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Acta Cryst. (2007). E63, m2161    [ doi:10.1107/S1600536807033715 ]

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

J.-H. Zhang, C.-L. Ma and R.-F. Zhang

Abstract top

The title complex, [Sn3(C7H7F)6(CH3O)2(C2N2S3)O]·0.5C6H6, contains a unique [mu]3-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.

Comment top

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 top

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).

Experimental top

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%.

Refinement top

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 Uiso(H) values were set at 1.5Ueq(C) for all H atoms.

Computing details top

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 top
[Figure 1] Fig. 1. The structure of the title complex (I), showing 30% probability displacement ellipsoids.
[Figure 2] 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 top
Crystal data top
[Sn3(C7H7F)6(CH3O)2(C2N2S3)O]·0.5C6H6F(000) = 2516
Mr = 1276.12Dx = 1.702 Mg m−3
Monoclinic, P21/cMelting point: 356 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.3309 (9) ÅCell parameters from 9782 reflections
b = 45.937 (4) Åθ = 1.8–26.0°
c = 13.5763 (8) ŵ = 1.68 mm−1
β = 129.394 (4)°T = 293 K
V = 4979.1 (7) Å3Block, colorless
Z = 40.18 × 0.16 × 0.08 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer		9782 independent reflections
Radiation source: fine-focus sealed tube8279 reflections with I > 2σ(I)
graphiteRint = 0.048
φ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.751, Tmax = 0.877k = −56→56
51752 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.123P)2 + 12.502P]
where P = (Fo2 + 2Fc2)/3
9782 reflections(Δ/σ)max = 0.003
591 parametersΔρmax = 0.72 e Å−3
0 restraintsΔρmin = −1.78 e Å−3
Crystal data top
[Sn3(C7H7F)6(CH3O)2(C2N2S3)O]·0.5C6H6V = 4979.1 (7) Å3
Mr = 1276.12Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3309 (9) ŵ = 1.68 mm−1
b = 45.937 (4) ÅT = 293 K
c = 13.5763 (8) Å0.18 × 0.16 × 0.08 mm
β = 129.394 (4)°
Data collection top
Siemens SMART CCD area-detector
diffractometer		9782 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		8279 reflections with I > 2σ(I)
Tmin = 0.751, Tmax = 0.877Rint = 0.048
51752 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.123P)2 + 12.502P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.184Δρmax = 0.72 e Å−3
S = 1.01Δρmin = −1.78 e Å−3
9782 reflectionsAbsolute structure: ?
591 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
Special details top

