[μ₂-2,5-Dimercapto-1,3,4-thia­diazole(2–)-κ²N:N]bis­(μ₂-methano­lato)-μ₃-oxido-tris­[bis­(4-fluoro­benz­yl)tin(IV)] benzene hemisolvate

The title complex, [Sn₃(C₇H₇F)₆(CH₃O)₂(C₂N₂S₃)O]·0.5C₆H₆, contains a unique μ₃-OSn₃N₂O₂ central core with three five-coordinated Sn atoms with distorted trigonal–bipyramidal geometries; the benzene mol­ecule resides on a crystallographic inversion center (at the ring centroid). One Sn atom (with a C₂O₃ ligand set) has Sn—O bond lengths in the range 2.044 (4)–2.131 (5) Å; the remaining two Sn atoms (with C₂O₂N ligand sets) have Sn—O distances ranging from 2.038 (5) to 2.188 (5) Å. The two Sn—N bond lengths are 2.217 (5) and 2.225 (6) Å, and the six Sn—C bond lengths range from 2.125 (8) to 2.150 (8) Å. There are no clasical hydrogen bonds in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.055
• wR factor = 0.184
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C38
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C37
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         16

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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S1. Comment

From Fig. 1, like other trinuclear organotin-µ₃oxo clusters (Ma et al., 2007), the complex (I) contains a tricyclic system formed from a N₂Sn₂O ring and two Sn₂O₂ rings: all three Sn atoms exhibit severely distorted trigonal bipyramidal configurations. The atoms Sn2 and Sn3 have similar environments, in which one O atom and two C atoms of the benzyl groups occupy the equatorial positions (C5, C12 and O1 for Sn2; C19, C26 and O1 for Sn3). The axial positions are occupied by one N atom of the HHdmt and one O atom of the methoxy group (N2 and O2 for Sn1; N1 and O3 for Sn3). The geometry of Sn1 is cis-R₂SnO₃, in which the axial positions are defined by O2 and O3 atoms of methoxy group, C33 and C40 atoms of benzyl groups and one O atom occupy the equatorial plane.

With regard to the role of reaction hydrolysis, three [(C₇H₇F)₂Sn] units are bridged by one O atom and two O atoms of methoxy group, forming a trinuclear complex, containing two Sn₂O₂ rings. Three Sn atoms and three O atoms (Sn1, Sn2, Sn3, O1, O2, O3) comprise a fused ring system, which is similar to traditional hydrolytic products of ladder-type arrangement (Puff et al., 1983), but different from the staircase structure of C₈₄H₁₄₈N₈O₁₀Sn₄ (Yin et al., 2006). The Sn—O distances lies in the range 2.038 (5) to 2.188 (5) Å (Table 1), which are consistent with those Sn—O bonds in the ladder structure reported (Harrison et al., 1980). All of above indicates that strong bridge-oxo coordination with Sn atoms exist in the complex. Moreover, the aromatic rings effectively surround the –O—CH₃ group.

The HHdmt ligand forms a five-membered ring, where two N atoms bond to the two Sn atoms to form another five-membered N₂Sn₂O₁ ring. The Sn—N bond lengths [Sn2—N2 2.225 (6) Å and Sn3—N1 2.217 (7) Å] approach the covalent radii of Sn and N (2.15 Å) and are much shorter than the van der Waal's radii of Sn and N atoms (3.74 Å) (Hubeey et al., 1993), proving that N is coordinated to Sn by strong chemical bonds.

Related literature

For related literature please review the following: ladder-type Sn₃O₃ arrangements (Puff et al., 1983), trinuclear RSnO clusters (Ma et al., 2007), a staircase Sn₄O₁₀ structure (Yin et al., 2006), related Sn ladder systems (Harrison et al., 1980), and van der Waal's radii of Sn and N atoms (Hubeey et al., 1993).

S2. Experimental

The 2,5-dimercapto-1,3,4-thiadiazole (1 mmol) was added to the solution of methanol 20 ml with sodium methoxide (2 mmol), and the mixture was stirred for 30 minutes, then di(4-fluorobenzyl)tin (3 mmol) was added to the mixture, continuing the reaction for 12 h at 318k. After cooling down to room temperature, this was then filtered. The solvent of the filtrate was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from benzene and colorless crystals suitable for X-ray diffraction was obtained (m.p. 356 K). Analysis, calculated for C₄₉H₁₅F₆N₂O₃S₃Sn₃: C 46.11, H 3.55, N 2.20; found: C 46.16, H 3.59, N 2.18%.

S3. Refinement

All H atoms were placed geometrically and treated as riding on their parent atoms, with thiadiazole C—H and methyl C—H distances at 0.96 Å. The U_iso(H) values were set at 1.5U_eq(C) for all H atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of the title complex (I), showing 30% probability displacement ellipsoids.
	Fig. 2. Unit cell of the title complex (I).

[µ₂-2,5-Dimercapto-1,3,4-thiadiazole(2-)-κ²N:N]bis(µ₂– methanolato)-µ₃-oxido-tris[bis(4-fluorobenzyl)tin(IV)] benzene hemisolvate

Crystal data

[Sn3(C7H7F)6(CH3O)2(C2N2S3)O]·0.5C6H6	F(000) = 2516
Mr = 1276.12	Dx = 1.702 Mg m^−3
Monoclinic, P21/c	Melting point: 356 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.3309 (9) Å	Cell parameters from 9782 reflections
b = 45.937 (4) Å	θ = 1.8–26.0°
c = 13.5763 (8) Å	µ = 1.68 mm^−1
β = 129.394 (4)°	T = 293 K
V = 4979.1 (7) Å^3	Block, colorless
Z = 4	0.18 × 0.16 × 0.08 mm

