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Acta Cryst. (2009). E65, m1154-m1155    [ doi:10.1107/S1600536809034114 ]

Bis(tetraphenylphosphonium) tris[N-(methylsulfonyl)dithiocarbimato(2-)-[kappa]2S,S']stannate(IV)

J. P. Barolli, M. R. L. Oliveira, R. S. Corrêa and J. Ellena

Abstract top

In the title complex, (C24H20P)2[Sn(C2H3NO2S3)3], the SnIV atom is coordinated by three N-(methylsulfonyl)dithiocarbimate bidentate ligands through the anionic S atoms in a slightly distorted octahedral coordination geometry. There is one half-molecule in the asymmetric unit; the complex is located on a crystallographic twofold rotation axis passing through the cation and bisecting one of the (non-symmetric) ligands, which appears thus disordered over two sites of equal occupancy. In the crystal structure, weak intermolecular C-H...O and C-H...S interactions contribute to the packing stabilization.

Comment top

We became interested in the syntheses and characterization of tin(IV) dithiocarbimate complexes due to their similarity with the dithiocarbamate analogues, which have shown antifungal activity (Menezes et al., 2005). Tin dithiocarbamates have also been used as molecular tin sulfide precursors for semiconductor films (Barone et al., 2002). To the best of our knowledge, the title compound is the first member of a class of Sn complexes with general formula [Sn(RSO2N=CS2)3]2-. This class is related to tin(IV) dithiocarbamates (Coucouvanis, 1979; Heard, 2005 and Seth et al., 1992). However, differently from the dithiocarbamates, these are anionic species. Some crystallographic structures of transition metal (Ni, Pt and Zn) complexes with dithiocarbimates derivated from sulfonamides are described in the literature (Alves et al.,2009; Amim et al., 2008 and Franca et al.; 2006).

The title compound, which is quite stable under ambient conditions, comprises a complex dianion and two tetraphenylphosphonium cations, with the formula (Ph4P)2[Sn(CH3SO2N=CS2)2] (scheme). To the best of our knowledge the tris(methyldithiocarbimato)estannate(IV) anion is the first example of tin complexes with dithiocarbimate ligands derived from sulfonamides. So, in this paper we report the crystal structure of the title compound. The complex presents an octahedral environment around the SnIV atom with the ligands coordinating in a relatively distorted manner (Figure 1). The Sn—S bond lengths lie within the range 2.443 (3)–2.646 (2) Å. In the chelate rings the C—S fragments present bond lengths which are characteristic of a single bond [1.75 (1)–1.77 (1) Å]. These values are in agreement with related structures (Menezes et al., 2005). One of the ligands appears disordered into two sites (arounf the twofold symmetry axis) with occupancy factor 0.5. Weak intermolecular C—H···O and C—H···S interactions contribute to packing stabilization (Table 1). Figure 2 shows a crystal packing view of the complex projected onto the bc plane, where two independent sheets are clearly visible: one of them formed by the complex (green in Figure 2) and another defined by phosphonium units (blue in Figure 2). Both sheets are linked by weak hydrogen bonds (Table 1).

Related literature top

For general background to tin(IV) dithiocarbamates, see: Barone et al. (2002); Coucouvanis (1979); Heard (2005); Menezes et al. (2005); Seth et al. (1992). For related structures of transition metal (Ni, Pt and Zn) complexes with dithiocarbimates derived from sulfonamides, see: Alves et al.(2009); Amim et al. (2008); Franca et al. (2006); Menezes et al. (2005). For the ligand synthesis, see: Hartke (1966).

Experimental top

The potassium methylsulfonyldithiocarbimate dihydrate was prepared from methanesulfonamide as described in the literature (Hartke,1966). The compound (1) was prepared in DMF (10 ml). Tin(IV) iodide (0.7 mmol) was added to a suspension of the potassium methylsulfonyldithiocarbimate dihydrate (2.1 mmol). The mixture was stirred for 1.5 h at room temperature and filtered. Water (15 ml) and tetraphenylphosphonium bromide (1.4 mmol) were added to the solution obtained. The mixture was stirred for 15 min and the solid product obtained was filtered, washed with distilled water and dried under reduced pressure for 1 day, yielding (Ph4P)2[Sn(CH3SO2N=CS2)3] (ca 70%). Suitable crystals of (1) were obtained by slow evaporation of the solution of the compound in methanol/water (1:1 v/v); m. pt 420.6–422.0 K. Analysis found: C49.69, H 3.91, N 3.04%; C54H49N3O6P2S9Sn requires: C 49.69, H 3.78, N 3.22%. IR (most important bands, cm-1): 1437 v(C=N); 1291 vass(SO2); 1127 vsim(SO2); 938 vass(CS2) and 317 v(SnS).