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 (Å2) top
xyzUiso*/Ueq
Sn11.09057 (6)0.872437 (11)0.26253 (5)0.04148 (16)
Sn20.99142 (6)0.942464 (10)0.27698 (4)0.03669 (15)
Sn30.68330 (6)0.880017 (10)0.12982 (5)0.03655 (15)
S10.2941 (3)0.90904 (5)0.0062 (3)0.0677 (6)
S20.4469 (3)0.96904 (4)0.1112 (2)0.0548 (5)
S30.7698 (3)1.00416 (5)0.2581 (2)0.0594 (5)
F10.8398 (10)0.88068 (14)0.6454 (7)0.094 (2)
F20.5363 (10)0.91417 (15)−0.3438 (5)0.104 (2)
F30.7676 (14)0.74570 (16)0.3886 (12)0.152 (4)
F40.2991 (11)0.76864 (14)−0.2917 (7)0.112 (3)
F50.9696 (12)0.77323 (17)−0.1815 (9)0.125 (3)
F61.5752 (11)0.75227 (17)0.4952 (8)0.120 (3)
O10.9093 (5)0.90072 (10)0.2213 (4)0.0384 (10)
O21.1931 (6)0.91524 (11)0.3167 (5)0.0492 (13)
O30.8669 (6)0.84801 (11)0.1676 (5)0.0456 (12)
N10.6135 (7)0.92511 (12)0.1374 (6)0.0386 (13)
N20.7269 (7)0.94780 (12)0.1975 (5)0.0380 (12)
C10.4561 (10)0.93234 (17)0.0851 (8)0.0454 (17)
C20.6593 (9)0.97345 (16)0.1925 (7)0.0440 (16)
C31.3556 (10)0.9245 (2)0.3585 (10)0.065 (2)
H3A1.42850.90800.38850.097*
H3B1.40330.93850.42620.097*
H3C1.34230.93330.28830.097*
C40.8373 (12)0.81699 (16)0.1369 (8)0.056 (2)
H4A0.82310.81350.06080.084*
H4B0.73810.81110.12360.084*
H4C0.93140.80600.20610.084*
C51.1099 (11)0.95023 (19)0.4733 (7)0.054 (2)
H5A1.22920.94670.52470.065*
H5B1.09430.97050.48410.065*
C61.0403 (9)0.93103 (17)0.5198 (6)0.0423 (16)
C70.8973 (11)0.93993 (18)0.5021 (8)0.0502 (18)
H70.84680.95760.46220.060*
C80.8298 (12)0.9226 (2)0.5436 (9)0.063 (2)
H80.73300.92840.52940.076*
C90.9057 (13)0.8974 (2)0.6044 (8)0.062 (2)
C101.0485 (13)0.8888 (2)0.6276 (8)0.064 (2)
H101.10110.87160.67160.077*
C111.1143 (10)0.9055 (2)0.5860 (7)0.056 (2)
H111.21260.89950.60290.067*
C120.9649 (11)0.96861 (18)0.1346 (7)0.0516 (19)
H12A0.92170.98760.13200.062*
H12B1.07410.97140.15740.062*
C130.8495 (9)0.95493 (15)0.0050 (7)0.0399 (15)
C140.9149 (11)0.9391 (2)−0.0428 (8)0.057 (2)
H141.03020.93750.00510.068*
C150.8075 (14)0.9260 (2)−0.1618 (9)0.068 (3)
H150.84980.9159−0.19550.082*
C160.6388 (13)0.9280 (2)−0.2283 (7)0.061 (2)
C170.5720 (11)0.94291 (17)−0.1855 (8)0.053 (2)
H170.45640.9443−0.23380.064*
C180.6791 (10)0.95621 (16)−0.0677 (7)0.0450 (17)
H180.63370.9664−0.03680.054*
C190.6611 (15)0.8640 (2)0.2674 (11)0.070 (3)
H19A0.73860.87490.34580.084*
H19B0.54890.86840.23640.084*
C200.6921 (10)0.83251 (17)0.2988 (7)0.0452 (17)
C210.5731 (12)0.8119 (2)0.2202 (9)0.067 (2)
H210.47120.81780.14470.081*
C220.5989 (17)0.7829 (2)0.2487 (14)0.086 (3)
H220.51720.76930.19280.104*
C230.7414 (18)0.7745 (2)0.3566 (15)0.084 (3)
C240.8651 (14)0.7927 (3)0.4403 (12)0.082 (3)