Data collection

Siemens SMART CCD area-detector diffractometer	9782 independent reflections
Radiation source: fine-focus sealed tube	8279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.751, Tmax = 0.877	k = −56→56
51752 measured reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.123P)^2 + 12.502P] where P = (Fo^2 + 2Fc^2)/3
9782 reflections	(Δ/σ)max = 0.003
591 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −1.78 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
Sn1	1.09057 (6)	0.872437 (11)	0.26253 (5)	0.04148 (16)
Sn2	0.99142 (6)	0.942464 (10)	0.27698 (4)	0.03669 (15)
Sn3	0.68330 (6)	0.880017 (10)	0.12982 (5)	0.03655 (15)
S1	0.2941 (3)	0.90904 (5)	0.0062 (3)	0.0677 (6)
S2	0.4469 (3)	0.96904 (4)	0.1112 (2)	0.0548 (5)
S3	0.7698 (3)	1.00416 (5)	0.2581 (2)	0.0594 (5)
F1	0.8398 (10)	0.88068 (14)	0.6454 (7)	0.094 (2)
F2	0.5363 (10)	0.91417 (15)	−0.3438 (5)	0.104 (2)
F3	0.7676 (14)	0.74570 (16)	0.3886 (12)	0.152 (4)
F4	0.2991 (11)	0.76864 (14)	−0.2917 (7)	0.112 (3)
F5	0.9696 (12)	0.77323 (17)	−0.1815 (9)	0.125 (3)
F6	1.5752 (11)	0.75227 (17)	0.4952 (8)	0.120 (3)
O1	0.9093 (5)	0.90072 (10)	0.2213 (4)	0.0384 (10)
O2	1.1931 (6)	0.91524 (11)	0.3167 (5)	0.0492 (13)
O3	0.8669 (6)	0.84801 (11)	0.1676 (5)	0.0456 (12)
N1	0.6135 (7)	0.92511 (12)	0.1374 (6)	0.0386 (13)
N2	0.7269 (7)	0.94780 (12)	0.1975 (5)	0.0380 (12)
C1	0.4561 (10)	0.93234 (17)	0.0851 (8)	0.0454 (17)
C2	0.6593 (9)	0.97345 (16)	0.1925 (7)	0.0440 (16)
C3	1.3556 (10)	0.9245 (2)	0.3585 (10)	0.065 (2)
H3A	1.4285	0.9080	0.3885	0.097*
H3B	1.4033	0.9385	0.4262	0.097*
H3C	1.3423	0.9333	0.2883	0.097*
C4	0.8373 (12)	0.81699 (16)	0.1369 (8)	0.056 (2)
H4A	0.8231	0.8135	0.0608	0.084*
H4B	0.7381	0.8111	0.1236	0.084*
H4C	0.9314	0.8060	0.2061	0.084*
C5	1.1099 (11)	0.95023 (19)	0.4733 (7)	0.054 (2)
H5A	1.2292	0.9467	0.5247	0.065*
H5B	1.0943	0.9705	0.4841	0.065*
C6	1.0403 (9)	0.93103 (17)	0.5198 (6)	0.0423 (16)
C7	0.8973 (11)	0.93993 (18)	0.5021 (8)	0.0502 (18)
H7	0.8468	0.9576	0.4622	0.060*
C8	0.8298 (12)	0.9226 (2)	0.5436 (9)	0.063 (2)
H8	0.7330	0.9284	0.5294	0.076*
C9	0.9057 (13)	0.8974 (2)	0.6044 (8)	0.062 (2)
C10	1.0485 (13)	0.8888 (2)	0.6276 (8)	0.064 (2)
H10	1.1011	0.8716	0.6716	0.077*
C11	1.1143 (10)	0.9055 (2)	0.5860 (7)	0.056 (2)
H11	1.2126	0.8995	0.6029	0.067*
C12	0.9649 (11)	0.96861 (18)	0.1346 (7)	0.0516 (19)
H12A	0.9217	0.9876	0.1320	0.062*
H12B	1.0741	0.9714	0.1574	0.062*
C13	0.8495 (9)	0.95493 (15)	0.0050 (7)	0.0399 (15)
C14	0.9149 (11)	0.9391 (2)	−0.0428 (8)	0.057 (2)
H14	1.0302	0.9375	0.0051	0.068*
C15	0.8075 (14)	0.9260 (2)	−0.1618 (9)	0.068 (3)
H15	0.8498	0.9159	−0.1955	0.082*
C16	0.6388 (13)	0.9280 (2)	−0.2283 (7)	0.061 (2)
C17	0.5720 (11)	0.94291 (17)	−0.1855 (8)	0.053 (2)
H17	0.4564	0.9443	−0.2338	0.064*
C18	0.6791 (10)	0.95621 (16)	−0.0677 (7)	0.0450 (17)
H18	0.6337	0.9664	−0.0368	0.054*
C19	0.6611 (15)	0.8640 (2)	0.2674 (11)	0.070 (3)
H19A	0.7386	0.8749	0.3458	0.084*
H19B	0.5489	0.8684	0.2364	0.084*
C20	0.6921 (10)	0.83251 (17)	0.2988 (7)	0.0452 (17)
C21	0.5731 (12)	0.8119 (2)	0.2202 (9)	0.067 (2)
H21	0.4712	0.8178	0.1447	0.081*
C22	0.5989 (17)	0.7829 (2)	0.2487 (14)	0.086 (3)
H22	0.5172	0.7693	0.1928	0.104*
C23	0.7414 (18)	0.7745 (2)	0.3566 (15)	0.084 (3)