Refinement top

Refinement in Cc proved that the disorder around the two fold axis was not an artifact, thus confirming the correct space group as C2/c. Similarity restraints were applied to the disordered ligand in order to to ensure a reasonable geometry. H atoms were positioned geometrically and refined as riding. Caryl—H = 0.93 Å, Cmethyl—H= 0.96 Å. Uiso(H)= 1.2Ueq(Caryl) or Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: Please supply; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Structure of the complex showing atom labels, with ellipsoids drawn at the 30% probability level. One of the two moieties in the disordered ligand is presented in open bonds. For clarity, H atoms have been omitted. [Symmetry code: i= -x, y, 1/2-z].
[Figure 2] Fig. 2. Crystal packing of the title compound forming two independents sheets. The complex are displayed in green and the phosphonium in blue.
Bis(tetraphenylphosphonium) tris[N-(methylsulfonyl)dithiocarbimato(2-)- κ2S,S']stannate(IV) top
Crystal data top
(C24H20P)2[Sn(C2H3NO2S3)3]F(000) = 2664
Mr = 1305.13Dx = 1.472 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 37024 reflections
a = 18.5563 (3) Åθ = 2.9–26.4°
b = 13.6096 (2) ŵ = 0.86 mm−1
c = 23.3203 (3) ÅT = 298 K
β = 91.355 (1)°Prism, colourless
V = 5887.75 (15) Å30.40 × 0.11 × 0.07 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		4871 reflections with I > 2σ(I)
CCD rotation images, thick slices scansRint = 0.049
Absorption correction: gaussian
(Coppens et al., 1965)		θmax = 25.0°, θmin = 3.2°
Tmin = 0.726, Tmax = 0.943h = −22→22
17695 measured reflectionsk = −16→15
5178 independent reflectionsl = −27→27
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068 w = 1/[σ2(Fo2) + (0.0524P)2 + 7.2513P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138(Δ/σ)max < 0.001
S = 1.25Δρmax = 0.62 e Å−3
5178 reflectionsΔρmin = −0.80 e Å−3
372 parameters
Crystal data top
(C24H20P)2[Sn(C2H3NO2S3)3]V = 5887.75 (15) Å3
Mr = 1305.13Z = 4
Monoclinic, C2/cMo Kα radiation
a = 18.5563 (3) ŵ = 0.86 mm−1
b = 13.6096 (2) ÅT = 298 K
c = 23.3203 (3) Å0.40 × 0.11 × 0.07 mm
β = 91.355 (1)°
Data collection top
Nonius KappaCCD
diffractometer		5178 independent reflections
Absorption correction: gaussian
(Coppens et al., 1965)		4871 reflections with I > 2σ(I)
Tmin = 0.726, Tmax = 0.943Rint = 0.049
17695 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.138Δρmax = 0.62 e Å−3