H240.96410.78580.51570.099*
C250.8414 (11)0.8229 (2)0.4110 (9)0.069 (3)
H250.92570.83610.46690.082*
C260.5420 (11)0.87894 (17)−0.0712 (7)0.0494 (18)
H26A0.44790.8922−0.11010.059*
H26B0.61180.8860−0.09070.059*
C270.4760 (9)0.84916 (16)−0.1307 (7)0.0440 (16)
C280.5399 (12)0.8352 (2)−0.1822 (8)0.058 (2)
H280.62290.8440−0.17980.069*
C290.4788 (13)0.8078 (2)−0.2377 (8)0.066 (2)
H290.51960.7984−0.27370.079*
C300.3596 (15)0.7950 (2)−0.2388 (9)0.073 (3)
C310.2951 (13)0.8087 (2)−0.1873 (9)0.069 (2)
H310.21280.7997−0.18910.082*
C320.3555 (10)0.83586 (18)−0.1331 (8)0.0534 (19)
H320.31360.8453−0.09790.064*
C331.1616 (14)0.8670 (2)0.1472 (10)0.0653 (18)
H33A1.12570.88430.09470.078*
H33B1.28300.86680.20380.078*
C341.1027 (13)0.8414 (2)0.0609 (10)0.0653 (18)
C351.1589 (13)0.8136 (2)0.1060 (9)0.066 (2)
H351.22990.81020.19340.079*
C361.1128 (14)0.7909 (2)0.0253 (11)0.074 (3)
H361.14930.77210.05690.089*
C371.0143 (14)0.7959 (2)−0.0998 (11)0.073 (3)
C380.9535 (16)0.8222 (3)−0.1497 (11)0.089 (3)
H380.88080.8249−0.23750.107*
C391.0005 (14)0.8453 (2)−0.0687 (10)0.072 (3)
H390.96230.8639−0.10240.087*
C401.2385 (11)0.8535 (2)0.4489 (8)0.060 (2)
H40A1.32070.86760.51050.072*
H40B1.16640.84900.46950.072*
C411.3267 (10)0.82649 (17)0.4604 (7)0.0479 (17)
C421.4822 (11)0.8276 (2)0.4905 (9)0.062 (2)
H421.53160.84560.50310.075*
C431.5658 (13)0.8028 (3)0.5021 (10)0.077 (3)
H431.67090.80400.52360.092*
C441.4915 (17)0.7767 (3)0.4816 (10)0.080 (3)
C451.3412 (15)0.7739 (2)0.4501 (10)0.079 (3)
H451.29370.75560.43590.095*
C461.2565 (12)0.7988 (2)0.4388 (8)0.062 (2)
H461.15110.79710.41640.074*
C470.5586 (14)1.0005 (2)0.4335 (10)0.069 (3)
H470.59761.00090.38780.082*
C480.6669 (13)0.99371 (17)0.5618 (10)0.060 (2)
H480.77870.98950.60310.072*
C490.6062 (14)0.9934 (2)0.6267 (9)0.070 (3)
H490.67800.98890.71310.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0409 (3)0.0400 (3)0.0480 (3)0.0006 (2)0.0303 (2)−0.0030 (2)
Sn20.0393 (3)0.0357 (3)0.0343 (3)−0.00752 (19)0.0230 (2)−0.00782 (18)
Sn30.0391 (3)0.0312 (3)0.0435 (3)−0.00509 (18)0.0282 (2)−0.00437 (18)
S10.0481 (11)0.0596 (13)0.1021 (19)−0.0090 (10)0.0509 (13)−0.0123 (12)
S20.0542 (11)0.0422 (10)0.0713 (14)0.0074 (9)0.0413 (11)−0.0030 (9)
S30.0691 (14)0.0409 (10)0.0666 (13)−0.0066 (9)0.0423 (12)−0.0162 (9)
F10.134 (6)0.089 (4)0.103 (5)−0.019 (4)0.096 (5)0.004 (4)
F20.127 (6)0.101 (5)0.041 (3)−0.002 (4)0.033 (3)−0.019 (3)
F30.208 (10)0.067 (5)0.267 (12)0.047 (5)0.190 (10)0.052 (6)
F40.156 (7)0.060 (4)0.091 (5)−0.026 (4)0.065 (5)−0.032 (3)
F50.171 (8)0.099 (5)0.151 (7)−0.044 (5)0.123 (7)−0.065 (5)