C24	0.8651 (14)	0.7927 (3)	0.4403 (12)	0.082 (3)
H24	0.9641	0.7858	0.5157	0.099*
C25	0.8414 (11)	0.8229 (2)	0.4110 (9)	0.069 (3)
H25	0.9257	0.8361	0.4669	0.082*
C26	0.5420 (11)	0.87894 (17)	−0.0712 (7)	0.0494 (18)
H26A	0.4479	0.8922	−0.1101	0.059*
H26B	0.6118	0.8860	−0.0907	0.059*
C27	0.4760 (9)	0.84916 (16)	−0.1307 (7)	0.0440 (16)
C28	0.5399 (12)	0.8352 (2)	−0.1822 (8)	0.058 (2)
H28	0.6229	0.8440	−0.1798	0.069*
C29	0.4788 (13)	0.8078 (2)	−0.2377 (8)	0.066 (2)
H29	0.5196	0.7984	−0.2737	0.079*
C30	0.3596 (15)	0.7950 (2)	−0.2388 (9)	0.073 (3)
C31	0.2951 (13)	0.8087 (2)	−0.1873 (9)	0.069 (2)
H31	0.2128	0.7997	−0.1891	0.082*
C32	0.3555 (10)	0.83586 (18)	−0.1331 (8)	0.0534 (19)
H32	0.3136	0.8453	−0.0979	0.064*
C33	1.1616 (14)	0.8670 (2)	0.1472 (10)	0.0653 (18)
H33A	1.1257	0.8843	0.0947	0.078*
H33B	1.2830	0.8668	0.2038	0.078*
C34	1.1027 (13)	0.8414 (2)	0.0609 (10)	0.0653 (18)
C35	1.1589 (13)	0.8136 (2)	0.1060 (9)	0.066 (2)
H35	1.2299	0.8102	0.1934	0.079*
C36	1.1128 (14)	0.7909 (2)	0.0253 (11)	0.074 (3)
H36	1.1493	0.7721	0.0569	0.089*
C37	1.0143 (14)	0.7959 (2)	−0.0998 (11)	0.073 (3)
C38	0.9535 (16)	0.8222 (3)	−0.1497 (11)	0.089 (3)
H38	0.8808	0.8249	−0.2375	0.107*
C39	1.0005 (14)	0.8453 (2)	−0.0687 (10)	0.072 (3)
H39	0.9623	0.8639	−0.1024	0.087*
C40	1.2385 (11)	0.8535 (2)	0.4489 (8)	0.060 (2)
H40A	1.3207	0.8676	0.5105	0.072*
H40B	1.1664	0.8490	0.4695	0.072*
C41	1.3267 (10)	0.82649 (17)	0.4604 (7)	0.0479 (17)
C42	1.4822 (11)	0.8276 (2)	0.4905 (9)	0.062 (2)
H42	1.5316	0.8456	0.5031	0.075*
C43	1.5658 (13)	0.8028 (3)	0.5021 (10)	0.077 (3)
H43	1.6709	0.8040	0.5236	0.092*
C44	1.4915 (17)	0.7767 (3)	0.4816 (10)	0.080 (3)
C45	1.3412 (15)	0.7739 (2)	0.4501 (10)	0.079 (3)
H45	1.2937	0.7556	0.4359	0.095*
C46	1.2565 (12)	0.7988 (2)	0.4388 (8)	0.062 (2)
H46	1.1511	0.7971	0.4164	0.074*
C47	0.5586 (14)	1.0005 (2)	0.4335 (10)	0.069 (3)
H47	0.5976	1.0009	0.3878	0.082*
C48	0.6669 (13)	0.99371 (17)	0.5618 (10)	0.060 (2)
H48	0.7787	0.9895	0.6031	0.072*
C49	0.6062 (14)	0.9934 (2)	0.6267 (9)	0.070 (3)
H49	0.6780	0.9889	0.7131	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0409 (3)	0.0400 (3)	0.0480 (3)	0.0006 (2)	0.0303 (2)	−0.0030 (2)
Sn2	0.0393 (3)	0.0357 (3)	0.0343 (3)	−0.00752 (19)	0.0230 (2)	−0.00782 (18)
Sn3	0.0391 (3)	0.0312 (3)	0.0435 (3)	−0.00509 (18)	0.0282 (2)	−0.00437 (18)
S1	0.0481 (11)	0.0596 (13)	0.1021 (19)	−0.0090 (10)	0.0509 (13)	−0.0123 (12)
S2	0.0542 (11)	0.0422 (10)	0.0713 (14)	0.0074 (9)	0.0413 (11)	−0.0030 (9)
S3	0.0691 (14)	0.0409 (10)	0.0666 (13)	−0.0066 (9)	0.0423 (12)	−0.0162 (9)
F1	0.134 (6)	0.089 (4)	0.103 (5)	−0.019 (4)	0.096 (5)	0.004 (4)
F2	0.127 (6)	0.101 (5)	0.041 (3)	−0.002 (4)	0.033 (3)	−0.019 (3)
F3	0.208 (10)	0.067 (5)	0.267 (12)	0.047 (5)	0.190 (10)	0.052 (6)
F4	0.156 (7)	0.060 (4)	0.091 (5)	−0.026 (4)	0.065 (5)	−0.032 (3)
F5	0.171 (8)	0.099 (5)	0.151 (7)	−0.044 (5)	0.123 (7)	−0.065 (5)
F6	0.142 (7)	0.101 (5)	0.115 (6)	0.059 (5)	0.080 (5)	0.009 (4)
O1	0.033 (2)	0.032 (2)	0.045 (3)	−0.0005 (18)	0.022 (2)	−0.0051 (19)
O2	0.037 (3)	0.050 (3)	0.062 (3)	−0.009 (2)	0.032 (3)	−0.015 (3)
O3	0.046 (3)	0.035 (3)	0.062 (3)	−0.003 (2)	0.037 (3)	−0.005 (2)
N1	0.041 (3)	0.034 (3)	0.052 (3)	−0.001 (2)	0.035 (3)	−0.004 (2)
N2	0.037 (3)	0.035 (3)	0.039 (3)	−0.002 (2)	0.023 (3)	−0.007 (2)
