—C16a—C17a	120.8 (3)	C2c—C1c—C6c	119.0 (2)
C16a—C17a—C18a	119.6 (2)	C1c—C2c—C3c	120.5 (2)
C13a—C18a—C17a	120.5 (2)	C2c—C3c—C4c	119.6 (2)
S1a—C19a—S2a	121.7 (3)	C3c—C4c—C5c	120.8 (3)
S1a—C19a—O1a	110.7 (4)	C4c—C5c—C6c	119.6 (2)
S2a—C19a—O1a	127.6 (4)	C1c—C6c—C5c	120.5 (2)
O1a—C20a—C21a	108.2 (6)	Sn1c—C7c—C8c	121.5 (3)
O1a—C20a—C22a	105.1 (5)	Sn1c—C7c—C12c	119.4 (3)
C21a—C20a—C22a	115.2 (6)	C8c—C7c—C12c	119.0 (2)
S1b—Sn1b—C1b	99.0 (1)	C7c—C8c—C9c	120.5 (2)
S1b—Sn1b—C7b	105.9 (2)	C8c—C9c—C10c	119.6 (2)
S1b—Sn1b—C13b	110.5 (2)	C9c—C10c—C11c	120.8 (3)
C1b—Sn1b—C7b	113.4 (2)	C10c—C11c—C12c	119.6 (2)
C1b—Sn1b—C13b	109.8 (2)	C7c—C12c—C11c	120.5 (2)
C7b—Sn1b—C13b	116.7 (2)	Sn1c—C13c—C14c	122.0 (3)
Sn1b—S1b—C19b	100.9 (2)	Sn1c—C13c—C18c	119.0 (3)
C19b—O1b—C20b	119.4 (5)	C14c—C13c—C18c	119.0 (2)
Sn1b—C1b—C2b	121.6 (3)	C13c—C14c—C15c	120.5 (2)
Sn1b—C1b—C6b	119.3 (3)	C14c—C15c—C16c	119.6 (2)
C2b—C1b—C6b	119.0 (2)	C15c—C16c—C17c	120.8 (3)
C1b—C2b—C3b	120.5 (2)	C16c—C17c—C18c	119.6 (2)
C2b—C3b—C4b	119.6 (2)	C13c—C18c—C17c	120.5 (2)
C3b—C4b—C5b	120.8 (3)	S1c—C19c—S2c	120.3 (4)
C4b—C5b—C6b	119.6 (2)	S1c—C19c—O1c	111.5 (5)
C1b—C6b—C5b	120.5 (2)	S2c—C19c—O1c	128.1 (5)
Sn1b—C7b—C8b	122.6 (3)	O1c—C20c—C21c	107.3 (6)
Sn1b—C7b—C12b	118.4 (3)	O1c—C20c—C22c	104.5 (5)
C8b—C7b—C12b	119.0 (2)	C21c—C20c—C22c	117.4 (7)
C19a—S1a—Sn1a—C1a	177.5 (2)	C8b—C7b—Sn1b—C13b	−11.3 (4)
C19a—S1a—Sn1a—C7a	58.6 (2)	C12b—C7b—Sn1b—C13b	168.8 (3)
C19a—S1a—Sn1a—C13a	−65.9 (2)	C14b—C13b—Sn1b—S1b	152.9 (3)
C2a—C1a—Sn1a—S1a	−73.4 (3)	C18b—C13b—Sn1b—S1b	−26.8 (3)
C2a—C1a—Sn1a—C7a	38.9 (4)	C14b—C13b—Sn1b—C1b	−99.0 (4)
C2a—C1a—Sn1a—C13a	167.7 (3)	C18b—C13b—Sn1b—C1b	81.3 (3)
C6a—C1a—Sn1a—S1a	104.5 (3)	C14b—C13b—Sn1b—C7b	31.9 (4)
C6a—C1a—Sn1a—C7a	−143.2 (3)	C18b—C13b—Sn1b—C7b	−147.8 (3)