F60.142 (7)0.101 (5)0.115 (6)0.059 (5)0.080 (5)0.009 (4)
O10.033 (2)0.032 (2)0.045 (3)−0.0005 (18)0.022 (2)−0.0051 (19)
O20.037 (3)0.050 (3)0.062 (3)−0.009 (2)0.032 (3)−0.015 (3)
O30.046 (3)0.035 (3)0.062 (3)−0.003 (2)0.037 (3)−0.005 (2)
N10.041 (3)0.034 (3)0.052 (3)−0.001 (2)0.035 (3)−0.004 (2)
N20.037 (3)0.035 (3)0.039 (3)−0.002 (2)0.023 (3)−0.007 (2)
C10.047 (4)0.044 (4)0.059 (5)0.001 (3)0.040 (4)0.003 (3)
C20.048 (4)0.042 (4)0.045 (4)0.003 (3)0.031 (4)−0.006 (3)
C30.044 (4)0.066 (6)0.092 (7)−0.005 (4)0.047 (5)−0.005 (5)
C40.069 (5)0.036 (4)0.062 (5)0.016 (4)0.041 (5)−0.001 (4)
C50.057 (5)0.061 (5)0.040 (4)−0.013 (4)0.028 (4)−0.017 (4)
C60.042 (4)0.052 (4)0.028 (3)−0.002 (3)0.020 (3)−0.008 (3)
C70.057 (5)0.052 (5)0.048 (4)0.003 (4)0.037 (4)0.002 (3)
C80.065 (5)0.081 (6)0.064 (5)0.000 (5)0.050 (5)−0.002 (5)
C90.086 (7)0.058 (5)0.053 (5)−0.013 (5)0.049 (5)−0.001 (4)
C100.079 (6)0.054 (5)0.050 (5)0.006 (5)0.037 (5)0.005 (4)
C110.046 (4)0.072 (6)0.035 (4)0.004 (4)0.019 (4)0.000 (4)
C120.058 (5)0.050 (4)0.050 (4)−0.005 (4)0.036 (4)0.003 (4)
C130.049 (4)0.036 (3)0.040 (4)0.006 (3)0.031 (3)0.005 (3)
C140.054 (5)0.074 (6)0.044 (4)0.020 (4)0.032 (4)0.008 (4)
C150.099 (8)0.070 (6)0.052 (5)0.028 (5)0.056 (6)0.007 (4)
C160.076 (6)0.055 (5)0.032 (4)0.006 (4)0.025 (4)0.003 (3)
C170.046 (4)0.049 (5)0.045 (4)0.005 (3)0.019 (4)0.014 (3)
C180.053 (4)0.043 (4)0.050 (4)0.009 (3)0.038 (4)0.007 (3)
C190.103 (8)0.062 (6)0.088 (7)0.010 (5)0.080 (7)0.012 (5)
C200.054 (4)0.046 (4)0.053 (4)−0.007 (3)0.042 (4)−0.002 (3)
C210.055 (5)0.073 (6)0.058 (5)−0.017 (5)0.029 (4)0.002 (5)
C220.101 (9)0.062 (7)0.124 (10)−0.026 (6)0.085 (9)−0.014 (7)
C230.105 (9)0.051 (6)0.141 (11)0.010 (6)0.099 (9)0.022 (7)
C240.069 (6)0.092 (8)0.105 (8)0.033 (6)0.064 (7)0.049 (7)
C250.050 (5)0.085 (7)0.065 (6)−0.019 (5)0.034 (5)−0.005 (5)
C260.057 (5)0.045 (4)0.044 (4)−0.007 (3)0.032 (4)−0.001 (3)
C270.043 (4)0.043 (4)0.038 (4)−0.003 (3)0.022 (3)−0.002 (3)
C280.064 (5)0.066 (5)0.050 (5)0.002 (4)0.039 (4)−0.005 (4)
C290.086 (7)0.062 (6)0.047 (5)0.007 (5)0.040 (5)−0.007 (4)
C300.099 (8)0.046 (5)0.054 (5)−0.004 (5)0.039 (6)−0.013 (4)
C310.068 (6)0.057 (5)0.065 (6)−0.016 (5)0.035 (5)−0.009 (4)
C320.052 (4)0.050 (4)0.050 (4)−0.008 (4)0.028 (4)−0.006 (4)
C330.087 (5)0.062 (4)0.088 (5)−0.019 (3)0.075 (4)−0.016 (3)
C340.087 (5)0.062 (4)0.088 (5)−0.019 (3)0.075 (4)−0.016 (3)
C350.078 (6)0.073 (6)0.056 (5)0.014 (5)0.047 (5)0.011 (4)
C360.098 (8)0.050 (5)0.104 (8)0.020 (5)0.078 (7)0.017 (5)
C370.081 (7)0.071 (6)0.092 (8)−0.018 (5)0.066 (7)−0.027 (6)
C380.094 (8)0.101 (9)0.054 (6)0.001 (7)0.038 (6)−0.001 (6)