C1	0.047 (4)	0.044 (4)	0.059 (5)	0.001 (3)	0.040 (4)	0.003 (3)
C2	0.048 (4)	0.042 (4)	0.045 (4)	0.003 (3)	0.031 (4)	−0.006 (3)
C3	0.044 (4)	0.066 (6)	0.092 (7)	−0.005 (4)	0.047 (5)	−0.005 (5)
C4	0.069 (5)	0.036 (4)	0.062 (5)	0.016 (4)	0.041 (5)	−0.001 (4)
C5	0.057 (5)	0.061 (5)	0.040 (4)	−0.013 (4)	0.028 (4)	−0.017 (4)
C6	0.042 (4)	0.052 (4)	0.028 (3)	−0.002 (3)	0.020 (3)	−0.008 (3)
C7	0.057 (5)	0.052 (5)	0.048 (4)	0.003 (4)	0.037 (4)	0.002 (3)
C8	0.065 (5)	0.081 (6)	0.064 (5)	0.000 (5)	0.050 (5)	−0.002 (5)
C9	0.086 (7)	0.058 (5)	0.053 (5)	−0.013 (5)	0.049 (5)	−0.001 (4)
C10	0.079 (6)	0.054 (5)	0.050 (5)	0.006 (5)	0.037 (5)	0.005 (4)
C11	0.046 (4)	0.072 (6)	0.035 (4)	0.004 (4)	0.019 (4)	0.000 (4)
C12	0.058 (5)	0.050 (4)	0.050 (4)	−0.005 (4)	0.036 (4)	0.003 (4)
C13	0.049 (4)	0.036 (3)	0.040 (4)	0.006 (3)	0.031 (3)	0.005 (3)
C14	0.054 (5)	0.074 (6)	0.044 (4)	0.020 (4)	0.032 (4)	0.008 (4)
C15	0.099 (8)	0.070 (6)	0.052 (5)	0.028 (5)	0.056 (6)	0.007 (4)
C16	0.076 (6)	0.055 (5)	0.032 (4)	0.006 (4)	0.025 (4)	0.003 (3)
C17	0.046 (4)	0.049 (5)	0.045 (4)	0.005 (3)	0.019 (4)	0.014 (3)
C18	0.053 (4)	0.043 (4)	0.050 (4)	0.009 (3)	0.038 (4)	0.007 (3)
C19	0.103 (8)	0.062 (6)	0.088 (7)	0.010 (5)	0.080 (7)	0.012 (5)
C20	0.054 (4)	0.046 (4)	0.053 (4)	−0.007 (3)	0.042 (4)	−0.002 (3)
C21	0.055 (5)	0.073 (6)	0.058 (5)	−0.017 (5)	0.029 (4)	0.002 (5)
C22	0.101 (9)	0.062 (7)	0.124 (10)	−0.026 (6)	0.085 (9)	−0.014 (7)
C23	0.105 (9)	0.051 (6)	0.141 (11)	0.010 (6)	0.099 (9)	0.022 (7)
C24	0.069 (6)	0.092 (8)	0.105 (8)	0.033 (6)	0.064 (7)	0.049 (7)
C25	0.050 (5)	0.085 (7)	0.065 (6)	−0.019 (5)	0.034 (5)	−0.005 (5)
C26	0.057 (5)	0.045 (4)	0.044 (4)	−0.007 (3)	0.032 (4)	−0.001 (3)
C27	0.043 (4)	0.043 (4)	0.038 (4)	−0.003 (3)	0.022 (3)	−0.002 (3)
C28	0.064 (5)	0.066 (5)	0.050 (5)	0.002 (4)	0.039 (4)	−0.005 (4)
C29	0.086 (7)	0.062 (6)	0.047 (5)	0.007 (5)	0.040 (5)	−0.007 (4)
C30	0.099 (8)	0.046 (5)	0.054 (5)	−0.004 (5)	0.039 (6)	−0.013 (4)
C31	0.068 (6)	0.057 (5)	0.065 (6)	−0.016 (5)	0.035 (5)	−0.009 (4)
C32	0.052 (4)	0.050 (4)	0.050 (4)	−0.008 (4)	0.028 (4)	−0.006 (4)
C33	0.087 (5)	0.062 (4)	0.088 (5)	−0.019 (3)	0.075 (4)	−0.016 (3)
C34	0.087 (5)	0.062 (4)	0.088 (5)	−0.019 (3)	0.075 (4)	−0.016 (3)
C35	0.078 (6)	0.073 (6)	0.056 (5)	0.014 (5)	0.047 (5)	0.011 (4)
C36	0.098 (8)	0.050 (5)	0.104 (8)	0.020 (5)	0.078 (7)	0.017 (5)
C37	0.081 (7)	0.071 (6)	0.092 (8)	−0.018 (5)	0.066 (7)	−0.027 (6)
C38	0.094 (8)	0.101 (9)	0.054 (6)	0.001 (7)	0.038 (6)	−0.001 (6)
C39	0.089 (7)	0.061 (6)	0.070 (6)	0.022 (5)	0.052 (6)	0.022 (5)
C40	0.060 (5)	0.071 (6)	0.048 (5)	0.008 (4)	0.034 (4)	−0.002 (4)
C41	0.051 (4)	0.052 (5)	0.038 (4)	0.005 (3)	0.027 (4)	0.006 (3)
C42	0.049 (5)	0.074 (6)	0.059 (5)	−0.007 (4)	0.032 (4)	−0.005 (4)
C43	0.053 (5)	0.101 (9)	0.072 (6)	0.019 (5)	0.038 (5)	−0.004 (6)
C44	0.101 (9)	0.072 (7)	0.056 (6)	0.033 (6)	0.045 (6)	0.003 (5)
C45	0.090 (8)	0.051 (5)	0.067 (6)	−0.003 (5)	0.036 (6)	0.000 (5)
C46	0.063 (5)	0.078 (6)	0.043 (4)	0.006 (5)	0.032 (4)	0.008 (4)
C47	0.090 (7)	0.057 (5)	0.087 (7)	−0.032 (5)	0.069 (6)	−0.022 (5)
C48	0.070 (6)	0.039 (4)	0.083 (7)	−0.005 (4)	0.054 (5)	−0.003 (4)
C49	0.080 (7)	0.061 (6)	0.057 (5)	−0.015 (5)	0.037 (5)	0.000 (4)