S = 1.25Δρmin = −0.80 e Å−3
5178 reflectionsAbsolute structure: ?
372 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1377 (2)0.3823 (4)0.23827 (19)0.0512 (11)
C20.3047 (4)0.2250 (6)0.2112 (3)0.097 (2)
H2A0.29870.18980.24640.146*
H2B0.33550.28070.2180.146*
H2C0.32610.18250.18350.146*
C30.0123 (6)0.7091 (10)0.2265 (5)0.054 (3)0.5
C40.0208 (8)0.9908 (8)0.2192 (6)0.084 (4)0.5
H4A01.04350.250.126*
H4B0.06920.99630.20880.126*0.5
H4C−0.010.99680.18530.126*0.5
C50.1135 (3)0.1693 (4)0.42704 (19)0.0513 (11)
C60.1645 (3)0.0950 (4)0.4278 (2)0.0630 (13)
H60.18250.0710.46260.076*
C70.1888 (4)0.0563 (4)0.3767 (3)0.0807 (17)
H70.22270.0060.37730.097*
C80.1626 (4)0.0925 (5)0.3254 (3)0.0826 (19)
H80.17880.06610.29120.099*
C90.1128 (3)0.1669 (5)0.3238 (2)0.0737 (16)
H90.09570.19120.28880.088*
C100.0883 (3)0.2056 (4)0.3743 (2)0.0602 (13)
H100.05460.25630.37330.072*
C11−0.0120 (2)0.1986 (3)0.50305 (17)0.0482 (11)
C12−0.0622 (3)0.1985 (4)0.45823 (19)0.0546 (12)
H12−0.04720.2070.42080.065*
C13−0.1347 (3)0.1858 (4)0.4689 (2)0.0617 (13)
H13−0.16820.18520.43860.074*
C14−0.1570 (3)0.1742 (4)0.5237 (2)0.0656 (14)
H14−0.20570.16540.53070.079*
C15−0.1080 (3)0.1753 (4)0.5685 (2)0.0715 (15)
H15−0.12370.16770.60580.086*
C16−0.0362 (3)0.1877 (4)0.5588 (2)0.0654 (14)
H16−0.00340.18870.58960.079*
C170.1296 (2)0.1673 (4)0.55250 (18)0.0492 (11)
C180.1161 (3)0.0707 (4)0.5669 (2)0.0622 (13)
H180.08470.03350.54410.075*
C190.1486 (3)0.0285 (4)0.6148 (2)0.0689 (14)
H190.1392−0.03660.62430.083*
C200.1953 (3)0.0845 (5)0.6485 (2)0.0722 (16)
H200.21740.05680.68090.087*
C210.2091 (3)0.1798 (5)0.6346 (2)0.0731 (17)
H210.24050.21670.65770.088*
C220.1768 (3)0.2223 (4)0.5866 (2)0.0622 (13)
H220.18680.28730.57720.075*
C230.0993 (3)0.3510 (4)0.4934 (2)0.0541 (12)
C240.1468 (3)0.3929 (4)0.4560 (3)0.0711 (15)
H240.16730.3550.42750.085*
C250.1640 (4)0.4919 (4)0.4611 (3)0.092 (2)
H250.19570.52060.43560.11*
C260.1348 (4)0.5465 (5)0.5030 (4)0.102 (2)
H260.14710.61250.50670.122*
C270.0883 (5)0.5062 (5)0.5395 (4)0.114 (3)
H270.06880.54450.56830.137*
C280.0690 (4)0.4077 (5)0.5346 (3)0.093 (2)
H280.03560.38080.55920.111*
N10.1997 (2)0.3395 (3)0.23680 (16)0.0549 (10)
N30.0164 (4)0.8014 (7)0.2123 (3)0.059 (2)0.5
O10.1729 (2)0.1825 (3)0.18192 (17)0.0874 (13)
O20.2311 (2)0.3177 (3)0.13255 (15)0.0814 (12)
O3−0.0270 (8)0.8837 (7)0.1904 (4)0.134 (5)0.5
O4−0.0792 (5)0.8933 (8)0.2542 (6)0.132 (4)0.5