C390.089 (7)0.061 (6)0.070 (6)0.022 (5)0.052 (6)0.022 (5)
C400.060 (5)0.071 (6)0.048 (5)0.008 (4)0.034 (4)−0.002 (4)
C410.051 (4)0.052 (5)0.038 (4)0.005 (3)0.027 (4)0.006 (3)
C420.049 (5)0.074 (6)0.059 (5)−0.007 (4)0.032 (4)−0.005 (4)
C430.053 (5)0.101 (9)0.072 (6)0.019 (5)0.038 (5)−0.004 (6)
C440.101 (9)0.072 (7)0.056 (6)0.033 (6)0.045 (6)0.003 (5)
C450.090 (8)0.051 (5)0.067 (6)−0.003 (5)0.036 (6)0.000 (5)
C460.063 (5)0.078 (6)0.043 (4)0.006 (5)0.032 (4)0.008 (4)
C470.090 (7)0.057 (5)0.087 (7)−0.032 (5)0.069 (6)−0.022 (5)
C480.070 (6)0.039 (4)0.083 (7)−0.005 (4)0.054 (5)−0.003 (4)
C490.080 (7)0.061 (6)0.057 (5)−0.015 (5)0.037 (5)0.000 (4)
Geometric parameters (Å, °) top
Sn1—O12.044 (4)C18—H180.9300
Sn1—O32.116 (5)C19—C201.486 (12)
Sn1—C332.125 (8)C19—H19A0.9700
Sn1—O22.131 (5)C19—H19B0.9700
Sn1—C402.142 (9)C20—C211.373 (12)
Sn2—O12.038 (5)C20—C251.383 (12)
Sn2—C122.141 (7)C21—C221.366 (15)
Sn2—C52.142 (7)C21—H210.9300
Sn2—O22.184 (5)C22—C231.312 (17)
Sn2—N22.225 (6)C22—H220.9300
Sn3—O12.054 (4)C23—C241.334 (18)
Sn3—C262.127 (8)C24—C251.419 (15)
Sn3—C192.150 (8)C24—H240.9300
Sn3—O32.188 (5)C25—H250.9300
Sn3—N12.217 (5)C26—C271.513 (10)
S1—C11.679 (8)C26—H26A0.9700
S2—C21.732 (8)C26—H26B0.9700
S2—C11.738 (8)C27—C321.369 (11)
S3—C21.672 (8)C27—C281.386 (11)
F1—C91.358 (10)C28—C291.394 (13)
F2—C161.370 (10)C28—H280.9300
F3—C231.367 (12)C29—C301.357 (15)
F4—C301.342 (11)C29—H290.9300
F5—C371.371 (11)C30—C311.386 (15)
F6—C441.357 (11)C31—C321.381 (12)
O2—C31.454 (9)C31—H310.9300
O3—C41.462 (9)C32—H320.9300
N1—C11.339 (9)C33—C341.488 (12)
N1—N21.382 (8)C33—H33A0.9700
N2—C21.349 (9)C33—H33B0.9700
C3—H3A0.9600C34—C391.373 (14)
C3—H3B0.9600C34—C351.377 (13)
C3—H3C0.9600C35—C361.360 (14)
C4—H4A0.9600C35—H350.9300
C4—H4B0.9600C36—C371.334 (15)
C4—H4C0.9600C36—H360.9300
C5—C61.506 (11)C37—C381.331 (16)
C5—H5A0.9700C38—C391.375 (15)
C5—H5B0.9700C38—H380.9300
C6—C111.376 (12)C39—H390.9300
C6—C71.399 (11)C40—C411.487 (12)
C7—C81.390 (12)C40—H40A0.9700
C7—H70.9300C40—H40B0.9700
C8—C91.348 (13)C41—C421.385 (12)
C8—H80.9300C41—C461.399 (12)
C9—C101.357 (14)C42—C431.375 (14)
C10—C111.363 (13)C42—H420.9300
C10—H100.9300C43—C441.353 (17)
C11—H110.9300C43—H430.9300
C12—C131.500 (11)C44—C451.330 (16)
C12—H12A0.9700C45—C461.389 (14)
C12—H12B0.9700C45—H450.9300
C13—C181.368 (10)C46—H460.9300
C13—C141.400 (10)C47—C49i1.372 (15)
C14—C151.391 (13)C47—C481.381 (14)
C14—H140.9300C47—H470.9300
C15—C161.366 (14)C48—C491.368 (13)
C15—H150.9300C48—H480.9300
C16—C171.338 (13)C49—C47i1.372 (15)
C17—C181.382 (11)C49—H490.9300
C17—H170.9300