Geometric parameters (Å, º)

Sn1—O1	2.044 (4)	C18—H18	0.9300
Sn1—O3	2.116 (5)	C19—C20	1.486 (12)
Sn1—C33	2.125 (8)	C19—H19A	0.9700
Sn1—O2	2.131 (5)	C19—H19B	0.9700
Sn1—C40	2.142 (9)	C20—C21	1.373 (12)
Sn2—O1	2.038 (5)	C20—C25	1.383 (12)
Sn2—C12	2.141 (7)	C21—C22	1.366 (15)
Sn2—C5	2.142 (7)	C21—H21	0.9300
Sn2—O2	2.184 (5)	C22—C23	1.312 (17)
Sn2—N2	2.225 (6)	C22—H22	0.9300
Sn3—O1	2.054 (4)	C23—C24	1.334 (18)
Sn3—C26	2.127 (8)	C24—C25	1.419 (15)
Sn3—C19	2.150 (8)	C24—H24	0.9300
Sn3—O3	2.188 (5)	C25—H25	0.9300
Sn3—N1	2.217 (5)	C26—C27	1.513 (10)
S1—C1	1.679 (8)	C26—H26A	0.9700
S2—C2	1.732 (8)	C26—H26B	0.9700
S2—C1	1.738 (8)	C27—C32	1.369 (11)
S3—C2	1.672 (8)	C27—C28	1.386 (11)
F1—C9	1.358 (10)	C28—C29	1.394 (13)
F2—C16	1.370 (10)	C28—H28	0.9300
F3—C23	1.367 (12)	C29—C30	1.357 (15)
F4—C30	1.342 (11)	C29—H29	0.9300
F5—C37	1.371 (11)	C30—C31	1.386 (15)
F6—C44	1.357 (11)	C31—C32	1.381 (12)
O2—C3	1.454 (9)	C31—H31	0.9300
O3—C4	1.462 (9)	C32—H32	0.9300
N1—C1	1.339 (9)	C33—C34	1.488 (12)
N1—N2	1.382 (8)	C33—H33A	0.9700
N2—C2	1.349 (9)	C33—H33B	0.9700
C3—H3A	0.9600	C34—C39	1.373 (14)
C3—H3B	0.9600	C34—C35	1.377 (13)
C3—H3C	0.9600	C35—C36	1.360 (14)
C4—H4A	0.9600	C35—H35	0.9300
C4—H4B	0.9600	C36—C37	1.334 (15)
C4—H4C	0.9600	C36—H36	0.9300
C5—C6	1.506 (11)	C37—C38	1.331 (16)
C5—H5A	0.9700	C38—C39	1.375 (15)
C5—H5B	0.9700	C38—H38	0.9300
C6—C11	1.376 (12)	C39—H39	0.9300
C6—C7	1.399 (11)	C40—C41	1.487 (12)
C7—C8	1.390 (12)	C40—H40A	0.9700
C7—H7	0.9300	C40—H40B	0.9700
C8—C9	1.348 (13)	C41—C42	1.385 (12)
C8—H8	0.9300	C41—C46	1.399 (12)
C9—C10	1.357 (14)	C42—C43	1.375 (14)
C10—C11	1.363 (13)	C42—H42	0.9300
C10—H10	0.9300	C43—C44	1.353 (17)
C11—H11	0.9300	C43—H43	0.9300
C12—C13	1.500 (11)	C44—C45	1.330 (16)
C12—H12A	0.9700	C45—C46	1.389 (14)
C12—H12B	0.9700	C45—H45	0.9300
C13—C18	1.368 (10)	C46—H46	0.9300
C13—C14	1.400 (10)	C47—C49^i	1.372 (15)
C14—C15	1.391 (13)	C47—C48	1.381 (14)
C14—H14	0.9300	C47—H47	0.9300
C15—C16	1.366 (14)	C48—C49	1.368 (13)
C15—H15	0.9300	C48—H48	0.9300
C16—C17	1.338 (13)	C49—C47^i	1.372 (15)
C17—C18	1.382 (11)	C49—H49	0.9300
C17—H17	0.9300
O1—Sn1—O3	73.36 (18)	C13—C18—C17	122.3 (7)
O1—Sn1—C33	123.9 (3)	C13—C18—H18	118.8
O3—Sn1—C33	104.1 (3)	C17—C18—H18	118.8
O1—Sn1—O2	71.11 (18)	C20—C19—Sn3	117.4 (6)
O3—Sn1—O2	144.2 (2)	C20—C19—H19A	108.0
C33—Sn1—O2	92.0 (3)	Sn3—C19—H19A	108.0
O1—Sn1—C40	115.1 (3)	C20—C19—H19B	108.0
O3—Sn1—C40	100.9 (3)	Sn3—C19—H19B	108.0
C33—Sn1—C40	120.1 (4)	H19A—C19—H19B	107.2
O2—Sn1—C40	98.1 (3)	C21—C20—C25	117.3 (8)
O1—Sn2—C12	114.1 (3)	C21—C20—C19	121.8 (9)
O1—Sn2—C5	113.1 (3)	C25—C20—C19	121.0 (8)
C12—Sn2—C5	132.4 (3)	C22—C21—C20	122.4 (10)
O1—Sn2—O2	70.13 (18)	C22—C21—H21	118.8
C12—Sn2—O2	95.7 (3)	C20—C21—H21	118.8
C5—Sn2—O2	94.9 (3)	C23—C22—C21	118.6 (11)