P10.08248 (6)0.22110 (9)0.49273 (5)0.0472 (3)
S10.12124 (7)0.45967 (11)0.29633 (6)0.0639 (4)
S20.06587 (7)0.37025 (12)0.18873 (5)0.0676 (4)
S30.22079 (7)0.26505 (11)0.18510 (5)0.0629 (4)
S50.01886 (19)0.6562 (3)0.21037 (15)0.0599 (8)0.5
S40.04165 (16)0.6248 (2)0.17458 (13)0.0629 (7)0.5
S600.88818 (17)0.250.0880 (7)
Sn100.49240 (4)0.250.0642 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.053 (3)0.053 (3)0.047 (2)−0.009 (2)−0.010 (2)0.005 (2)
C20.091 (4)0.108 (5)0.092 (5)0.040 (4)−0.011 (4)−0.022 (4)
C30.041 (6)0.061 (9)0.060 (7)−0.007 (6)0.001 (5)0.002 (6)
C40.109 (10)0.043 (7)0.099 (9)0.013 (6)0.004 (7)0.007 (6)
C50.059 (3)0.047 (3)0.047 (3)−0.009 (2)0.002 (2)−0.002 (2)
C60.075 (3)0.056 (3)0.059 (3)0.008 (3)0.009 (2)−0.001 (2)
C70.103 (5)0.056 (4)0.085 (4)0.004 (3)0.028 (4)−0.012 (3)
C80.115 (5)0.071 (4)0.062 (4)−0.029 (4)0.026 (3)−0.023 (3)
C90.095 (4)0.076 (4)0.050 (3)−0.026 (4)0.002 (3)−0.003 (3)
C100.071 (3)0.061 (3)0.048 (3)−0.009 (3)0.002 (2)−0.001 (2)
C110.056 (3)0.047 (3)0.041 (2)−0.003 (2)−0.003 (2)−0.0003 (19)
C120.064 (3)0.057 (3)0.042 (2)0.001 (2)−0.008 (2)0.000 (2)
C130.057 (3)0.063 (3)0.064 (3)0.001 (2)−0.017 (2)−0.001 (3)
C140.051 (3)0.066 (4)0.080 (4)−0.004 (3)0.001 (3)0.007 (3)
C150.064 (3)0.090 (4)0.061 (3)−0.003 (3)0.006 (3)0.012 (3)
C160.057 (3)0.089 (4)0.049 (3)−0.005 (3)−0.008 (2)0.006 (3)
C170.047 (2)0.059 (3)0.041 (2)0.000 (2)−0.0049 (19)−0.004 (2)
C180.070 (3)0.060 (4)0.055 (3)0.002 (3)−0.015 (2)−0.003 (2)
C190.075 (4)0.070 (4)0.061 (3)0.013 (3)−0.009 (3)0.009 (3)
C200.058 (3)0.106 (5)0.051 (3)0.019 (3)−0.010 (2)0.005 (3)
C210.055 (3)0.115 (6)0.049 (3)−0.008 (3)−0.011 (2)−0.007 (3)
C220.058 (3)0.077 (4)0.051 (3)−0.008 (3)−0.003 (2)−0.002 (3)
C230.060 (3)0.045 (3)0.057 (3)−0.002 (2)0.002 (2)−0.009 (2)
C240.075 (4)0.051 (3)0.087 (4)−0.004 (3)0.014 (3)−0.009 (3)
C250.096 (5)0.056 (4)0.125 (6)−0.016 (3)0.028 (4)−0.008 (4)
C260.108 (5)0.054 (4)0.143 (7)−0.012 (4)0.016 (5)−0.017 (4)
C270.154 (7)0.066 (5)0.126 (6)−0.003 (5)0.041 (6)−0.044 (4)
C280.119 (5)0.067 (4)0.094 (4)−0.008 (4)0.042 (4)−0.026 (4)
N10.052 (2)0.060 (3)0.052 (2)0.001 (2)−0.0102 (17)−0.0085 (19)
N30.066 (5)0.058 (6)0.054 (5)0.002 (4)0.007 (4)−0.012 (4)
O10.110 (3)0.079 (3)0.074 (3)−0.031 (2)0.014 (2)−0.023 (2)
O20.080 (3)0.110 (3)0.055 (2)−0.010 (2)0.0100 (18)0.006 (2)
O30.270 (15)0.073 (6)0.058 (5)−0.038 (8)−0.046 (7)0.013 (4)
O40.095 (7)0.110 (8)0.193 (12)−0.006 (6)0.054 (7)−0.038 (8)