C6a—C1a—Sn1a—C13a	−14.4 (4)	S2b—C19b—S1b—Sn1b	−168.2 (2)
C8a—C7a—Sn1a—S1a	−132.6 (3)	S1b—C19b—O1b—C20b	180.8 (5)
C12a—C7a—Sn1a—S1a	46.4 (3)	S2b—C19b—O1b—C20b	1.2 (6)
C8a—C7a—Sn1a—C1a	119.9 (3)	C21b—C20b—O1b—C19b	96.5 (7)
C12a—C7a—Sn1a—C1a	−61.1 (4)	C22b—C20b—O1b—C19b	−140.3 (5)
C8a—C7a—Sn1a—C13a	−7.7 (4)	C19c—S1c—Sn1c—C1c	−176.1 (3)
C12a—C7a—Sn1a—C13a	171.3 (3)	C19c—S1c—Sn1c—C7c	65.7 (3)
C14a—C13a—Sn1a—S1a	173.1 (3)	C19c—S1c—Sn1c—C13c	−58.1 (3)
C18a—C13a—Sn1a—S1a	−3.7 (4)	C2c—C1c—Sn1c—S1c	−63.0 (3)
C14a—C13a—Sn1a—C1a	−77.7 (4)	C6c—C1c—Sn1c—S1c	113.6 (3)
C18a—C13a—Sn1a—C1a	105.6 (3)	C2c—C1c—Sn1c—C7c	50.6 (4)
C14a—C13a—Sn1a—C7a	52.2 (4)	C6c—C1c—Sn1c—C7c	−132.9 (3)
C18a—C13a—Sn1a—C7a	−124.6 (3)	C2c—C1c—Sn1c—C13c	177.0 (3)
S2a—C19a—S1a—Sn1a	−166.1 (2)	C6c—C1c—Sn1c—C13c	−6.4 (4)
S1a—C19a—O1a—C20a	179.0 (5)	C8c—C7c—Sn1c—S1c	−13.3 (3)
S2a—C19a—O1a—C20a	−0.7 (6)	C12c—C7c—Sn1c—S1c	168.7 (2)
C21a—C20a—O1a—C19a	99.8 (7)	C8c—C7c—Sn1c—C1c	−120.1 (3)
C22a—C20a—O1a—C19a	−136.7 (5)	C12c—C7c—Sn1c—C1c	61.8 (3)
C19b—S1b—Sn1b—C1b	177.8 (2)	C8c—C7c—Sn1c—C13c	112.8 (3)
C19b—S1b—Sn1b—C7b	60.2 (2)	C12c—C7c—Sn1c—C13c	−65.2 (3)
C19b—S1b—Sn1b—C13b	−67.0 (2)	C14c—C13c—Sn1c—S1c	−44.2 (3)
C2b—C1b—Sn1b—S1b	−54.9 (3)	C18c—C13c—Sn1c—S1c	136.5 (3)
C6b—C1b—Sn1b—S1b	121.9 (3)	C14c—C13c—Sn1c—C1c	65.1 (4)
C2b—C1b—Sn1b—C7b	56.8 (4)	C18c—C13c—Sn1c—C1c	−114.2 (3)
C6b—C1b—Sn1b—C7b	−126.4 (3)	C14c—C13c—Sn1c—C7c	−166.6 (3)
C2b—C1b—Sn1b—C13b	−170.6 (3)	C18c—C13c—Sn1c—C7c	14.1 (3)
C6b—C1b—Sn1b—C13b	6.2 (4)	S2c—C19c—S1c—Sn1c	−171.6 (4)
C8b—C7b—Sn1b—S1b	−134.8 (3)	S1c—C19c—O1c—C20c	176.4 (5)
C12b—C7b—Sn1b—S1b	45.4 (3)	S2c—C19c—O1c—C20c	1.0 (10)
C8b—C7b—Sn1b—C1b	117.8 (3)	C21c—C20c—O1c—C19c	89.2 (8)
C12b—C7b—Sn1b—C1b	−62.1 (4)	C22c—C20c—O1c—C19c	−145.4 (8)