O1—Sn2—N2	80.20 (19)	C23—C22—H22	120.7
C12—Sn2—N2	95.0 (3)	C21—C22—H22	120.7
C5—Sn2—N2	98.1 (3)	C22—C23—C24	124.0 (10)
O2—Sn2—N2	150.29 (19)	C22—C23—F3	119.5 (13)
O1—Sn3—C26	112.2 (3)	C24—C23—F3	116.5 (13)
O1—Sn3—C19	109.9 (4)	C23—C24—C25	118.1 (10)
C26—Sn3—C19	137.9 (4)	C23—C24—H24	121.0
O1—Sn3—O3	71.67 (18)	C25—C24—H24	121.0
C26—Sn3—O3	94.1 (3)	C20—C25—C24	119.6 (9)
C19—Sn3—O3	97.0 (3)	C20—C25—H25	120.2
O1—Sn3—N1	79.50 (19)	C24—C25—H25	120.2
C26—Sn3—N1	95.9 (3)	C27—C26—Sn3	114.6 (5)
C19—Sn3—N1	93.6 (3)	C27—C26—H26A	108.6
O3—Sn3—N1	151.2 (2)	Sn3—C26—H26A	108.6
C2—S2—C1	91.9 (4)	C27—C26—H26B	108.6
Sn2—O1—Sn1	113.8 (2)	Sn3—C26—H26B	108.6
Sn2—O1—Sn3	134.9 (2)	H26A—C26—H26B	107.6
Sn1—O1—Sn3	111.3 (2)	C32—C27—C28	119.9 (8)
C3—O2—Sn1	127.1 (5)	C32—C27—C26	120.7 (7)
C3—O2—Sn2	127.8 (5)	C28—C27—C26	119.4 (7)
Sn1—O2—Sn2	104.8 (2)	C27—C28—C29	119.6 (9)
C4—O3—Sn1	129.8 (5)	C27—C28—H28	120.2
C4—O3—Sn3	126.5 (5)	C29—C28—H28	120.2
Sn1—O3—Sn3	103.6 (2)	C30—C29—C28	119.6 (9)
C1—N1—N2	114.5 (6)	C30—C29—H29	120.2
C1—N1—Sn3	121.9 (5)	C28—C29—H29	120.2
N2—N1—Sn3	123.6 (4)	F4—C30—C29	120.6 (10)
C2—N2—N1	114.3 (6)	F4—C30—C31	118.0 (11)
C2—N2—Sn2	123.9 (5)	C29—C30—C31	121.4 (9)
N1—N2—Sn2	121.5 (4)	C32—C31—C30	118.7 (9)
N1—C1—S1	124.3 (6)	C32—C31—H31	120.7
N1—C1—S2	109.7 (5)	C30—C31—H31	120.7
S1—C1—S2	126.0 (5)	C27—C32—C31	120.9 (9)
N2—C2—S3	123.6 (6)	C27—C32—H32	119.6
N2—C2—S2	109.6 (5)	C31—C32—H32	119.6
S3—C2—S2	126.8 (4)	C34—C33—Sn1	120.9 (6)
O2—C3—H3A	109.5	C34—C33—H33A	107.1
O2—C3—H3B	109.5	Sn1—C33—H33A	107.1
H3A—C3—H3B	109.5	C34—C33—H33B	107.1
O2—C3—H3C	109.5	Sn1—C33—H33B	107.1
H3A—C3—H3C	109.5	H33A—C33—H33B	106.8
H3B—C3—H3C	109.5	C39—C34—C35	117.0 (9)
O3—C4—H4A	109.5	C39—C34—C33	120.3 (9)
O3—C4—H4B	109.5	C35—C34—C33	122.5 (10)
H4A—C4—H4B	109.5	C36—C35—C34	121.4 (9)
O3—C4—H4C	109.5	C36—C35—H35	119.3
H4A—C4—H4C	109.5	C34—C35—H35	119.3
H4B—C4—H4C	109.5	C37—C36—C35	119.1 (9)
C6—C5—Sn2	112.1 (5)	C37—C36—H36	120.4
C6—C5—H5A	109.2	C35—C36—H36	120.4
Sn2—C5—H5A	109.2	C38—C37—C36	122.5 (10)
C6—C5—H5B	109.2	C38—C37—F5	118.1 (11)
Sn2—C5—H5B	109.2	C36—C37—F5	119.4 (11)
H5A—C5—H5B	107.9	C37—C38—C39	118.6 (10)
C11—C6—C7	116.7 (7)	C37—C38—H38	120.7
C11—C6—C5	123.9 (7)	C39—C38—H38	120.7
C7—C6—C5	119.3 (7)	C34—C39—C38	121.3 (10)
C8—C7—C6	120.6 (8)	C34—C39—H39	119.3
C8—C7—H7	119.7	C38—C39—H39	119.3
C6—C7—H7	119.7	C41—C40—Sn1	113.2 (5)
C9—C8—C7	119.6 (9)	C41—C40—H40A	108.9
C9—C8—H8	120.2	Sn1—C40—H40A	108.9
C7—C8—H8	120.2	C41—C40—H40B	108.9
C8—C9—C10	121.1 (8)	Sn1—C40—H40B	108.9
C8—C9—F1	119.3 (9)	H40A—C40—H40B	107.8
C10—C9—F1	119.6 (9)	C42—C41—C46	116.4 (8)
C9—C10—C11	119.6 (9)	C42—C41—C40	121.3 (8)
C9—C10—H10	120.2	C46—C41—C40	122.3 (8)
C11—C10—H10	120.2	C43—C42—C41	122.0 (9)
C10—C11—C6	122.3 (8)	C43—C42—H42	119.0