P10.0522 (7)0.0475 (7)0.0416 (6)−0.0017 (5)−0.0034 (5)−0.0020 (5)
S10.0551 (7)0.0641 (9)0.0713 (8)0.0058 (6)−0.0250 (6)−0.0177 (7)
S20.0568 (7)0.0928 (11)0.0523 (7)−0.0070 (7)−0.0166 (6)−0.0055 (7)
S30.0668 (8)0.0698 (9)0.0521 (7)−0.0048 (7)−0.0010 (6)−0.0083 (6)
S50.0665 (19)0.060 (2)0.053 (2)−0.0027 (18)0.0020 (15)0.0058 (16)
S40.0832 (19)0.0563 (17)0.0500 (15)−0.0006 (14)0.0157 (14)−0.0023 (13)
S60.112 (2)0.0629 (14)0.0878 (16)0−0.0187 (13)0
Sn10.0555 (3)0.0525 (4)0.0834 (4)0−0.0268 (3)0
Geometric parameters (Å, °) top
C1—N11.290 (6)C17—P11.785 (4)
C1—S11.748 (5)C18—C191.381 (7)
C1—S21.751 (4)C18—H180.93
C2—S31.746 (6)C19—C201.385 (8)
C2—H2A0.96C19—H190.93
C2—H2B0.96C20—C211.363 (8)
C2—H2C0.96C20—H200.93
C3—S50.822 (12)C21—C221.385 (7)
C3—N31.302 (15)C21—H210.93
C3—S5i1.750 (12)C22—H220.93
C3—S41.763 (14)C23—C281.364 (7)
C4—S61.621 (11)C23—C241.378 (7)
C4—O4i1.813 (16)C23—P11.795 (5)
C4—O31.826 (16)C24—C251.389 (8)
C4—H4A1.0919C24—H240.93
C4—H4B0.9393C25—C261.352 (9)
C4—H4C0.9675C25—H250.93
C5—C61.383 (7)C26—C271.343 (10)
C5—C101.396 (7)C26—H260.93
C5—P11.794 (5)C27—C281.391 (9)
C6—C71.387 (7)C27—H270.93
C6—H60.93C28—H280.93
C7—C81.373 (9)N1—S31.630 (4)
C7—H70.93N3—S61.508 (8)
C8—C91.370 (9)N3—S51.977 (9)
C8—H80.93O1—S31.433 (4)
C9—C101.378 (7)O2—S31.436 (4)
C9—H90.93O3—S61.469 (8)
C10—H100.93O4—S61.477 (9)
C11—C121.383 (6)S1—Sn12.5125 (12)
C11—C161.394 (6)S2—Sn12.5262 (15)
C11—P11.802 (5)S5—C3i1.750 (12)
C12—C131.384 (7)S5—Sn12.441 (4)
C12—H120.93S4—Sn12.646 (3)
C13—C141.361 (7)S6—O3i1.469 (8)
C13—H130.93S6—O4i1.477 (9)
C14—C151.369 (7)S6—N3i1.508 (8)
C14—H140.93S6—C4i1.621 (11)
C15—C161.367 (7)Sn1—S5i2.441 (4)
C15—H150.93Sn1—S1i2.5125 (12)
C16—H160.93Sn1—S2i2.5262 (15)
C17—C181.382 (7)Sn1—S4i2.646 (3)
C17—C221.388 (7)
N1—C1—S1117.7 (3)C26—C25—C24120.0 (6)
N1—C1—S2127.2 (4)C26—C25—H25120
S1—C1—S2115.1 (3)C24—C25—H25120
S3—C2—H2A109.5C27—C26—C25120.5 (6)
S3—C2—H2B109.5C27—C26—H26119.7
H2A—C2—H2B109.5C25—C26—H26119.7
S3—C2—H2C109.5C26—C27—C28120.7 (6)
H2A—C2—H2C109.5C26—C27—H27119.7
H2B—C2—H2C109.5C28—C27—H27119.7
S5—C3—N3136.0 (15)C23—C28—C27119.5 (6)
S5—C3—S5i94.5 (11)C23—C28—H28120.2
N3—C3—S5i129.3 (10)C27—C28—H28120.2
N3—C3—S4115.7 (9)C1—N1—S3122.0 (3)
S5i—C3—S4115.0 (7)C3—N3—O3142.3 (10)
S6—C4—H4A100.5C3—N3—S6126.4 (9)
O4i—C4—H4A118.3O3—N3—S5140.2 (7)
O3—C4—H4A126.2S6—N3—S5143.2 (6)
S6—C4—H4B115N3—O3—O494.0 (7)
C4i—C4—H4B134.1N3—O3—C4102.9 (8)