O1—Sn1—O373.36 (18)C13—C18—C17122.3 (7)
O1—Sn1—C33123.9 (3)C13—C18—H18118.8
O3—Sn1—C33104.1 (3)C17—C18—H18118.8
O1—Sn1—O271.11 (18)C20—C19—Sn3117.4 (6)
O3—Sn1—O2144.2 (2)C20—C19—H19A108.0
C33—Sn1—O292.0 (3)Sn3—C19—H19A108.0
O1—Sn1—C40115.1 (3)C20—C19—H19B108.0
O3—Sn1—C40100.9 (3)Sn3—C19—H19B108.0
C33—Sn1—C40120.1 (4)H19A—C19—H19B107.2
O2—Sn1—C4098.1 (3)C21—C20—C25117.3 (8)
O1—Sn2—C12114.1 (3)C21—C20—C19121.8 (9)
O1—Sn2—C5113.1 (3)C25—C20—C19121.0 (8)
C12—Sn2—C5132.4 (3)C22—C21—C20122.4 (10)
O1—Sn2—O270.13 (18)C22—C21—H21118.8
C12—Sn2—O295.7 (3)C20—C21—H21118.8
C5—Sn2—O294.9 (3)C23—C22—C21118.6 (11)
O1—Sn2—N280.20 (19)C23—C22—H22120.7
C12—Sn2—N295.0 (3)C21—C22—H22120.7
C5—Sn2—N298.1 (3)C22—C23—C24124.0 (10)
O2—Sn2—N2150.29 (19)C22—C23—F3119.5 (13)
O1—Sn3—C26112.2 (3)C24—C23—F3116.5 (13)
O1—Sn3—C19109.9 (4)C23—C24—C25118.1 (10)
C26—Sn3—C19137.9 (4)C23—C24—H24121.0
O1—Sn3—O371.67 (18)C25—C24—H24121.0
C26—Sn3—O394.1 (3)C20—C25—C24119.6 (9)
C19—Sn3—O397.0 (3)C20—C25—H25120.2
O1—Sn3—N179.50 (19)C24—C25—H25120.2
C26—Sn3—N195.9 (3)C27—C26—Sn3114.6 (5)
C19—Sn3—N193.6 (3)C27—C26—H26A108.6
O3—Sn3—N1151.2 (2)Sn3—C26—H26A108.6
C2—S2—C191.9 (4)C27—C26—H26B108.6
Sn2—O1—Sn1113.8 (2)Sn3—C26—H26B108.6
Sn2—O1—Sn3134.9 (2)H26A—C26—H26B107.6
Sn1—O1—Sn3111.3 (2)C32—C27—C28119.9 (8)
C3—O2—Sn1127.1 (5)C32—C27—C26120.7 (7)
C3—O2—Sn2127.8 (5)C28—C27—C26119.4 (7)
Sn1—O2—Sn2104.8 (2)C27—C28—C29119.6 (9)
C4—O3—Sn1129.8 (5)C27—C28—H28120.2
C4—O3—Sn3126.5 (5)C29—C28—H28120.2
Sn1—O3—Sn3103.6 (2)C30—C29—C28119.6 (9)
C1—N1—N2114.5 (6)C30—C29—H29120.2
C1—N1—Sn3121.9 (5)C28—C29—H29120.2
N2—N1—Sn3123.6 (4)F4—C30—C29120.6 (10)
C2—N2—N1114.3 (6)F4—C30—C31118.0 (11)
C2—N2—Sn2123.9 (5)C29—C30—C31121.4 (9)
N1—N2—Sn2121.5 (4)C32—C31—C30118.7 (9)
N1—C1—S1124.3 (6)C32—C31—H31120.7
N1—C1—S2109.7 (5)C30—C31—H31120.7
S1—C1—S2126.0 (5)C27—C32—C31120.9 (9)
N2—C2—S3123.6 (6)C27—C32—H32119.6
N2—C2—S2109.6 (5)C31—C32—H32119.6
S3—C2—S2126.8 (4)C34—C33—Sn1120.9 (6)
O2—C3—H3A109.5C34—C33—H33A107.1
O2—C3—H3B109.5Sn1—C33—H33A107.1
H3A—C3—H3B109.5C34—C33—H33B107.1
O2—C3—H3C109.5Sn1—C33—H33B107.1
H3A—C3—H3C109.5H33A—C33—H33B106.8
H3B—C3—H3C109.5C39—C34—C35117.0 (9)
O3—C4—H4A109.5C39—C34—C33120.3 (9)
O3—C4—H4B109.5C35—C34—C33122.5 (10)
H4A—C4—H4B109.5C36—C35—C34121.4 (9)
O3—C4—H4C109.5C36—C35—H35119.3
H4A—C4—H4C109.5C34—C35—H35119.3
H4B—C4—H4C109.5C37—C36—C35119.1 (9)
C6—C5—Sn2112.1 (5)C37—C36—H36120.4
C6—C5—H5A109.2C35—C36—H36120.4
Sn2—C5—H5A109.2C38—C37—C36122.5 (10)
C6—C5—H5B109.2C38—C37—F5118.1 (11)
Sn2—C5—H5B109.2C36—C37—F5119.4 (11)
H5A—C5—H5B107.9C37—C38—C39118.6 (10)