C10—C11—H11	118.9	C41—C42—H42	119.0
C6—C11—H11	118.9	C44—C43—C42	118.4 (10)
C13—C12—Sn2	112.0 (5)	C44—C43—H43	120.8
C13—C12—H12A	109.2	C42—C43—H43	120.8
Sn2—C12—H12A	109.2	C45—C44—C43	123.2 (10)
C13—C12—H12B	109.2	C45—C44—F6	118.4 (12)
Sn2—C12—H12B	109.2	C43—C44—F6	118.5 (12)
H12A—C12—H12B	107.9	C44—C45—C46	118.7 (10)
C18—C13—C14	117.8 (7)	C44—C45—H45	120.7
C18—C13—C12	122.0 (7)	C46—C45—H45	120.7
C14—C13—C12	120.1 (7)	C45—C46—C41	121.3 (9)
C15—C14—C13	120.0 (8)	C45—C46—H46	119.3
C15—C14—H14	120.0	C41—C46—H46	119.3
C13—C14—H14	120.0	C49^i—C47—C48	120.2 (9)
C16—C15—C14	118.7 (8)	C49^i—C47—H47	119.9
C16—C15—H15	120.7	C48—C47—H47	119.9
C14—C15—H15	120.7	C49—C48—C47	118.7 (9)
C17—C16—C15	122.8 (8)	C49—C48—H48	120.7
C17—C16—F2	119.8 (9)	C47—C48—H48	120.7
C15—C16—F2	117.4 (9)	C48—C49—C47^i	121.1 (9)
C16—C17—C18	118.3 (8)	C48—C49—H49	119.4
C16—C17—H17	120.9	C47^i—C49—H49	119.4
C18—C17—H17	120.9
C12—Sn2—O1—Sn1	90.6 (3)	Sn2—C5—C6—C7	−86.0 (8)
C5—Sn2—O1—Sn1	−83.6 (3)	C11—C6—C7—C8	−3.7 (12)
O2—Sn2—O1—Sn1	3.2 (2)	C5—C6—C7—C8	179.8 (7)
N2—Sn2—O1—Sn1	−178.3 (3)	C6—C7—C8—C9	1.8 (13)
C12—Sn2—O1—Sn3	−88.3 (4)	C7—C8—C9—C10	1.0 (14)
C5—Sn2—O1—Sn3	97.5 (4)	C7—C8—C9—F1	179.6 (8)
O2—Sn2—O1—Sn3	−175.7 (4)	C8—C9—C10—C11	−1.7 (14)
N2—Sn2—O1—Sn3	2.8 (3)	F1—C9—C10—C11	179.7 (8)
O3—Sn1—O1—Sn2	−178.6 (3)	C9—C10—C11—C6	−0.4 (13)
C33—Sn1—O1—Sn2	−82.6 (4)	C7—C6—C11—C10	3.0 (12)
O2—Sn1—O1—Sn2	−3.3 (2)	C5—C6—C11—C10	179.4 (7)
C40—Sn1—O1—Sn2	87.0 (4)	O1—Sn2—C12—C13	15.3 (7)
O3—Sn1—O1—Sn3	0.6 (2)	C5—Sn2—C12—C13	−171.9 (5)
C33—Sn1—O1—Sn3	96.6 (4)	O2—Sn2—C12—C13	86.1 (6)
O2—Sn1—O1—Sn3	175.9 (3)	N2—Sn2—C12—C13	−66.2 (6)
C40—Sn1—O1—Sn3	−93.8 (4)	Sn2—C12—C13—C18	78.7 (8)
C26—Sn3—O1—Sn2	91.4 (4)	Sn2—C12—C13—C14	−98.4 (8)
C19—Sn3—O1—Sn2	−90.7 (4)	C18—C13—C14—C15	1.5 (12)
O3—Sn3—O1—Sn2	178.4 (4)	C12—C13—C14—C15	178.6 (8)
N1—Sn3—O1—Sn2	−0.7 (3)	C13—C14—C15—C16	−2.0 (14)
C26—Sn3—O1—Sn1	−87.5 (3)	C14—C15—C16—C17	2.0 (15)
C19—Sn3—O1—Sn1	90.4 (3)	C14—C15—C16—F2	−178.3 (8)
O3—Sn3—O1—Sn1	−0.6 (2)	C15—C16—C17—C18	−1.3 (13)
N1—Sn3—O1—Sn1	−179.6 (3)	F2—C16—C17—C18	178.9 (8)
O1—Sn1—O2—C3	−171.4 (7)	C14—C13—C18—C17	−0.9 (11)
O3—Sn1—O2—C3	−163.7 (6)	C12—C13—C18—C17	−178.0 (7)
C33—Sn1—O2—C3	−46.1 (7)	C16—C17—C18—C13	0.8 (12)
C40—Sn1—O2—C3	74.7 (7)	O1—Sn3—C19—C20	−101.4 (8)
O1—Sn1—O2—Sn2	2.9 (2)	C26—Sn3—C19—C20	75.6 (10)
O3—Sn1—O2—Sn2	10.6 (5)	O3—Sn3—C19—C20	−28.5 (8)
C33—Sn1—O2—Sn2	128.3 (4)	N1—Sn3—C19—C20	178.4 (8)
C40—Sn1—O2—Sn2	−111.0 (3)	Sn3—C19—C20—C21	−78.9 (10)
O1—Sn2—O2—C3	171.3 (7)	Sn3—C19—C20—C25	102.9 (9)
C12—Sn2—O2—C3	57.8 (7)	C25—C20—C21—C22	−0.8 (14)
C5—Sn2—O2—C3	−75.8 (7)	C19—C20—C21—C22	−179.0 (9)
N2—Sn2—O2—C3	168.3 (6)	C20—C21—C22—C23	1.5 (17)
O1—Sn2—O2—Sn1	−2.9 (2)	C21—C22—C23—C24	−1.0 (19)
C12—Sn2—O2—Sn1	−116.5 (3)	C21—C22—C23—F3	178.0 (10)