O3—C4—H4B115.4C17—P1—C5110.1 (2)
H4A—C4—H4B118.2C17—P1—C23108.4 (2)
S6—C4—H4C107C5—P1—C23109.6 (2)
C4i—C4—H4C115.6C17—P1—C11106.7 (2)
O4i—C4—H4C132.7C5—P1—C11112.4 (2)
H4A—C4—H4C105.7C23—P1—C11109.6 (2)
H4B—C4—H4C109.4C1—S1—Sn186.82 (15)
C6—C5—C10119.0 (4)C1—S2—Sn186.33 (17)
C6—C5—P1120.7 (4)O1—S3—O2116.2 (2)
C10—C5—P1120.3 (4)O1—S3—N1111.5 (2)
C5—C6—C7120.2 (5)O2—S3—N1111.1 (2)
C5—C6—H6119.9O1—S3—C2108.7 (3)
C7—C6—H6119.9O2—S3—C2108.5 (3)
C8—C7—C6119.8 (6)N1—S3—C299.5 (3)
C8—C7—H7120.1C3—S5—S4142.7 (11)
C6—C7—H7120.1S4—S5—C3i175.2 (4)
C9—C8—C7120.8 (5)S4—S5—N3116.1 (3)
C9—C8—H8119.6C3i—S5—N364.0 (4)
C7—C8—H8119.6C3—S5—Sn1127.1 (10)
C8—C9—C10119.8 (5)S4—S5—Sn189.6 (3)
C8—C9—H9120.1C3i—S5—Sn190.2 (5)
C10—C9—H9120.1N3—S5—Sn1154.2 (3)
C9—C10—C5120.4 (5)S5—S4—Sn167.3 (3)
C9—C10—H10119.8C3—S4—Sn183.5 (4)
C5—C10—H10119.8O3i—S6—O3175.2 (8)
C12—C11—C16118.7 (4)O3i—S6—O4104.9 (7)
C12—C11—P1122.6 (3)O3—S6—O475.4 (7)
C16—C11—P1118.6 (3)O4i—S6—O4174.6 (9)
C11—C12—C13120.2 (4)O3—S6—N3i116.8 (5)
C11—C12—H12119.9O4i—S6—N3i106.9 (5)
C13—C12—H12119.9O4—S6—N3i77.4 (6)
C14—C13—C12120.1 (5)O3i—S6—N3116.8 (5)
C14—C13—H13119.9O3—S6—N359.0 (5)
C12—C13—H13119.9O4i—S6—N377.4 (6)
C13—C14—C15120.3 (5)O4—S6—N3106.9 (5)
C13—C14—H14119.9N3i—S6—N376.9 (7)
C15—C14—H14119.9O3i—S6—C4i72.3 (6)
C16—C15—C14120.5 (5)O3—S6—C4i112.1 (7)
C16—C15—H15119.7O4i—S6—C4i103.7 (7)
C14—C15—H15119.7O4—S6—C4i71.5 (6)
C15—C16—C11120.2 (5)N3i—S6—C4i111.3 (6)
C15—C16—H16119.9N3—S6—C4i170.6 (6)
C11—C16—H16119.9O3i—S6—C4112.1 (7)
C18—C17—C22119.3 (4)O3—S6—C472.3 (6)
C18—C17—P1119.5 (3)O4i—S6—C471.5 (6)
C22—C17—P1121.1 (4)O4—S6—C4103.7 (7)
C19—C18—C17120.9 (5)N3—S6—C4111.3 (6)
C19—C18—H18119.5S5i—Sn1—S548.15 (19)
C17—C18—H18119.5S5i—Sn1—S197.70 (9)
C18—C19—C20119.0 (6)S5—Sn1—S1100.94 (9)
C18—C19—H19120.5S5—Sn1—S1i97.70 (9)
C20—C19—H19120.5S5i—Sn1—S2i108.13 (10)
C21—C20—C19120.5 (5)S5—Sn1—S2i152.94 (10)
C21—C20—H20119.7S1—Sn1—S2i94.61 (5)
C19—C20—H20119.7S1i—Sn1—S2i71.71 (4)
C20—C21—C22120.7 (5)S5i—Sn1—S2152.94 (10)
C20—C21—H21119.7S5—Sn1—S2108.13 (10)
C22—C21—H21119.7S1—Sn1—S271.71 (4)
C21—C22—C17119.5 (5)S1i—Sn1—S294.61 (5)
C21—C22—H22120.2S5—Sn1—S4i71.14 (14)
C17—C22—H22120.2S1—Sn1—S4i96.17 (7)
C28—C23—C24119.5 (5)S2i—Sn1—S4i85.36 (8)
C28—C23—P1119.3 (4)S2—Sn1—S4i167.66 (7)
C24—C23—P1121.0 (4)S1—Sn1—S497.69 (8)
C23—C24—C25119.8 (5)S1i—Sn1—S496.17 (7)
C23—C24—H24120.1S2i—Sn1—S4167.66 (7)