C11—C6—C7116.7 (7)C37—C38—H38120.7
C11—C6—C5123.9 (7)C39—C38—H38120.7
C7—C6—C5119.3 (7)C34—C39—C38121.3 (10)
C8—C7—C6120.6 (8)C34—C39—H39119.3
C8—C7—H7119.7C38—C39—H39119.3
C6—C7—H7119.7C41—C40—Sn1113.2 (5)
C9—C8—C7119.6 (9)C41—C40—H40A108.9
C9—C8—H8120.2Sn1—C40—H40A108.9
C7—C8—H8120.2C41—C40—H40B108.9
C8—C9—C10121.1 (8)Sn1—C40—H40B108.9
C8—C9—F1119.3 (9)H40A—C40—H40B107.8
C10—C9—F1119.6 (9)C42—C41—C46116.4 (8)
C9—C10—C11119.6 (9)C42—C41—C40121.3 (8)
C9—C10—H10120.2C46—C41—C40122.3 (8)
C11—C10—H10120.2C43—C42—C41122.0 (9)
C10—C11—C6122.3 (8)C43—C42—H42119.0
C10—C11—H11118.9C41—C42—H42119.0
C6—C11—H11118.9C44—C43—C42118.4 (10)
C13—C12—Sn2112.0 (5)C44—C43—H43120.8
C13—C12—H12A109.2C42—C43—H43120.8
Sn2—C12—H12A109.2C45—C44—C43123.2 (10)
C13—C12—H12B109.2C45—C44—F6118.4 (12)
Sn2—C12—H12B109.2C43—C44—F6118.5 (12)
H12A—C12—H12B107.9C44—C45—C46118.7 (10)
C18—C13—C14117.8 (7)C44—C45—H45120.7
C18—C13—C12122.0 (7)C46—C45—H45120.7
C14—C13—C12120.1 (7)C45—C46—C41121.3 (9)
C15—C14—C13120.0 (8)C45—C46—H46119.3
C15—C14—H14120.0C41—C46—H46119.3
C13—C14—H14120.0C49i—C47—C48120.2 (9)
C16—C15—C14118.7 (8)C49i—C47—H47119.9
C16—C15—H15120.7C48—C47—H47119.9
C14—C15—H15120.7C49—C48—C47118.7 (9)
C17—C16—C15122.8 (8)C49—C48—H48120.7
C17—C16—F2119.8 (9)C47—C48—H48120.7
C15—C16—F2117.4 (9)C48—C49—C47i121.1 (9)
C16—C17—C18118.3 (8)C48—C49—H49119.4
C16—C17—H17120.9C47i—C49—H49119.4
C18—C17—H17120.9
C12—Sn2—O1—Sn190.6 (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—Sn13.2 (2)C5—C6—C7—C8179.8 (7)
N2—Sn2—O1—Sn1−178.3 (3)C6—C7—C8—C91.8 (13)
C12—Sn2—O1—Sn3−88.3 (4)C7—C8—C9—C101.0 (14)
C5—Sn2—O1—Sn397.5 (4)C7—C8—C9—F1179.6 (8)
O2—Sn2—O1—Sn3−175.7 (4)C8—C9—C10—C11−1.7 (14)
N2—Sn2—O1—Sn32.8 (3)F1—C9—C10—C11179.7 (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—C103.0 (12)
O2—Sn1—O1—Sn2−3.3 (2)C5—C6—C11—C10179.4 (7)
C40—Sn1—O1—Sn287.0 (4)O1—Sn2—C12—C1315.3 (7)
O3—Sn1—O1—Sn30.6 (2)C5—Sn2—C12—C13−171.9 (5)
C33—Sn1—O1—Sn396.6 (4)O2—Sn2—C12—C1386.1 (6)
O2—Sn1—O1—Sn3175.9 (3)N2—Sn2—C12—C13−66.2 (6)
C40—Sn1—O1—Sn3−93.8 (4)Sn2—C12—C13—C1878.7 (8)
C26—Sn3—O1—Sn291.4 (4)Sn2—C12—C13—C14−98.4 (8)
C19—Sn3—O1—Sn2−90.7 (4)C18—C13—C14—C151.5 (12)
O3—Sn3—O1—Sn2178.4 (4)C12—C13—C14—C15178.6 (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—C172.0 (15)
C19—Sn3—O1—Sn190.4 (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—C18178.9 (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—C130.8 (12)
C40—Sn1—O2—C374.7 (7)O1—Sn3—C19—C20−101.4 (8)
O1—Sn1—O2—Sn22.9 (2)C26—Sn3—C19—C2075.6 (10)
O3—Sn1—O2—Sn210.6 (5)O3—Sn3—C19—C20−28.5 (8)
C33—Sn1—O2—Sn2128.3 (4)N1—Sn3—C19—C20178.4 (8)