C5—Sn2—O2—Sn1	109.9 (3)	C22—C23—C24—C25	−0.1 (18)
N2—Sn2—O2—Sn1	−6.0 (5)	F3—C23—C24—C25	−179.1 (9)
O1—Sn1—O3—C4	−178.4 (7)	C21—C20—C25—C24	−0.3 (13)
C33—Sn1—O3—C4	59.9 (7)	C19—C20—C25—C24	177.9 (8)
O2—Sn1—O3—C4	174.0 (6)	C23—C24—C25—C20	0.8 (15)
C40—Sn1—O3—C4	−65.2 (7)	O1—Sn3—C26—C27	129.7 (5)
O1—Sn1—O3—Sn3	−0.52 (19)	C19—Sn3—C26—C27	−47.3 (8)
C33—Sn1—O3—Sn3	−122.2 (3)	O3—Sn3—C26—C27	57.9 (6)
O2—Sn1—O3—Sn3	−8.1 (5)	N1—Sn3—C26—C27	−149.2 (6)
C40—Sn1—O3—Sn3	112.7 (3)	Sn3—C26—C27—C32	67.6 (9)
O1—Sn3—O3—C4	178.5 (6)	Sn3—C26—C27—C28	−111.9 (7)
C26—Sn3—O3—C4	−69.5 (6)	C32—C27—C28—C29	0.9 (12)
C19—Sn3—O3—C4	69.8 (7)	C26—C27—C28—C29	−179.7 (8)
N1—Sn3—O3—C4	−179.7 (5)	C27—C28—C29—C30	−1.0 (14)
O1—Sn3—O3—Sn1	0.5 (2)	C28—C29—C30—F4	180.0 (9)
C26—Sn3—O3—Sn1	112.6 (3)	C28—C29—C30—C31	0.9 (15)
C19—Sn3—O3—Sn1	−108.2 (4)	F4—C30—C31—C32	−179.6 (9)
N1—Sn3—O3—Sn1	2.4 (6)	C29—C30—C31—C32	−0.5 (15)
O1—Sn3—N1—C1	177.6 (6)	C28—C27—C32—C31	−0.5 (13)
C26—Sn3—N1—C1	66.1 (6)	C26—C27—C32—C31	−179.9 (8)
C19—Sn3—N1—C1	−72.8 (6)	C30—C31—C32—C27	0.3 (14)
O3—Sn3—N1—C1	175.8 (5)	O1—Sn1—C33—C34	−102.5 (9)
O1—Sn3—N1—N2	−3.7 (5)	O3—Sn1—C33—C34	−23.2 (10)
C26—Sn3—N1—N2	−115.2 (5)	O2—Sn1—C33—C34	−170.9 (9)
C19—Sn3—N1—N2	105.9 (6)	C40—Sn1—C33—C34	88.5 (10)
O3—Sn3—N1—N2	−5.5 (8)	Sn1—C33—C34—C39	116.1 (9)
C1—N1—N2—C2	−0.4 (9)	Sn1—C33—C34—C35	−70.0 (12)
Sn3—N1—N2—C2	−179.2 (5)	C39—C34—C35—C36	−1.1 (15)
C1—N1—N2—Sn2	−174.6 (5)	C33—C34—C35—C36	−175.1 (9)
Sn3—N1—N2—Sn2	6.6 (7)	C34—C35—C36—C37	1.7 (16)
O1—Sn2—N2—C2	−178.7 (6)	C35—C36—C37—C38	−2.8 (17)
C12—Sn2—N2—C2	−65.0 (6)	C35—C36—C37—F5	178.9 (9)
C5—Sn2—N2—C2	69.1 (6)	C36—C37—C38—C39	3.2 (19)
O2—Sn2—N2—C2	−175.8 (5)	F5—C37—C38—C39	−178.5 (10)
O1—Sn2—N2—N1	−5.1 (5)	C35—C34—C39—C38	1.5 (16)
C12—Sn2—N2—N1	108.5 (5)	C33—C34—C39—C38	175.7 (10)
C5—Sn2—N2—N1	−117.3 (5)	C37—C38—C39—C34	−2.5 (19)
O2—Sn2—N2—N1	−2.2 (8)	O1—Sn1—C40—C41	160.7 (6)
N2—N1—C1—S1	179.8 (5)	O3—Sn1—C40—C41	84.1 (7)
Sn3—N1—C1—S1	−1.4 (9)	C33—Sn1—C40—C41	−29.3 (8)
N2—N1—C1—S2	0.0 (8)	O2—Sn1—C40—C41	−126.4 (6)
Sn3—N1—C1—S2	178.8 (3)	Sn1—C40—C41—C42	86.6 (9)
C2—S2—C1—N1	0.3 (6)	Sn1—C40—C41—C46	−91.9 (8)
C2—S2—C1—S1	−179.5 (6)	C46—C41—C42—C43	−1.8 (13)
N1—N2—C2—S3	179.9 (5)	C40—C41—C42—C43	179.7 (8)
Sn2—N2—C2—S3	−6.1 (9)	C41—C42—C43—C44	1.0 (15)
N1—N2—C2—S2	0.6 (8)	C42—C43—C44—C45	0.3 (16)
Sn2—N2—C2—S2	174.6 (3)	C42—C43—C44—F6	−178.9 (9)
C1—S2—C2—N2	−0.5 (6)	C43—C44—C45—C46	−0.6 (16)
C1—S2—C2—S3	−179.7 (6)	F6—C44—C45—C46	178.6 (9)
O1—Sn2—C5—C6	−29.7 (7)	C44—C45—C46—C41	−0.3 (15)
C12—Sn2—C5—C6	157.5 (5)	C42—C41—C46—C45	1.5 (12)
O2—Sn2—C5—C6	−100.2 (6)	C40—C41—C46—C45	180.0 (8)
N2—Sn2—C5—C6	53.1 (6)	C49^i—C47—C48—C49	−0.1 (15)
Sn2—C5—C6—C11	97.7 (8)	C47—C48—C49—C47^i	0.1 (15)

Symmetry code: (i) −x+1, −y+2, −z+1.