C25—C24—H24120.1S2—Sn1—S485.36 (8)
C10—C5—C6—C7−1.3 (8)C3i—C3—N3—S65.2 (18)
P1—C5—C6—C7−179.2 (4)S5i—C3—N3—S65.2 (15)
C5—C6—C7—C80.6 (9)S4—C3—N3—S6−175.4 (6)
C6—C7—C8—C90.3 (9)S4—C3—N3—N3i−177.0 (8)
C7—C8—C9—C10−0.5 (9)C3i—C3—N3—S5−173 (3)
C8—C9—C10—C5−0.2 (8)S5i—C3—N3—S5−173 (3)
C6—C5—C10—C91.1 (7)S4—C3—N3—S56.0 (12)
P1—C5—C10—C9179.1 (4)C18—C17—P1—C5−70.6 (4)
C16—C11—C12—C13−1.2 (7)C22—C17—P1—C5112.8 (4)
P1—C11—C12—C13−176.7 (4)C18—C17—P1—C23169.5 (4)
C11—C12—C13—C140.5 (8)C22—C17—P1—C23−7.1 (4)
C12—C13—C14—C150.2 (8)C18—C17—P1—C1151.6 (4)
C13—C14—C15—C16−0.3 (9)C22—C17—P1—C11−125.0 (4)
C14—C15—C16—C11−0.4 (9)C6—C5—P1—C172.9 (5)
C12—C11—C16—C151.1 (8)C10—C5—P1—C17−175.1 (4)
P1—C11—C16—C15176.8 (4)C6—C5—P1—C23122.0 (4)
C22—C17—C18—C190.3 (7)C10—C5—P1—C23−55.9 (4)
P1—C17—C18—C19−176.3 (4)C6—C5—P1—C11−115.9 (4)
C17—C18—C19—C200.0 (8)C10—C5—P1—C1166.2 (4)
C18—C19—C20—C21−0.1 (8)C28—C23—P1—C17−71.1 (5)
C19—C20—C21—C22−0.2 (8)C24—C23—P1—C17103.7 (5)
C20—C21—C22—C170.5 (8)C28—C23—P1—C5168.7 (5)
C18—C17—C22—C21−0.5 (7)C24—C23—P1—C5−16.5 (5)
P1—C17—C22—C21176.1 (4)C28—C23—P1—C1145.0 (5)
C28—C23—C24—C250.9 (9)C24—C23—P1—C11−140.3 (4)
P1—C23—C24—C25−173.9 (5)C12—C11—P1—C17−157.2 (4)
C23—C24—C25—C260.7 (11)C16—C11—P1—C1727.3 (5)
C24—C25—C26—C27−1.0 (13)C12—C11—P1—C5−36.4 (5)
C25—C26—C27—C28−0.3 (14)C16—C11—P1—C5148.1 (4)
C24—C23—C28—C27−2.2 (10)C12—C11—P1—C2385.7 (5)
P1—C23—C28—C27172.7 (6)C16—C11—P1—C23−89.8 (4)
C26—C27—C28—C232.0 (13)N1—C1—S1—Sn1178.7 (4)
S1—C1—N1—S3179.5 (2)S2—C1—S1—Sn1−2.4 (2)
S2—C1—N1—S30.7 (6)N1—C1—S2—Sn1−178.8 (4)
S5—C3—N3—O394 (2)S1—C1—S2—Sn12.4 (2)
C3i—C3—N3—O3−80 (2)C1—N1—S3—O1−60.3 (5)
S4—C3—N3—O399.6 (15)C1—N1—S3—O271.0 (5)
S5—C3—N3—S6178.6 (15)C1—N1—S3—C2−174.8 (5)
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O4ii0.962.353.284 (13)166
C16—H16···O3iii0.932.603.2203 (10)125
C19—H19···O1iv0.932.473.296 (7)148
C28—H28···S4iii0.932.693.345 (5)128
Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) x, −y+1, z+1/2; (iv) x, −y, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O4i0.962.353.284 (13)166
C16—H16···O3ii0.932.603.2203 (10)125
C19—H19···O1iii0.932.473.296 (7)148
C28—H28···S4ii0.932.693.345 (5)128
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y+1, z+1/2; (iii) x, −y, z+1/2.
Acknowledgements top

The authors are grateful to FAPEMIG and CNPq for financial support.

references
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