C40—Sn1—O2—Sn2−111.0 (3)Sn3—C19—C20—C21−78.9 (10)
O1—Sn2—O2—C3171.3 (7)Sn3—C19—C20—C25102.9 (9)
C12—Sn2—O2—C357.8 (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—C3168.3 (6)C20—C21—C22—C231.5 (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—F3178.0 (10)
C5—Sn2—O2—Sn1109.9 (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—C459.9 (7)C19—C20—C25—C24177.9 (8)
O2—Sn1—O3—C4174.0 (6)C23—C24—C25—C200.8 (15)
C40—Sn1—O3—C4−65.2 (7)O1—Sn3—C26—C27129.7 (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—C2757.9 (6)
O2—Sn1—O3—Sn3−8.1 (5)N1—Sn3—C26—C27−149.2 (6)
C40—Sn1—O3—Sn3112.7 (3)Sn3—C26—C27—C3267.6 (9)
O1—Sn3—O3—C4178.5 (6)Sn3—C26—C27—C28−111.9 (7)
C26—Sn3—O3—C4−69.5 (6)C32—C27—C28—C290.9 (12)
C19—Sn3—O3—C469.8 (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—Sn10.5 (2)C28—C29—C30—F4180.0 (9)
C26—Sn3—O3—Sn1112.6 (3)C28—C29—C30—C310.9 (15)
C19—Sn3—O3—Sn1−108.2 (4)F4—C30—C31—C32−179.6 (9)
N1—Sn3—O3—Sn12.4 (6)C29—C30—C31—C32−0.5 (15)
O1—Sn3—N1—C1177.6 (6)C28—C27—C32—C31−0.5 (13)
C26—Sn3—N1—C166.1 (6)C26—C27—C32—C31−179.9 (8)
C19—Sn3—N1—C1−72.8 (6)C30—C31—C32—C270.3 (14)
O3—Sn3—N1—C1175.8 (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—N2105.9 (6)C40—Sn1—C33—C3488.5 (10)
O3—Sn3—N1—N2−5.5 (8)Sn1—C33—C34—C39116.1 (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—Sn26.6 (7)C34—C35—C36—C371.7 (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—F5178.9 (9)
C5—Sn2—N2—C269.1 (6)C36—C37—C38—C393.2 (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—C381.5 (16)
C12—Sn2—N2—N1108.5 (5)C33—C34—C39—C38175.7 (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—C41160.7 (6)
N2—N1—C1—S1179.8 (5)O3—Sn1—C40—C4184.1 (7)
Sn3—N1—C1—S1−1.4 (9)C33—Sn1—C40—C41−29.3 (8)
N2—N1—C1—S20.0 (8)O2—Sn1—C40—C41−126.4 (6)
Sn3—N1—C1—S2178.8 (3)Sn1—C40—C41—C4286.6 (9)
C2—S2—C1—N10.3 (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—S3179.9 (5)C40—C41—C42—C43179.7 (8)
Sn2—N2—C2—S3−6.1 (9)C41—C42—C43—C441.0 (15)
N1—N2—C2—S20.6 (8)C42—C43—C44—C450.3 (16)
Sn2—N2—C2—S2174.6 (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—C46178.6 (9)
O1—Sn2—C5—C6−29.7 (7)C44—C45—C46—C41−0.3 (15)
C12—Sn2—C5—C6157.5 (5)C42—C41—C46—C451.5 (12)
O2—Sn2—C5—C6−100.2 (6)C40—C41—C46—C45180.0 (8)
N2—Sn2—C5—C653.1 (6)C49i—C47—C48—C49−0.1 (15)
Sn2—C5—C6—C1197.7 (8)C47—C48—C49—C47i0.1 (15)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Acknowledgements top

We acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Liaocheng University, People's Republic of China.

references
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